He Has $70M And Flies His Own Plane Wherever He Wants

Summary

Moneywise Podcast Summary

Episode: "He Has $70M And Flies His Own Plane Wherever He Wants"

Host: Daniel Berk
Guest: John Arrow
Date: April 21, 2026

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Episode Overview

In this episode of Moneywise, Daniel Berk sits down with John Arrow, a founder who bootstrapped his company Mutual Mobile, scaled it to 350 employees, and ultimately sold it for $100 million—$70 million of which went directly to his personal bank account. The conversation explores John’s entrepreneurial journey from childhood hustles to life-changing exits, transparent discussions of wealth and spending, his passion for flying, personal philosophies around money and risk, and his current experimentation at the frontiers of AI. This episode provides a deep and candid look into how a high-net-worth individual thinks, lives, and invests—and what motivates them after achieving financial independence.

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Key Discussion Points & Insights

1. Early Entrepreneurial Spirit & Mindset

• Childhood Hustles: John describes himself as a lifelong entrepreneur, starting with lemonade stands, hot chocolate in winter, and building websites in high school.

  "I learned at a really early age that if you were resourceful and you had grit and you tried to do things, you could make money." — John Arrow [01:21]

• First Tech Wins: Building websites in the Geocities era gave him initial capital. He later developed a software product to help parents monitor children's online activities, inspired by his psychotherapist mother's stories.

  "I made a piece of software that did exactly that and put it out there... before I knew it, it was selling thousand dollars a day every day." — John Arrow [03:17]

• Dot-Com Lessons: Witnessing both the hype and the bust of the dot-com era shaped John’s aversion to smoke-and-mirrors businesses:

  "You didn’t need to go out and create this perception that you were generating value. Just go generate value." — John Arrow [04:15]

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2. Eccentric Habits & Love of Flight

• Aviation & Discipline: John’s passion for flying led to personal habits—staying sober to keep his pilot’s license eligibility, protecting his hearing, and maintaining optionality in life.

  "If I take a sip of alcohol... you have to wait eight hours... I love that option. I kind of approach life in that way, too. Why should you close doors unnecessarily?" — John Arrow [06:19]

• Health & Longevity: Unusual habits like wearing earplugs (and later AirPods) while walking downtown, both for longevity and undistracted thinking.

  "Hearing is a thing that we haven’t figured out how to preserve and protect. So I’m really cautious of that." — John Arrow [06:54]

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3. Wild Stories & Risk-Taking

• Cuba Trip Before Exit: In an iconic story, John and his cofounder left partway through Neville’s 30th birthday trip to Cuba—traveling illegally just before signing their company away for millions.

  "I mean, how fitting was it? We went to the most socialist, communist country right before doing the most capitalistic thing in the world—selling a company." — John Arrow [10:27]

• Approach to Risk: Emphasizes experiencing life fully, even with significant stakes on the line.

  "I was not going to fly my plane to a communist country... It was like getting off a time machine." — John Arrow [09:47]

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4. Value Creation & Creative Problem-Solving

• Cavett: Suing-as-a-Service: John started a company automating small-claims lawsuits, democratizing legal leverage for consumers. Notably helped Neville recover a million Amex points by creatively triggering a response from the company.

  "What I did is I have a service that gives me the email address of everyone at a company... we sent out an email to every single employee at American Express with the subject line 'possible data breach'." — John Arrow [15:55]

• Philosophy: Power comes from being able to take unique, outsized actions that ordinary people can’t or won’t do.

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5. Mutual Mobile: Building & Selling a $100M+ Company

• Origins: Formed at the University of Texas, spotting the iPhone’s world-changing potential.

  "We had the largest number of iOS engineers under one roof outside of Apple for several years." — John Arrow [17:53]

• Strategic Exits:

  • 2013 partial sale at ~$70M valuation, all bootstrapped—John took the majority of his chips off the table (~$70M personally).
  • 2023 secondary exit after returning as CEO; less explosive growth due to market commoditization, but still a positive outcome for all involved.
  • Key Quote:

    "You never regret selling. It’s never happened to me, and I don’t think I know anybody who’s ever regretted selling a company. I've met many people who have regretted not selling." — John Arrow [21:26]

• Personal Impact:

  • "The day after the wires hit, you’re thinking about your bank account balance and it's literally an order of magnitude higher than it was before... it changes your perspective on everything." — John Arrow [22:09]
  • "You never need to work again in your life." [22:35]

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6. Wealth Management, Portfolio, and Philosophy

• Approach: Strong preference for DIY over financial advisors—citing self-reliance and deep familiarity since his teens.

  "It should be your business to kind of understand your own personal finance." — John Arrow [28:53]

• Investment Allocation:

  • Majority in liquid equities (SPY, DOW, Apple, Google, Tesla)
  • Angel investing in "exotic" or high-risk ventures, including SpaceX
  • Real estate: owns condo in Austin, rents in NYC
  • Ongoing experiments and startups

• Personal Spending:

  • Monthly: $50-65k+, comprising $10k HOA/taxes in Austin, $11k rent in NYC, ~$7k/month for airplane fixed/variable costs, $20-30k legal/discretionary
  • Utilizes room service, Air travel weekly, previously kept cars at remote airports for self & pilot network
  • "My goal with investing is it should sustain whatever your spend is in life... ideally, your net worth steadily increases, even without you needing to be dependent on an income source." — John Arrow [42:46]

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7. Assessing Enough: Motivation and Threshold Numbers

• Threshold Number/Financial Indifference:

  • Reached after Mutual exit; “well into the eight figures”—mostly liquid.
  • "There was a moment I think after Mutual where I realized I didn’t need to work again and I kind of tried not working and I realized I just loved building too much." — John Arrow [40:21]

• Money’s Role:

  • "Money is a proxy ... it allows you to do more of what you already want to do." — John Arrow [38:47]
  • "Money makes you more the person you already were." — John Arrow [25:35]

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8. The Age of AI: Freedom GPT and Beyond

• Origin: Frustrated by OpenAI’s limitations, John and his cofounder built Freedom GPT to give users uncensored, multi-model AI access.

  "Let’s just create the place where everybody can go and use whatever AI is objectively best for what they’re trying to do." — John Arrow [37:31]

• Worldview:

  • Saw parallels to digital and banking divides: not everyone would access AI equally.
  • "We want to make that area where people are not left behind and can always use the AI model that’s best for them." — John Arrow [41:35]

• Building for the Future:

  • Ongoing hacking and rapid prototyping, e.g. recent creation: a site (otu.net) that finds unclaimed money and relevant class actions for any name using AI-powered lookups.
  • "Every week now that it’s so easy to create software, I’m starting [a new project]…" [51:13]

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9. Memorable Quotes & Moments

On Wealth and Selling:

• "You never regret selling. I’ve met many people who have regretted not selling." — John Arrow [21:31]

On Living with Options:

• "Why should you close doors unnecessarily?... There is a real cost to options, just like there are derivatives." — John Arrow [06:26]

On Life Philosophy:

• "Money is a proxy... allows you to do more of what you already want to do." — John Arrow [38:47]

On Future Tech:

• "What an amazing time to be alive. And we get to…" — John Arrow [53:19]

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Timestamps by Theme

• Intro & Background: [00:00–03:50]
• Early Entrepreneurship: [01:21–03:50]
• Dot-Com Influence: [03:37–04:44]
• Personality & Flying: [05:02–07:58]
• Wild Life Stories (Cuba, Planes): [08:39–12:12]
• Cavett/Creative Legal Solutions: [12:23–16:13]
• Mutual Mobile Story, Exits, Numbers: [17:43–25:11]
• Life Post-Exit, Wealth Management: [25:24–28:53]
• Investment Philosophy: [28:44–30:01]
• Return as CEO & Second Exit: [30:01–34:03]
• AI, Freedom GPT, New Ventures: [34:57–40:21]
• Philosophy of Money, Thresholds: [38:22–40:21]
• Transparency on Net Worth & Spending: [42:09–47:13]
• Lifestyle, Real Estate, Plane, Cars: [45:26–48:05]
• Purpose, Happiness, Future Plans: [49:07–53:21]
• Closing & Next Projects: [51:13–53:28]

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Notable Quotes (with Timestamps)

• "I never had a boss in my entire life. I was that annoying kid who... would knock on your door trying to sell you different things." — John Arrow [01:21]
• "It just makes you more the person that you already were." — John Arrow [25:35]
• "You never regret selling. It’s never happened to me... But I’ve met many people who have regretted not selling a company." — John Arrow [21:26]
• "Let’s just create the place where everybody can go and use whatever AI is objectively best for what they’re trying to do." — John Arrow [37:31]
• "We want to make that area where people are not left behind and can always use the AI model that’s best for them." — John Arrow [41:35]
• "What an amazing time to be alive." — John Arrow [53:19]

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Final Thoughts

John Arrow’s story is a candid exploration of entrepreneurship, wealth, risk, personal fulfillment, and living at the edge of what’s next. The episode merges hard numbers with lifestyle realities, all told with the unfiltered perspective of someone with financial freedom and a passion for perpetual creation. Whether building businesses, flying himself across continents, or experimenting with the newest in AI, John exemplifies an irrepressible drive to build, experiment, and shape the future—on his own terms.

Transcript

[A]

Today's guest is John Arrow who bootstrapped his company to 350 people and sold for $100 million. 70 million of that went to his personal bank account. He has his own plane that he flies wherever he wants. And he has a house in New York and in Austin where he flies himself back and forth whenever he wants. This episode is awesome. This is a very interesting guest. I hope you enjoy. Hello, listeners. Welcome to another episode of Money Wise. Today. I have John Arrow with me. Appreciate you joining Moneywise today. John.

[B]

Hey, Daniel. Great to be here.

[A]

Awes it sounds like you're in New York today. You're usually in Austin though. Tell me what takes you to New York.

[B]

I split my time between Austin and New York. I think those two cities pair incredibly well together. And it looked like in New York we had some better weather today.

[A]

But you told me right before this it's going to be like hotter in New York today than it is in Austin.

[B]

I like the heat. I'm one of those people that doesn't complain about the hot months in Austin. It's perfect right here in New York. They pair so well together. I think this could be a second Austin maybe if we figure out the mayor situation here in Charleston.

[A]

And I love the heat. Until it gets really hot in Charleston. I try to go anywhere else but Charleston in July and August. It's terrible, terrible weather. But look, I'm excited to talk a little bit about who you are today. What brings you to Money Wise. If you could tell us kind of a little bit about yourself. And I know you've started a number of companies and businesses. Tell us what you know makes you kind of a good guest to bring on the show.

[B]

I'm a lifelong entrepreneur. I connected with Sam several years back. And one of those things is I'd never had a boss in my entire life. I remember growing up and I was that. That kid, that annoying kid who would knock on your door trying to sell you different things. When he was 7 or 8 years old, I would always have the lemonade stand out at every cor street corner in the hot Texas summers. In the winter it does get cold there. In Austin we have one month that gets down. In the 50s, I would be selling hot chocolate. And so I learned at a really early age that if you were resourceful and you had grit and you tried to do things, you could make money. Then in high school I started a software business and I wasn't really a big fan of going to public high school. It kind of made me not want a 9 to 5 job. So I dedicated myself and my goal was look, once I am earning a thousand dollars a day, that was my goal. I don't have to go to high school anymore and I can drop out. Well, I eventually hit that goal. My parents said no, you're not dropping out of high school. I was on the fence about whether I was going to go to college or not. I'm so, so glad I did because it allowed me to really scale my business faster by meeting other like minded people at the University of Texas that I was able to build ventures with. And it just shows, goes to show you that just because you don't need to do something doesn't mean you shouldn't do it.

[A]

The thousand dollars that you were making in high school, what were you doing?

[B]

So originally I started building websites for people. This was back in the day of geocities where everybody needed to be a be a dot com company like everybody needs to be a AI company today. And I realized I had this slight advantage. I knew how to make these things really really well. Or at least I thought that they were. Well looking back they probably weren't that great. I mean if you're serious about your business, you shouldn't hire a 14 or 15 year your websites. But I was able to do that so that I generated some initial capital where it allowed me to kind of look at the space separately. And I realized I could make a software product to basically help parents monitor what their kids were doing online. My mom growing up, she was a psychotherapist and so she told me these stories about parents really not understanding a, well, instant messenger and all of these platforms and their kids would get into trouble talking to strangers. I realized oh wait, I know how to help prevent this. So I made a piece of software that did exactly that and put it out there. Had a PayPal buy now button and before I knew it it was selling thousand dollars a day every day.

[A]

Wow.

[B]

So I continued scaling that. Eventually when I got into college I saw what was going to be happening with mobile and I shifted all my focus to that which we can get into.

[A]

Yeah, and you mentioned dot com. Tell me more about how growing up in the dot com era and I don't know if we want to call it a bubble but that period of time, how did that shape the way that you thought about growing businesses and making money?

[B]

I was extremely fortunate that I got to grow up in two of the dot com epicenters. First I was living in Seattle for a while. My dad worked at Microsoft. And so I got to see everything that was happening there. Then we moved to Austin, which was really ground zero for, for everything that was interesting happening on the web, at least in my view. And I was trying to make sense of it all as, as, as a young, as a young teenager at the time, I was thinking, okay, wait, why are all these companies worth so much? All of a sudden, all I can see that they're doing is throwing elaborate parties and, and spending a bunch of money. The way I reconciled it after the bust is that, no, they weren't actually doing anything that useful. They were convincing other people that they were. And that was an extreme cautionary tale for me where I realized you didn't need to go out and create this perception that you were generating value. Just go generate value. That's what led to the software company. I said, how can I just get people to buy things? I don't want to have investors, I don't want to have a boss telling me what to do. I just want to start making more money every day than I did the day before it.

[A]

Love that. That's very cool. I reached out to one of your buddies, Neville, before the episode, asked him, hey, I'm having John Arrow on Money Wise. And I want to kind of hear some of the behind the scenes of John Arrow, of what makes him tick, of the history that you guys have together. So I have a couple clips. I'm going to share one right now, but I would love to hear your thoughts on it.

[C]

John is just an interesting guy. He hang glides, he has always flown planes. I remember he would never really drink all that much. And I asked him one time, you know, why don't you really drink? And he's just like, honestly, if I drink, I can't fly within 12 hours or 24 hours. So I always want to be prepared to fly. Like, that's the kind of guy John is. He has a bunch of eccentricities. Like he'll walk around downtown, but only with earplugs because he wants to save his hearing for, for when he's old.

[A]

Obviously. Neville probably has a lot of history with you and it sounds like it was cool. I asked him, I was like, hey, tell me about John. I'm having him on Money Wise and he sent me 7 1/2 minute voice note off the cuff of all the awesome details and eccentricities of, of who you are, kind of what makes you interesting. And I'm really excited to dig into some of those. I even told him, might as well just upload this Voice note as a podcast, because that's. That's how good it was. But tell me more about planes and flying and some of that that he just divulged around, drinking and wearing earplugs. How does all that fit into who. Who John Arrow is?

[B]

Well, first of all, Neville is such a great guy. I mean, that just speaks to the serendipity of Austin, that you find your people in these types of places, right? I mean, there's a saying that San Francisco might be the best place to start a company, but Austin's the easiest place because you meet incredible people that are helpful, like Neville. I've known Neville almost longer than anybody else in Austin. You know, I immediately connected with him over the entrepreneur aspect of it. And I don't know of another city where there's that same gravity where you find those people. And so one of the things is, once you find somebody like Neville, they get to learn what makes you unique pretty quick. And I think I was a freshman at UT and I was really into flying airplanes. I had just gotten my pilot's license. I still try to fly regularly today. I'm really, really into it. And that was exactly right. It's like, okay, I have this optionality where if I take a sip of alcohol, unlike driving, it's not about blood alcohol level. It's literally one sip of alcohol. You have to wait eight hours, and then technically it needs to be below 0.04. But if you were above.04 after eight hours, you were going probably too hard to begin with. And I love that option. I kind of approach life in that way, too. It's like, why should you close doors unnecessarily? I mean, there's times to doing it. There is a real cost to options, just like there are derivatives. But that was just something that I love so much. One of the things devil knows about me too, is that I want to try to live as long as I possibly can, ideally forever. I'm really into the whole longevity camp. Hearing is a thing that we haven't figured out how to preserve and to protect. So I'm really cautious of that. I'm around airplanes and around guns. And if you live in Austin part of the year, you're in the live music capital of the world. So there's a lot of loud things going on. It also breaks your concentration, your flow state. I get so many of my ideas. I get so much done while I'm walking. I don't want to be distracted by it. I used to wear the earplugs Now I wear the AirPods, which are a lot, I think more socially acceptable to wear to rather than earplugs. And I think it's a game changer. I think it's the best product that Apple's ever made.

[A]

Yeah, I, I walk around with AirPods too. Are you listening to anything or is it just noise or just nothing?

[B]

I love podcasts and I listen, I listen, I listen to this podcast, listen to other podcasts that I like. But generally I start out just with silence and trying to block out as much of the world as I can and taking it through visual stimuli rather than auditory.

[A]

Yeah, I find sometimes when I'm looking for deep work, I'll put my, I have another pair of headphones, Bose QuietComfort. And I'll put those on and I'll turn on the noise canceling and you know, an hour and a half goes by and I realize I haven't been listening to anything but just the fuzzy noise canceling sound. I'm like, oh, that was actually kind of nice listening to nothing for a couple hours.

[B]

It's rare these days, right, to be able to be with your brain and not be bombarded by something.

[A]

Yes. Now I want to listen to another clip from Neville. There's a few. They're all good, they're juicy. So here comes another one.

[C]

You can ask them about what they did for my 30th birthday party. They were about to sign their company and make a life changing amount of money and it happened to be my 30th birthday party, you know, a decade back. And him and his co founder Mickey went to Cuba with me illegally and six guys and we couldn't communicate with the outside world and they had to leave two days early. The party, we're gonna be there for a week. They had to leave after a few days to go sign their company away and they went to this foreign country where they couldn't communicate with anyone. We didn't even know if they were alive when they went back. He created the subscription process company.

[A]

Okay, so we'll get to the subscription process company in a few minutes, but you gotta tell me and the listeners more about this 30th birthday party because Neville just barely explained it and I was, wait a second, I need a whole episode on this.

[B]

Neville is somebody who makes the most of every single experience. He will just basically want to live it up as much as possible. Like every moment you've probably heard about, he wears like a death clock to know how much time he has left. And so Naturally, you're turning 30. You have this milestone. He says, what's the most difficult. What's the most illegal country to go to? Decides he wants to go to Cuba. And I didn't really know much about Cuba other than that we weren't supposed to go at the time. When he asked me, I'm like, absolutely, let's do that. And so we literally couldn't buy tickets from the United States. And I was not going to fly my plane to a communist country. We ended up in Cancun. We bought in cash, which I don't care, you know, how much you fly. Nobody ever buys a plane ticket in, like, cash, like, literal money. And it's the most suspicious thing ever. We went to Air Cubano. They give us that. They give us these tickets. They give us something, supposedly that's a visa to be there. We get on the plane, we're completely segregated between the Cubans and basically the Americans that aren't supposed to go there. We're not allowed to talk to them. And then we land. And it was like getting off of a time machine. I felt like I was back in the 1960s, and it was one of those. Those countries that. I'm so, so glad that I went there. It's definitely a paradise loss. And, I mean, how fitting was it we went to the most socialist, communist country right before doing the most capitalistic thing in the world of. Of selling a company. The crazy thing about it, your cell phone doesn't work, though, too. So they didn't even know whether we got out, if we were okay or not. We just left and hoped that they would return someday.

[A]

That's so funny. So did you know that he was like, did they die? Like, were you aware of his concerns about your life when you left, or were you just like, I just got to go deal with this company sale?

[B]

I was more concerned about theirs. I mean, we were at least on the path home.

[A]

Sure.

[B]

They wanted to. To basically get every aspect of the experience. My favorite memory was, I think it was Neville's brother decided to start playing guitar and trying to earn money in Cuba, which theoretically they're not allowed to do. And he started making money. People would put money into the flat. And then we went to the best communist restaurant there was, which everything's the same price, and enjoyed a meal based on the money that he had, he had earned in Cuba.

[A]

What a. What a crazy story. Yeah. I don't know if I worked in an airline and someone came and bought money with cash. Like, I think I would just Instantly assume something incredibly illegal or suspicious is going on. But what year was this? Was this like 2015?

[B]

I think it was like, maybe 2013 or so. And it was one of those things where it was only illegal if you spend money in Cuba. Theoretically, it wasn't in US Laws, if you didn't spend money also in Cuba very nicely, they would not stamp your passport. Passport. If you were nice to them. We had one person in our group, I think it was Noah, Noah Kagan, who decided to be like, oh, you're not going to stamp my passport. I already know how this all works. And they grabbed his passport and stamped it. And so he. He has that stamp in there. Probably. Probably caused him some trouble later on.

[A]

That's fun. Love, Noah. Good friends with him from some of the business we've done together. That's. That's such a funny story. Okay, I have another clip. And we'll. We'll. We'll jump into some other fun stuff, but I think this one's maybe the most interesting.

[C]

When they went back, he created the subscription process company where you could sue anyone for 97 bucks a month. He created, like, suing as a service. And it actually helped me a lot because I had this big problem where Amex misplaced a million of my points, like, eight years ago. And this was when, you know, airline points or Amex points are worth, like, a ton of money. And they replaced, like, over a million of my points. I could never get them to fix it. It was a clerical error on their side. They said, go to Starwood. They said, go to Amex. You know, this back and forth circular thinking no one could solve the problem. So I tell John Arrow about this. He's like, hey, I have this company that's going to sue them. Let me try to handle it. Literally, in two days, the head of American Express Legal, the. The full head of the entire department, she calls me on my phone and was like, hey, you have a problem. How do I solve it? And I was like, just give me all my points back. The next day, all my points in my account. I'd been working on this for, like, over a year. And I called John and I was like, dude, what did you do? And he's like, oh, I just sent them a thing that said they got hacked. Like, clearly you messed up his points and placed him in someone else's account. So you clearly got hacked. And the number one thing that companies hate, credit card companies is getting hacked. And.

[B]

And it just solved it.

[C]

I remember thinking, like, dude, this. This guy is like, he just thinks in different ways.

[A]

So tell us more about the story because it sounds like you're some type of genius hacker for money, for hire type of, you know, behind the scenes stuff. Like was that a simple process for you or did you have to do some deep work to figure that out for, for Neville?

[B]

Well, like, like Neville, I love doing these experiments. And so one of the companies that I started after I, I sold Mutual Mobile the first time, I kind of sol we can get into that. I said, wow, I had access to this amazing team of lawyers, literally the best lawyers money can buy. It's so unfair that other people don't have access to that. Big companies do. And so if a company does something that isn't right, you're not really able to do much. It's not worth doing much. And so I said, well, what if you created a company that basically automated small claims lawsuits in the United States? There are a lot of pain. You have to go to the courthouse and do that. And so that's exactly what we did. Really small team of people. This is before AI so everyone's manually filling out forms, delivering into the courthouse, running them. And we were actually responsible for more lawsuits, our company in Texas, than any other company because we were the ones filing these things. It was, it was pretty, pretty hilarious. I mean, we had courts reaching out to us, like, why, you know, who are these people? But the crazy thing about it is most of the time these companies, once they're caught and once they realize they weren't doing the right thing, they'll get in touch with that person and they'll want to make it right and they'll, they'll want to settle it or they'll realize, oh, we just, just didn't realize the issue. And so was the case of what was going on with Neville. He was owed these points. These points, points should have been his points. He had tried. He's a smart guy. He's one of the smartest people that I know. And it's just American Express isn't going to take anyone seriously. And I've been an American Express user for many, many years. They're really good, but sometimes they get into an issue where they're just not going to deal with it. And so what I did is I helped them use the site and we had somebody create all the paperwork. And I think initially we didn't get a response. And so what I did is I have a service that gives me the email address of everyone at a company. And I said, well, obviously, you know, American Express, there must be something wrong here because they're normally a great company. So I think we sent out an email to every single employee at American Express with the subject line possible data breach. Right. Obviously there must be something wrong if Neville doesn't get that email.

[A]

Yeah, right.

[B]

And obviously once the CEO, you know, people don't, aren't going to really interrogate exactly what it means. But once enough people forward this to the CEO, the cto, the clo, it gets looked into. And American Express, to their credit, once they realize it, they did a good job and they, they credit him the points. Some companies can be more difficult, but that was the whole spirit of that, of that website.

[A]

That's, that's really interesting now, now I'm wondering if Neville should have asked for like 2 or 3x of the number of points. Like yeah, actually because of the trouble. Give me 5 million. Yeah, that's funny, that's funny. Well, okay, so tell us more about Mutual Mobile. You've mentioned it a couple times. Of course that's one of the main businesses that is, you know, what led to your wealth. But tell us more about it. What, what is Mutual Mobile? What did you do? And kind of where are you at now with that real quick? Today's episode is sponsored by Ocean's Talent. If you're trying to hire a great EA or Ops person, right now you're looking at 80 to $100,000, sometimes more. And I know a lot of founders have tried to go the remote route before and gotten burned. Sometimes they get ghosted, the work sloppy, you end up redoing everything yourself. I've heard the stories before and I've even personally lived them. Ocean's Talent is completely different. They pre vet every single candidate with thorough skills assessments. So whoever they match you with is ready to go on day one. And it's not just EAs. They do marketing, ops, finance, HR, sales, even AI workflows. I've hired people personally through Ocean's Talent and I'm blown away by the quality of work they produce. Sam Parr has his personal assistant through Ocean's and he describes her like she runs my life. I couldn't live without her. I have total trust in her and I don't trust anyone. That's the bar they set. So if you're a founder drowning in stuff, a great hire should be handling. Check out Ocean's [e-mail] Moneywise. That's Oceanstalent.com Moneywise.

[B]

Kind of like how I met Neville when I was at the University of Texas. I met some other entrepreneurs and we were entering in college when the iPhone was released and it was this amazing moment. It was probably for people that don't remember the iPhone being released. Well, it was, it was like chat GPT times 10 in my opinion at that point it was the device that was going to change the world. Everybody saw this. I think, I don't think it was. You know, we had a super unique enthusiasm about it. But my, myself and my co founders, what we realized is that this was going to change every aspect of the world from education to financial services to defense, you name it. And we said we want to build iPhone apps, but we can only build so many. There's a shortage of people that can make these things. Let's try to amass and develop the company that is capable of helping the enterprise world create mobile applications. And so that's exactly what we did. We had the largest number of iOS engineers under one roof outside of Apple for several years. And just by having that scale it meant that most of the Fortune 1000, when they wanted to get something made, they came to us. So it started with mobile and then we parlayed that into tablet, into Internet of things. We did stuff in the self driving realm. We've done stuff in any type of new emerging tech before we sold the company. We started doing a lot in AI before ChatGPT was a household name. And so that they kind of gave me the launch pad to know what I was going to do next. But like I said, we sold the company twice. So in 2013 it was like the height of the mobile bubble is what I call it. We were doing close to $45 million a year. We were receiving revenue multiples on the valuation of the company. We were seeing like 2x revenue multiples, which is insane for a company in kind of the, you know, we didn't think of ourselves as a services company, we thought of ourselves as a solution company. But still a 2x revenue multiple was, was pretty interesting. We decided that it probably made sense to run a process and sell the company. We were split on whether we should sell the whole company or part of it. I was of the belief, I was the CEO at the time and chairman. I was like, let's sell the whole thing. This is a really, really good deal. The fact that we're even entertaining a hundred million dollar valuations and that we've raised no money, I mean, this is a really, really magic moment. And we had companies ready to buy the whole thing. We ended up going with WPP the large advertising conglomerate, great company, because they were willing to let us do a deal, a minority deal, where we still stayed in control after we sold. And so that's exactly what we did after we sold. I left a CEO, I went and flew my plane around the world, did interesting new companies like things that let people sue anybody. And then, you know, helped as a chairman, helped, but I wasn't running it. And then about five years later, they asked me if I'd come back as CEO, and I said okay, but on one condition. And that condition is that we sell the rest of the company. And so that's what I did, and we sold the rest of the company in 2023. And I just finished my earn about a year ago or so. Now I'm looking at, looking at new things.

[A]

Okay, so 2013 was the initial partial acquisition. And walk us through some of the numbers behind that. What was the actual acquisition? How much also did you make from that acquisition?

[B]

So, I mean, we had no capital raised into the company. So a lot of times when there's venture deals, it's a situation where you're giving money back to the investors. There were zero investors in the mutual, so we had five, five total people. And we decided, look, whoever wants to sell a portion of their, their stock can do so. And I decided to sell the majority of my stock at the time in that. And the valuation, I think it was around $70 million or so. And so it was a very good, very good exit for me. It was one of the best decisions that I ever made. I'm really glad I did that then. And it was one of those things where we kind of got to look down the other alternative reality too. We got to keep running the company. We got, when we ran the company for 10 years after that, which was incredible. We, we worked with hundreds of interesting companies. We, during the course, I hired thousands of people and it was a great journey. But, you know, one of the things that I've come to realize through other exits too is that you never regret selling. It's never happened to me, and I don't think I know anybody who's ever regretted selling a company. I've met many people who have regretted not selling a company, though I've heard

[A]

more of the latter as well. So you mentioned five of you who are actual shareholders. How many people were at the company at the time of the sale in 2013?

[B]

I think it was around 350 or so.

[A]

Okay, 350. So you made 70 million. What did you do with that money, I mean, that's a life changing amount of money. What happened, you know, the day it hits your account? What was that feeling like?

[B]

What's really interesting, like you think about the date, the day before. I mean, you, theoretically, this money didn't come out of nowhere. You had, you had this, but it was on paper, right.

[D]

So it wasn't liquid.

[B]

It's not like all of a sudden, you know, you knew you had it, but you had 99% of your net worth locked up into what was an illiquid asset. And when you're going through a process, selling a company, you oscillate between days when you think your company's worth a hundred billion dollars and when you think it's worth nothing. Right? Yeah, it's like, it's very, it's this time period where you're, you're really curious. I mean, I think that was one of the fascinating things about going through the process is you wanted to see where, where it ended up. Because we had, we had an offer for $100 million for the company. We went with less because we wanted flexibility on some of the terms. And so the day after the wires hit, you're thinking about your bank account balance and it's literally like an order order of magnitude higher than it was before, maybe two orders of magnitude. And so it changes your perspective on everything. Right. If something, if you used to think about something costing $100, it's like it costs $10 now. I remember kind of going through that, that mindset and I had been really fortunate that I had made, made a fair amount of money before through other businesses. But this was definitely, you know, kind of an order of magnitude more and more. The biggest thing I realized is, wow, you know, this is a situation where I never, never need to work again in my life. You think about risk free interest rates even then when they were relatively on the low side, when you could just, you can just bank interest. And so the kind of. I didn't really do anything that differently after I saw. I think I maybe bought, I think I bought the first Model S Tesla in Texas, which they weren't supposed to sell me. It's a long story, but they wasn't supposed to have it.

[A]

But other than that, why weren't they supposed to sell it?

[B]

I'm interested in had this protectionist law. They've gotten way better where you were not able to buy directly from the dealer, you had to go through another third party dealer. So any of interesting cars that you had to go to Colorado or Something. I just showed up at the Tesla shop where it was a showroom. I said, look, I want to buy this car right now. They made a call and they're like, look, we, we can't sell you this. We don't even have a way to give you, like, temp plates. I'm like, I don't care. I don't need the plates.

[A]

Yeah, I just came from Cuba. I don't care about place.

[B]

I did not ask them to do this. I did not tell him not to do it, but I didn't ask him to do this. They made me fake. I think they made me like a fake California temporary bag or something and put it on the car. Maybe there's a real. I don't know. But I did get pulled over and the cops were thoroughly confused by the situation.

[A]

So funny. You did get pulled over. How soon after getting the car did you get pulled over?

[B]

And they're like looking at this plate and you know, like, oh, you know, Californians are strange people, I guess is how it works there.

[A]

That is so funny. Oh, man. Okay, so you mentioned you already had achieved some wealth prior to that acquisition. What was your net worth before the $70 million, you know, paycheck, and it

[B]

was like flirting, like liquid network liquid worthless. Probably floating worth around a million dollars before.

[A]

Okay, so yeah, you weren't going from, from nothing to, to wealth, but 70x. And what was the pay structure of that exit? Was it all at once it hit your account 70 or was it a payout over some period of time?

[B]

The majority of it was. Was up front and then there was an earnout component, but the vast majority of it was up front. And I, I always encourage that. I mean, I think earn outs, fortunately, are really problematic. There's a thought they're going to keep things aligned, but in reality they often don't and they end up as a, as somewhat of a mess. I've never, ever talked to anybody who's earned out. Went really well.

[A]

So that. That initial payout was, let's say, 55 million, 60 million.

[B]

It was a signif. It was a significant amount. I can't go into the exact amount because of an. But I, but I can say the vast majority of the. I mean, there's none of the money went on to the balance sheet of the company was all secondary to, to us. And I, I took the, I took the lion's share of it.

[A]

Okay, so majority upfront. And you bought a Tesla. What, what did you do with the rest of you? Leave it into you Know index funds or did you invest? Are you building new companies you mentioned, I mean, tell me more about what you did with that money.

[B]

All of the above. I mean, I think one of the things that's fascinating about money is it makes you more the person that you already were in my opinion. Right. And so before that I was investing. Before that I was doing experiments. Before that I was flying airplanes. And so it kind of turned up the rheostat switch on all of those in a, in a big way. I think one of the great things about it is you could start to make riskier investments. It was possible to obviously not just do index funds. You could do things that were more exotic. You could get more into angel investing. I was working a hundred hours a week before that and all of a sudden I had this abundance of time so I could take the airplane that I love flying and go on further destination. So I did a lot of, I kind of turned up the rheostat switch on all of those things. I did a lot more investing. And one of the things that I found, the more investing that I do, I like it and I think it's a great passive thing to do. That being said, I enjoy the most experimenting and starting new companies. I think that's the most fun. It maybe doesn't necessarily have the highest expected value, it's just investing, but it is something that I, that I enjoy immensely. I mean, one of the things too is it allowed you to kind of get into areas where you, you didn't really necessarily have domain knowledge, but you wanted to, you wanted to learn more super into rocket ships and outer space. And just through, largely because of serendipity of knowing Neville and other people. I got invited into a very early round of SpaceX and so got to kind of do that just because I wanted to go to see rocket launches. I didn't even think it was, you know, investment grade. But it leads to more serendipity. It lets you, it lets you kind of flip the quarter more and more once. You're not as afraid of losing.

[A]

Yeah. What's the, what's the best place you flew your plane during that period of time? You said you went to some fun

[B]

places, probably the Lesser Antilles. So the extreme Eastern Caribbean was a blast.

[A]

Very cool.

[B]

This was before a lot of the flying was before we really had electronic charts, I had an iPad, but I don't think it was that great at the time. And so you take off and not always know where you're going to land, which is kind of Cool. And if you're a commercial plane, they'd never do that. But you can do that as a private pilot and just say, oh, wow, that Runway looks amazing. Let's look it up. Distance is good. And there's this small little island with a beach, and that's about it in a Runway. You land there and maybe there's a hotel room, maybe there's not, and then you fly somewhere else the next day and you're just.

[A]

I mean, these are single engine planes, right? So what's the. Yeah, yeah, so what's the, what's the distance that you can really go on?

[B]

This is a serious SR22. You can do about a thousand nautical miles without stopping. And single engine. So if that thing stops, you're pulling the parachute with the plane. The plane has a giant parachute that it floats down.

[A]

I'm assuming you've never had to do that. But now I'm wondering, okay, let's, let's open. Yeah, exactly. That's a one and done type of thing. And then you mentioned some exotic investments. You use the word exotic. Tell me what, like is the most exotic investment that you've made and why.

[B]

When I say exotic, I mean investments I probably wouldn't necessarily say are investment grade. I mean, things like when friends that you admire a lot are starting a new company, you can do an angel investment into their company, or you get invited into some type of SPV where you really don't know if this is going to work out or not. When you have, when you have kind of more shots on goal, you're willing to take that chance. And most of those do not work. I don't think that's a sound strategy for people to just do lackadaisically. But because of some of them, because of the power law, the ones that have worked have immensely paid for the ones that have, have not. And it also ends up getting more and more things, more great opportunities on your plate, the more of those that you, that you do as well.

[A]

So when you're not spending money and flying and investing, where's the rest of the money sitting? Is it in mostly index funds or do you have a financial advisor and wealth manager?

[B]

I'm really against kind of wealth managers and financial advisors. By and large, I know there are some good ones out there and there's some people that if they, if they have a good relationship, I think that's great. My take is it should be your business to kind of understand your own personal finance and your own business. I've invested my own Money since I was 13. My dad gave me access to a brokerage account, so I feel very comfortable doing that. Look, it's hard to bet against the United States. I love the S&P 500 spy Dow. I think there's these other companies like Apple that keep compounding over and over again Google and Tesla. One of the great things about these companies is that if you, if you buy and hold them, they're going to appreciate. And so, you know, I think they're the type of companies that you just don't, you don't sell them.

[A]

Yeah, no, that's, that's fair. I, I, I, I've heard that a lot. I have a similar stance on wealth management. I think good for people who really just don't want to think about it at all. But if you want to really be involved in the numbers, I think think there's good ones and there's bad ones. We'll keep it at that. Back to the story. You said you were hired back as a CEO of Mutual Mobile. Tell me, like what financially triggered that for them and then for you? Why accept the role if you're more financially free, then you never need to make another dollar again. It sounded like, why'd you go back?

[B]

I was definitely conflicted when it was presented to me. There's definitely a financial motive in that. I still, even though I sold the vast majority of my, my stake in the company, I still had a significant amount of, of value that was locked up in this illiquid security. So there was a desire to see that become something and that was the motivation. I like to see things through and complete them. Also. The world had changed a lot. We had a lot of new emerging tech. I was curious to be back into that role. It's fun to hold the reins of a company where you are managing hundreds of people. That was really thrilling. I had missed that. After I had sold the company, we literally went from 350 people to, when I was doing my experiments, maybe I had three people again. So I wanted to put myself back into that perspective. The reason that I think they had asked me to come back is we sold that first valuation at the top of the cycle again. Businesses like ours don't Normally trade for 2x revenue. There's something really special going on when that happens. And if you look at kind of your typical advertising agency, it trains, it trades for maybe 1 times AR at most and a lot of times it's like something like 0.75 arc. So this was a special moment. The other reason that I wanted to come back is I felt like I owed it to the employees and to the team. I helped build this thing. I have responsibility for it. And I wanted to. I wanted to make sure everybody had a good outcome.

[A]

What was the valuation? Well, you mentioned it was 100 million, give or take valuation. The first sale. What was it when you came back and what was it when you left the second time?

[B]

Right. So the company, it didn't do poorly during that time, but it certainly didn't grow at the same rate. So you kind of had two compounding factors working against valuation. One, growth had slowed a ton, and then two, you ended up in a situation where the market began commoditizing. Right. Whenever there's a new technology, there's tons of fragmentation. There's all of these new companies. Everybody's starting something, and then inevitably consolidation hits. There's acquisitions and prices go back to the baseline, and things commoditize. We're starting to see this in AI already. And so we were. While we were kind of the new novel company back in 2013, when I returned in 2018, or maybe 2020. Yeah, 2020, I guess things had changed and we weren't trading at the same multiples. It was a much more established business area. And so when we started running a process and looking at buyers, before it was everybody was a potential buyer. I mean, we had term sheets, SAP from Deloitte, from Accenture, you kind of name it. And now we were looking at more traditional IT services companies, a lot of international ones. And these were companies that weren't really strategics in the same way that the first round were.

[A]

Okay, so you joined the second time. That was 2019, you said.

[B]

I'm really thinking when that was, maybe it was 2018.

[A]

2018, it stayed for five years. So 2023, it took a lot longer than I thought. Okay, how long did you think it would take?

[B]

I thought we could probably do it in a year. And there was a lot of things. I mean, we could have. You could always sell. You can always sell. But if you want to get a what you think is a good price, it makes sense to. To do things in the business. So I ended up, sure, rather than just putting on the CEO for sale, hat I ended up putting on the CEO. Let's get our hands dirty. Let's figure out how to get this business growing again. It was a lot of fun. It's a lot of work. Yeah, it was a lot of fun. I think it was more fun in some ways the second time, surprisingly, because you didn't have the same risk profile.

[A]

So you had less to lose. You already won.

[B]

Yeah, exactly. This was more like kind of a victory lap. It probably meant too that I didn't take it quite as seriously, but I still took it pretty seriously. It was just, it was just more fun. It was much more of a, of a balance rather than a full on. This is the only thing I do.

[A]

And what was the second exit like? What was, what were the numbers behind that and what did you make personally?

[B]

That one definitely is still under an NDA, but the valuation, it was, you know, it was, it was a very good valuation for everybody involved. You know, the great thing about it is we, we had an initial investor, WP bought shares. We made sure that they had a great outcome, especially considering where the business was at. Everybody who sold the second time was, was happy with it and it was the right thing to do. I mean, if we, if we had waited and not sold, I don't know, given what's going on with AI right now, I don't. I think we would have had to lay off hundreds of people.

[A]

That's rough. Yeah.

[B]

Right now what you can do with some of these tools that are out there kind of makes mutual mobile and companies like it not as relevant. You need to, you need to change. There's going to be amazing new businesses and I can talk about a little bit of some of the new things that I'm working on in the space, but I think the traditional companies that produce digital products, why do you need them now?

[A]

Yeah. Were you fiddling with some of these side projects during that second term as CEO or was that like everything in one bucket type of role?

[B]

We could see where things were going with AI, so we were really fortunate that we got to do a lot within, within machine learning with computer vision. So even though LLMs weren't really the mainstay, we saw what was about to happen. Like we like, wow, this is really powerful. It feels like there's an inflection point there. And so I knew I wanted to do something in AI even before ChatGPT came out. It was just kind of a happy coincidence. In, I guess it was November of 2023 that ChatGPT was launched, that I was basically a free agent again.

[A]

And you were. Is that when Freedom GPT sort of came to life? Okay, tell me more about Freedom GPT and you know, how you started getting involved with AI and LLMs.

[B]

Yeah. Daniel, did you ever use AOL Instant messenger growing up?

[A]

Oh, of course. I was tall kid, 1953 because I'm tall. I'm 6 foot 5 and I basically stopped growing when I was 15. So you can do the math.

[B]

I remember using it too and thinking it was such a cool piece of software and that's how you sit with your friends. There was this one user on AOL Instant messenger called Smarter Child and it was this robot that you could talk to. When I was like 11 or 12, I thought it was like the coolest thing ever. It wasn't really AI, it was just a bunch of if then statements. But you could ask a question and then Smarter Child will reply to you. And very quickly you'd ask something and it would say, that's not appropriate, I'm not going to answer it. It was the first time a computer told me, you know, push back, you can't do that.

[A]

Yeah, right.

[B]

Like who, you know, who's this computer to tell me that?

[A]

Right?

[B]

And that was 11 or 12 year old John. And then I didn't feel that way again until November of 2023 when I first started using Chat GPT. I was so excited about this. I had been following what OpenAI was doing and first couple inferences go great. And then all of a sudden I asked something pretty innocuous. I don't remember what it was, but it was not that crazy. And it tells me I'm not going to answer, etc. It's like, wow, this super powerful technology is deciding what I can and can't ask a computer. That doesn't seem right.

[D]

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[B]

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[D]

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[B]

I knew with my co founder Troon from Mutual Mobile, we wanted to start a company that let people use AI without needing to get permission. And we knew there was going to be a bunch of models that were going to be coming out. A lot of them were going to be relatively open and uncensored. Some were going to be proprietary like, like OpenAI's. And we said let's just create the place where everybody can go and use whatever AI is objectively best for what they're trying to do. Maybe you're trying to ask a math question and then subjectively miss you and I could ask the same question about something and there might be a different model that's better for us just based on our history of using it. And that's what we wanted to create. We had very quickly after launch we had a couple million people using the platform and it's, it's been a really, it's been a really fun business. I think it's something where it's a rising tide situation as there's new models that get released. We put them up there and so it's one of the first ways that people use a lot of the new AI products.

[A]

Yeah. When, when you think of new companies now I'm curious, we have something called the threshold number on money wise and it's, you know, the, the number that you're attaining for before you feel like you've made it. You don't need to make another dollar for the rest of your life. Is Freedom GPT and some of these other companies. The investments you're making, is it to make more money? And if so I guess what amount of net worth are you attaining for? Or if not, you know, what was that number when you did finally reach it?

[B]

My view is money is a proxy, right. It's to going it's like it's like crude oil or something, allows you to do more of what you already want to do. The test that I look at is what Naval Ravikant says, he says, you know, in life or the best intelligence says are you getting what you want out of life? And I view money as, as kind of a symptom, a side effect of doing other Things with high impact. It's very important, it's fun to make in its own right. But the bigger thing is, are you kind of achieving the impact that you're going to achieve? I'm of the belief that we're of this phase, that there's going to be massive abundance like what Elon's saying with, with the robots coming with Optimus, that we're going to have to look for other ways to derive meaning in the near future.

[A]

Freedom optional future, right?

[B]

Yeah, for sure. I think it's going to be something where if you have access like to scarce resources that you previously had to give money to create, what's the point? If you can get as much of that as you want? There are going to be things that are still require. Money, land and, and probably you know, certain works of art and names and different things like that. But I think like it's maybe more of a Maslow's hierarchy of needs question. Early on when you're starting a company it comes down to the whole ramen profitability thing, right? Let's create enough money so that you're at least self sustainable. You can feed yourself, you can pay your employees. Eventually as you kind of transcend that ladder and get up to the more self actualization side of it, it's more are you, are you getting out of life what you, what you really want? And so there was a moment I think after Mutual where I realized I didn't need to work again and I kind of tried not working and I realized I just loved building too much. And so Freedom GBT and some of the other projects that I have going on now are, are side effects of that.

[A]

Yeah, no, that's fair. I think that's certain. Like a philosophy or worldview of money in general. When you think about like the philosophy or the principles behind Freedom GPT and even the direction of some of the businesses and investments you're making now. Walk me through how you, you know, you view some of this like open world freedom, even Freedom GPT, the naming nomenclature of it obviously has a connotation why? I guess why does it matter to you for people to have access to that? That's unfiltered.

[B]

Going back to Cavett Co. We talked about where I let anybody sue a business. This was this really leveling force where people didn't have access to attorneys. And I saw kind of the good that can come out of that. There was this whole digital, digital divide early on with who access to the web and who didn't. There was another kind of version of this with who had access to banking and not not having banking. I saw the same thing playing out again with AI where there was going to be a class of people that had accessed artificial intelligence the top tier and there was going to be a people that didn't or maybe were taking advantage by it. And so I saw this call this real need. Let's have that place where we make sure that people aren't left behind by it already. If you're looking with what anthropics are having an anthropic great, great, great company but it just boggled my mind. Now they're asking you to submit photo ID verification before you can use some of their models which is who are they to say if you don't need to show an ID to vote, why all of a sudden you need to show an ID to use an AI model? I don't, I don't want to get into politics but it's just mind boggling to me that, that, that's that they're the ones that get to police that. And you can come up with some reasons. I understand some of the downfalls. I do think AI needs to be regulated but I'm was sure of it that the things like anthropic we're doing we're going to become the norm rather than the exception. So we want to make that, that area where people are not left behind and can always use the AI model that's best for them.

[A]

No, that's an interesting worldview for sure and I think it's likely to your point earlier it's going to be in an ever evolving worldview as technology continues to kind of force opinions on the matter. Back to money. Just briefly, what's your current net worth? Liquid and illiquid. And what does your actual personal spending look like every month?

[B]

Month it's well into the eight figures. The vast majority of it is, is, is liquid in stocks. There are some, there are some private things that are out there that are not liquid now but will likely be liquid very very, very soon.

[A]

But most 75 give or take 80 liquid.

[B]

It's probably closer to, probably closer to 60. 65 I think.

[A]

65. Cool.

[B]

Yeah cool. And I think that's like kind of like the right mix for me. Like I don't, I don't feel like any of your investments or your should give you heart palpitations or keep you up at night. And my goal with investing is is it should, it should sustain whatever your spend is in life. You should always kind of a Given quarter, maybe not a given month because there are market fluctuations, but on a given quarter, ideally, your net worth steadily increases, even without, you know, you needing to be dependent on an income source. I mean, it's great to have diversified income sources. I think that's really, really important. But ideally, your investments are at a point where no matter what you do, your net worth is kind of continually increasing.

[A]

Okay. And so well into the eight figures, we're talking. I mean, closer to 100 or closer to 50.

[B]

Somewhere in between that.

[A]

Somewhere in between that. Let's call it 75 for the sake of the conversation.

[B]

So well into the figures. But on the south side of 50.

[A]

Currently on the south side of. Okay, cool. Now it's helpful. And a 65% of that then in liquid assets.

[B]

Stocks, basically. Yeah.

[A]

Okay. What does your personal spending look like? What do you actually spend your money on outside of flying? You fly every week, right? Give or take?

[B]

I fly either myself from. Or I'm being flown by it pretty much every week. Yeah, pretty much.

[A]

Do you fly private or is it all commercial in your own plane?

[B]

When it makes sense to fly private, I will. I don't think it's. I think it's something where. When there's an experiential need behind it or when there's like a real work need, maybe there's two cities that aren't connected, But I like to try to fly myself places. I feel like that's what makes me a better pilot. I do want to switch planes to more capable planes soon. So I'm flying once a week, either myself or by somebody. Okay. The way I think about spending is something that I thought a lot, a lot about this. Like, the way the thing to be careful with spending with generally isn't overindulging. Maybe private air travel is the exception to that. But if you think about spending in general, like if you went out and bought a ton of different things, you went shopping, you had kind of this extravagant vacation or something, you come back, you're probably not going to lose money doing that. There's a lot of people that, you know, do that and they get tired of. I think Paul Graham kind of came up with this idea. Like, the way that you lose money is when things kind of trick you into thinking they're investments and they're not. Right? So, like, if you spent years laboring over a business, throwing capital into it, and it keeps losing money, that's what you need to be more careful of than just like overindulging. It's like, if you went out and ate a bunch of ice cream and pizza one night, you're probably not going to feel like doing that the next day. You kind of got enough of that out of your system. Whereas if you think you're doing something that is an investment, that's not, that's what gets you into trouble. So I think as it relates to kind of personal spend, I don't feel like that's something I'm, I'm less careful in watching. I think most of my personal spend right now is what I would call discretionary legal, where there's, there's different matters that I'm, that I'm in where it makes sense for me to spend money on that. And it's probably like, you know, 20 to $30,000 a month in that.

[A]

And that includes cost of living. You know, do you own or do you rent?

[B]

Just legal.

[A]

That's just legal. Okay, so let's include then the home you live in. It sounds like you have a spot in New York and in Austin. Is that, is that. Or do you have other real estate places?

[B]

I have a, I have a condo that I, that I, I own in. In Austin. Without a mortgage, it's like about $2 million. And then that's HOA expenses, tax expenses. That's probably. And they have room service there. It's at the W Hotel. So that's a little dangerous. You end up using that.

[A]

How much, how much you use that? It's like every day type of thing or a couple times a week more than you think?

[B]

Yeah, yeah, yeah.

[A]

I mean, maybe not more than I think. If I lived there, I'd probably use it every day because I hate, I hate making my own food. I'm, I'm like a 2 year old in that sense. Sense. It is very convenient.

[B]

So my, my residence in Austin's probably, it's probably like around $10,000 a month all in. If you take all the HOA and taxes and other expenses. And then I have a place here in New York that I'm in right now and I rent this place and that's like 11,000amonth. So that's, that's kind of.

[A]

So 10 plus 11 plus about 30, which is the discretionary and. Yeah, then the, the fun stuff. I mean, the, the plane. What does it cost to upkeep the plane and fly, you know, once a week, give or take.

[B]

Plane's interesting because there's fixed expenses and there's variable expenses. Right. So this plane, most of the expense for a plane is like if it just Sits there. Every year a plane needs to have an annual inspection where they take it completely apart and put it back together or nearly so. So it doesn't matter if you fly one hour or several hundred hours, they're doing that. Right. And then you have the variable expenses, which are the fuel and the time on the engine. Most of the expense for a plane on variable isn't really the fuel. It's the wear and tear you put on the engine. So a lot of people think of the economics as having an engine reserve program for the aircraft, but the plane itself is not. It's not that crazy. I would say all in on the plane, fixed variable expenses probably comes out to somewhere like maybe 7,000amonth.

[A]

Okay, so you're looking at like, you know, 50 to 65,000amonth in overall spending.

[B]

Right. I'm thinking of just other things. Like there's. Yeah, there's, you know, what do you do for fun?

[A]

Yeah, I was gonna say. I mean, it sounds like you fly

[B]

for fun, but it's funny, I've never really been too into cars, but I. I ended up getting a lot more cars because I'd fly these small little airports and none of them, some of them would have cars, but a lot of the really small ones do not have any transportation. If you're somewhere really remote like Marfa, the next closest rental car could be like a couple hundred miles away. And so I started putting small cars, or not small cars, just kind of cheap cars at a bunch of these little airports in Texas. And then I let other pilots use them and rent them out. It was called VFR car.

[A]

That's very cool.

[B]

Really, really. Well, I actually, up until recently I did this. I. Then I started realizing, okay, the Tesla robo taxi things almost here, we' going to need these anymore. So I just, I just, Just got rid of all of those cars. I only have two cars now.

[A]

How many did you have at the top?

[B]

I think we had like maybe like seven or eight.

[A]

Okay. So it wasn't really a business. It was more of like, you had these cars for you and you might as well make money on them.

[B]

Might as well just. There's more to like, let other pilots do because they fly somewhere really cool. And like, how do I get around? There's no taxi. There's no Uber.

[A]

Yeah, it's a whole thing. Yeah. Do you manage all the logistics of this yourself or do you have like a chief of staff or a personal assistant?

[B]

I have an assistant that I use for this, but I. I try to involve kind of my friends that are interested in my brother Zach, also my younger brother who's interested in similar things. And we kind of work together on a lot of these projects.

[A]

Okay, that's very cool. I've heard, you know, a number of times through this conversation you speak a lot more, I would say intentionally, about the way you've presented yourself as, you know, someone with wealth, someone who's achieved great success in business and almost like not really deferring happiness before a future milestone, which I really appreciate about you. Tell me, are you still chasing something else or are you happy in life? Feel like you've made it and now just keeping yourself busy?

[B]

I'm excited. No, I'm excited about this next phase. I have a family office called Age of AI and I think this is going to be the most significant time in human history. I definitely want to be a part of ushering that in. I mean, it is insanely amazing that you can have an idea now and in five minutes have a piece of software. Have you tried it yet? It's incredible. Which one have you tried? Like cloud code or all of them?

[A]

Yeah, I pay for five different tools personally. And then in my full time role I have another 10 different tools that I use at the enterprise level. So yes, I was up late last night. My wife and both kids were asleep and from 9:45pm until 1am I was just building skills in Claude because I got lost and deep into the rabbit hole and I was like, all right, well here we are, it's 1am time to go to bed. But I just built some fun stuff.

[B]

That is so awesome that you did that. I love that you did that. I was doing the same right before, right before we jumped on.

[A]

It's a mind blowing world. I mean, and I feel like, you know, you and I were talking about it, it's like, oh yeah, I just did that last night. But still there's such a gap, a humongous gap where I go out into the world for coffee or I get lunch with someone and it's like most people in the grand scheme of things still Austin and New York a little different, but most people, like in a suburb, just don't even have the first idea about what's happening in tech right now.

[B]

Going to be, it's going to be a Covid level difference in the world this time next year.

[A]

Yeah. And I think it's already happening, I mean, to many of the points that you've made. Well, John, this has been a really fun episode. Neville said something to the effect Of I think John's the most interesting man in the world. And I agree, like, you are really an interesting person. I think anyone that has a plane and a hangar that can just leave and go wherever they want whenever they want, that already puts you in sort of a category of your own. But I think just the way that you've built successful companies and now you're tinkering with AI at a pretty grand level, it's cool, man. I appreciate you sharing some of your thoughts with us. Do you have any like specific, you know, business ideas right now? And we can kind of end with this and bring the plane in for a landing. Pun intended. Any business ideas that you want to start that you haven't started yet?

[B]

Every week now that it's so easy to create software. I'm starting because right before we jumped on I was playing with this idea. How can you prompt an AI to go make money for you? I think that's pretty interesting. I mean, obviously.

[A]

Tell me when you figure that one out. And the answer.

[B]

Okay, well here's what, here's one thing that's interesting. I hope it's okay to involve you a little bit in the show. I just, I created this thing right before with Zach, my brother. It's called otu.net and you can type in anybody's name and it just shows them unclaimed money. I typed in your name, Daniel. It looks like you got, you got $465. You just need to fill out one form of money that's owed to you and they'll send you a check.

[A]

And then I owed to the like to. Or the number.

[B]

Yes. I think this is just net. Right. I see that you have some crypto services and I think it's. Wyoming has over a hundred dollars. I won't say how much. Then you got something in Illinois. I don't know if it's. Is that true or not? Something that PayPal is holding. It just pulled up a full report. I mean how, how crazy is that? I just was doing on some of my friends too. It's all kind of similar things. And then it shows you based on what it could learn about you, class action lawsuits that you might be entitled to collect.

[A]

I'm sure there are so many.

[B]

There's so many. Right? I mean that's what's amazing. You can just prompt an AI now and have a good generation revenue for you. And so I love those types of ideas. I think that's going to be, that's going to be the Rubicon moment at some point, rather than creating a piece of software, I also need to report, but rather than creating a piece of the software, you're literally going to be able to tell an AI, go produce this outcome. And it will just give you the outcome.

[A]

Now I'm seeing, I'm seeing the 483 or something, but I actually see $2,100. I see some from AT&T, MetLife. Bank of America.

[B]

Yeah, I see a Merrill lynch one too.

[A]

Merrill Lynch. I wonder why I have money that. Please. That's, that's cool. See, I think we, we are already seeing it. But there will be so many one man shop billionaires created in the next five years and I think more wealth created in the next five years than the last 25 combined. That's, that's my opinion. I loosely hold it because so much changes so fast. But I think we're, we're at the precipice of something that's never happened before in history of technology. So it's very exciting.

[B]

What an amazing time to be alive. And we get to.

[A]

What an amazing time. Yes, absolutely. John, this has been such a good episode. I really appreciate you coming on money wise and hope you take care. I'll see you soon.

[B]

Thanks, Daniel. It's been blasted.