A new trend coming out of China is quietly changing how people think about job security. And it's not what you'd expect.

The Viral Tool

There's a viral tool people are using called "colleague.skill" (on GitHub) to turn coworkers into AI agents. Not metaphorically. Literally.

They're feeding in:

• Chats
• Emails
• Documents
• Workflows

All to build AI replicas of their coworkers that can do the same job.

Let that sink in.

Instead of employee vs AI, it's becoming employee vs employee leveraging AI.

The Counter-Movement

Here's where it gets even more interesting. A counter-movement has already started.

People are now using tools that subtly rewrite their own documents. Keeping them readable for humans, but poisoning them for AI training models.

So now we have:

• Employees training AI to replace coworkers
• Coworkers sabotaging AI training data
• Companies unknowingly sitting on both

The Real Stakes

This isn't just about AI. It's about who controls the knowledge layer inside organizations.

Because in the near future, your value won't just be what you do. It will be how replicable you are. Understanding the human skills that make us irreplaceable has never been more important.

So the real question becomes: Are you building leverage, or leaving behind a blueprint to replace yourself?

What's Next

The workplace is shifting fast. Those who understand this dynamic will be better positioned to protect their value and make strategic career moves.

The bottom line? Your job security may depend less on competing with AI directly and more on how you navigate this new employee-vs-employee landscape.

I'm curious: If your company trained an AI on your work today, how much of your job could it actually do?

Read that again.

The CTO of a $31B public company walked away from the "top" of his career to become a Technical Staff Member.

This isn't a step down.

It's a signal.

The Talent Migration

We're watching the beginning of a talent migration in real time:

• Titles matter less
• Speed matters more
• Proximity to AI matters most

This kind of career jump tells us something important. The smartest people aren't chasing prestige anymore. They're chasing impact. And right now, AI is where that impact lives.

What This Means

When someone walks away from a C-suite role at a $31B company to get closer to the frontier of AI, it says everything about where the real opportunities are. The traditional career lessons we've learned might need updating.

Titles don't define success. Position matters. And being close to the most transformative technology of our time? That matters most.

Pay attention to where top talent is moving. It might be time to rethink what "career progression" really means.

They average $27M in revenue per location in the U.S. You'd think maybe they only have a couple restaurants. They have 17. And it's family owned and run. Let that sink in.

The Numbers

For context:

• Chick-fil-A: $9M
• Mastro's: $14.5M
• Cheesecake Factory: $12.4M
• Nobu: $10M
• McDonald's: $3.9M
• Benihana: $6.5M

They're not just winning. They're doubling (or 7x-ing) industry benchmarks.

The Playbook

So what's the playbook? It's not hype. It's not shortcuts. It's operational obsession.

Every dumpling:

• Exactly 5 grams
• Precisely 18 folds
• Made by chefs who train for 6 months

Thousands of reps before they ever touch a guest plate. That level of precision scales. And it compounds.

Three Pillars

To reach elite unit economics, every great restaurant nails 3 things:

1. Size → Enough capacity to matter
2. Spend → A product people will pay for
3. Throughput → Constant demand

Din Tai Fung dominates all three. Big footprint. Premium pricing power. Lines out the door.

The Real Insight

But here's the thing. Consistency creates trust. Trust creates demand. Demand creates volume. Volume creates dominance.

Everyone wants growth. Very few are willing to standardize excellence at this level. That's the difference between a good brand and a category-defining machine.

Key Takeaway

Din Tai Fung proves that operational obsession beats hype every time. Precision, consistency, and relentless standards create the flywheel that turns a restaurant into an empire.

The lesson? Don't chase shortcuts. Build systems that scale excellence. That's how you go from fighting for margins to dominating an entire category.

What's one business you've seen execute at this level?

Here's something I've noticed: I've been more honest with people I met once over coffee than with friends I've had for 20 years. That shouldn't happen. But it does. A lot.

So I started thinking about this more seriously. And I have a name for it: The Friendship Infrastructure Dilemma. Because most relationships are built on performance, not truth.

The Performance Problem

When you're younger, you don't lead with vulnerability.

You lead with:

• Fitting in
• Being liked
• Playing a role

So your friendships get built on a version of you that isn't even fully real. And then something subtle happens: that version becomes permanent.

"This is who I am with you." "This is who you are with me." And nobody questions it.

Years go by. You grow. You change. You become more self-aware. But the relationship doesn't.

The Unspoken Contract

Because updating it would mean breaking the unspoken contract. So most people don't. They keep showing up as who they used to be around people who expect that version. And they call it "loyalty."

But a lot of the time? It's just inertia.

This is why so many people outgrow their high school and college friendships. Not because they think they're "better." But because those relationships were built before they knew who they actually were.

The New Advantage

Meanwhile, new relationships have a huge advantage: No history. No expectations. No identity to maintain.

So you can skip the performance. You can just tell the truth. And when you do that, you can build more depth in one conversation than in years of "close" friendship.

Read that again.

In my experience, some of the most meaningful relationships in your life will start fast. Because they start real. It's one of those career lessons that applies just as much to your personal life.

Time vs. Truth

Which leads to this: Time doesn't create depth. It exposes whether there was ever depth to begin with.

If a relationship wasn't built on vulnerability, time won't fix it. It will just lock it in.

Your Choice

So you have a choice: Keep maintaining relationships built on an outdated version of you. Or start building ones that reflect who you actually are.

Most people choose the first. That's why real depth is rare.

The bottom line? We underestimate how much relationships are designed, whether intentionally or not. Time alone won't create the connections you're looking for. Truth will.

The people who matter most in your life will be the ones who know the real you. Not the version you performed years ago.

Start building relationships that reflect who you actually are today.

In this article I've summarized the key topics we covered. You can also find the link to the full episode and the complete transcript below.

Topics We Covered

Jess and I went deep on what it actually takes to build a network that opens doors rather than one that just looks good on paper. A few of the themes we kept coming back to:

• Building and exiting companies across unexpected industries — from a 340B health tech platform and a Latin American software staffing firm to a farmland leasing marketplace, and what I've learned about timing, relationships, and knowing when to sell
• Why in-person events have become more valuable, not less — what made early conferences transformational, why most events have lost that magic, and how Jess Ma and I launched Outcove to bring it back
• The art of non-transactional connection — why leading with generosity, asking great questions, and making introductions without keeping score has been the foundation of almost every meaningful opportunity in my life
• Rookie mistakes in high-trust rooms — pitching too fast, talking too much, and asking for introductions before building any goodwill, and what to do instead

Watch Now

Watch the full conversation below, or click here to watch on YouTube.

Full Transcript

Jess Larson: Welcome to the Jess Larson show on innovation and leadership on this episode. Back with my good friend Noah Berkson. Noah, thanks for making time.

Noah Berkson: Thank you so much for having me, Jess.

Jess Larson: So I really want to talk about something you and I talk about all the time, which is like the power of in person events and how like one to one relationships are like more powerful. I think we all got zoomed out too much on Covid and you're kind of like a master super connector. So I really want to get our audience to understand like why this has worked so well for you and but for folks who didn't catch your previous episode, can you give us a background on you, kind of some of the big business highlights, including your recent exit. And then we'll talk a little bit about your co founder and then I want to talk, I want to jump into outcove.

Noah Berkson: Well, first off, thanks for having me and I think getting, getting called a super connector from you is probably the highest honor there is because I don't know anyone that's at the, at the velocity you are with connecting people and bringing people together. But yeah, I grew up in the Midwest. Terrible, terrible student, barely, you know, graduated high school, barely got into college, talked my way in, had terrible adhd. You probably still notice a little bit of that today. But got really lucky, ended up starting a company in college. I realized that when I could focus on something, I was quite good at it when I could put all of my energy into something and I was really stimulated by it. And have started a lot of companies, definitely not all successful, have just sold the fourth about a week ago, which is really exciting, I think. I tell people it's just a power law game. You kind of take enough swings and you get lucky sometimes. So that's kind of, that's been my, that's been my mentality. And tell us about this, Ben.

Jess Larson: Tell us about the company. Well, what are the first three companies you sold? And then let's go a little deeper into the last one.

Noah Berkson: Yeah. So we had a health tech business in the 340v space, which is a 340v is a federal drug discount program in the US and built a point of care solution for hospitals, health systems, federally qualified health clinics that would facilitate this program. So virtually helping patients who are uninsured or underinsured get better priced drugs. And then also the entities that care for those patients make money directly from the drug manufacturers. And so we sold that to a private equity roll up. Had a software staffing business that I sold in 2021.

Jess Larson: Just quickly. How old were you when you sold your first one?

Noah Berkson: Well, we actually, we sold that, like, to about two years ago, a little less than two years ago now. So that wasn't an early exit, but something that was started a long time ago and then had a software staffing business called Dev Base. We employed hundreds of software engineers in South America, Latin America, Asia, and we would staff them to companies mostly in the US a little bit of Europe, which we sold in 21 to a core banking provider. So a company that provides software to banks, infrastructure to banks. Think of it as like a modern fis, Pfizer, Jack Henry, or some of the large players in the space that people would know had a. Had a venture fund and studio called Kander Ventures that we ended up selling in early 2022 and just sold a farmland marketplace. So we were the largest farmland leasing marketplace. Think of us like ebay for ebay for leasing farm ground. A lot of people don't know about half of all farm ground in the US Is leased, so it's not farmed by the owner. So we were a market maker and facilitated those transactions. And that's a whole other whole other industry that is super interesting for a lot of reasons. But, you know, you're trying to bring a business.

Jess Larson: Yeah, your average business that your typical young guy in Orange county owns.

Noah Berkson: That's exactly right. That's exactly right.

Jess Larson: How did you end up in Farmland leasing?

Noah Berkson: Actually meeting somebody that had an idea in the space. I grew up in Iowa, so I grew up around farming. So I knew, you know, I knew a bit about it. I would say I was by no means an expert in it, but, you know, grew up in one of the largest ag states that there is. So I had a lot of familiarity. And like everything else, I think I like to find things kind of my philosophy and philosophy is maybe a little bit generous, but kind of the way that I've fallen into things or found opportunities is finding things that from the outside look like they could be done differently in industries that I don't know enough about to understand why they wouldn't be done that way. Right. So being able to say, hey, that seems like you should be able to do this differently. Farmland should be leased online. Why is it not? You know, why is it leased in person? And why is your network determine who you can get to farm your ground? And you see that from the outside and go, oh, well, seems like easy. You just start a marketplace and, you know, people. Landowners put up land, farmers bid on it. Simple. But you don't know that that industry has not changed for a very, very, very long time and has been very averse to technology. The average landowner in the US is in their mid-70s, the average farmer in their late 60s. And so you don't know enough to understand why that doesn't operate that way. But then you're in it and you start something and now the only way through is through. And yeah, that works occasionally.

Jess Larson: Yeah. So how many years were you in that business?

Noah Berkson: Since 20. 20.

Jess Larson: Okay.

Noah Berkson: Yeah. A little over five years.

Jess Larson: A little over five years. What's one of your takeaways?

Noah Berkson: We technically started in 2019. Takeaways for the future. I think I was also getting into businesses many times where I had to sell, I had to educate people. So I was bringing some solution to the market where you had to educate people. Educate people not only about the problem, but then about the solution. And I learned that that was very hard. Educating people is not a fun thing to do. It's time intensive and it's very expensive. And so I think what I learned from that is moving forward, I want to focus on things where I am, where people are buying a product that I have, I am not selling it. So it is already something they know that they need, they understand it and I can just provide the better, cheaper, faster solution to that. I think that was, that was probably my, that was probably one of my biggest takeaways. But also that, you know, when you, when you have a will in something and you want to change something, you can make it happen. It's, you know, it's by no means, by no means easy, but you just kind of go through it and through it and through it. The amount of times in that business where we thought everything was not going to work and we weren't, you know, we weren't going to be successful. I mean, that was, that was a daily feeling for the last five years. And it's cool, it's cool to see it turn out the way that it did.

Jess Larson: Yeah, it's interesting. I do think about that for our, you know, for our company, you know, luxury vacation home co ownership business. We regularly get offered places that look beautiful. People like, oh, yeah, you know, you know, maybe we could do that with, with my, you know, home number five, right. And it's like beautiful, it's on some lake or something. But I'm like, I don't, you know, stunning place. But I'm looking for places where I don't have to explain where it is when I say we're doing something you know, in the Caribbean, on the, you know, beachfront in the Cayman Islands, or we're doing Hawaii or we're doing Aspen. Not, none of the ultra high net worth people are like, where's that? Right?

Noah Berkson: It's, yes. And I think it is just so important and I think even, you know, it's an interesting time right now because with this, I don't know, this AI shift or revolution or boom or whatever you want to call it, there's a lot of new technology that is, you have to educate people on it. And educating people is hard, but the vast majority, I think of businesses are going to be educational businesses from, from how you sell your product standpoint, which, it's just hard. It's just hard. So I, you know, I wish, I wish everybody well doing that. And honestly, a lot of those people, that's where the most opportunity and the most money is, I think in solving those problems that, you know, you have to educate people on. But it's also, you're, you're picking the most uphill road, you know, pushing a boulder up the biggest hill.

Jess Larson: Well, maybe one last question before we move on this. You know, I think about my friends in private equity or people who come on the show and you know, they're saying, oh, we're, we're doing a big roll up in this industry or whatever. So far have not heard someone say, like, man, if I could just find a farmland business. Okay, so when, when it comes to getting the number you're happy with, you know, on this exit, what's, what's a thought, what's a principle? When, when you're talking to entrepreneurs who might be listening today who are, you know, it's clear that, you know, they've built something to the point where it should be able to attract the kind of number they're looking for. And now they need to run a process or now they need to start, you know, maybe talking to some strategic buyers, talk to some financial buyers. What's a principle or lesson?

Noah Berkson: That's a good question. That's a great question. I think I have a few thoughts on this one. I think timing is everything. And I see this time and time again with friends of mine that have built businesses, they've built incredible businesses. And today they go, if I would have sold my company five years ago, I would have made more money than I'm going to today. Right? Because industries change, multiples change, things get commoditized, A lot of people come into the market and so understanding when, like, when is a good outcome for you. And I think it goes against most venture capital because venture right would say, hey, we need these, we need a huge return or we're not really interested in this business. And so as a founder, they go, you're going to keep pushing and pushing and pushing. And I'd rather it be a 0 than be like a 1/2 right compared to the thing that, the outcome that I want. And so I think it puts a lot of people who take venture money and don't really realize what they're signing up for ahead of time. Um, it can put you in a really precarious situation because you're forced to keep going. But the industry may be changing there. I, I see so many people in this situation that are there right now. They're like, if I would have sold my business years ago, I would have made way more money than I will today. And that's really hard. It's really hard to see that as a founder to say, wow, like I should, I should have, you know, I should have done this. I think also talking to people ahead of time and building relationships, I think most transactions are relationship driven. And yes, of course you have some companies that, hey, we need to buy this because it is so strategic that we need this company or it's a cash flow asset, which most startup companies are not cash flow, they're not cash generating machines, they're money losing machines. A lot of those are all going to be relationships. And so I think building those relationships early is really important. Some people go, well, I don't want to talk to anyone. I don't want them to know that I might sell in the future. I want to keep all the cards close. It's kind of like, you know, founders who will, who will email us for investment and they'll say, hey, can you sign an NDA to look at our, to look at the business? And it's like you just don't really understand how this works. I think those are two really, really important things.

Jess Larson: Yeah, no, I totally agree. I mean that's very much. I think it's one of the things you and I agree the most on. And when you say we in that sentence, do you want to talk about like who you're investing with these days and how you're allocating capital?

Noah Berkson: Yeah. Today, from the family office perspective or Austin capital perspective, we invest in predominantly fintech and financial service businesses. One of the things that we invest in are community banks. And so probably highest up on the list are community banks, which are like the most non venture type of business. Like an old boring business that we think we can bring. You know, we, we have a, we have technology that powers banks. And so we want to invest in banks, we want to then help equip them to run more efficiently, gain more customers, make more money. So we think that's a really good investment for us. Outside of that, we're looking for things that are additive to the, additive to the companies that we own today. So we have a core banking business, we have a payments infrastructure company, we own a trust bank, we own a high risk bank. So we want things that can fit into that. One of the things I think that might be challenged a little bit today, like my answer today is a little different than it might have been a year ago is typically when we're investing, especially in the fintech space is what we're looking for is distribution. You have lots of people that come to you and go, oh, look at this technology, technology, technology we've built. And what you realize in that industry, if you've been in it long enough and if you know it, is that everyone is using all the same technology, right? You're still running on the payment rails, you're still running on all of this other people's technology. So there's not much advantage or IP around technology. It's distribution, which is interesting because most people don't realize that. So when they're pitching, they're pitching. Here's this technology we've built, technology, ip, whatever that is. It's not. Here's the really unique distribution angle we have because that's the thing I think that will win not only now, but also in the future. Distribution will be everything, especially as technology gets easier to build. And you know, I can spin up a Neo bank which used to take, you know, years and millions of dollars for, you know, probably not single digits, but, you know, tens of thousands of dollars.

Jess Larson: Yeah. Yeah, I love it. Well, speaking of relationships, let's talk about your co founder, Jess Ma of Altcove, who has also been on the show for you, who missed that episode. Can you give folks a quick background on her?

Noah Berkson: Yeah, Jess is awesome, is a super close friend. I actually met her because of a podcast, which is a whole other story, which is cool, but we met through this podcast. We're both in YPO and we're doing some similar things, but she's also been a serial entrepreneur, has built a bunch of companies, runs a venture studio today, has been in fintech and bio and litigation tech. Probably a much, much more vast, vast amount of industries than, than I Have, but just as a. Is a force of nature. It's just someone that immediately when you meet, you go, that's, that's a person I want in my life. And that person can just run, run through walls to get things done.

Jess Larson: Yeah, I think when she was on the show, she said the combined value of the 10 companies is like a billion and a half.

Noah Berkson: It's incredible. Yes, very, very much so.

Jess Larson: So where did the two of you come up with this idea for your outcome events?

Noah Berkson: Yeah, you know, we both, I think we're both very big relationship people. As in like we, we love meeting people, we love connecting people, but at the core is actually building relationships. It's not a, it's not a transactional nature of meeting people. It's not, I'm meeting you because I need this. Um, it's a, you know, even today I probably spend 15 hours a week meeting people with no agenda. Just you guys should meet. Right? It's not because I want to sell you something. It's not because I want to get something out of you. It's just like I want to, I want to bring great people into my orbit because I, you know, I find that that allows me to bring more great people into my orbit and creates, you know, creates just a lot more cool life experiences and deep relationships and opportunity at times too. But I think that's just not the, that's not the main function. And we had been talking about this one day about how we go to all these events and I think about the best conferences that I've ever been to or heard about. And in the beginning they were really small, right? They were super intimate. Everyone there was very vetted. It was non transactional. You were having real conversations, you're walking away with real friendships and you leave from that changed in some way. You've learned new things. You have people that you're going to incorporate into your life. And that was incredible. And then those things get popular and then they turn into businesses, right? And then it goes away from like, how do we create all this value for this small intimate group to how many people can we get to this event? How can we scale this? Right? And how do we make a bunch of money doing it and we hire a big team and I mean, you know how this goes. And we were, yeah, we were just kind of a little frustrated with the things that we were going to and saying either they've become too big and commercialized or most of the people are there to sell people something. Right? You go to a conference and you're paying a bunch of money to be there. Well, you better, you know, you better get your money's worth, right? You better like sell the thing that you're there to sell. And we were just complaining about this and just like, well, why don't we just like host something? Like why don't we just host our own thing where we bring together a super small curated group of people and we really focus it on relationships and getting to know people. It's like, how do you go make adult friends? I know that sounds like silly on the surface, but I think that's everything. I think adults and I think especially as people get more successful, what I see is they tend to get more secluded and, and more isolated and they kind of get the group that they spend time with and that is the group. And I think that's just such a miss in life when you're not bringing in the new people in, getting the new perspectives, doing the new things. One of my, one of my best friends, one of my best friends has this, has this older friend, maybe we'd call him like a mentor, he's in his mid-70s and he said to my friend Tony, he's like, Tony, like if I have one piece of wisdom for you or advice, hang out with younger people, make friends with younger people, significantly younger than you. It sounds like weird, like that's the life advice that you have for me. And he said, because otherwise you get stuck with all the same people and you're talking about the same things and like your worldview isn't changing, you're not doing the active stuff, you're not getting the new life experiences anymore. And I mean that really resonated with me. So anyway, that was kind of the precipice of this. And also how do you bring together people that are not going to cross paths in their day to day life, Right? So how do you find people that? Because I think for me personally some of the biggest, let's say unlocks in my life have been from conversations with people that are not in my industry that honestly can't even relate to a lot of the stuff that I do. But they open up some new worldview for me, some learning something that changes my life. And I think that's where the magic happens. And so this idea is like, how do we create these intimate conferences, bring together founders, bring together investors, bring together family, offices, award winning musicians, scientists, politicians in this room? Because I think that's where the magic happens. And I think it's like, how do you stay small Enough to be meaningful, but, like, diverse enough to have these breakthroughs and breakthrough relationships that can change people's lives.

Jess Larson: Yeah, you know, there's some science that backs up your opinion. Do you know the book Where Good Ideas Come from by Steven Johnson?

Noah Berkson: I do not.

Jess Larson: It's fascinating. He has a great TED talk, an Even better, probably RSA Talk, Royal Society for the Arts, whether he'd be like a whiteboard animation while he's talking. Right. But I listened to that book a few times.

Noah Berkson: I'm a huge fan.

Jess Larson: And he basically just went through the physical locations where innovation happened over the years. And so he's like, you know, the coffee houses with the Enlightenment, you know, in Europe, or, like, you know, even just like, the East Village during, like, Bob Dylan's time for music when, like, so much happened there. He just goes through, like, where did, like, physically, where did these innovations come from? And, you know, to be like, oh, this building in MIT has had so many more innovative breakthroughs come out than all the other buildings. Like, just is these unique stories, right? And what they find is, it's like most of these stories, whether it's Tim Berners Lee coming up with the World Wide Web, or just all these stories, it's like they work on this hunch that they've got. Then they go out and bump into, like, he calls it a liquid network. Like, go out and bump into ideas that are completely different than yours. Like my favorite author, Richard Koch, the 8020 principle guy, the billionaire who wrote the 8020 principle and came on the podcast, he calls it go bump into ideas from the distant part of the solar system. That's what he calls it. Okay, but in the Steven Johnson book, he's like. He goes through. He's like, they go out and they bump into all these other ideas, Then they go back on their own in solitude and work on their idea. And then they go out and they bump into all these other people. Then they go back in solitude, and it's like they get basically halfway done by doing that. And then all of a sudden, they meet the other half of their idea. They meet the right person, they, whatever. And it's like, it takes, like, 99% of the time to get halfway done and 1% to get the second half done. And so, like, what you're saying is, like, history proves that, right? The people who made huge leaps, how, yes, they're working crazy hard, but they're also out there bumping into concepts, getting out of the group. Think of their industry, of their science, of their group, whatever. It is. And then so, nays, obviously I'm a fan of your approach and I loved the Park City event last year. I'm so sad I missed Hawaii. I'm super stoked for Park City. By the way, anybody listening to this in the beginning of 2026, you can probably still apply. Do you have any spots for people to apply for the, for the march one?

Noah Berkson: We do have a few spots for the march one and I'll ping that also in the show notes so that you have it.

Jess Larson: Yeah. Is there a website or where do people go for that?

Noah Berkson: Outcove.org that's right.

Jess Larson: Okay. So, yeah, I'm going. Noah's nice enough to have me host a panel with our charity Child Rescue Association. I'm going to be hosting a panel of some people I really respect, Dean Stott and, and some other folks talking about making a dent in helping children. What were you going to say, though?

Noah Berkson: I was going to say just, I just want to, if anything I can impress upon people is just like, the one relationship can change your life. I think about that. There's this exercise that I've, I've now done a number of times as I've updated it, but I go, how do you like spider web your life? And what I mean by that is let's take every big thing that's happened in your life and how did you get there? And it's like, who was the person that you met that then introduced you to that opportunity or that person that introduced you to that? And it's like becomes a spider web. And the fascinating thing for me is almost every one of every one of the opportunities that things led to that were very, let's say, like life changing Net positive for my life. They did not come from the people I would have expected. They didn't come from the people that were in the same industry as me. They didn't come from the people that I, you know, see every day and talk to and would run into at the events I'm going to. They came from very random people. And I think that is just like, it's, it's a fun exercise to do one. So I encourage people to do it. But I think that's just how I, how I think about everything. And it's like, let's keep. I want to just, I want to be going and saying yes to things because you never know when that happens. And people get, I think people can quickly get discouraged. You go to one conference and you're like, well, I didn't make that. You know, I didn't get that life changing relationship from this thing. And it's like, yeah, of course not. That would be incredibly lucky if you did. But the odds every single time of you doing that, like you are, you are going to have those things happen.

Jess Larson: Yeah. So let's talk about this more. Let's start with the opposite actually. Let's talk about rookie mistakes. When you see folks who, they finally make it into a room like, you know, at Alcove, you've got, you've got young people who are, you've got young billionaires there, you've got artists there, you've got a very eclectic and very like accomplished group that you gather. Hence the reason I'm excited to come hang out with you next week. But talk to me about rookie mistakes of like the person who shows up and you know, it's trying to get every single person's phone number but not actually building a real connection. Or talk about rookie mistakes for in person events when you're with a bunch of high profile.

Noah Berkson: Yeah, yeah, I think, let's see a lot of them, I think that, I mean the easy ones are like pitching first, right? Is the people that come and just pitch right away, they're like, here's the thing I'm doing and how do I get you involved with it? And then when you're, you know, if you're not interested in, okay, great, I'm going to go on to the next relationship. So it's like being in a place without the mindset of I'm here to build relationships and that's what I'm here to do and not like I'm here to sell somebody something. A lot of times I also see people just talk a lot and the conversation when they meet people is how do I talk as much as possible and impress upon them like how impressive I am or how successful I am. And so many times I watch this, just like I see this and I know exactly, I see one person doing this and like, let's say I'm in a group of three people. Someone comes up, they're talking to the other person and I know exactly how that other per. The person is feeling that is getting this like listening to them and they kind of keep glancing over like, how do I get out of this conversation? People just don't listen. Everyone, like the people do not want to listen. It's just this instinctual thing to be like, oh, how do I kind of puff my chest out and be the, be the, be the successful. Interesting. Here's why you Want to talk to me? Like, my, My. My anecdote for this was, I was at a conference. I was at a conference years ago, but there was someone there that I'd really wanted to meet. And, like, I just seen. I. You know, I followed their career, and I wanted to meet them. And I ended up getting a chance to. To chat with them. And we end up chatting for, like, 45 minutes. Long conversation. You know, I assume it's going to be a short thing, ends up being a long conversation. And at the end of it, he's like, noah, this is one of the best conversations that I've had in a long time. I just want to thank you. This is unexpected and awesome, and my ego is so stroked. I'm walking away with my head held high. And I was thinking about it afterwards, and I said, he doesn't know anything about me. I just asked this guy questions, and he just talked about himself the whole time. And he goes, this is the best conversation I've had. And I'm like, you don't know literally anything about me.

Jess Larson: That is straight out of how to Win Friends and Influence People. You know, that book is 100 years old, and it's still solid gold. I always think it's funny when, like, Harvard types or people want to, like, treat that book like it's below, beneath them. And I'm like, well, let me tell you about, like, the FBI hostage negotiators who come on the show. Let me tell you about, like, the CIA case officers and, like, the people, like, the salespeople who have sold, like, sold hundreds of millions of dollars of their stuff. And why all those people swear by that book. So, you know, like, maybe you ought to go back to that one. And it's kind of like that you can make more friends in two weeks by being interested in others than you can in two months by trying to get them interested in you, right? Or it's like. Like Jim Collins, you know, any good to great when he says that, like, that his advisor said, you spent so much time trying to be interesting. I think you'll do better by trying to spend time being interested.

Noah Berkson: That is a perfect, perfect summation of that. And one of the other things is just people not understanding, not leading with giving first and giving value. I think there's a big misconception, and especially when you're younger in your career, you go, well, if I'm talking to Jess Larson, how do I. How am I valuable to him? Like, he's been really successful. He's doing all these cool Things like, I haven't done all that stuff yet. Like, how do I be valuable? And people don't even really think that. They think. Let me just ask him for things. Let me ask Jess for this and for this and for this, thinking that you're just going to. You're just going to be like, oh, yeah, of course. Let me just do everything I can to help you and open up my network to you when you're not doing anything in return.

Jess Larson: Yes. Yes. That's like my favorite saying. The best way to get. The best way to get a referral is to give five referrals first, Right?

Noah Berkson: Yes.

Jess Larson: And, like, I think one of my favorite stories on that. Do you know who Joe Polish is?

Noah Berkson: Runs the Genius Network. Does that name ring a bell? I don't. No.

Jess Larson: Doesn't matter. So he talks about this story. He, like, is the. My hero for this. He talks about this story, like, paid some money to go to Richard Branson's island to meet Richard Branson. You know, a lot of people have gone to Necker, right? And he's like, there's a whole room full of people that wanted Richard Branson's number. Okay? And people are doing what you said. They're trying to impress him, and they're doing a lot of the talking, whatever. And what does Joe do? He goes up and says. He's like, just thinking, what's in it for them? Right? And he's like, actually, Joe Polish wrote a book called what's In it for them? But he goes up to Richard, he's like, hey, listen, big fan, blah, blah, blah. But listen, your charity sounds really amazing. I would love to know if you'd like any help fundraising for your charity. At which point Richard Branson says, that's so generous of you. Let me give you my number. I want to stay in touch. Let me put you with your staff. And then he went back and actually did deliver. And he used his reputation. You know, it's like, what does Richard Branson need from us? Well, he actually knows Richard Branson, knows a lot of people, but he. He doesn't know everybody. And so Joe used his. Some of his own social capital up. You know, obviously, Joe is like the. In the pecking hierarchy. He's way, way, way down on this list. But he still. He used his time, his connections, his social street cred to raise money for Richard Branson's charity. As a result, he, like, has hung out with him, like, once a year for a decade. And they, like, actually became friends. And like you said, showing up and serving especially to people who usually are getting hit up. You definitely stand apart, right?

Noah Berkson: I. I built my. I mean, I would be nowhere today without that. But, like, the early example of. Of that is I would. When I was in college, right? So I was probably, like, 19 years old. I wanted to. I wanted to get business. I started a company, and I was trying to get business. And what I did is I went and wrote all of these CEOs of large companies. And I would say something to the. And I was like, this is like LinkedIn or cold email. And I'd say something to the effect of like, hey, I'm a young. Like, I'm a young entrepreneur. You know, I'm in college at the time. Young entrepreneur. I've really liked. You know, I've followed your career. I found this, like, really cool. I would love to buy you a coffee and just hear about your experience, like, hear your story. And shockingly, like, Everybody. Not, say 100% of people, but. But a huge amount of them were like, oh, of course. Like, everyone that's writing me is like, I want this from you. I want this from you. Can you buy this product? Can you do this? Can you introduce me to this person? I was like, I just want to hear your story. And I would go and I would ask questions, and I would make sure I bought the. You know, I'd make sure I bought the coffee when I, you know, had no money. But, like, let me. Let me make sure. Just don't order, like, a croissant, too. That might be pushing it, but. And I would go, just ask questions, and I'd be like, oh, how can I be helpful to you? How could I be helpful? At the time, I don't even know how I could be helpful, but I asked the question anyway. And they'd be like, oh, that's so kind. Like, oh, I'm working on this, or whatever it would be. And then they'd go, how can I help you? And I'd be like, oh, no, this was it. This was incredibly helpful to me, like, learning from your journey. And people would be dumbfounded because they're like, this kid came to buy me a coffee and asked how he could help me, and now I can't help him. And then these people are like, how can I help you? Right? I'd start to try and make some introductions because I was meeting other CEOs. I'm like, oh, you got to meet this other guy, right? And so the perceived value of me was really high. And they go, well, wait, what can I do for you. And I'm like, oh, nothing. And that they would just, like, they'd, they'd want to do something so badly, they'd be like frustrated about it. Like, you can't be giving all this value to me. This feels lopsided. Yeah. Just really, really funny thinking back on that.

Jess Larson: It's how you stand out. It's how you get cut through.

Noah Berkson: Right.

Jess Larson: It's how you get cut through with in demand. People is give, don't ask. And in fact, you know, like when they're, when they're asking. Yeah. Anyways, I love your story. Don't need to repeat it.

Noah Berkson: Well, you know, one of the. Oh, sorry, I was just gonna say one of the, one of the things, One of the things I think people also don't realize is like when you ask for an introduction, when I introduce you to somebody, that is my entire reputation on the line, right? Because I have like with my network right now and this, I've worked my entire life to have this. I'm like, there's no opt in for me, right? So it's like, I will introduce you to people that I know you will get along well with. I know will be valuable to you. I know you'll be very thankful. Like, I'm not going to, I'm. I'm not gonna say, hey, do you mind if I introduce you to this person? I'm gonna introduce you to the right people at the right time. And I'm really good at that. So when I'm giving anyone an introduction, they don't realize like the weight that that carries because they're basically getting like a warm. Like you're getting my entire life's work right in that introduction. And there's a lot of weight behind it. I think a lot of people don't realize that. And so they're asking for introductions. It's like, oh, can you introduce me to this person? This person. And not providing any value or any reason to trust them. Like quite the opposite. Cause they're just asking for all this value without, you know, without giving any. And I think that's just a lot of people don't realize kind of the enormity of that or the weight of that and, you know, something relevant.

Jess Larson: It's short term thinking, long term thinking. Somebody short term thinking is going up and asking for an intro, asking for pit, you know, asking for money, asking for an intro, asking for, you know, can I borrow your credibility for myself? Short term, short term thinking, very low probability. People who are high profile are very good at dodging that. And oh, yeah, you know what? Here, let me, let me, let me hand you to my, you know, let me connect you with my CEO about that. Or let me connect you to my family office, you know, and they've got, they're like, they're very skilled at handing you off to their gatekeepers. Who, who are they going to tell you no versus the opposite. Like you said, show up, show up again, and then give some more. And like, and then give some more and then give some more. And it's, it's such a high probability way to start a friendship. And, you know, another one too is like, I think about a guy I really look up to in my 20s, you know, when I was CEO of my first investment fund, right? And our. We are a customer of kpmg. And they're like, biz dev guy, this guy named. I feel so bad. I think it's Jonathan Day. Okay? I remember his last name is Day. I can picture his face. And I remember, like, going to events and I'm like, younger than the other CEOs, by 15, 20 years, whatever, right? And he, every time he'd see me, he'd be like, his name is Chris Day. Every time I'd see him, Chris would be like, okay, what are you doing right now? What are you working on right now? And I started telling him and he was just like, stop, stop, stop. Okay, I've got somebody for you. And he grabbed me by the shoulder and walk me across the room and go introduce me to that person, right? Then he would brag about me to the other person so I didn't have to talk about myself. He would say what he thinks we ought to talk about, and then he'd stay there for a minute for us to exchange. And then he'd slowly slip out and go to it again. And I promise, KPMG made so much money off that guy because he made me feel like a million bucks over and over. And is there anything better than not just, can I introduce somebody eventually? But you know those people at the parties who are like, they keep track of who everyone else is there, and they're like, let me elect myself your assistant. And I'm going to go like, I'm going to walk you over someone right now who I just met 10 minutes ago. They're almost like cataloging who's in the party so they can do matchmaking. People love that person. That is such a great way to start a friendship, right?

Noah Berkson: That is the best person. And that's also the hack for anybody that's kind of getting into this world, right. Is show up early, start to meet people, and then just go introduce people at the same event. It can be a small event, but still in my mind I go, oh, Jess introduced me to that person. That was so, that was so kind of him. Even though, like, I may have run into that. I probably would have run into that person or talked to them throughout the night. But now I'm like, Jess is in my mind as my association between that person.

Jess Larson: Yeah. Especially if you're trying to like break into an industry or you're. You're feeling insecure in a room or something. Right. Like introducing two high profile people to each other when you like, maybe you don't think you're even close to their level. That is, they really value it. Right?

Noah Berkson: They really value it. And something super relevant right now with all this. Have you, have you messed around with some of this open claw stuff? Has this been on your radar?

Jess Larson: I've just been watching social media talk about it. I don't know anything about it.

Noah Berkson: So this is where my brain goes just on this relationship side. But one of the first things I did is I said, okay, after every call I have, I want you to grab like all of like a granola. I don't know granola or whatever note taker you have. Fathom. But I want you to grab the transcript based on what the other person said. I want you to tell me everyone I should introduce them to that's in my network based on all the email introductions I've sent, based on all the other conversations I've had and communications I've had. And it is wildly cool because I go, oh, you know, generally like you and I chat and there's two. I go, oh, I get you're doing this thing. Like I gotta introduce you to these two people or three people.

Jess Larson: Oh, you started the podcast.

Noah Berkson: I might be like half an hour

Jess Larson: late today because of doing that exact thing.

Noah Berkson: Cause we're talking about it. But there might be 10 more people that would be really relevant that are just not top of mind this second. And I go, oh, if instead of giving you three introductions, I can give you like 10 introductions and I can do that with every single person I'm meeting if as long as they're relevant and like the right things. Wow. Like, that's really powerful. I can make, you know, essentially one more introductions a year. Yeah.

Jess Larson: I want to pause you and give you a compliment because I feel like you're one of the best people I've ever met. For giving in a non transactional way. You set such an example for making super high level introductions and then not keeping track. It's not like I did that so you'll do this for me or I do that so you owe me or whatever. And it makes you like incredibly magnetic. No wonder everyone wants to come to your events. No matter I.

Noah Berkson: No wonder I want to come to

Jess Larson: your events is like that people can tell that, that genuine, the genuineness, that sincerity of like. No, this is really just like this is an act of service. This is not a sales technique. This is not what's funny. It's like probably one of the best things you could do for sales if you, if you need sales. But like this like, I can't think of a better word than generosity of like, let me introduce you to your ideal customer. Let me introduce you to your ideal investor. Let me introduce you to the person who's all of their clients are your ideal client. You know, in like this true giving way. You're not keeping track. It's not transactional. It's like truly like almost like a sport of like it feels like when you're doing this, it's almost like what can I do for you when you can't do anything for me? And it's like getting like the Care Bear stare of love a little bit, right? And for children of the 80s 90s. So there is that. And it's also the rookie mistake. Those people who, they make a good intro for you and then they're like, it's almost like the person who tells the joke and then has a big long pause for you to laugh when it wasn't that funny, you know, like, yeah, technically they made the intro, but it was so transactional and it was so. And they were inserting themselves into it and they were making sure they got their cut and they, you know, it's like those people who, you know, they're, they're so worried about, here's another off putting one and I know we gotta wrap up, but think about here's a big rookie mistake for me. Those people who didn't add to a transaction but want their finder's fee that was never agreed on in advance. You know, they make an intro for you, they didn't sell it. It's like a, and it's often a lower credibility person they happen to be able to introduce you to, they've got nothing to add to the transaction than that you did not have any agreement with them in advance. You go on to start moving towards doing Business and they start ringing up, you know, they start getting demanding about their finder's fee and how, you know, you know, how are you going to take care of me? And like, where did this come from? Like, you know, that is like, oh, I know people who will stop doing a deal because this uninvolved person is demanding the finder fee in the middle of it and it kills the deal. Now you sour both parties, you know. Anyways, I don't know if you got anything to say about that.

Noah Berkson: I've seen that. No, no, I've seen that exact thing happen. Um, and it's, it, it's so funny because that is true. It is always the person that actually doesn't know the person that well, not that much credibility in the situation. And their intent off the bat is how do I make money out of this introduction? Which I just, that's, that's just not the way I operate. The, the one thing I just wanted to add was, you know, I think when I. This has been like a life hack of mine. I, so far this has served me super well. People go, I'll make a bunch of introductions for someone, just try and be helpful. And they go, like, what can I do for like, what can I do for you? Right? And I go, just like one, introduce me to the coolest person you know. Introduce me to the coolest person you know. Like, it's not an industry thing. It's not because they're, you know, they do this specific thing for this specific thing that I'm trying to sell them or anything, like, who's the coolest person you know. And when you start to hang out with a lot of people like you or like anyone in this community, it's like, oh, there's some really cool people. And they go, of course, like, that's all. Oh yeah, please. And so then you start to get this really diverse group of friends and people that you meet and then you're able to continue to do the same thing. And like, it's built some incredible relationships in my life. So I, you know, that's.

Jess Larson: Yeah, you know, I think the other hack too is again playing the long game. You know, real friendships. You know, trust can be lost in an instant. It cannot be gained in an instant. Trust is gained break upon break upon break, right? So it's like you offer to help someone and out of like knee jerk reaction, they say, what can I do to help you? That wasn't like a thought through request on that part. That was like almost a social knee jerk reaction. Don't take them up on it. Do play the long game. Play the long game. Be like, oh, nothing, thank you so much, that's so kind of you to offer. I mean, if I think of something, I'll get back to you. But no, I just wanted to help you. That is one more brick in the trust thing. And then you, let's say you introduce two super high level people or you, you get somebody an investor. You get, I mean, don't get me wrong, if you're a broker dealer and you're in the business of selling investments, take your commission. If you are in the business of selling sponsorships and you get somebody to sponsor, take your commission. That's not what I'm talking about. I'm saying when you're not in the business, when you're not in the business and you happen to make an intro, it works out and they say, don't worry, I'll take care of you. I mean, here's the truth that never happens. They never get around you taking care of you. And two, like, if that's not your business, if that's not your business, you're going to add to the trust wall by putting one more brick on. Like, no, no, no, thank you, that's so generous. That's not what this was for. This was just me trying to help you do your thing. I wish you luck. I hope it works out. There's also the hack too of like, you are now not on the hook to get that transaction to happen. And now becoming a salesperson is something you don't sell. I don't know how you feel about that, but that's the other one of like when they offer to take care of you, I mean maybe some rare extreme situation, you're like, I'm trying to get into that business. But in general, just be like, no, no, this is a generosity thing, not a, not a business thing.

Noah Berkson: But on the inverse of that. I love when things happen and someone introduced it and they don't even expect it. But I know it's like, oh, this would be meaningful to you, like, hey Zeldew, like whatever. And they get a random thing from me and I'm like, hey, thanks so much for, you know, this thing happened. And when you do that, people like, oh my God, now everyone's, you know, they're like, oh, how can I, how can I be so helpful to you sometimes? Which is, yeah, I enjoy the inverse of it. I don't really want to be on the receiving end. I want to be on the giving end.

Jess Larson: Yeah, actually I'll tell you a hero on that because then we've got to wrap up. A hero in that for me is Danny Tango from Orange County. He's a high end CPA to ultra high net worth centimillionaires, billionaires. And my friend, his wealth manager sent him a good referral and his taking care of him was. Danny sent him a $10,000 Rolex because it was a major account and the friend was not expecting it and he will never forget that. Thank you. Guess who's got more referrals after the. And obviously, you know, that's on millions of dollars of business. You know, like it's got to be in, in proportion. But like that is like a truly meaningful, unforgettable gift that is going to pay dividends.

Noah Berkson: It, it is. And just a funny thing on the inverse. Cause I was talking to a friend recently and he, we were talking about someone who'd sold the business recently, made a ton of money and he's like, oh yeah, I referred them to this wealth management group and they put nine, nine figures to this wealth management group. And he's like, they, they, they took me out for dinner and he's like, interesting. Like you're gonna make, you know, million a million plus dollars a year on fees, potentially more on transaction stuff and you take me out for dinner. Like he did. He wasn't asking for anything but then he was like, interesting. And so now he's like, oh, I'm not gonna like, I'm gonna go refer people over to this other place because they just like that was, it was almost insulting. I was like, I would have rather you did nothing for me than be like, oh, let's take you to dinner and we're going to make millions of dollars a year for long periods of time. So it's definitely a balance of figuring that out, but just being aware of it.

Jess Larson: Yeah, totally. Okay, I know we're like 17 minutes over. Give us a website.

Noah Berkson: I could talk to you all day.

Jess Larson: I know. Same here, obviously, which we do all the time. We just don't record it very often. Okay, get rid of the website again and then leave us with a, Leave us with some of the best advice you've ever received.

Noah Berkson: It is. Oh, so the website is outcove.org Best advice I've ever received or I just, I, I think actually. Yeah.

Jess Larson: Nope, go ahead. You got some.

Noah Berkson: I mean, I think it's more, it might be a lesson learned, but just momentum is everything. And I think when you have momentum, you have to you cannot lose momentum. You do everything in your power to not lose it. I think about this in anything in relationships. So, like, just a quick example, maybe that's a good example for this relationships. I'm like, when I meet someone for the first time, there's a very finite period where either we're going to become, like, friends, like, you and I friends, or we're just going to be like, you know, random kind of. We talk if we run into each other at something, and there's a very finite period. So I go, okay, how do I keep the momentum of this up? After the call, I go, okay, what's the plan for me to meet you in person? Right. Oh, I'm going to be traveling here. Where. Where are you going to be? So I'm asking these questions like, oh, okay, like, I'll fly out here. Like, let's get together here. Just trying to. That's the momentum in the relationship. Because once. Once you don't have it. It's the difference between a lifelong relationship and just like a random person you met at a conference, let's say. So it's just. I think everything is momentum. Business is like that, too. Once you lose momentum in anything, it is not fun to try and get it back. So that is. That is my. That is like, my ethos now is just like, momentum is everything. Do. Once you have it, do everything you can to keep the ball rolling.

Jess Larson: Solid. That's a mic drop. Hey, man, thanks again for doing this, Jess.

Noah Berkson: You're awesome. I appreciate you. And we'll talk very soon.

Jess Larson: Bye, everyone.

For 10+ years I've recommended Gusto to founders. I'm an investor in dozens of startups. Many of them use Gusto because I told them to.

The Discovery

Yesterday I discovered something strange. One of my companies stopped operating in November 2023.

• No employees
• No payroll
• No activity

But Gusto kept charging every month. Not only that, the subscription cost kept going up.

Total billed: $3,250.80

The Response

So I reached out to support. They acknowledged the account wasn't being used. Their solution? A "courtesy refund" for 4 months. The remaining $3,000+? Denied.

The reason: "Our terms of service don't allow refunds on active subscriptions."

The Math

Let's think about that. Almost a decade-long customer that would have been a lifetime customer. Dozens of companies referred. Zero payroll activity for almost two years. And the response is still: "Policy says no."

This is the quiet mistake many SaaS companies make. They optimize for protecting $3k today instead of protecting $300k+ in lifetime relationships.

Policy vs. Trust

Good support teams follow policy. Great support teams understand context. Because the real job of support isn't enforcing rules. It's protecting trust.

Ironically, refunding the $3k would have made me more loyal to Gusto. Instead, I'll now be moving companies to Deel for their local payroll and recommending it to future founders.

Moments like this reveal how companies actually think about customers.

The Takeaway

Founders building SaaS: Ask yourself one question. If a loyal customer has a reasonable request, do you want your team to say: "What does the policy say?" Or "What's the right thing to do?"

Throughout my entrepreneurial journey, I've learned that moments like these define company culture. The best career lessons often come from watching how businesses handle the hard decisions.

The bottom line? Short-term policy wins destroy long-term relationships. Great companies know when to break the rules for the right reasons.

Have you found yourself in this type of situation?

Ross didn't win by being the smartest guy in the room. He won by obsessing over control, patience, and optionality. Here's what most profiles won't tell you.

Engineering Leverage

Ross focused on situations where time worked in his favor. He didn't chase deals. He engineered leverage. Long horizons beat fast wins.

Most founders I know are optimizing for the next 12 months. Ross was always playing a decade out. That patience is genuinely rare. And it compounds.

Building Ecosystems

Hudson Yards wasn't real estate. It was retail + office + brand + city politics + timing. Most people buy buildings. Ross built gravity. He built ecosystems, not assets.

That distinction matters more than most people realize. Assets depreciate. Ecosystems appreciate. The value isn't in what you own. It's in what everything orbits around.

Scale Over Perfection

Ross understood that scale forgives mistakes. Small bets require perfection. Big platforms allow iteration.

This is the thing that takes a while to internalize. When you're small, every decision has to be right. When you're big, the system absorbs errors and keeps moving. Building toward scale isn't just about growth. It's about buying yourself room to be wrong.

Offense During Chaos

He played offense during chaos. Economic uncertainty wasn't risk. It was a discount.

The 2008 financial crisis hit real estate hard. Ross kept buying. He understood that the moment everyone else is frozen is the moment the best deals appear. You only get to take advantage of that if you stayed liquid when it felt unnecessary.

The Real Lesson

The lesson I take from his story: wealth at that level isn't about hustle. It's about structure.

• Structure of deals
• Structure of incentives
• Structure of patience

Ross founded Related Companies, a global real estate firm, owns the Miami Dolphins, Hard Rock Stadium, is the majority shareholder in Equinox and has donated hundreds of millions of dollars.

What Founders Can Take From This

You don't need Ross's capital to apply his principles. Three things translate directly to any scale.

Think in ecosystems. Don't just build a product. Ask what gravity you're creating. What adjacent things want to cluster around what you're building?

Stay on offense when everyone else freezes. The best opportunities in your market will arrive during someone else's crisis. If you've spent the good years building resilience, you'll be ready.

And structure your deals so that time is working for you, not against you. The best agreements look lopsided in the short term and obvious in hindsight.

Final Thoughts

Early in my career "structure" would have sounded boring. It feels like in reality to get to his level, it's everything.

It's clear that focusing on the structure of deals and incentives, as well as maintaining patience, are crucial components of his success. You might also find insights in the story of Ben Bergman.

Consider these lessons as you navigate your own entrepreneurial journey.

Meet Lynda Resnick—the marketing genius who turned pomegranates, pistachios, and bottled water into multi-billion-dollar brands that sit in millions of homes worldwide.

I've written more about this in How Stephen Ross Built His Fortune.

From Marketing Agency to Multi-Billion Dollar Conglomerate

Lynda Resnick’s journey didn’t start with inherited wealth or venture capital backing. She began with a small marketing agency, leveraging her expertise in branding and consumer psychology to build what would eventually become The Wonderful Company—a conglomerate that has revolutionized how Americans consume healthy snacks and beverages.

What makes her story particularly remarkable is the consistency of her success across completely different product categories. This wasn’t beginner’s luck or a one-hit wonder. This was a proven, repeatable system for brand building.

The Three Billion-Dollar Brands

Pom Wonderful: Transforming Pomegranates into Liquid Gold

Lynda and her husband Stewart took an ancient fruit that most Americans had never even tasted and turned it into a premium health beverage empire. Pom Wonderful didn’t just sell pomegranate juice—it created an entirely new category in the beverage industry, positioning pomegranates as a superfood before the term became mainstream.

Wonderful Pistachios: Making Nuts Irresistible

The pistachio business demonstrates Resnick’s marketing genius at its finest. She took a commodity product—nuts—and through brilliant branding, celebrity endorsements, and the now-iconic “Get Crackin'” campaign, transformed Wonderful Pistachios into a household name worth billions.

FIJI Water: The $50 Million Acquisition That Became a Billion-Dollar Brand

Perhaps the most impressive feat in Resnick’s portfolio is what she did with FIJI Water. Purchasing the brand for $50 million, she applied the same playbook: premium positioning, strategic marketing, and relentless focus on brand building. The result? A bottled water brand that commands premium pricing and generates billions in value.

Same Operator. Same Playbook. Same Outcomes.

What’s truly fascinating about Lynda Resnick’s success is the consistency of her approach. While the products differed dramatically—from fruit juice to nuts to water—the underlying strategy remained remarkably similar:

• Premium Positioning: Each brand was positioned at the higher end of its category, never competing on price alone
• Health and Wellness Messaging: Every product tapped into growing consumer interest in health-conscious choices
• Bold Marketing: From celebrity endorsements to eye-catching packaging, Resnick understood that great products need great marketing
• Category Creation: Rather than competing in existing markets, she often created new categories where her brands could dominate

The Question of Serial Billion-Dollar Builders

This raises an intriguing question: Who else has successfully built multiple billion-dollar companies from the ground up? The list is surprisingly short. Beyond Brad Jacobs with his serial acquisitions in logistics and Elon Musk’s ventures across multiple industries, few entrepreneurs have demonstrated this level of repeatability at the billion-dollar scale.

What separates these rare individuals from other successful entrepreneurs? It’s not just vision or execution—it’s the ability to identify a proven system and apply it across different opportunities. It’s pattern recognition combined with operational excellence.

Lessons from a Hidden Billionaire

Lynda Resnick’s relative anonymity compared to her achievements offers its own lesson. Not all successful entrepreneurs seek the spotlight. Some prefer to let their brands do the talking while they focus on the work of building.

Her story demonstrates that:

• Branding and marketing can be as valuable as the product itself
• Success in one industry can translate to others when you understand fundamental business principles
• Premium positioning and category creation can be more lucrative than competing on price
• The ability to repeat success is the true marker of entrepreneurial mastery

The Bottom Line

The next time you see Pom Wonderful, Wonderful Pistachios, or FIJI Water in a store, remember: these aren’t just products. They’re case studies in how one visionary entrepreneur turned ordinary commodities into extraordinary brands—not once, but three times.

Lynda Resnick may not have the name recognition of other billionaire entrepreneurs, but her track record speaks volumes. She’s proven that with the right playbook, the same operator can indeed achieve the same remarkable outcomes across vastly different industries.

And that’s the mark of true entrepreneurial genius.

Red McCombs didn't come from money.

Didn't have connections.

Wasn't born into some legacy business.

He started as a car salesman in a tiny Texas town.

Humble Beginnings

But here's where most people underestimate him: He didn't just try to be the best salesman.

He aimed bigger.

He bought the dealership.

Then another.

Then another.

What Made McCombs Different From Other Salespeople

Most salespeople are playing a completely different game. They optimize for the commission. McCombs was always optimizing for the equity.

The difference is not subtle. One makes you good at your job. The other makes you an owner.

While his peers were competing on volume, he was asking a different question: what would it take to own this thing instead of just work here? That question, asked consistently, changes everything.

Building an Empire

By the time people noticed, he'd built one of the biggest auto groups in the country.

But the real upside came from what he did next: He co-founded Clear Channel Communications which grew into the largest radio empire on the planet.

He took it public and later private for almost $19B.

The Move That Changed Everything

The Clear Channel bet was the inflection point. McCombs saw that radio, like auto dealerships, was a business where consolidation would win. Whoever got big first and moved fastest would own the market.

So he moved fast.

It wasn't the most elegant thesis. It was simply: fragmented industries reward the person willing to aggregate them before anyone else decides to. He applied that logic more than once, in more than one industry.

Beyond Cars

He bought the Minnesota Vikings.

Bought and sold the San Antonio Spurs.

Put money into energy, real estate, and early companies before anyone else saw the opportunity.

The Mindset

And the mindset behind all of it?

"If the deal is good enough, you find the money."

No excuses.

No waiting.

Just execution.

Today he's nearly a billionaire twice over.

And still, most people have no idea who he is.

Key Takeaways

Here's what I take from his story:

• Start small, but do not think small.
• Ownership is greater than talent.
• Conviction beats credentials.
• The best opportunities never look "safe" upfront.

Two Paths

Some people need permission.

Others go build things.

Red built his life by choosing the second path.

Conclusion

Red McCombs shows that you do not need pedigree or connections to build extraordinary wealth. You just need to think like an owner, move with conviction, and execute when others wait for permission.

Follow me on LinkedIn or Instagram for more.

They were right about the technology. They were completely wrong about what we'd do with it.

What the Prediction Got Wrong

The machines came. Productivity increased dramatically. The gains were real.

But instead of fewer hours, we raised our expectations. Instead of distributing the abundance, we concentrated it. Instead of a leisure crisis, we got a burnout epidemic. The technology did exactly what they predicted. The humans around it behaved exactly as humans always behave.

We used the productivity gains to do more, not to rest more. We used the communication tools to be reachable everywhere, not to disconnect. We used the information access to make faster decisions, then made more decisions to fill the time we saved.

The predictions failed not because the technology failed. They failed because they modeled technology without modeling human nature.

What Today's AI Predictions Are Getting Wrong

Right now, the prediction cycle is running again. AI will eliminate 40% of jobs. AI will create unlimited wealth. AI will make expertise irrelevant. AI will solve climate change, cure cancer, and end poverty within a decade.

Some of these will be right about the technology. Most will be wrong about the human systems around it.

Here's my read. AI will automate a significant number of tasks, but humans will fill the reclaimed time with new tasks rather than with rest. The people who understand AI will use it to outperform their peers, and the gap between them will widen. Organizations will adopt AI unevenly, with the fastest movers capturing most of the value.

The technology will do what it's designed to do. The question is always: what do the humans around it decide to do next?

How to Think About This Practically

If the 1960s lesson holds, the smart move isn't to predict what AI does to your industry. It's to position yourself on the right side of the productivity gap before it opens all the way.

The people who adopted email in 1993 had a decade-long advantage over people who held on to fax machines. The people who mastered search in 2001 built businesses that their competitors couldn't understand until it was too late. The pattern repeats.

The question isn't whether AI changes your field. It will. The question is whether you're the one using it to go faster, or the one wondering why everyone else seems to be moving at a different speed.

I think about this every week. Not because I have a prediction about where AI lands in 10 years. I don't, and I'm skeptical of anyone who claims to. But I know that the people who engage with it now, who learn its limits and its possibilities through direct use, will have a real advantage over the people who are still reading articles about it in 2027.

The bottom line? The machines are coming, and the predictions will be half right. The technology will do remarkable things. Whether it makes your life better or harder depends almost entirely on what you decide to do with it.

Start doing something with it. Today.

Many are structured like group therapy where you meet once a month for 4 hours and share your business and personal struggles, your highs and lows.

What you end up realizing is that everyone has similar problems. Hearing how others approached them and what they learned can help you navigate your life, relationship and business decisions with much more confidence.

I can say definitively that I wouldn't be where I am today without them.

Some of the most popular ones are YPOhttps://www.facebook.com/EntrepreneursOrganization?__cft__[0]=AZWqI32jqDp1qkbtk7SUHo5NHEaLAdz4Y7Y-RX20XMFPNsZ66XkjGgPLZL4P_OUo53g9G4JrMW7Gpq9uMlI6tYv74LyKjBxW3Mi_7LwCNwLFxQ&__tn__=-]K-REntrepreneurs' Organizationhttps://www.facebook.com/Vistage?__cft__[0]=AZWqI32jqDp1qkbtk7SUHo5NHEaLAdz4Y7Y-RX20XMFPNsZ66XkjGgPLZL4P_OUo53g9G4JrMW7Gpq9uMlI6tYv74LyKjBxW3Mi_7LwCNwLFxQ&__tn__=-]K-RVistage Worldwide

How These Groups Actually Work

The structure is more intentional than most people realize.

You apply. You're vetted. Once accepted, you meet with the same 10-15 people every month for years. No guests. No press. What's said in the room stays there.

Each session typically starts with updates, what's changed since last month, what's keeping you up at night. Then someone presents a real business or personal challenge and the group engages. Not with advice. With questions designed to help you think through it yourself.

It sounds simple. It's incredibly powerful.

The facilitator keeps things honest and moving. The rule in most groups is no selling, no pitching, and no posturing. You're not there to impress anyone. You're there to get better.

What You Get That You Can't Get Anywhere Else

The thing that makes these groups irreplaceable isn't the advice. It's the context.

Your team can't give you completely honest feedback because they work for you. Your investors have their own agenda. Your friends don't always understand what you're navigating. Coaches and advisors can help, but they're not in the arena alongside you.

A peer group of founders at your level? They're in it. They've faced the same hiring decisions, the same cash flow moments, the same relationship strain that comes with building something difficult.

When they tell you "I've been exactly where you are," they mean it. And that changes what's possible in the conversation.

I've gotten more clarity from a single peer group session than from weeks of solo thinking. If you're building something serious and you're not in one of these, put it at the top of your list.

But F1 is different. F1 might be the best networking event in the world for founders and investors.

It's Not About the Racing

Formula 1 races draw a very specific crowd. Not just sports fans. Founders, operators, investors, creators, technologists, builders. People who think at a certain speed and want to be around others who do the same.

At a single race weekend, you can meet someone from Dubai, Singapore, London, São Paulo, and Austin in the same 10-minute span. That kind of density doesn't happen at conferences. It barely happens in major cities.

For me, F1 isn't about the cars. It's about the collisions of ideas that happen off the track.

Why the Environment Works

Most networking events are awkward by design. You're in a room, you have a badge, everyone knows they're there to meet people, and somehow that awareness makes genuine connection harder.

F1 strips that away. You're not there to network. You're there to watch a race. The conversation starts naturally because you're both watching the same thing. The shared experience creates immediate common ground.

There's also something about the pace of F1 that attracts a certain type of person. The sport is about speed, precision, and decision-making under pressure. The people it draws tend to think the same way.

I've had more meaningful conversations at F1 weekends than at most formal business events I've attended. Not because I was working harder at it. Because the environment made it easy.

What I've Learned From Showing Up

A few things I've noticed from attending multiple race weekends:

The paddock access matters less than people think. Some of the best conversations happen in the general areas, at bars near the circuit, or at the dinners and events that happen around the race. You don't need a VIP badge to meet interesting people. You just need to show up and be genuinely curious.

Regulars recognize each other. F1 has a circuit of cities: Miami, Monaco, Austin, Las Vegas, Singapore, Abu Dhabi. If you go to a few of these, you start seeing the same faces. That repetition is how relationships actually form. One conversation rarely changes anything. The fifth conversation with the same person starts to matter.

It's a great equalizer. At F1, a founder with a $2M company might be standing next to a partner at a $5B fund. The shared context makes the conversation easier. Nobody's leading with their credentials. They're talking about the race.

Why I Keep Going Back

I go to F1 for the same reason I build communities. Because the best things in business, in life, and in work happen when interesting people are in the same physical space with a reason to talk to each other.

F1 provides that reason. The racing is the excuse. The people are the point.

The bottom line? If you're a founder or investor looking for a high-signal networking environment that doesn't feel like networking, try an F1 race weekend. Go with an open schedule, stay for the full weekend, and talk to everyone you meet.

You'll be surprised what happens off the track.

Recently, I spoke to students of YPO’ers representing more than 40 countries, each one eager to understand how they can stay relevant in a world transformed by artificial intelligence. Their question was universal, cutting across cultures and borders:

“What human skills will keep us irreplaceable when AI can do so much?”

My answer was simple and powerful:
AI may transform every industry, but it cannot replace the deeply human qualities that drive leadership, innovation, and meaningful impact.

I explore this further in How Stephen Ross Built His Fortune.

1. Emotional Intelligence: The Skill AI Can’t Imitate

During the session, I reminded students that while AI can process data, it cannot understand people.

Human connection—empathy, trust, compassion, intuition—is the currency of leadership.
Students who learn to read others, navigate emotions, and build relationships will rise in every field.

Because people follow people, not algorithms.

2. Critical Thinking in an Era of Instant Answers

AI can give answers. But humans provide judgment.

When information is abundant, discernment becomes priceless.
Being irreplaceable means knowing how to:

• challenge assumptions
• evaluate truth from noise
• see patterns AI cannot see
• make decisions with wisdom, not just information

Critical thinkers will become the “pilots” of AI systems—not passengers.

3. Creativity: The Human Spark That Machines Can’t Create

AI can generate, remix, and analyze. But it cannot originate meaning.

True creativity requires imagination, taste, and a point of view—traits rooted in human experience.
I told the students: “AI can help you create faster, but only you can create something worth remembering.”

Those who combine human creativity with AI’s capabilities will shape industries.

4. Adaptability: The Modern Superpower

In a world moving at exponential speed, the ability to evolve is more valuable than any static skillset.

Adaptability means:

• embracing change
• learning quickly
• staying resilient under pressure
• reinventing yourself continuously

AI accelerates change.
Adaptable humans thrive within it.

5. Ethical Judgment and Integrity

Technology can scale execution, but only humans can make moral decisions.

The future belongs to leaders who use AI responsibly—those who understand impact, fairness, and consequences.
Ethics is not a soft skill; it is a leadership skill.

And it’s one AI cannot own.

6. Communication: Turning Ideas Into Influence

AI can generate words, but humans inspire.

Great communicators—whether in writing, speaking, storytelling, or negotiation—will always stand out.
Students who master the power of narrative will lead movements, mobilize teams, and shape global conversations.

Because influence remains a human art.

A Global Generation with Human Advantage

What inspired me most during the talk was seeing students from 40+ countries ask passionate, thoughtful questions—not about technology, but about purpose, impact, and contribution.

They reminded me that the future is not about machines replacing people.
It’s about people becoming more powerful by leaning into the qualities that make us human.

The Message I Left Them With

AI will make good workers faster.
AI will make great workers unstoppable.
But only human skills make you irreplaceable.

Empathy. Curiosity. Creativity. Leadership.
These are not “nice-to-haves.”
They are the new currency of the world.

And no matter how advanced AI becomes,
these human skills will always set you apart.

Sometimes the Best Ideas Happen Off the Clock

On a quiet morning in Hawaii, the air is thick with salt and sunlight. A group of entrepreneurs, investors, and creatives lace up their shoes and head into the lush green mountains. By mid-afternoon, the same crew might be sprawled across a lanai eating miso black cod, calm music in the background, conversations darting between artificial intelligence, and how to recover from burnout. By midnight, they’re dancing barefoot under the moonlight and swapping stories that will linger longer than any LinkedIn connection.

This is Outcove, the brainchild of serial entrepreneur and investors Jess Mah and Noah Berkson, and it is deliberately unlike any retreat or conference you’ve ever heard of. “I didn’t want to build another soulless networking event,” Mah shared, her tone equal parts conviction and mischief. “we wanted to create a container where brilliant people could drop their guard, play, and actually connect.”

Since its first gathering in February 2025, Outcove has been building a reputation as one of the latest invite-only retreats in the startup world. The event is hosted several times a year – so far, once in Hawaii, once in Park City, Utah – and has become a pilgrimage for founders, investors, and operators searching for something beyond the transactional grind of traditional conferences.

Mah and Berkson call it a “venture camp” for entrepreneurs, startup visionaries and investors. They see Outcove as a blueprint for the future, where the most important deals and ideas will be sparked not by rigid agendas but by genuine human connection. In her eyes, the next era of entrepreneurship belongs to communities that can move fast, build trust and create together, whether it is beside a firepit in Hawaii or carving through Utah’s famous champagne powder.

“My vision for Outcove is simple,” Noah Berkson said. “I want people to walk away feeling more alive, more inspired, and more connected than when they arrived. If we can do that, then everything else – deals, partnerships, even love stories – becomes a bonus.”

The Founder’s Vision for Something Different

Jess Mah’s story begins long before Outcove. She launched her first six-figure business in middle school, went on to co-found more than 10 companies valued in the 9-figures, and built her reputation as one of Silicon Valley’s youngest disruptors. However, despite her success, she found herself restless.

“I was meeting all these incredible people throughout the year – founders, investors, artists, scientists – but our interactions were fragmented,” she explained. “It was coffee here, a rushed dinner there, maybe a Zoom call that felt sterile. I wanted more.”

Berkson shared a similar story, starting and exiting multiple businesses by the age of 32, he still wasn’t finding fulfillment and met many other exited founders who shared the sentiment.

So they built it.

Instead of trying to replicate a formal conference, they set out to design a creative container, something between summer camp and salon, equal parts intimate and electric. “Think of it as if Burning Man had a baby with Davos,” she says, laughing. “But without the desert dust or the pretension.”

That balance – exclusive yet playful, curated but not stiff – is the beating heart of Outcove. The gatherings aren’t monetized or designed to scale. Berkson is clear: this is not a business model, but a passion project.

They referred to it as a “love letter to the community”, something that fills their soul.

The very first Outcove in Hawaii proved the idea had legs. Word of mouth spread fast. The group will reconvene in Park City this winter with a waitlist of entrepreneurs and investors eager to join.

Inside the Outcove Experience

So what actually happens at Outcove? The short answer: a lot….and also not much.

There are no lanyards, no panelists, no rigid agenda. Instead, days are lightly structured around shared activities like group hikes through Hawaii’s cliffs, skiing in the powdery Utah mountains, and communal meals where attendees crowd around long tables piled with local food.

From there, the retreat unfolds organically. Off-the-record discussions emerge around a theme, but without podiums or microphones. Entrepreneurs debate the future of humanity and AI while someone refills smoothie glasses. Founders swap fundraising war stories while enjoying french fries. By night, the focus shifts from dialogue to dance.

“The party energy is not an afterthought – it’s part of the DNA,” Mah said. “When people dance together, laugh together, or sit under the stars at midnight, the walls come down. That’s when the real magic happens.”

One attendee, a fintech founder who later closed a Series A, put it this way: “It doesn’t feel like networking; it feels like summer camp for adults who are making a big difference in the world.”

Berkson doesn’t apologize for blending serious conversations with unapologetic fun. “Life is too short to separate business and play,” he shared with a smile. “Outcove is about designing an environment where people feel alive. And when people feel alive, that’s when they create their best work.”

The vibe is hard to capture in words, but imagine this: one moment you’re perched on a balcony overlooking the ocean, talking about quantum computing with someone you just met. The next, you’re dancing to a live DJ in someone’s living room, barefoot, sweat-slicked, laughing. In between, someone might pull you aside to sketch out a new startup idea on a napkin.

That juxtaposition – serious ideas colliding with joy and chaos – is what gives Outcove its electricity.

They Explains Why It All Matters

For Mah, Outcove is not just about music, meals or mountain air. It is the culmination of more than a decade spent navigating the front lines of entrepreneurship as a young woman in Silicon Valley where she has had to lead teams and enter rooms where she was often the only one who looked like her.

“I have been in boardrooms since I was young,” she said. “I know what it is like to feel pressure to prove myself, to be taken seriously when you are young, female and running a company. That experience made me realize how rare it is to find spaces where people show up as humans first, not résumés.”

For Mah, this is the real return on investment.

“People are hungry for genuine connection,” Berkson added. “Conferences tend to be transactional. Exclusive retreats can feel too curated, almost sterile. Outcove is about breaking both molds. It’s about making space for intimacy and energy at the same time.”

That vision resonates in a startup world increasingly fatigued by “shitty conferences,” as Mah bluntly puts it. “You sit through panels, collect business cards you’ll never use, and fly home drained. I wanted to flip that. People leave Outcove energized.”

It’s not just founders who benefit. Investors who attend often find themselves re-evaluating their own approach to dealmaking and community. “The conversations I’ve had at Outcove shifted how I think about capital,” one investor said. “It reminded me that investing is ultimately about people, not just numbers on a spreadsheet.”

They have no plans to turn Outcove into a brand or franchise, though they hinted at possible future gatherings abroad.

“When you put brilliant, open-hearted people in the same space and let them be human,” she said, “amazing things happen.”

They chased it for freedom.

They did not want to buy more things.

They wanted to buy back their time.

What Freedom Looks Like

To choose who they work with.

To say "no" without fear.

To take a random Tuesday off guilt-free.

To build what makes the most impact, not necessarily the most money.

But it is great when those intersect.

That's the part people don't talk about enough. It's not the yacht. It's waking up on a Wednesday and deciding what matters today. Nobody telling you where to be. Nobody else's priorities dictating your calendar.

That kind of freedom is rarer than money itself.

The Shift

At first, money feels like the goal.

Then you realize it is just the fuel.

The real destination?

Freedom.

I've watched people hit numbers they'd been chasing for years, then immediately set a new number. Not because they needed more. Because they hadn't yet figured out what they actually wanted.

The money didn't bring clarity. It just amplified what was already there.

What the Clearest People Do Differently

The people I most respect figured out the "why" before they hit the "how much."

They got specific. Not "I want freedom" but "I want to be home for dinner every night" or "I want to work on one thing at a time without guilt" or "I want to say yes to the projects that excite me and no to the rest."

That specificity changes how you build. It changes what you optimize for. And it changes what you're willing to sacrifice along the way.

So here's the real question: if money were already solved, what would you be doing with your time?

That answer is worth more than any financial goal.

Conclusion

Money is not the end goal, it is the tool that buys you freedom to live life on your terms.

The most successful people understand that true wealth is measured in time, choice, and impact.

If you want to read more, follow me on LinkedIn and Instagram.

Most life-changing moments do not look like opportunities at first. They look like minor inconveniences.

The Disguise

An awkward invite.

A random message.

A chance encounter.

These are the moments that do not feel significant in real time. They feel like disruptions to your routine, small asks that would be easier to decline.

Three Letters

Whether or not they change your life often depends on three little letters: YES.

That is the difference between the path you are on and the one you could be on.

The willingness to show up when it feels inconvenient.

The choice to say yes when saying no would be easier.

This mindset is why I created Outcove, where connections happen through shared experiences.

A Specific Yes

Years ago, I got an invite to an event I had zero interest in attending. Long drive. Didn't know anyone going. Honestly had a dozen better things to do.

I almost said no. Then I remembered the rule: when in doubt, show up.

I went. Sat next to someone I'd never met. We talked for three hours. That conversation became one of the most important relationships of my career.

I almost traded it for a quiet Saturday at home.

What Saying No Actually Costs You

The problem with no is that it's invisible. You never see what you missed.

You just go about your day, maybe a little relieved, and the potential moment evaporates without a trace. There's no counterfactual. No proof of what could have been.

That's what makes no so seductive. It feels safe. But safety isn't neutral. Every no is also a choice to stay exactly where you are.

Is that where you want to be?

Conclusion

The moments that change everything rarely announce themselves. They show up disguised as minor inconveniences, waiting for you to say yes.

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I will only do first meetings on camera. No exceptions.

Phone calls are completely off the table for initial conversations.

The Connection Factor

Without seeing someone, it is almost impossible to truly connect.

I will even cancel a meeting if someone makes a last-minute request like "can we just do a call?" or "I will be driving."

The difference is remarkable. I cannot count how many times I have jumped on a Zoom with someone I had never met before, and by the end, we are laughing, trading stories, and already brainstorming collaboration opportunities.

That simply does not happen on a phone call.

Visual Impact

When you can see someone's face, everything changes. You can:

• Notice their reactions
• Feel their energy
• Build trust faster
• Understand each other better
• Actually feel the conversation

One call comes to mind. A founder reached out cold on LinkedIn. We had 30 minutes scheduled. She was in Chicago, I was traveling. Ten minutes in, I could tell from her expression that one of my questions had landed differently than expected. I asked about it. That pivot turned into a two-hour conversation and eventually a real partnership.

On a phone call, I would've missed that moment entirely.

Human Connection

Business is still fundamentally human at its core.

Spending 30 minutes seeing the actual person behind the email or LinkedIn profile is always time well spent.

That is why for first meetings, my camera is always on.

Connection beats convenience every single time.

What I Tell Skeptics

People push back sometimes. "It's just a quick intro." "I'm busy, can we just chat?"

My answer is always the same: let's reschedule.

Not because I'm being difficult. Because I know what happens on phone calls. Surface pleasantries. Vague promises to follow up. Then silence.

Camera meetings are different. People prepare. They show up. The conversation goes somewhere real.

Your time is too valuable to spend on connections that never actually connect.

Conclusion

Video meetings create genuine connections that phone calls simply cannot match.

The visual element transforms first meetings from basic conversations into opportunities for authentic relationship building.

Follow me on LinkedIn and X for more content like this.

The Human Advantage

Ironically, I have observed that the biggest competitive advantage in our AI-powered future will be distinctly human skills.

These are the critical capabilities that no AI can truly replicate:

• Leadership
• Creative Thinking
• Change Management
• Curiosity
• Social Influence
• Self Awareness
• Storytelling

What makes these skills so special? They are exactly the things that traditional education often overlooks.

Real-World Impact

Over the past year, I have had the privilege of teaching more than 2,000 students how to become irreplaceable in the age of AI.

It has been the most rewarding experience of my career.

These students are learning to cultivate the human skills that will set them apart in an increasingly automated world.

One student told me her biggest fear was being replaced by a chatbot before she even got her first job. By the end of our time together, she had a clearer sense of what makes her irreplaceable than most people twice her age.

That's what I'm here to build.

A New Educational Paradigm

The traditional educational model needs to evolve to incorporate these essential human skills.

We need to prepare students not just for the jobs of today but for the rapidly changing landscape of tomorrow.

The question remains: What other skills and attributes will give students a true advantage in our AI-powered future?

Building the Relationship Resume

Here's what I tell people who want to start: stop collecting contacts and start building actual relationships.

Make three meaningful introductions this month, not for yourself, but for two other people who should know each other. See what happens.

Show up when it's inconvenient. Follow through when you said you would. Be the person who makes others look good without needing credit for it.

That's what a relationship resume looks like. And it doesn't show up on LinkedIn. It shows up in who calls you when something big happens.

Conclusion

The future belongs to those who can master the art of human connection and relationship building while using AI as a tool rather than fearing it as a threat.

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My Anchor

My center is Soma. Through business pivots, sleepless nights, and moments of doubt, she's been my constant. She doesn't fix the chaos, but she remains present through it all.

Every founder talks about their "why". Mine shows up every day: calm, steady, and real.

Quiet Strength

She's built an amazing career, is literally changing the world through philanthropy, and still makes time to support me. She's the quiet strength behind everything I do.

I've met founders who optimized everything. Sleep schedules. Nutrition. Their calendars down to the minute. And still burned out completely.

The missing variable wasn't productivity. It was someone in their corner who knew them before the company existed.

I explore the dual mindset of building and investing in Investor vs. Founder.

The Real Paradox

Here's what nobody warns you about: the harder you chase the thing you're building, the easier it is to drift from the people who matter most.

Missed dinners. Shortened vacations. Half-present conversations where you're technically there but mentally still in the last meeting. It happens gradually. Then suddenly.

The paradox is this: the people who make your success possible are often the ones who pay the highest price for it.

So who's your anchor? And when did you last tell them?

Conclusion

The entrepreneurial journey is demanding. It can easily consume your time, energy, and relationships, leading to burnout and a sense of emptiness even amidst success. Finding your center is the work that runs parallel to everything else.

Having a supportive partner, friend, or family member who provides stability and understanding can make all the difference. Nurture those relationships. Protect them the same way you protect your calendar.

Who is your center? Take a moment to appreciate the people who keep you grounded.

Thanks for stopping by. You can find me on Instagram, LinkedIn, and YouTube, for more.

His name was William Stanley Jr., and his story is a powerful reminder of what true innovation looks like. He wasn't the kind of entrepreneur we celebrate today.

Here's the full story.

The Engineer

Instead of chasing venture capital or a big exit, Stanley was an engineer focused on a practical problem.

• He didn’t IPO a startup.
• He didn’t live in Silicon Valley.
• He didn't wait for investors.

Stanley was an engineer in the early 1900s, and his approach was grounded in solving a real-world need.

A Simple Solution

In 1913, he invented something simple but revolutionary: the all-steel vacuum bottle.

Before Stanley, thermoses used glass, which was fragile and breakable. Stanley’s idea was to use steel and vacuum insulation. This created a product durable enough for soldiers, railroad workers, and eventually campers. It became known as the Stanley bottle: tough, reliable, and able to keep coffee hot all day.

The Lasting Impact

The crazy part is that he died in 1916, just a few years after inventing it. He never saw the bottle turn into a global brand or the cultural phenomenon it is today.

Stanley didn't become a billionaire, not even a millionaire. He wasn’t even “famous” outside engineering circles. But his simple idea, steel plus vacuum, has lasted over 110 years.

Today the company does hundreds of millions in EBITDA.

Stories of innovation and perseverance inspire my work. See what I’m building on my Now page.

Conclusion

The lesson from Stanley's story is that sometimes, the most enduring legacies come from solving a basic problem better than anyone else. His invention is a testament to the power of focusing on durability, function, and quality over fame or a fast payout.

His quiet invention has created a loud and undeniable impact that continues to grow more than a century later. It proves that real innovation isn't always flashy; sometimes it's just a simple, brilliant idea that stands the test of time.

What problem can you solve today? Follow me on LinkedIn for more content like this.

The Equation

You can either increase your sacrifice or decrease your desires. That's it. No middle ground, no shortcuts, no hacks.

Want a bigger career? More income? A fitter body?

You'll need to increase your sacrifice. More hours learning, more discipline, more sweat.

Want peace of mind? Balance? Contentment? Y

ou'll need to decrease your desires, stop chasing everything, cut the noise, live lighter.

The Problem

Most of us try to do neither. We keep our desires high while keeping our sacrifices low. That's the recipe for frustration.

We want the promotion but won't put in extra hours. We want the fit body but won't give up comfort foods. We want inner peace but keep chasing the next shiny thing.

The Solution

The clarity comes when you decide: Am I willing to pay the price? Or am I ready to lower the demand?

Either choice is valid. You can choose the path of increased effort and sacrifice to get what you want. Or you can choose the path of reduced desires and find contentment with less.

But staying stuck between the two is not an option.

Conclusion

Success isn't about finding the perfect balance or discovering some secret formula. It's about making a clear choice between two paths: increase what you're willing to give or decrease what you want to get.

The frustration you feel comes from trying to avoid this choice. Pick your path, commit to it, and watch how much clearer your next steps become.

The skills that set you apart in this equation are the ones I discuss in The Human Skills That Make Us Irreplaceable.

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This cheat sheet contains 50 bite-sized, high-leverage plays you can use to connect deeper, faster, and more authentically.

These moves would have saved thousands of awkward conversations if someone had shared them years ago.

Before Conversations

• Research their world - know 1–2 things they've done recently
• Lead with context: "I saw your post on X…" beats "Hi, I'm Noah"
• Find a mutual thread - connections, cities, or causes
• Open with curiosity: "What's keeping you curious right now?"
• Have one interesting story, stat, or idea ready

During Conversations

• Ask for stories, not resumes
• Listen for "throwaway" details - hobbies, quirks, side projects
• Ask for opinions, not favors
• Mirror their energy (5–10% warmer)
• Give micro-wins fast—share a book, intro, or resource

Follow-Up Moves

• Send a same-day thank you (personal, not generic)
• Share something tied to your convo
• Add a personal callback ("Hope your daughter's play went well")
• Tag them in a relevant post within 2 weeks
• Make intros proactively

Building Trust

• Check in with no ask
• Highlight their wins publicly
• Defend their name in rooms they're not in
• Be first to congratulate them
• Remember their preferences (coffee order, communication style)

Event Tactics

• Arrive early—easier to meet people
• Connect others first—be the bridge
• Exit gracefully: "I'll let you mingle, but…"
• Anchor near entrances/refreshments
• Be the group note-taker (makes you indispensable)

Digital Moves

• Comment thoughtfully (beyond "Great post")
• DM a compliment - no ask attached
• Use voice notes - more human than text
• Send quick "thinking of you" pings
• Share their work with your audience

Small Gestures

• Intro them to someone helpful today
• Remember dates - birthdays, launches, anniversaries
• Bring a +1 and make them feel welcome
• Send handwritten notes or books
• Offer help outside of work

Mindset Shifts

• Be curious, not impressive
• Play the long game - think in decades
• Value weak ties as much as strong ones
• Treat every interaction as reputation-building
• Leave people better than you found them

Advanced Playbook

• Ask who they want to meet
• Be the connector in your niche
• Host micro-gatherings
• Build a resource library you can share instantly
• Follow up after 6–12 months with something relevant

Power Closers

• End convos at a high point
• Give them an easy out - respect time
• Bring calm, not neediness
• Share the spotlight, don't hog it
• Act like you'll know them for 20 years: it changes your tone

Conclusion

These 50 networking moves focus on building genuine relationships rather than just collecting business cards. The key is consistency and authenticity in every interaction. Small gestures compound over time to create strong professional relationships that benefit everyone involved.

Remember that networking is a long-term game where helping others and staying genuinely curious about their work creates the foundation for meaningful connections. The goal isn't to impress people but to find ways to be genuinely helpful and memorable.

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We talked about a major shift happening in how companies are built, the current AI boom, and why San Francisco is once again becoming the epicenter for entrepreneurs.

Having been both a founder and now an investor with Austin Capital, I've seen both sides of the table, and the changes we're seeing today are unlike anything I have ever experienced.

Keep reading below for a summary of the interview.

Video Gallery

Watch the full interview below, or click here to watch it on YouTube.

A New Model

For a short time, especially around COVID, there was a belief that everything could be done virtually. The idea was that teams could be distributed, and you could get the same work done. While that worked to some extent for certain roles, the current AI boom has changed the game.

The opportunities presenting themselves now are incredible, but they require people to be in person again. We need to be in hubs that have all the tools and resources to build momentum quickly. That is what makes a model like the HF0 Residency so powerful. It is a new way to build companies where founders can lock in for several weeks and accomplish what would normally take two years. It is a fellowship that provides the focus needed to innovate at a rapid pace.

San Francisco's Resurgence

We are seeing a convergence of the digital and physical worlds. This is clear in areas like physical AI and robotics. This shift is bringing people back to key hubs. San Francisco is seeing a resurgence of resources, capital, and talent. If you are building an AI company, this is a better place to be building a business right now.

I think about the influx of resources again, that is investors, that is capital, that is talent. You are starting to see this resurgence of people kind of coming back to San Francisco and I think it is a place to be if you are, especially if you are building an AI company.

Founder-Led Investing

The entire landscape of venture creation and capital has evolved. We have gone from traditional incubators to super angels and micro VCs. Now, we are seeing something even more impactful: founders investing in other founders.

It is great that founders are supporting each other. In probably 8 out of 10 pitches that I see today, the first money in is not from a traditional VC, but from another founder. This is partly because there is more liquidity in the secondary market, allowing successful founders to reinvest in the ecosystem. But more importantly, it creates a network of trust and value-add that is hard to replicate.

The Fintech Opportunity

It no longer costs as much to start a company, thanks to cloud and now AI. This has opened the door for massive disruption, especially in financial technology.

Consider the difference in technology spending:

• JP Morgan: Spent around $20 billion on technology last year.
• Community Banks: The remaining 4,000+ community banks combined spent about $3 billion.

There is a huge gap there. This is an immense infrastructure opportunity. Many community banks are struggling. Their technology is outdated, and they are losing deposits as older generations pass away. They have trouble attracting new customers who expect a modern, digital experience.

This opens opportunities for new companies to provide better services. For example, a farmland marketplace I founded realized that crop insurance was a huge opportunity. We already had the distribution of hundreds of thousands of farmers visiting our site, so we could bolt on this new, lucrative service. Companies that own their distribution can now add financial services on top, creating new and powerful business models.

Events like this align with why I created Outcove, bringing together founders and investors for meaningful connection.

Conclusion

The key takeaway is that we are in a new era of entrepreneurship. It is defined by intense focus, in-person collaboration, and a supportive ecosystem where founders help each other succeed. Models like the HF0 Residency are accelerating this trend by compressing timelines and providing unparalleled resources, making it possible to build faster and smarter than ever before.

This is a once-in-a-lifetime opportunity. The combination of accessible AI, a new culture of wellness and high performance, and the changing dynamics in major industries like finance is creating a new generation of builders. These "tech athletes" are reshaping the world, and it is an incredibly exciting time to be building and investing.

To learn more about how we're supporting the next generation of founders, connect with me and the team at Austin Capital.

The Moment

Somewhere between hiking trails and long conversations with friends, it hit me: this is what all the hard work is for.

Not just the deals closed, the projects launched, or the milestones hit. But the freedom to pause. To enjoy the view. To share the moment with people who matter.

The Why

It's easy to get caught in the grind and forget why we started.

Weekends like this remind me that the why is just as important as the how.

Transformative experiences like this are why I created Outcove, bringing together entrepreneurs for meaningful connection.

What the Mountains Remind You Of

There's something specific that happens when you're surrounded by mountains. Problems that felt urgent shrink. The scope of what you're working on expands. You remember that the thing you're building is one chapter in a much longer story.

I notice this every time. The first few hours are restless. The mind keeps running back to the inbox, the deal, the thing that was due. Then, gradually, it releases. And in that space, I think more clearly than I do at any desk.

Some of my best ideas have come on trails, not in conference rooms. I don't think that's a coincidence.

Why Founders Need to Disconnect Deliberately

Most entrepreneurs I know treat rest as a failure of discipline. They're proud of the unbroken streaks, the 6am starts, the vacation that was really just a working trip with a nicer view.

I used to be that person.

What I've learned is that disconnection isn't a reward for hard work. It's a requirement for sustained hard work. The founders who last aren't the ones who never stop. They're the ones who've figured out how to come back sharper than they left.

Colorado Springs isn't just a place. It's a practice. Find yours and protect it the way you protect your calendar.

Conclusion

This weekend reminded me that all the hard work, all the grinding, all the hustle is about more than just hitting targets and closing deals. It's about earning the freedom to pause, to breathe, and to share meaningful moments with people who matter.

The daily grind has its place, but so does stepping back to remember why we do it all. Find your Colorado Springs and make time for it.

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His name is Harry Stine. He did not build an app, nor did he IPO a flashy startup. He did not even leave his hometown in Iowa, a place with a population of only 6,700.

Keep reading below to know more about Harry Stine and what he does.

Harry Stine

Focus on Seeds

Harry became the richest man in Iowa by doing one thing better than anyone else: Seeds.

Stine Seed quietly licensed genetic technology that made corn and soybeans more productive.

His company’s IP is now used by giants like Monsanto, Corteva, and Syngenta.

In fact, over 30% of all soybeans grown in the world use Stine Seeds.

Owning a Niche

He built a fortune of over $10 billion by picking an unsexy industry and mastering it.

He owned a niche so deep that the biggest players in agriculture had no choice but to license it from him.

Most people are busy chasing headlines, but Harry Stine chased results.

The Lesson

The wild part about his story? 99% of people outside of agriculture still do not know his name.

This teaches a valuable lesson: you do not need to be in a flashy industry to build generational wealth. You just need to solve an ordinary problem in an extraordinary way.

Conclusion

The story of Harry Stine is a powerful reminder that massive success doesn't always come with fame or glamour.

By mastering a specific, essential niche in an "unsexy" industry, he built an empire that quietly powers a significant portion of global agriculture.

His path shows that focusing on tangible results rather than public headlines can lead to incredible, lasting wealth.

It proves that there is immense value in solving fundamental problems better than anyone else.

Remember, quiet industries create loud fortunes.

I share more about what I’m building and investing in on my Now page.

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Here are seven hard-earned lessons that have shaped my career and can help shape yours too.

The Right Rooms

The best rooms change your trajectory.

It's a simple fact that one dinner conversation can be worth more than a year of networking. I've had 20-minute conversations that opened doors I'd been knocking on for years. Most people underestimate how much the room matters and overestimate how much the resume does.

Soft Skills First

Soft skills are more important than hard skills.

AI will eat tasks, but it won't replace connection, trust, and storytelling. The people who will thrive in the next decade aren't just technically sharp. They know how to read a room, inspire a team, and make people feel like they matter.

Play Long Games

Focus on the long term.

Most careers get derailed from chasing short wins. It's better to play long games with long-term people. The best relationships in my career took years to compound. None of them were instant.

Compounding Reputation

Your reputation is compounding.

Every introduction you make, or break, compounds either positively or negatively over time. Do the thing you said you'd do. Be the person people can count on when it's inconvenient. That's how trust becomes currency.

Manufactured Scarcity

Scarcity is manufactured.

Opportunities multiply when you stop waiting to be chosen and start building your own path. The people I admire most didn't wait for permission. They created something and invited others in.

Obsession Wins

Obsession beats talent.

The people who win aren't always the smartest. They are the ones who simply refuse to quit. Consistency over years beats brilliance that shows up occasionally. I've seen this play out too many times to doubt it.

The Biggest Risk

Replaceability is the biggest risk you face in your career.

If anyone can do your job, eventually someone, or something, will. The goal isn't to be good at your job. It's to be the only person who does your job quite the way you do it.

Conclusion

These principles aren't just observations; they are lessons learned through real-world experience and application. They represent a shift in mindset from chasing short-term gains to building a sustainable, impactful career.

By focusing on genuine connection, long-term vision, and irreplaceability, you can navigate the complexities of the modern workplace and build a reputation that truly works for you.

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I'd be smiling but inside I'd be thinking "I'm not good enough" "people don't think I belong up here" "if only I spent more time preparing" — the negative self talk was wild.

I eventually got over it.

In this article are 5 game-changing strategies that helped me overcome my fear and find confidence on stage.

Me on stage

Nerves as Energy

I stopped saying "I'm nervous" and started saying "I'm excited." Same feeling, different story.

This simple mental shift transforms anxiety into anticipation, turning your body's natural response into fuel rather than a roadblock.

Pause Power

Silence feels longer to you than to the audience. But it makes you look confident and in control.

That pause before speaking isn't awkward — it's powerful. Use it to your advantage.

Eyes on Allies

I scan the room and lock in on the people nodding. Speak to them first, momentum follows.

These visual cues become your anchor points, building confidence as you see positive engagement spreading through the audience.

Stories > Stats

Nobody remembers your bullet points. They remember the moment you made them feel something.

Stories create connection where statistics create distance. Lead with narrative, support with facts.

Reps Beat Talent

The only real cure for fear of speaking is doing it… again, and again, and again. Reps beat talent every time.

Each speaking opportunity builds the muscle memory that transforms terror into confidence.

Public speaking is one of the key human skills I discuss in The Human Skills That Make Us Irreplaceable in the Age of AI.

Conclusion

Now? I still have moments of anxiety but when you nail it the energy is intoxicating.

The rush of connecting with an audience, of sharing your message and watching it land — there's nothing quite like it.

If you hate public speaking, don't write yourself off.

Try these shifts — they were a game changer for me:

• Reframe nerves as energy: say "I'm excited" instead of "I'm nervous"
• Pause before speaking: silence makes you look confident and in control
• Eyes on allies: find the nodding faces and speak to them first
• Stories > stats: make people feel something, they'll remember you
• Reps beat talent: the only cure for fear is doing it again and again

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Fast forward: OpenAI's value has surged to an eye-watering $500 billion. Now, just ahead of the GPT-5 launch, Sam Altman drops a bombshell.

"We're awarding a special one-time bonus, vested over 2 years, to around 1,000 employees."

Reportedly $1.5M per employee and in some cases substantially more.

The Numbers

Let that sink in.

Your stock is already life-changing.

Now you get another multi-million-dollar bonus.

You are earning more than many public company CEOs, whose pay often barely crosses seven figures annually.

Game Changed

This isn't just compensation. It's a statement about how intense the AI talent war has become.

When your entry level compensation dwarfs what top executives of public companies earn, you know the game has changed.

I share thoughts on AI and what I'm building on my Now page.

What This Actually Reveals About Timing

The engineer who joined OpenAI in 2022 didn't necessarily know it would become the most consequential company of the decade. They made a bet on a wave that wasn't obvious yet.

That's the part nobody talks about. Not the $1.5M bonus. The decision to join before it was cool.

The biggest career wins I've watched up close all follow the same pattern: someone identified a platform growing faster than the rest of the market and got in early. Not first, just early.

Being right about the direction of a wave matters more than being technically exceptional within a stagnant one.

The Question Every Founder Should Ask

Are you building on a platform that's growing faster than you are?

If you're in an industry that's contracting, even exceptional execution will feel like running uphill. If you're on a rising platform, average execution produces extraordinary results.

The OpenAI engineers didn't create the AI wave. They positioned themselves at the front of it early enough to matter.

What wave are you on right now? And are you near the front?

Conclusion

The AI revolution isn't just transforming technology. It's redefining what it means to be valuable in the modern economy.

OpenAI's unprecedented bonus structure signals that we're witnessing the birth of an entirely new compensation paradigm.

Start building your skills today. The next wave of opportunities is just beginning.

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From "product" at Instacart to helping take ChatGPT from inception to 500M+ users, $13B in revenue, and the 5th most visited website in the world. That's not a career move. That's a career transformation. And it started with a decision that probably didn't look logical on paper.

Logical vs. Leverageable

Most people think about career moves in terms of what makes sense on a resume. Same industry, adjacent role, incremental step up. Logical.

The problem with logical career moves is that they compound slowly. You stay in a lane. You build expertise in a category that might be less relevant in 10 years. You optimize for a version of success that was defined before you had enough information to define it yourself.

Leverageable moves are different. They put you at the center of something that's growing faster than you are. The team around you pulls you up. The problems you work on are the problems that matter most right now. The connections you make are with people at the frontier.

Instacart to OpenAI wasn't logical in 2021. AI assistants weren't mainstream. The risk was real. But it was leverageable. And the difference shows.

How to Find the Leverageable Move

Here's the question I've started asking when I think about career positioning:

What's growing faster than everything else right now, and where can I get a seat at that table?

It doesn't have to be the most prestigious seat. It doesn't have to be the highest-paying one. It has to put you in proximity to the people, problems, and momentum that will matter most over the next decade.

In 2012, that answer was mobile. In 2016, it was SaaS. In 2020, it was crypto and remote work infrastructure. In 2024, the answer is obvious. It's AI.

What Most People Get Wrong About Timing

When a wave is obviously large and obviously real, most people think they've missed it. They haven't. The biggest opportunities in any technological shift come 2-5 years after the initial hype, when the early winners are clear and the real applications are just being figured out.

ChatGPT launched publicly in late 2022. The wave is still forming. The people who position themselves now are not late. They're early for the second phase, which is usually where the real value gets built.

The bottom line? Your next role doesn't have to be the logical next step. It has to put you somewhere that makes your skills more valuable over time, not less. Look for the wave that's actually forming, find a way onto it, and do the work to deserve the seat.

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He paused, looked at me, and said:

"Noah, you're a 9/10 entrepreneur solving a 2/10 problem."

I was stunned. It took me years to understand what he meant.

He wasn't doubting my ability to execute. He was questioning my target. I had picked something I could build, not something worth building.

The Problem

Today, as an investor, I see it all the time: AI-native, Ivy-educated, hustler, hyper-networked founders building slightly better CRMs or launching the 87th "social network for X."

It's not a talent gap. It's a calibration gap.

These are smart people. Driven people. People who could genuinely build almost anything. The tragedy isn't that they can't execute. It's that they've aimed at the wrong target.

A 9/10 founder solving a 2/10 problem will still lose to a 6/10 founder who found a 9/10 problem. Every time.

The Lesson

One of the hardest lessons I've learned: just because you can build it, doesn't mean you should.

The ability to build something is a dangerous thing if you haven't first asked whether it deserves to exist. Execution without calibration is just fast travel in the wrong direction.

The Question

Now every opportunity I evaluate starts with one question: "Is this a problem worthy of my best years?"

It's not "Could I sell this?" But "Would I be proud to have built it?"

Self-awareness is one of the human skills I explore in The Human Skills That Make Us Irreplaceable.

How to Find the Right Problem

I've started asking founders three things before anything else:

First: have you lived this problem? Not read about it. Lived it. The best founders I've backed had scars from the exact thing they were trying to fix.

Second: who else is working on this? If the answer is nobody, that's a warning sign, not a green light. No competition usually means no market, not a blue ocean.

Third: could you work on this for ten years if the money never came? Because the problems worth solving almost always take longer than you think.

Get the problem right first. The execution is the easy part.

Conclusion

Stop building what you can. Start building what you should.

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I travel a lot, both for work and for adventure. While every trip is unique, there are a few places I return to or that have left an indelible mark.

Here are three destinations that offer the perfect blend of work, inspiration, and escape.

Japan

Every year, I head to Niseko in Japan to snowboard. It's a non-negotiable trip that serves as a physical and mental reset.

It's my annual pilgrimage for pure, exhilarating fun with other entrepreneur friends.

What I didn't expect the first time was how much the culture would affect me off the mountain. Japan runs on a different set of values. Precision. Craft. Long-term thinking. You see it in the food, the trains, the way strangers interact with each other. I always come back with something I can't quite name, but it shows up in my work for months afterward.

Snowboarding

South Africa

My trip to the Sabi Sabi private game reserve in South Africa was truly incredible.

Spending days on a safari, completely disconnected from the digital world and immersed in nature, is a powerful experience.

There's no cell service on the game drives. No Slack. No email. Just the guide, the vehicle, and whatever is on the other side of the bush. I didn't realize how much mental noise I was carrying until it went silent. By day two I was sleeping better than I had in years.

Argentina

I travel to Argentina multiple times a year, as it's home to my tech team. While it's a work trip, it's also an opportunity to immerse myself in the vibrant culture of Buenos Aires.

Many of my favorite destinations have become venues for Outcove, where I bring together entrepreneurs for transformative experiences.

Blending strategic work sessions with exploring a different way of life provides a unique kind of energy and inspiration that you can't get from a Zoom call.

Buenos Aires specifically has a pace to it that I find genuinely restorative. Late dinners. Long conversations. A city that doesn't seem to be in a rush even when it's fully alive. Working there feels different from working in New York or Miami. Something about the environment changes how I think about long-term bets.

Walking around

How I Travel

A few things I've learned from years of traveling as an entrepreneur.

No work on the first full day. I used to arrive and immediately check in. Now I give myself at least one day to actually arrive before the laptop comes out. The transition is worth it.

Bring a notebook, not just a phone. There's something about writing by hand in a new place that surfaces ideas I don't access at a desk. I have years of notebooks filled with things I figured out somewhere I'd never been before.

Travel with people who challenge you. The conversations are the point. The destination just creates the context.

Conclusion

Travel, whether it's for adventure, work, or relaxation, is a crucial investment in yourself.

It breaks routines, sparks new ideas, and provides the perspective needed to tackle big challenges.

This isn't just about software; it's about creating an ecosystem for efficiency.

Here are the five key tools that form my daily tech stack.

AI Meeting Scribe

Bee is a game-changer. It's an AI wearable band that captures and transcribes every meeting I'm in.

More importantly, it automatically identifies and creates action items and tasks.

This eliminates the need for manual note-taking and ensures nothing falls through the cracks post-meeting.

Email Management

I use Superhuman for my email. It’s built for speed and helps me get through my inbox in a fraction of the time it used to take.

Its keyboard-first design and minimalist interface mean less time managing email and more time doing deep work.

Email Assistant

Working alongside Superhuman is Howie. It functions as my personal AI email scheduling assistant.

It's another layer of leverage that keeps my inbox from becoming a time sink.

Relationship Hub

For managing my network, I use Clay. It’s less of a traditional CRM and more of a personal relationship manager. It automatically pulls in information from my calendar, email, and social media to give me context on everyone I know.

For an investor, your network is everything, and Clay helps me maintain it.

Browser

My browser of choice is Dia. It's a new, minimalist browser designed for focus and productivity.

It strips away the distractions and clutter of traditional browsers, making it easier to concentrate on the task at hand.

I share more about what I’m working on and the tools I use on my Now page.

Conclusion

My philosophy is simple: leverage technology to buy back your most valuable asset—time.

Here’s a quick rundown of my tech stack:

• Bee - AI wearable band for meeting transcription and automatic action item creation
• Superhuman - Speed-focused email client with keyboard-first design for rapid inbox management
• Howie - AI email scheduling assistant that prevents inbox overload
• Clay - Personal relationship manager that automatically pulls context from calendar, email, and social media
• Dia - Minimalist browser designed for focus and productivity without distractions

By automating and optimizing routine tasks, you create more space for creativity, strategy, and growth.

This sentiment is not isolated to the youngest generation of adults. A feeling of financial unease is growing, presenting significant challenges for individuals and employers alike as they navigate compensation and financial well-being.

The Data

A staggering 77% of U.S. adults reported feeling financially insecure in a May survey from Bankrate. This highlights a continued rise in financial anxiety that has been building since 2023. This widespread insecurity reflects a troubling national mood regarding personal finances.

More than one-quarter of the 2,260 respondents stated they would need to earn $150,000 or more annually just to feel financially secure and comfortable. This figure is a stark contrast to reality for most Americans.

The Widening Gap

The desired income for security is nearly double the average full-time salary in the U.S. for 2023, which was $81,515, according to data from the U.S. Bureau of Labor Statistics (BLS) cited by Bankrate. The massive gap between the salary needed to feel stable and the average national income underscores the financial pressures many households face.

Bankrate pointed to the ongoing erosion of purchasing power by inflation as a primary cause. Referencing Consumer Price Index (CPI) data from the BLS, the company showed that $100,000 in January 2020 had the same buying power as $124,353 in April 2024. This consistent decline in the value of a dollar makes saving and financial planning feel like an uphill battle.

Key Takeaways

• Generational Despair: A Credit Karma report finds that 49% of Gen Z believes saving for the future is pointless.
• Widespread Insecurity: A majority of American adults (77%) feel financially insecure.
• The "Security" Number: Over 25% of people feel they need an income of $150,000 or more to be financially comfortable, nearly double the national average.

Inflation's Impact: The purchasing power of money has significantly decreased, with $100,000 in 2020 being equivalent to over $124,000 just four years later

I explore both the founder and investor perspectives on wealth-building in Investor vs. Founder.

But jokes aside, this is actually happening. The AI talent war is unlike anything I've seen in 15 years of building companies. Big Tech isn't just competing for good engineers anymore. They're offering packages that make startup equity look like a rounding error.

What's Actually Going On

Meta, Google, and OpenAI are paying AI researchers $1M+ in annual compensation. Some top ML engineers are pulling $5-10M when you factor in RSUs and retention bonuses. These aren't rumors. These are real numbers circulating in the founder community.

And yet, somehow, some of the best AI engineers in the world are still choosing startups. Why?

Because money isn't the whole story. It never is.

What Startups Actually Have

The engineers joining early-stage AI companies aren't leaving Meta money on the table because they're bad at math. They're making a different calculation.

At a big tech company, you're one of 10,000 engineers. Your work ships into a product used by billions, sure, but your fingerprint on it is almost invisible. The decisions get made three layers above you. The interesting problems get solved by a committee.

At a startup, you own the problem. You make the calls. You see the impact in real time.

That's not a consolation prize. For the right person, it's worth more than the bonus.

What This Means for Founders

If you're building an AI company right now, you can't win on salary. You won't. So stop trying.

What you can win on:

• Ownership. Real equity at a real valuation, not 0.1% at a company already worth $50B.
• Mission clarity. Engineers want to know exactly what they're building and why it matters.
• Speed. At a startup, you can go from idea to shipped in a week. That's addictive for people who build.
• Access. Working directly with the founders, making decisions that actually stick.

The engineers you want are already thinking about this trade-off. Your job is to make the case clearly and honestly.

The Honest Truth

Most founders pitch the dream without acknowledging the risk. That's a mistake. The best AI engineers are sophisticated. They know the failure rates. They know the dilution math. They've seen the cap tables.

Be straight with them. Here's the risk. Here's the upside. Here's why we think this works. Here's what you'll own and what you'll build.

That conversation wins more often than you'd think. Especially when the alternative is getting lost inside a $1 trillion company.

The bottom line? You probably can't poach someone who just got a $100M signing bonus. But you don't need to. You need the person who turned it down. Those people exist. Go find them.

In just 5 years, her company scaled from $0 to $1B+ in ARR.

What I witnessed next revealed everything about what separates billion-dollar founders from the rest.

Always Selling

I watched as she met person after person, always asking two questions:

• "How many employees do you have?"
• "Would you consider a new payroll provider?"

If the answer was yes, she'd get their number and say, "I'll text you — let's get time on the calendar next week."

The Surprise

I was stunned.

I asked her: "Wait... how many people are on your sales team?" — thinking it must be tiny if she's doing direct outreach herself.

She smiled: "1200."

That's when it clicked.

The Difference

She didn't need to sell. She wanted to.

Because founders like her don't waste opportunities. They create them.

I share more about what I'm building and investing in on my Now page.

What I Noticed in the First 5 Minutes

Before the selling started, I noticed something else. She was fully present in every single conversation. No phone. No scanning the room for someone more important.

She made eye contact. Asked follow-up questions. Remembered names from people she'd met 20 minutes earlier.

That's not a tactic. That's a default setting. And it's rare.

The Pattern Across Every Unicorn Founder I've Met

I've now had the chance to spend time with quite a few founders who've built at scale. A few things keep showing up.

First: they never stop being the best salesperson in the room, even with 1,200 on the team. They understand that the founder's pitch is different from any rep's pitch. It carries weight no one else can replicate.

Second: they treat every room like there's a deal in it. Not out of desperation. Out of genuine curiosity about what people need.

Third: they play a different time horizon. While most people are thinking about this quarter, they're thinking about what this conversation could become in three years.

Is that level of sustained hunger something you can build, or is it something you're born with?

Conclusion

This is how you build a $1B company in five years.

While others delegate and distance themselves from the front lines, unicorn founders stay hungry. They see every conversation as a potential door to their next big break.

Follow me on LinkedIn for more content like this.

This summer I'm looking forward to making it a more regular occurrence with Redefining Creativity: Designing Human Connections In an AI World led by Rebeca Hwang.

The Shift

AI is fundamentally changing how companies hire.

There was a time when your resume was your most valuable asset. Good grades, a solid degree, a respected job title — these were the golden tickets to a stable future.

But that world is gone. In its place is something more volatile. More confusing. And, ironically, more human.

Teaching the next generation is central to my work on The Human Skills That Make Us Irreplaceable in the Age of AI.

What I Talk About With Stanford Students

I always start with the same question: "How many of you are worried AI will take your job?"

Most hands go up. Then I ask: "How many of you are actively building the skills that AI can't replicate?"

Almost no hands.

That gap is exactly what we spend the session on. Leadership. Storytelling. Social influence. Change management. The skills that compound over a career and don't show up on any technical spec sheet.

I tell them: the resume isn't dead. But the skills that back it up have completely changed. A Stanford degree opens the door. What happens in the room depends on things they didn't teach you in class.

What Surprises Me About This Generation

These students are sharper than I expected and more anxious than they let on.

The questions they ask backstage, after the lecture, are the ones that actually matter. Not "what should I major in?" but "how do I figure out what I'm actually good at?" and "how do I get into rooms I wasn't invited to?"

Those aren't academic questions. They're real ones. And they're exactly the right ones to be asking at 21.

The best students I've met at Stanford aren't the ones trying to become irreplaceable someday. They're the ones already acting like it.

Conclusion

I'm looking forward to sharing how to use human relationships to become Irreplaceable in an AI world.

Follow me on LinkedIn for more content like this.

The Setup

In one of my first businesses, we were almost out of money. An investor who had been stringing us along for months invited us to a steak dinner to discuss the terms of his investment.

We never would have chosen this restaurant, and my partner and I tried to order the cheapest thing on the menu.

Red Flags in Plain Sight

The evening should have been a celebration of our upcoming partnership. Instead, it became a masterclass in recognizing red flags.

While we carefully selected the most affordable options, conscious of our dwindling funds, our potential investor showed no such restraint.

Looking back, there were signs long before the dinner. Follow-ups that went unanswered for weeks. Last-minute cancellations with no explanation. Vague answers every time we pressed for a timeline.

Each one felt excusable on its own. Busy schedule. Competing priorities. But together? They were telling us exactly who this person was.

We just weren't listening.

Moment of Truth

When the bill came, the investor said, "How do you wanna do this?" dropped a $50 bill on the table, and left in his $200,000 car.

His steak alone was $49.99.

Unsurprisingly, he never invested in our company.

Resilience in the face of rejection is one of the human skills I discuss in The Human Skills That Make Us Irreplaceable.

How to Read the Room Earlier

Now I watch for signals before any dinner happens.

How someone treats the waiter. Whether they make eye contact or spend the meal scanning the room. How they talk about the last deal that fell apart, the last founder they passed on.

And this: do they ask about you, or do they just perform interest?

There's a difference. You can feel it. Real interest has follow-up questions. Performed interest has a tell: the pivot back to themselves, every time.

I do most of my reading in the first five minutes now. Not the pitch. The handshake. The small talk before anything is at stake. That's when people are most themselves.

What signals are you still ignoring?

Conclusion

This experience taught me that some rejections are protection in disguise. The investor who seemed like our salvation would have likely brought more problems than solutions.

In fact, a couple of years ago, I saw an article about him being sued by the federal government for massive tax fraud.

In that moment, everything clicked into place. What had felt like rejection was actually protection.

The bottom line? Not every open door is worth walking through. Some closed doors are the universe doing you a favor.

If I could identify the single most important piece of advice I've ever received, it would be this: If other people's expectations of you are higher than your own, you're probably not in the right job.

This simple truth cuts to the heart of what separates exceptional performers from everyone else. It's not about meeting external standards—it's about creating your own.

Kobe Bryant Standard

In an interview, Kobe Bryant was asked:

"Do you ever feel the pressure of millions of fans' expectations?"

His response was revealing:

"No. Not even a little. Because the expectations I place on myself are far greater than anything anyone else can ever place on me."

That's not arrogance. That's ownership.

What Sets Great Performers Apart

The greatest performers—on the court, in business, in life—don't outsource pressure.

They internalize the standard. They raise the bar above what anyone else would ever dare to ask of them. And then they live there.

This has nothing to do with basketball. It's about leadership. It's about accountability. It's about greatness.

Transcending External Pressure

Pressure isn't something you feel when you're chasing someone else's expectations. It's something you transcend when you set your own.

When you operate from this mindset, external pressures become irrelevant.

Setting your own expectations is a crucial skill I explore further in The Human Skills That Make Us Irreplaceable.

The noise of critics, the weight of others' opinions, the fear of disappointing people—all of it fades into the background because you're already holding yourself to a higher standard than anyone else could imagine.

Conclusion

The path to greatness begins with a simple shift: stop looking outward for validation and start looking inward for motivation.

When your internal standards eclipse external expectations, you don't just meet success—you define it. The question isn't whether you can handle the pressure others place on you.

The question is whether you're brave enough to place even greater pressure on yourself.

This is the story of how Jim Simons and his team of scientists created returns so extraordinary that they eventually stopped accepting outside money.

Fund That Defied Belief

This fund made so much money, they had to start giving it back. Not to investors—to themselves. Because external investors weren't even allowed anymore.

Why? Because Medallion, the flagship fund at Renaissance Technologies, was compounding at over 66% annual returns before fees. For decades.

Let that sink in. Wall Street thought it was a myth. But it was real.

The Unconventional Founder

It was built by a retired math professor named Jim Simons—not a banker, not a trader, not a finance guy. The craziest part? Jim Simons didn't start Renaissance until he was 40 years old.

A Different Approach

He hired physicists, codebreakers, astronomers—people who didn't think like Wall Street. They didn't guess. They didn't bet on vibes. They let the data speak. And it didn't whisper—it screamed alpha.

The Numbers

In the 2000s, Medallion made more profit in one year than most funds make in a decade. Over 40% of Renaissance staff held PhDs. Simons eventually closed the fund to outsiders so his employees could keep the profits.

I share more about investing approaches on my Now page.

While others pitched vision, they printed returns.

The craziest part? Jim Simons didn’t start Renaissance until he was 40 years old.

The Medallion Fund stands as perhaps the greatest example of what's possible when you replace Wall Street's traditional approach with pure scientific rigor.

As I've been writing my book on human relationships and networking in the age of AI, and through countless conversations with parents about future-proofing their children, a clear picture of our evolving professional landscape has emerged.

Why STEM Isn't Enough Anymore

The World Economic Forum projects that by 2030, the most valuable abilities will be adaptability, creativity, emotional intelligence, and leadership—precisely the "soft skills" that traditional education often overlooks.

Meanwhile, science, technology, engineering, and math skills, while still important, won't hold the same currency that they do today.

This creates a striking paradox.

Parents are investing heavily in getting their kids into the best STEM programs, yet by the time these children enter the workforce, those traditionally prized technical skills may not be the ultimate differentiators we thought they were.

Traditional STEM expertise still matters, but as AI turns technical know-how into a commodity, the human traits that can't be automated take center stage.

When anyone can ask an AI model for the right answer to complex problems, people will choose to work with humans they genuinely like and trust.

Reality of the AI Job Market

My personal outlook on the immediate future of the job market is quite stark.

We're already seeing hiring freezes and increased layoffs, and this is before AI has been integrated at any significant scale across industries. I genuinely believe we could see over 50% of current jobs becoming obsolete within the next five years.

Consider the current hiring process: it's not uncommon for a single job posting to attract a thousand or more applicants.

As AI automates more tasks, available roles will likely shrink, intensifying this competition exponentially. Companies like Shopify have already stated they won't hire a person if AI can do the job effectively.

For the first time in modern history, humans must justify their value proposition against technology. The core issue is that AI levels the playing field for intelligence.

With tools like ChatGPT and other language models, specialized knowledge alone ceases to be the ultimate differentiator.

Your Network Is Your Net Worth

If intelligence becomes a commodity, what becomes our unique advantage? I firmly believe it's our ability to connect with other humans.

People want to work with people they like and trust. Therefore, teaching kids how to build and nurture authentic connections is the highest-leverage investment a parent can make.

Relationships—not résumés—become the ultimate advantage in this new landscape.

Essential Skills Needed

When intelligence is commoditized, these specific relationship muscles will separate thriving professionals from the obsolete:

Craft a Compelling Origin Story

Most people struggle to articulate what makes them unique and interesting.

People decide in seconds whether they want to keep listening, so you need a story that sparks instant interest and hints at the unique value you bring.

Are you disarmingly witty? A pattern-spotting expert?

Do you have a genuinely captivating smile? Pinpoint the trait others consistently appreciate and let it shine in every interaction. People want to hire and work with individuals they find genuinely interesting, not just technically competent.

Ask Questions That Create Connection

Instead of the tired "What do you do?", try "What's giving you the most energy right now?" Thoughtful prompts that unlock emotion generate memorability and genuine rapport.

People enjoy talking about themselves, and if you can be skilled at asking the right questions, you don't even need to talk much—people will naturally like you more.

Become Unforgettable

Use contrast, vivid detail, or unexpected anecdotes. Psychology shows that distinct moments etch deeper into memory than a string of polite facts.

Understanding the storytelling tactics and psychological principles that make people remember you is crucial for long-term success.

Curate a Diverse Network

A closet full of identical shirts is useless. Likewise, you need contacts from varied backgrounds, industries, and viewpoints to unlock real opportunity.

Avoid surrounding yourself only with people similar to you—true strength comes from a network rich in varied experiences and perspectives.

Engineer Serendipity

Great breaks often hinge on being in the right room at the right time. Map out events, forums, and online communities where chance collisions are most likely.

The best networking opportunities feel like serendipity, but you can actively increase these possibilities.

Think Like a Generalist

Know a little about a lot so you can relate to anyone. A shared hometown, mutual sports allegiance, or niche hobby reference can ignite rapport instantly.

When you can relate to someone in any way—even through small commonalities—it unlocks significant trust and connection immediately.

Maintain Relationships Strategically

Proactive check-ins, thoughtful articles, and well-timed introductions keep you top of mind. There's a specific rhythm to staying relevant without feeling transactional.

Building connections is just the start—develop a strategy for following up and staying memorable so people think of you when opportunities arise.

Create Value Through Introductions

A great introduction frames the benefit for both sides, provides concise context, and makes it effortless for people to say "yes."

Learn how to make thoughtful connections between your contacts and offer insights that provide genuine value.

Master this, and your network compounds automatically.

Build Your Relationship Flywheel

Develop a systematic approach for outreach, follow-up, authentic compliments, and—crucially—learning how to ask for favors appropriately.

Most people either never ask for help or ask too aggressively too soon. There's a strategic middle ground that builds relationships while advancing your goals.

Teaching These Skills

Parents can start developing these crucial abilities immediately:

Storytelling at the dinner table: Encourage children to recount their day with color and emotion so they practice holding attention and crafting compelling narratives.

Question swaps: Replace "What did you learn in class?" with "What was the most surprising thing you heard today?" to build curiosity and conversational agility.

Micro-leadership moments: Let them organize a family outing or negotiate weekend plans. Real-world practice beats any textbook when it comes to developing leadership and negotiation skills.

Rethinking Extracurriculars

Competitive sports can teach discipline and teamwork, but daily three-hour practices rarely compound into future career value.

I would strongly advocate redirecting some of that time toward debate clubs, improvisation workshops, or community projects where empathy, communication, and initiative are on full display.

The statistical reality is harsh: almost no one becomes the next Tiger Woods or professional athlete.

Yet families continue investing countless hours pursuing athletic achievements that provide minimal career advantage when those hours could develop skills that will actually differentiate them in the future job market.

Strategic College Planning

If your child can earn a spot at a truly elite university—Harvard, Yale, Princeton, and their peers—the network alone often justifies the tuition.

These institutions offer one irreplaceable asset: access to relationships with future leaders and decision-makers.

Otherwise, freed-up resources may be better spent on targeted courses, travel, and relationship-building experiences that cultivate the skills AI can't replicate.

If you can't gain admission to tier-one institutions, it's worth critically evaluating the traditional four-year college path against other avenues, especially considering the financial burden.

Embracing Realism

Parents need to have honest, pragmatic conversations with their children from a younger age about career prospects and financial realities. This doesn't mean crushing dreams, but it does mean providing clear-eyed analysis.

I often share the story of a father whose son dreamed of being a soccer coach.

The father didn't crush the dream but instead walked his son through the financial realities—salary expectations versus cost of living and desired lifestyle.

This pragmatic approach helped his son realize the path wasn't feasible for the life he envisioned.

The window to easily pivot careers later in life is narrowing rapidly.

Helping children gain clarity on their interests and potential paths earlier, while still fostering adaptability, will serve them well in an increasingly competitive landscape.

Leveraging AI as a Tool

While AI presents challenges, it's also a powerful tool when used correctly.

I advise people to use it as a "thought partner" or "sparring partner"—engage with it, bounce ideas off it, and have conversations back and forth rather than just asking for completed work.

A key skill now is learning how to prompt AI effectively. If you can clearly articulate your needs to get the desired output on the first try, that's a significant advantage.

However, the goal is to augment your abilities, not become overly reliant and lose your capacity for independent thought.

The Path Forward

In a future where technical prowess can be replicated by machines, our humanity will be our greatest asset.

The ability to connect, to be genuinely liked, to bring diverse groups together, and to add unique human value will be what sets individuals apart and ensures their place in an ever-changing world.

The professionals who thrive won't necessarily be the smartest in terms of raw intelligence—they'll be the ones people want to work with, learn from, and build lasting relationships with.

I explore the dual mindsets of building companies and evaluating investments in Investor vs. Founder.

Start developing these skills now, both for yourself and your children. The future belongs to those who master the art of authentic human connection.

At 31, I've been fortunate to achieve several eight-figure exits, build a diverse portfolio spanning fintech and financial services, and develop a reputation as a connector.

My story weaves together gritty sales experience, strategic fundraising decisions, and an almost obsessive commitment to relationship-building—all framed by my mantra of being "long-term greedy."

As Managing Partner of Austin Capital Partners, I've learned some hard lessons about the realities of building companies worth millions and discovered counterintuitive approaches that have fueled my success.

Video

Watch the podcast on YouTube here.

Or watch it below:

10 Key Takeaways

Here are some key takeaways from my discussion with Jess Larsen.

Rejection Is Your MBA

Door-to-door security sales in Cedar Rapids, Iowa, became my entrepreneurial foundation. "You just get rejected all day for a living. You start to really embrace rejection and start to really like it, and it's like a game. How do I overcome this?" This resilience transformed rejection from a barrier into a competitive advantage throughout my career.

Serial, Sector-Hopping Works

I've launched or scaled businesses in LinkedIn-style networking software, health-tech (340B compliance), drone-based property analytics, near-shore engineering staffing, and a Zillow-for-farmland marketplace called Common Ground. My success across disparate industries demonstrates that transferable execution skills often beat deep single-sector expertise.

"Unsexy" Businesses Can Create Massive Value

My near-shore engineering firm focused on Latin and South America grew fastest and produced an eight-figure exit—proof that "unsexy" labor-arbitrage models can mint cash, especially during the zero-interest-rate period of 2019-2021. "We're staffing these people. Right. It's a labor arbitrage. And they're really good cash businesses. They can be tremendous cash businesses."

Prep for Diligence Before You Need It

I learned the hard way that exit preparation should begin on day one. "You start out with this idea of building a business... But you don't do any of the things that you would need to do to sell that business." When buyers request 120 diligence items, sloppy contracts and missing records invite "deal fatigue" that private equity firms tactically exploit: "I think now understanding from the private equity side how you think about that... that's all kind of part of the playbook."

Avoid Arbitrary Fund-Raise Targets

A common mistake I see is entrepreneurs raising capital without strategic milestones: "They say, 'Hey, I need to go raise this much money' without really realizing: is that amount of money going to get you to where you can raise more money?" Many startups raise $3M because "that's what people do," only to burn it in 12 months without achievements that support the next round.

Bootstrapping Buys Optionality

Owning 100% of a $30-100M outcome can beat swinging for a billion with VC strings attached. "When you bootstrap, your options are great. Generally, if you have a good business, you can find a buyer who's excited." In contrast, venture-backed founders face a binary outcome: "Are you joking? We signed up for this to be a one or a zero—it's either a billion-dollar business or it's nothing." This creates "founders who are entirely unmotivated and completely burnt out, but forced to drive toward an outcome that candidly probably won't happen."

View Investors as Partners, Not ATMs

I emphasize building authentic investor relationships through transparency: "I think being able to tell a story and being realistic is important... Here are all the challenges in this business, here are all the headwinds we're facing." This approach cultivates allies who step up during crises—as when one investor wired an eight-figure rescue check overnight during a business emergency.

Lead With Value in Networking

With ultra-high-net-worth individuals and family offices, my rule is simple: "I want to add value right away... I want to have my relationship bank account and I want to be the person that's like, I can provide you so much value. I'm not going to ask for anything." My primary currency is connections across diverse industries: "Oh, someone has a random... What are you working on? Oh, we have this nonprofit where we're funding, like, bees. Oh my God. Actually, I know the perfect person you've got to talk to."

Momentum + Systems = Relationship Capital

I believe initial interactions must build immediate momentum: "You and I hop on a call and we have a good conversation, and then I can either say, 'Yeah, cool. Let's chat sometime, keep in touch.' And that relationship is probably never going to be close." Instead, I make immediate plans or introductions while maintaining a sophisticated system to track follow-ups.

Be "Long-Term Greedy"

Quick money quests often backfire. "When you're like, how do I make money as quickly as possible? That doesn't go well. But really looking at things in a much longer time horizon." This patient approach guides calmer decisions and prevents the FOMO that drives poor choices: "When you're younger... you go, well, you have all these things like, why don't I have that?... I think that can make you make very short-term decisions that aren't going to be very optimal for the long term."

Beyond LinkedIn Connections: Redefining Network Value

I've come to believe that "your network is valued not by the number of people in it, but by the number of people that know each other because of you, that wouldn't have met otherwise."

This perspective has shaped how I approach both my podcast and conference initiatives.

For my upcoming Park City conference and new "Dose of Greatness" podcast with Jeff Ma, I wanted to create spaces for authentic connection.

I saw a gap in the market between typical business conferences with "great people you might want to do business with" but stale content, and more experiential events where "the people are often a little bit too woo-woo."

The goal is to bring together "really incredible people where you're also able to have fun together" because "the bonding comes from doing things that are fun, not from sitting there listening to a speaker."

Similarly, with the podcast, I want to move beyond success stories to explore the human dimension: "There's a lot of podcasts out there that we like, but a lot of it, there's not a whole lot of vulnerability."

The format aims to ask the questions that rarely get addressed: "You've made all this money, but are you actually happy?"

I explore the different mindsets required for building versus investing in Investor vs. Founder.

Conclusion

My career is less a straight line and more a series of compounding relationship loops: each venture, exit, or introduction layers onto the next.

From door-to-door sales rejection to eight-figure exits and building a sophisticated family office platform, my journey demonstrates the power of embracing challenges, building genuine relationships, and maintaining a long-term perspective.

As business environments become increasingly transactional, I've found success through emphasizing authentic connection and strategic patience.

For entrepreneurs navigating their own journeys, I believe sustainable success comes not just from raising capital or achieving exits, but from creating a web of meaningful relationships that provide both personal fulfillment and business advantage.

If you borrow nothing else from my playbook, remember this dual approach: master rejection early, then play the longest game in the room.

Being "long-term greedy" isn't about delayed gratification—it's about building something that creates enduring value for everyone in your network.

Transcript

Here is the transcript:

Jess Larsen: Welcome to Innovation and Leadership. I’m Jess Larsen. On this episode, we get to have Noah Berkson. We’re going to hear about his big exits as an entrepreneur, working with funds, the family office, the Weekend of Man, his new podcast, and a lot of fun things. Noah, thanks for doing this. And how do you introduce yourself when people ask what you do?

Noah Berkson: Thank you so much for having me, Jess. You know, it’s funny because that’s always like the scariest question when you have a lot of things that you’re doing and there’s not a super cohesive answer, but just from a high level, I run a family office platform day to day. We’re called Austin Capital. We’re a kind of vertically integrated fintech financial service platform spun out of a family office, a single family office. So we own a bunch of assets in the space, one being a trust bank in Nevada. We have a modern core banking business. So banks and FIs run on our core. We have a payments issuer processor. We have a high-risk payments business. We have a few RIAs, an asset management platform, a professional services business, virtually anything that touches fintech financial services. And we both invest, we incubate, we buy, and we’re really excited about that. Outside of it, I run a farmland marketplace. Think of us kind of like Zillow for farmland called Common Ground that we incubated out of our fund in 2020.

Jess Larsen: Very cool. Let’s do a little bit of backstory. Tell us, tell us a couple of the big career highlights pre-family office work here.

Noah Berkson: Yeah. So I grew up in the Midwest, grew up in Iowa. I was a terrible student, just awful. Had really bad ADHD. But I think I got my first kind of opportunity doing door-to-door sales and kind of learned entrepreneurship in some regard from that. I started out in Cedar Rapids, Iowa, selling home security systems door to door. So you just get rejected all day for a living. You start to really embrace rejection and start to really like it, and it’s like a game. How do I overcome this? I took that experience and ended up going to college, the University of Iowa. I ended up starting a company. Then originally, the idea was to create something called Grid. The idea was kind of like LinkedIn right when LinkedIn was up and coming but still in the pretty early days. And that ended up turning into a software development business. I brought that to Chicago, ended up exiting out of that, and was kind of looking for the next thing. I joined a couple of guys building a health tech business. So we built a SaaS platform for hospitals and health systems to assist with this pharmaceutical drug discount program called 340B. You know, funny enough, it’s been my longest-standing investment and I got some really good news this past Monday about that business. So I’m really excited about that. Then I went and did a joint venture, building a property analytics company. So we used drones to survey pavements and roofs of large industrial property owners, retailers, and REITs. Think of like Walmart and Blackstone and Prologis of the world. We would do these property surveys to help them understand how to do capital and maintenance expenditures. So a very kind of boring business. But bringing a tech approach that made a whole lot of sense. When I got out of that, I ended up starting a staffing business kind of by mistake. I was doing a bunch of angel investing, realized that a lot of the companies I was investing in were saying, “Hey, Noah, can you help us build some offshore engineering teams? I know that you’ve done that in the past. We want to keep our burn down.” And so I was helping with that, and you know, at that point, I said, “Well, wait, I should be making some money doing this. Like I’m doing a lot of work for free.” And I ended up starting a staffing business with a friend of mine. We were lucky enough to scale that. We hit really good timing as well. Think like that 2019-2021 period. We ended up selling that at the end of 2021. Alongside it, we’d spun up a venture fund that was called Candor Ventures. Kind of the insight there was, hey, we’re staffing a bunch of these companies that are really early stage, and we have a pretty unique insight into what’s happening in them because, as most investors sit, they have whatever information the company’s telling you, right? So it’s like, “Everything’s going great. We’re on the upswing. Prospective customers love this.” And we’re in there because we have all these engineers, and they’re like, “Well, the sales demos aren’t working” or “The product isn’t working” or “They’re having these issues.” So we’re like, ah, we kind of have a unique insight here. Why don’t we spin up a fund and just start investing in some of these companies? And so we started something called Candor Ventures, and ended up creating a studio arm of that as well, with the idea to incubate businesses, one of which was that Farmland Marketplace that I mentioned called Common Ground.

Jess Larsen: Yeah, so you’ve told me some pretty impressive numbers before. Are you sharing any of the size of any of these exits publicly?

Noah Berkson: Nothing is public right now. But, you know, we’re really happy about it. I think we rolled part of the deal of our studio and then also of our staffing business into a kind of a Holdco platform, which, when you do that, you’re definitely taking a gamble. I think that will pay off really tremendously for us. So I’m really excited about that. But it also is time, and it’s also putting your time and attention into something for a long period.

Jess Larsen: Yeah. Are we allowed to at least say how many figures without saying the number, or do you want to…

Noah Berkson: Hold on. Yeah. Eight figures.

Jess Larsen: Yeah. So when you think about a business with that many zeros, what did you not expect from all the books and all the YouTube and all the everything everybody tells you? What did you not expect until you actually did it yourself?

Noah Berkson: I think what you don’t expect is, you know, it’s funny, you start out with this idea of building a business. In this case, we really didn’t anticipate selling it, but generally you think, oh, one day I could sell this business. But you don’t do any of the things that you would need to do to sell that business. So when you get to that point and you start in diligence and whatnot, you go, then they’re just dumping like, “Hey, here’s a list of 120 things that we need you to give us.” And you start looking and go, “Well, oh man, we haven’t.” Like, we signed a contract one time with that client three years ago. We never updated our contract. Oh, well, that’s not really… They’re like, “Well, is that a valid contract?” Like, we don’t know. You just don’t set anything up to actually exit out at the end. And so everything is such a mess in the business, and it takes so much time to be able to get all of that together. I think what I see in a lot of other friends and entrepreneurs who have sold their business is because of this, they get into this… I mean, selling a company is generally a lot of work and takes a long time anyway. Always longer than you think it will. But there’s a lot of deal fatigue, and you kind of get to the point in that deal where you go, “I just want to get this deal done.” And I think now understanding from the private equity side, how you think about that as a private equity firm or investor, that’s all kind of part of the playbook. So it’s like we know that there’s going to be deal fatigue in this, and we almost want there to be because at the end when we come back and we say, “Hey, I know we agreed on this number, but we’re gonna only be able to get it done at somewhere below that.” And someone’s just gonna say, “Yeah, I just, you know, I’m mentally now invested in getting the deal done, and I’ve already in my mind like that deal is done, so now let’s just get it done.” And so I think, yeah, I think the deal fatigue and just being ready was something that I really didn’t expect.

Jess Larsen: Yeah. You know, when I was in M&A at Citi 20 years ago, we were doing sell-side transaction fees, and it’s like literally we had to teach CEOs. I’d be talking to somebody who’d owned the business for 30 years and had to talk about, like, “Hey, so let’s think about this as if you’ve never actually played basketball before—the game of selling companies.” And you know, we’re going to send this out to 1,500 private equity groups in a wash description trying to get 100 NDAs signed of people that say the real thing. Get down to six people, you know, six different firms. We want to get a bidding war for you. But here’s the thing. You know, these guys buy many companies per year. You’ve never sold a company in your history. And you start telling them these tricks, right? It was like, honestly, it’s like the car salesman where, you know, they have to keep going back and talking to the mysterious finance guy that you never get to meet. And it takes forever, and they’re giving you tons of drinks so that you need to use the restroom, and three and a half hours later you’re just signing something you wouldn’t have signed two and a half hours earlier, right?

Noah Berkson: Yeah, absolutely. And I think, you know, during the process too, because generally when the process sets out, it’s going to take a period of time to get the deal done. They’ll say, okay, great. And I see this a lot of times in startup or venture companies too. They’re like, “Well, where are you going to be? Let’s say, what are your projections for this year?” And you know, you start this negotiation in February and you’re like, “Oh, we’re going to do 10 million in revenue this year when we did 2 last year.” Right. And they go, “Okay, wow. Like, yeah, incredible.” But by the time that deal is getting done, it is the end of that year, and they’re like, “Well, you said you’re going to be at 10 million in revenue. Like, you’re at 3 million right now. Like, we’re going to have to go back and redo these terms.” So I think also just understanding that all of those things, they’re going to come back to that, and that is the basis that they’re looking at for the business. And so I think also being very realistic about where you’re going with the business.

Jess Larsen: Yeah. So I know we’re not disclosing numbers, but can you tell people which one of the businesses grew the biggest?

Noah Berkson: That you were running our staffing business? For sure. You know, I think having… So we did nearshore staffing; I guess a little bit was outside of that in Asia, but predominantly South America and Latin America. I think you saw, too, that during the ZIRP era, you’d have clients coming and they’d say, “Oh, we need 60 engineers, or we need 40 more engineers.” And you’re like, wow, we’re staffing these people. Right. It’s a labor arbitrage. And they’re really good cash businesses. They can be tremendous cash businesses. I would say now, as I look at it, the industry is becoming a lot more challenging. People are seeing that there’s an opportunity to enter; like, the barrier is fairly low. And so you’ve seen a number of companies start to enter the space. I think what I’m seeing today is companies that are trying to find their niche and say, “Okay, instead of general product, we’re only doing market engineers that work on marketing, or we’re only doing engineers that we staff to fintech companies.” And so you’re seeing people start to specialize a lot instead of being very general. And I’d expect that that’s where the industry will go, at least for the next three, four, five years.

Jess Larsen: Yeah, well, you know, a topic we bring up a lot on the show that’s always interesting to both CEOs and fund managers is fundraising. So thinking about both fundraising as an entrepreneur, fundraising as a fund manager, where you’ve got to get your LPs, and then also being the investor as you’ve had these other roles. Do you notice? Let’s start with what you see as a couple of rookie mistakes out there when people are trying to start raising in the many millions.

Noah Berkson: I think for entrepreneurs that are raising, there are often very arbitrary numbers that get put out. They say, “Hey, I need to go raise this much money” without really realizing: is that amount of money going to get you to where you can raise more money? We see, especially right now, a lot of companies get stuck where they say, “Hey, I’m going to raise $3 million for my pre-seed or seed round.” And that $3 million lasts a year. But a year in, you haven’t actually made that much progress as a business. Maybe you’ve built your first product, got a couple of customers, but that story is not compelling enough to go raise more money at a higher valuation. I see a lot of companies getting stuck right there. I also see a lot of companies that are raising way more money than they actually need. There are many situations now where I’ll talk to companies and they’re like, “Oh, we’re at $300,000 of ARR or $500,000, and now we need to go fundraise,” where they haven’t taken any capital yet. And I’m like, “Why are you doing that?” And they’re like, “Well, that’s just what you do, right? We want to build a team. We want to grow.” And I’m thinking, even though I’m an investor, I’d like to invest in that company from the other side, I would not want to take investor capital at this point. Your life is going to be so much easier because there are a lot of those businesses that can be phenomenal, but they might sell for $30 million, $50 million, $100 million, and own all of it. But the second you take on that investor money, you have to have a huge outcome and everything is driven towards that. Even with my own experience with our Farmland Marketplace, we raised venture capital. We originally didn’t plan on it. We said, “Hey, we’re just going to bootstrap this.” And then in 2020, we started just getting emails from people that were using it like, “Hey, are you raising money?” For a while we thought, “That’s nice. It’s flattering. It means we’re probably on the right track.” But eventually it was like, “No, we want to invest.” And then you go, “Well, if it’s going to be this easy to raise money, we may as well raise money.” But in retrospect, I think you make a lot of decisions when you have money very differently than you would when you didn’t have it. A good example in that business was we said, “Hey, we see Zillow makes a lot of their money from these broker tools or their housing professional tools. The agriculture marketplace is very similar, so why don’t we build some tools for land professionals?” Right away people were excited about it. They were like, “Yes, we can’t wait to use it.” And then we’d give it to them and they’d be like, “Oh, I’d love to use it, but it doesn’t have this one feature yet.” And then we’d think, “Well, we just need to build that next feature. We have the money to do it.” And you go down that path. After a while we realized, “Wait, this is not working. People do not actually want this in the way that we think they do.” Whereas if that was your own money, you would quickly say, “Oh, that’s not working. Let’s just pivot away from that entirely.” Compared to, “Let’s just keep trying and keep trying and keep trying.” That’s a hard lesson to learn.

Jess Larsen: Yeah. Why do you think that bootstrapping is so underrated?

Noah Berkson: Why do I think it’s underrated? I think people really just don’t understand the game as they get into it. Many people are good at one thing, so they start a company and they don’t really think about all the other levers in a company or truly understand where that company can go. There’s just this idea that, “Oh, this can be the biggest thing ever. Our addressable market is huge, so we’re going to capture that. Even if we get 1% of this market, we can be a huge company.” But a lot of people don’t understand that you will never have 1% of that market and how tremendously hard it is to achieve that. And that you also have optionality when you bootstrap. Yes, it is more challenging from the beginning. It does force you typically to get profitable very quickly. Where I see a lot of movement right now is people realizing, with Palantir being a great example, that services can be really lucrative businesses—services kind of as software. So when people bootstrap, they say, “Okay, we need to start with some type of services because we can get customers right away, they can pay us, and that can support the business.” But they think that in the long term that’s going to derail the value of the business. I think we’re finding that it’s quite the opposite today if you can be sticky. Burnout is another piece of this that people don’t think a lot about. When you do something every day and it’s a grind for three, four, five, eight, ten years—probably 12 years is the average that a company is going—you may get to a point where you say, “I don’t want to do this anymore. I’d love to sell the company.” If you bootstrap, your options to do that are great. Generally, if you have a good business, you can find a buyer who’s excited. But when you’re venture-backed, your investors are like, “Are you joking? We signed up for this to be a one or a zero—it’s either a billion-dollar business or it’s nothing.” So they say, “Absolutely not. Get back and keep going.” I think that’s the scariest thing. We have founders who are entirely unmotivated and completely burnt out, but forced to drive toward an outcome that, candidly, probably won’t happen. The investors say, “Well, it’s fine if it’s a zero,” but you’re going to spend your entire life trying to build that company, put everything you have into it, and it may ultimately be a zero.

Jess Larsen: Yeah. I think about a couple of bootstrapping stories out by me. You know, Pluralsight bootstrapped for, I don’t know, like 10 years and then took some money, got into the billions. You know, Qualtrics, same thing; I think they bootstrapped for like 9 years or 12 years or something, and then, you know, reached the tens of billions. Right. And I’ve been at conferences, or, you know, I’ve met both Aaron Skonnard and Ryan Smith, and they talk about things like the discipline of bootstrapping. Like, when you come with that mindset and you figure out your product-market fit, then you pour gas on the fire. Do you know why they feel like that model can be so superior sometimes?

Noah Berkson: Yeah, absolutely. I mean, there are so many great examples of people who have bootstrapped, but also people see the now, right? Like, wow, that company’s so successful. They don’t realize they’ve spent the last 12 years of their life, you know, every day, every day on this business to get it where it is. Backbase was another really good example in the financial services space. That was like a two and a half billion dollar business today that was bootstrapped. But, yeah, I think it’s tremendously underrated. I do think, though, that with the growing proliferation of AI, you’re going to see a lot more companies that have the ability to bootstrap and say, well, I don’t really need to spend 500,000 or a million dollars to build this product. I can get 80% of the way there with, I don’t know, a couple thousand bucks building something, and we can get some revenue and then keep driving. So I hope to see that.

Jess Larsen: Yeah. What’s one thing that you feel like you did right with fundraising?

Noah Berkson: I think being able to tell a story and being realistic is important. I want to set expectations when we’re fundraising. The natural inclination is to say, “Hey, this is going to be the biggest business ever. This is going to be the next Uber, Airbnb, etc.” But I think being able to be realistic and say, “Here are all the challenges in this business; here are all the headwinds we’re facing. If we’re not successful, here’s why we won’t be successful,” helps set expectations from the start. Otherwise, you have investors saying, “You said it was going to be this, and that’s not where you are.” Along the way, you want your investors on your team. That’s really important. Some people look at investors and think, “I just get a check from them,” making it very transactional. But those will be the most important people, especially through hard times. I have friends who had a business issue where they lost a bunch of money—not their fault—and one of their investors stepped in within hours and said, “I’m wiring this over to you”—an eight-figure check—“I’m wiring this over right now; we’ll figure this out later. I want to make sure you guys are okay.” When you tell that investor something that doesn’t materialize, you don’t get that type of goodwill.

Jess Larsen: Yeah. When you think about starting relationships—let’s say with family offices, ultra-high-net-worth individuals, maybe more so than institutional investors—when you think about a less transactional beginning of a true relationship, what’s a principle or something that you feel is effective?

Noah Berkson: I feel like for me it’s always about adding value. I want to add value right away. I think that I want to take as long as possible. You know, when you think about relationships, it’s kind of like long-term investing. This stuff just compounds. I want to have my relationship bank account, and I want to be the person that’s like, “I can provide you so much value. I’m not going to ask for anything.” Because I think then it’s just like you start these transactional relationships, and even if that works right away, in the long term, I feel like those aren’t the relationships that I want to have. So I say, how do I give you some type of value right now? And with ultra-high net worth people, really successful people, family offices, many times that’s challenging for people because they go, “Well, they’re the ones that have all the money, they’ve been successful. How am I valuable to that person?” I’ve found generally it’s through relationships. I spend so much time cultivating relationships across industries. So not just one industry—like, my day-to-day is financial services. If I only knew financial services people, that wouldn’t be very helpful for me. But typically it’s like, “Oh, someone has a random… What are you working on? Oh, we have this random project. We have this nonprofit where we’re funding, like, bees, right?” “Oh my God. Actually, I know the perfect person you’ve got to talk to. They’re really interested in this.” That could be a great connection. Or how do you just find enough people around you that you’re able to connect? I think that’s the easiest way to add value right off the bat. And I also think it’s the way for people that might say, “Well, from a business standpoint, you haven’t been as successful as me, right? So I don’t look at you as a peer, right on my level.” But then I introduce somebody else that’s right on their level, and they go, “Wow.” The second I send an intro, that person responds, and they’re like, “Oh, who is Noah? Clearly he knows the right people.”

Jess Larsen: Yeah, I like that. On your Twitter, it says Chief Networking Officer. Um, so I think that’s a… I think.

Noah Berkson: But sorry to cut you off. I think that’s a big opportunity, by the way. Just if you let me rant. So I think there’s a lot of… A lot of the most successful people that I know, at a point, they become more insular. So they go from kind of being like, “we need to meet everyone, we need to network,” and then they get successful and they’re like, “I don’t really need to do that. I kind of keep my circle close.” And, you know, I don’t make many new friends. Like, people I actually like, I get on calls sometimes, but it’s not like people I actually hang out with. And I think there’s a big opportunity to kind of be like this Chief Networking Officer for people. You say, “I’m going to enter, you’re going to pay me, but it’s a service.” Right. But I’m going to introduce you to a bunch of other stellar people that you would really get along with, and you’ll probably be lifelong friends with them. And so whether that’s like, “hey, I’m traveling here.” “Oh, great. Let me introduce you to this person. You guys got to get together.” I think there’s a lot of that because I think the older you get, you just stop doing all the things. A friend of mine, we go visit in Vermont every year. He’s like in his mid-70s. His name’s Kevin, and he goes out, like, mountain biking with us. Most active mid-70-year-old you’ve ever seen. But, you know, we were asking, “what’s a piece of advice that you have?” And he said, “always have younger friends.” I was like, “why?” He’s like, “well, because as you get older, people just stop doing things, right? All of your friends, they’re kind of busy with their family. They’re busy with what they’re doing. They stop going on the adventures. They stop taking the spontaneous trips. They stop doing the endurance events.” And he’s like, “but I want to do that. So I figured out my conduit to that is just to always make younger friends.” And I really resonated with that.

Jess Larsen: That’s awesome. Okay. Speaking of friends and networking, I figured you got to give a shout-out to our mutual friend AJ who got us together. To me, he’s an example. Like, he’s already introduced me to multiple interesting people. I know you guys hang out a lot together. What do you like about AJ?

Noah Berkson: I think AJ is one of the most dynamic people. His ability to span industries, right? Where he’s respected, not only in the industry that he works in, which was sports and is now in the AI interior design space. But people that you’d meet anywhere respect AJ and they go, “Oh, AJ!” They see him very highly. And I think that’s also because he’s a great connector. He goes out of his way to meet people with no intent, right? So he’s meeting people. He will go to events that have nothing to do with what he’s doing just because he’s like, “I’m gonna go meet people.” You know, it was so funny, actually. A friend of mine said they met AJ and I go, “Where did you meet him?” Because I was like, “Oh, interesting. Where did you guys cross paths?” And she goes, “Oh, it was a women founders event.” I go, “You met AJ at a women’s founders event?” And she’s like, “Yeah, he was like the only… there were two guys there, and he was one of them. And there were like 200 women.” Like, I love this. This is what I love about AJ. He makes his way and he goes to those things, and he seems to just, like in a crowd, find the right people and he builds relationships and he adds value. And he follows up.

Jess Larsen: Yeah, that follow-up is so key, isn’t it?

Noah Berkson: The follow-up is so key, and it’s absolutely the hardest thing. But I think, you know, for instance, for me, I’ve gotten better at it. I’m definitely not the best at it, but I keep a sophisticated system to be able to follow up with people and make sure that I’m keeping on top because it’s really easy. My thought on any new relationship is either you build momentum the second that you meet someone. So, like, you and I hop on a call and we have a good conversation, and then I can either say, “Yeah, cool. Let’s chat sometime, keep in touch.” And that relationship is probably never going to be close because I think you just have that moment of momentum. So it’s like, okay, today, who can I introduce you to that’s going to add some value to your life right now? Oh, let’s make some future plans. Hey, you have something going on. You’re in Park City. I’m going to be in Park City these dates; let’s see if we can get together. And so I think it’s so much about just building momentum right away in a relationship. Otherwise, that’s kind of the difference between having something that’s like, this is going to be a very close friend, or this will be kind of an acquaintance, and maybe we’ll cross paths in the future. But what was the point of us talking if there’s nothing there?

Jess Larsen: Yeah, no kidding. Are you 31? 32? How old are you?

Noah Berkson: 31.

Jess Larsen: When you think about how, like, the level of, you know, going from door-to-door sales and, you know, working, I think, in the restaurant industry before that to millions and millions of dollars at your age, there are so many entrepreneurs that want to do that, and there are so few that accomplish that, especially in that time period. What do you think is different about you? What do you think you’ve done that others haven’t done?

Noah Berkson: I got a really early start. So you think about college. Like, I spent most of that time kind of… I don’t know if acting like an adult. I was super immature, but, you know, kind of living the life of an adult. So, one, I got a really good head start. Two, I think just understanding the value, again, like, back to this, but understanding the value of relationships. And I think from a really early age when I moved to Chicago with my first business, I met a guy who became kind of like a mentor to me. He owned a bunch of restaurants and nightclubs in Chicago, which is the most, you know, random of things for the person that is like a mentor to you. But he just really taught me the power of relationships. And it was clear, like, he owned these things. Yes, there was money involved with it, but he realized the network that he built from it. And it was just an interesting way. Like, you wouldn’t really think of that. Like, “Oh, you own a restaurant because you own a restaurant. You own a nightclub because you own a nightclub.” He’s like, “Oh, but if you see all the people that come to get in here every night, like, I become very close with those people. Those people become my good friends. I have a lot of power in this dynamic. Even though those people may be much more powerful and successful and, you know, wealthier than I am, they really want to get a table on that Friday night, or they really want to get into that nightclub, right?” And so it was just interesting to observe that at a pretty young age. Because, you know, when I grew up in Iowa, I didn’t know what a mentor was, right? Like, I didn’t grow up around wealthy people. Didn’t really have any kind of inkling into that world. But I think going through a lot of rejection and learning to embrace it, that was a big, big learning for me. We went to our team for this door-to-door security sales. We became the top team in the country in Iowa. They would track this week, every week, and how many security systems you’re selling. And so, as a reward, we got to go to South Central Los Angeles for a summer. And basically, the way that the home security industry works is virtually they put people in these five-year contracts and they track this. So if a certain neighborhood has five-year contracts, all of those probably expire right around the same time because they all get sold right at the same time. And so they knew that these areas in South Central Los Angeles were about to expire. And it’s like an area that actually has tons of crime. There’s a reason you have a home security system living there. But we got to go there. And that was kind of like our present because it was, “Hey, you guys are the top performing team. We want to send you there because you’re going to close so many deals. Like, you can make so much money doing this.” And so, yeah, you know, it’s just funny reminiscing on this. We were maybe, I don’t know if it was nine or ten guys living in this like two or three bedroom apartment. If I remember, like, you’re just sleeping on the floor, you get up, you fit everyone into a tiny car, and they just drop you off in a neighborhood. They say, “Don’t take your cell phone, don’t take a wallet, maybe take like a few dollars to grab lunch, you know, at a gas station or whatever. We’ll meet you back here at 9 pm” and this could be like 8 am and you’re just out. You’re very out of place. Like, you feel a little bit on edge the whole time. But you get to this point where like, wow, I can really embrace this. And you’re just loving it and you’re loving being able to look at somebody’s house from the outside and say, “I know every reason you’re going to tell me why you don’t want to buy this. And it’s going to start with you telling me, ‘Get off my property.’ And it’s going to end with you shaking my hand, thanking me so much, you know, and maybe introducing me to your kids who are there.” And so I think just learning to embrace rejection was a really big thing for me as well.

Jess Larsen: Yeah, no kidding. Well, you know, when you talk about this networking and getting people together… I know your conference is coming up. Why don’t you talk about your podcast and your cool co-host?

Noah Berkson: Yeah, I just started a podcast. I will release it hopefully sometime in December. Maybe it’ll be early January, I think. I’ve learned very quickly in starting a podcast. You think it’s very easy, as I’m sure maybe when you started that you did, and then you realize, wow, there’s a lot that goes into this, like, oh my God. But I started with a friend of mine, another entrepreneur named Jeff Ma, who you’re going to speak with, I think, at the beginning of the year here. We came together and we were talking about a platform. We said, hey, like, there are a lot of podcasts out there that we like, but a lot of it, there’s not a whole lot of vulnerability. A lot of what you’re seeing is like, it’s “How I Built This,” which is fantastic. It’s kind of the story of how you started the business. It’s the, “hey, I’m really wealthy now,” but it’s not the, “I don’t know what’s really hard in your life, what’s super challenging.” Like, hey, you’ve made all this money, but are you actually happy? Because time and time again, I think you realize that the people that have done that, they’re just as unhappy as everybody else, maybe more unhappy. So we wanted to create a framework around that, to be able to interview really interesting people, but just understand, like, what are they going through, what is their life like? And the way that we preface it to guests is if somebody wanted to get to know you on a very personal level, you would send them our podcast as a way to do that. So we’re really hoping that can turn into something. I’ve spent a lot of fun doing it, and I just realized, like, I get so much energy from it. I mean, you have the best job in the world with this, being able to just interview a bunch of really interesting people and get to chat with them. And that’s—I mean, I don’t know what more you can ask for. One thing I will say that I think is funny—I had a podcast before that was in the venture capital space, but when I was getting into venture, I was like, I need to meet investors. But most investors don’t really care to meet you. It’s not like the top priority of somebody when you’re like, “hey, I’m just getting into the space and investing.” They’re like, “great. Are you raising money for a company?” “No.” “Like, I’m really busy. Are you going to invest in our fund?” “No.” “Okay, great. I’m really busy.” I was like, that’s kind of challenging. So I said, well, actually, I have an idea. One day I just wrote this cold email that I was going to send on LinkedIn. And I said, “hey, I’m starting a podcast around the venture capital space called Venture Candor. We’re planning our first 12 episodes. We think you’d be a great guest for the podcast.” And I sent maybe 60 of these out, 59 people in a day or less responded and said, “I’d love to.” No one asked, “how many views does this have? Where is it distributed?” None of that. Just like, “yes.” And you’re like, oh, that’s kind of interesting. I could reach out to these people and say, “hey, I’d love to grab a coffee.” And they may say, “yeah, let’s look at Q4. How’s Q4 look?” But when you’re like, “hey, we’re doing a podcast,” people are like, “oh, I’d love to do that. How’s next week?” So just learning that and understanding that was really interesting and informative. We’re looking forward to getting that launched.

Jess Larsen: Yeah. What’s the title?

Noah Berkson: Dose of Greatness.

Jess Larsen: Dose of Greatness. Okay.

Noah Berkson: Dose of Greatness.

Jess Larsen: And tell us about your co-host.

Noah Berkson: Jess is a, she’s been a kind of lifelong entrepreneur, I think. Started in high school and built a website hosting business in high school that was making six figures. Ended up co-founding a company called Indinero, which is an SMB software accounting company. Took a path that was venture-backed and just turned it into a cash flow business that you don’t see very often, but was able to parlay that into a lot of other businesses. Runs a family office now called Mawe. So they do a lot of incubating and investing in companies and then has something called Astonishing Labs as well, funding some breakthrough biotech research. She has parlayed a normal business right into a large portfolio and, you know, ultimately a family office investing platform.

Jess Larsen: Yeah. So, you know, long-term listeners of the show will know my other mini-series called Longevity for Investors with Dr. Greg Bailey, the biotech investor. And he had brought her up to me first. So I was like, hey, check out this super successful female entrepreneur. She pilots her own jet, flies her own, does all this stuff. And she is back. You know, she’s been supporting one of the companies he’s invested in, Mike Levin out there with Morphaceuticals, which is like basically science fiction come to life. And so it was fun to hear about her from you as well and then get back together. And I’m excited to have her on the show. When you think about the power of a podcast and what you’re looking at in February with your event coming up, why, what was your interest in going from digital to adding the in-person side with events?

Noah Berkson: Yeah, I mean, I think that the podcast is a really good way to meet interesting people. That’s what we’re doing. We optimize for wanting to meet really interesting people and being able to tell their story to the world. We look at the podcast not really as a business in the sense that it drives revenue or is a moneymaker. It’ll probably be a money loser, candidly; fingers crossed it’s not. But we’ll see, and we’re kind of prepared for that. I think what we realized is the power of bringing people together. Another thing with networking is that a lot of people look at it differently. They say, “Oh my God, my network. I have 2,000 people on LinkedIn I’m connected to.” The way I look at it is your network is valued not by the number of people in it, but by the number of people that know each other because of you, that wouldn’t have met otherwise. We meet a lot of really interesting people, but where is our ability to bring all of those people into one space to really get to know each other? People from completely different industries who aren’t necessarily there to get someone to invest in their company or do a deal, but to meet others like themselves. I think that’s kind of a lost art where everything conference-wise is very transactional. You get sold on going because you can sell people your product or get investors. Everything is very agenda-driven. When you can set the agenda for everyone and say, “We want you to come and all you’re going to do is meet really interesting people from different industries,” it’ll open your worldview up a little bit. You’ll get different experiences. We’ll have fun together. It’ll be bonding.” From the conference perspective, what we see in the market today is there are a lot of conferences that are business conferences with great people you might want to do business with or be friends with. But the content is stale. You sit there with a bunch of speakers, and you’re not really invested in it. On the other side, there are things that are very fun, like Summit Series or Burning Man-esque events. Those are really fun, but the people are often a little bit too woo-woo for me, and I don’t know that a lot of relationships will evolve out of that time together. So I asked, how do you merge that? How do you have something with really incredible people where you’re also able to have fun together? The bonding comes from doing things that are fun, not from sitting there listening to a speaker and regurgitating that afterwards, but from being able to go snowboarding together or do things that are out of the ordinary. I think that’s where a lot of the bonding comes from.

Jess Larsen: Yeah, it’s certainly been that way for our Innovation Leadership Live series. And I’m super excited to see what your Park City One ends up looking like. It’ll be fun to have you up here for our Park City One during Sundance.

Noah Berkson: So very much looking forward to that.

Jess Larsen: Yeah. Well, if people want to follow you online or check out the companies, what are the best places?

Noah Berkson: I would just be at Noah Berkson on LinkedIn. B-E-R-K-S-O-N. Same thing on Instagram. I would say I’m not active on Instagram, but you can still follow me there. Looking forward to connecting with people. I think my goal is to be a magnet to interesting people and, you know, it’s kind of agenda-less, but I just want to meet people and if I can add value, I’d love to do that.

Jess Larsen: Yeah, maybe to close. What’s one of the best pieces of advice you ever received?

Noah Berkson: Yeah, I would say it’s be long-term greedy. I think somebody said that to me. And when you’re younger, that’s really hard. I think, you know, as I look at it, I joined some of these business groups really young and you’d be around people that are in their 40s, 50s, 60s, and 70s. When you’re in your 20s and you go, well, you have all these things, like, why don’t I have that? Like, we’re here, you know, quote unquote, we’re like peers. But you’ve had, you’ve been way more successful. You have all these things, you’ve done much better financially than I have. Why don’t I have that? And I think that can make you make very short-term decisions that aren’t going to be very optimal for the long term. And it’s like, how do I make this as quickly as possible? And generally, whenever you’re like, how do I make money as quickly as possible? That doesn’t go well. But really looking at things in a much longer time horizon. So be long-term greedy.

Jess Larsen: I love it. Thanks for doing this, and thanks everybody for listening.

An Environment Built for Depth

Outcove creates immersive experiences designed to transcend superficial interactions. As one attendee put it, "Outcove is a place where you can drop the script, be yourself, and let people see you for who you really are."

The retreat's team designed every element around psychological safety and genuine connection:

• Small-group circles and relaxed table discussions invited guests to share victories, failures, and the questions keeping them up at night.
• Intellectual and spiritual conversations flourished in an environment where, as one participant noted, "you can walk up to any single human being, and you're going to have an intellectual, spiritual conversation — that's amazing. That's a blessing."
• Ample informal time — conversations over shared meals, walks through the winter scenery, and impromptu hangouts — let new friendships form organically.
• Evening socials with a live band, DJ sets, and a silent disco added laughter and lightness after the day's deeper dialogue.

Video

Watch the full recap video on YouTube here.

Or watch it below:

Themes That Emerged

Themes — What Attendees

Vulnerability as a superpower — "Vulnerability is something that is just such a moment... The coolest thing is just coming as a stranger to everyone else here and just leaving having, you know, five, ten very close connections that you meet and people that you really connect with."

Authenticity over posturing — "When you stop trying to impress and start trying to connect, you build relationships that aren't just about what you can get but what you can give."

Intellectual & spiritual depth — "When you're in a group of people where you know that you can walk up to any single human being and you're going to have an intellectual, spiritual conversation that's amazing. That's a blessing."

Forward-looking dialogue — Sessions dove into "the cutting edge of something that's going to affect all of us right now."

Key Takeaways

1. Authenticity attracts. Showing up as your whole self breaks down walls faster than any elevator pitch.
2. Depth over breadth. A handful of meaningful relationships outweighs a stack of business cards.
3. Shared vulnerability accelerates trust. The curated environment and shared mindset enable strangers to develop deep connections in just days.
4. Community fuels insight. The retreat creates a supportive environment where people connect on a deeper level with "incredible humans."
5. From transactional to relational. The emphasis shifts from asking "what can I get?" to "what can I give?" — transforming how professional relationships form.

The human skills that emerge from these gatherings are ones I explore in The Human Skills That Make Us Irreplaceable.

Conclusion

Outcove's Park City retreat proved that, given the right setting and mindset, professionals can forge partnerships—and friendships—that last far beyond a single weekend.

As one participant simply advised those considering future events:

"Be open-minded and just come and meet some incredible humans."

Listen to our podcast to keep up with everything related to Outcove.

Interested in joining our next event? Apply here.

I've launched eight companies, taken three from idea to exit, and backed dozens of early-stage teams.

Along the way, I've learned that trust and alignment matter more than spreadsheets or slide decks—especially when markets get shaky.

The Volume Game: Reality of Early-Stage Investing

One truth that aspiring investors often miss is the sheer volume required for success.

About 90% of the businesses you invest in will fail – that's just the nature of the game. If you're only writing one check every few months, you're not playing the odds correctly.

"I invest in one company every once in a while" is a mindset destined for disappointment. If you genuinely want investment returns, you need to be writing about ten checks annually.

There are certainly people who invest for social status or networking opportunities, but if making money is your goal, volume is non-negotiable.

This reality creates both a challenge and an opportunity. You need sufficient capital to maintain this pace, and you must accept that most ventures won't succeed – regardless of how convincing the founders are during their pitch.

Why I Put My Own Capital on the Line

A cornerstone of my investment philosophy is using only my own capital. I choose not to invest other people's money, which fundamentally changes my relationship with founders in a way that creates genuine alignment.

Putting personal money into every deal keeps me honest. The founders know I'm not managing someone else's expectations or chasing artificial multiples—I'm shoulder-to-shoulder with them.

Because my returns aren't tied to a venture fund's timeline, I'm comfortable supporting an exit that triples our money in two years instead of swinging for a mythical 100X return that might never materialize.

By investing my own funds, our incentives are directly synchronized.

We've had multiple businesses we've invested in that have sold, and while they might not have been considered "venture scale" exits, we tripled our money in a year or two.

That's a fantastic outcome that makes everyone happy. I don't need every investment to be a home run; consistent wins compound over time.

Trust: The Hidden Multiplier in Founder-Investor Relationships

Term sheets outline equity; trust determines outcomes. The traditional venture model often creates problematic situations where misalignment leads to poor decisions.

When founders and investors trust each other, they make better choices that benefit everyone involved.

Embracing Founder-Friendly Capital

I've seen scenarios where founders receive acquisition offers that would be life-changing personally – enough money to be set for life. But their investors, who need outsized returns to make their fund economics work, push them to continue growing.

This frequently leads to companies becoming too valuable to be acquired yet still unprofitable. Eventually, they sell at a significant discount.

After preferences are paid to investors, founders who spent a decade building may walk away with surprisingly little – sometimes less than they would have earned at a steady job.

By removing these pressures, I can have honest conversations about what's genuinely best for both the company and the founder.

Taking venture money often means those investors need a certain outcome because they're investing other people's money, which comes with expectations for specific high returns.

My approach of investing personal capital sidesteps much of this pressure.

Looking for Grit: Betting on People, Not Plans

I back people who combine stubborn optimism with raw grit—founders who'll absorb a string of 'no's, pivot when reality demands, and come back swinging the next morning.

The original business model that anyone pitches is almost never what they end up doing, so it makes little sense to overanalyze the initial business plan.

A perfect example is a friend who founded one of the most valuable AI companies in America.

Her early investors didn't back her because they foresaw the AI revolution – they invested in an app for skipping nightclub lines.

The business pivoted dramatically before finding its true path to success.

This is why I focus more on the founder than the idea. Can they handle constant rejection?

Can they show up day after day when things look miserable? Do they genuinely want to keep going despite all the challenges? That resilience is what I'm betting on.

The Founder's Mindset: Strategic Naivety

Interestingly, my approach as a founder is almost the opposite of my investor mindset.

When starting companies, I've found value in embracing a certain amount of strategic naivety.

As a founder, I want to maintain blind optimism that something is going to work. I often prefer entering industries where I don't have extensive prior experience.

This helps me avoid the trap of knowing too much about the challenges ahead.

When you know too much about an industry, you might never start because you're already aware of all the obstacles and reasons something "can't be done."

Looking back at many of my businesses, if I had known in advance how difficult they would be, I might never have started.

That naivety served me well – it forced me to figure things out as I went along, without being limited by conventional thinking.

Turning Volatility into Opportunity

Economic downturns scare off capital—and that's exactly when the best vintages get bottled.

I've discovered that periods when most people avoid investing often present the best opportunities.

While many investors freeze their checkbooks during uncertainty, I look for founders still shipping products and winning customers.

Valuations become more reasonable, competition thins out, and the eventual upswing rewards those who kept building.

My role is to stay calm, provide runway, and remind the team that uncertainty is fuel for creativity, not a stop sign.

It's similar to the stock market – when it's in free fall, those who remain calm and have cash available often find the most advantageous entry points.

Institutional investors typically slow down during uncertain times because their limited partners get nervous about deploying capital during "uncertain" periods.

In retrospect, many of today's most important companies secured funding during economic downturns when capital was scarce.

The companies that survive these challenging environments often demonstrate the kind of resilience that leads to extraordinary outcomes.

Keeping Dry Powder: Balancing Patience with Liquidity

Early-stage investing demands both volume and stamina.

I write enough checks each year to let the power-law work, but I also pause periodically to ensure the portfolio's paper gains have a path to liquidity.

After actively investing for several years, you might have a portfolio that looks fantastic on paper, but if nothing is liquid, you naturally question how long things will take and if those investments will truly pan out.

These periods of reassessment are healthy. They force you to evaluate whether your strategy is working and when you might actually see returns rather than just paper gains.

Cash reserves give me the confidence to double down when a standout company pivots into its breakout moment—like Bluon transforming from a refrigerant replacement into the data backbone for 60% of America's HVAC technicians.

This company began as a replacement for a chemical being phased out, but through insight and evolution, it became one of the largest data companies in the HVAC industry.

It's been incredibly rewarding to watch that pivot from a physical product into a technology powerhouse.

Knowing When the Time is Right

Timing is everything. One of the hardest skills to develop is knowing when to sell a business – whether as a founder or an investor.

For me, the decision has never been purely financial. I ask myself: Am I still energized by the problems this business presents? Different stages of growth require different skills and interests.

The challenges of early customer acquisition are vastly different from managing large teams or creating five-year forecasts.

I've learned to be honest about whether I'm still the right person to lead a company through its next phase. This self-awareness has proven invaluable, both for my own well-being and for the success of the businesses I've built.

The Bottom Line

Building valuable companies takes time – often 10-15 years, not months or quarters. Trust, alignment, and disciplined patience serve as my compass when the macro picture turns murky.

I prefer creating sustainable, continuous ways to generate returns and compound wealth rather than chasing unicorns.

By investing my own capital in sufficient volume, focusing on founders with extraordinary grit, aligning our interests authentically, and recognizing that the best opportunities often emerge during the most challenging times, I've built an approach that works through all economic cycles – even when the future seems most uncertain.

If you're a founder navigating uncertainty and looking for an investor who's equally invested—both financially and emotionally—let's talk.

Those were the words coming out of my 7th grade social studies teacher's mouth at a parent teacher conference.

The worst part was, I wasn't even a bad student. I had terrible ADHD which made it almost impossible to focus. But those words had a major impact on my entrepreneurial journey.

My entrepreneurial journey began with these harsh words that made me feel stupid, insecure, insignificant, written off.

It made it even harder to be present and participate in class.

Entrepreneurial Motivation

Over time, those words put a major chip on my shoulder. They made me want to prove I wasn't stupid, not someone to be written off.

So I started a company. Then another. Then another and many more. But while those words helped motivate my entrepreneurial drive... They made my entire identity my "success".

My entire self worth became based on how my businesses were doing. It was terrible for my mental health and continues to be.

I talk to so many entrepreneurs who have had similar experiences on their entrepreneurial journeys.

It's like you have a tool or tactic that has worked so well for you in the past but due to different circumstances it is no longer useful. Yet you have a hard time letting go or dropping it.

As an entrepreneur, I find myself in this situation now. I know it no longer serves me, yet I am still trapped in this loop.

Entrepreneurial Growth

This year I'm focusing on letting go as part of my entrepreneurial growth. I'm learning to forgive myself and others.

Ultimately I'm learning how to step back and not take everything so personally. The entrepreneurial drive that once propelled me forward is the same force that now keeps me chained to outcomes I can't always control.

Entrepreneurial success became my shield against those early judgments, but what happens when business has ups and downs? My worth as an entrepreneur shouldn't fluctuate with my company's performance, yet I've conditioned myself to measure my value this way for so long.

I explore the dual mindsets of building and investing in Investor vs. Founder.

Conclusion

Has anyone else had success with this aspect of their entrepreneurial journey?

How have you separated your self-worth from your entrepreneurial achievements?

What strategies have helped you forgive past hurts and move forward with a healthier entrepreneurial mindset?

I'd love to hear from other entrepreneurs who've broken.

Follow me or send me a message on LinkedIn by clicking here.

Wearing both the founder and investor hats has taught me that success hinges on three things: understanding why most investments fail, respecting timing at every stage, and spotting the subtle signals that say it's time to sell.

Common Obstacles in Early-Stage Investing (and How I Approach Them)

Failure is the default. Roughly nine out of ten companies I see won't make it, so a one-check-a-year hobbyist strategy is just roulette in nicer clothes. Real diversification means writing dozens of checks, not one or two.

Volume isn't enough without patience. New angels sometimes email me asking when to expect dividends; the honest answer is "not this decade."

Early-stage companies and investments burn cash for years, and liquidity events—if they come—often land in year ten or fifteen.

It's never about the business model. When you're investing at the formation stage of a company, trying to evaluate the business model makes very little sense. The original pitch rarely survives first contact with the market.

Most startups pivot multiple times before finding a product-market fit. The initial idea investors back almost never resembles the final business that succeeds.

When making an early investment, you're not underwriting a business model—you're betting on a person.

Expectation-setting matters. I tell founders up front that my capital is personal, not pooled from outside LPs.

That aligns us: a 3× return in two years is great for me and life-changing for them. No one's forced to swing for a mythical 500× home run.

The Importance of Timing in Investments: Lessons from My Own Ventures

0 → 1, 1 → 10, 10 → 100 are different sports.

Early on, I thrive on messy discovery; later stages demand forecasting, process, and people management—work that energizes some founders and drains others (myself included).

Knowing which phase excites you keeps both you and the company healthy. Mis-timed valuations kill exits. I've watched friends reject life-changing offers because VCs wanted bigger multiples.

A few years later, those same companies were overpriced, unprofitable, and effectively unsellable. Timing, not just growth, ultimately determines whether you win or lose.

The consequences of missing the right exit window can be brutal.

When companies eventually sell at a significant discount, investors typically recover their money through preference stacks, while founders who spent a decade building might walk away with almost nothing.

Even pocketing a million or two after taxes and years of effort often means they would have been financially better off simply taking a regular job during that time.

Markets move—founders must, too. The most successful companies I've seen weren't those with perfect initial ideas but those that could pivot quickly when market signals changed.

I back founders who can read the clock and adapt rapidly, even if it means completely transforming their business model.

Knowing When It's Time to Exit Your Investments

Energy is my north star. If I'm no longer intellectually lit up by the problems in front of me, it's time to consider selling—no matter what the spreadsheet says. Burning out helps no one.

For me, the decision to exit comes down to two questions:

1. Am I still energized by what I'm doing?
2. Am I working on problems that mentally stimulate me?

As a business scales, the problems you face change dramatically. In the beginning, you're focused on getting early customers, forming partnerships, and hiring your initial team.

Then you shift to managing people (which I personally don't enjoy), building larger teams, and long-term forecasting.

Optionality beats obligation. Because my investors are myself, I can say yes when a "mere" 10× outcome appears. That flexibility prevents the valuation-creep trap that strands founders on an island of paper riches with zero buyers.

Watch for silent alarms. Rising customer-acquisition costs, investor misalignment, or a creeping dread of Monday morning all signal it's time to explore exits before the window closes.

I'd rather leave some money on the table than wrestle with a tired company for another five years.

Finding Opportunities in Economic Uncertainty

I've learned that the best investment opportunities often emerge when nobody wants to invest. Usually, those moments are the most opportune times.

It's true in the market too—when everything is in free fall, the people who remain calm and have cash are thinking, "This is the best time ever."

Most people don't think that way. When investing other people's money, those people often say, "Things aren't going well.

I don't want my money going out during such uncertainty." So VCs typically halt capital calls and slow down their investments.

But those are generally the most advantageous times. It's all in retrospect, though.

When people look back five or ten years later, they say, "Yeah, that was the perfect time," or "That was when this business became one of the most important companies in the world, but nobody really believed in it at the time."

Key Takeaways

1. Diversify aggressively—early-stage success is fundamentally a numbers game.
2. Respect the clock—from market cycles to personal motivation, timing rules everything in business.
3. Exit while you still love the chase—passion, not spreadsheets, tells you when it's time to move on.

Each role demands distinctly different mindsets and approaches. Understanding these differences has been pivotal to my career and has deeply shaped my philosophy in business and investing.

Here are the differences and what you need to know.

The Founder's Mindset: Optimism and Naiveté

As a founder, I've discovered that embracing optimism and even a level of naiveté is critical.

It might sound contradictory, but coming into a business with a certain level of blindness to challenges can actually be an advantage.

When I've started businesses, I've intentionally chosen industries where I wasn't overly familiar. The logic behind this is simple—if I had fully grasped all the difficulties upfront, I might never have taken the leap.

Reflecting back, many of the ventures I've launched came with unforeseen complexities. If I were asked now whether I'd jump into some of those ventures again, knowing what I know today, I'd probably say no.

Many businesses I've ventured into posed challenges far beyond my expectations. But precisely because I didn't fully grasp the complexities initially, I was forced to innovate solutions quickly—often turning apparent setbacks into opportunities.

The Investor's Mindset: Skepticism and Discipline

Transitioning from founder to investor requires shifting gears dramatically. Unlike the enthusiastic optimism that drives a founder, an investor needs to approach opportunities with disciplined skepticism.

The default answer for an investor must typically be "no" because most opportunities won't pan out. It's essential to be able to read people, understand their grit, and judge their ability to navigate the inevitable failures ahead.

As an investor, I've learned to embrace the reality of frequent pivots and business model shifts. Investing is fundamentally about backing resilient individuals because the business they start is rarely the business they end up growing.

A memorable example involves Lucy Guo, founder of Scale AI. Her early investors backed an entirely different idea initially—an app designed to skip nightclub lines.

The eventual pivot into AI training models wasn't the original business investors signed up for. This illustrates perfectly how the original idea often matters less than the adaptability and resilience of the founder.

Investing in the Person, Not the Idea

Early-stage investing, in particular, is less about evaluating the business idea itself and more about assessing the founder's ability to persist and pivot.

I always look for founders with grit—the people who can handle repeated rejection, stress, and failure, yet still choose to show up each day. The initial pitch often evolves dramatically, and investors must anticipate this.

Finding the Balance

Having navigated both these roles, the key lesson I've learned is to maintain clarity on which "hat" I'm wearing at any given time. Living in both worlds means knowing which hat I'm wearing at any moment:

• Founder hat: Say yes, leap first, and figure it out on the way down.
• Investor hat: Start at no, interrogate the risk, and bet only on founders who’ll keep showing up after the ninth rejection.

As a founder, I'm driven by vision and possibilities, willing to tackle seemingly insurmountable problems head-on.

As an investor, I remain cautious, analytical, and aware of the high risk involved, prioritizing character and resilience above all else.

Recognizing and mastering these distinct mindsets has made me better at both starting ventures and making strategic investments, each feeding valuable insights into the other.

Follow me on LinkedIn for insights like these.

My friend roasting me

Then I gathered all my friends and had each come up and roast me.

People said "are you crazy, why would you ever do that!?"

I've never felt more loved.

There was a recent study that showed contrary to popular belief, friends who playfully insult each other, as long as in jest and fun, are exponentially more loyal and honest.

Ultimately, when friends tease us, it's demonstrating they know us quite well.

Would you sign up to be roasted for your birthday?

The relationships that make moments like this possible are why I created Outcove.

What They Actually Said

A few things came up repeatedly. Too many hours at the office. A habit of over-explaining decisions to people who already trust me. The fact that I apparently make the same three jokes in every group setting and act like it's the first time I've told them.

I'm not going to pretend none of it stung. Some of it did. But here's the thing: none of it was a surprise. I already knew most of it. I'd just never had anyone say it out loud, to my face, in front of everyone I care about.

There's a difference between knowing something about yourself and having it named. The naming part is what actually changes things.

What I Learned About Myself

Two things surprised me.

First: the stuff that landed hardest was also the stuff that got the biggest laughs. Meaning the people who know you best can see your blind spots clearly and still love you anyway. That's a rare thing. Worth protecting.

Second: the exercise forced my friends to be honest in a context where honesty was expected and celebrated. Most of the time, the people closest to you are editing themselves to protect your feelings. The roast gave everyone permission to stop.

I got more useful feedback in two hours than I'd gotten in two years of casual dinners.

The bottom line? If you want to know how you're actually showing up in the world, stop asking people how you're doing. Give them permission to tell you the truth. Some of them have been waiting.

In this podcast, we talk about the following:

• The Nature of Tech Journalism - Ben discusses how tech journalism differs from other beats, why he's drawn to covering venture capital, and how tech startups create interesting stories because founders aim to build the next big thing, not just profitable businesses.
• The Legal Aspects of Journalism - Ben describes the extensive legal vetting process that occurs before publishing stories, how he handles threatening letters, and his commitment to protecting anonymous sources even if it meant going to jail.
• Interviewing High-Profile Figures - Ben shares his experiences interviewing notable tech figures like Adam Neumann, discusses his approach to preparing for interviews with high-profile subjects, and explains how he tries to ask questions others haven't asked before.
• And many more!

Video

Watch the full episode on YouTube here.

Or watch it below:

Full Transcript

Ben Bergman: People don't start tech companies to create a mildly profitable business. They create it to create the next Airbnb. Well, you just have to have better sources. It's really the same for every form of journalism. And you're only as good as your last story. Poker is just, you know, in terms of assessing risk versus reward. I'm not allowed to invest in companies. I'm not allowed to take any consulting fees. I'm not allowed to be paid for stories.

Jess Mah: Ben, welcome to the pod.

Ben Bergman: A pleasure to be here.

Jess Mah: Yes. Wondering if you can tell everyone 30 seconds about yourself.

Ben Bergman: So I'm a senior correspondent at Business Insider, where I cover the very exciting world of venture capital and startups. Before that, I was a producer at NPR for a long time and then a reporter at the NPR station here in LA. I did the Knight-Bagehot Fellowship at Columbia Business School, and I was the founding senior producer of The Journal, the daily podcast for The Wall Street Journal.

Jess Mah: That is baller. That's awesome.

Ben Bergman: Thank you, thank you.

Noah Berkson: Tell us about that process of starting the podcast for The Journal.

Ben Bergman: So this was after I did this fellowship at Columbia Business School. I had always been a journalist, and I thought it would be interesting to try to be on the other side, to be more on the management side of media. And this was, of course, when The Daily had launched and was enormously successful. And so I got a six-month gig, Gimlet Media, and they did this partnership with The Wall Street Journal to be the competitor to The Daily. And so we were testing all this stuff out and in the origins of starting the podcast. And it was a great experience, but it was not for me. I really missed being a journalist. I love being a journalist. I didn't like being more of a manager and being in meetings all day.

Noah Berkson: Have you always known that you wanted to be a journalist?

Ben Bergman: Yes. So I had a newsletter when I was about 10 years old called Benny's Bulletin. My mom started the first parenting magazine in the country, and I would go up and work around her. And in high school, I would read The Daily News every morning. In college, I got to intern at The New York Times. So I really always have.

Noah Berkson: What was the first interview that you remember doing?

Ben Bergman: Well, I remember when I was in middle school, APEC, the Asia-Pacific Economic Cooperation, came to Seattle, and Bill Clinton was there, the president at the time. And I got to go cover that. And then he came to actually one of my classes in college, and I wrote that up for the college newspaper. And that did pretty well.

Jess Mah: And then did you ever imagine you'd actually be successful as a journalist and be able to interview, like, Adam Neumanns and Dalai Lamas of the world?

Ben Bergman: Well, I hoped so, but I wasn't sure. I mean, journalism is such a hard field to break into, and I thought I might give it a try and be a lawyer if that didn't work out. But really, journalism is all I wanted to do. But I had no idea that I would be a tech journalist or what kind of journalism I would do.

Noah Berkson: Why tech journalism?

Ben Bergman: Well, I always tell people, you can plan and say exactly what you want to do, but it never really works out that way. But I think I became a tech journalist because I did the program at Columbia Business School, and it's where the action is. Tech is the most exciting, interesting people. People don't start tech companies to create a mildly profitable business. They create it to create the next Airbnb. And so that really makes a lot of interesting people and a lot of interesting stories. And I used to cover politics, and politics is very important, but everyone covers politics. There are hundreds of reporters, but I'm really one of only a handful of reporters that covers venture capital.

Noah Berkson: What's the key to being successful as a journalist in politics? If you're going to be the top of the top, what do you need to do differently than the other 99%?

Ben Bergman: Well, you just have to have better sources. It's really the same for every form of journalism. It's not the writing that's the difficult part. It's getting the information. And you look at the top reporters, like Maggie Haberman or Jonathan Swan, and they just have great sources. They're able to break stories that no one else is able to.

Noah Berkson: So it's really a network that you need to create over time that allows.

Ben Bergman: You to get those cultivating sources, finding sources, and getting them to tell you information.

Jess Mah: And you're a really popular person. You have a ton of friends. You throw great parties, from what I hear.

Ben Bergman: Where did you hear that?

Jess Mah: From you? Is that from me? Is that… Is that part of what makes you successful? Because you're making genuine, authentic friendships with people. And because of that, people are more likely to advise you on what to talk about.

Ben Bergman: People always ask, is this for work or for fun? And it's all really part and parcel of the same thing. And I do love people, and I love hosting people. That's why I host poker games every weekend at my house. That's why I do love having parties and events and going to a ton of stuff, because I think it's meeting people. Everything comes from meeting people. Whether it's a job opportunity or playing on an amazing tennis court or getting a story idea, it doesn't come from sitting at your desk.

Noah Berkson: How does that change the way that you build relationships with people? Because I imagine people go like, oh, I want to be your friend, but also I'm a little wary about maybe what I tell you. Is that going to end up in an article? Or could there be some negative repercussion?

Jess Mah: From this if I get too hammered at Ben's house, it'll be published tomorrow.

Ben Bergman: Well, it's funny because I'd say most of the time it's the opposite. Like, people are so excited to pitch their startup or get me to write about them that, you know, that. And sometimes I'm like, oh, is this person just wanting to be friends with me to get me to write about it? But there are people who definitely are afraid of reporters or afraid that I'm just going to write up something that they say. And that's not how it works. I'm not, you know, I will, you know, get ideas or someone will say something, but I don't think people understand, like, the level of reporting that it takes to go into a story. So I'm not just going to write up something that I hear at a random party.

Noah Berkson: How often does that happen where you feel like people approach you or try to befriend you, and it's like you realize that it's kind of clear that they just have the wrong intentions?

Ben Bergman: Well, you know, we are in somewhat of a transactional town, and I think, you know, that it depends where you go. You know, I'm reticent to go to Tech Week events or something like that because that can happen a lot. And I try to be open to everything because just like a VC always wants to have a wide purview and hear lots of ideas, you never know where a good idea is going to come from, and you never know who's going to have value in a certain way. But it's nice when it's not just purely transactional.

Noah Berkson: Do you feel like a lot of conversation as a journalist? Is it pretty transactional? You feel like as you're meeting people, as you're doing stories, is that generally the way that you feel when you're going into a story?

Ben Bergman: No, I would hope not. I think there's clearly people who just want something, but it's not entirely wrong either. I also try to provide value to people as well, whether it's giving them publicity or getting word out about something or giving them information that they want as well. Because it can't just be a one-way street in any dealing that you have.

Noah Berkson: Do you have any example of something where you've written an article about a company, and it's just been, it's helped them in a huge way, been super beneficial to them personally, to their business?

Ben Bergman: Yeah, it happens a lot. I mean, because we do a lot of lists. People love lists, whether it's the rising stars of VC or the best startups to work at. So we put a lot on the map. And in terms of a VC firm, I wrote about this firm, Trek VC, because they use an AI algorithm to determine future unicorns. And they said that got them so many deals once we wrote about them because people hadn't really heard of them. And then everyone was like, wow, here's this firm, they're doing well, maybe we should let them on our cap table.

Jess Mah: Wow, that's sweet.

Noah Berkson: You've had, I guess in another example, negative things about companies where it's been very harmful to them or that's created enemies for you out of writing about companies?

Ben Bergman: Yeah, that's part of the job. I really don't think you can be a journalist if you're afraid of what people think. And I never want people to just… No one's going to respect me if I just write nice things all the time. At the same time, I never want to just be known as someone who writes hit pieces or is negative for the sake of being negative. But after I've written critical stories about companies and VCs, people always reach out to me either to say, wow, I'm so glad you finally wrote that, or here's another idea, or we respect you if you wrote something that was accurate. Not a hit piece, but something that everyone talked about but no one has written about.

Jess Mah: Yeah, well, speaking of which, over the past year I've had a lot of people mention an article that you wrote about Mark Suster, and they were commenting on what it was like to be on the board of a company with Mark Suster also on the board and how they perceived him to be reacting to the story. And most of the feedback was he didn't take it very well, and he was a bit pouty and sour about it. What was that like for you? Are you worried about making enemies? Because LA is a pretty small town. How do you think about that?

Ben Bergman: Well, yeah, I mean, I think that story was a little more difficult than normal because Mark is a legend here in LA, and I live in LA, and it's a small venture community. But, you know, Mark and I still talk all the time. He still invited me to Upfront Summit, which I appreciate. And, you know, the feedback after that story, I mean, there were a few people who thought it was too harsh, but at least to me, it was overwhelmingly positive. And, you know, I think that was a story that needed to be told. I think I spent a lot of time, I spent a ton of time with Mark, which I appreciate him being so open with me. And, you know, I think it was tough, but it was fair.

Jess Mah: Yeah, I agree with that. I thought the way you articulated the story was very well-rounded. How about some of these other people you've spent time with, such as Adam Neumann? Do you have any reflections on what it's like to talk to people who are so iconic?

Ben Bergman: Well, you can't think of it as that, right? It's hard, especially with someone like Adam Neumann, who is larger than life. I mean, there's no tech person that's really talked about more. Well, probably Elon Musk, but certainly Adam Neumann is up there. And I watched the TV show about him, and I asked some of the people at SoftBank, I'm like, what is it like when I'm going to meet Adam Neumann? I just watched the show with Jared Leto, and they said he's even more charismatic and good-looking than Jared Leto. And it's true, he is even more charismatic. And I think it pretty quickly goes away that, oh, I'm talking to Adam Neumann. You have to treat it just like any other person and not be intimidated by someone, whether it's the Dalai Lama or, you know, Pete Carroll or Brad Pitt.

Jess Mah: How did you prepare? Like when you talked to Mark or Adam, just focusing on the business people you've interviewed, what is it like to come up with your question list? And how do you think about being different from the dozens and dozens of other interviews they've already had?

Ben Bergman: First of all, I read every interview they've done or watch every interview to see what they've talked about. Because I think hopefully one of the reasons people like it when I interview them is because I've done the research and also asked different things. So I try to find different things to talk about because a lot of times people just get asked the same questions over and over again. So I think it's really important to do your homework.

Jess Mah: But since these people have been interviewed so many times before, do you always have that confidence that you're going to be able to pull out some special nuggets that no one else has done before? Or do you worry about that? You're like, you know what? Like, this might end up being another boring article?

Ben Bergman: Well, I try to, and then I probably wouldn't publish the story because most of the things I do, at least until recently, were always behind our paywall. And so for someone to read something that I wrote, it had to be good enough that they would pull out their credit card and subscribe. So if I'm just writing something that everyone else has written, then no one's going to subscribe. And that's what I cared about writing.

Noah Berkson: Has it changed the way that you've done journalism in the last five or 10 years? Because now it is very different where someone needs to look at the headline and say, I'm going to pay to read that article, which I still think is crazy, but I understand that's the way to make money. Does that change the way you think about your writing or the way you think about interviewing?

Ben Bergman: Well, for sure, because, you know, for instance, like every startup founder, most of the ones who are coming up to me want me to write about funding announcements or things like that. And, like, there's just no way, unless it's like OpenAI or something, that I'm going to write about it. Just because that's everywhere. That's not what people are going to come to us for. So I really do have to look for those things that are unique, and that's why I spent so much time sourcing and talking to people. That's like 90% of the job is finding the story that no one else is.

Noah Berkson: So what's your end goal as a journalist? What's the kind of North Star that you want to orient to? Where you say a founder might want to build and sell a company or make tons of money, what are you orienting towards?

Ben Bergman: For me, my goal is always to write about what people are talking about, but has not been written about. So you mentioned the story on Upfront and Mark, and that was something that, you know, I'd heard for years, and no one had written about. And so those are the kinds of stories that I like. That stuff that is kind of known but no one's ever covered before.

Noah Berkson: And when you're reaching out to people for an interview, is a lot of that cold? Is that like cold reaching out, cold email, just from your Insider email, or is that warm intros? How does that work?

Ben Bergman: Well, it depends. I mean, if it's someone like Adam Neumann or something, that's going through their PR. But a lot of my work is reaching out to employees of companies. Right now I'm doing an investigation on a startup, and there I just reach out to employees on LinkedIn cold. It really varies.

Noah Berkson: Are people generally really receptive to that?

Ben Bergman: No. So I probably will do about 100 reach outs and maybe get two.

Jess Mah: Wow.

Noah Berkson: Wow. Are there any articles that you regret publishing as you look back and say, like, I wish I wouldn't have published?

Jess Mah: That, or you wish that you perhaps approached it in a different way? Maybe you're too negative, or you're too positive, and now you only realize that after.

Ben Bergman: I mean, no, I mean, I'm sure there have been ones that I would, you know, earlier in my career that I maybe, you know, look back on, and I'm like, that could have been better. I've learned so much. Or the benefit of hindsight, something else will come out. I can't immediately think of something, but I'm sure if I read it that I would regret it.

Noah Berkson: How much now do you think having a personal brand is important to your success as a journalist, as opposed to who you're writing for, who you're working for? But your personal brand, how does that play into it?

Ben Bergman: Well, I think it's immensely important as much as that word is kind of cringe, and it is. But I think having my personal brand on Twitter or LinkedIn or other stuff is very important because you see the biggest journalists of our time, at least in tech, are people who, you know, their names, like Taylor Lorenz, Kara Swisher, Alex Heath, I think much more than, you know, the outlets they're at. It's not as if everyone's going to The Wall Street Journal or The New York Times. And, you know, it's a very turbulent time in journalism and tech journalism. So I think the safeguard against that is having your own brand.

Jess Mah: Do you worry every month about missing out on the next big article or story? Are you thinking, wow, I haven't had a big hit in like three months. Maybe I lost my mojo. Has that ever crossed your mind?

Ben Bergman: All the time. All the time. Because this is such a competitive business. And it's also, you can see what everyone else is doing, and we all know each other so well. So when I see Kate Clark publishing a great story at The Information or Berber Jin and Tom Dotan, the story about the OpenAI funding, I'm like, God, I wish I would have gotten that. So that happens all the time. And you're only as good as your last story. I mean, I can be like, wow, that story did great. That did so well. But then it's like I got to write another one. And sometimes, you know, I'm like, what am I going to do? Although I will say when I was a more general interest business reporter, when I was at the NPR station here at KPCC, I would sometimes worry about what was my next story. But I feel like covering venture, there are about 100 stories I want to get to do.

Noah Berkson: You spend your day just reaching out to people just to see what you can get. Is that like the majority of your time spent? Is it just kind of putting feelers out to see what's out there? Or is it, hey, I think I have this hunch about this. Let me start to go investigate it.

Ben Bergman: It's probably a mix. I mean, when I'm working on a story, which is the best thing, that's like the place I like to be in and have a lead and getting far on a story. I'm reaching out to people with a very specific thing in mind. But also a lot of it is just coffee chats and catching up with sources, seeing what they're saying, seeing if they have any great tip to share.

Jess Mah: What are the metrics for success in a story?

Ben Bergman: Well, so they've recently changed at Business Insider, at least for me, it was all about the new subscribers that you would bring in. And we're very metrics-driven, unlike a lot of journalism organizations where there's supposed to be more of a firewall between that, and you're supposed to publish good stories and not worry about it. But we've always been more metrics-driven, but actually recently we just changed it to a new metric where we're judged on the amount of time our existing subscribers spend on stories. And I think that's a good change. But it's definitely changed the kind of stories that I do.

Jess Mah: I see. Could you talk about that some more?

Ben Bergman: Yeah. So like a lot of times I'll do stories that are not breaking as much, but a little bit more what people are talking about. So, for instance, I did a story on how VCs are seeing the election, and I wasn't really breaking any huge story there. Similarly, I did a story on Character AI and the string of kind of these acqui-hires that I wasn't breaking a big thing there like I would have been doing before, but I was doing more analysis. And those stories were very popular with our existing subscribers, but they weren't necessarily bringing in a huge number of new ones.

Noah Berkson: There was, as you say, there was Matt Taibbi who had that IRS visit because of something that he wrote. He had some negative press on the Biden administration or was kind of hurtful. Do you think about that when you're writing any pieces where you're like, this could actually be very negative for me, and I need to worry about the repercussions that this could have?

Ben Bergman: I really try not to. I try to let the chips fall where they may. And most of the time… I mean, I shouldn't say most of the time, but a lot of times I'm being threatened to be sued, right? And if I'm worried about that, like, that's not a great place to be. And I wouldn't write a lot of the stories that I've written. And I'm fortunate to have a great legal team and a company that is willing to stand up to me. If I didn't have that, I would be a lot more worried about it.

Jess Mah: Wow. So has Business Insider or any other entity you worked with been sued because of your articles? And what is that like behind the scenes?

Ben Bergman: Well, I don't want to jinx it, but, yeah, I don't think we've actually been sued. We get a lot of threatening letters, and they can look scary, but, you know, luckily our lawyers, you know, see through that, and we're, you know… But I don't think people understand the amount of vetting that we have to do behind the scenes for a story and also how many stories we work on for months that never make it into print.

Jess Mah: Wow.

Ben Bergman: Because our legal team feels that we don't have enough to go to print.

Noah Berkson: So they're really vetting every story before that goes out.

Ben Bergman: Yes.

Noah Berkson: How often does that… How often do they come back to you and say, hey, we need more here, or there's not enough done here, like, we can't publish yet. Is that a common occurrence?

Ben Bergman: Yeah, very common. Very common. Because they say, oh, well, you don't have, you know, the sourcing on this, or you have these anonymous sources. If this person sues us, that's probably not going to be enough to get us to win. So you need to get more documentation for this. You need to get more evidence for this. And, yeah, I've had a lot of big stories that have not been able to be released because legally they just aren't cleared. But I think we got to be aggressive, but we also have to be cautious in that regard.

Jess Mah: So even if you know who the sources are, if they're not willing to go on the record and have their name be published in the article, then it's not as valuable.

Ben Bergman: It is because… Or it's not because I wouldn't be able to give up the sources. And people always ask me that, if you're sued, will you give up? And I won't. So therefore, if I'm on the stand and someone's saying, how do you know this? And I'm saying, well, this anonymous source. And they say, well, who is it? I wouldn't say. So I think, legally, that does make it more difficult.

Jess Mah: I see.

Noah Berkson: To what extent would you go to protect a source?

Ben Bergman: I would go to jail for a source. I mean, that's what Judy Miller did at The New York Times. And I'm not covering national security, so it's a little different. But, yeah, I mean, I take that very seriously.

Noah Berkson: What is the key to asking good questions?

Ben Bergman: Listening. Because most people just have their sheet of questions, no offense, and they're moving…

Jess Mah: On to listen to anything on this list.

Ben Bergman: No, no, you got… No, but… And they just want to ask the next question. And it's the same when you're on a date or whatever. It's like you need to listen to the person, and that's what has the good questions. And also, I think Larry King famously didn't prepare for interviews, and that was his style, because he wanted to be the everyman. But I think you should be prepared and know what the person has done and where to go and what hasn't been asked before.

Noah Berkson: What's been the most embarrassing interview you've done, from the sense of you just realized you weren't prepared in that interview for what was going to happen, or you hadn't done the research, or you slipped up?

Ben Bergman: Well, I don't know. I mean, I don't think I've ever luckily done that. And the interviews I do now are very different, right? Because when I was doing interviews, when I worked in public radio, the whole thing would be aired like you guys aired. It's a podcast. So the questions you ask are sometimes very important, even if you don't get the answer. But for the questions now, I'm just trying to get information. And I think another key is just to keep asking the question until you get the answer. Because a lot of people don't do that.

Jess Mah: They just want to dodge, or they get distracted.

Ben Bergman: Exactly.

Noah Berkson: This friend of mine, Cal Fussman, he used to have breakfast with Larry King every day, famously. But he had this story about interviewing Mikhail Gorbachev, and he got this interview, interview with him, and it was supposed to be… It was an hour. It was an hour-long interview. And he gets there, and they're like, oh, wait, we, you know, it's maybe it's supposed to start at 1 PM, and they're like, ah, you got to wait a little bit. He's still behind. He's still behind. He's still behind. He's like, well, this is going to cut into the interview. And they're like, well, yeah, like he, you know, he needs to be done for the next meeting. The next meeting. And so he, they end up coming out and they say, hey, you have, you have 10 minutes. And he's like, well, 10 minutes, I need to interview this world leader, right? And he's talking about nuclear arms. And he's like, how am I? And I have to translate it. Everything I say is going to get translated to Russian and then get translated back. And he's brainstorming, okay, what do I ask him to try? And like, I need to get something from him. But, you know, normally you have five minutes of pleasantries when you start writing an interview. So he's like, I have basically like a couple minutes to do it. And he ends up kind of throwing away the script of what he was going to talk about. And he goes, what was the biggest lesson that your father taught you? And he asked him this question, and the guy translates it, and you just see him just kind of change his whole mood because it's not the question he thinks is coming. He thinks it's going to be something about nuclear arms and what he thinks about that. But he was like, that was really the key to a good question in an interview is how do you get kind of aim for the heart instead of aiming for the head. And I think, like you were talking about earlier, a lot of people when they get interviewed, they know the questions that are coming, and they're just have this like kind of recorded track ready to do that. You almost know the question. You know the answer that's going to come out of their mouth. How do you get people to open up when you're interviewing them in a different way than any other reporter?

Ben Bergman: Well, I think it's figuring out, you know, where they're coming from too. And it's different doing the kinds of interviews with famous people like Adam Neumann versus when I'm on a call with a source, right, which is really the most important thing I do. And getting people to open up is about understanding their motivation. So people always ask, why do people come to me? Because if you're an employee at a company, you've probably signed an NDA. So why would you talk to a reporter? And it's about finding their motivation. Do they have a story to tell that they think is important? Are they unhappy with the company? Do they feel that they've been mistreated? Maybe they're a competitor of the company. Maybe they feel like this is just a really important thing that they want to get out there. So it's about that and about listening and feeling like you're going to tell their story accurately and fairly.

Noah Berkson: And I imagine early on in your career as a journalist, you get a lot of access, and you get access probably in a different way than most people get access to important people, powerful people, political figures, whatever that is. Did you feel a lot of kind of imposter syndrome when you go in the room with somebody, and you're probably fresh out of your, you know, you're fresh in your career or young in your career, and in no other way would you both be in the same room having a conversation?

Ben Bergman: For sure. I mean, that would… It still happens a lot. I mean, just like the people I get to meet, and I'm like, how do I get to do this? And who am I talking to? This person? Or even when I did the Columbia fellowship, we had a two-hour dinner with Jamie Dimon, and I'm obsessed with credit cards. So I'm quizzing him about the Chase Sapphire and how it makes money for them. But again, it's like seeing everyone as people and not being intimidated by people. I think the only person I really kind of clammed up on is when I got to interview Pete Carroll after they won the Super Bowl, because I'm from Seattle, and I'm a huge Seahawks fan, and that was the only one where I got a little tongue-tied.

Noah Berkson: Is there anyone today that you have not interviewed you really want to interview?

Ben Bergman: There's a lot of people. I mean, I think for everybody, tech journalist like Elon Musk is sort of the Holy Grail, although he's certainly out there a lot. So I'd probably be, I think, Jeff Bezos, I'd really want to interview because he doesn't do a lot of interviews. And I think he'd be so interesting. And I'm from Seattle, seeing the rise of Amazon.

Noah Berkson: If we were going to brainstorm this right now, how you get that interview with him, how do you go about that?

Ben Bergman: So, yeah, it would be reaching out to his people and being like, okay, I know you don't do any interviews. You're on your giant yacht and building your space company. But here's what I can offer you. I've watched your company since the beginning. I literally grew up next to you. And I'm interested. And here's what I can provide. Because for people like that, he can go anywhere, and someone like Adam Neumann can go anywhere. So why is he going to go to me?

Noah Berkson: What can you provide? What could you provide to Jeff Bezos right now that he can't get elsewhere?

Ben Bergman: Well, hopefully he's listening. I would just, again, like being there in the shadow of Amazon and understanding the company so well and able to convey that. But I don't know, it's probably not a great pitch, so that's probably why I haven't landed.

Jess Mah: Here's another idea. To what extent would you be willing to actually shadow him for a month? If that was the terms, you had to be 24/7 with him for a month, and then you could write about him. Would you do that?

Ben Bergman: So I'd have to be on his yacht in the south…

Jess Mah: Everywhere.

Ben Bergman: Okay, that sounds terrible in the twin…

Jess Mah: G550, but you have to drop all your other stories and work for a month. Is that a sacrifice you would make? Have you had to make any sacrifice like that where you spent a whole month or even three months just on one story?

Ben Bergman: Well, yeah, as far as the first question, yes, I would drop everything to go meet him. And I think oftentimes that's how you get to know someone. You know, when you're writing a profile, you want to see them in action, right? And because people themselves aren't usually that able to talk about themselves. When I write a lot of profiles, and usually the most interesting stuff I get is not from talking to the actual subject of the story. And a lot of times the best profiles, they don't even get access to the person. So it's about talking to people they've worked with or known for a long time. But spending time with them is immensely important. I haven't had to drop everything for a story, but there are stories that I've worked on for six months or a year, along with a lot of other stuff. But a lot of the stories I do take a long time, and a lot of it is because of all that legal review, where I'll have to keep going back and keep working on a story.

Jess Mah: But what if you have the subject, like in this case, Jeff Bezos, on your side and helping provide, you know, other people you could talk to, and they're obviously supportive. Would that make it easier, actually, for you to get this ad in three months or two months?

Ben Bergman: Yeah, that would definitely make it easier. But I would also have to talk to other people as well, right? Because, you know, I'd want to talk to, you know, because when someone gives you people to talk to, they're probably going to be, you know, friendly, and you definitely want to hear that, too. Yeah. But you also maybe want to reach out to people who've not had a…

Jess Mah: Great experience and get a full, well-rounded view. But then how do you paint that picture of like, hey, I want to give you a great profile, Jeff, and therefore you're going to invite me on your yacht and to fly around on your jet with you to shadow you, but at the same time, I might try to pick up some dirt on you at the same time. That'd be very difficult for them to wrap their head around, for sure.

Ben Bergman: And I think that's why most of the stories I do don't involve that level of cooperation, because that's access journalism. And that used to be more common because it was like, oh, Steve Jobs, we're going to put you on the cover of Time magazine. And so we're probably going to be more friendly, but now that's not that important. And most of the best stories do not come from access. They come from sources and getting the information. And then once you have the story, the person would come in to give the interview, because they have to. But I worked on a very long story. One of my first stories at Business Insider was about Whitney Wolfe Herd, the co-founder of Bumble. And so I talked to a lot of former employees and people she'd worked with, and she never spoke to me for the story. They did answer a lot of questions via email, but I never spent time with her.

Jess Mah: Do you think that the story would have been considerably different, perhaps even more positive on her, if she had cooperated?

Ben Bergman: I do. I mean, I think there's usually a benefit to people providing access because it usually just makes you more sympathetic as a reporter when you spend time with someone. And I think everything is in shades of gray, and when you talk to someone and find out their motivation, you're just naturally going to understand them better. And I think that will be reflected in the story. So I think… I think the story I did on Mark benefited him as well as me, from him spending a lot of time with me.

Jess Mah: Yeah. So then what percentage of the time do they cooperate versus decline and answer very shallow answers via email?

Ben Bergman: I think with most of the bigger stories, they will cooperate eventually, but it can take a lot of wrangling. And I think they have to see that you're serious and that you're going to do the story with or without them, so they might as well cooperate.

Noah Berkson: I was going to ask, do you ask a lot of times for introductions from the friends that you've made through this and say, hey, will you introduce me to Jess? Because I want to interview her or do a story about her? Do you use those, or is that kind of like off limits? I don't want to ask.

Ben Bergman: No, not usually, because I probably would just reach out directly to the person or to their PR people, or a lot of times the PR people will reach out to me because they'll have people forward the email to them. So they'll just say, hey, what are you doing? Can we help? And I say, well, I'm not quite ready, but I'll let you know before we publish the story.

Noah Berkson: Yeah. Who would be the person you'd go to if you wanted this Jeff Bezos interview? Who would be the person to try and get that introduction if you had to name one person that you would go to to ask?

Ben Bergman: I don't know. Well, you know, Andy Jassy actually lives on my block in Seattle, so maybe I could knock on his door and…

Noah Berkson: Ask him, would you be as bold as to do that?

Ben Bergman: Probably not, but maybe I should be. I mean, you know, fortune favors the bold, right?

Jess Mah: Yeah, exactly.

Ben Bergman: Yeah.

Jess Mah: Would you want to transition towards doing longer-form journalism or perhaps even writing biographies and books on subjects, or would you prefer just doing what you're doing today, long-term?

Ben Bergman: You know, I really like the mix of what I do because I always have a couple long-form features I'm working on that take six months or a year to do. But I also, I'm a beat reporter, so I'm covering day-to-day VC for now, though. For now. But I do like that mix. And I also think, frankly, it makes me more valuable because there are a lot of very good feature writers, there are fewer good VC reporters.

Noah Berkson: You host this poker game. You're really into poker. Has poker taught you anything about journalism?

Ben Bergman: Well, it's taught me a lot about life. It sounds like a cliché, but I think it's true that poker is just, in terms of, assessing risk versus reward. For instance, I thought about it when I was applying to that fellowship at Columbia. I was like, there's a small chance that I'll get this. So I'm putting in all this effort and money into getting into the program. And I had actually tried a couple times, but if I get it, it will be this huge payoff. And I think that's the same way you think about poker because you have a 30% chance of making a flush when you have two of the same suit. So it's still a low percent, but it's a big payoff if you make it. So you're willing to put quite a bit of money into the pot. So for sure. And I think poker just attracts friendly, interesting people. And if someone asks me to hang out, and I say, great, do you play tennis or poker? If they don't, it's probably not going to work out.

Jess Mah: Both of them are in-person activities. Poker, you're essentially reading your other participants with journalism. How important is it for you to meet your subjects in person versus on Zoom versus just do a telephone call?

Ben Bergman: Well, yeah, I mean, everyone wants to do Zooms, and I really do not like Zoom meetings. I think for me, I just get very little value from Zoom meetings. They were great during the pandemic, but it's just, it's very stilted, and you're not really going to get, you know, where you get stuff is, you know, when you're at a coffee shop or doing a walk with someone or, you know, at an event, and they mention something. So it's not great. The phone is better than a Zoom because people are a little bit more casual, they'll open up a little bit more interesting. Zoom is so formal.

Jess Mah: Wow.

Noah Berkson: Did you think that business school was really valuable for you?

Ben Bergman: It was, I think for one thing, like learning the mechanics. Because I did politics major in undergrad, so I had no idea about corporate finance, accounting. So doing those… Not that I could do a discounted cash flow if you asked me to right now, but just sort of like having that confidence and knowing that background. But the most important thing was meeting people and just being around really smart people from there. And that just opened up a whole other world for me. And I knew that I wanted to cover business instead of just be a general interest journalist.

Noah Berkson: So you're saying that meeting the people at Columbia was a better network than the network that you get every single day or the access that you have to everybody?

Ben’s approach to building sources echoes the relationship-building principles I discuss in The Human Skills That Make Us Irreplaceable.

Ben Bergman: Well, I wouldn't necessarily say that. I mean, being a VC journalist now, I really do meet such great people. But as you know, and now some of the best people I meet really are through tennis and poker. So it's all great. But yeah, I mean, that Columbia network is great as well.

Noah Berkson: If you were going to be doing something else, and you had to leverage the network that you've built today through journalism, what would you be doing?

Ben Bergman: Well, I mean, the easy answer would be be a VC, right? A lot of people make that transition from journalist to VC, and I think it's a similar skill set, right? Because your network is so valuable, you're getting information that people don't have, and you're also telling stories.

Noah Berkson: So I'm thinking about this, like, Dot LA was kind of that, right? They had some or like an investment arm, I think, Sunnyside or something that was tied to LA. So it was like, hey, we not only invest in you, but also promote you. Does that model work?

Ben Bergman: Well, I mean, 75 and Sunny is Spencer Rascoff's family office. So completely separate from Dot LA. You can't do both at the same time, right? And at Dot LA or Insider, I'm not allowed to invest in companies. I'm not allowed to take any consulting fees, I'm not allowed to be paid for stories. Because I really think if you're doing journalism, it has to be about the story. And once you start mixing them, it's not journalism anymore.

Noah Berkson: Do you think you would make a good VC?

Ben Bergman: I think so. But I think the difficulty for me, though, would be that I tend to look at a company, and I'm like, how the heck is this going to succeed? There's 50 competitors. There's all these obstacles. Here's what can go wrong. VCs have to be very optimistic. They have to be, okay, this will be the next Uber. I definitely don't think I could be a startup founder. I'm around startup founders all the time, and I respect them so much, but that is not the mentality I have. And actually, there are also journalists like Eric Newcomer, who've gone into a more entrepreneurial track, starting their own Substacks. I like being at a company where I have that salary. I have the benefits.

Jess Mah: You have a legal team.

Ben Bergman: I have a legal team. And I know if I don't have a great story for two months that I'll still have a paycheck coming in and can make the rent.

Noah Berkson: You've been here for five years now in LA. What has dating been like?

Ben Bergman: Oh, wow, that's a turn. You know, it is… It's great. I mean, I enjoy dating. I think a lot of people say how horrible it is, but since I love meeting people, right? I think that it's usually fun for me. And there's very few dates I go on that I'm like, oh, you know, I wish I wouldn't have gone on that. I definitely think dating in New York is better, at least for guys, but it's good here as well.

Jess Mah: So when you and I met on Hinge, I didn't know this, by the way.

Ben Bergman: Yes.

Noah Berkson: Just for context, Jess, Ben's gonna come on the pod. She's like, wait, I think I went on a date with him, and I…

Jess Mah: Didn't get asked out on the second date. What the hell?

Ben Bergman: Well, yeah, let's do it. You were flying off. If you had to rate this date…

Noah Berkson: What was, like, a scale of 1 to 10, what would that be?

Jess Mah: Brutal. And then what's your negative feedback for me?

Ben Bergman: No, no. I actually… I would have loved to, or still would love to go out on a second date with you, but you were… You know, it's tough. Dating is very, like, immediate, right? And… And it's tough when you're going out of town, and you were, you know, leaving, right? Yeah. And… But we had fun. We had lunch, right? We went to Earth Cafe.

Jess Mah: Yeah.

Ben Bergman: We went to Earth right before New Year's, and then I was gone for a month or two.

Jess Mah: Yeah.

Noah Berkson: So to bring this full circle, we made this whole podcast just to get you on here so Jess could ask about why you didn't ask her.

Jess Mah: I know.

Ben Bergman: We've been sitting here…

Jess Mah: We're really trying to make more dating prospects for me.

Ben Bergman: Yeah, no, I mean, we've been sitting here talking about sourcing and startup valuations, and now you get to the…

Noah Berkson: We get to the fun stuff.

Ben Bergman: Yes.

Jess Mah: It's like… It's… For me, I have met so many incredible people from just dating them that I think so much of my business success has come from just that. If I'm being candid, that is one of the best advantages to being a woman in business. Is that the case at all for you? Has it?

Ben Bergman: You do not hear that very often. Wait, so how do they help you?

Jess Mah: Because I meet very interesting and accomplished, successful people through dating, and because of that, I get to ask them interesting questions. Just like what we're doing right now.

Ben Bergman: But is it… But, I mean, do you… But sometimes it's like a mix, right? Or it's weird to mix them if you're, you know, go into business with them or…

Jess Mah: No, I don't do business directly with them, but I learn from them.

Ben Bergman: Okay. Okay.

Jess Mah: And then I hear all the inside secrets on their life and what really happened. Because a lot of these people are very high-profile. I mean, I think I've dated five, six billionaires.

Noah Berkson: Wow.

Ben Bergman: Okay.

Noah Berkson: Well, no wonder I've been written about.

Jess Mah: And I'm like, so, what's the actual secret here? What actually happened behind the scenes? And I hear the real stories, and I'm like, wow, no journalist has been able to cover this and has any intel here. And, of course, I'll never leak it. I treat it just as sensitively as you treat your anonymous sources. And I promise full discretion, because the stuff I've heard and know about from these people, it's just, like, it will blow your mind. And how could you create that without having to sleep with them?

Ben Bergman: But what happened to these billionaires? They sound great. No, I didn't want to hear those stories.

Jess Mah: Well, some of them are still around.

Ben Bergman: Yes. So what was the question?

Noah Berkson: What would your… Like, how could you do that today? Or, like, how could you leverage this network of people you have in maybe a different way than you're doing it? Maybe just to learn more about business, learn more about how these people operate? Maybe not for a story, but just more to learn. Like, do you leverage a network in that way or reach out to people in that way?

Ben Bergman: Yeah, I mean, I try not to think of it as, like, leveraging, but again, yeah, it's, like, always being curious. And one of my powers, I think, is my network and connecting people and knowing so many people, and I think that's tremendously valuable, bringing people together.

Noah Berkson: How many people do you just reach out to? Not because you want to write a story about them or because it has something to do with your job, but just because you're like, hey, I want to meet these people. They sound interesting. And… And given the position you have, you have good access. And probably most people would be like, yeah, I'd love to grab a coffee with you.

Ben Bergman: Probably not. No. I mean, if I'm reaching out to you, it's probably for a story or because you're a good tennis player or poker player. Yeah. Very few. If it's just like, oh, I think you're interesting. Very few. And, yeah, I mean, as far as what you were saying about the dating, too, I mean, I definitely… If I see someone on Hinge or Raya is a VC, of course I'm like, oh, that's interesting.

Jess Mah: Double duty.

Ben Bergman: Yeah. But I try not to do that to, like, make people feel like I'm interviewing her.

Jess Mah: Well, you're not actually attracted to her. You're not gonna go on a date just to see if there's any business…

Ben Bergman: Yeah. Or people are like, oh, are you gonna, you know, write about what I say? Or, you know, like, you know, write a story on what… You know, if I'm going out with someone from like SpaceX or something, I'm naturally like curious. So that is, you know, what I'm gonna talk about. And I probably gravitate towards people in tech, so a lot of people are in it, but I definitely wouldn't want to be seen as doing that.

Jess Mah: You have a very good Hinge profile, by the way.

Ben Bergman: Oh, really?

Noah Berkson: What makes it good?

Jess Mah: His photos show him in like very different contexts, and he's got some great, great photos that show his professional side, and, you know, they're all very happy, smiley. They're not too serious. They're just him. It's not like 10 other people in the photos. And I don't know, it's just a great profile. I remember out of the tens of thousands of profiles I've probably seen, his is definitely a top five or top ten.

Ben Bergman: Wow.

Noah Berkson: Wait, who opens on Hinge? Is it the guy that opens, or is it the girl, or anyone can open?

Ben Bergman: Either one. Either one.

Noah Berkson: What's your opener?

Ben Bergman: I usually try to not have, like, a line because I think that, you know, some people have this, like, catchy line, and I'm like, okay, well, I'll…

Jess Mah: Go on and see…

Ben Bergman: They just say it. The catchiest line.

Jess Mah: What did Ben say on him?

Ben Bergman: No, but I try to make it organic and, like, about something specific on the person's profile.

Jess Mah: I think with the messaging was very good too.

Ben Bergman: Well, yeah, because I think it was about your jet. That's what caught my eye.

Jess Mah: Oh, I took those photos out eventually.

Ben Bergman: You're attracting… Yeah, but I think that that's what I opened with. But I mean, I'm glad I had a good profile, but hopefully I always want to undersell and overdeliver because there's some people who have a great profile, and then you meet them, and it's so disappointing. So I hope that…

Jess Mah: Well, hey, we're still here. We've been talking for a while, and it's just like we could talk for hours.

Ben Bergman: We could, yes.

Noah Berkson: One of the things I wanted to ask is, like, you mentioned an article. You said that I love to be a journalist because… Because it's like having this front-row seat to history, which I really liked. What do you think right now? Or that maybe you've covered in the last year or right now, looking forward, what are those things that we're going to look at in the next 20 years, 50 years that is going to be looked at as history?

Ben Bergman: Well, yeah, I mean, I think the obvious answer right now is AI, and it just happened so suddenly. I mean, I remember I came back from a ski trip last year in Japan, and I felt like when I came back, like I was gone for two weeks. Like, all of a sudden, it's all anyone was talking about. This was like February of 2023.

Noah Berkson: Niseko. Yes, I was there in February 2023.

Ben Bergman: Really?

Noah Berkson: Okay, that's… Wow. Should have crossed paths.

Ben Bergman: Yes, we should have. And… But, you know, that is another reason why I love tech too, because it kind of feels like the center of the universe sometimes. And I think it's undercovered relative to a lot of other things. And there's just so many interesting things happening right now for AI. And I think it has a lot broader applications than the big crazes of the past few years, which were like crypto and Web3, which were pretty niche. But I just think AI we will be looking back on this period for a long time.

Noah Berkson: Do you feel like there's anyone, like reporters that don't respect the coverage of venture and of tech that kind of look at it as, like, that's not… What's the important thing on the hierarchy of journalism?

Ben Bergman: Oh, for sure, for sure. There's a lot of that. And look, I recognize that. But there are far more important things in the world. I mean, there's reporters who risk their lives every day covering wars and conflict zones. And we need reporters to cover the school board and the county council. And those things don't get the same sort of resources as tech journalism. And I'm spending my time on yachts and fancy parties with VCs. So I definitely, I get it. But I also think what I do is very important. I think tech is important. I think tech journalism used to be very fawning. It was like, oh my God, Steve Jobs, the iPhone. Look at this cool new product. And then it got very critical, and it was like, we're going to tear down this company. And I don't think either approach is good. I hope we find more of a middle ground because I always try to be critical, but I don’t want to be a reporter who… I think there are reporters who just think anything a tech company does is evil or capitalism is evil. And I definitely don't think that. I think, again, it's those shades of gray.

Jess Mah: Do you think you might get tired of tech journalism, though? Like 30 years from now? Will you be interested in pivoting and trying some other types of journalism?

Ben Bergman: Well, it's hard to say. I mean, I definitely am not tired of it because I just feel like, it's always something new and a new challenge and a new story to tell. But you'll have to have me back in 30 years.

Jess Mah: Okay.

Noah Berkson: Lastly, have you had any dates off of this? I'm just thinking about this. Have you had any dates where you've went on a date, and someone's just tried to kind of pitch you? Like, you realize that their whole going on a date with you is to kind of, like, pitch you to tell their story of their company?

Ben Bergman: Luckily, I don't think I've had that. I try to… I mean, for one thing, like, I don't think most people would know, like, who I am. I don't put that, like, exactly where I work or what I do on my profile.

Noah Berkson: And you still swiped on this?

Jess Mah: Yeah.

Noah Berkson: No context.

Jess Mah: Yeah, I didn't look him up ahead of time or anything.

Ben Bergman: Wow.

Jess Mah: I just went in totally blind.

Noah Berkson: I feel like those are the power things people put, like, here's what I do as the way to lure people in.

Jess Mah: I mean, I knew he was in journalism because he had some photos, and I think said something about that for a long time.

Ben Bergman: Yeah. But I keep it vague. You know, I don't have my full name. I don't have the publication. And dating apps generally are not the time to be modest. But, you know, you don't want to, like, put it all out there. And, you know, I remember, like, for a while, I had a clip of me on CNN, but that was, like, too much. So I try to, like, have enough to get them to go out, but not, like, just put it all out there.

Jess Mah: So no photos of you with famous billionaires on yachts and…

Ben Bergman: No, no, I'm not putting my Gulfstream…

Noah Berkson: Ben, this has been awesome.

Jess Mah: Yeah.

Ben Bergman: Thank you so much.

Noah Berkson: Really appreciate you coming. This is fun.

Ben Bergman: This is really fun.

Here's a summary of what we talked about.

• Lucy’s Early Hustle & Entrepreneurial Spirit: Even as a kindergartener, Lucy was finding ways to make money—selling Pokémon cards, colored pencils, and eventually building a virtual pet site with free labor from artists she recruited off DeviantArt. That scrappy, creative hustle never left her.
• Her Unconventional Path & the Thiel Fellowship: Lucy dropped out of college after receiving the Thiel Fellowship, defying her strict parents' expectations. They were devastated at first, even emailing her obsessively to convince her to return to school—emails that eventually got flagged as spam by Gmail.
• The Real Origin of Scale AI: Before building Scale AI, Lucy and her cofounder tested wild ideas—like “ClassPass for clubbing” and a homemade food delivery platform that ran into legal issues. Eventually, they pivoted to data labeling for AI, with lidar labeling as their breakout innovation. She built the first version of what became Scale’s core in just a weekend.
• Building Passes & Dominating the Creator Econom: Now, she’s focused on Passes, a monetization platform for creators, which she started without a deck or name—just by texting LPs. It’s grown fast, is cash-flow positive, and serves creators earning six figures monthly. She emphasizes emotional retention over product retention when working with talent.
• Raw, Real & Unfiltered: Lucy is unapologetically herself—frugal despite wealth, obsessed with Barry’s Bootcamp, loves spicy food, and doesn’t shy from controversial takes. She shares openly about everything from dating and being targeted by escorts, to being robbed, to why she wears cheap clothes now despite owning a $20K cat.
• And many more.

Video

Watch the full conversation on YouTube here.

Or watch below:

Full Transcript

Lucy Guo: One day in San Francisco, I was riding an electric longboard and I broke my jaw. So I couldn't eat for, like, two months because I somehow convinced people to work for me for free. So it's always, like, been in me, I think, because I had this, like, idea of, like, businesses and how to make money. I enjoyed making them mad, though. But I got the Thiel Fellowship, right? And I was like, okay, well, like, if I accept this, then, like, you guys are gonna get very mad at me. Haha. Let's do it. I think when I started working at Snapchat again is when they were like, oh, okay, cool. Like, you're successful.

Noah Berkson: Lucy, welcome to the pod. We're so excited to have you. Could you give a really quick tell people who you are?

Lucy Guo: Cool. Hi, everyone. I'm Lucy, founder, entrepreneur, investor. I'm most known for doing a lot of Barry's Bootcamp, though. Pretty much I've been in tech my entire life. And yeah, I think that's a good TLDR.

Noah Berkson: You're known for doing Barry's every morning, like a ritual. You do double Barry's?

Lucy Guo: Yep. I got the 6:15 and 7.

Noah Berkson: 25 AM every single day?

Lucy Guo: Yes.

Jess Mah: Wow.

Lucy Guo: I will say, like, sometimes Saturdays, I give myself a rest break, like a rest day. But, like, you can pretty much count on me there, like, Monday through Fridays.

Noah Berkson: Where does this come from?

Lucy Guo: Oh, it's actually kind of funny. So one day in San Francisco, I was riding an electric longboard and I broke my jaw. So I couldn't eat for, like, two months. Right. So I decided that because I couldn't socialize or eat, it was my time to finally get hot and get abs. So I basically signed up for ClassPass, started doing Barry's, and realized it was my favorite workout. So I got, like, you know, the monthly membership, and then, like, the number of Barry's classes I was doing was increasing. And then by the time my jaw was healed, I was just addicted. So it's pretty much continued since then.

Noah Berkson: And you can operate. It seems like you are a late. You're, like, a night owl of a person. You're able to be out late and then go to Barry's and still be functional every day and be as high energy as you are.

Lucy Guo: I mean, I would say, like, I prefer to get five to seven hours of sleep. Like, if I have to get three to four, I will get three to four. And, like, I believe in discipline and that, like, once you, you know, break a habit, you make excuses. Right. So for a long time, actually, in Miami, I was only doing one Barry's a day because in my head I was like, okay, it's okay to do one Barry's a day because I want to get to the office earlier. And I basically had this free car service that started at 8 AM, so, like, the earliest Barry's I could do is eight. So yeah, I made an excuse. I did it. And it took me a little bit to, like, get back into my two a day. So I don't really want to, like, fall back in there. So no matter how tired I am, I just, like, force myself to do it so I don't make excuses to skip it in the future.

Jess Mah: Stepping back, you've been super successful as an entrepreneur and as an investor. Where did you, where did this all come from? Like, were you high-performing when you were a kid growing up, or were you a slacker?

Lucy Guo: I would say it probably comes from, like, Asian culture. My parents always emphasized having money or making money and saving money.

Jess Mah: So were they poor, rich?

Lucy Guo: I would call them middle class, but acted like they were dirt broke. But we were definitely, like, I would say, like, middle class. So, like, in kindergarten even, I was figuring out ways to make money from, like, selling Pokémon cards, trading them up, selling colored pencils, etc. I got sent to the principal's office a bunch of times.

Jess Mah: What's wrong with that?

Lucy Guo: Also, what's wrong with that? Because I guess I wasn't allowed to, like, do that. And I wasn't, you know, like, I was just bored in school. And this kind of continued, like, throughout elementary school, high school, etc. Like, in elementary school, I have no idea how, but I convinced someone, like, to do free engineering and free design work for me. So I created my own virtual pet site, which is, like, honestly kind of sick because I somehow convinced people to work for me for free. So it's always, like, been in me, I think, because I had this, like, idea of, like, businesses and how to make money.

Jess Mah: That's.

Noah Berkson: What is this virtual pet site?

Lucy Guo: I don't even remember what it's called. I think I went through two different names. Like, one of them was, like, SVYT. I, like, recruited artists off of DeviantArt, and I don't even know.

Jess Mah: Like a virtual Tamagotchi thing.

Lucy Guo: Yeah. And then I went through a different name change. I don't remember. But I remember I had found the artwork on DeviantArt one day, like, randomly. And I have no idea how I got them for free.

Jess Mah: But you started really young, which is, I think, the only way you see world-class entrepreneurs start. Like, even in my case, I was selling traced drawings on a playground when I was in second grade. Got in lots of trouble for that. And, like, I had one kid pay me 100 bucks for something I traced in, like, you know.

Lucy Guo: Oh, that's kind of amazing.

Jess Mah: Yeah, that was great.

Noah Berkson: But did you get access to a computer super young?

Lucy Guo: I did. I don't remember what age I got access to a computer, but it was pretty young. Like, I would say, like, probably preschool, kindergarten era. Yeah, I would go to the library and just, like, hang out on the computers too.

Jess Mah: But why, why did we end up as entrepreneurs and investors when so many of our Asian peers with the strict Asian parenting, they ended up in kind of boring, mediocre jobs?

Lucy Guo: Well, I think that I don't know if I call those jobs boring.

Jess Mah: Not to be an asshole, but, like.

Lucy Guo: But, like, it's exciting. Yes, I would say that. I would. We're probably more risk-oriented because, like, you see these Asian parents, like, the stereotype is you need to be a doctor, you need to be an engineer, you need to be a lawyer. And these three things are, like, you know, high-income jobs that are very stable. And most kids listen to their parents, and they end up going to these different paths in life. My parents basically disowned me when I became an entrepreneur.

Jess Mah: Oh, wow.

Noah Berkson: Tell us about that.

Lucy Guo: Yeah, I mean, they just got really mad. I enjoy making them mad, though. But I got the Thiel Fellowship, right? And I was like, okay, well, if I accept this, then you guys are gonna get very mad at me. Haha. Let's do it. So I ended up taking the Thiel Fellowship, and they were just extremely upset. And I get it. 'Cause, you know, education gave them everything that they have in life. So for them, it was almost like me saying, like, I don't, I don't respect you. I'm throwing away everything you gave up and immigrated from China to America to give me to, like, be a dumb kid. Right?

Jess Mah: Yeah.

Lucy Guo: So that's when they stopped talking to me for a while.

Jess Mah: And, like, for years you guys stopped.

Lucy Guo: I think when I started working at Snapchat again is when they were like, oh, okay, cool, like, you're successful. Because I was getting, like, paid pretty.

Jess Mah: Generously because they were worried that you'd be, like, a homeless bum and disappoint the family.

Lucy Guo: But they were still reaching out to me. Like, it turned out my dad was emailing me constantly to the point where Gmail was marking it as spam. So I later discovered it because it was pretty much, like, you know, there's, like, all caps, "GO BACK TO SCHOOL." Like, "YOU'RE GOING TO BE A FAILURE. I'M GOING TO BE HOMELESS." And, you know, Google, like, Gmail thought they were spam emails. So they were still reaching out to me, like, trying to convince me and, like, put me back on, like, what they thought was the right way.

Jess Mah: I mean, they really cared about you.

Lucy Guo: Yes, exactly.

Jess Mah: This is all just real love.

Lucy Guo: Exactly.

Jess Mah: Comes out in a weird way.

Lucy Guo: Yes. It was their way of showing love.

Noah Berkson: Did the Thiel Fellowship not have somebody that is, like, the person that talks to people's parents? Because I assume this situation happens all the time with people that accept that, and it's, like, kind of gives them some comfort around what their child is doing. Like, they're dropping out to go do this, or they're leaving to go do this.

Lucy Guo: I would say the Thiel Fellowship probably had people that were willing to do that. I don't think my parents would have had a conversation with them, though.

Noah Berkson: Wow.

Lucy Guo: Yeah.

Noah Berkson: Wow. What was that fellowship like?

Lucy Guo: I would say the pro of it was just that you got money, like, with no strings attached. Right. Like, you had ultimate freedom, and you had really smart peers around you. I would say, like, the support system, at least for me, was more so the peers. I got to meet some of the most incredible people that I still know today. Right. But it was very independent, I would say.

Noah Berkson: Was there an idea you came into it with?

Lucy Guo: I did not really come into it with a real idea. I used, like, a hackathon project that I had done the week before when I submitted my application.

Noah Berkson: Was that something you continued to work on?

Lucy Guo: No. What I ended up doing for the Thiel Fellowship was, like, a two-sided marketplace where people would, like, make food, like, homemade food, and deliver it, which ended up, like, people are making good money, $100 an hour, you know, like, there was a sorority that, like, launched with it and made $5,000 in the first day, but turns out it's actually really illegal to do this. Like, food safety issues. So. Yeah.

Noah Berkson: Did that end up getting shut down? You just stopped doing it. What was the ending of that?

Lucy Guo: I stopped doing it. I think that there was just a lack of passion for the project along with the fact that, like, we had come across the food safety issues, and we're, like, at that point in time, you need, like, a centralized food kitchen to be able to do something like that. I think laws have recently, like, changed over COVID. So, yeah, I just ended up going to take a normal job for a few years.

Noah Berkson: What was that? I mean, what was that like going from kind of building your own thing, doing your own thing, to now going into, I assume, a much more structured and defined role?

Lucy Guo: Yeah, I mean, I think I got to learn a lot in these structured roles because I got to work with people that have had several more years of experience. So I ended up going to Quora and then Snap. And I also got a feel for, like, just the different cultures because they are, like, they could not be more opposites. And I learned what I liked in each culture and how I would imagine I would like the values I would have for my own companies in the future. So overall, I would say good experience.

Noah Berkson: Were you thinking like that at those companies? Were you thinking, like, how do I take away some of these values or the culture for my own thing? Was that in your mind, like, hey, I'm gonna go do my own thing again, but this is just a learning experience, or how were you viewing it?

Lucy Guo: I was definitely viewing it as a learning experience, especially 'cause, like, I wanted to actually ship a project product and see, like, the long-term impact, which I actually got to do some really cool things at Quora. I was running a lot of A/B tests, and these A/B tests were, like, that's where I learned that, like, by changing, like, one word, you could increase, like, conversion by 30% on signups. Like, I was seeing pretty crazy numbers based off these A/B tests I was running, which is really cool. I moved to Snap, and, like, I remember I mentioned the word A/B test, and it was, like, a banned word basically. They're like, don't mention the word A/B test here again. And I was like, super different. I think that they care more about things as a whole versus, like, okay, cool. Everything is a formula, and you fix each little part, and then it solves the product. Right. And it was a totally different way of thinking. But it was really fun seeing just, like, I think how much of a visionary Evan was. That was something that really surprised me versus I think that Quora the team was much more, like, mathematical and calculated versus Snap is very visionary, creative, etc.

Jess Mah: It shows that different cultures could work, and they're successful in different ways.

Lucy Guo: Exactly, yeah.

Noah Berkson: And you went to Quora originally because you were an avid Quora user.

Lucy Guo: Yep, I was an avid Quora user. I was, like, basically asking questions that a VC would ask, which is, like, hey, what's your monthly active users? Daily active users, like, month-over-month growth, retention, etc. At some point, they got very annoyed. I do think that they mixed up monthly active users with page hits when they gave me the number, but that's a whole other story.

Noah Berkson: And then at Quora, you meet your co-founder, your future co-founder for Scale AI. How did you guys build a relationship?

Lucy Guo: Yeah, I mean, we would just eat lunch together. He was, you know, another young kid that was working full-time. So it was just very natural. Yeah.

Noah Berkson: Was that a pretty fun place to work? Was it a lot of younger people? Like, was the engineering team pretty young?

Lucy Guo: I would say. I don't really remember if the engineering team was young per se, but I would say it was very talented. Like, it was, like, where some of the best engineers in the Valley went? I think there are a few companies that were just known to have good engineers. Like, Quora was one of them. Dropbox, Palantir, etc. And I think that I ended up choosing Quora partially because I used the product, but partially because the engineering was just so highly respected there.

Noah Berkson: And at what point do you go, hey, we're going to go start a new company? Tell us about that. What was that like?

Lucy Guo: Yeah, I was at Snap, he was at MIT, and we had always thought about building a company together. I think it was literally over winter break we started working on side projects because I was just getting the itch again to start something. And YC apps were coming up, I think, the following year. And then, yeah, just kind of happened.

Noah Berkson: What was, what was the original premise for the business?

Lucy Guo: I mean, the first thing we built was ClassPass for clubbing. Very dumb idea.

Jess Mah: That was the first business ClassPass for what?

Lucy Guo: ClassPass for clubbing. Then we immediately pivoted.

Noah Berkson: What was. Yeah, back up. What was the idea? Like, give us the. What were you thinking at the time?

Lucy Guo: In our heads, I was like, okay, cool, you'll pay this monthly membership fee of, like, let's call it $40 a month. And then we could just get promoters to bring you to clubs for free. So it's no cost for us. And there's so many promoters and, like, you know, there are clubs that are offering free drinks to get people through the doors, and we can make it seem like this cool thing, but, like, not well-networked people wouldn't know about it. But then we noticed that the only people that were signing up were, like, VCs. Yeah.

Noah Berkson: And you're in San Francisco at the time, which is not. You were in LA at that time. Okay, I was gonna say San Francisco is not a very club-heavy place to be in.

Lucy Guo: Like, I've never, like, I never really been to a club. And then I moved to LA, and I saw, like, how the, like, promoter scene was moving, etc., and I was like, oh, like, I could totally make money off of this. Very, like, I didn't realize how small of a market, like, hospitality was really. But I think it's, like, a decent lifestyle business. Like, you see what's a table service called? There's a table service app. I forget what it's called, but I.

Noah Berkson: Think I know, I know what you're talking about.

Lucy Guo: It's a bottle service app. Like, it does okay. Like, it's, like, very much so lifestyle business, but, like, it's a pretty good lifestyle business.

Noah Berkson: And, and you call your parents, and you're like, I'm quitting my job. And they say, what are you gonna go do? And you're like, I'm starting an app. And they're like, what kind of app? It's, like, to help people get into.

Jess Mah: Nightclubs, Asian parents' dream come true.

Lucy Guo: So they got very, very mad when I quit Snap. I was like, hey, I'm gonna go to Y Combinator. And then they were just like, hey, don't you realize that, like, 99.9% of startups fail? Like, you're going to fail, you're gonna ruin your life. And they're like, if you raise $5 million, maybe I would understand why you were leaving Snap. But the, like, risk-benefit analysis doesn't make sense here. And then, you know, after the Series A, and we raised basically 5 million, they're like, wow, we're so proud of you.

Jess Mah: Oh my God. Yeah.

Noah Berkson: Wait, and then where does that happen? Because, okay, so you start this business that doesn't, and you raise 5 million for that business.

Lucy Guo: Oh no, we did not. Then we pivot into this business called Ava, which is, like, we're going to help you find the best healthcare professionals for, like, the service that you need. The reason why this is just never going to work is because it's, like, a one-off use case, especially for young people, and old people aren't going to be using the app, right? So, like, we very quickly realized this. But this is where we raised, we got into YC with, and then raised, like, a small pre-seed round. Granted, they wanted, like, a million dollars. They wanted to give us a million dollars. We said no. So ended up doing a small pre-seed round and then going to YC. And in YC, I remember we asked our YC partners, how many appointments do we have to book, and how much revenue do we have to generate to be a top YC company? And they told us. And, like, within two weeks, they're like, we're not going to hit these numbers.

Jess Mah: They're just like, who's your YC partner?

Lucy Guo: There's no path there. It was Jared and Aaron.

Noah Berkson: Okay, so you have this. You realize that, hey, the market isn't going to be big enough for this. This, or we're not going to be able to get the user base we need to make that happen. And now you're, okay. Now we got to pivot again. Yeah.

Lucy Guo: So we realized we had to pivot again. And then basically we were calling doctors all the time, and we were like, hey, we wish there was a way to call doctors over the code. Right. And then our roommate was like, oh, so you mean, like, an API for humans? And then we're like, I've built enough viral apps at this point. I knew that would go viral. So we kind of look at them, and they're like. We're like, do you want this idea? And they're like, no, you can have it. So we ended up doing an API for humans. And there's so many stories out there on, like, how the founding. But this is actually the real founding story. So then, you know, did that, launched on Product Hunt. And then a bunch of VCs reached out afterwards because, like, you know, I think VCs were looking at Mechanical Turk and have always thought that there could be a better Mechanical Turk. And Crowdflower had obviously existed, and Crowdflower was a pretty large business at that point in time. So we had a bunch of VCs reach out. But then around, like, the next week, I had built a Pokémon Go map that hit, like, 5 million users in a week. So. So our YC partners actually wanted us to pivot into that, and they're like, hey, Scale isn't going to work out. You should do this Pokémon Go map instead. Look at the traction; you could go into gaming, etc. And then we had told them a little bit later, oh, we actually got a Series A term sheet. And suddenly they were like, oh, yes, go and Scale.

Jess Mah: The advice in YC is very weird like that. I mean, to be fair, though.

Lucy Guo: But I get it. Excel investing increases your chances of success by, like, a good amount.

Jess Mah: Yeah.

Noah Berkson: To back up, just to understand both these. So you want to build this how? Like, what's the. Give us the use case for Ava for. For this Scale initial model.

Lucy Guo: Yeah. So we actually thought we were going to take over BPOs and phone calling specifically because, like, phone calling is such a big thing with BPO companies. And, like, that was a use case that we needed. Right.

Noah Berkson: Outwards for doctors to patients or.

Lucy Guo: Oh, no, just, like, if anyone needed to, like, you know, reach, like, have a human do an outbound call.

Noah Berkson: Okay, got it, got it.

Lucy Guo: Yep. And then eventually just, like, you know, really dove into self-driving cars because that ended up being one of our first customers. And then our lead investor actually was like, you know, you can just use AI, right? Like, you have an API, you have structured data. And we're like, oh, good point. And then we were also just, like, having trouble quality controlling phone calls. We were starting to get, like, API calls where people were, like, having us call to, like, sell bad stocks and scam people, essentially. So we're like, okay, cool, like, we don't want to do this. Like, let's do something that we can quality control. And that ended up being the start of Scale. Yeah.

Noah Berkson: So you have these. Did you. All those investors that invest in this initial idea, did that all roll over? Like, first, like, the people that invested in this nightclub, like, clubbing for ClassPass business that are, like, I invest in this business, and now that has become Scale AI. And that is probably one of the best investments I've ever made in my life.

Lucy Guo: So we've actually only had one investor in our pre-seed. The rest all came after Excel put in my.

Noah Berkson: Okay, wow. And this Pokémon map.

Lucy Guo: Yeah.

Noah Berkson: You were just, you're, like, I'm doing a startup; that's not hard enough. The startup's not really going the way I want, but, like, I also need to go build this Pokémon map.

Lucy Guo: I knew it would only take a weekend. And then another friend and I were like, you know, we saw the trends of Pokémon Go. So this was actually not with Alex, but with my friend Jared. And we were just like, okay, cool, like, let's do this. Like, Pokémon Go map. Let's build it over a weekend. And then it became one of the most popular ones. It was, like, featured on pretty much every single website. It was really cool because, like, you could be, like, he was in a wedding in, like, the middle of nowhere in the United States, like, Middle America. He's like, dude, I see people on their phones looking at a Pokémon Go map. Which is a cool feeling to have. Actually, part of the reason we probably didn't pivot into that is also because we couldn't figure out the equity splits between everyone because we were two founders. Now we're three founders if we do the Pokémon Go map, etc.

Noah Berkson: That's hard. What'd you do with that? What'd you do with that?

Lucy Guo: Oh, we did nothing. It just came and it died. Because then we got the Series A for Scale, and then decided to focus on that.

Noah Berkson: Okay. And the self-driving, like, Cruise becomes kind of your first eye-opening to, hey, this, like, data labeling is a big business, and we can, we can completely pivot our business towards this.

Lucy Guo: Yep.

Noah Berkson: But there's also, there's, like, what, two or three companies, autonomous vehicle companies at that point. So, like, you need to get all of them as customers first, or are you, like, hey, we can take this, and now we'll go into other industries.

Lucy Guo: Yeah. So we, you know, we basically tackled one by one. But I would say, like, what really helped our trajectory was LIDAR labeling. And we had hired this incredible engineer who was able to build our LIDAR labeling tool in three days. And this LIDAR labeling tool is better than the LIDAR labeling tools that, like, pretty much every self-driving car company was using on their own. So they're like, oh, great, you'll label data more accurately, and you have this better LIDAR labeling tool. Like, yes, please. So that was really when we were, like, winning customers without, like, it was, like, a one-call sale.

Jess Mah: How did Cruise come in as the first one?

Lucy Guo: We just mass-emailed everyone that was, you know, YC founder.

Jess Mah: Okay. Yeah. That's kind of the YC way. They tell us to just sell it to each other, and it's, it's great. It's the mafia, you know.

Lucy Guo: Yeah.

Jess Mah: I mean, that's how I got all my first customers.

Lucy Guo: I know. I think that, like, if I were to do a B2B SaaS business, like, I want to go to YC. Right.

Jess Mah: Because you just get that network; it's, like, instant credibility. Like, I put Airbnb, I put Stripe, Pinterest as my, like, marquee customers. Put the logos on your website; it sells everyone else. It's a really unfair advantage.

Noah Berkson: Who was your first customer?

Jess Mah: My first was actually Bill Clerico from WePay.

Noah Berkson: Okay.

Jess Mah: Yeah. But I mean, pretty much everyone you could think of, I got to sign up, all thanks to YC.

Noah Berkson: So. Okay, so now you. At what point do you start to see this business is going to take off? Like, where was that point in the business where you're, like, inflection point was.

Lucy Guo: Really when we went into self-driving, and then we hired this guy Shrav, and he was just, like, an incredible marketer and seller. So we were just starting to close deals, like, left and right. And we very quickly grew as a brand that had the highest quality data.

Noah Berkson: And, like, what's the trajectory of that business? Like that. Like, that first year, second year, third year. Like, how long did it take to get to, like, a meaningful revenue point?

Lucy Guo: I mean, I would say year two, it was pretty meaningful, but, like, year three, four is when it was, you know, like, really blowing up.

Noah Berkson: What. What is that like? I mean, so you get to this point where I assume you're just getting flooded with interest from investors. Everything's really exciting. Like, very few people get that experience, right, to be in that place. Like, what was that like?

Lucy Guo: I mean, this sounds kind of crazy, but I feel like I've always been very lucky to, like, be in that place. Like, my whole thing is I won't do a round unless it's, like, preempted. Right. So it's exciting, but it's also, like, okay, cool.

Noah Berkson: But it wasn't, like, that wasn't a huge motivator at the time. Like, wow, we're just getting so much interest. People are putting really high values on the company. That wasn't a big driver for you?

Lucy Guo: I don't think so, no.

Jess Mah: Yeah. Well, I'm curious, since you've kind of ridden that high for the past few years, what is your motivation now? My read on you is that you're just. Just kind of, like, a curious geek. You like to play with things; you're a tinkerer; you like to explore. But I don't know. How else would you describe your motivations beyond that?

Lucy Guo: Yeah, I mean, I think that I really want to build a second unicorn. Because when you look at the best founders in the world, like, I think building your first, like, a lot of it is luck. But the best founders, they do have a skill, right? Like, some people build, like, three unicorns, which is just, like. It's a little insane. But it would be cool to be able to, like, figure out how to repeat it. And I also think consumer is one of the hardest challenges out there. So it's something that I'm personally really interested in. And I get to work with my friends, and I become friends with a lot of creators that we're working with right now. So it's just fun.

Jess Mah: How many years did you take off between Scale and what you're doing now? And then we'll talk about what you're doing now.

Lucy Guo: I don't really think I took off that much time because I immediately went into venture after. So I started Backend Capital and HF0 with Dave, and HF0 is still running. It's a program in San Francisco that backs second-time founders, essentially. That wasn't the original thesis. The original thesis was, like, we're just gonna back the best engineers. But, like, I think second-time founders generally, like, you learn more from what you did right than what you do wrong. Although you do learn from what you do wrong, right. So I think that there's just, like, a higher hit rate with second-time founders. Data might show otherwise. I actually don't know because, like, I.

Jess Mah: Don't know; the data does show that it is better.

Lucy Guo: Yeah, I've seen totally different. Like, I've seen so many studies where, like, some data shows it's not, some data shows it is. So yeah.

Noah Berkson: Have you always liked, is investing energizing for you?

Lucy Guo: I would say investing is definitely fun. It's definitely easier. I like that I got to do a lot of breadth versus depth. So learn about different industries. And I think it's very similar to founding a company in the sense that you need to pick the best people. So as an investor, I really look for who's smarter than me and who's a better engineer than me. And those are people that I want to back, especially when I'm going so early-stage. And I do the same with my own company. I think the hardest roles for me to interview for are the non-technical roles because I just really don't know what a good finance person looks like. For example, I have other people interview my finance people.

Noah Berkson: Was that transition when you decided you were going to leave Scale? Was that transition hard? I'd imagine I'm thinking about this. My identity is always so tied to businesses in those moments when you end up saying, hey, I'm going to leave; it's like I feel like I'm kind of leaving my identity behind. And a lot of times then I think, like, I need to do something immediately to, like, build a new identity because otherwise it's, like, there's a gap. Like, I don't. I'm, like, a chicken with its head cut off. Kind of, like, I don't really have one. Was there, like, what was that? What was that process like?

Lucy Guo: Yeah, I would say for, like, the months leading up, I was already talking to Jared, and we were like, okay, cool, like, we're gonna build a company together. So quite literally the next day, like, we were building a company together, and then there were just a lot of disagreements, which is why, like, the months leading up, I was already in talks with Jared. It ended up just, like, I realized I was, like, kind of burnt out. So I got him his job back at Stripe, and he's now crushing it with his company. And I invested, obviously, because I believe in him. And yeah, took a little bit of a break, then went into venture.

Noah Berkson: And you had a little bit of fun between.

Lucy Guo: Yes, I went traveling for, I want to say, a few months.

Noah Berkson: For a few months. We want to hear about that. I was saying, I think when I talked to you the other day, I was like, from the outside, what I would see, like, you first came on my radar, probably, like, with Scale. But then afterwards where I was like, there's, like, a news article, there's something always coming up about you, and you were, like, very openly, like, very openly, like, buying really, like, buying a cool place or, like, doing really lavish stuff. Like, but you would, you told me that you're like, hey, I think there's a big misconception about me and that, like, I'm not really that person.

Lucy Guo: Yes. I would say, like, right after, I was extremely frugal. So what I had done was I moved to Vegas, and I bought this apartment for $70,000, and it was, like, you know, a few Thiel fellows, and then a bunch of other people; we were, like, well, let's make a community in Vegas in these, like, kind of janky 70K apartments. And we were, like, travel hacking. So what we would do is, like, you know, we would eat at the airport lounge, for example. So it was, like, a five-minute drive, like, very quick skateboard ride to the airport, and we would buy, like, a cancelable flight, like, a Southwest flight, get in security, cancel it, and eat at the AMEX lounge for free. We also did a lot of travel hacking that allowed us to fly for free, first class internationally, amongst other things. And I'm not going to say how we did that.

Jess Mah: So you're doing this after Scale. You've already made a fortune, and yet you're still flying for free through travel hacking on Southwest.

Lucy Guo: Well, I would say I've had a fortune. Like, I did a small, like, secondary of the Series B. But, like, for me, it's more important to grow my money versus, you know, live off of it. Yeah, because it was, like, a seven-figure secondary. So I was like, okay, cool, like.

Jess Mah: Let me decide how much secondary to do. What's the cause? I always think about this as a founder. I meet so many people who built their businesses for so long, and they have eight-figure, nine-figure opportunities to take money off the table, and they choose not to. And I really respect those people, actually.

Lucy Guo: Yeah, I took way too much off the table.

Jess Mah: You took way too much.

Lucy Guo: I mean, for the valuation at the time, I do think I took too much. Nowadays, the way I think about it is just, like, is it going to change my life? Am I going to, like, you know, do something drastically different? If the answer is no, I don't really.

Jess Mah: So you decided before that, even with the secondary, you would barely touch it; you would let it grow.

Lucy Guo: Yes.

Jess Mah: And you would keep your lifestyle the same. Why. Why not spend it more lavishly? Because that's what the newspapers like to think, apparently.

Lucy Guo: This.

Noah Berkson: Yeah. Is this. Is this a mis. Like, is this a misconception?

Lucy Guo: I mean, I would say after I was able to, like, grow that money a bit, I definitely was like, okay, cool, I can buy stuff, right? But I think I'm, like. Like, after I bought everything that I, like, really wanted. And the whole mindset was actually, like, a total experimentation. It was, like, almost a social experiment for me because I started noticing, like, I had hung out with, like, very, I think, humble people for most of my life. And then during COVID, I met this one friend who was just, like, you know, driving Aston Martins every single day, like, different car every single day, was just, like, spending massive amounts of money on clothes, watches, etc. And, like, in my head, I was like, this is the most stupid thing ever, right? But I noticed how people treated him differently.

Jess Mah: In a bad way.

Lucy Guo: Oh, no, in a good way. People are so nice to him. Like, random strangers so nice to him. And this is, like. And I understood, like, this was, like, how LA kind of worked. Like, I have, like, you know, gone in front of a club, and they let, like, 10 girls in, and they stop me, and they're like, you can't go in because you're, like, dressed like that. And I'm like, come on, bro. This is, like, you know, when I first moved from San Francisco, I've learned how I need to dress in LA, but I noticed just, like, how nice everyone was being from, like, you know.

Jess Mah: But also, people are trying to be friends because they think that it's not.

Lucy Guo: Even just, like, friends. It's, like, you know, like, maybe they think he's gonna tip well, right? But then, like, you know, the waiters bring him, like, extra food or, like, pay extra attention to him. I was like, that's all you need to do for people to just, like, literally bend over for you. Wear nice clothes. So I went on a little shopping spree, and I was like, let me get some jewelry and some nice clothes, and let's see what happens.

Jess Mah: You have an amazing Pikachu backpack, I noticed.

Lucy Guo: Oh, yeah.

Jess Mah: Which I really, really like.

Lucy Guo: No, it's funny because, like, now everything I wear is so cheap. Like, this is, like, you know, from Zara. My pants are from Shein, and, like, I love Shein. I know. I love Shein.

Jess Mah: So cheap.

Lucy Guo: It's the best. All my pants are from Shein now. Yeah. And I don't wear any of my jewelry anymore. Like, it's all in my safe.

Jess Mah: So you kind of went through the stuff.

Lucy Guo: I went through that thing, and then.

Jess Mah: You came out of it.

Lucy Guo: But I think I, like, I'm lucky to be able to do that now. I think that I noticed how much nicer people were being to me. I was getting invited to everywhere, etc., because people want to be friends with the rich person. But now that everyone knows who I am, or I've made that network, I'm so over it. So now I just wear Shein again.

Noah Berkson: What were the most outrageous things you bought? If you could think of two or three things, you're like, that was outrageous.

Lucy Guo: I mean, I think watches are, in general, good investments. Like, I bought a very expensive watch.

Jess Mah: But, like, Noah's a big watch guy.

Lucy Guo: Yeah. I think if I, like, resold it on Sotheby's, I could get, like, 10x what I paid for it. Wow.

Jess Mah: So, like, wow, that's awesome. It's, like, better than crypto investing.

Lucy Guo: Yeah.

Noah Berkson: I'm like.

Lucy Guo: It was, like, ridiculous, but, like, was it ridiculous? I don't know. That's awesome. Then it would probably be my cat.

Noah Berkson: How much did you spend on a cat?

Lucy Guo: 20K.

Noah Berkson: You spent $20,000 on a cat? What type of cat is this?

Lucy Guo: F1 Savannah.

Jess Mah: That's awesome.

Noah Berkson: Okay, I need to see a photo of this after this. Yeah. Can you get 10 times as much for the cat, too, if you sell it?

Jess Mah: All right. Bad ROI.

Lucy Guo: Bad ROI. Declining. And then what is something else dumb that I've spent on? I don't really know. It'd have to just probably be, like, a random jacket or something that I bought that I thought looked cool, and I saw a price tag.

Jess Mah: You're pretty frugal then.

Noah Berkson: Actually, it sounds like you bought what looks like a really sick place in Miami.

Lucy Guo: Yes. I'm finally renting it out, though. I think the tenants started yesterday, so. Thank God.

Noah Berkson: It's interesting. I was just actually reading about this other guy, Neil Patel, who's, like, this. He's, like, a marketer. He actually lives in LA, I think.

Jess Mah: Oh, yeah, I know Neil.

Noah Berkson: But he was talking about. He did this experiment where he was, like, he owns, like, a marketing agency, and he's been very successful doing it. But he's, like, I wanted to see, would people basically, could I charge more money if I dressed nicer with clients? Like, if I basically, like, projected that I was really successful, would people then, like, could I make more money doing it? He's, like, so I went and just bought, like, all the, like, Louis Vuitton shoes and the, like, Dior, all this shit. And he's, like, I actually was. It was, like, way more, like. He's, like, people just thought I was so much more successful. So, like, more clients would sign with me; they'd spend more money with me, which was really interesting.

Lucy Guo: Oh, totally true. Yeah. I mean, like, this is what they do in Miami. They, like, you know, rent an Airbnb for a day. Like, rent a car and talk about, like, how you should buy their course so they make tons of money, which is crazy.

Jess Mah: But all the time where they just speak, say, oh, this is my Ferrari. This is my Lamborghini. This is my jet. And it's, like, just borrowed for a few hours.

Lucy Guo: Yep. But it does increase their sales like that. This is how, like, Miami be successful, like me.

Jess Mah: And look at what I've got. Even though it's B.S. Yeah.

Noah Berkson: What. What'd you think of Miami? You're not there anymore.

Lucy Guo: I really love Miami, but that's because I got to meet, like, people that were, like, born and raised in Miami. So you. I met, like, all my friends were, like, you know, Latin, Venezuelan, Brazilian, Colombian, etc. Like, true Miami people. And they weren't in the, like, I would say, like, the fakeness of Miami, which was, you know, like, people go there to, like, really show off their wealth through the bottle service, etc. That just wasn't them. Like, you know, they grew up in, like, the middle of Miami. I don't even know the neighborhoods, but, you know, like, not as, like, crazy. They didn't grow up in Miami, Miami, the city. And then they just went to college. University of Miami stayed there. But I think that, like, real, like.

Jess Mah: Authentic friendships, it sounds like.

Lucy Guo: No, it was, like, very much so. Mi casa es su casa. Like, one memory I have of Miami is just, like, I was there for the first time. I had no friends, and I wanted to check out Space. So I just, like, walked in at 6 AM. I'm standing there alone, and then there are these girls who are, like, oh, are you alone? And I was like, oh, yeah. And they're like, oh, well, you're at our table. You're our friend now. Let's be friends.

Jess Mah: So sweet.

Lucy Guo: Yeah, they just adopted me. I became, like, I made friends with a bunch of people there. And then another girl, like, not, like, two hours later, I was like, oh, you're friends with her, then you're friends with me. Mi casa, su casa. Hands me her house keys. It's, like, you can use my house whenever you want. And I'm just like, I don't know you, but thank you. And then I end up using her house. So it was great.

Noah Berkson: That's super unique. What were the other things you really liked about Miami?

Lucy Guo: I would say the food was good, but I would say outside of the food and people, yeah, I think the food and people are the best in Miami.

Noah Berkson: But you leave to start your next.

Jess Mah: Business, and you come back to LA where we are today.

Lucy Guo: Yes, I'm in LA because the creator economy is such a relationship-driven business. And I wanted to be where the creators were, and this way I can see them every single day, invite them to things last minute, etc. Because there is something, I think that emotional retention is very real. There is obviously product retention, but I think that what I've learned about creators is that wining and dining and taking care of them and being their friend is going to pay off more than product retention. Sometimes where they will stick with you, even if they think they can make more somewhere else, or even if another company offers them millions of dollars to move over, if they feel that emotional retention, they're not going to move over.

Jess Mah: But how did you decide that you were going to do a lot of that emotional labor to maintain and create these relationships? Because if you're trying to build a company with massive scale, which you've done before, just hire out a team that does this; they're effectively your sales reps managing accounts.

Lucy Guo: So I do have a team that does it. I would say, like, there's a certain level of creator where they don't want to talk to anyone except the founder. And also, like, I found that, like, I'm just, like, online 24/7. So every single creator has my phone number. And, like, I might have a team, but, like, at, like, 2 AM in the morning, like, my team's probably not responding. I'm more likely to be responding to them. So yeah, I mean, it's cool.

Jess Mah: They probably respect the personal touch. And even if it's just, like, a few things from you here and there, that must go a long way for cementing the partnership?

Lucy Guo: Yep.

Noah Berkson: Is this a big lifestyle change for you? Because, okay, you come from being an engineer, you come from Silicon Valley, then you move to LA, and now, like, your life and business is being with creators, which is, I assume, a lot of nightlife.

Lucy Guo: Not really, no. I would say for the nightlife stuff, I definitely send my team. Like, for example, my friend used to DJ this, like, Thursday night called Bar Lis, and I just refused to go. So I would just, like, kind of force my salespeople to go. I'm like, hey, I know. Like, it'll be fun, though. Like, 10 PM to 2 AM, you'll be in the DJ booth; just, like, become friends with every single creator that you see there, and they're, like, almost more than happy to do so. Oftentimes, I think I try to be there more for the, like, I guess, like, upscale events or, like, the cool things that, like, don't happen very often.

Noah Berkson: What are the wristbands you have on right now?

Lucy Guo: Yeah, so I took our team to the F1. Cool. And these are from the F1.

Jess Mah: Oh, fun. That's awesome.

Noah Berkson: What was your experience at F1?

Lucy Guo: I mean, it was great. You know, they had a caviar bar, so I was just eating mounds and mounds of caviar.

Jess Mah: Caviar?

Lucy Guo: Oh yeah. Like, this is, like, an example where I'm kind of cheap. Like, I will never pay for caviar on my own, but, like, if I get it for free, which I happen to be at a lot of places where I get free caviar, which is an amazing perk of life, I'll eat, like, all of it. Like, at some point, I was, like, just, like, keep on giving me just mounds of caviar on my plate anywhere. It was great.

Jess Mah: Were you into caviar and, like, uni and all this fine stuff before Scale too, or, like, I don't think I.

Lucy Guo: Ever experienced it before because I could never afford it, and I wasn't in, like, these situations where I would get it for free. But I would say, like, my, like, taste in food. I really like savory foods and salty foods. Like, I oversalt my food. So it was, like, pretty much natural that I would like it. Has your.

Jess Mah: Your life and your relationships with your parents and your extended family and your childhood friends changed a lot since making money and being successful? What's that evolution been like? And have you had to drop any relationships because it just doesn't fit anymore?

Lucy Guo: I wouldn't say I had to drop relationships because of, like, being successful. I would say, like, my relationships more so dropped when I dropped out of college because I was, like, at a different place in life than a lot of my peers that I had maybe, like, went to school with, right? So we just didn't have as much in common. Like, I was working and, like, let's say in high school, all we talked about was, like, anime, right? Like, I wasn't watching anime anymore, which isn't great for conversation. Or, like. Like, so many girls, like, all they talk about is, like, boys when they're growing up, right? And that just, like. That talk didn't interest me anymore. So I would say, like, that is something where, like, I kind of diverged from my, like, childhood friend groups. As for my parents, though, I would say we're probably closer, but I wouldn't say it's, like, a function of being successful. I would say it's, like, a function just, like, me maturing and realizing that, like, all the things that they did in the past were because they loved me and that they were really trying to do what was best for me. And I could see, like, why it really hurt them when I, like, dropped out, like, quit my job, etc. But now we're on good terms, so.

Jess Mah: Yeah, that's really beautiful.

Noah Berkson: Do they get to enjoy some of your success? Like, will they. Will they take that and enjoy it?

Lucy Guo: I don't think they like me spending money. Like, I took them on a trip to Switzerland. Like, I went. I took them on a Christmas vacation to Switzerland. The whole family. I spent a lot of money on that Switzerland trip. And they just got so mad at me. They're like, why did you hire a private driver? We could have taken a train. And it was to the point where I started crying. And I didn't talk to them for, like, the last two days of vacation because it made me feel so bad.

Jess Mah: So the immigrant mentality is to stay frugal, and you can't really pull that out of someone.

Lucy Guo: Exactly.

Jess Mah: How about you? You've made a lot of money, Noah. How do you.

Noah Berkson: Well, I'd say it's so funny because I think. Yeah, I think a lot of people, if they are frugal, they just don't enjoy that. Even when you're, like, hey, let me take you to this nice dinner. Hey, fly business class. Hey, these things. And they're just thinking about, well, like, this is really expensive. Or, like, I don't need to order the steak. I could order, like, the chicken. And it's $20. You know, it's $20 cheaper.

Jess Mah: Are your parents bougie?

Noah Berkson: No, not at all. Extremely. Extremely frugal.

Jess Mah: Wow.

Noah Berkson: I was thinking I had a similar experience in college. I dropped out of college, and I started a business, and I lost pretty much all my college friends because pretty quickly it's, like, the things that were important pre-that just weren't important anymore. And it was pretty hard to relate to people because they can't really relate to you. Or they're, like, come out tonight, and, like, dude, I can't. Like, I gotta. Like, I have to work, and I have to make. Like, I have to make payroll, right? Or it's, like, all these things start to change where it's just, like, hard to relate to friends. Yeah, I definitely had that. Did you end up making a lot of older friends then to kind of, like, compensate for that?

Lucy Guo: No, I would say my friends were mainly the people that I met in the dropout community in San Francisco. There are quite a lot of us. You know, there are a lot of Thiel Fellows, for example, and I just noticed that, like, some slightly older friends, like, you know, 25, let's say, back when I was, I don't know, 18, 19 years old, everyone wants to, like, help and mentor the, like, young kid that might be a prodigy, right? And I don't think any of us are really prodigies, except maybe Vitalik. I would call Vitalik a prodigy. But people viewed, like, just being part of the Thiel Fellowship as, like, something that makes you a prodigy, even though I would say it's just more so people that are smart, that were, like, more risk-oriented.

Jess Mah: Should we talk about dating?

Lucy Guo: Sure, we can talk about dating.

Jess Mah: What is it like to date as you now?

Lucy Guo: It's very interesting. I think that I've had the benefit of, like, being in, like, I have a large network, right? So, like, I have a lot of people to choose from, which is really nice. For example, like, for the longest time, I pretty much only had, like, trust fund babies hitting on me. And I'm like, okay, cool. Well, like, you have liquid money, so you can pay for everything, which was great. But then also you get, like, the other side where, like, you know, I don't really know how to say this that nicely, but, like, a lot of people are gold diggers or, like, escorts in LA, and, like, you know, I'm bi, so, like, I have a lot of these, like, escorts leech onto me in LA, and I'm like, oh, well.

Jess Mah: How do you meet the escorts? What's the mechanism?

Lucy Guo: Oh, well, you don't really know they're escorts until someone tells you.

Jess Mah: Wait, you're just picking them up organically, or is it through an app or.

Lucy Guo: You know, there's no app or escort. Well, I mean, just off Hinge, you're.

Jess Mah: Like swiping, and then it's, like, an.

Lucy Guo: I would say it's organically, like, in.

Jess Mah: Person organically or whatever.

Lucy Guo: Yeah. I will say there are a lot of escorts on Raya.

Jess Mah: Uh-huh.

Noah Berkson: How do you spot this out now? Like, how do you know intuitively, like, pretty quickly or instinctively, like, this is probably an escort?

Lucy Guo: Oh man, that is so controversial.

Jess Mah: Or, like, give us the controversial.

Noah Berkson: We love controversial.

Lucy Guo: Again, I want to preface this by saying that, like, I am all for people getting their bag. I just, like, you know, I think it's, like, a form of cheating if I'm with someone; I don't know what they're doing. So prefacing it with, like, go get your bag, right, girls? But as for how you can tell, I would say they're, like, always on jets. They're going to, like, very luxurious vacations with, like, nobody in the background. They definitely own a lot of expensive stuff. Like, they're on. They have Hermès bags, they have Chanel, etc., and they just don't have a job. You can't Google their last name.

Jess Mah: Wow, you've got a system down.

Noah Berkson: Okay, and so, so dating in LA, what are some really bad experiences that you've had?

Lucy Guo: Probably the escorts.

Noah Berkson: Probably the escorts. Okay. Okay. Do you have any stories from that? Like, anything that you can recount?

Lucy Guo: They're all really nice people. Like, they're really genuinely nice people. They're actually a lot smarter than you would think. Like, I think that part of it is that they probably studied psychology; they're very intellectual, etc. And they can keep a conversation going for hours, which is how they reel you in. I think it's just, like, you know, it hurts in the end when you realize, like, oh, you've been, like, hooking up with all these people without telling me behind my back, like, what?

Noah Berkson: So they don't ask you for, like, money or for anything. They just start doing that with other people. So they, like, come to you, like, hey, this is just a normal relationship. And then you find out that they're.

Lucy Guo: Yeah.

Noah Berkson: Wow.

Jess Mah: Oh, fascinating. And are you looking for, like, a long-term serious thing?

Lucy Guo: I mean, I would like to get married and have kids. Yeah, yeah. Like, I actually was, like, maybe I should start dating men again. Which I did, you know, open up my dating apps back to men. Because I was like, man, like, it's so much easier. Like, you don't have to worry about that problem. They pay for everything. I love people paying for me now.

Jess Mah: But would you want to only be with a guy who could pay for everything, or do you believe in equal? How do you deal with the polarity issue?

Lucy Guo: Yeah, I fully believe in a guy paying for everything. Like, I'm a woman. I like being taken care of. I think the biggest turnoff that I can have is if, like, a guy asks to split the bill. Sometimes I'll just take the check because I'm nice. Right. Like, if I ask someone out, I'm always gonna be taking the check. Or if, like, I feel like the guy's got enough turns, then, like, you know, I'll take the check. But no, I believe in chivalry. Like, I'm actually, like, a lot more, like, princess girlier than most people would think in that sense.

Noah Berkson: How does that translate when you're dating women?

Lucy Guo: Oh, I pay for everything, but I think that, like, I expect them to do nice things, like, cook for me, for example. Like, I'm pretty much, like, a guy in that sense where it's, like, okay, cool, like, and, like, just don't make me feel used. Like, if I'm picking up, like, you know, the dinner and, like, a bunch of things, like, pick up, like, one drink.

Jess Mah: Yeah, yeah.

Noah Berkson: Would you. Would you marry a woman long-term, or, like, do you. You want to. You want to marry a guy? How are you thinking about that?

Lucy Guo: I don't really think about it. Like, I would marry a guy or girl.

Noah Berkson: Okay.

Jess Mah: It's just about the person. If it's the right fit.

Lucy Guo: Yeah.

Noah Berkson: What are you looking for?

Lucy Guo: I mean, I would say, like, one thing that I've always valued that I don't know if I should value is, like, being a power couple. I like really intellectual, successful, like, ambitious people. But also I realize that that's, like, not the most important traits in the world sometimes. Like, obviously, like, you know, high EQ, being loyal, being kind are important as well. I think my standards might be a little bit too high, but, like, that's a whole other thing. But I would say, like, there are, like, deal-breaker traits and traits that are just, like, you know, I could live without.

Jess Mah: Do you think you emasculate the men, given how successful you are? Because I get asked that all the time too, and it makes it a bit challenging.

Lucy Guo: Yeah. I would say, typically, the men that I have dated are more successful or, like, come from very old money, so they don't feel that emasculated.

Jess Mah: But then, isn't that limiting? Shouldn't you be open to dating guys who are, like, less successful or not from old money? And then you might have some of this, but you might not also?

Lucy Guo: Yeah, I think my philosophy is I want to be able to do things without having to pay for the guy. How do I explain this? Like, if we are going on a trip to Europe, and I don't want to fly economy because I value sleep at least, you know, like, when I'm, like, traveling, I want to, like, be on an adventure, like, right when I land. And I really don't like back pain. I want the guy to be also, like, I'll pay for my own business class flight. It'd be nice if he could pay for his. Like, I don't want to pay for his.

Jess Mah: Yeah, but he'll pay for his own.

Lucy Guo: Yeah.

Jess Mah: So it's, like, you have the super-rich guys, and then in the middle where they'll cover themselves, so they'll still take you out, but they're not going to cover all your luxuries. Like, you'd be okay with that?

Lucy Guo: I'd be okay with that, yes.

Jess Mah: All right, perfect. So let's send Lucy a DM if you or anyone you know qualifies.

Noah Berkson: There's a Kelleher.

Jess Mah: Kelleher. Yeah, Kelleher. I have so many friends who met their now-wives on Kelleher.

Noah Berkson: There's Kelleher. There's this dating. It's, like, a luxury high-end dating service where I think it's, like, 50 grand.

Jess Mah: I thought about joining Kelleher, but they quoted me 125 grand.

Noah Berkson: Because you're picky. Because I think they do it based on how picky you're gonna be about.

Jess Mah: The people you're gonna meet.

Lucy Guo: That's actually really interesting because most high-end dating apps I see, it's, like, the girls are free, and the guys have to pay massive amounts of money.

Noah Berkson: But this also isn't, like, an app; it's just a service. So what you'll be is you'll be, like, here's the, here's the type of person I wanna meet, right? And, like, am I open to. Is it just California, or is it just LA? Is it. I'm open anywhere.

Lucy Guo: But the services are the same where it's, like, the girls, unless they know the girl has money, then they don't ask the girl for money. But, like, for the most, I, like, I pretend I'm a different name, for example. And then. And they will literally just add you for free.

Jess Mah: But then you're passive in the network. You're not active.

Lucy Guo: You're passive.

Jess Mah: And I want to introduce you to my friend Courtney. My friend Courtney is helping powerful, strong, successful, and rich women figure out what exactly do they want, how do they get clear on that, and how do they show up in a way that attracts the guy they want. So I'm going to put you in touch with her and anyone else you need some, some help here, let me know. Especially if you're a powerful woman. I thank Courtney for helping me figure out all my own stuff, and she would make me write this, like, guide for what does it feel like to be with the perfect person? And over three months, we tweaked it, like, on, at least a weekly basis.

Noah Berkson: You realize that, like, what you want in that moment might not actually be exactly what you want, and you start to, exactly. Yeah, yeah. This, this Kelleher one. Because also it weeds out a lot of the people, right? So it's, like, it's all successful women who would also be able to, like, pay 50 grand or 100 grand or whatever to go do a service, which also means you're very serious. But you're not getting, like, I don't generally like X, or, like, you're not getting, like, model, actress, that type of thing. You're getting, like, VP at Salesforce or, like, you know, at Meta or.

Lucy Guo: See, like, my problem is, like, I really like creative people. So, like, the people that I would date are, like, you know, musicians, actors, actresses, like, DJs, etc., which also limits the pool even more because the number of successful people that, you know, are in those fields, like, the percentage chance of making it is just very small.

Jess Mah: Yeah.

Noah Berkson: Have you dated any of those people? Oh yeah, lots of them.

Lucy Guo: Yeah.

Noah Berkson: Okay, tell us about Passes. Maybe to backtrack a little bit. You started after you took a little bit of time off, and then you start Passes. Why is that something that you. Why is that an area you want to start a business in? Why is that an area you even really know much about?

Lucy Guo: Yeah, so I actually started Passes while I was running HF0 and Backend Capital. So we were essentially trying to, like, incubate, like, be the best accelerator for companies and alternative to YC. And during that period of time over COVID, I just made a ton of creator friends, and I saw that there was a real problem in the creator economy when it came to good monetization. Around the same time, Patreon raised at a 4-billion-dollar valuation, and I really respected the brand, but I thought that I could probably move at a faster pace in terms of product velocity. So I floated the idea to a bunch of LPs because none of my founders in the batch would work on it. And then they're like, yes, go start a company. And quite literally within 48 hours, every text message I had around raised didn't have a name, didn't have a deck. I literally was, like, hey, I'm building another company. Don't really know what it's going to be, but it's going to be, like, you know, adjacent to Patreon. And it was just, it was a really quick fundraise, so ended up just starting it. And the idea is that, like, we want to be the best place for creators to monetize their brand and, like, become entrepreneurs. Because I think creators are businesses, and I see them, like, as small businesses today. But, like, you can really grow them into, like, these unicorn companies. And we see this with, like, you know, Jake Paul's companies, like, Better, for example, now he has W. Logan Paul with Prime, like, Kylie with her cosmetic brand, like, every influencer with their liquor brand, etc. But, like, they are essentially their own marketing machine. They don't need any CAC, really. So. And, like, with Passes, we even see, like, how much fans are willing to spend on their creators. Just because you say, like, go spend money on this. And it translates pretty well when you find, like, a product, for example, that you think your fans will align with.

Noah Berkson: How did you differentiate, like, when you were thinking about that initially? Because there's probably a couple different categories of this. There's, like, adult, right? Which would be, like, the, like, OnlyFans side of creative. And then there was, like, the Patreon side. Did you say, hey, I want to just play, like, right in the middle, or, like, is that. Yeah. How were you thinking about that?

Lucy Guo: So I mean, like, we're actually a lot stricter than Patreon. Patreon allows nudity, for example. We don't have any of that. So a lot of, like, nude content that is on Patreon. They just, like, have to go to Patreon instead of us if they don't want the, like, adult brand. I would say that the vision has always been to build fintech tools. And in order to build fintech tools, you can't, like, be an adult platform. Right. So, like, that was already just cut off from the beginning.

Noah Berkson: That's a very challenging space to be in. Do you then, like, did you kind of see, you saw this as, like, a conduit to, like, embedded finance. And that was, like, the whole idea for this business.

Lucy Guo: Yeah, I mean, I had initially wanted to build a company that, like, basically got creators these, like, better brand deals that included equity, for example. But then I realized that creators just aren't gonna trust their manager. And their managers are very, like, cash-incentivized because Hollywood loves upfront cash. If you weren't the one making them the most money possible. And I saw how much money was possible to be made from, like, direct fan-to-creator interactions, especially during COVID when, like, you know, everyone was really lonely. Right. And they were craving a deeper connection. So I think step one was, like, okay, cool, like, let's make more money for creators than really anywhere else they're making. So they gain your trust. And once you have the creators' trust, they're going to listen to you over their, like, agents and managers, and we're going to be more, like, incentive-aligned as well. So now creators make, like, 80 to 100% of their income on Passes. And, like, even our larger creators, you know, the ones with, like, tens of millions of followers, we're still the majority of their income, which is pretty cool to see. But because of that, I think that we have a lot more opportunities in, like, the fintech space that other platforms don't have.

Noah Berkson: That's, that's very cool. How does that, how does that with agents and managers, like, are they a little bit hesitant to let, like, their talent on because they're, like, now this person's going to become dependent on, like, this company. They're going to see how valuable, like, they can make all their money here. And so, like, where am I going to add value? Or is it not necessarily, like, that?

Lucy Guo: I would say that it's not, like, that because for a lot of agents and creators to this day, it still works that, like, they get 20% of whatever a creator does, at least, no.

Jess Mah: Matter what, are, like, locked in for yourself.

Lucy Guo: So we actually see a lot of our creators, you know, they'll, like, literally go into their console andchange changed an amount they're making. So when they give it to their managers, they're taking a smaller cut of the 20%. Like we've seen people change their like earnings from 50,000 to 5,000 one day, like you know, in their console so they can lie about how much they owe their managers, which are wild. Nowadays these contracts are starting to change where it's like no longer that exclusive. It's like you only get 20% of like what you bring to me, but like so many creators are locked into these, like, pretty predatory contracts from the past. And I've seen a lot of my friends currently, you know, like, they have lawyers and they're going out after their managers now. It's pretty crazy as an industry.

Noah Berkson: Yeah, I'd assume that happens a lot, especially with Nil and younger people. Like, what. What have you seen there? Because it seems like a lot of those people are on passes.

Lucy Guo: I would say with Nil, it's actually been a lot more generous because every agent wants to, like, take over Nil, for example. So because of that, they're like, just doing representation essentially for free for a lot of people because it's such a new thing that they want to, like, prove their value first.

Noah Berkson: What are you seeing, like, the highest paid person, like, Nil person that you have on passes? How much money are they making?

Lucy Guo: Like, six figures a month.

Jess Mah: Wow.

Lucy Guo: Yeah.

Jess Mah: That's amazing.

Noah Berkson: Does a lot of that also come from. Is there, like, messaging on the back end? Is that where the majority of the revenue comes from?

Lucy Guo: It depends on each creator. So, for example, some creators are going to make more off of, like, merchandise than they are off of subscription. I would say as platform as a whole, the majority of income is made off of dms, but it is per creator.

Noah Berkson: Is this a business you need to keep raising money for, or is this something that you think can just be like, a cash printing machine?

Lucy Guo: I think it'd be a cash printing machine. I would say, like, the argument for me to make raise money, for example, is like, if I decide, like, okay, cool, like, Nil is really working and I want to, like, have a faster way of buying out every university. Or I'm like, okay, cool, I want to go into pro leagues. Like, that's more expensive. But yeah, like, we've seen similar businesses, I think, that just print cash.

Noah Berkson: Yeah, that's super exciting.

Jess Mah: I love cash printing businesses.

Lucy Guo: Yeah, like, we were cash flow positive earlier this year, and now we're like, we have like over a decade of Runway left. So it's nice.

Jess Mah: That's great.

Noah Berkson: What really, like, what gives you energy?

Lucy Guo: What gives you energy? I think Barry's gives me energy, for sure. I think that, like, as like a very objective answer. Like, I wake up every single day, I do Barry's boot camp, and like, the exercise and just like, the music alone gives me a lot of energy. Other than that, I would say it's just like, you know, solving problems. I think that, like, this company is giving me a lot of energies because it's definitely like a Roller coaster. There's lots of ups and downs. Like, you know, there's highs when like, you know, we get a like very large creator and they launch and it's going fantastic and there's lows if like a creator like leaves the platform for whatever reason. Luckily we have almost 100% retention on like creators that make 5k a month or more. But sometimes a competitor just comes in and you're just like, we're going to triple what you make, which we never really fight back on because it would be stupid to lose money on a creator where we know exactly how much they're making and they pretty much always come back. We actually just got one that purposefully didn't fulfill her contract with a competitor, like stopped sending any posts because she was like, she hated them so much she wanted to break the contract and come back to us. And we flagged the competitors name. So I get to see all the messages that come in that she's sending and I'm like, wow, you really love us.

Noah Berkson: And now I know we talked about this earlier, but your motivation. So your motivation isn't money, your motivation is solving hard problems.

Lucy Guo: Yeah, I mean, I think I like solving problems specifically for my friends. I've always been the person that encourages someone to drop out of college, start their own company, etc. Now I was doing that over Covid where I had a lot of creator friends. I'm like, oh, you should use user talents and like start a creative agency. For example, you could probably do like podcast editing and filming for people and make like X amount per month. And a lot of my friends ended up like taking my advice and like starting their own companies and businesses because of it. And it's just like very fulfilling to see and I think I just want to scale that. To start, I say like life and goal is like, I definitely want to like make my mark doing something like very good for the world. I think in my head like I've always been like fascinated by like human trafficking because like yes, drug is like the number one crime. But like human trafficking is something that like isn't anyone's choice, right? Like they are quite literally being kidnapped, then trafficked, which is like, I think one of the most disgusting crimes on earth. So it's like, okay, cool, like how can I support this cause and try to combat it? And the answer is either I think start my own human trafficking org with like a tech focus on it, or just do what I do best, which is like make a lot of money and donate.

Jess Mah: Yeah, let's put in touch with our friend we talked earlier today.

Noah Berkson: Just talk to somebody that has a. Has a nonprofit doing that right before we came to see you could be. Could be the right person. Yeah. Are you doing something philanthropy right now?

Lucy Guo: I mean, like, I do donate to charities, but I would say, like, I'm definitely just fully focused on passes. We're trying to figure out, like, how we can do philanthropy within passes. So, like, those are other interesting, like, product features that we're looking into.

Jess Mah: Can I ask, what's your attitude on your work life integration? Because going through Y Combinator, the attitude is you're going to sleep under your desk and work 100 hours a week and, like, you're going to die before this business goes out of business. How do you think about it now?

Lucy Guo: I would think about it pretty similarly. Like, I thought about it. Like, I don't think I've ever, like, fully taken a day off. Like, have I, like, been at a festival? Yes. But, like, do I have my phone and my laptop on me at the festival? Yes. So in that sense, I would say, like, always working. In terms of just like, hours in the office, I would say I probably get into the office at around 9 and leave. Leave at around maybe 9.

Jess Mah: So you left early to hang out with us?

Lucy Guo: Yeah, no, I actually got called out. People were like, oh, Lucy, you're sneaking out of the office early today. And I'm like, I'm filming a podcast, guys.

Jess Mah: Thank you for being with us.

Lucy Guo: Of course, of course. But yeah, like, I think that, like, in general, like, for me, like weekdays, I like working until, let's say, midnight and then I go to sleep.

Jess Mah: You really don't sleep a lot. Then if you're waking up at like 5:30am to go to bed and you're going to sleep at midnight, like, that's a five hour night.

Lucy Guo: Yeah, yeah, I would say, like, probably go to sleep between 11 to 12. I really do shoot for like, a minimum five hours of sleep.

Jess Mah: Do you worry about, like, your health and long term vitality if you're only sleeping five hours a night?

Lucy Guo: I mean, according to the doctor, I'm pretty healthy. That being said, like, I think that the most I've ever slept in my life is seven hours. So, like, for me, five hours isn't like that. Crazy.

Jess Mah: I'm so jealous. I sleep eight hours every night.

Lucy Guo: I wish I could sleep eight hours. I mean, this could partially be my fault. Like, I fall asleep pretty late and then I purposely keep the blinds open so I don't use curtains because I like waking up to the natural sunlight.

Jess Mah: Yeah.

Lucy Guo: Because it doesn't feel like I'm, you know, just like waking up from a dream or something. So that's probably also why I end up sleeping less. Because, you know, by the, like, seven hour mark, the sun's bright.

Noah Berkson: Who is like, one of the most influential people that. That are instrumental in your success? If you look back and you say, I wouldn't be here. I wouldn't be where I am today without that person.

Lucy Guo: Weirdly enough, it's probably my stalker from high school.

Noah Berkson: Tell us more.

Lucy Guo: Oh, man, this one's crazy. This is a story. He also did Y Combinator, so I hope he doesn't see this. Yeah, I mean, now that I think about it, like, looking back, it's actually really, like, kind of fucked up everything that happened. But I was basically on this forum called College Confidential, and I was like, I need help with my college applications. And I had meant to be a chemical engineer because I was just like, you know, I was crushing in AP chemistry. It was my favorite subject, blah, blah, blah. So in my head I was like, okay, I'm good at chemistry, I'm good at math. Let's be a chemical engineer. And this guy looks at my extracurriculars and my application and he's like, you're a fucking idiot. You should go to software engineering. And I quite literally never even considered software engineering to be a degree, so I was like, okay, cool, I guess I'll go to cs. And he's like, yeah, you're meant to do startups, et cetera. And he, like, really, like, got me curious about the startup world. And I don't know how, but, like, after that, I somehow, like, got invited to this hacker house called Rainbow Mansion and then met someone that routed me to Thiel Fellowship. So, like, in that sense, I was probably like, one of the reasons I even got the Thiel Fellowship because I had built that relationship in high school. But yeah, he ended up, you know, following me to college after I ghosted him. I think he was like. Like I was obviously 17 at the time that he was, like, messaging me, in love with me, and I think he was like, what, 2520? So, like, a little bit of a weirdo, but yeah.

Noah Berkson: Okay, well, was this, like, this, like, got to a point and you need to, like, get a restrain. We can cut this, but, like, you need to, like, get a restraining order or something or this is just, like, creepy.

Lucy Guo: I mean, it's great. Like, he probably sent me like two emails since then. Like, since he like found me in my college and I just remember like I was so scared for my life. But all he did was he like dropped his suitcase and made a bang. And it was like 2am to see us building by the way. And he just like slowly walks over to me, like grabs my hand, kisses and leaves and I never see him again, thank God. And then he sent me like two emails since then.

Noah Berkson: Terrifying. Have you ever had a stalker?

Jess Mah: I have not had any stalkers like that.

Lucy Guo: And like, see it wasn't as creepy to me back then, but now, you know, I'm like older. I'm like, oh my God, I was like 17 and this guy had like a full on management job at IBM or something.

Jess Mah: So who do you admire and look up to now? Like, is there anyone who you've studied and said I want to be more like them?

Lucy Guo: I would say in general I look up to like people who have founded multiple companies and have been successful at doing so.

Noah Berkson: Did you feel like there was like some pressure when you started pass like when you started your next company that like, hey, I built this unicorn company now like whatever I do next has to be like of substantial value or something maybe equal to what I built?

Lucy Guo: Yeah, I mean I definitely feel that pressure. But I think that pressure is like good for me as well because I'm like, you know, fully focused on doing it a second time and it's going well, so I have no complaints.

Jess Mah: But what's the balance between intrinsic motivation and extrinsic motivation for you? Like intrinsic being. You're just motivated because you love solving problems, you love helping people versus like the pressure, extrinsic being the pressure of like I have to do this to, you know, check the box of I have multiple successes. I'm not a one or two trick pony, you know what I mean?

Lucy Guo: I mean I would say for me it is very intrinsic that I want a two trick pony because like I could fail. And like I don't think any of my investors would care, for example, because they're just so used to, I mean like obviously they would be upset and disappointed. But like companies fail all the time.

Jess Mah: Right?

Lucy Guo: Venture is a power law effect. I think like it's gonna be more soul crushing for me if it fails. So like for me it's like that's part of my intrinsic motivation.

Jess Mah: Yeah. So you just want to prove to.

Lucy Guo: Yourself that yes, I want to prove to myself.

Jess Mah: But then you crush it. 10 years from now you have another home run, grand slam success and then what, you know, will you just Keep on wanting to do this, or will you be ready to move to the next phase and help with, you know, philanthropy or other stuff? Or you operate your life with no plan. Planning. It's just year by year. Let's just see what happens.

The soft skills Lucy demonstrates—curiosity, persistence, adaptability—are exactly what I discuss in The Human Skills That Make Us Irreplaceable.

Lucy Guo: Honestly, I have very, very little planning. But, like, in my ideal future, I imagine having two kids, which I would imagine I would want to spend more time with. So then I would probably be doing philanthropy. That being said, who knows?

Jess Mah: Yeah.

Lucy Guo: Yeah. I didn't think I'd be starting a second company, to be quite honest.

Jess Mah: Really?

Lucy Guo: Yeah. I thought I was gonna stick in venture, like, stick with venture for, like, the rest of my life.

Noah Berkson: You're an early investor in Ramp?

Lucy Guo: Yes.

Noah Berkson: These are people you just knew, the founders, like, early on, or what's the story there?

Lucy Guo: Yeah. So I was a huge fan of their product Paribus. I had used it a ton. And one of my friends, like a teal fellow, he messaged me, he's like, you have to get in on this round. Like, go meet them. And I was like, oh, my God, I have to get on this round because they're the founders Paribus. So I literally hopped in New York the next day and meet with them and begged them to let me in, and they let me in with a check. And then we were just, I guess, pretty helpful early on with just hiring, referred them into a bunch of good engineers and other roles, including actually the one that blew up scale with his marketing. He had ended up recruiting him to Ramp after, and then he blew Ramp up too. So, yeah, they let us double down on the next round and ended up being a very good investment.

Jess Mah: That's awesome.

Noah Berkson: And tell me about some of the misconceptions with creators. When we talked the other day, I was like, it has to be weird because, like, you're spending a lot of time with people. Like, you're like, hey, I built technology companies. I'm an engineer. And then I'm spending time with people who, like, create content for a living. And they seem to be very polarly opposite things. And I think my. The way that I would look at creators a lot of times is be like, oh, you're like, you're selling photos on the Internet. But I guess the way that you put it, it's. It's not. I'm. I'm really oversimplifying it.

Lucy Guo: Yeah. So I would say creators, at least the really successful ones, are very hard workers. Like, much more hardworking than people would expect. Like, they're up early to do photo shoots. They don't drink, they're like completely sober because they want to look fresh whenever they're doing like their next thing. A lot of them have like a different career, at least ambitions of a different career. Whether that's like building your own brand or company or like, you know, being a pop star, et cetera. And we're seeing some of of the hardest working creators transition into the different career successfully, which is really cool to see. I always tell people what makes a difference between a good creator on passes versus someone that doesn't make a lot of money is just the amount of content they churn out. Content does take time and it takes a lot of creativity. I generally think that creators work harder than people would expect.

Noah Berkson: And you want to help a lot of them also with not only making money, but then keeping that money and growing that money.

Lucy Guo: Exactly.

Noah Berkson: Because a lot of times, times, especially if you're not, I don't know if financial literacy is really the term, but if you haven't had a lot of money before and suddenly you're making a lot of money, you don't really know what to do with that money.

Lucy Guo: Yeah, I think creators in general just like no one really taught them anything. A lot of them don't realize taxes exist. Right. So they end up spending all their money on taxes. They've always had trouble financial planning partially because of the way brands paid them out, where a lot of brand deals will pay out six months late. So you could be expecting money in February, but it doesn't come until much later. And then they just, I don't know what it is. Like, I guess it's cause like the excitement of finally getting your check. But like, usually what happens is they get the check and they immediately spend it. Like we've had creators that were like quite literally homeless and then, you know, started making like a good five figures a month. And then they would call us going like, hey, like, I need my payout today, like right now because I have to pay rent. And I'm like, how can you not pay rent? You just made this much money per month. I was like, can you wait like a day? And they answer me like, no, like I need it right now. And I'm like, that is some pretty bad financial, financial planning. And like we even see in our system, like we offer like three different payout levels. Like you can get it in one day, you can get it instantly, or you can get it in three to five days, but you can technically schedule them daily. So like it is coming every day. If you Schedule it daily. And like, the amount of creators that like, use instant payout and pay that extra 10% is like, it's pretty wild. So that just shows to me alone, I'm like, everyone needs better financial literacy.

Noah Berkson: And you're also helping them connect them to a lot of these opportunities to build their own brands.

Lucy Guo: Yep. And we're working directly with creators on this as well.

Noah Berkson: I was really shocked by. I didn't realize the extent of that. Like, I went to some dinner recently and there's like a guy from caa, there's a guy from UTA that both did brand. Just brand partnerships. As in, like, just finding brands for creators to, like, have equity in and, you know, build. And I just didn't realize that it was as intentional as it is.

Lucy Guo: Yeah, I would say most creators, they make the majority of their money through brand deals, like on passes. They make more money than their brand deals combined. But like, most creators, like, we don't have every creator obviously on this planet on passes. And if you talk to your creator, like, they'll tell you, like, all their money is from brand deals. Which is why there's like, managers and agents that are both out there scoping for brand deals for these creators. And why I don't think that like, you know, passes interrupts everything. Because it's just like, okay, cool. If we found creators brand deals and these two people are finding the brand deals, then that's just more brand deals and more money for creators. We're not really, like, competing against each other except maybe who's their favorite.

Noah Berkson: And a lot of these large talent agencies, they like what you're doing and you can build partnerships with them.

Lucy Guo: Yeah, I mean, we work with a lot of talent agencies. We tell them what we're looking for in a creator they know creators that we might not know even exist. Not to mention that pretty much every large creator is rep by talent agency. So we work with them to convince the creator to come on and then they take their percentage so they're happy too.

Noah Berkson: I think it's also very challenging because anytime, if any creators want to do anything, like, outside in the, like, more adult area, it's really challenging because then most brands won't ever want to work with those creators. They're going to have a hard time getting like a Colgate, you know, like a Colgate deal when you're doing anything on the adult side.

Lucy Guo: Yep, we've noticed that too. Which is why, like, a lot of creators that were on of like, want to switch over to passes and we tell them that like, they're just not going to make us much. And the reason is because I think that like, even if you're doing completely like G rated content content on of, I think that a lot of people spend money on a false hope that if they spend enough money then maybe you'll start doing sexier content versus there isn't that false hope on passes. So the amount that each person is willing to spend is probably just lower. To be quite honest, we've seen creators switch from passes to of, and they do make, I would say just slightly more on of. But when they come from of to passes, it's a big drop to the point where we warren creators were like, if you want brand deals, I guess this is worth it for you, but like you're going to be seeing a lot less money. And I think that like the creators that do choose to go on of, they make that calculation where they're like, I'm just going to make so much money and invest it that I won't ever have to have a brand deal again.

Jess Mah: Yeah, interesting. Yeah, it's just a very different path, you know?

Lucy Guo: Yeah. I mean like you'd be like Corinne Kopf who made like, what was it, $52 million on of something crazy. Wild.

Noah Berkson: Yeah, wild. And hopefully you invest that really well and you have good people around you to help invest that money.

Lucy Guo: Yeah. And like, from what I understand, she lives a pretty like, chill life. Like I think she lives on a farm, doesn't really go out, et cetera. That's what I heard. I don't know if it's true, but yeah, like if you invest it well and you're not like an idiot with the spending, like that is enough money where like you don't have to work. Again, like, we have so many creators on passes that do like, you know, over 100k a month, like some closer to half a mil a month. It's like if they don't spend that money and they could technically just be on us for like a few years and that could turn into generational wealth. Yeah.

Noah Berkson: What are a couple things people don't know about you? That from the outside they wouldn't know this, that you're like, but if you knew the real me, this is what you'd know about me.

Lucy Guo: Hmm, that's a good question. Because I put a lot of my life out there. I would say that, like one thing that I think that people don't realize, like what I really love is nature. So whenever I'm like figuring out a travel, destination, I always look for like the like highest peak mountains to be able to hike. And then I like Google like the views to make sure that it has like the views that I want. Because I'm very like kind of specific on what I want. And then that's like kind of how I choose to travel and I'm very spontaneous about it. Then I'll just like, you know, find like a three day window I have maybe and go. Unfortunately haven't really been able to travel since passes. But like this winter for example, like over Christmas maybe I'll go somewhere. At least that's the plan. So really, really like nature and just like views. My favorite trip I've done is South Africa because you know, I was just like in the jungle with the animals. Like literally lions are coming up next to us. Elephants were like in my backyard, et cetera. And they were like, it was like truly in nature, which is cool. Yeah.

Noah Berkson: Do you, do you go by yourself on these trips or do you like to go with friends, family?

Lucy Guo: It's a mix. Like I'll go by myself or I used to go only by myself. Like I preferred solo trips just to like, you know, be in my own thoughts. But recently I think that I have been more scared for my safety as like my public Persona has gotten more popular or like more well known. So I think like now I would want to go with somebody. I would say like the most recent trips I've made have been solo. But. But yeah, like I was just broken into, for example, in my West Hollywood home. And that scares me. Right. Cause I'm like, okay, cool. People are watching my stories and seeing where I am to like target me. Which is not the best feeling in the world.

Noah Berkson: What happened?

Lucy Guo: I posted that I was on a plane to Vegas. My friend was having like a last minute wedding. And literally right after I posted the plane that night, someone came and they broke a window and tried to steal stuff. But I had roommates home and they were really surprised I had people home. Like they definitely did not expect I had people. So they ran off. Wow.

Noah Berkson: Do you have people, do you have roommates or like just people that like crash at your place for time or something?

Lucy Guo: So they were temporary roommates. They're moving out in December. I'm really sad about it. And after that experience I'm like, I do not want to live alone. I'm almost considering convincing one to stay. I mean like, you stay here for free, you don't have to pay. Just like, don't leave me.

Jess Mah: That is, that is the Move. I've had. I've had veterans living in my house.

Lucy Guo: Yeah.

Jess Mah: Like, armed, like, you know, ex US army or Marine Corps in one of my guest bedrooms.

Lucy Guo: Yeah. It just makes you feel safer. Cause, like, I'm just scared to, like, touch a gun, for example. But, like, they have guns and, like, that makes me feel safer.

Jess Mah: And they get free rent.

Lucy Guo: Yeah.

Jess Mah: And it's a good trade. It's a great trade. But it's kind of weird having lots of guns in your house. You know, I just don't want to see them.

Noah Berkson: That's terrifying to have to worry about that, though. That actually, like, even has to be a thought that, like, I have to worry that people are going to break into my house.

Lucy Guo: Yeah, no, I'm upgrading my security, but. And I already have, like, started upgrading it, but I'm adding a lot of, like, little barb. Like, I'm adding barbed wire. I'm adding, like, spikes everywhere. So, like, if someone tries to hop this thing, they're gonna get shocked. And, like. Oh, my God.

Jess Mah: Wait, so what are the other challenges of being well known, successful, rich? Everything.

Lucy Guo: Like, honestly, I would say the perks outweigh the cons. So I think the main con is that, like, I have to worry about my safety. But besides that, everything's great.

Jess Mah: Yeah, that's not bad. That's a good trade.

Noah Berkson: Who do you spend the most time with outside of, like, your team at work?

Lucy Guo: I mean, I would just say my homies that I've known for, you know, the last few years. They're amazing. They cook for me. They feed me, like, food at restaurants. I think, like, a common misconception is, like, oh, yeah, like, if you're rich, people are only friends with you because, like, you're rich. And I'm like, But I don't really pay for anything. Like, my friends just do everything for me. And I think what people don't realize is that, like, rich people are friends with rich people or, like, successful people. And, like, maybe some of my friends don't have as much money as me, but they're also, like, gentlemen, and they pay for everything. Like, I haven't had to take out my credit card at dinners. Like, you know, they cook for me.

Jess Mah: So what percentage of your closest homies are in the successful business camp versus, like, just creatives and other.

Lucy Guo: I mean, my creative friends are also very successful in that, like, they make a lot of money. I would say, like, in terms of, like, successful business versus creatives, it's probably like, 50. 50. But, like, I think I generally Gravitate towards people that are, like, hard workers. And, like, hard workers are going to be successful, especially, like, closer to my age in, like, whatever they're doing. Right. So. Yeah.

Noah Berkson: Have you met anyone in the last, like, let's say the last this year that you're like, this person is going to be in my life for a very long time.

Lucy Guo: I mean, I think the first person that quite literally comes into my mind is my new cbo. If he ever tries leaving, I'm going to literally lock him up.

Noah Berkson: Do you make. Because you're very social, you're meeting lots of people. I bet every week you're probably meeting 20 new people. Do you make friends easily? Are you a little bit guarded? And you kind of keep the people that you have close to you and don't make a lot of new friends.

Lucy Guo: So I think that I have a core set of friends that I keep very close to me that I consider they would take a bullet for me. I would take a bullet for them. But I would say, like, my problem is I might be, like, a little bit too friendly. Like, for example, if there's, like, a concert coming up and, like, I know I have extra artist passes, and, like, I could, like, literally reach out to someone that I don't even know the name of, Basically, I'll be like, hey, like, I know you like this artist. Like, do you want this pass? And then, like, suddenly they think that, like, we're best friends and, like, I will not remember them next time I meet them. And this happens so much where it's like a running joke where, like, people come to me, like, lucy, you've met me, like, five times or 10 times. Or, like, I'll give a hug, like, oh, my God, so good to see you. I'll just be like, I don't remember your name. Like, even at f one weekend, like, the number of people. Like, I had, like, 10 people come up to me, hugging me, like, scream my name, be so excited to see me. I didn't know any of their names. Oh, no. Like, oh, man. So I would say I am extremely friendly to the, like, everyone. Like, you know, they're just like, oh, my God, we're best friends. And I'm like, oh, so bad with names of basis.

Jess Mah: Yeah.

Noah Berkson: Which is probably really helpful in what you're doing, though, right? Because you need to make everyone feel like you're, like, their best friend. And it's also, like, a helpful way to meet more, I assume, more creators. I assume more people that are going to go on passes.

Lucy Guo: Yeah.

Jess Mah: It Seems like you are generally open to new relationships and friendships and that's cool.

Lucy Guo: Yep. And there are just people that are like, you know, I. Like, they're amazing and I bond with them and, you know, we're hanging out, like, all weekend long, but because I meet so many people, like, by like, three weekends later, I will have forgotten their name.

Jess Mah: Yeah, I get that.

Lucy Guo: Especially if they're like, you're not in la, so I'm not seeing them, like, again right away. Yeah.

Jess Mah: What's that phrase you used? Emotional recency or something?

Lucy Guo: Emotional retention.

Jess Mah: Emotional retention. Yeah, like that.

Noah Berkson: Emotional retention.

Lucy Guo: That's high emotion. That's high Friendship retention.

Noah Berkson: Yeah.

Lucy Guo: Yeah. You'll have to meet me like, five times before I remember you.

Jess Mah: Yeah.

Noah Berkson: It's very cool, though, because I think a lot of people, as they get more success, they become a lot more closed, and they become more closed off and, like, isolated in maybe the group that they're in. And they kind of are just like, we just stick with this.

Lucy Guo: Yeah. And I see that a lot with, like, my super successful friends or, like, my super old money friends. Like, they refuse to make new friends. Like, I'll be like, oh, can I bring a friend over to your place? And you're like, absolutely not. You owe me. And I'm like, well, no, I don't want to go over because I'm with, like, a friend that I don't want to ditch.

Jess Mah: Why do you think the old money people in particular are so bad at making. Making new friends and why are they so. Because, like, so many people have lots of money now. It's not that.

Lucy Guo: I think they got more paranoid because, like, from a very young age, they were probably taught, like, people will use you for your money and, like, your safety will be compromised, etcetera, Versus new money. We grew up very normal. Right. And, like, we understand what it's like. Yeah, exactly.

Jess Mah: It's like hustling.

Noah Berkson: It's a really sad way to live, though, to not be able to go make new relationships and feel like people are just out to get you.

Jess Mah: Yeah.

Lucy Guo: I will say that, like, they're very, very close to the friends that they have. Like, they've grown up with them. What I've realized is, like, pretty much every old money family is a connected. Like, I can guess if someone's old money just based off our mutual friends on Instagram, I'll be like, oh, you only know these people, therefore you must be old money. And it's like, right. Pretty much 100% of the time.

Noah Berkson: Could you. Could you end up with one of those people if it's like they were very well off, but it's not, it's.

Lucy Guo: Not earned, I don't really mind. But I would want them to at least like be working. I think that I have a lot of friends that are old money and they're like, schedule is literally like wake up at 6pm, get ready, go to dinner party, fall asleep at 6am and repeat. And I don't think I could be with someone like that. Like I would want them to like at least have some ambition still. I think it's like, like I would never penalize someone for, for growing up luckier than someone else. Right. As long as they're still like hardwood. I would almost say it's maybe more impressive that they're like so hardworking and motivated in that it's so much easier to be lazy in that environment.

Noah Berkson: Yeah, I was talking to someone the other day about this concept because I think a lot of those people that as you get more successful, you're more isolated, whatever, you stop doing things, you stop trying to meet. Like you kind of don't want to like cold out reach, reach somebody. Like, you get. It almost makes it weirder for people. I've been so successful, I'm not gonna like cold email this person. And I'm like, they just need like a networking person, right? Like a chief networking officer that just goes out and like finds good relationships that are kind of like trusted and vetted for you. I think a lot of people would benefit from that. Cause it would like open up that container for them where they feel a little bit more, a little bit more open to meeting people, knowing that like, hey, these people aren't just like trying to get things from me.

Lucy Guo: I feel like there's always so many events though where it's like, you know, you're at the event and you know that every single person at that event is like pre qualified.

Noah Berkson: Yeah, yeah, that's the F1 Super bowl type things or what are you thinking about?

Lucy Guo: I mean, I would just say like, for example, like if there's like an art event, for example, and it's being hosted by like a certain group of people, then you know that everyone there is probably pre qualified. But I will also say that like, I wouldn't say F1 is like totally pre qualification because I think that old money wealth is a lot. I don't want to say snobbier, but in some way it's like different. Right? Like, I can't really explain it, but the vibes are not there. Like, they might, like, admire someone in tech that has, like, multiple billions, but doesn't necessarily mean they'll, like, want to be friends with them.

Noah Berkson: Yeah. Okay.

Lucy Guo: Even if that person has significantly more money than them.

Noah Berkson: Yeah.

Lucy Guo: Yeah.

Noah Berkson: Fair. Yeah.

Lucy Guo: Yeah. Doesn't really make sense to me. Like, totally. But, like, I see it.

Noah Berkson: Yeah, I totally know what you're saying.

Lucy Guo: Yeah.

Noah Berkson: What else. What else are you hacking? Like, what else are the things in your life today that you've, like, found a way to hack?

Lucy Guo: I mean, hotels. But I'm sure you have the same thing. Do you not?

Noah Berkson: No. Maybe.

Lucy Guo: Yeah. What?

Noah Berkson: You know, I actually though I met a guy who sold a company to Gusto somewhat recently, and he was like, I just. He's like kind of a. He's a tech guy. He's like kind of like a not. Not nerdy, but, like, really intellectual, like, engineer tech guy. And he's like, I realize that hotels will, if you're like a, you know, like an influencer or somewhat famous, right. Will give you either, like, comp rooms or give you huge discounts on rooms. He's like, so I bought an Instagram page with like 100,000 followers, and it was like, not very much. And he's like, they, like, I have someone post a couple of pictures of me, and then I have my assistant reach out to the hotels. I, ahead of time, be like, he wants to come stay at the hotel. He's very, like. He's a very, like, famous, you know, influencer or whatever. And a lot of times they'll just give him discounts on hotels. And he's like, not that guy at all. Like, he's just.

Lucy Guo: I know a girl that literally bought 2 million followers on Instagram and, like, buys fake engagement per photo. So, like, her photos will get, like, thousands of likes and comments. So it looks very real, right? Unless you, like, know what fake comments look like, which, like, you know, it's just emoji spamming, essentially. Like, if it's enough emoji spanning, they're fake comments, even if the accounts look real. And she just gets free, like, flights, free hotels, et cetera, everywhere at these, like, five star resorts. It's insane. Like, this is like a brilliant, like, most brilliant hack ever, except also it's kind of scamming people. And, like, I think that, like, eventually at some point she may get sued. I think they, like, made a law saying that, like, buying fake Instagram followers is now illegal. Really, something came up or, like a bill, I don't know. But, like, someone is trying to, like, ban buying fake followers because it is harmful to businesses. If you know, you're dumb and you're not checking for these things, but, like, you know, a lot of them. Like, if it looks like there's fake engagement, if there is fake engagement, a lot of people just, like, won't know.

Noah Berkson: All right, so hotels, anything else?

Lucy Guo: Yes, hotels. I mean, I don't know. I'm just extremely cheap. Like, one thing I do is, like, when I go to restaurants, I go check to see if there's, like, you know, a deal on Uber Eats. So last restaurant I was at, they had two for one for spicy vodka, and I literally got the, like, spicy rigatoni and bought it on Uber Eats and had it delivered to my table in plastic boxes because it was two for one, which is a great deal, by the way. I just saved myself, like, $27.

Jess Mah: But. But at a certain level, it doesn't make sense to optimize that much.

Lucy Guo: I think when I first did my secondary and I had money, people were so confused because I was still taking Uber pools. And they were just like, why are you taking Uber pools? Like, you may have enough money and like, like, don't you value your time? And I'm like, well, I'm meeting interesting people in a car. You know, like, there are some pretty cool conversations that happen. Actually, my Uber driver is the reason why we got our pre seed round for scale. That's a whole nother thing.

Noah Berkson: Can you tell us. Can you tell us about that briefly?

Lucy Guo: Yeah, I mean, he was just saying, hey, do you know, like, this guy Paige Craig, he, like, coined a term in Silicon Beach. And I was like, oh, no, I don't. And then afterwards, you know, we have a conversation about him. I look him up on Twitter, he's already following me. I sign on his DMs, tell him I'm thinking about doing YC, and I have a startup idea. We meet in, like, LA a few times, and he's like, I want to invest a million dollars.

Noah Berkson: Did you ever go back to this Uber driver and be like, hey, thank you so much.

Lucy Guo: I have no idea who they are. Yeah, but, like, I just have, like, a lot of interesting conversations in, like, these Ubers. So. But for me, I was like, oh, like an Uber fool isn't really a waste of time. Plus, I could always technically be working my laptop if I'm saving money. So, like, I think one thing that really annoys my friends now is that I always order Uber X's, and they're just. They just get so Bad. Like, they were like, we just flew on a private jet and you ordered an Uber X for us to the hotel. And I'm like, they're like, we just landed on a private jet and you got us a Toyota Camry. And I'm like, what's wrong with the Toyota Camry? But, like, my. My guy friends get annoyed. My girlfriends are like, chill. But like, I think, you know, guys are always trying to impress the girl or make an impression, whatever, like, they care about. So, like, when I, like, order the Uber X, like, I'm banned from ordering Ubers now. Like, my guy friends are, now they just pay for the Uber. But, like, they got so mad at me at some point because they were just like, we can't write another Uber exclusively.

Noah Berkson: Do you feel like you want to not have, like, much liquid cash available? Because, like, then you just don't even. Then you don't even think to do those things right? Because now it's like, well, I'm just going to be frugal because I don't have a bunch of cash to.

Lucy Guo: I mean, I think that, like, I will always, like, ride Uber X's no matter what. Like, my. My assistant, he was like, do you want me to get another car? Because he drives, like, a pretty old, I think, Toyota Camry or something. And I'm like, no, I really don't care. Like, your car is fine. But I think there's, like, certain things that, like, I really like fashion. And, like, if I just happen to be in an expensive store and see something really nice, I might, like, point at it and be like, ooh, I want. And by not having liquid Clash, it prevents me from doing stupid things like that. But I also love, like, cheap stores. Obviously, like, half my stuff is she. But I will say that, like, you know, sometimes Dolce and Gabbana make something really nice.

Jess Mah: Lucy super fond hang. I mean, it's. It's been years that I've had so many people say we should hang out. And I don't know if it's just the Asian connection or what, but I'm glad we got to do this. And it's just rare to meet another woman who's been really successful but who just also, you know, is so authentic and raw. I think a lot of other, like, for all women in general who I've interviewed or chatted with in a more public setting, a lot of them tend to be really guarded, but you're really out there and, like, just your true self. Why do you feel able to do that?

Lucy Guo: I think it probably has to do with confidence. And just like, I love controversy. So I don't really care about, like, people's opinions of me versus I think a lot of people are told to, like, make this perfect image of themselves. Like, even. Even during backend, right? I would send out these tweets and I would literally have LPs call and be like, what was this? Why did you tweet this? And blah, blah, blah. But I just don't care versus I think a lot of women feel pressured to present a perfect person due to their career.

Jess Mah: So then where did you learn that you're okay with controversy? Because that also goes against the strict conservative Asian parenting.

Lucy Guo: I mean, I think that the confidence really helps. Like, you know, before, like, bullying, for example, would really hurt me. I was bullied when I was in elementary school, middle school and high school. Like, people would make anonymous accounts on the Internet and, like, spam me hate messages on aim on, like, Ask fm, etc. And like, as I grew more confident, like, I just realized, like, well, these people, like, I don't even know who they are. I don't interact with them. Like, I don't think about them. Like, they're literally paying attention to me for, like, like giving brain power to me. And I'm like, just out here living my best life. So I think it just, like, I feel it's almost a compliment for me nowadays. Like, it strokes my ego if someone's like, hitting on me because it's just like, oh, wow, like, I'm really taking up a lot of brain space. Like, cool. And then like, on the other end, you have, like, I have a lot of fans that like, really help as well, where there's like, we love how authentic you are and how open you are, et cetera.

Jess Mah: So it's good for business. Net Net. The downside is you might have some employee or an investor who's like, ah, that's like, so out there and crazy. But yeah, but if you look at the overall picture, it's better for you than not.

Lucy Guo: I think it is. Yeah, Because I get more attention, which, like, the creator economy is like an attention economy, essentially. And really the creators, I would say, connect with it more. Like, they're like, oh, you're so fun, you're so open, you're so cool. It really is just like more. More of the professional setting. So, for example, if I were to raise another venture fund, I think my Twitter would probably get scraped or I should lock my Twitter down to private.

Jess Mah: But would you really do that?

Lucy Guo: I prefer angel investing. For the moment at least. It's so much easier.

Jess Mah: Yeah. When you've had an LP or an employee complain about being raw or authentic, how do you handle it? What do you tell them and how do do they react?

Lucy Guo: Honestly, I'm pretty good about it. I'm just like, okay, cool, I'll delete that. Or, oh, I see your perspective, which I do. And I'm like, you know, I'll make note. Like, I think I have gotten a lot less controversial on Twitter, which has actually upset some investors.

Jess Mah: They're like, oh, man, there's no winning.

Lucy Guo: They're like, I like the old Lucy.

Jess Mah: Yeah.

Lucy Guo: They're like, oh, man.

Noah Berkson: They like the controversy.

Lucy Guo: Yeah. Well, Lucy, usually the crypto investors.

Noah Berkson: And you also lost a lot of money. In crypto, you made a lot of money, but then subsequently lost it.

Lucy Guo: Are you talking about the meme coins?

Noah Berkson: You're talking. Well. Oh, well, that's a whole other thing. You bought bitcoin a long time ago, and that got hacked.

Lucy Guo: No, they got hacked. It got seized by the FBI, so I left it on an exchange. I never put it in a wallet, and obviously that was dumb of me, so I guess the exchange got seized by the FBI, so now it's all just poof, which sucks. But, you know, life happens.

Noah Berkson: What meme. What Meme coins? What, you got a story there?

Lucy Guo: I don't know the story. I've just been buying in at the wrong prices. I've been selling at good times. So, like, I was up, like, 10, 20x on chill guy, and then, you know, I got FOMO, and then I bought in at a bad time, and. Because I thought it was still going to go up. No, I'm down a lot, but it's okay.

Noah Berkson: Are you gonna keep doing that? Is that just, like, kind of fun for you?

Lucy Guo: It is fun for me. I think I'm gonna continue doing it with very small amounts of money.

Noah Berkson: Okay.

Lucy Guo: Yeah.

Noah Berkson: Well, Lucy, you have awesome energy. It's been really fun to have you here. Hopefully we can do this again sometime. Congratulations on passes and everything that you've accomplished there.

Lucy Guo: Thank you.

Noah Berkson: We're fans rooting for you.

Lucy Guo: Thank you.

Noah Berkson: Looking forward to Barry's tomorrow.

Lucy Guo: Awesome. I'm excited.

Noah Berkson: I'm gonna see if I can beat you on a tre.

Lucy Guo: That's not possible.

Jess Mah: I'll be sleeping.

Lucy Guo: I actually did meet a guy in Miami the other week that crushed it. I've never felt so incompetent in my life.

Noah Berkson: Really?

Lucy Guo: Yeah. He was keeping up with me. Not unlike the longer runs, but the very competitive I was. I love it, though, when, like, people are actually racing me. It's fun. I find it fun. But I was like, man, this guy's good. Like, he was pushing me, which was good, because, like, sometimes I'm, like, lazier on, like, certain parts of the run. And I was like, oh, you're going at the speed. I have to go at the speed now.

Noah Berkson: Hope to give you a run for your money tomorrow.

Lucy Guo: Good luck.

Noah Berkson: Well, thank you. Thank you again for coming.

Lucy Guo: Thank you.

Noah Berkson: This was awesome.

In this podcast we talk about the following.

• Helena’s Mission: Henry Elkus founded Helena as a problem-solving organization that implements solutions to major societal challenges—through nonprofits, businesses, or legislation—based on first-principles thinking.
• SHIELD Project: One of Helena’s earliest wins was helping secure the U.S. electrical grid against threats like cyberattacks and solar storms, leading to passed legislation and executive orders.
• MDMA-Assisted Therapy: Helena invested in the rollout of MDMA for PTSD treatment (via Lykos), supporting FDA approval efforts and advocating for psychedelic-assisted mental health care.
• America in One Room: Helena brought together a representative group of Americans for structured deliberation on political issues, significantly reducing polarization and shifting opinions—proving the power of face-to-face democracy.
• Nonpartisan by Design: Henry emphasized the importance of staying politically neutral to effectively implement change across divides—structuring Helena to avoid typical incentives that corrupt mission-driven work.
• And many more.

Video

Watch the full episode on YouTube here.

Or watch it below:

Full Transcript

Henry Elkus: I kind of had what, like a one-fifth life crisis, shall we say, in college? Like everybody, we're doing like 20 Manhattan Projects in parallel as a species right now. And we've gone, we barely made it through one, and we're doing like 20. A lot of people fail because they're actually grasping at these straws of, like, the 1% of somebody's time. I want to dedicate the rest of my life to building an enduring platform that can actually, in a non-BS way, address societal problems.

Jess Mah: Henry, what is up? Welcome to the pod.

Henry Elkus: Thank you for having me. It's great to be with you guys.

Jess Mah: It's a Tuesday, end of the day after work. Thanks for joining us. Really briefly, tell us about what you're up to, who you are, and what you're passionate about.

Henry Elkus: I'm Henry Elkus. I'm founder and CEO of an organization called Helena. Sure, we'll talk a little bit about it. I was born in LA, grew up here. I was a ski racer. Randomly fell in love with reading late. It became a huge part of my life, and then I have dedicated the last, say, nine years—now it's been a while—to building this organization that we're at the very beginning of, and I'm here talking to you guys.

Noah Berkson: You started ski racing. Was that at a really young age?

Henry Elkus: Yeah, I was—I mean, I just loved—I love sports. I mean, for the first period of my life, I was really unintellectual. Actually, when you're a teenager, I don't think you're very intellectual in the first place. But there's a lot of people I know, I'm sure you guys know, that are like prodigies at a very young age. I was just incredibly interested in the human body and sports, and it was a very pure kind of focus at the time. I wasn't really multitasking. So yeah, I started skiing really, really young. I mean, before I could walk, just once or twice a year for a week or two, I just fell in love with the sport. I never got to be, you know, Olympic level or anything of that nature, but it was a huge, huge part of my life.

Jess Mah: But people do call you a prodigy. And I've met many people who've said your ability to connect and network is insane. So on that note, I'm wondering if you could tell us about Helena. What was it like nine years ago, and what is it today?

Henry Elkus: Yeah, so I'll say really briefly what it is, and then I can give the background of why. You know, we're building a problem-solving organization that does basically the following three things: identify solutions to societal problems, conduct due diligence to figure out whether a potential solution should be implemented or not, which is obviously very qualitative, and then the third and most important thing is do our best to actually implement it somehow, whether that's providing capital, building it as a company or as a nonprofit or as a legislative arm. And we've built a portfolio of these projects over the last nine years. And so that's what the organization is.

Jess Mah: And has it always been that way from day one, or on day one were you only doing for-profit or only nonprofit solutions?

Henry Elkus: So the order in which we did it is kind of backwards, actually. So the first thing that we did was build a network called the Helena Members. Before we did any projects, then we built a nonprofit. And that, for about five years, was all we did. It was through a 501(c)(3), and those were nonprofit projects and legislative projects. And then we actually built the for-profit side. And so a lot of people, I think, actually start in traditional capitalism business. So we did it in a bit of an inverted way. There was a real reason to do that. As for your first question, was it always the plan to do it this way? My answer is yes. But I will say I had this amazing—somebody said something to me that there's this thing called the—like, Peter Thiel calls it the reverse founder syndrome, where you ask somebody like 10 years in, like, did you plan it to be this way? And there's so much, like, accumulated trauma in this person's brain from having to go through the process, and they've kind of gone through this narrative so many times that they kind of simplify it. And I'm sure that, as I would live it through again, it would have been a much rockier road than my brain tells me it was. But with all of that said, yes. I mean, when I was in the dorm room and we were building this at the very beginning, it was this idea of actually, in what meticulous order should we build this structure for it to stand on its own and work and not have the incentive issues that a lot of other organizations that have tried this failed with?

Noah Berkson: How did you originally have this idea? Because you're in college when you start this. Are you thinking, I'm going to go start a business that isn't a business and makes no money but starts to solve societal problems? How are you thinking about this?

Henry Elkus: So I kind of had, like, a one-fifth life crisis, shall we say, in college, like everybody does. And I—

Jess Mah: It's very early, yeah. Well, I just—

Henry Elkus: I had the thing of kind of, okay, what do I do with my life? Like, everybody's—and this came around the time that a lot of my friends defaulted into, okay, I really need the Goldman internship. I was at Yale, you know, fancy pants. And so everybody was thinking, like, what is the next step? And I kind of had the—like, the panic, probably born out of laziness, to be honest, of, like, is this really what I want to do? But that kind of set me into, like, a search function of what do I want to do with my life? And it was around that time I really started to become fascinated, oddly, with the role of institutions that solve societal problems. Basically, as a species, we—we do this. Like, we—we've decided to rely on organizations to solve our societal problems. And that was fascinating to me that that's, like, a thing that we do as a species. And there's a set of organizations that we rely on in capitalism and government and think tanks, NGOs, to do this. The problem that I was very interested in as a college student started with the Manhattan Project, which is we had this kind of moment in which we created a technology in the nuclear bomb that was instantly global. It was instantly exponential, and it completely rewired the way the world worked. And it was—obviously, there have been many times before, but it was a great case study of just breaking institutions that solve societal problems. Because we created this nuclear bomb and we said, wait a second, all our geopolitical framework for how the world works just got broken. The Westphalian state system, which says this—oh, we can't do that anymore because now we can destroy the world. And there's this Venn diagram now of people that have access to this thing that they could press a button and likely end humanity, and then people crazy enough to do it. And those circles are converging, and we—if you just read history, you can see how the world almost ended: Cuban Missile Crisis, all this. I was fascinated with that. And then I'm sitting in college in, you know, the 2010s, you know, and going, holy shit, we're doing, like, 20 Manhattan Projects in parallel as a species right now. And we've gone—we barely made it through one, and we're doing, like, 20. So then you retrofit that back in, and you go, there's these institutions that we rely on to solve these problems. The vast majority of them were built way before the Manhattan Project. Some of them were built in, like, 1500. We still use them. They almost broke with the Manhattan Project, and now we're doing so many more versions of that. Who is innovating in the white space of trying to reimagine those models for the 21st century so that we can survive as a species? And I wasn't thinking of it in terms of, like, I want to be involved in that. It was more just, like, that's a very fascinating intellectual problem. And so I think with the freedom of, like, not having a job or not feeling like I had to do something, I was thinking about that very deeply. And that was actually what made me think, okay, I really want to do something in this space. I don't know what it is, but that's, like, this is a problem that is, like, the sexiest problem in the world to me. It's the most important one, and I want to spend the rest of my life involved in it in some way, but I don't fully know how. And that was kind of the impetus.

Noah Berkson: How did that first piece come together? What was kind of the first puzzle piece that was, hey, we're going to start this new thing? I'm going to bring people around me to be able to build a team or have a partner. What did that look like?

Henry Elkus: I mean, it's very freeing when you don't actually—when you've not actually done anything, it's very freeing because you get to put the pieces together how you want them and reiterate and reiterate. I think for me, it was two things. It was studying existing organizations that had tried to do this and seeing how they had failed or what they were limited by. And I was very interested in that. For example, there are some really amazing nonprofit organizations, and I've benefited by being involved in these and working with them. But I've noticed that they have this idea, which is, let's bring together incredible people to address societal problems. But the structures of these organizations oftentimes say, okay, well, let's monetize it by having a conference and selling content. But then you're selling access to people's names, and then are they going to be involved in private to actually do these projects? And so on and so forth. And so there was, I think, a laundry list of, like, things looking at past organizations that had done this and said, okay, this doesn't work. And then I'm concurrently going, if I were to do this from scratch and I had infinite resources, how would I do it? And just thinking I would actually do it very similarly to how a family office would do it that has infinite money is, you wouldn't think, oh, I'm going to build this, I'm going to build this. You would actually do the reverse: you would just try to accumulate the smartest kind of collective intelligence of people around you, hear the best ideas, rely on that group to do diligence on those ideas to figure out which to actually do. And then if it happened to be that the solution to a given problem was, let's go pass a bill, you wouldn't say, oh well, I'm a for-profit and I don't pass bills. You would just say, what do I need to do to go pass this bill? And you would do it in that corner. Or if the best solution was, let's build a business, you would incubate a business. And so it's from that kind of first-principles-like idea that came out, okay, what if you could actually try to build an organization to do that? The problem being we didn't have the money to start it or those resources. So you have to build it from scratch as opposed to from the top down. And that was the chicken-and-egg problem that we still have to solve. Even nine years in, we still, every single day, deal with this. But it was a really big issue when we were starting out.

Jess Mah: So there's this moral hazard of wanting to accumulate capital in order to do all these things. So how did you not get stuck only on for-profit projects and stay motivated to do nonprofit legislative work as well?

Henry Elkus: I'll say a couple of, like, prefacing things. The first is there's no way I could ever say—and if I ever say it, then somebody should slap me in the face—that we're doing it perfectly or that we are free from the incentive issues or the moral hazard that you're describing. That's number one.

Jess Mah: That's very honest. I appreciate that. Yeah, I know, I've struggled with that because I—I want to do everything you're doing. You have my dream job.

Henry Elkus: Oh, thank you.

Jess Mah: You know, and yeah, anyway, please.

Henry Elkus: So that's number one. Another reason—I agree with that question, and I'm not trying to avoid it. I will answer it.

Jess Mah: Yeah.

Henry Elkus: One thing that's not discussed enough is there are a lot of people that make billions of dollars in the hedge fund industry or building a tech company or so be it. To do that is an incredibly hard thing to do. But it also—it's a game that you are playing, which is capitalism. And there's a way to win that game that builds a specific mental model of how the world works, which is a very accurate mental model of how the world works. But it is not complete because it is only in one modality of getting things done, which is capitalism. One of the things that is the moral hazard is that people accumulate that wealth, and then they say, now I'm going to go do philanthropy—the definition of the word philanthropy, for the good of humanity. But then they say, because I made my money in this hedge fund world, I'm going to do capital allocation like a hedge fund to solve these problems. Or because I'm a VC, I'm going to do venture philanthropy because that is my mental model of how the world works. And it's very challenging once you are calcified in doing that. Another great example is academia, where somebody gets tenure by delivering one idea over and over. But then what if you have tenure 30 years in, and then you're informed that that idea is wrong? But your house, your salary, your Wikipedia page—all of that is predicated on the fact you had that idea. You get calcified. So those are two reasons why your question is really good. So our question was, is there any way to free ourselves from that? And I don't think the answer is no, because people have egos and people like money, and these are incentive structures. With that all said, our idea was, do the nonprofit first. We'll first accumulate the network, demonstrate to that network that we're doing things from the bottom of our heart, that we're trying to solve these problems. We're not trying to do this to just make money. Then try to prove ourselves operationally, zero to one, doing nonprofit projects that don't make us wealth. And then from that point on, with that level of trust, then try to build the most ethical, the best kind of oriented for-profit that we can, that is rooted in that legacy. And it is absolutely the case, though, that when you run a—when you don't have money to start with, you have to raise money from investors. Those are your clients. And so you have to set up that incentive. My argument, though, is that of the kind of evils that you have to deal with, there's a very direct relationship you have with a limited partner in a fund or an investor, which is, they are committing capital to you for an express purpose. If you're going to place it in these types of strategies, with these types of return profiles, and when you silo that, and it's actually clearly defined—to me, that's a lot better than saying, hey, I want you to join the board of my organization, pay a million dollars a year, and then there's kind of a backhanded thing of, are you going to do this for me or do that? And I think that's a huge issue.

Jess Mah: It's unclear then what the drivers are in a relationship like that, whereas LPs in your fund—it's just very black and white, you think?

Henry Elkus: I think that's one thing. I think the other thing that we benefited from was that because I'm not Bill Gates, because I don't have that—I'm not nearly as successful, I don't have that track record anyway, not yet. I'm not a known entity starting an organization like this. I think we benefited from the anonymity of—it's not about me, it's about the actual work, and it's about the collective that we're putting together or my staff as well. It's not about—and the great people we've worked with. And so I think that when somebody starts with, hey, I made $10 billion, I'm going to go do this thing, there's this implicit issue that they actually end up dealing with, which is maybe they've made enemies to make that money. Maybe they've kind of entrenched themselves in one pocket of society that prevents them from actually doing the important political work they need to do because they've defined themselves as a Democrat or a Republican. So I was able to start largely without those issues. And I think building it from a more relatively pure base was beneficial to us.

Noah Berkson: And you're this—you're a young college student. The members that you have at Helena today are CEOs and titans of industry and government officials, Nobel Prize winners. How do you get their attention? Because you're a college student, you're young, probably naive, and you say, hey, I want to help solve a lot of the world's biggest problems to people that have the capital to probably solve the world's biggest problems—maybe they haven't been successful in it. How do you get their attention?

Henry Elkus: This was an unbelievably easy thing in retrospect. And if we had any insight, it would be this, actually. And I'm not going to say anything that's revolutionary. And I'm sure a thousand other people have had the same idea. But here's exactly what we do and what we did when somebody joined the organization. We sit with them, we do an onboarding just like any other membership, and we just literally ask them the following question. We ask them a lot of other questions, but the following question is the core question. We say, when you look at the next, like, tell me about the next five, 10 years of your career—not, like, what school you want your kids to go to or, like, the 1% that is your—that is outside of that—but, like, what is the 99% of, like, your schedule? Because these people are busy. Why are they busy? Well, because there's a large portion of their schedule where they're doing things. So tell me about that. Tell me what, exactly, in as much detail as you can, what you want to accomplish in the next five to 10 years. When you go to sleep at night and you worry that you will not accomplish those things, what asset do you not feel like you are going to have access to that you need to have access to to accomplish those things? It's an incredibly simple question. And so we all go to—and I only asked the members that because that was what I was asking myself, going to sleep. But you go to sleep at night, and you're an entrepreneur, and you say, I deeply believe in my business model, but I don't have technical expertise in this one area. Or I need a massive amount of capital. I would imagine if you ask Ken Griffin or Bill Gates that answer, it's not, I need more capital necessarily. It's, there's a specific area of expertise I want to have access to, or there's this or that. So we would get this information from the members when they joined, and we would essentially just have a mental dossier of what they need. And then the genius of it is—if there's any genius to it—is just, there's somebody else in the network that probably has the asset that they're needing to do their thing. And if you connect those two people together, there's actually an incredible value. So one of the first members was your friend—or our friend—Nancy Liu. Nancy—I remember seeing this click.

Jess Mah: She's one of my best friends.

Henry Elkus: She's amazing. And we, obviously—one of the benefits we can get to is a lot of the members were young and still are. And so there was, I think, a camaraderie of us being kind of in our 20s or early 30s. And I just vividly remember the first couple member meetings with Nancy where I sat with her and said, tell me exactly what you need. So this is all a long way of saying that when you've expressly told somebody, I need this asset, and they call you up and they say, I have a person that represents that asset—could we go and set a meeting up between you two? And let's have a conversation. And it's no bullshit. It's just operational. Then they say, yes. But if you go, hey, I want you to show up at my conference and do a talk, or I want you to do this favor for me, it is in the periphery of their time, and a lot of people fail because they're actually grasping at these straws of the 1% of somebody's time. And so it was just the no-bullshit, like, we want to do actual work. Tell me what you need, and we will try to bring you that. And then we had to do it.

Jess Mah: And how often do you think you were able to follow through on that?

Henry Elkus: Enough.

Jess Mah: Like 50%, maybe?

Henry Elkus: You know, again, reverse founder syndrome. So, like, I—I have such beautiful memories of the beginnings of the—of the member meetings because of just how psyched I was to be there. And so, to me, they were all super successful. In retrospect, if I was one of those members, I would probably be in those meetings, go, oh, you know, they set me up with this guy. But I actually, looking back at it, really think that we had—before we did any projects, before there was anything to show for the actual work—I actually really feel as though the beginning member meetings, which I have such fond memories of, were actually incredibly operationally helpful. It might be a better thing to ask some of those members than me, but I think we did a decent job, and I think that allowed us to engender the trust to actually then go, can we do our first couple projects and actually turn this into something operational?

Noah Berkson: Did you then use members to get other members? Typically, was that the—hey, now these people are involved, and I can go tell other people that they're involved, and so if they want to be involved—was that kind of the snowball effect, or how did that work?

Henry Elkus: Yeah, I think, you know, as word of mouth—we would, of course, if there was somebody that we really respected, that they were really engaged and they were very helpful, I would say, look, you are somebody to me that is very valuable to the organization for these reasons. And we like each other, and we want to work together in the future. There's a reason for that, which is that we have a mixed person—we have a matched personality—or we want to work together. Given that, my presumption is that the people that are in your circle are similar. So could you introduce us to the two or three people you think would be a best fit? And that was a way for it to organically grow at the beginning. Yeah.

Jess Mah: And how did they present Helena? Like Bob Hertzberg, who's a mutual friend—he spoke very positively about what you guys are doing. And he's a bigwig in California government. He, I believe, was the Speaker of the Assembly here in California, among many other things. And he supposedly helped you and sent you a bunch of stuff, but he knows everyone already, and he knows all the big funders to fund his campaign. So how did you convince him that you were worthy of his time and attention back before you were established?

Henry Elkus: I love Bob, and he's such a great example of this. So I'll just tell you a story. And this dovetails into the actual projects because Bob was deeply involved in one of the first projects we ever did during the time where we were transitioning from just this kind of, like, weird, like, what the hell is this group of members to, like, an organization that says it's trying to do projects, that has actually done projects? Like, what was that transition point? Bob was instrumental in a project we did called SHIELD that we're still working on in some capacity. And it's such a great case study. So if I can tell the story, please. So some of the early member meetings were with members of the intelligence agencies, national security. We have a really great contingent of—of people in our network there, and we're still involved with them. And we had a fascinating set of discussions that were essentially—to say it really simply—like, what are the things that could be existentially bad to the world? And then if there's a Venn diagram and the other circle is, like, what are the things that are, like—we already have the technology to address, but it has not been addressed yet—that it's, like, it's very dumb that we as a species have not solved this. There was something that kept coming up over and over and over again from these, like, heavy intellectual members—some of them in finance, some of them intelligence, some of them in defense. But it kept coming up, and I was interested because it kept coming up from Democrats and Republicans. And it was an incredibly bipartisan thing. And it was the vulnerability of the North American electrical grid to shutting down through many different—being crippled through many different reasons. One of them is a cyberattack from foreign adversaries into the SCADA systems, the kind of operating systems of electrical systems. Another example was coronal mass ejections from the sun, so solar storms that happen like clockwork. There was actually one in the 19th century called the Carrington Event. And if that event had happened today, it would be crippling. But back then, there just wasn't enough electric infrastructure for it to get screwed up. Another one is just physical attack. And then another one, very important, which has now happened since we started this project, is extreme weather. So wrap this all together—you have a very nerdy solution kind of issue, but it's one that's huge, which is, like, we rely on electricity for literally everything. One of the largest machines in the world is the North American electrical grid, and it can go down. And how do we address it? Well, we should update the software. We should put surge protectors and Faraday cages and rubber mats on the critical parts of the grid. We should have better armed security. We should have backup fuel. If a nuclear generator—a nuclear plant—goes down, there's—these very clear and simple solutions need to come in. So what does this have to do with Bob Hertzberg? When it graduated—and Bob is a very intellectual guy—just wasn't involved in the kind of think-tank component of this. But when it graduated from the think-tank idea to, like, what do we actually do? It was time to pass a damn bill.

Jess Mah: Yeah. What—is he the person to know?

Henry Elkus: Exactly. And so we went—and I hope he's okay with me saying this—we went and we—

Jess Mah: I'm sure he would be. I mean, he loves—yeah.

Henry Elkus: Went to his house and, you know, he was—had his stogies, and we were—we were in his tiki bar at his house, and we just sat there and we said, this is, like, a deeply important issue. It's not getting enough attention, and it's a bipartisan issue. This would be a win. Let's go do this. And we actually did it. The bills were passed in California. We did a summit in—it was a classified and unclassified summit that we worked with other members during the Trump administration that we did in Virginia that actually led to us working very deeply on an executive order that was signed during the Trump administration, another one that we worked on during the Biden administration. Now we're doing this project internationally as well. And so this really turned into something truly operational. But going back to someone like Bob is—I didn't say, Bob, come to my conference. I said, Bob, let's go pass a bill—like, this is what you do.

Jess Mah: And he's genuinely motivated to do good, I think—like, based on what I know about him, he basically teed up a lot of this stuff for him because he's got so much on his plate. Is that part of the value here?

Henry Elkus: I think it's—I think it's definitely part of the value. And he also goes back to—again, because—because I'm not a billionaire tech CEO who made his money and then wants to do a thing—I would imagine you can ask Bob, but if you're somebody like Bob and somebody like that comes to you, there's an agenda. We—we had the distinction of literally just being, like, 22-year-old kids.

Jess Mah: Yeah.

Henry Elkus: Me and Sam Feinberg, my partner—we were just sitting there on the couch.

Jess Mah: Going—Sam's very impressive as well. I have so much respect for Sam.

Henry Elkus: He's amazing. And we're just sitting on his couch and going, like, we really want to do this. We don't want to do this because, like, we'll make money from it. We don't want to do this because we have a political agenda. We don't even know whether this is a Republican or Democratic solution. We just really want to do it. And that, I think, is a very pure motivating factor to do stuff. And we continue to have that. I mean, our ego gets aggrandized and benefited from the actual success of the project—not it's a Democratic or Republican solution. That's a very unique, I think, advantage to have in an organization.

Jess Mah: So then if someone asked, are you a Democrat or Republican, would you answer at all? Or would you say you're an independent, or you don't even identify with that?

Henry Elkus: I think there's—well, I think there's two parts of this. The first is, what is Helena's political affiliation? Which is none. And we will never, I think, have a political affiliation if you define it by, like, a party plank that we subscribe to—correct. Then there's, what is mine? A, that's private. But I think B, what I will say about it is, we're in a political situation now in which I feel like there's a duopoly. It's, like, there's two corporations, and there should be more competition, and you don't really get the best from either side. And so, I mean, we have—I think part of, again, why we're dedicating our lives to do Helena is because in past generations, we would probably want to go into politics to get things done. There's a whole rabbit hole we can go down of why politics is not the most effective way to get things done today. But I think it goes back to—my political belief is just, unfortunately, getting things done is happening more in the private sector than it is in the public sector, at least through elected officials—a very important role that that has to play. But I've been very terrified of losing a lot of my time and energy getting into this kind of cul-de-sac of running for office—or doing things like that—so you—

Jess Mah: Don't think you'll ever run for office—you'll play a supporting role from Helena?

Henry Elkus: Or—it is a very simple optimization function for me of, I want to dedicate the rest of my life to building an enduring platform that can actually, in a non-BS way, address societal problems. And I will probably fail. But if I can get even 1% of the way there, it's meaningful. And if somebody presents me with a way that is better than the private sector to do it, I would—I would not say out of hand, no, I won't do it, but it would have to—it would—it would—I think the unfortunate reality is, we're in the most—we've done nonprofit projects, like America in One Room, for example, to address—to try to address part of this. But we are in a very inefficient legislative environment, and so getting things done through the pen is very challenging.

Noah Berkson: We want to hear about America in One Room. But I'm curious also, have you had situations happen where it would have been beneficial to be partisan, and you would have been able to get more support or get things done had you not been part of a bipartisan organization and not had a political affiliation?

Henry Elkus: No. I mean, not yet. Take the SHIELD project—this is really interesting. We didn't raise that much money for this project, and—I mean, by the way, Sam ran this project, so he should get all the credit—I should get 0% of the credit. But when you looked at the organizations that were trying to solve the electrical grid problem, it was really funny. There were Republican partisan organizations, but they were completely ostracized from getting bipartisan solutions passed because they were—the Democrats hated them. And the Democrats looked at the Republicans and said, these are fearmongering people that think that North Korea is going to implode an EMP over Kansas, and that that's the biggest issue, and that's not the biggest issue. Then there were the left organizations that said that we want to solve the grid problem, and the Republicans looked at them and they said, look at these idiots who are just trying to put microgrids in California—it's too expensive, it'll never work. And there's actually some good arguments on both sides as to why those were the wrong approaches. If we had come out and been partisan, we would have gotten actually sucked into that sphere. And this is not something that I can say details on, but I will say that in this project, we actually kind of acqui-hired nonprofit organizations that were on both sides of the aisle into our project. But part of the capital we raised was to actually acqui-hire and bring in great people that—and kind of subgroups and organizations that had the technical expertise and the legislative expertise to get this done but were ineffective because they were partisan. And so that's actually something we're very proud of, is, like, you can criticize us in a lot of ways that are probably merited—we are not a partisan organization. And I think we can prove that without really having to argue it—because if you just look at the projects we've done, it's kind of confusing what political affiliation we are because we're not one.

Noah Berkson: Do you think there's a lot of projects out there that could be very world-changing that are stuck in that kind of rut where it's just run by a partisan organization, and so they are never going to get the support of the other side?

Henry Elkus: Yes. The way that I would reframe that, though—and this is such an interesting topic, and I don't want to waste the whole podcast on it—but there are some no-brainer solutions. Like, we have a project that replaces plastic with a sustainable alternative and replaces Styrofoam with a sustainable alternative, and it works price-wise, and we think it'll get to scale—it'll be a great business. People are not going to stop you on the street and go, I really disagree with this idea that we should replace plastics, right? So there are some projects like that. I think the best answer to your question is, there's a lot of things that are such nasty problems that people are suffering from that need to be addressed, but the solutions are very controversial, and they've become politicized. And there's a—there's a big organizational question that we have—and anybody has—which is, do you get involved in those projects even though they're messy and you can get tarred by them? And I want to do those projects because I think there's nothing—you have to—it's a brave—you have to be brave and do those things, and you can be hidden in certain ways. So I think the best answer to your question is, there's a lot of those—we can get into some of my favorites—but there's a lot of those.

Jess Mah: But then would you worry about how your members would feel, and then their loyalty to Helena would be compromised, and then they wouldn't provide support for your other projects if you took that risk? And how do you evaluate that?

Henry Elkus: I mean, that is a—just to be honest, anybody has that concern. I think the question is, how do you mitigate it through your structure? So the way that our membership and that our organization is set up is, the members—we don't tell the members what to do, they don't tell us what to do. We don't owe them anything contractually for them to be part of the organization—they don't owe us that. They can come and leave. And my hope for the membership and the network and just anybody that is involved in Helena is that—and I'm not comparing us to Congress in any way, but I just think it's an interesting example—is, if somebody says something in Congress that you disagree with, you don't leave Congress—you stay in it, and you advocate for that position. And at its best, you have a nuanced and respectful debate about it. And if you feel like the project is so abhorrent that you don't want to be involved in any organization that's part of it, then I understand you would want to leave. Our job is to come up with the best possible first-principles defense of why we're doing every project. And if there's a member that says, I just fundamentally disagree with that, and I don't want to be a part of it, then I would respect them to say that—it hasn't happened yet, but I would respect that decision. That's the best thing we can do. Now, what's interesting, though, is there's a lot of organizations—and this—goes back to starting the organization, starting Helena—where they don't have that structure because their version of members is, well, you have to give us a million dollars a year to be part of the organization. Well, now they have huge leverage over you—what if you do something they don't like? Well, the million dollars goes away.

Jess Mah: Just to be clear, your members don't—

Henry Elkus: There's no membership fee.

Jess Mah: —have to pay a fee. Some will donate, some will invest in the fund, and some will just contribute their—their connections and, you know, intelligence.

Henry Elkus: And it's—and it's structured to be completely on a case-by-case basis. So it's—if we have a project and we think that you could like it, we'll present it to you, and if you decide to donate to it, great—but you're not obligated to. If there's a business that we're doing, and we think you'd be a great investor, we'll pitch it to you. Of course, you could say—and it's true—that's going to create leverage, and it's going to create that relationship. And we're never going to mitigate that. But it is, I think, a substantially better or more pure model than making a de facto commitment where there's leverage right away. And I also like that to myself because I think it's a feedback mechanism of, if we start doing work that we have not defended—maybe it's controversial, and we defend it, and we have just our hearts on the line, and we say, look, we really are doing this for this reason—that's one thing. But if we do something, and we really can't defend it on a first-principles basis that it's the right thing to do, that's a good feedback mechanism of, hey, without—it's not that we're incentivized to say this—we don't like you doing this. I think that's good feedback.

Noah Berkson: What are some examples of projects that you haven't taken on or wouldn't take on because they would be too controversial and be too partisan or political?

Henry Elkus: You know, I would hope that—and it goes to Jess's question, which is—I want to get to the scale of organization—I mean, everybody says this—but I want to get to the scale where there isn't an area that we de facto say we will never look at this area because we're scared of it. I never want to do that. Yeah, I do think there's honest questions about which areas to go into as we grow the organization. We're not a huge multinational corporation that has infinite money—we're not—we don't have a $100 billion endowment—we don't have all that yet. I mean, hopefully, we get to that scale—I mean, it'll be a 50-, 60-year thing, and maybe we'll never get there. I'll give you just one example of something that I just find so intellectually interesting—maybe we'll do something in this area, maybe we won't—but it's a great example of an area that people are, I think, deeply misunderstanding and is very controversial but has to be done. So I'll just set the stage, which is, as a species and as a civilization, we've decided that we're going to switch to electrify the world. We've also decided that we're going to do AI at unprecedented scale. And we're also, on a militaristic basis, arming ourselves to the teeth. I'm not going to provide a moral judgment of any of those three things—it is a reality that that's happening. To do that, we need metals—we need cobalt, we need neodymium for magnets—we just need metals. The supply-demand curve is already screwed up on this, and if you look at the next 10, 20, 30 years, it's going to get exponentially worse. How do we get metals now? In very unsustainable ways—often. If you look at the history of the Central African Republic, you look at Indonesian rainforests—mining has historically not been the most environmentally friendly thing to do. So where am I going with this? It turns out that there's an area on the ocean floor—it's one of the most arid regions in the world—called the Clarion-Clipperton Zone, and something we've been looking at for a long time, and it's been all over the news. And on the bottom of the seabed are trillions of individual nodules—golf-ball-sized rocks—that over millions and millions of years, pure metal—cobalt, you know, et cetera, et cetera—has formed around it. And it's sitting there, and it is in an incredibly arid part of the world. There are organisms there, there is wildlife there—it's not underground, though. So there's plans, and there's essentially an economic cold war happening between countries like the US and China on who has the rights to take a ship, throw a robot off the ship, and pick it up off the ground. And there's American companies and Western companies that want to do this—there's Chinese companies—there's—and I'm going to try to steelman the arguments—but there's environmental groups that make arguments, and I can see where they're coming from—is, we should not touch the ocean, we should not do ocean mining—you could debate whether it's mining or not—but we should not do it—it will kill species, there are unknown effects. What I think that's missing, though, is, okay, how else are we going to address climate change? How else are we going to electrify the world? Because what if we run out of the metals to do it? But there's also an argument that if we do ocean mining—or picking up on the ocean floor—we will just continue to do land mining. And so it's a very controversial problem. But this is an area that I would hope we don't shy away from being involved in and to actually really do a nuanced thing—a nuanced analysis of—we should have member meetings about this—we should actually do the diligence—we should see whether there's projects—if there's businesses or nonprofits or whatever—to get involved here. This is an area I feel really passionate about because it's, like, an Achilles' heel—by the way, China dominates it—China dominates 90% of metals refining—so there's a whole geopolitical narrative here. That's one example of a giant rabbit hole you could go down—there's, like, 100 of these. So the question is, if you're running an organization to solve societal problems, do you get involved in those or not? And there's a lot of people that just would hear something like this and go, oh, that's going to piss off my donors, or that's going to piss off my constituency. And what we're trying to build at Helena is an organization where we can have that debate, and it's not controversial, and we'll see if we can pull it off. All we can, I think, do, as leaders of the organization, is come at it with very pure intentions and a pure heart of, we're doing this for the right reason—and check us—check our math, check our analysis.

Jess Mah: Wow, that's really cool that you approach it that way. I guess if you have all of these problems collected on a spreadsheet—let's say hundreds of problems you could solve—how do you decide what to rank-order, and how many can you actually handle at any given time? Because just this alone could be a full-time job for 100 people. So how do you manage it yourself?

Henry Elkus: Well, I don't manage it myself—I have an amazing team. We have amazing investors that help us all the time—we have amazing donors, we have amazing board members. Besides the membership, there's really thousands of people that we've kind of put in our network and worked with—so that's number one. Number two, there is no way—there are people that will show you a quantitative checklist and say, this is my impact metric—and it makes me want to pull my hair out because there exist qualitative realities in the world—it's, like, you can't rank what is a more important project than others. If you just say, well, okay, it's only about the metric tons of CO2 I'm going to prevent from coming into the atmosphere, then you can only compare it to other projects that have that metric system—and that is not a way to do it—so you can't do it. So then the question is, how do we choose, and how do we rank?

Jess Mah: Or at least you have, like, a top 50 or top 100, and they're not ranked per se—it doesn't work that way.

Henry Elkus: It doesn't—because I hope to get to the point where we can think about it not in terms of our capacity and bandwidth to execute and our capital and our assets—but right now we have to do it that way, and I suspect it will never be like that. And so we really look at, is—does this project have an impact that is really meaningful at a really global scale—but most importantly, can we do it? Like, is it going to actually work? And is it going to work during a timeline that is meaningful? And that is really the determining factor the more we've gotten into this. Now, if you had asked me, like, seven or eight years ago, I would have probably given you a very flowery intellectual answer—but the more experience you actually get being in the field and doing this, you realize how hard execution is and why so many people fail at it.

Jess Mah: Would you be open to sharing what are the top projects you're pursuing at this moment?

Henry Elkus: Sure. One endeavor we are really deep in is psychedelics—and specifically the use of psychedelics for addressing critical mental health issues. We have spent the last year and a half plus just on an odyssey to try to study and then, you know, work with the FDA to get approved and then roll out MDMA-assisted therapy. That has not gone as well as we would have liked to—we're still kind of really heads-down in doing that. We're very optimistic that—and I think a lot of people are—that this will get approved. There's a long kind of road with a lot of complexity in getting that done—but it's something I feel extremely passionate about.

Jess Mah: How did you get passionate about that? How did you identify this specific problem in the first place?

Henry Elkus: So, I mean, mental health has been something that Helena has been involved in a long, long time. I mean, one area we've been involved in very deeply is in social media reform, actually—with members like Tristan Harris, Aza Raskin—who's not a member, but he should be a member—he's amazing—Daniel Schmachtenberger—and I don't take any credit for the work they've done—we've supported them as much as we can, and I really love that. And they've studied kind of the effects of social media on the human brain and young people—suicidality—all of that. On the other side, we've looked at issues like PTSD—where PTSD has an unfortunate lack of approved ways to address it. And just looking at the data of the amount of people that have done MDMA-assisted therapy in its various forms that have lost their PTSD diagnosis when they were very close to suicide or there was no other option—and then looking at the toll, especially in the military community that the VA, for example, has—that was something that was a known entity to us. And we kind of then got acquainted with the idea that we could actually do a project in it through an investment. And so we did that investment, and we're still working very heavily on that.

Noah Berkson: And you did clinical trials for this—the results were very good.

Henry Elkus: Yes.

Noah Berkson: You expected to get approved, and you were rejected.

Jess Mah: What happened—very publicly too, everywhere.

Henry Elkus: We didn't do the trials—I mean, I don't want to take any credit, good or bad—I mean, these were amazing people that have worked on this far before we got involved. We invested as the lead investor in Lykos, which was formerly MAPS Public Benefit Corporation. But yes, they did do phase three and phase three confirmatory study—if I have the numbers correct in my head—71%, I think, of—of the trial participants lost their PTSD diagnosis. The numbers were incredible.

Jess Mah: After three sessions.

Henry Elkus: After three sessions. And we deeply believe in it. There was a lot of politics involved in this, guys—I mean, it's—it—there was—if you look at the—what happened with the FDA AdCom, which I won't really be able to get into—

Jess Mah: Yeah.

Henry Elkus: But it was not rejected—the FDA—and we're still in dialogue with them—has essentially requested a further study—which is bad—I mean, it's very challenging for any company, especially a startup. And one of the reminders that you have to make is that in the pharmaceutical industry, startups have a very tough job—there's very few successful startups in the pharmaceutical industry because of how expensive it is to take a drug through, you know, phase one, phase two, phase three, phase three confirmatory—to go through the new drug—the NDA—et cetera, et cetera. So there's a big kind of question of how—what the path forward is to do an additional phase three study that fits—fits all the metrics necessary. I remain very optimistic this will happen—I think it is an inevitability that psychedelics—the correct use of regulated psychedelics in the right way, with compassion, with the right modalities—I have to put all those things on it—this will be a critical solution set for mental health. Beyond that, there's incredible benefits that we can explore. There's also other projects in the psychedelic space we're getting involved in—one of them is an ibogaine, which I can talk a little bit about—which is massive for traumatic brain injury, for opioid addiction. But that's one area that we're very, very involved in and are working hard at.

Noah Berkson: How detrimental would that be to pharmaceutical companies that—that sell SSRIs, for instance—if MDMA-assisted therapy were to become a big player in that space?

Henry Elkus: Look, I think that when they're—I'll say this—when there's a new modality of care that you don't need to be on the rest of your life—we're all in business—we know what ARR is—ARR is really great—annualized recurring revenue is really great—

The power of bringing together diverse groups is something I explore in my piece on Outcove.

Jess Mah: Whereas here it's just, like, three sessions, and then you're done.

Henry Elkus: So yes—now, how beautiful—what I will also say—what I will also say is that take esketamine—so this is the first—people debate whether esketamine is a psychedelic or not—but it was certainly one of the first kind of quasi-psychedelics to—to come onto the main stage—is the first FDA approval in the space—it is a nasal ketamine spray for depression. And Janssen—which is a subsidiary of Johnson & Johnson—put this through. And Lykos actually just hired as their chief medical officer the guy that oversaw that—he's an amazing guy—we've spent a lot of time with him. This is actually one of the most profitable drugs for J&J right now. And it was actually—if I recall correctly—it was not a sure thing that they were going to support this and do—it was a big debate—they did it—and I think it's actually one of the best year-over-year revenue recurring drugs that they have. So my belief is that the big pharma companies will get involved in this—but there's a whole debate, and I think the right—you have to apply the right nuance about how do you roll out psychedelics? And there's all these tangential issues—there's a therapy component that has to be kind of put in—I think there's a tremendous amount of good that the pharmaceutical industry does, but there's a tremendous amount of bad—and that has to be factored in—it's a really nuanced—it's kind of a very nuanced project—I mean, it's hard.

Jess Mah: Like, kudos for working on it.

Henry Elkus: First of all, we have to be humble and say, like, we're not the ones that are suffering from this, and that wouldn't—but it's—when you start to meet people that so desperately want to bring this to the world—and people that have had their—I mean, it's not an exaggeration to say that they really feel that their lives have been saved by this—you develop a very special kind of connection to this project, and you really want to get it over the line—but you also need to do it right, and you need to do it—and it's a—it's a big challenge, and it is the most emotional project we've ever done. And it was so—I mean, it was just ups and downs—I mean, I was just telling you before the podcast—there was this—you know, I was—I had food poisoning in Brazil, and I was in a hotel room watching the FDA advisory committee talk about—so brutal—and I mean—but, you know, it was just watching and just going, oh, like, this—this sucks—like, this really sucks—and—and that every side—and I trust that every side of this debate wants what is best for patients and will just have to work in the most good-faith way to get this over the line. And I think we have to listen to every critique, and we have to incorporate that—there's no easy way here—so that's—that's one—I wish this—

Jess Mah: Was available years ago—I talked to Rick Doblin—who's a founder of the MAPS project—about a week after my last boyfriend died—he served as a Marine, frontline combat in Iraq, and committed suicide.

Henry Elkus: I'm sorry, Jess.

Jess Mah: Thank you. And, you know, I found out about this—got to this obviously a little too late—but I really believe in that work—so it's cool that you're working on it.

Henry Elkus: I mean, we're not giving up—I mean, please don't—yeah—and there's a lot of amazing people—I mean—so that's one—I mean, I'll give you another one that we just announced today that we're really excited by—it was completely different—it shows you the diversity of the project—but we became the lead investor in a company called Matter—which is going to be the first mass-market electric motorcycle in India. And why this? Well, there hasn't really been a kind of Tesla-type story in India—one of the main reasons is that in India, you travel on two wheels primarily rather than four. And so there's been electrified rickshaws and scooters—but there hasn't really been that motorcycle—and it is also going to be the first kind of startup OEM in India—they're really producing the motorcycle in India.

Jess Mah: And the founders are based in India—they understand—

Henry Elkus: Yes—my team is actually in India right now—the deal team that's leading this is in India right now at the factory—they're launching in a couple of weeks and actually delivering the bikes—they sold out all 40,000 pretty quickly—in the launch video—it's amazing—we're really psyched about that—so that's another one we're working very deeply on.

Jess Mah: Did you identify the problem and search for a company, or did they pitch you, and you're, like, wow, this is actually right in line with what we'd want to—

Henry Elkus: In this particular case, we absolutely will not take credit—I mean, there's a—I mean, there's a great thesis about the growth of the Indian economy—there's a great thesis about—I think the fact that electrification probably will happen—but we did not think about that from a first principle—we saw the company, and on the investing side—what I will say is, oftentimes, we get a lot of great deal flow of great opportunities that come in, and it's very hard to kind of—we do have areas that we look at—but it's really about the team—we're very concentrated in our investing—so we'll do 10- to $30-million checks to take large portions of a company, and we'll do Series A–type investing—so we're not doing that many projects at a time. And so we'll spend a lot of time with the team—we'll really go into DD and try to help the company as much as humanly possible. And so it's hard to kind of pre-select—we're only going to do stuff in that space—we want to be very kind of wide-open with which teams we're going to work with.

Jess Mah: And how many deals will you do per year? Or you don't think about it that way?

Henry Elkus: And I would like to not think about the question—I mean, it's—it's—no, it's—it's capital-constrained—so, you know, we—we—you know, we—before we had a fund, we had to do what are called SPVs, in which you find a deal, you raise money from investors, and then you try to do it at the same time while the deal is still there—which is really challenging—we did a lot of those—then we raised a fund—first one was $105 million—and there's a certain amount of work that you can do with that money—so right now, it's about two or three a year—my hope is that next year we do a lot more, and we grow our capital base.

Jess Mah: Yeah.

Noah Berkson: You talked about reading as something that is a very big part of your life but was also really transformative to you.

Henry Elkus: Yeah.

Noah Berkson: Where did that come from? You mentioned as a kid not feeling like an intellectual—where did that change?

Henry Elkus: Great question—so I—yeah—

Jess Mah: And 100 bucks a year? That's insane—it's, like, two bucks a week.

Henry Elkus: I love reading—I mean, reading has completely and fundamentally changed my life—I love talking about it, too, because I feel like it's, like, you can take the best ideas that humans have ever come up with and then put them into your brain and then make decisions with that knowledge—and it's, like, why people don't spend their lives just doing that—there's a great—I'm going to completely mispronounce it—but there's this—this, I think, Aristotelian term called phronesis—I know I'm mispronouncing it—but it's—if I best understand it—it's the act of spending about half of your life just intaking information, and then the other half just being an idiot in the field and actually trying to use that information—and that if you can actually spend those two kind of 50-50 slivers well for the rest of your life—it's, like, the most complete way to live—and I think it's—

Jess Mah: Do you actually operate like that where you'll block off half the day for information consumption and half for operations?

Henry Elkus: I try—but I'm addicted to social media just like everybody else is—I have all of these issues just like everybody else does—so I'm not a superhuman in any way—but I'll tell the story about reading—so I have to admit—just to be honest—is that when I was in high school and college, I did not read—I never sat down and was, like, I'm gonna read a book front to back—I just never did—I would just—I would just not do it—and I kind of BSed a lot of—of—BS is the wrong term—I mean, I really did care about the courses and the education I was getting—I deeply cared about it—but I just never committed myself to reading—and it was an attention span thing—all that—I then started Helena and actually started to get members into the organization—and I'll never forget this—I went to Burning Man—I mean, I went to Burning Man, and I went with a friend of mine, and we had an amazing, kind of crazy time—we—we kind of were driving home, and he's very close with me, and his dad is a history professor—I respect him to death—David Nielsen is his dad—and I was on the phone with his dad and talking to my friend Thomas, and Thomas kind of turned to me, and he basically said, look, dude, you have, like, a couple people that have now joined this thing you're doing, and one of them is a Nobel Prize winner—the other guy's a four-star general—you don't read—if you think that you're going to actually sit with these people and then have a—a high-level conversation that could turn into something, and you haven't respected them and respected yourself by actually spending years, like, focusing on what do they do—like, at a deep level that isn't cursory—you can't just regurgitate a Wikipedia page—then you're never going to succeed—like, what you're doing is never going to actually turn into anything besides, like, a cute little networking group—and you probably won't even pull that off because you won't have good conversations with them—and my ego, of course, responded very negatively to that—and the way that I responded to it was, well, I'll just—I'll just do it—like, you know—and—and his—his dad was a Great Books professor—so there's these amazing programs in college where you read a preset—and it was a St. John's Great Books professor—I understand correctly—and so I just actually printed out the St. John's kind of curriculum—I didn't read the entire thing—but I just started churning out the books and then five—five or six of those books, and I was completely hooked—and there's this magic to sitting down with no phone—your phone's in another room, and it's just the physical book, and just you get through a—like, book about human history or about civilizational history or big history or a book about physics or chemistry, and it's—it's just completely hooked me—and I started to just read because I loved it—not because it was this kind of weaponized operational thing that would be good for business or good for my company—and I have an Instagram where I post all the books—I'm a complete book nerd—and I just can't speak enough about the benefit it has provided me—and it's not that I can, like, be cool at parties—or be cool at very nerdy parties—it's more that when I'm thinking about a project or thinking about making a decision, you can—you can actually recall the other human beings that had been through similar experiences and what their results were—and it's an incredibly profound thing to go through—I don't know—I mean, I can talk about it for hours.

Noah Berkson: Are there any books that were very transformative to you or—

Henry Elkus: Yeah—I'm asked this question all the time—so I'll give you, like, the—there's so many—but I'll give you a couple that are not necessarily, like, a hierarchy—but just are just amazing—and I apologize because some of them are book series—there's a book series called The Story of Civilization by Will and Ariel Durant—which is a husband-and-wife team that I believe spent 50 years doing this—and I think there's, like, eight or nine—or maybe nine or 10—10 of them—each of them is over a thousand pages—and it's just hardcore civilizational history—and it's not bibliographic, meaning—it's not, like, this happened, and this happened, and this happened—these people traveled to Egypt and then said, we're really going to do Egyptian history—and they write prose about what happened over a thousand-year period—what the art was like, what people were like—that makes you cry—like, I've cried reading—and it's—so there's an entire set—and if all you do is just read these the rest of your life—even though they're very—I would—and if you want to cheat—they wrote a summary at the end—I think at the end of it—called The Lessons of History—which is, like, 150 pages that is just breathtaking—and so if you just read that—you get a sense of, like, what has happened—and it's extremely biased—it's Western—it's, like, white people writing about Western—you can attack it from every angle—I understand—but it's—it's unbelievable—so that's one—there's a—another book series about Lyndon Johnson—LBJ—written by Robert Caro—and it is, to me, the greatest biography writing in history—I won't go into a rabbit hole on that—but I would read those—that changes your life because you can see somebody go from extreme poverty—Johnson City, Texas—to being the most powerful person in the world—and exactly what was done in this extraordinarily Machiavellian way—and it helps you understand ego and human nature—so that's another one—a third one that I always recommend is called Finite and Infinite Games—and I believe it's written by somebody named James P. Carse—it's an amazing book, and it's so simple, and it stuck out to me as just extraordinarily helpful—and so I'll just explain it really quickly—if me and you are playing chess—it's a finite game—I either beat you, or we draw, or I lose—if you're in a marriage—you don't win a marriage—if you're in a nuclear war—you don't win the nuclear war—right?—so a game of chess is a finite game—but a marriage or a relationship is an infinite game—in an infinite game—the object of the game is not to win or lose—it's actually to perpetuate the game—to keep the game going—so, like, nuclear politics—the goal is to not end the world or to win—nuclear politics is to not have a nuclear war—so you don't want to beat China in nuclear war—you don't want to participate with China in nuclear war—you want to work with China to perpetuate the game of human civilization—you don't want to win a marriage—you want to continue the marriage—so it's healthy in a relationship—right—so what the book does—in this extraordinarily eloquent and kind of shocking way that makes you realize the mistakes you're making in your life—is it tells you how to understand whether you're playing a finite or an infinite game—and you really want to play infinite games—you don't want to play finite games—and this goes back to the point on people using capitalism to create mental models of beating the finite game of capitalism to then play the infinite game of philanthropy—which is very different—so that was—I could go on for another hour—but those—those are three kind of cheater—because two of them are series—but those are three really great ones.

Noah Berkson: Could you tell us a bit about America in One Room? I know that we—we glazed over it.

Henry Elkus: It's an amazing project—it's one of the most meaningful things we've done, and I want to do it for a long time—I'll try to explain it really simply—there is a poll that was done, and they asked people about what they thought of the 1965 Civic Affairs Act—and they asked, like, a million people—and people had very strong opinions—I hate this—or I really like it—or I really don't like this—and there is no 1965 Civic Affairs Act—and so it tells you a little bit about polling—and another issue is polarization in America—which I don't need to summarize—there's an incredible team at Stanford led by Jim Fishkin and Larry Diamond—who are both Helena members—that do something called deliberative polling or deliberative democracy—it is a scientific process of selecting a group of people that is representative of a country or of a larger populace—and they've been doing this for 30 years before we got involved in any way—we worked with them and took that and did a project called America in One Room—this was in 2019—we got 535 people that were as accurate a representation of the US voting electorate as possible—and we had a control group that was similar size—we raised the money and then bought out the Gaylord Texan Hotel in Texas—we're the largest hotel in Texas—we kicked everybody out of the hotel, and we flew the 535 people—like, we flew America to one room—before they arrived—we polled them on what they thought of the—what their political views were in the 2020—heading up to the 2020 general election—what do you think about immigration?—what do you think about this?—very detailed polls before they arrived—so we got the starting value—which looked very much like what a Pew poll or a regular poll would say—they then spent three magical days together—which I don't have enough time to explain in detail—but they debated for nine hours a day—and then they talked to the presidential candidates and other experts at night—and then they did it again—and then they did it again—and if you just google America in One Room—an incredibly transformational thing occurred in which instead of fighting each other—instead of disagreeing—they all converged, and the extremes actually fell away—people converged to the center, and up to 50% changes in opinion occurred on these issues—because we had a poll at the very end when they left—the New York Times put it on the cover—Obama endorsed it—it was this amazing project—we've now turned into multiple other efforts—which I can talk about—what's interesting is people go—okay—that was cute—you did this once—and it was in a vacuum—it's true—we have to scale it—there's a lot of ways we can do that—but the other critique that we get is, it's not sticky—it's, like—okay—you took these people—they had this amazing experience—but then they go back to their hometowns, and they're just going to revert back to their opinion—the New York Times actually surprised us by revisiting a year at the year anniversary—and they went back to the 535 people, and they repolled them—and they—and they did another study—and we did not—we're not involved in the study—and they showed that it was sticky—and so we deeply believe that this is actually a social technology—ironically—if you remove social media—you remove tech from this—that you can actually have a way to organize human beings in a more democratic process that makes democracy not just work—but shine and scale and be very, very effective—and so this is an effort that we've now turned into multiple different projects—we just did one a couple months ago that just came in—it's got a lot of coverage—it's on Good Morning America and NBC Nightly News—on first-time voters—it was the first time ever that people that were voting for the first time—we did a representative sample—and the next one we're going to do is on AI—it'll be on AI policy, and I'm very excited for it—we'll get a representative sample of the United States in one room, and we're just going to focus on the critical decisions that need to be made about regulating or understanding or making decisions based upon this thing that we're dealing with—AI—and that'll be a massive effort, and I hope we pull it off—but that'll be the next one.

Jess Mah: Wow.

Noah Berkson: Henry, you are an extremely interesting person—I think we could sit and listen to you talk about this all day—where can people find you?

Henry Elkus: Helena.org—you can see all the projects—you can email me—henry@helena.org—I would also go to Instagram—LKUSLIST—that's a way you can engage me—that's where I post the books—and one of my favorite communities that's been built is this book Instagram—because people will—unbelievable—people will just message me and say—hey—have you read this?—and it's a great way actually to engage with me and talk to me on an intellectual level—so I love when people reach out that way as well.

Jess Mah: Final question I have for you is the question you ask Helena members when you onboard them—what else do you need help with—aside from obviously infinite capital resources—what else are you spending so much of your time on that you would really like more assistance with that your members are, for whatever reason, unable to fully assist you with at this moment?

Henry Elkus: Besides capital?

Jess Mah: Besides capital—I'll help you with that—by the way—I have an IR team, and we work with a lot of ultra-high-net-worth—so I'll deploy that for you.

Henry Elkus: But yeah—I think—

Jess Mah: How else?

Henry Elkus: Really simple—which is the—when I look at the really—the big successes we've had—it's been because there was somebody special on our team that—like, we didn't talk about one project we're doing—it's in biosecurity—it's in the intersection of AI and biosecurity—and we have someone on our team named Evan—for example—just shout him out—that is just unbelievable—and if you ask Sam—my business partner—this project would not be where it is—not without Sam and without Evan—and so if there's somebody that really connects with this, and you really feel like it would be great to work with us—I think that's one area—and we have a small team—I try to hire as few people as humanly possible for a lot of reasons—but really exceptional people that really, deeply care about this—and the type of person that we like is often to say somebody who is in the Goldman Sachs position but is really miserable—somebody who's, like, a killer—like, they're very good—they're great at finance—or they're great at VC—or they're in the nonprofit world, and they can execute, and they've done very well—but they want something that's more meaningful—and they wake up in the morning—and the asset that they don't have—to answer your question—is, like, happiness and, like, contentment—and I think our job is extraordinarily hard at Helena—but we—we sleep really well at night because I think the projects we're doing are very interesting—and so there's a lot of people that are attracted to that—and if you—if you're one of those people—then to reach out to us would be great.

Jess Mah: Amazing—awesome—thank you.

Noah Berkson: Thanks again.

Jess Mah: This is such a good pod.

Here are some topics that we talked about:

• Money and Success Mindset - Suli discusses his relationship with wealth as an immigrant's child, calling it "toxic" at times. He explains his evolution from hoarding wealth to using it to enhance life experiences, influenced by reading "Die With Zero" and joining Tiger 21 (a group for wealthy individuals). He shares how his perspective changed from focusing solely on "creating shareholder value" to finding meaning and helping others become successful.
• Status and Identity - We explore how status symbols change with context (angel investing in Silicon Valley versus luxury goods elsewhere). Suli reflects on his embarrassment about working at his family's gas station as a teenager, yet acknowledges how that experience built his work ethic and business skills. He discusses how success creates optionality, particularly in dating and relationships.
• Family and Legacy - Suli shares insights about his immigrant family's journey, working with his brother, and concerns about wealth's impact on future generations. There's significant discussion about the challenges wealthy people face with their children, with Suli noting that Tiger 21 members worry about their privileged children "starting on third base" but potentially moving backward. The podcast also covers Suli's changing life priorities as he enters his 40s, shifting from career focus to desiring family and meaningful impact.
• And many more!

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Full Transcript

Suli Ali: I probably feel like a failure 75% of the time and success only 25% of the time. As you have business success, you become more desirable, and that gives you a lot more optionality, gives you more time to be able to wait before committing, and gives you more of a shelf life to be able to date younger people even as you get older. I worked at a gas station in high school, and it was just something that I was so embarrassed about. Like, I didn't want anyone that I went to school with to know that, oh yeah, every Saturday, I spent 12 hours working at a gas station. They had a hot dog eating contest where you didn't eat the hot dogs with your mouth.

Jess Mah: Awesome. Welcome to the pod.

Suli Ali: Thanks for having me. So excited.

Jess Mah: Yeah, tell everybody really quickly what makes you awesome from a business perspective. Just a quick bio in 30 seconds.

Suli Ali: I studied computer science in undergrad, worked at Microsoft for three and a half years, and have been an entrepreneur for the last 16 years. Started a company called TinyCo that made mobile games, raised a bunch of venture capital, sold it in 2016, and then somewhere along the way started investing. So, invested in 100 startups, 30 or 40 venture funds, about $60 or $70 million of real estate, and a bunch of private equity funds.

Noah Berkson: Or north of that; those numbers are adding up.

Jess Mah: North of 100. North of a billion, or you can't say?

Suli Ali: Not north of a billion.

Noah Berkson: You went to Burning Man. Was this your first time?

Suli Ali: Yep.

Noah Berkson: What was your experience?

Suli Ali: I thought it was amazing. I saw more boobs and penises than I needed to see. I saw so many that I never need to see boobs or penises ever again in my lifetime, and maybe five lifetimes' worth, which was actually kind of amazing. The thing I love about Burning Man is that, as a society, we don't restructure society at all. Like, San Francisco, Louisiana, New York—they're very different. San Francisco, you care about ambition and building things. New York, you care about money and finance. Louisiana, you care about having a great quality of life, sunshine, the outdoors, and maybe Hollywood, but they're like 95% the same. When you go to Burning Man, it's like someone has said, we're questioning all of society and doing something completely different. And that's the best part about it. I'm so surprised that we don't do that more. Donald Trump actually said this thing that I thought was cool, which is, "I want to take 0.1% of federal land, which is nothing, and build 10 new cities that are like models of the future." I think that's a dope idea. We just don't do stuff like that, weirdly, as a society. So, when you go to Burning Man, there's no money. People are trying to give more than they take. You're not wearing the same clothes that we're wearing here today. You're either half-naked or wearing stuff that you'd wear in a post-apocalyptic Mad Max place. You're making art. Art is what's of value, not status. Status doesn't come from money or looks or these other things. It comes from art and being weird. That's an awesome society. So yeah, I don't know why we don't do more societal experiments.

Noah Berkson: Is that kind of like what's going on outside of San Francisco, like that proposed new property?

Suli Ali: I doubt it. I think they're probably just like, "We're going to build a great business opportunity, buy land outside of San Francisco, and build a cool master-planned community." Maybe they do stuff like Waymos are everywhere, there are no cars outside of Waymos, and people use bicycles. But I think it's more of a financial endeavor than a societal one. They're not going to rebuild the way schools work. They're not going to rebuild the values of suburbs or the way that people rank status or money. Any of that stuff's all going to be the same.

Noah Berkson: So, maybe to just—

Suli Ali: By the way, one of the crazy things about Burning Man that I did not expect is when you enter, there are all these toll booths, and you pull up to a toll booth, and there are three people who are so excited to see you. They're jumping up and down with excitement that you've come to Burning Man, and they make you get out of your RV and talk to them, and then you hug them for like five minutes each or something like that, and they're completely butt-ass naked the whole time. Then they make you do snow angels in the sand. So, you immediately feel like, oh, whatever societal values I was used to five minutes ago, they're gone. I'm in a different world right now. That's great. Super dope.

Jess Mah: I love it.

Noah Berkson: Jess has hosted a Burning Man camp for how long now?

Jess Mah: Yeah, this is my eighth Burn.

Suli Ali: Nice. What's your favorite part about it?

Jess Mah: I love the community aspect and having a camp.

Suli Ali: Yep.

Jess Mah: I met so many great people there. I've dated a bunch of guys I met at the Burn. Got a lot of business value out of the Burn. I've hired people, raised money. And, of course, the art, the naked people, lots of psychedelics, and great stuff.

Suli Ali: There's stuff that you just see there that you would never see, and you cannot unsee. A good example is they have a hot dog eating contest where you don't eat the hot dogs with your mouth, and I don't know where they go, but the hot dogs just disappear. It's nuts.

Jess Mah: So, you shoved them up your ass?

Suli Ali: Put them everywhere else.

Noah Berkson: You can imagine every orifice.

Suli Ali: Yes. It's pretty nuts.

Noah Berkson: Did you participate?

Suli Ali: I walked in, and there was a woman lying on a table, butt-ass naked. Everyone was screaming her name. There were a hundred people just shouting her name: "Maddie! Maddie! Maddie!" Then the hot dogs came out, and I saw what they did with them, and I was like, I can't be here. I left immediately because this was beyond my threshold of things I can see.

Noah Berkson: Did this change the relationship between you and your girlfriend, experiencing this together?

Suli Ali: I think we're really good about, like, let's try new things as much as humanly possible. So, I don't think it changed our relationship, but it was a great time. One of the things—there are a lot of friends I have that are guys who have a really hard time committing to being in a relationship. Actually, my brother is one of them. A friend of mine once said to me, "I keep going on vacations with boyfriends that I'm dating, and I end up with kind of a new boyfriend every year or two. So, I can never talk to my current boyfriend about the last trip I went on because I went with a different boyfriend. He knows that, and he doesn't want to hear about that stuff." She was like, "I love having a partner where we have the same memories. So, I can talk about, oh yeah, five years ago when we went on that trip, this thing happened. What we're doing right now reminds me of that." I love having that with my girlfriend, where I know that eight years from now, when we've done our eighth Burn, we're going to be able to talk about the first Burn and what it was like.

Jess Mah: Your brother is also very successful. Do you think commitment challenges for men correlate with business success?

Suli Ali: I think there's a correlation, for sure. That's because as you have business success, you become more desirable, and that gives you a lot more optionality, gives you more time to be able to wait before committing, and gives you more of a shelf life to be able to date younger people even as you get older. But I think for a lot of people, they undervalue commitment and overvalue optionality.

Jess Mah: Because if you have a commitment challenge, then by definition, you haven't committed. So, you don't know the value of that and all the benefits that you're explaining. You're like, alright, well, optionality is all I know. So, there's some fear of the unknown as well, perhaps.

Suli Ali: Yeah. It's such a different thing that happens when you meet somebody and date them for the first time. There's this awesome period where you're getting to know them, and all of the jokes that they're telling you, all their stories, you've never heard them before, so it's awesome. Then after that, you go out on double dates with people, and they start the story with one word, and you know what the next three minutes is going to sound like because you've already heard that story. There's something in the human condition, or in modern society, that makes you think, oh, I don't want to hear that same story again. It's like going to a comedian and hearing the same jokes over and over. You're like, this is stale. I think that's one example where people are like, this is telling me I've been in this relationship too long. I need new experiences with a new person.

Jess Mah: How about money? Does the fear of having to do a prenup and split finances with a committed partner—this is from your brother's, your successful brother's perspective—is he worried about that? Is he also worried about women liking him just for his money? Was this a problem you had? What would be your advice for all the successful men and women out there listening to this?

Suli Ali: Yeah, that's a good question. There's a lot to it.

Jess Mah: Because women don't understand this phenomenon. I talk to my successful guy friends all the time about it, and they're always worried about the gold diggers. I just want to demystify that for everybody.

Suli Ali: My brother said this to one of our friends when he sold his business: "There's an island that's only for rich people, and I think I got my ticket. How do I get on there? Where is it? Tell me, let's go." You know, there is no such island, as far as I know. I don't think Necker Island is it. For a little while, I think he was stuck on Gold Digger Island. He found his way to Gold Digger Island and was just stuck there. Hot women who wouldn't have chased him in high school or college were now chasing him. So, I think he was like, I gotta experience this. I gotta see what this is like. He did a bunch of that. The weird thing he does—I can't believe I'm saying this—is he'll kind of fall in love with whoever he's dating and be like, this person is amazing. For example, he was dating this girl, and he was like, this is the most beautiful woman in the world. I was like, this girl is objectively not even close to that. I don't know what kind of rose-colored glasses you have on right now, but no, absolutely not. He does get really into it and wants to go deep with people. So, he was on Gold Digger Island, had a lot of fun, and now he's trying to find his way off of Gold Digger Island. I think he's going to be fine and do it.

Jess Mah: How about for you? Did you worry about this gold digger phenomenon?

Suli Ali: I thought it was so obvious when people were into that. For example, he dated this girl who was like, "Oh, you don't really like me." He's like, "No, I like you. What are you talking about?" She's like, "My last boyfriend used to pay for my Ubers. You don't do that." He's like, "Oh, your Ubers to see him and go back home?" She's like, "No, all my Ubers, wherever I want to go, with him, without him, wherever I'm going." That's just so obvious what you're saying there.

Noah Berkson: Did you succumb to any of this?

Suli Ali: I think not as much as he did. For whatever reason, I haven't been as into status things as he has been. For example, he was really focused for a little while on getting the Amex Black Card, and he got one. For a while, he would use it all the time. He gave me one because you can give a companion an Amex Black. Even though he gave me one, I've used it maybe five times in my life because I use my Bank of America credit card since it has better points than the Amex does. He was just more into that stuff for some reason than I was. I don't know why.

Noah Berkson: What's the biggest thing that you do for status now?

Suli Ali: That I do for status now? So many things. Where to start? I lived in San Francisco for a long time, and status there isn't about Rolexes, fancy cars, or that stuff. It's about angel investing. I spent probably 10 years angel investing, and at the end of it, I was like, am I just doing this for status? I think I was probably at least 50% doing it for status versus something else.

Jess Mah: Wow.

Noah Berkson: That might be the most expensive hobby for status to possibly do unless it returns.

Jess Mah: Well, yeah, it's a comparable hobby.

Suli Ali: Yeah, I think it's actually a great hobby because you learn, you have fun, and you invest in assets that generate more wealth.

Noah Berkson: Has that made you a lot of money?

Suli Ali: Yeah, I've made a bunch of money from angel investing.

Noah Berkson: How many companies have you invested in?

Suli Ali: I'm not sure, probably around 100. It's funny because I don't even know how much money I've invested in angel investing or what the returns are.

Jess Mah: You don't track it on a spreadsheet, batch it into proposed vintages, then benchmark yourself relative to—

Suli Ali: No, I don't do that. I probably should, actually. I met this guy; I joined this thing called Tiger 21.

Jess Mah: Yeah, I'm familiar.

Suli Ali: Yeah, it's like—

Jess Mah: You like Tiger 21?

Suli Ali: I love it.

Jess Mah: Really?

Suli Ali: It's like YPO for older people and, generally, you know, rich.

Jess Mah: Could you explain to people what Tiger 21 is?

Suli Ali: Yeah, Tiger 21 is a group where you pay $36,000 a year to join. You do 10 in-person meetings. There are local chapters with about 10 people in each chapter, so you meet with those 10 people all the time. You have to have a minimum net worth of, like, $30 million or something to get in.

Jess Mah: So, you're telling us you're worth at least $30 million?

Suli Ali: I lied and told them that I was worth at least $30 million. Yeah, that's what I can tell them. They think I'm worth $30 million.

Jess Mah: Perfect. Okay, so you're supposedly worth $30 million, you have $36,000 a year to spend, you go to all 10 meetings a year, and what do you get out of the meetings?

Suli Ali: What I love about it is that it's people who are older than me, so they're generally in their 50s or older. They have such a different perspective on life than I do. They're kind of past the money-making phase and are like, okay, what am I doing with my life to make it as high quality as possible, as interesting as possible? They're really worried about their own health and their kids. Ninety percent of what they care about is, are my kids doing okay?

Jess Mah: It's not even about money and investing. It's about how to manage your life in a holistic sense.

Suli Ali: Yeah.

Noah Berkson: Yeah.

Suli Ali: I thought it would be like, oh, cool, I'm going to find new investment opportunities and make more money by doing this. One of the things you do in it is what they call portfolio defense. Every time you meet, one person comes in and writes a bio about themselves that's, like, 20 pages long—their entire life story. Then they show you their entire net worth, where all their money is, what their annual expenses are, and what their annual income is.

Jess Mah: That sounds like a really good habit that everyone should do, yet nobody does for some reason.

Suli Ali: Yeah.

Jess Mah: Do you do this yet?

Noah Berkson: No, even with your friends? That would be super bad.

Jess Mah: Let's do it together.

Noah Berkson: Maybe this is—yeah.

Suli Ali: I think people should do this with their friends because I have a ton of friends. I have some sense of what kind of wealth they have, but not at this level of specificity. It would be so much more interesting to share that stuff with friends. But, you know, it's so weird to be like, hey, on Saturday, let me show you how much money—

Jess Mah: Let's go through our balance sheet.

Suli Ali: Yeah.

Noah Berkson: You say you appreciate Tiger 21 because of this. You have older people who aren't so focused on money, maybe the next step of what I want out of my life or happiness or things like that. But you're still money-motivated, is that correct?

Suli Ali: Yeah, I would say that I have had a toxic relationship with money my entire life.

Jess Mah: Like most people.

Suli Ali: Yeah, probably like most people. My parents were immigrants to the United States, so they came with a real scarcity mindset. Even to this day, my mom will be like, every time we go to a restaurant as a family—which we do such a small number of times per year—when the bill comes around, she's like, let me see the bill, I want to know how much it costs. Then she does the math, like, okay, it was $30 per person, and we had six people. Alright, maybe if we didn't have—maybe if your sister didn't come, it would have been $30 less. She's doing some weird math in her head like that. When the menu comes out, she's definitely looking at the prices first before she's like, what's the dish that corresponds to? I think I just had a bunch of that stuff. Even my brother, to this day, is more worried about running out of money than he is about dying with a giant pile of money. Denzel Washington says this, which is, a hearse doesn't have a U-Haul behind it. So, whatever you do in the world, whatever stuff or money you have, it all goes to nothing when you die. Maybe some of it goes to your kids. Maybe that's good for them, maybe that's really bad for them—who knows? Through Tiger 21, I was like, oh yeah, I'm more focused on saving money and growing this pile of money than I am on using money to make my quality of life better. I've been really reluctant to buy Lambos, watches, nice houses, and even go to fancy restaurants sometimes.

Jess Mah: Still, for a guy who's worth over $30 million?

Suli Ali: Yeah. Even last year, since I started doing Tiger 21, for sure, it's been great because I see—I hang out with those guys, and I'm like, you're just blowing money on stupid stuff, but screw it, I'll do it too. It just makes money matter less, actually. I think that's been super helpful.

Jess Mah: Do you have money goals still, or are you at the point where that's no longer a goal? Your goal is to get married, have children, and perhaps other things?

Suli Ali: Yeah, I think I still have money goals.

Jess Mah: Can we ask what they are?

Suli Ali: It's not a specific number, actually. A good way to put it would be, my brother and I say this to each other: we were put on this earth to create shareholder value, which is such a—you know, I thought it was so fun and awesome.

Jess Mah: So funny.

Suli Ali: Yeah. I used to think it was so clever.

Jess Mah: I've never heard that before, that your life purpose is to increase shareholder value.

Suli Ali: Yeah, it's a little bit snarky. About five years ago, I think we were like, yeah, that's, like, 60% or 70% true. I'm trying to dial it back so that that's not what I wake up thinking about.

Noah Berkson: Shareholder value, though, is you and your brother because you're not taking outside money to invest. This is you and your family.

Suli Ali: Yeah, and it's just to create value, create business value in the world, I guess, is the way to think about it.

Noah Berkson: Where do you want your money to go?

Suli Ali: Like, when I die?

Noah Berkson: Yeah.

Suli Ali: The way that I was raised is kind of like you have a big pile of money as a family, and then you use that to make your family's life better. I think we were at a place growing up where we just didn't have enough money. My parents immigrated to the United States when I was seven. They had a business that was selling textiles. They would import textiles and sell them in the U.S. That business stopped working because they were getting textiles from India, Pakistan, Bangladesh, and then textiles just got cheaper, made in China. So, they got out of the loop; they couldn't do that. My dad spent three years trying to find a new business. If you're a Pakistani or Indian immigrant to the U.S. in that era, of that age, there were kind of three opportunities: hotel, Dunkin' Donuts, or gas station. Those were the three things. My father basically spent two or three years trying to take the money that he had and say, okay, I'm going to use this capital to invest in one of these three things. He ended up in this analysis paralysis phase for three years where he couldn't pull the trigger on buying something. He went to an auction where they were auctioning off closed gas stations. It started in the morning; in the afternoon, he was just like, what am I doing? I'm not making any progress; I'm just listening to these people. So, he was like, I'm just going to bid on the next thing that comes up. Something came up, and he just bid on it. Just like all the previous properties, he thought, I'm the first bid; whoever's the first bid doesn't win it. There's going to be a second, third, fourth bid. He bids on it, and nobody else bids. They say, congratulations, you are now the owner of this closed gas station. He's like, I've never seen it. I don't even know what city that's in. What did I just do? That's all the money I actually have. So, he buys this closed gas station. We, as a family, moved to that neighborhood, to that city, actually, and it's closed. We didn't even know anything about the gas station business. We, as a family, basically opened up that gas station and started turning it into a business. It's so funny thinking back because we didn't know what we were doing at all. A core part of gas stations is selling cigarettes. You have to have cigarette inventory to sell it. We would go to buy cigarette inventory and be like, give us one Marlboro and one Camel, because those were the two brands that we knew. Marlboro and Camel come in, like, 30 varieties. We're like, no, we'll just take one of each. We take that and try to sell it, and people are like, no, I don't want this Marlboro, I want that other one. We're like, oh, we gotta go spend all this money and buy all of the different varieties. My parents did this for 20 years, actually. They ran gas stations. My brother and I would work at the gas station in high school. It was just something that I was so embarrassed about. I didn't want anyone I went to school with to know that, yeah, every Saturday, I spent 12 hours working at a gas station. Sometimes during the week, if I didn't have much schoolwork, my parents would be like, okay, you're not doing schoolwork, come to the store and work here tonight. For a really long time, I was super embarrassed about that. Now, it's so funny because I feel like my brother and I would not be who we are, would not be successful, without having gone through that experience.

Jess Mah: Why? What did it teach you?

Suli Ali: It got us really comfortable talking to people who would come in the door. It got us really comfortable understanding what people want to buy and how to sell something to them. It also got us really comfortable working super hard. Doing a 16-hour shift at a gas station was just something that we thought was normal and that you have to do as a kid growing up in America as an immigrant. It got us super comfortable being like, yeah, I can outwork anyone at any problem, period.

Jess Mah: It also seems like that experience taught you how to work with family and your brother since you still work with your brother a lot right now.

Suli Ali: Yeah, I think it did also teach us the value of family, that you can collaborate and build stuff together, for sure.

Jess Mah: Did you have to learn how to fight properly with your family and argue and then repair, or was it just harmonious the entire time?

Suli Ali: No, I think there was a lot of constant arguing about stuff, and I think it's great because you don't hold something in, bottle it up, and then explode on the other person. You're constantly being like, hey, this sucks, you're bothering me right now, get out of here. You just get comfortable saying stuff like that to each other.

Jess Mah: Say that to your mom?

Suli Ali: Yeah, in a kind way, for sure.

Noah Berkson: Do you and your brother pool resources now and invest together in everything, or is it quite separated?

Suli Ali: We do a little bit of pooled stuff, but probably most of it is separated.

Jess Mah: So, going back to legacy and what you do with your money, there are two trains of thought. One is you should actually spend as much of it as possible while you're still alive because then you can direct it, versus waiting until you're dead, and then you've accumulated and compounded, but you can't be the administrator. How do you think about that?

Suli Ali: I recently read Die with Zero, and I thought it was super cool.

Jess Mah: I love that book.

Suli Ali: Yeah, it's so good. It's amazing because when you read it, you don't realize Bill Perkins is really rich and a billionaire. You just think he's a normal person. That was super impactful in realizing that, yeah, I should be using money to make my life better immediately, and I shouldn't just be trying to—historically, the way I was raised, I've had the mindset of, yeah, you make money so that you can invest it, which will make more money so that you can invest more.

Jess Mah: We never taught this hoarding mentality as a society for some reason. I think it made more sense after the Great Depression. If you're an immigrant, you're starting with such a small base that, even if you accumulate, you're still only a millionaire. They haven't taught you what happens when you're over $30 million or $100 million. Then the rules change considerably.

Suli Ali: Yeah. In fact, I still don't know what the rules are, so you have to tell me how the rules have changed. You get to a place where you're like, okay, making more money is not going to change my quality of life, period. I should figure out how to use the money I have to improve my quality of life. I've definitely gotten a lot more aggressive about anytime I'm like, this would be fun, I'm like, let's go do it. My girlfriend will be like, oh, we should invite these two people. I'm like, great, let's invite them, let's pay for everything, and just tell them we're going to pick you up at this time and just show up. You don't have to do anything. That concept was so bizarre and insane to me three years ago. Now it feels so stupid that I wasn't doing that this whole time.

Jess Mah: Super insightful.

Suli Ali: The other thing I've learned from Tiger 21 is that I always assumed having money would help your kids because that would give them an opportunity to start life out on second base or third base or whatever it is. But everyone in Tiger 21 is so worried that their kids are going to start out on third base and never go anywhere. In fact, they might go backwards. They might not even know which direction to run in and end up at first base. They're kind of pissed at their kids about that and also pissed at themselves for giving their kids such a luxurious life.

Jess Mah: So, what is the best practice then from Tiger 21? Is it to give them more privilege and access and a trust fund and tell them about it, or is that not the best practice? Or is there no best practice?

Suli Ali: I think there is no clear answer. One of the guys will do trips for Christmas every year. They'll do a trip to somewhere like the Philippines or India, and they're doing service for a community as a family. So, instead of exchanging gifts and celebrating by saying, I just bought you a brand-new car because you turned 16, they're trying to see what the rest of the world lives like and give them a different perspective. But I think it's super hard, especially in L.A. I think where I grew up was a small suburb in Florida, and even though a lot of people were rich, it wasn't opulent and gluttonous like it is in L.A., where when you turn 16, you get a BMW. There, it was like you turned 16, and you got a used, beat-up Camaro. I think the world is a little bit different now, and social media has changed the whole optics of trying to keep up with your friends who are posting stuff on Instagram in high school.

Noah Berkson: It seems, too, in some super-affluent communities that if all of your kids' friends have money, and their parents are buying them the BMW, you're almost giving your kid a disadvantage by not giving them that in a way. Because then it's like, well, I don't fit in with the core group that I want to fit in with because I have this beat-up Honda, and they're going to school in their BMW. But I feel like it's so important to have a chip on your shoulder. It feels like the people who are the most successful have a chip, but then there's a difference in chips. There's the chip on your shoulder because you come from nothing, people tell you you won't be successful, no one expects you to be successful. Then there's the chip of, my family's really wealthy, so people aren't going to think I earned it. I think they're very different, and the first is where you see the most successful people come out of.

Suli Ali: Yeah, for sure. Like, Tom Brady will talk about the chip on his shoulder, and he still has it despite all the success he's had. So many entrepreneurs I meet who are incredibly successful have success amnesia and are just worried about the next thing they're working on. They don't care about the previous success they've had, like how happy they are or how confident they are or how good they're feeling professionally—it has to do with their current thing, not the stuff they've done before. I don't know what the chip on the shoulder looks like when everyone else is super rich, and you're just normal rich. I don't know what that looks like. I remember when I was a kid, people would wear brand-name clothing, and I'd be like, let's go buy brand-name clothing. My mom would be like, no, we can't afford it. I remember being like, when I get older, I'm gonna make money so I can buy brand-name clothing, and no one's gonna get in my way, and no one's gonna say no.

Jess Mah: You have no logos anywhere.

Suli Ali: Yeah.

Jess Mah: Now you seem very humble and modest.

Suli Ali: Now that I can, I don't care about any of that stuff.

Jess Mah: It's so funny how that works, isn't it?

Suli Ali: Yeah. In fact, I'll wear the same shirt for weeks at a time, and my friends will be like, didn't you wear that shirt the last time I saw you? I'm like, yeah, I did.

Jess Mah: It's like you got pride now.

Suli Ali: It's not that I've gone the other way. It's actually that I'm apathetic. I just don't care. I'm not trying to prove to myself or others that I can afford X or Y; it just doesn't matter.

Noah Berkson: What's the biggest misconception about you that people have? Maybe I'd break this down into people who don't know you or know you from afar—they know you from the success you've had or Twitter or some of those places—and then the people who are close to you.

Suli Ali: I got on a call with this guy last week, and we were talking about doing some business thing together. He was like, all I've seen you do is have a Midas touch, so I just want to find a way to make the terms of this deal work for you and for me so we can get into business together. He kind of assumed that things I touched were successful. I was like, you have no idea. The things you think about as success are 1% of the things I've attempted. There's 99% failure and pain. If you got five minutes, I can make you sob with pain stories of the entrepreneurial pain I've experienced and the trauma I have from it. He was like, okay, I don't want to hear that in this context. So, I think people from the outside just think that I'm successful, and my own mindset is not that I'm successful. I'm kind of like, actually, I haven't achieved what I aspire to achieve. I would say I probably feel like a failure 75% of the time and success only 25% of the time. The people who know me most—what do they not know? I think a lot of the people I know I met when I was in my 30s, and now I'm 42. I think life—and they're still in their 30s—so all of the things I care about after turning 40, my life perspective changed a lot. I feel like life is so much more fragile. When you're in your 30s, you're like, life is infinite, and I've got so much time ahead of me. In my 40s, I feel like time is finite, I can see the finish line, and I'm constantly thinking about that. I feel like I'm in the third or fourth quarter of my life. It just feels so different. I'm a lot more afraid of things than I've ever been, and I'm a lot more risk-averse in a lot of aspects of my life, which I would have thought would be different. I thought, as I've gotten older, I've got more resources, so even if I lose some of those resources or lose some time, I'll still be okay, so it would make me more willing to take risks. But it's actually moving in the other direction.

Jess Mah: What are you most risk-averse to?

Suli Ali: I'm most risk-averse to death, so just any health stuff—like anybody I know and love having health problems, myself having health problems. For example, my girlfriend and I—she wants to buy a car, and I'm like, cool, let's just start with the safest car and optimize for safety. I don't care if it looks like a World War II tank that you have to drive, as long as you cannot be hurt in it. Let's get that. Just trying to optimize for safety is different than I expected.

Jess Mah: How about business or financially? Are you risk-averse there in a way that you weren't before?

Suli Ali: Yeah, I have this friend, Keith Wasserman, a real estate guy here in L.A. He's bought billions of dollars of real estate and raised a bunch of outside capital to do that. He started a venture fund at some point where he was like, okay, I'm going to do a $5 million venture fund, and I'm going to raise money from the same people I've raised it from. Those people have invested hundreds of millions of dollars with me; surely, raising $5 million, I can do with a single email. He found it incredibly hard to raise $5 million for a venture fund because a lot of his investors are in their 60s and 70s, and they're like, Keith, if I invest in this, I'm not going to see that money back for 10 years, and I might not be alive in 10 years. So, I don't think like that. What I love about real estate is I'm investing now, and you're going to send me a check every month or every quarter for five years. I've not gone that far where I'm like, I'm going to use capital to clip coupons, but I've definitely been more like, I want to find ways to invest that are more predictable and steady than angel investing, lottery tickets, and startups.

Jess Mah: What percentage of your current allocation is into illiquid private investments, such as venture funds and companies, versus, say, real estate or private credit?

Suli Ali: Yeah, so startups and venture funds that are managed by other people versus businesses that I own.

Jess Mah: Yeah, from a dollar amount perspective, percentage-wise, is it 50-50, or is it now 100% liquid that you could cash out immediately?

I explore navigating both the founder and investor mindsets in Investor vs. Founder.

Suli Ali: Yeah, probably like 5% of my net worth is in startups and venture funds, something like that. When I first started making money, it was like 80%. I was living in Silicon Valley, started this company, we raised a Series A, and I did a $3.3 million secondary in that Series A. I took that money and put it all in startups. Actually, I gave half of it to my dad; he put it in real estate, and then the other half I kept and just put it in startups. That percentage has been declining. The percent of net worth in startups has declined over time as opposed to remaining steady or growing.

Jess Mah: Interesting. Cool.

Noah Berkson: How much at this stage do you want to help other people be successful who are around you? I hear you have a spreadsheet of people you've made millionaires, and you keep track of this.

Suli Ali: Yeah, Ray Dalio in Principles—I read maybe half of it, and the thing that was most impactful was in the foreword. He says, I'm at the stage of life where I want success for others more than I want more success for myself. That really hit me like a lightning bolt around the way to think about my life and the good I could do in the world. I constantly look for opportunities now where I'm like, oh, this person is special, and they're an expert in this specific thing. Can I structure something with them or give them what they need to be able to go run at that thing much harder and be more successful and become a millionaire or get $10 million or more? I find myself generally leaning more and more in that direction over time. One of the things I admire most in the world is Mark Cuban has done this thing called Cost Plus Drugs. He's taken the pharmaceutical business model and turned it on its head, where he's like, okay, instead of making so much money selling drugs like pharmacies do, I'm going to run it at break-even and think of it as a public service and public good. I'm doing good in the world. I'd love to find something like that, that is a business, but where I'm not trying to create shareholder value, I'm trying to create good in the world because I think that's super meaningful. I'm surprised there aren't more entrepreneurs who are post-economic who do that type of thing.

Jess Mah: Why do you think that is? Why do post-economic entrepreneurs prefer to chill out?

Suli Ali: I understand why they prefer to chill out. They have this PTSD from their entrepreneurial experience, and they're like, cool, let me not do that. I feel like, personally, I over-indexed on work in my 20s and 30s, and that's why I'm not married and don't have any kids. I really want to spend the next 10 years being like, cool, let me learn how to be a good husband, let me learn how to be a good dad, and let me not work as much as I had historically. I understand why people chill. I don't understand why, when people start new endeavors, they're not like, let me do good in the world. A friend of mine started a company, sold it, got to financial independence, and he was like, everyone who starts a new company, I feel like, is building a prison for themselves, and they're only doing it because that's the only thing they know how to do and the only thing they know that makes them feel good.

Jess Mah: I see that all the time with people.

Suli Ali: Yeah, where do you see that? Tell me more.

Jess Mah: Well, they start a company, sell it, make a lot of money, and then decide to start another company because it's all they know, and they want to make more money. Then they're miserable a year in and think, oh my God, I'm stuck here. I raised all this money, I hired all these people, and they aren't willing to let go of the shackles and say, you know what, this company CEO job thing is not actually what I want to do. I think I want to do it, but I'm not actually into it. They put out this front where they pretend to love the job, but they secretly hate it. I'm sure you see this all the time.

Suli Ali: Yeah, I'm hearing more and more of my friends who are in that situation. Sometimes you just can't get out of it because you're like, well, I gotta see this through. Or, for myself, I bet my ego on this thing, and I want it to deliver. I think that is super common. It's something that people talk about in private rooms, but not otherwise. It makes me respect people like Bryan Johnson even more, where he's like, I'm going in this totally other direction that nobody else thinks about, and I'm going to be a lunatic in this one specific way. It's great. There's this concept of, you climb a mountain, and then there's this book called The Second Mountain, where you're like, okay, I got to the peak of this mountain. What's the next mountain I'm going to climb? People just keep going in the direction they've already been going instead of looking around and seeing what other mountains I haven't even attempted to climb. Let me go see what those are like. Bryan just created a brand-new mountain no one even knew existed.

Jess Mah: It's brilliant.

Noah Berkson: Yeah, absolutely. I think, too, as people get more successful, they become more closed off. They don't go to all the events, do the things, and try to meet new people. If they are going to meet new people, it's like, I want a direct introduction to meet that person. You are not one of those people. I feel like you're extremely open. We met originally because of a Twitter breakfast you threw out in Newport Beach. I think it was, maybe it was a Friday night or something at, like, 6 p.m., and you're like, anyone around for breakfast at 7 a.m. tomorrow in Newport?

Jess Mah: You posted that on Twitter?

Suli Ali: Really?

Noah Berkson: On Twitter, to random people.

Suli Ali: What?

Jess Mah: That's so cool.

Suli Ali: I was like, I saw it.

Noah Berkson: I was like, oh, I'm going to do that in the morning. Sweet. I met a great group of people there. Where else have you done that? Why do you do that? What got you started?

Suli Ali: I think it came from the Silicon Valley ethos, which is, anytime you meet somebody, you're like, this could be the next Mark Zuckerberg; the world just doesn't know it yet. I approach life thinking that, which is, I'm meeting these people, their stock is low, and their stock is going to skyrocket. I'm going to be like, I knew you when you were nobody, and how awesome was that? I've known a bunch of people now who started out with some idea, and I met them, and I was like, this idea is terrible, and you're terrible. Then they've gone on to be way more successful, way more thoughtful, way more articulate than I ever have been. It's humbling and inspiring, and it's great. Even people who have worked for me—a bunch of them have gone on to be super successful. It's awesome to see how many—

Jess Mah: Millionaires are on the spreadsheet?

Suli Ali: Probably, like, I don't remember offhand, but something like 15 to 20.

Jess Mah: That's a ton.

Noah Berkson: That's a lot of millionaires.

Jess Mah: What's the path they took to become millionaires?

Suli Ali: Some of them worked for me at TinyCo. Some of them, I saw this opportunity where I could buy a business, and they could run it, and did that. One of them was just like, I have this business idea; nobody will invest in it because it's not a classic startup fundable idea. I was like, cool, how about I'll own 49%, you own 51%, and that's what makes the economics and investment work. Stuff like that.

Jess Mah: Wow.

Suli Ali: There's sort of venture capital and private equity, and the world has been weirdly super separated between those two things, where private equity is on the East Coast, and venture is on the West Coast, and the two shall never meet. Now I think there's a lot of gray area where people are like, I made money doing venture, but I'm going to try to invest in small businesses in a private equity style way, where the likelihood of success is high. Instead of putting a $50,000 check in and owning 2%, I'm going to put in a $250,000 check and own 25% or whatever it is. I think that's cool, and we're going to see more of that.

Noah Berkson: Our mutual friend Ben Levy said I have to ask you about Dory, which I have no idea what that means. Can you tell me about this?

Suli Ali: Yeah, I can tell you about it. I was on Amazon one day trying to buy a product, and I saw this brand that I'd never heard of before. I was like, I wonder who owns this? I went on LinkedIn and saw it was owned by this woman, and she was connected to this person I met one time at some random event. I had that guy's email, so I emailed him and said, who's this? What's this brand? Tell me the story. He was like, I don't know, but here's an intro, and just introduced me to her immediately. I got on the phone with her the next day and was like, tell me about this business and how you started it. She told me about it; she started it 10 years earlier. I was like, is this something you'd ever want to sell? She was like, actually, yes, I would totally sell this business. I was like, cool, how much do you want for it? I think she was like, $10 million or something like that. I was like, $10 million is insane, but I would buy it for $5 million. She was like, okay.

Noah Berkson: Knowing nothing really about the business, maybe, like, top-line revenue?

Suli Ali: Yeah, she was like, here's the top line, and here's the bottom line. So, I was like, here's the ballpark. Okay, cool, let's see if this works. I'd never bought a business.

Jess Mah: What's the multiple you offered? Do you recall?

Suli Ali: Yeah, it was, like, a 10x multiple.

Jess Mah: 10x EBITDA?

Suli Ali: Yeah, 10x.

Jess Mah: Wow, that's rich.

Suli Ali: Yeah, it was super rich.

Jess Mah: So, this is doing $500,000 in really seller discretionary earnings because it's a tiny business. You offered 10x?

Suli Ali: Yeah.

Jess Mah: Why?

Suli Ali: Well, I didn't know anything about buying businesses, so I wasn't—I didn't know any better. I was too stupid to know that that was a crazy number.

Jess Mah: Wow, great deal for her.

Suli Ali: Yeah, well, let me tell you—a great deal for me too.

Jess Mah: Great deal for you too.

Suli Ali: So, then we get into this due diligence process that's super light. She sends me her financials, and I look through them. I'm like, this doesn't make any sense. She's like, oh, we actually double-counted revenue here, so EBITDA is not $500,000; it's actually $350,000.

Jess Mah: Oh, no.

Suli Ali: I'm like, oh, well, this is valued on an EBITDA basis; that means the price has to go down. She's like, no, $5 million is my number. I don't care about what these numbers say; give me $5 million bucks, or there's no deal. I was like, forget it, I'm out. Then I waited three weeks, and I was like, there's some percent chance she's going to come back and be like, alright, let's do the deal. She didn't come back. After three weeks, I went to her and said, okay, fine, let's just do the deal at that price. Every time I called her, she was, like, busy during that diligence process. She was like, I'm in the car; I'm on my way to take my kid to a soccer game. Oh, you have this question about the business? I don't really know anything about that; ask this guy. I would talk to that guy, and that guy was dumb as a rock, just completely incompetent, so bad at what he did. I was like, oh, there is nobody at the helm of this ship. This is completely absentee; there is no management; nobody is paying attention to any of this. That means this deal is even better than I thought because if you put a warm body there, the business will perform better. The business had been growing every year for the last five years despite the lack of active management. They'd also spent no money on marketing. I was like, oh, if you just put a warm body and spend money on marketing, this business will grow. I also wanted to see, can I have success without paying for it in my own blood and tears and that of others, in hers, in that she spent 10 years building this business? Could I get somebody who would never start a business on their own because they didn't want to take that zero-to-one risk, but given a business in a box, they would be incredible at operating, optimizing, growing, and making it better every day? It's been a real win-win-win for everyone involved. Win for her because she got paid and didn't have to run it anymore. I told her, the only thing better than running your own business is not running your own business. I keep in good contact with her, and she's so happy not running the business and living her best life. Win for her. My definition of win was, I don't lose money, and I don't have to do any work—so I've done no work. Win for the guy who became the CEO in that he got to be CEO of a business, he's got to grow it, he's enjoyed that process a lot. He has made a bunch of money through that process—way more money than I thought he would make. It's been really fun and makes me want to find other ways to do that because it's so cool. The way I think about it is, if I were to die tomorrow, I'm not sure who's going to show up at my funeral, but I know that guy who's the CEO of this business will show up at my funeral because I've changed the trajectory of his life, period.

Jess Mah: Wow. What were the terms of your CEO's offer?

Suli Ali: I probably don't want to share it publicly, but the way I structured it is he gets a percentage of EBITDA that the business generates. Basically, what's happened is the EBITDA has just grown astronomically, so his comp is insane.

Jess Mah: So, he got a base salary and then a percentage of EBITDA once it passed a hurdle?

Suli Ali: Yeah.

Jess Mah: Did it stair-step, so he got a bigger percentage of EBITDA as it passed hurdles? Were you that creative, or just, like, straight line—you get X percent of EBITDA?

Suli Ali: Yeah, it's X percent of EBITDA; it's uncapped. I think I was really stupid in the way I structured it.

Jess Mah: How would you have structured it in hindsight?

Suli Ali: I would probably change the floor. The business needs to continue to grow its EBITDA to make massive amounts.

Jess Mah: It's like, you have to get X percentage of EBITDA subject to the growth rate being at least Y percent a year.

Suli Ali: Yeah.

Jess Mah: So, if the growth rate has gone down to no growth, then you're back to your base or some other normalized—

Suli Ali: Yeah, the way I structured it was, oh, you were making this much money in your current job? Okay, in your first year, you're going to make this much through a combination of base and EBITDA. I would probably do something like, in year three, you don't get credit for the EBITDA that—let's say the business generated $2 million in EBITDA last year—you're not going to get full EBITDA for that $2 million in year three. You're going to get some smaller percentage of that $2 million, and you're going to get a larger percentage of the EBITDA above $2 million.

Jess Mah: Okay, so there's, like, a declining tail, essentially.

Suli Ali: Yeah.

Noah Berkson: This has been awesome. We really appreciate you coming here.

Suli Ali: Yeah, thanks for having me.

Noah Berkson: You are our first guest ever.

Suli Ali: Love it.

Jess Mah: Yeah, thank you.

Suli Ali: So excited. You guys are gonna be so good at this. The tag-team pair is always such a good model for this.

Noah Berkson: Really appreciate you. Let's hang again soon.

Suli Ali: Can't wait.

The episode is called "The Secrets To Building a Powerful Network of Friends w/ Noah Berkson".

We talked about cold outreach, handling objections, and the biggest mistake people make about networking.

Here are other topics we discussed:

• Make introductions the right way – Always provide context so both people see the value.
• Say yes to everything in your 20s – Opportunities come from showing up.
• Pick up the tab – When dining with someone much wealthier, covering the bill makes an impression.
• Make friends, not “connections” – Real relationships > transactional networking.
• Find your X factor – I cold-DM’d Jess Mah because she flies planes. A unique hook stands out.
• Vulnerability is underrated – Being open, stumbling, and failing brings people closer.

Listen Here

Tune in and listen to the full conversation here.

The Secrets To Building a Powerful Network of Friends w/ Noah Berkson

You can also listen to the episode on Spotify by clicking here.

Full Transcript

Noah Berkson: There are people who are starting out in this, and then there are people who are a little further along in their career. Early on, saying yes is a superpower; later on, saying no is a superpower.

Andrew Namanny: Ladies and gentlemen, welcome back to Permission to Shine. It’s your host, Andrew Namanny, and we are going to be covering the topic of building a network and meeting the most interesting people on this planet. Today, I brought on none other than Noah Berkson. He is a serial entrepreneur who has exited multiple companies. He’s in YPO, gets to meet a lot of interesting people, and he’s also the host of a new podcast called Dose of Greatness. He and his business partner, Jess Ma, who’s extraordinary—if you don’t know Jess, she’s 34, she’s started over 10 companies at this point, has a commercial pilot’s license, flies her own plane. Mad interesting. So Jess and Noah recently hosted Outcove Valley, where they brought together 65 of the most interesting entrepreneurs in Utah. I talked about it on the last episode with Garrett Adair. It was an extraordinary event, and it reminded me that Noah is an incredible networker. So I want to invite him on to share with you guys tips and tricks. How do you perfect the cold outreach? How do you push through when people are telling you no? And where should you be hanging out if you want to meet the most interesting people? So please enjoy this conversation. If you do, do me a solid: share it with somebody you love. It will mean the world to me and make a big difference in the show and my ability to get you guys extraordinary guests. Let’s get into it with Noah Berkson. Noah, in 30 seconds or less, how would you introduce yourself?

Noah Berkson: I am a serial entrepreneur. I call myself relentlessly resourceful. I’ve started seven companies, sold three, currently run a platform of fintech and financial service businesses where we own, operate, and invest in financial service and fintech companies. We host a podcast called Dose of Greatness along with an event series called Outcove Valley, which is a community for entrepreneurs and investors, thinkers who want to go deep and make lifelong connections.

Andrew Namanny: Love that. Welcome to the show, Noah.

Noah Berkson: Thanks for having me.

Andrew Namanny: You have one of the best networks I’ve ever seen. I feel very fortunate to meet a lot of people who have incredible networks, and you are certainly at the top of that list. Were you always super intentional about building this network?

Noah Berkson: I built a network out of necessity originally. Like you, I grew up in Iowa. I didn’t know what a network was, had no clue. But I started a business in college, and it was out of necessity because I needed to go sell a product. And so I went from knowing virtually nobody, you know, outside of, like, the people I went to high school with or the people that I was in college with, to I need to meet, like, real adults, and I need to sell them a product that’s very expensive. And so I went to—I mean, I just—I went to everything. I said yes to everything, went to every happy hour, went to every networking event. Anytime someone would invite me to go to coffee, I’d go with them. If someone would write me to do a phone call, like on LinkedIn, even if they were trying to sell me something, I’d end up taking that phone call just to, like, meet that person, because maybe they’d introduce me to somebody else that I could sell a product to. I talked to tens of thousands of people.

Andrew Namanny: Wow. How quickly did that work for you? Did it take time, or was it pretty instantaneous?

Noah Berkson: It definitely took time. I think probably this started when I was, like, 19, and it probably took till I was 25. And the way that I would measure that is when I meet somebody and then they introduce me to somebody else, like, what’s the quality of that person they’re introducing me to? And I think it took probably about six years to get to that where the quality was so consistent. Every time somebody introduces me to somebody, it’s like, that’s a high-quality person that I’m meeting. It takes a long time. I think a lot of people underestimate it. And they go, oh, I just need to go to, like, one dinner. I need to go to one networking event, and I’m going to meet, like, my best friend. I’m going to meet the person I’m going to do business with. And it’s just not like that. It’s such a numbers game, and you have to put yourself out there.

Andrew Namanny: I love this. I really want this to be a masterclass on networking, right? So if you’re somebody who’s listening to this and you feel like you don’t have the network you want, I want Noah to be able to teach you how to build that. If you’re somebody who does have a network, how do you elevate that to even the next level? Because hopefully you’re somebody who has that growth mindset. And so let’s just start at the top. Where do you think somebody should start if they want to build a powerful network?

Noah Berkson: I think you start by saying yes. I think there’s a lot of power in being the person that just says yes to everything. I think when you’re early on in your career, you just have to say yes. You have to go to everything. Like I was saying, you go to every happy hour event. You go to every conference that you can go to. I mean, when I was young, I would sneak into conferences. I’ve snuck into probably 20 conferences. I would go because when I was younger, I couldn’t afford to go, right? And it’d be like, oh, it’s South by Southwest, let’s say, right? I have a great story about going to South by Southwest. We were there, and I didn’t have a ticket, and it was just too expensive. I was like, how do I get in? I kind of tried to—I saw the escalator, and there’s, like, a guard there, and then there’s a guard on top. Like, I can’t really go there. Like, is there a back door? Is there a way to get in? Nothing. And so I look and, like, who’s speaking today, right? Like, how can I use one of these people to try and, like, talk my way in, like I know them? And so I go up to the speaker’s desk—like, there’s a desk for speakers where they check in. And I go up there all frantic. And I’m in just, like, a black T-shirt and jeans—like, I look like I could probably be, like, security or, like, I work there. And I go—I come up there frantic. I go, oh my God, I’m here for Howard Schultz. He was the CEO of Starbucks, and he was speaking. And I said, I’m here to pick him up, to bring him to his next event after he talks, but they didn’t give me a badge. And I’m just, like, acting frantic, and I’m like, I’m gonna get fired from my job. And they’re like, don’t worry, we got you. And they hand me an all-access pass, and they’re like, here, let us escort you there. And now I’m, like, backstage for where Howard Schultz is speaking and end up, you know, end up in there. And I’ve just—I’ve done this time and time again.

Andrew Namanny: How nervous are you at that moment?

Noah Berkson: Oh, incredibly nervous. But I think once you just kind of, like, go through those repetitions, I think just generally this is good to be able to—to be able to kind of, in the moment, like, have to figure it out. And I’m like, I don’t really know what path I’m going to go down if they ask me what question, but I’m going to have to figure this out on the fly.

Andrew Namanny: Dude, that’s so good.

Noah Berkson: I think it’s saying yes to things. I think it’s going to anything that you can go to. I think it’s just being proactive. I think a lot of people—they just don’t—they just aren’t proactive. And you need to be so proactive to really build a network. And you need to invest in relationships. I think something a lot of people get wrong about relationships is there’s, like, this—like, momentum. Like, momentum in life is everything, but especially in relationships. And I think there’s this momentum where, let’s say I meet you, right, for the first time—like, there’s this window of momentum where I can either be your friend and we’re going to develop a really close friendship, or we’re just going to be, like, loose acquaintances forever. And in that time, you need to really invest. So I meet you on, let’s say, a call. We do a Zoom call, and we, like, get along. And I’m like, oh, like, I like Andrew. I go—I need to say, hey, let’s—next Saturday, like, let’s go get a coffee, right? Or you should come over to do this thing, or let’s go do a workout, or let’s do something. And once we do that, it’s, like, there’s a very high likelihood we’re gonna be close friends, right? And we’re gonna actually, like, we’re gonna get along. If I don’t do that, like, most likely we’re never going to—we’re never gonna be close friends. You’ll be a loose acquaintance. I’ll be able to say I know Andrew, but I’m never gonna, like, get that—get the special, like, the magic that happens from this relationship.

Andrew Namanny: So you’re saying you and I get set up on a Zoom on Tuesday. Then we’re going to have that. You’re going to say, okay, Andrew, somebody that I find interesting, I want to build a friendship with him. You’re going to say, let’s go have coffee on Saturday. Yes, we have a good coffee. Then what are you going to do?

Noah Berkson: I’m going to propose the next thing, which is always trying to propose the next thing. That’s probably going to be, hey, I’m going to host a dinner, and why don’t you come, and I’m going to invite another person or a couple other people that you’re going to find very interesting and vice versa.

Andrew Namanny: Yeah. What if I say no to that? Like, I’m just like, you said yes—I totally agree with that. For my 20s, it was all yes, yes, yes to everything. And now I’ve entered my no era, which sucks in a lot of ways, but it’s very empowering in some ways. I can’t say yes to everything now. As badly as I wish I could hang out with you, I have to say no to this.

Noah Berkson: I’m going to keep trying, and I’m going to invite you to a couple more things. Like, something that you realize is, I think there’s a distinction, right? There are people who are starting out in this, and then there are people who are a little further along in their career, right? We’re, like, saying early on, saying yes is a superpower; later on, saying no is a superpower. So I think it’s—I think it’s very—I think there’s maybe two paths that we can go with this. If you say no, I’ll invite you a few more times because I know, hey, let’s say I’m later along in my career, and I’m going to say, I know Andrew’s busy, so he might just say no. But I’m going to keep inviting him because I’m going to be on Andrew’s radar now, and he’s going to know that, like, I—I care because I keep reaching out and I keep inviting him to events. And even if he says no, like, the likelihood eventually that you’re going to show up is pretty high because eventually, like, you’re going to have—you’re going to have an excuse the first time, right? You’re, like, I already have a—I have a trip this weekend, and the next time, oh, I have this conference I’m going to. And the next time, like, eventually you’re going to run out of excuses, and either you’re going to have to say, hey, I’m just not going to come, or you’re just going to stop responding to me. So it’s, like, I’m going to end up understanding what—like, how you actually feel about it because a lot of people aren’t really upfront right away.

Andrew Namanny: Do you take it personally when people say no to you to these things?

Noah Berkson: I used to take it more personally, but I think it’s value, right? So I think, yes, there’s a piece that people are just busy, and successful people—the biggest thing to protect is your time, right? Like, your time is going to be your most valuable asset. So if someone keeps saying no to me, it’s pretty clear, like, they don’t see the value in what I’m bringing to them. And so then it’s a chance to kind of step back and say, how do I reevaluate? What value isn’t there? What am I not bringing? And sometimes I’ll ask people, you know, I’ll be very direct and just ask, like, hey, you keep saying no to—you keep saying no to these things. I think this would align really well with you, where the people who are there would align really well—you’d really like them. So, like, what’s the reason you’re saying no?

Andrew Namanny: I think, having seen you build your network, I think that persistence is so fundamental to it and not taking it so personally when people say no to you. Like, the special relationships in my life that I think about, that really helped me from a business standpoint—dude, I would ask them seven, eight, nine times. Yeah, getting no’s in a row, and I’m just like, I don’t give a shit—like, yeah, I believe in this. I know that we’re supposed to be on the same path together, so just keep doing it.

Noah Berkson: Yeah, there’s so much power in persistence and just over and over and over and not letting your ego take a hit. It’s really easy early on to let your ego take a hit. And you also go, like, hey, I meet somebody, and we get along really well. And then I see, like, you know, I don’t know, they’re hosting some event or a party or a dinner, and I’m like, why did I not get invited to that? Like, why aren’t—why aren’t they inviting me? And again, you have to ask yourself, like, well, why aren’t they? It’s easy to say, like, oh, they just don’t like me. But it’s, like, well, is it the people that they’re there with? Like, you don’t think that I would mesh really well with them? Like, what’s the value, right? And just understanding, like, how do people perceive you? And very few people actually take the time to think about, like, how am I being perceived, and what am I doing that, like, either makes somebody like me or makes me magnetic as a person or makes someone say, I don’t really want that person—like, maybe I want to hang out with that person one-on-one, but I don’t really want to bring them around, like, my friends or my network or introduce them to people that I know.

Andrew Namanny: Yeah. That word “magnetic” that you just used—that’s interesting. What do you think is something that everybody could do to make them more socially magnetic?

Noah Berkson: There’s probably three things. Two are very basic. Smile—like, just look like you have energy, right? A lot of people are—a lot of people are sitting there—they’re, you know, kind of disconnected in social environments where they’re, like, sitting there on their phone, like, pretending they have something better to do because they’re just not getting the interaction they need in those moments. So they just sit there on their phone, and it’s, like, nobody wants to approach somebody that’s sitting on their phone. When you’re, like, looking down and you’re texting, no one’s going to come approach you and, like, try and talk to you. Why would you do that? Like, you need to be inviting. And I think just smiling goes such—just, like, smiling goes a really long way. Making eye contact with people. And so actually, just, like, making good eye contact is another one that people just don’t do well. They kind of, you know, you see people at, like, an event, and you kind of just, like, look down—you, like, sort of acknowledge them, but you don’t fully acknowledge them, and you look down—just, like, just make eye contact for a second. And most of the time, that’s going to lead to you actually going over and talking to that person. The third would be, and probably the most important, is just curiosity—just being curious. I think people love—like, people underestimate how much people love to talk about themselves and love to share their story. So if you can just go and be genuinely curious about someone, people want to talk to you. I’ve had, like, funny scenarios or situations where I’ll meet someone for the first time at some event, a conference, a dinner, and they’ll go, like, that was one of the best conversations I’ve had in a long time. And in my mind, I’m like, I didn’t really talk about myself at all. I just asked you questions—like, you just talked the entire time, and you’re, like, in their mind, like, this was the best conversation I’ve had in a long time—like, interesting. So I think just being genuinely curious about people and asking questions is something that’s going to get you very far.

Andrew Namanny: So good. Noah Victor Vascovo, one of the most interesting humans on the planet, famously said, “If you want to be the most interesting person in the room, be the most interested.” And I think you do an exceptional job of that.

Noah Berkson: Yeah.

Andrew Namanny: You talking about kind of body language, smiling, eye contact—I love eating by myself. Last night, I went to Pachay.

Noah Berkson: Yeah.

Andrew Namanny: You’ve been to Pachay and—

Noah Berkson: Love Pachay.

Andrew Namanny: It’s so good. Laurel Canyon, by myself.

Noah Berkson: I used to live right up the road from it. Yeah. I would walk down there for dinner. Yeah.

Andrew Namanny: It’s so good.

Noah Berkson: Yeah.

Andrew Namanny: And walking is great because the parking is a freaking mess. And I sat there, and your natural tendency is—it’s kind of fidgety. You’re, like, I don’t know where to look. I don’t know what to do. I don’t want to sit on my phone—

Noah Berkson: Right. That’s not—

Andrew Namanny: That’s not my vibe when I’m there. I had to get a couple things done, and then I want to put my phone away. And it’s, like—but, like, where do I look? And it’s, like, I’m consciously thinking—it’s, like, okay, take up space, right? Don’t cower. Don’t—don’t try to minimize your space, which is my natural tendency. It’s, like, take up space. Look at people, you know? But it’s awkward.

Noah Berkson: It’s awkward. And I think it’s—I think there’s also—I don’t know if this is a rule of mine, but people who eat alone are genuinely quite interesting and, generally, like, you can make some really great relationships from finding the people who are sitting alone and having dinner. I actually—I have a good story about this.

Andrew Namanny: Do tell.

Noah Berkson: My girlfriend and I were in New York. This is probably, like, two and a half or three years ago, and we went out for dinner, and it was, like, our date night. And of course, I didn’t make a reservation—I was supposed to. And so we tried to walk into this place for dinner that we wanted to go, and they say, oh, we only have room at the bar. And it was, like, the whole restaurant’s full, but the bar is empty. And there’s one guy sitting at the bar, and he’s, like, in a sweatsuit—like, an older guy in a sweatsuit at, like, a very nice restaurant. Totally, like, out of place, sitting at the bar. And so we go, and we sit, and I’m just thinking, like, this guy—you get a sense about people, right?

Andrew Namanny: Your siren’s going off.

Noah Berkson: I don’t know. He just seems out of—like, seems out of place here. He’s sitting by himself—like, okay, like, I kind of want to talk to him, but it’s, like, I’m right here. Then my girlfriend’s between us, and then he’s sitting on the other side, and there’s maybe one chair between my girlfriend and him. And I’m just, like, you know, I’m trying to, like, be in this date night, but also you’re thinking, like, oh, what’s—what’s going on with this guy over here? It’s just, like, an itch I can’t scratch. And then finally, he, like, opens up this—he opens up this conversation, and he starts—he says, like, hey, what are you guys doing here? And I’m trying to make small talk—I’m trying to, like, not ruin this date night of, like, we hadn’t had this in a long time—trying to not ruin it. And I’m, like—but I know the deeper I go, the more that I’m going to—like, I’m going to get sucked into the conversation—like, the deeper I go, the higher likelihood I’m going to get sucked into this conversation. I forget what he mentioned. He said, like, you know, I live here now. I’m retired—like, I have a couple kids in college here, so I moved to the city. I’m retired. He’s, like, but I work—like, I work a couple hours a day. I was, like—like—like, that’s really—like, okay, I kind of need to know now—like, you’re retired, but you work a couple hours a day? I’m, like, oh, what do you—what do you do—like, what do you—what do you do? He’s, like, oh, I’m in—I do, like, I do loans—bridge loans for—for commercial real estate and development. I was, like, oh, cool, cool, cool. And he just starts talking about, like, oh, I just got this house over here—I’m living close by, whatever. And I go—I’m, like, just super curious—this is a random question—how much money do you make working a couple hours a day? I just thought that would either shut the conversation down entirely, and then we can just get back to dinner, or it’s going to lead to this probably really interesting answer. He’s, like—like, last year or so far this year? And I’m, like, so far this year. And we’re probably in June of this year. He’s, like, made about $21 million. And then I’m, like, oh no—like, now I’m, like, totally—my girlfriend—now I’m, like, totally sucked into this conversation. And start, you know, start talking to this guy, and—and end up—we have a great conversation. He’s, like, oh, we need to, you know, we need to get together again—at some point—like, I’d love to get together—let me get your contact information. And one—one rule I have that I think is actually just a great rule in networking—whenever you have a meal or go do—like, go do something with someone who is more successful than you are, always pick up the check—always pick up the check—because for people who are really successful, generally, they just expect they pay for everything—they just get used to, like, it’s always on me. And it’s, like, a—it’s generally a pretty small thing, but to them, it’s a very big thing that someone else, like, just picks up the tab. So I go over to the bartender—like, I go to the end, you know, kind of try and sneak to, like, get the bill, because we’re leaving, but he’s still there—and, like, hey, can I pick up this guy’s—this guy’s tab? And the bartender, like, looks at me with his eyes kind of big—he’s, like, are you sure you want to do that? I’m, like, what do you mean? He’s, like—he’s sitting there, like, having glasses of wine—he’s, like, let me go check on his tab—his tab’s almost $700. He’s, like, are you sure? And I’m, like, yeah, just do it—like, I’m in it now. And so I do, and we leave, and I get a text maybe an hour later—he’s, like, this is the kindest thing a stranger’s ever done for me—like, let’s get—let’s get together this next week—like, how are these dates, you know? And if there’s anything I can ever do—like, I’m here. And I was, like, that was an expensive one—but you’re, like, oh—like, you just made—you know, you just made a really good friend and someone I still keep in contact with.

Andrew Namanny: You still do—you guys are still friends?

Noah Berkson: Yeah.

Andrew Namanny: Oh, I love that—nicely done. That’s a beautiful story. What’s something that you think people get wrong about building a network?

Noah Berkson: I think people look at networking as, like, this idea of network—to me, like, the definition of—of network is friends. So I think a lot of people look at networks not as friends, but as people I can get something from—like, that is their definition of network: people who can do something for me. And so they act as such in those relationships, which is, what can I get out of this person, and what can this person give to me? And I think when you start any relationship that way, there’s very little chance that’s ever going to be a fruitful relationship from any capacity or very long-lasting because it’s transactional in nature, and it’s not a friendship. So there’s not gonna be that deep-rooted relationship you’re building ‘cause you’re approaching it from the mindset of I need to get something from this person. And then when you feel like you need to get something from someone, it kind of goes on a timeline—so you go, how do I get something from this person as quickly as possible, right?

Andrew Namanny: That’s not gonna happen, dude—this shit takes time.

Noah Berkson: Yeah—so it’s, like, hey, we meet, and then, you know, you—and then I go, hey, Andrew, can you introduce me to this per—like, I went on LinkedIn and saw you’re connected to this person—you introduce me to them, they’d be a really good client for me—awful—you’re immediately going to shut down—you’re going to say, like, I don’t want to introduce someone to this person just to sell something to them. So I think it’s just approaching things from the—like, a network is people I can derive value from and I can just take from as opposed to I can give to.

Andrew Namanny: Do people ever call you a social climber?

Noah Berkson: I have never—I’ve—I’ve never heard that—I really hope not—that would be the—that would be me failing in everything I’ve ever done. I would say I try to give so much value—and I—I was just thinking about this the other day—like, when—when someone asks, like, have you ever called on that—what you’d call, like, a reciprocity bank, right—of, like, you kind of think of it like a bank account, right—and it’s, like, you’re—you’re paying out all this—like, giving value to people—have you ever—have you ever asked people for something—right—and tried to get some, like, reciprocity for what you do? And I’m, like, I can’t think of a single situation—wow—where I’ve asked somebody for something—I hate it—and honestly, it’s probably to my detriment a little bit where, like, I just won’t even ask someone—I’m, like, I will go so far out of my way for someone without them even asking just to be helpful—but then, like, if I need something, I’m really bad about asking—like, I don’t want to inconvenience them, even though they’d do it in a second if I asked—I’m, like, I don’t—I’d rather just figure that out myself.

Andrew Namanny: So you started building your network because of necessity a decade-plus later—where is the motivation now?

Noah Berkson: I think now a lot of it is—is genuinely just building the—building more of a network for the sake of the network that I have. I think I get so much satisfaction out of building value for other people around me—and so, like, the people I have today, it’s, like, who would they benefit from meeting—and, like, how can I meet those people that they would probably never meet and then introduce them? And then maybe they go do business together, they do deals together, they become friends—like, those are the things that really fulfill me. It’s funny—when somebody—I’ll make an introduction for someone or do something for someone, they’ll say, Noah, what can I do for you—you know, you’ve been so helpful—what can I do for you? And my answer every time is, if you ever meet anyone really interesting, just introduce them to me—and they’re—they’re, like, that’s not really a great answer—like, that’s not really what I’m looking for—like, well, who specifically? And I’m, like, no, I don’t—I don’t—like, I don’t need—it’s—it’s not that I want to meet someone because I need something from them, right—or I’m trying to sell them something—it’s, like, I genuinely just want to build new friendships and bring more interesting people into my orbit because that benefits the whole of the network that I have, and that makes the network that much stronger.

Andrew Namanny: How many introductions do you think you’ve made in the last 12 months?

Noah Berkson: I would bet near a thousand—yeah, I think that’s one of the easiest ways to build value, especially right when you meet somebody new, is to just introduce them to other people—and also it’s, like, that makes your value so much more because when I meet you and I immediately just introduce you to a few really good people that are in my network that I know are going to really like you and you’re going to really like them—my value to you is a lot higher, right—immediately I become really valuable because I’m, like, that conduit or that connector between those people, and I don’t need to do anything—and that’s so easy—that takes me two minutes, right—of, like, a text intro or an email intro, but I do that religiously—I mean, I do that every day—I have a to-do list, and that is always on it—so I just make three intros.

Andrew Namanny: What are the ingredients to a really good introduction?

Noah Berkson: I think it’s a clear why you guys would get along or why I’m introducing you. There are some cases where I—this takes a very long time—there are some cases where I just—I have enough social capital, right—that I can introduce you to somebody, and I—I just say, Andrew, David, meet—you guys will get—like, have coffee—you guys will get along great—I don’t even need to give more context—I just know, like, you’re going to trust me that I’m making a good introduction for you.

Andrew Namanny: That’s later in the game.

Noah Berkson: That’s later in the game.

Andrew Namanny: That’s after you’ve made seven introductions for me—and I’m, like, anyone Noah introduces me to—

Noah Berkson: That’s after you’ve made a lot of introductions—I think at first it’s being very clear about why you think two people would—would get value from each other and making sure of it—I think something people get wrong is just introducing people to introduce people—and then if—because if—if you have a bad interaction with somebody, right—then both of you have a very negative interaction or thought of me, right—so if that doesn’t work out like that, that’s kind of on me—and so I want to make sure every time you guys are going to have a very positive interaction—so it’s very clear—like, hey, I think you guys should meet because of this—maybe here’s something you have in common—I think some things that are really hard to introduce—like, I’ve met a lot of—I’ve met a lot of wealth managers—a lot of great wealth managers—really hard to introduce them to people—and a lot of times the first thing they ask is, like—or I go, hey, who can I connect you to—any successful entrepreneur—you know, friends of yours—anyone that’s, like—you know, running a big business or selling a business—I’m, like, oh, man, that’s such a hard one—because, like, the moment I introduce you, I know this is going to be such a—the other person is going to—they’re going to text me and go, no, really, they’re just trying to sell—those are genuinely really hard—but I think the dynamic of people trying to sell someone something—I want to make sure that’s not going to be there when making an introduction—and I’ll make that clear to someone—I’ll say, hey, I’m going to introduce this person—do not sell them—like, here’s the—here’s the other reasons you guys should connect, but do not start the relationship on the basis of I’m trying to sell you something.

Andrew Namanny: Do you have a great opener for somebody that you see in person, live, that you want to approach?

Noah Berkson: I would say one of my—I don’t know if it’s a great opener—I think a lot of people ask—one of the first things they do, especially in, like, kind of networking environments—like, what do you do—what do you do—and no, no, no—nobody wants to answer that question—it’s just—it’s, like, it’s kind of like, how’s your day—and people go, good and great—like, that’s not going to lead anywhere—I’ll say—what—what gives you energy in what you’re doing—and completely takes the question from, like, I have a prerecorded answer to what somebody asks, right—to—oh, actually—like, you actually are interested in me—oh, let me tell you—I’m actually, like, this gives me a lot of energy—and people seem to resonate really well with that.

Andrew Namanny: Interesting—I love that—I—I’ve been using lately is because I’m worried if somebody comes up to me that they’re going to linger, right—it’s, like, they’re going to say they’re going to stay too long—I think people want to know that it’s, like, a short window of time and that they have an easy out if this goes bad—so I’m curious if you’ve ever tried this—I’ll go up to somebody, say, hey, I can’t stay long, but I just saw you—I thought you looked super interesting, and I wanted to introduce myself—boom—and then from there I got to figure it out—but I think that opener just gives people reassurance that this guy’s not going to linger—and it’s a compliment—hey, thought I was interesting—you know, we all want to be interesting.

Noah Berkson: There was a—that’s a great opener—um, I’m remembering this from—did you ever read The Game by Neil?

Andrew Namanny: Neil?

Noah Berkson: I did note that that was something that they used—that actually, it works in any conversation, to your point—but I think especially in dating, where he would approach—when he would go approach women in public because, like, people don’t want you to linger there in conversation—so he’d say, like, I—hey, I just want to—I—I just want to bother you—do you—for one second—like, do you have just one second to answer a question, or do you just have a short—like, I’m giving you a very short window, right—that I’m going to be here—can you answer this—so that people don’t feel—you know, they don’t feel, like, oh, you’re just going to be here, and now I’m stuck in a conversation—so, like, I should just avoid this entirely instead of be in this conversation.

Andrew Namanny: Yeah, well, we’re on the topic of dating—you’ve had a long-term girlfriend, but I’ve been super curious about this lately because, you know, I’m single, and, like, I meet interesting women, and we go on a few dates, right—but then we figure out that we’re not a romantic match for each other—but I still want to keep this person in my life as a friend—do you have experience with that and, like, what are your general thoughts on it?

Noah Berkson: I think trying to build friendship first is really important—and so I think even when I would go into—like, in the past, even when I would go into, like, dating environments, I’d try and keep the initial one, two dates—maybe three dates—as I’m, like, building a friendship here as opposed to—it’s kind of, like—it’s kind of like what people get wrong with networking sometimes too, where they’re, like, they’re so focused on that one outcome that everything—like, it kind of gives you just, like, blurred vision—and you can only see that outcome where it’s, like, just start as a friendship, right—and just, like, have a few—like, be really curious, be interesting—everything isn’t about, like, oh—like, what are you thinking about marriage—oh—like, do you want to have kids—oh, tell me about your last relationship—it’s, like, why don’t we be friends first—because then there’s a high likelihood that if it doesn’t work out, you’re, like, I really like this person and so much too—like, I mean, the people you’re meeting and dating, there’s probably great people in their life too, right—so then if you’re a friend to them, you’re probably going to make other good friends too because you’re probably going on dates with people that, you know, align with—you have similar values and whatnot—as long as you’re kind of screening people ahead of time—so I think just, like, taking the approach of it doesn’t need to immediately be this romantic—like, can I go on a date, and then can we start dating—and then, like, you know, you’re kind of thinking so many steps into the future instead of, like, let’s just see if we, like, connect on a friend level because that’s probably going to lead to a better relationship anyway.

Andrew Namanny: That’s beautifully said, Noah—cold outreach—yeah, my nemesis—talk to me about it.

Noah Berkson: I love cold outreach.

Andrew Namanny: You are a psycho.

Noah Berkson: If there’s one superpower I have, it’s cold outreach—I think as a rule of thumb, as people move up in their career—get more successful—they do less cold outreach because it becomes more of an ego thing where there’s, like, the necessity of cold outreach right when you’re early on because you just need to meet people, and you need to get in front of them—and then there’s, like, the ego thing of, like, well, why do I have to reach out to this person—I have a tendency to do cold outreach, especially to people on podcasts—when I listen to a podcast, and I say, oh, that person was really interesting, I like to do cold outreach to them—and let me give you a couple—let me give you a couple examples of this that were fun—one, there’s a guy—Cal Fussman—Cal is a very famous reporter—he worked for Esquire magazine.

Andrew Namanny: He’s a legend.

Noah Berkson: He’s a legend—and he’s interviewed pretty much every world leader—you know, important political figure, athlete, celebrity, et cetera over the years—and I heard him on Tim Ferriss—he had a couple—he had a couple episodes—I think it was the first one he did—it was, like, a three-hour podcast—and it really inspired me—genuinely inspired me—and I was, like, he is so interesting—and granted, I got what I needed from the podcast—like, I didn’t—I didn’t need him to—I didn’t need any more insight from him—like, I got what I needed, but I was, like, he’d be a great person to know—reached out to him and said, hey, loved your podcast—like, this was great—I saw you lived in LA, and I was living in Chicago at the time—I said, hey, I’m gonna be in LA next Wednesday—I would love to take you to breakfast—and, you know, clear action—like, clear—hey, I was really inspired—I loved this—I would love to get together—I’d love to take you to breakfast if you’re around next Wednesday—I’m in town—he wrote me back, said, oh, that would be so great—like, you know, thank you so much for the kind words—like, you know, I’d love to—I was, like, all right, great—gotta book a plane ticket to go to LA now—next Wednesday—because you—

I dive deeper into the human skills that set people apart in my article on The Human Skills That Make Us Irreplaceable in the Age of AI.

Andrew Namanny: Weren’t actually gonna be in LA.

Noah Berkson: I wasn’t gonna be in LA.

Andrew Namanny: You were bluffing.

Noah Berkson: Bluffing—yeah, but I think there’s so much power in saying you’re going to be in the area where somebody is that will make them say, oh, okay, well, I’ll—you know, if you’re gonna be here those dates—right—then I can get together with you—as opposed to, you live in the city I am—and then it’s easy to kind of, like, throw things off and be, like, ah—like, let’s do it in the future—and as opposed to, I’m going to be there this time—yeah.

Andrew Namanny: How’d you get his email—online?

Noah Berkson: Yeah—I mean, most people’s emails are online—you can find it—or—I mean, I try—I’ll try variations of people’s emails—sometimes just guess—but we have breakfast—have a great—you know, have a great conversation—really, really cool—and a couple years—and we keep in touch—right—couple years later—I’m in—I’m in Charlotte, North Carolina—I’m actually there—Cal has moved there, and I know that—and I messaged him and said, hey, I’m going to be in Charlotte—like, would love to get together—and he’s, like, yeah—he’s, like, let’s—let’s do dinner—like, let’s do dinner—I don’t know—one of the nights we were there—it was—I think it was the night before Thanksgiving—and we had—go have dinner and have a really nice time—have a great time—and he goes, what are you doing tomorrow for Thanksgiving—I was, like, oh, my girlfriend and I—we don’t have any plans—we’re just—we’re just kind of hanging out, taking it easy—he’s, like, oh—he’s, like, we’re having people over—like, you gotta come join us for Thanksgiving—okay, great—yeah—I figure you’re having a party—there’s probably a lot of people—we go there the next day, and it’s his family and us—and it was an amazing Thanksgiving—he has an incredible family—Cal’s incredible—like, it’s the funnest time—but you think—like, this relationship was made possible because I sent you a cold email, right—then flew across the country to have breakfast with you, and now I’m sitting in your home for a very intimate thing for Thanksgiving.

Andrew Namanny: You are a master at this, brother.

Noah Berkson: That’s amazing—that’s an amazing relationship—but that would never happen if not being proactive—being able to kind of put an ego aside and reach out to people—I mean, another great example is Jess, who I host the podcast and events with—another person who I listened to on a podcast—said, wow, she sounds really, really interesting—reach out to her—you know, cold—email her—say, hey—like, I know you live in—I know you live in LA—I’d love to—love to get together for—you know, coffee, dinner, whatever—let me know—like, let me know time and place—and she goes, yeah, follow up with me in—I don’t know—like, two months—and a lot of times when people say that, you’ll go, I’m never going to follow up with that person—right—like, you just forget, or you kind of take it as that person probably doesn’t want to hang out with me—right—so I put it on my calendar, and I’m, like, two months—yeah—to the day—like, get the calendar—hey—like, you mentioned—like, let’s get—you know, let’s get together—and then we get together—get along super well—now—you know, somebody that I host a podcast with and host events with—so I think there’s so much power in kind of curating the people in your life and not kind of letting—not just letting proximity be the thing that determines the people in your life and the network you have.

Andrew Namanny: Do you think it’s important to live in a major hub if you want to build a network?

Noah Berkson: I think when you’re young, proximity is everything because I think it’s being in the right rooms—and that comes with—like we were saying—being in the right—going to the right happy hours, the right networking events—all these things—those are happening in major hubs—and your probability when you’re going to those of meeting really interesting people is going to be much better in the hubs—I do think, though, there was a Chris Sacca who’s, like—so another Tim Ferriss episode—

Andrew Namanny: Another Tim Ferriss episode—2015—that changed my life.

Noah Berkson: Incredible guy—but something he said really resonated with me—which he was, like—he was being asked—he’s, like, is there anything you did early on in your career that really changed the trajectory of your career—and he’s, like, when I was in the prime of my career—living in San Francisco—all my work is in—all my work is in the Bay—all the companies I’m investing in are in the Bay—like, everything is there—he’s, like, I decided to move to Tahoe—like, you’re, like, well, why would you move out of the place where, like, everything is happening—he’s, like, because what I realized is when I was in that hub—right—based on now where I was in my career—he’s, like, I was going to—like, I’d get invited to dinners, and I’d go—just because I got invited—do I really want to be there—probably not—but, like, I got invited, so I don’t want to say no—I’m going to happy hours—I’m taking meetings all the time because people are just, like, hey, can you get coffee—and I’m, like, oh, yeah, I could get coffee—not—because that’s really what I should be focusing on—he’s, like, so we moved my family out to Tahoe, and we said, hey, we’re going to just focus on the people we really want to get to know, and we’re going to invite them to come to us—and so instead of, like, the coffee meeting that I’m doing or going to the dinner—I’m going to only be with people that I invite to come stay at my home for—like, a weekend or a week—and I’m going to get really quality time with them—I’m going to build really deep relationships—and I think now there’s so much value in that because also—like, you can meet somebody—you know, you can have coffee with somebody five times, or you can have them come to your—you know, come stay at your home for a weekend and go skiing and bond together—and that’s going to be a very different relationship—and it gives you the easy—like, it’s an easy way to say no—because I think there’s so much power in saying no—but it’s—it also comes at—like, it comes at an expense.

Andrew Namanny: It’s real—yeah, that’s very real—I love Chris Sacca—that intentional approach—what was it about Jess that inspired you to reach out—you listen to a lot of podcasts, right—so what was it about her specifically?

Noah Berkson: You know, I think with Jess, it was—there’s something that actually she talked about that resonates in this answer—which is, like, what’s your X factor—like, what’s the thing—because I think once you’re—you have some level of success—it kind of becomes, like, success is table stakes—so when you’re—you know, when you’re introducing someone—it’s, like, oh, you both—I don’t know—started a business—run a business—sold a business—whatever it is—cool—that doesn’t really give me the—like, why I want to hang out with this person—and so with Jess, it was, like, oh, what are the other things that are really interesting—she’s, like, oh, I have my pilot’s license—I fly a plane—interesting—not tons of women who are flying their own plane—I host a Burning Man camp—I DJ in my spare time because I just think it’s fun to do that—and I’m doing all this cool stuff on the business side—but I think it’s, like, that X factor—that was, like, oh, this is a really interesting—like, immediately that’s a really interesting person—that’s a—if somebody email intros me and says, oh, this person is—this person is whatever—they’re successful in business—they do this—but they also do this and this and this—and I’m, like, oh, I want to—like, I want to meet that person—that’s an easy intro every time—yes—I think that’s also something that people should think about—and granted, I didn’t—I was not thinking about this when I was younger—but, like, what is your X factor—why are you interesting?

Andrew Namanny: We’re going to play a game, Noah—are you ready?

Noah Berkson: We’re going to play.

Andrew Namanny: This is the first time this game has been played on Permission to Shine—so buckle up, ladies and gentlemen.

Noah Berkson: I feel honored.

Andrew Namanny: Shine or decline—shine meaning yes, you would do it—decline meaning no, you would not do it.

Noah Berkson: Do you want context?

Andrew Namanny: I do.

Noah Berkson: Okay.

Andrew Namanny: Quickly though.

Noah Berkson: Yeah.

Andrew Namanny: You can instantly become best friends with any one person in the world—dead or alive—but you have to completely cut off one of your current closest friends to make it happen—shine or decline?

Noah Berkson: I would decline—reason being, I think right now the friends in my life are so curated, and the friendships are so deep that there’s nobody that I—there’s nobody that would be worth it to cut the friends that I have out of my life.

Andrew Namanny: You’re offered a one-way ticket to Mars to help build the first human colony—you’ll be a legend, but there’s no guarantee you’ll ever come back.

Noah Berkson: I’m gonna stay—I have a really good life right now—I really enjoy my life—um, it’s—it’s—it’s going in a really good direction—so I think I’m—I think I’m staying—I’m going to decline that—you get—

Andrew Namanny: You’re invited to an ultra-exclusive retreat where every guest is a world-class entrepreneur, artist, or leader—but the catch is you have to introduce yourself with a five-minute stand-up comedy routine where you’re going to bomb.

Noah Berkson: I think I shine on that one because I think vulnerability is so underrated—like, the respect people have when someone is vulnerable—whether that’s, like, them making a mistake—doing something stupid—like, looking—you know, looking dumb in front of them—I think people really appreciate that when people are open and willing to do that—so I—I think you’d make a ton of friends that way.

Andrew Namanny: I love that—for people who want to meet interesting people—you said proximity matters—where should these people hang out?

Noah Berkson: I think—I think there’s two pieces of this—you want to—one, you want to hang out where the people that you want to meet are going to be hanging out—I think that a lot of times people use—they go, oh, I want to go to these big conferences or networking events because that’s where I’m going to meet these people—I think that’s completely wrong—I think your probability in these large gatherings of actually meeting anyone that is—meeting the people that you want to meet—there is very little—and people’s attention is not on you—people’s attention is on a million things—and so it’s really hard to get that attention and build a relationship—I think where the future is heading is towards much smaller, more intimate gatherings where you’re able to actually go deep with people and really connect and spend time—and so I’d look at, like, what are some—what are groups that are doing very small events—dinners where you have a very small and select group of people—but steer away from the large-scale events and really go towards the small, curated, invite-only.

Andrew Namanny: I love that—you’re in YPO, correct?

Noah Berkson: Yeah.

Andrew Namanny: How’s that been, and what is it—explain that if people don’t know what it is.

Noah Berkson: YPO is Young Presidents’ Organization—it’s for CEOs of companies—it’s—you kind of think of it like therapy for—therapy for entrepreneurs and CEOs where you—it’s a—it’s a global network—I think there’s probably—I don’t know—30,000 people that are in it around the globe—in every country—but it’s—it’s a group that binds you together with all these people you meet with—you have what’s called a forum—you meet once a month—generally, there’s eight of you in a forum, and you go through all the personal and business challenges in a place where there’s no worry of repercussion—everything that’s talked about stays there—never leaves—and you’re able to have this brutal honesty that frankly, before most people join YPO, they’ve never been this honest in their entire life—it’s a place where they do this thing called the 5%, and you need to do your 5%—which is the 5%—like, the thing that’s so deep down that you don’t talk about—you don’t talk about it to your best friend—you don’t talk about it to your spouse or wife or husband—significant other—you don’t talk about this anywhere—but you’re going to bring it here, and you’re going to have all of these other people that have probably similar experiences—very diverse groups—but are going to have similar experiences—are going to be able to give you experience shares—like, I can’t tell you how—how impactful this has been on my life and career.

Andrew Namanny: It’s got to be the most highly curated group of people that I’ve seen in a group—so kudos to you for being a part of it.

Noah Berkson: It’s a great—yeah—I mean, it’s an—it’s an incredible network—well, I think one of the most powerful things of it is just that you can reach out to anybody in YPO, and there’s just an—there’s a rule—actually, I was going to say it’s an unwritten rule—it actually is a rule—that they will get back to you within 24 hours—so I could write anyone—could be CEO of a public company—could be—you know, founder—some huge business—whatever it is—they’ll get back to me—and I think there’s just—that’s really nice to have because now it’s, like, anyone you want to meet, you can meet them.

Andrew Namanny: You have access, right?

Noah Berkson: You have access—and I think access is everything.

Andrew Namanny: Noah, thank you for being here—thanks for sharing your knowledge on how to make cool friends—I think you’re such an example of giving more than you take, which I think is such an important principle to live by—and I really appreciate you stopping by the studio to share your knowledge.

Noah Berkson: I appreciate—Andrew—this was awesome.

Andrew Namanny: Yeah, man—everyone go check out Dose of Greatness—your podcast with Jess Ma—and I can’t speak highly enough about Outcove Valley—getting to hang with 65 of the most incredible entrepreneurs in Park City just a few weeks ago—it blew my mind, man—so highly recommend that to anybody who gets a chance to go—do not hesitate.

Noah Berkson: We were so happy to have you there—I think we’re going to do the next one—it’s looking like October 2nd to 5th in Hawaii.

Andrew Namanny: Amazing—all right, man, we’ll see you there, brother.

Noah Berkson: That’s it.
Andrew Namanny: Thank you so much for tuning in to Permission to Shine—the podcast dedicated to sharing the most humble, inspiring stories that I know you will love—again, this is Andrew Namanny—I appreciate you tuning in as always—please, please reach out—please follow on Instagram, on YouTube, on LinkedIn, Spotify, Apple—leave us your thoughts—let us know who you want as a future guest or what your takeaways are from this conversation—we’ll talk to you soon—have a great, great week.

The conference

Jess Mah and I started talking about this idea 6 months ago with a "what if we could bring incredible people together in an intimate way, where everyone is top-tier, can be vulnerable without judgement, build deep & lifelong friendships and nobody is trying to sell anyone anything?"

It's been incredibly fulfilling to see it come to life.

The connection and soft skills that emerge from Outcove are what I explore in The Human Skills That Make Us Irreplaceable.

What Made It Different From Other Conferences

No panels. No keynotes. No one pitching from a stage.

Just 70 people who earned their way into the room, spending real time together. Hiking. Sitting around fires. Sharing things they wouldn't say at a standard networking event.

The format was intentional. When you remove the transactional layer from a gathering, something changes. People stop performing and start connecting. The conversations that emerged over dinner were the kind that typically take years of a friendship to unlock.

That's the whole premise: create the conditions where real connection can happen fast. Most events optimize for scale. We optimized for depth.

What I Took Away

A few things stayed with me after the weekend.

First: the most valuable conversations happened in the margins. Not on the scheduled hikes, but in the five minutes before dinner, or the late-night conversations that went until 2am. You can't plan those. You can only create the space for them.

Second: vulnerability is contagious in the best way. One person goes first. Then another. Within a few hours, the entire room is operating at a level of honesty that most professional relationships never reach.

Third: the right 70 people in the right setting will do more for each other than any formal accelerator or mentorship program. Peer relationships at this level aren't just motivating. They change the ceiling on what you think is possible.

We're already building the next one.

I’ll tell you why this is crazy, what I loved about his letter, and a little about the firm.

Who is Nate Anderson and Hindenburg Research?

Nate Anderson is the Founder of Hindenburg Research, and his track record speaks for itself.

This guy single-handedly:

• Wiped $153B in market value from Guatam Adani
• Wiped $B's from Nikola Motors
• Wiped $B's from Carl Icahn
• Wiped $B's from Clover Health

Read his farewell letter here—it reminded me of Michael Burry's letter to his investors after the 2008 crash.

A few of my favorite lines:

Starting From Zero

“When I started this, I doubted I was capable. I didn't have a traditional finance background. None of my relatives are in this field. I went to a state school. I'm not a slick salesperson. I don't know any of the right clothes to wear. I can't play golf. I'm not some superhuman that can function on 4 hours of sleep. In most of my jobs I was a good worker but mostly looked over. I had no money when I started—and after catching 3 lawsuits immediately out of the gate, I quickly had less than no money.”

It's refreshing to see someone acknowledge their unconventional path.

Building a Dream Team

“One at a time, and without a clear plan, we built a team of 11 incredible people. I hired each of them not because we needed workers, but because when our paths crossed, and I could see who they were, I realized it was madness not to bring them on.”

When you find people who share your vision and values, everything else can be learned.

Powerful Reflection on Success

“Someone once told me that at a certain point, a successful career becomes a selfish act. Early on, I felt I needed to prove some things to myself. I have now finally found some comfort with myself, probably for the first time in my life. I probably could have had it all along had I let myself, but I needed to put myself through a bit of hell first. The intensity and focus has come at the cost of missing a lot of the rest of the world and the people I care about. I now view Hindenburg as a chapter in my life, not a central thing that defines me.”

His journey from seeking external validation to finding inner peace mirrors what many entrepreneurs face but rarely discuss openly.

I explore the different perspectives of founders and investors in Investor vs. Founder.

Conclusion

It’s Incredible to see someone with no traditional finance background make such an impact.

Goes to show that sometimes being an outsider gives you the exact perspective needed to spot what others miss.

What's even more inspiring is how he's choosing to walk away at his peak.

Follow me on LinkedIn for more content like this.

No story exemplifies this better than Squid Game, a series that transformed from a repeatedly rejected concept into a global phenomenon.

This is the story of how creator Hwang Dong-Hyuk turned a $21.4 million investment into a billion-dollar franchise through sheer persistence and unwavering vision.

Here’s how it went:

Years of Rejection

Growing up in a working-class family in Seoul, Hwang Dong-Hyuk witnessed firsthand the stark inequality in South Korean society.

He saw his neighbors and friends struggling with debt, desperately searching for ways to escape their financial burdens.

These experiences would later become the foundation for Squid Game.

From 2009 to 2019, Hwang pitched his concept to almost every Korean studio, facing constant rejection.

Studios claimed the show was,

“too difficult to understand, too bizarre, too violent.”

Yet despite the endless stream of rejections, Hwang remained determined.

Netflix Opportunity

In 2018, Netflix co-CEO Ted Sarandos expressed his desire to discover international hits.

He said,

“The exciting thing for me would be if the next Stranger Things came from outside America. Right now, historically, nothing of that scale has ever come from anywhere but Hollywood.”

This created the perfect opportunity for Hwang.

Netflix agreed to fund the project with a modest budget of $21.4 million – a relatively small amount for a Netflix production.

Challenging Production

Production began in 2020, perhaps the most challenging year to film due to the global pandemic.

The stress of production took a significant toll on Hwang, who lost six teeth during filming.

Unprecedented Success

On September 17, 2021, Squid Game was released to the world.

The show's popularity exploded almost immediately.

Within four weeks, it had reached #1 in 94 countries.

The numbers tell an extraordinary story of success:

• Season 1 generated over $900 million in revenue.
• The show achieved venture-scale returns with a 42x return on investment.
• Viewers streamed Season 1 for over 2.2 billion hours.
• Season 2 is projected to generate over $1 billion in revenue.

Power of Persistence

Hwang's journey from rejection to global success demonstrates the power of persistence.

I share more about what captures my attention on my Now page.

Despite a decade of setbacks, he never abandoned his vision.

His story transformed from a repeatedly rejected concept into Netflix's most-watched show in history.

This proves that sometimes the most revolutionary ideas just need the right opportunity to shine.

Conclusion

Squid Game's success represents more than just entertainment industry metrics.

It demonstrates how authentic storytelling, rooted in real social issues, can resonate globally.

Hwang's decade-long journey reminds us that breakthrough success often requires unwavering dedication, even when faced with countless rejections.

As Season 2 approaches with its billion-dollar projections, Squid Game stands as a testament to the power of believing in your vision, no matter how bizarre others might find it.

Follow me on LinkedIn for more content like this.

I wanted to meet Cal and thank him for sharing his stories. We got the opportunity to have breakfast in early 2020. We became fast friends and even shared Thanksgiving together a couple years back.

Picture of me and Cal Fussman

I share this to show how the most unlikely connections can result in the most fulfilling relationships.

Conversations like these inspire the communities I'm building. Learn more on my Now page.

What I Learned From Watching a Master

Cal spent decades as a journalist interviewing everyone from Muhammad Ali to Mikhail Gorbachev. His gift isn't knowledge. It's questions.

What I noticed over breakfast was that he never asked a question he already knew the answer to. Every question was genuinely open. He wasn't steering the conversation toward a destination. He was exploring.

Most people ask questions to confirm what they already think. Cal asks questions to find out something he doesn't know. That distinction changes everything about what comes back.

I've tried to apply that ever since, in investor meetings, in first conversations with founders, in pretty much any room where the instinct is to perform instead of listen.

How It Changed How I Meet People

Before I met Cal, I would go into meetings with an agenda. A list of things I wanted to cover. A version of the conversation I was already running in my head.

After spending time with him, I started showing up differently. Fewer prepared questions. More genuine curiosity about what this specific person has seen that I haven't.

The conversations got better immediately. Deals moved faster. Relationships went deeper.

The simplest thing I took from Cal: ask the question you're actually curious about, not the one that makes you sound smart. The real question usually leads somewhere the other person has never gone before.

And that's where the best conversations start.

I know that's not the answer people expect. They want to hear about product-market fit, raising a seed round, or finding a technical co-founder. But none of that matters if you can't sell. And most people can't sell because they've never been told no 200 times in a single day.

Video

https://noahberkson.com/wp-content/uploads/sites/100/2024/10/1727196150543.mp4

Why Door-to-Door Is the Best Entrepreneurship Training

Selling security systems door to door was one of the most formative experiences of my life. You knock on a stranger's door. They didn't ask you to come. They don't want to talk to you. And your job is to turn that into a conversation, then into a sale.

Most doors close in your face. Some people are rude about it. Some are polite. A few actually listen.

After a few weeks of this, cold calls feel like the minor leagues. Walking into a room full of investors feels manageable. Getting rejected by a customer doesn't sting the same way. You've already heard no in every possible tone of voice, from every type of person, in every kind of weather.

That's the training. You can't replicate it in a classroom.

What It Actually Teaches You

Rejection is information, not failure. Every no tells you something. The way someone says no, what they say before they say it, what objection they raise first. You start pattern-matching. You get better.

The pitch is not the product. The product can be great. If you can't communicate why it matters in 30 seconds, you're done. Door-to-door forces you to find the shortest path from introduction to value.

Persistence compounds. The people who quit after 20 rejections never find out that number 21 would have said yes. Showing up consistently, even when it's not working, is a skill. It's trainable.

People buy from people they trust. Not products, not features, not pricing. The fastest way to get someone to trust you is to be honest, be direct, and actually listen to what they say. That's as true in a boardroom as it is on a doorstep.

You Don't Have to Sell Security Systems

The specific product doesn't matter. What matters is putting yourself in a situation where you have to convince a stranger to give you their time and money, with no warm intro and no safety net.

Sell solar panels. Sell subscriptions. Sell handmade candles at a farmers market. The environment is the training, not the product.

Most first-time founders have a product problem or a team problem. But more often than they realize, they have a sales problem. They don't know how to ask for the close. They get uncomfortable when there's silence. They give up on a conversation too early.

All of that goes away when you've knocked on 500 doors.

The bottom line? You can learn a lot from books, podcasts, and mentors. But nothing replaces the experience of being told no to your face and choosing to knock on the next door anyway. That's where entrepreneurs are made.

Go sell something. Start today.

Owning professional sports teams was a big topic of conversation.

Sports team valuations are continuing to skyrocket due to a few factors. I think the biggest however is that there aren't enough professional teams for the amount of billionaires that want them.

Take Josh Harris, Co-Founder of Apollo Global Management who bought the Washington Commanders for $6B last year. It was the highest price ever paid for a sports team and $1.35B higher than the Denver Broncos were bought for a year earlier.

I explore more about what I'm investing in on my Now page.

With the new league ruling allowing PE firms to own up to 10% of NFL teams, I think we will see valuations continue to climb. You'll also see family offices pouring into PE funds focused on sports.

Why Ultra-High-Net-Worth Families Are Buying Teams

It's not just about prestige, though that's part of it. There are real structural reasons why sports teams have become the asset class of choice for the ultra-wealthy.

First: supply is permanently constrained. There are 32 NFL teams. That number isn't going up. As the pool of people who can afford to buy grows, the number of available teams doesn't. Basic economics pushes prices in one direction.

Second: media rights keep expanding. The NFL's latest TV deal was worth $113B over 11 years. As streaming platforms compete for live sports rights, that number will grow. Team owners participate in every dollar of that upside.

Third: depreciation rules. Under IRS guidelines, owners can depreciate the value of player contracts as an intangible asset. For a $6B team purchase, that's a significant annual tax benefit. At the highest income levels, the tax efficiency alone makes the math compelling.

What This Signals About Where Capital Is Going

The conversations at that conference pointed to something broader than sports.

Ultra-high-net-worth families are increasingly moving toward what I'd call trophy assets: things that are scarce by design, culturally significant, and appreciating faster than traditional stores of value. Sports teams. Landmark real estate. Art. Early-stage stakes in transformative companies.

The common thread is scarcity. You can print more bonds. You can't create more NFL franchises.

For those of us not buying teams outright, the PE fund route is worth watching. Partial ownership vehicles are already emerging, and the early movers into sports-focused funds will likely see meaningful appreciation as the asset class matures.

The question isn't whether sports team valuations will keep climbing. It's who gets access to the upside as they do.

They're wrong. Youth is one of the biggest advantages in business. And most young people waste it because nobody told them how to use it.

Why Experienced People Help Young Founders

Here's something I noticed early in my career. When I was 22 and reaching out to successful people for advice, I got responses. Real ones. From people who were genuinely busy and selective with their time.

That didn't make sense to me at first. I had nothing to offer them. No track record, no network, no capital. Why were they taking my calls?

The answer took me a while to figure out. They helped because they didn't see me as a threat.

When a peer asks for advice, there's a subtle competition at play. They might take your idea. They might outperform you. They want something that puts them in a better position relative to you. The help comes with friction.

When someone significantly younger asks for advice, none of that applies. They just want to learn. Helping them costs nothing and feels good. Most successful people became successful partly because someone helped them early. They want to pay that forward.

That window doesn't stay open forever. Use it while you have it.

How to Actually Activate This Advantage

Knowing you have an advantage and knowing how to use it are different things. Here's what I've seen work:

Be specific about what you're asking. "Can I pick your brain?" is a waste of everyone's time. "I'm working on X problem and I'd love 20 minutes to ask about your experience with Y" gets answers. Specificity signals that you've already done work.

Do the research before you reach out. Know who you're talking to. Know what they've built. Know what's publicly available about their thinking. The conversation you have after you've done that homework is ten times more valuable than a cold cold ask.

Make it easy to say yes. Short emails. Clear ask. Offer to come to them, do it by phone, make it 15 minutes. Every friction point you remove increases the odds they actually respond.

Follow through and report back. This is the step most people skip. After someone gives you advice, tell them what you did with it. Tell them what happened. That closes the loop and builds a real relationship. Most people who ask for advice never do this. It's an easy way to stand out.

The Expiration Date

This advantage has a shelf life. By your late 20s, people start expecting you to have figured some things out. By your mid-30s, the "young founder" card doesn't carry the same weight.

That's not a problem. If you used the window well, you've built real relationships, real skills, and real track record. You don't need the shortcut anymore.

But you have to use it while it's there. The people who understand this early build networks in their 20s that they spend the rest of their careers drawing on.

The bottom line? Inexperience is only a liability if you treat it like one. If you treat it as a reason to learn aggressively and reach out honestly, it becomes one of your best assets. People want to help people who are earlier in the journey than they are.

Go ask for the help. Do it now, while the window is open.

A few takeaways:

Something he said that stuck with me was "My goal is to be respected by the 25th century." Very few people think more than 12 months ahead. I'm wondering what life and innovation would look like if more people thought this way.

His body is currently aging roughly 7 months for every 12 months of time. I assume this will keep going down. Could this theoretically double the human life span if done from a young age?

Continuous learning is central to the human skills I discuss in The Human Skills That Make Us Irreplaceable.

When asked what age he believes he will live until, Bryan replies "I'm guaranteed to die in the most ironic way possible."

Most people do everything they can to avoid negative press, Bryan thrives on it. He's found a way to convert it into an unstoppable energy.

Why This One Hit Different

I've sat in a lot of founder sessions. Most of them are about tactics. This one felt different because Bryan operates from a completely different time scale than anyone else I've encountered.

When he said "respected by the 25th century," the room went quiet. Not because it was a strange thing to say, but because it forced everyone to confront how short their own horizon was.

Most of us are optimizing for the next quarter, the next raise, the next product launch. Bryan is asking: what would I need to be doing right now to matter 800 years from now? That's not a question with a practical answer. It's a question that changes how you think.

The contrast is striking. The person next to you is worried about Q3. Bryan Johnson is worried about the 2200s.

What I'm Applying

I've started asking a simpler version of his question: would I be proud of this decision in 20 years?

Not 800. Just 20.

It's surprising how much that shifts the calculus. Short-term tradeoffs that feel necessary often look different against a longer backdrop. Deals that seem attractive today look costly when you project them forward.

And the things I tend to deprioritize — health, relationships, learning without an immediate ROI — look very different when you zoom out.

Bryan's framework is extreme. But it points at something real: the people who build things that last are almost always playing a longer game than everyone around them.

But many, like myself have had a struggle with being vocally vulnerable with those around us, closest to us, and especially the outside world. We don't let our vulnerability show because historically and societally, it's been widely acknowledged as a sign of weakness and even self-doubt.

Because of the uncertainty in our lives and businesses, we try to balance that uncertainty by vocally over-compensating our certainty in other areas.

We feel the need to let people know that everything in our lives and business is going great. We have so much momentum, a new partnership that will change everything, a big investment right around the corner and the list goes on. We outwardly project this even if things are very much not okay. Even when we are in loads of credit card debt, worried about missing payroll, unable to pay back student loans, about to be evicted from our home or ruining our most important relationships because we can't handle the stress and are on a short fuse.

I've lived this and understand the mindset behind it. I would think, "who is going to want to invest in me, believe in me or even work for me if I can't be seen as the strong figure at the helm who just keeps marching despite what I may be going through."

What I've realized, now being on the other side of the table as an investor, is that vulnerability in a founder is one of the biggest advantages and indicators of future success. Any time you're being pitched, you're only seeing the "Instagram" version of that founder, not who they truly are. Taking the time to understand their personal lives, struggles, motivations and what they have sacrificed to be here today.

Through years of self reflection, amazing organizations like Entrepreneurs Organization, and therapy, I've begun to feel more comfortable sharing my vulnerability with those closest to me and now, to the outside world.

I did an exercise last year on vulnerability asking myself the question "Who is Noah?" where I wrote down a number of declarative statements about myself which I've shared here:

I am confident I’m overly optimistic, many times to my detriment I let people into my business life too easily and my personal I make too difficult I’m guarded from being burned in the past I at times can be a pleaser and feel a need to make everyone feel included in a conversation I need things to be tidy I’m a routine freak and when out of one feel uneasy quickly I care too much about what other people think I’m a healthy eater I care too much about outward appearances I don’t take enough time to enjoy the small things I get energy from people but am becoming an increasing introvert I love to read and find comfort in books I need exercise to function I am chronically underprepared and find satisfaction in my ability to wing it I set high expectations and at times force things unnaturally to make them come true I used to give people the benefit of the doubt but increasingly assume the worst I don’t let my outer emotions show and instead cope with them internally I measure my self worth too often from business success

This post in itself is a challenge of vulnerability for me. Five years ago, I never would have guessed that I would be speaking to you all like I am today, but through years of effort and practice I am beginning to find comfort in my vulnerability. My hope is that it's contagious.

I’ve written more about bringing people together in authentic settings in my piece on Outcove.

How can you be more vulnerable this year?

Every year, 26 of our friends gather for a weekend we call Weekend of Man. It's summercamp for adults, and it's one of the most important things I do all year.

Not the most fun thing. The most important thing. There's a difference.

What Actually Happens

We play paintball, pickleball, basketball, and bags. There's paddleboard jousting. We eat nothing but meat. We sit around a bonfire at night and actually talk to each other, without phones, without an agenda, without the usual social performance that comes with most gatherings.

The competitions are real. People take them seriously. There's a scoreboard. There are winners and losers. And somehow, that combination of physical challenge, shared discomfort, and low-stakes competition produces something that a dinner party or a conference never does.

It produces actual friendship.

Why Adults Need This

At some point in your 20s, friendships stop forming the way they did in school. You don't have the built-in repetition of seeing the same people every day. You don't have shared adversity. You don't have time.

What you have are dinners, drinks, and catch-up calls. Those are fine. But they don't create the depth that comes from doing something hard together.

Research on bonding consistently points to shared experience, especially experiences that involve some element of challenge or vulnerability, as the fastest way to build real connection. It's why military units become like families. It's why people who went through difficult things together stay close for decades.

Weekend of Man is a manufactured version of that. We engineer the conditions for real friendship: physical challenge, shared meals, time away from normal life, no distractions.

It works.

The Real Return

Here's what you can't put a number on. The 26 people who come every year are also the people I call when I'm making a hard decision. The people who show up when something goes wrong. The people who know me outside of whatever professional context we might share.

That's not something you can build at a networking event. You can't schedule it into a quarterly offsite. It has to be earned through time spent together doing things that actually matter.

I've started several businesses, built communities of thousands, and had more dinners and coffees than I can count. The relationships I value most didn't come from any of that. They came from weekends like this one.

Starting Your Own

You don't need 175 acres or $6,000 of fireworks. You need a group of people, a shared activity, and enough time away from normal life for something real to happen.

A camping trip. A ski weekend. A fishing trip. It doesn't matter what you do. What matters is removing people from their routines, putting them in a shared environment, and letting the hours pass without an agenda.

The bottom line? The adult friendships worth having don't happen by accident. You have to create the conditions for them. A weekend like this is how you do it.

Find your 26 people. Build your weekend. Do it every year.

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Give it a watch here: https://www.youtube.com/watch?v=hAfVoOE2t44

1. The Billionaire You Have Never Heard Of
2. From Bankrupt Mine to Billion Dollar Defense Asset
3. James Litinsky Built America's Rare Earth Empire

This guy is worth over one billion dollars and controls one of the most vital companies in America but you have probably never heard his name.

A hedge fund guy walks into a bankrupt mine and walks out building the only end-to-end rare earth magnet supply chain in the Western Hemisphere.

That is the James Litinsky story.

The Opportunity

Most investors saw the collapse of Molycorp as a warning sign.

Litinsky saw a once-in-a-generation opportunity.

He took a failed mine in the Mojave Desert and rebuilt it into MP Materials: the only Western company that can take rare earths from rock to refined materials to finished magnets.

Why It Matters

That capability matters more than most people realize.

Magnets power:

• EVs
• Wind turbines
• Drones
• Fighter jets
• Missile guidance systems

It is so vital that the United States Department of Defense has invested over four hundred million dollars into the company to secure this supply chain for national defense.

Strategic Importance

While the world was fixated on software and SaaS multiples, Litinsky quietly rebuilt one of the most strategically important industries on Earth.

Not many entrepreneurs can say they revived an entire supply chain.

Even fewer can say the Pentagon calls their business vital.

James Litinsky can.

Conclusion

Litinsky turned a bankrupt mine into a billion dollar strategic asset that powers everything from electric vehicles to fighter jets. He built the only complete rare earth magnet supply chain in the Western world while most investors were chasing software companies.

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1. AI Is Not Taking Your Job—Yet
2. The Real Reason 153,000 Jobs Were Cut
3. Why Companies Are Firing People for AI

The headlines are brutal.

153,000 jobs were cut in October.

The highest October job losses in 20 years.

Three times more than October 2024.

And the easy narrative is to blame AI.

But that is not what is happening.

The Real Story

AI has not even started replacing people.

Companies are not laying people off because of AI.

They are laying people off to afford AI.

The Economics

The cost of GPUs, infrastructure, and integration is massive.

So executives are being forced to make a brutal choice.

Do we invest in people or in machines?

The Transition

AI is not the job killer.

The transition to AI is.

This is the critical distinction everyone is missing.

The Solution

The companies that figure out how to keep humans in the loop while building AI into the workflow will win this decade.

That is the playbook.

Conclusion

We are living through a transition period, not a replacement period. The companies cutting jobs to fund AI infrastructure are making short term decisions that may cost them long term. The winners will be those who invest in both technology and people.

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I travel a lot, both for work and for adventure. While every trip is unique, there are a few places I return to or that have left an indelible mark.

Here are three destinations that offer the perfect blend of work, inspiration, and escape.

Japan

Every year, I head to Niseko in Japan to snowboard. It’s a non-negotiable trip that serves as a physical and mental reset.

It's my annual pilgrimage for pure, exhilarating fun with other entrepreneur friends.

South Africa

My trip to the Sabi Sabi private game reserve in South Africa was truly incredible.

Spending days on a safari, completely disconnected from the digital world and immersed in nature, is a powerful experience.

Argentina

I travel to Argentina multiple times a year, as it's home to my tech team. While it’s a work trip, it’s also an opportunity to immerse myself in the vibrant culture of Buenos Aires.

Blending strategic work sessions with exploring a different way of life provides a unique kind of energy and inspiration that you can’t get from a Zoom call.

Conclusion

Travel, whether it's for adventure, work, or relaxation, is a crucial investment in yourself.

It breaks routines, sparks new ideas, and provides the perspective needed to tackle big challenges.

Wearing both the founder and investor hats has taught me that success hinges on three things: understanding why most deals fail, respecting timing at every stage, and spotting the subtle signals that say it's time to sell.

Common Obstacles in Early-Stage Investing (and How I Approach Them)

Failure is the default. Roughly nine out of ten companies I see won't make it, so a one-check-a-year hobbyist strategy is just roulette in nicer clothes. Real diversification means writing dozens of checks, not one or two.

Volume isn't enough without patience. New angels sometimes email me asking when to expect dividends; the honest answer is "not this decade." Early-stage companies burn cash for years, and liquidity events—if they come—often land in year ten or fifteen.

It's never about the business model. When you're investing at the formation stage of a company, trying to evaluate the business model makes very little sense. The original pitch rarely survives first contact with the market.

Most startups pivot multiple times before finding a product-market fit. The initial idea investors back almost never resembles the final business that succeeds.

When investing early, you're not underwriting a business model—you're betting on a person.

Expectation-setting matters. I tell founders up front that my capital is personal, not pooled from outside LPs. That aligns us: a 3× return in two years is great for me and life-changing for them.

No one's forced to swing for a mythical 500× home run.

The Importance of Timing in Business: Lessons from My Own Ventures

0 → 1, 1 → 10, 10 → 100 are different sports.

Early on, I thrive on messy discovery; later stages demand forecasting, process, and people management—work that energizes some founders and drains others (myself included).

Knowing which phase excites you keeps both you and the company healthy.Mis-timed valuations kill exits. I've watched friends reject life-changing offers because VCs wanted bigger multiples.

A few years later, those same companies were overpriced, unprofitable, and effectively unsellable. Timing, not just growth, ultimately determines whether you win or lose.

The consequences of missing the right exit window can be brutal.

When companies eventually sell at a significant discount, investors typically recover their money through preference stacks, while founders who spent a decade building might walk away with almost nothing.

Even pocketing a million or two after taxes and years of effort often means they would have been financially better off simply taking a regular job during that time.

Markets move—founders must, too. The most successful companies I've seen weren't those with perfect initial ideas, but those that could pivot quickly when market signals changed.

I back founders who can read the clock and adapt rapidly, even if it means completely transforming their business model.

Knowing When It's Time to Exit Your Business

Energy is my north star. If I'm no longer intellectually lit up by the problems in front of me, it's time to consider selling—no matter what the spreadsheet says. Burning out helps no one.

For me, the decision to exit comes down to two questions:

1. Am I still energized by what I'm doing?
2. Am I working on problems that mentally stimulate me?

As a business scales, the problems you face change dramatically.

In the beginning, you're focused on getting early customers, forming partnerships, and hiring your initial team. Then you shift to managing people (which I personally don't enjoy), building larger teams, and long-term forecasting.

Optionality beats obligation.

Because my investors are…me, I can say yes when a "mere" 10× outcome appears. That flexibility prevents the valuation-creep trap that strands founders on an island of paper riches with zero buyers.

Watch for silent alarms.

Rising customer-acquisition costs, investor misalignment, or a creeping dread of Monday morning all signal it's time to explore exits before the window closes.

I'd rather leave some money on the table than wrestle with a tired company for another five years.

Finding Opportunities in Economic Uncertainty

I've learned that the best investment opportunities often emerge when nobody wants to invest.

Usually, those moments are the most opportune times. It's true in the market too—when everything is in free fall, the people who remain calm and have cash are thinking, "This is the best time ever."

Most people don't think that way.

When investing other people's money, those people often say, "Things aren't going well. I don't want my money going out during such uncertainty." So VCs typically halt capital calls and slow down their investments.

But those are generally the most advantageous times. It's all in retrospect, though.

When people look back five or ten years later, they say, "Yeah, that was the perfect time," or "That was when this business became one of the most important companies in the world, but nobody really believed in it at the time."

Key Takeaways

1. Diversify aggressively—early-stage success is fundamentally a numbers game.
2. Respect the clock—from market cycles to personal motivation, timing rules everything in business.
3. Exit while you still love the chase—passion, not spreadsheets, tells you when it's time to move on.