My First Million - I Turned $1M into $2.3B (Then Blew It Up and Rebuilt)

Episode Date: June 30, 2025

Want Sam's playbook to turn ChatGPT into your executive coach? Get it here: https://clickhubspot.com/etb Episode 722: Sam Parr ( https://x.com/theSamParr ) sits down with Mike Novogratz ( https://x....com/novogratz ) about risk tolerance and coming back from massive losses. — Show Notes: (0:00) Mike’s first million (8:37) Starting Fortress (13:55) $30M to $2.3B (25:28) Operating system for life (35:41) Being early on crypto (40:26) Risk tolerance — Links: • Fortress - https://www.fortress.com/ • Galaxy - https://www.galaxy.com/ • Business Untitled - https://www.youtube.com/@BusinessUntitled — Check Out Shaan's Stuff: • Shaan's weekly email - https://www.shaanpuri.com • Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents. • Mercury - Need a bank for your company? Go check out Mercury (mercury.com). Shaan uses it for all of his companies! Mercury is a financial technology company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., and Evolve Bank & Trust, Members FDIC — Check Out Sam's Stuff: • Hampton - https://www.joinhampton.com/ • Ideation Bootcamp - https://www.ideationbootcamp.co/ • Copy That - https://copythat.com • Hampton Wealth Survey - https://joinhampton.com/wealth • Sam’s List - http://samslist.co/ My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano

Transcript
Discussion (0)
Starting point is 00:00:00 I'm a good guy to sit around a campfire with drinking because I got a lot of stories. This is Mike Novograts. Mike grew up as a poor kid on Long Island, made his first million working as a trader at Goldman Sachs at the age of 32, and made its first billion at the age of 40. Is that life-changing? Yeah. We were the only company ever were five guys became billionaires in a day. That's wild. Mike is a cowboy in his personal life and his professional life. This guy likes to push it and he's max risk all the time.
Starting point is 00:00:30 Yeah. That's crazy, man. Mike's made and lost a fortune about two different times. We made a bunch of mistakes, and next thing you know, not only aren't you worth $2 billion, but you're going under the billion pretty quick. And you're like, oh shit, that sucks. And what are you doing? Like, what's the lesson to be learned here?
Starting point is 00:00:47 The gap between the really greats and the next level, and I put myself in that next level, is... I feel like I can rule the world. I know I could be what I want to. I put my all in it like no days off. On a road, let's travel, never look at my... I value people who are good operators at life and who live a certain way that I like. I'm dressed like a cowboy today
Starting point is 00:01:10 because I'm like, you're kind of like a cowboy a little bit, like the energy that you have. And that's something that I really respect. But I thought one of the coolest things was how you've made and lost a fortune I think two or three times. You know, I certainly have lost lots of money. That narrative exists.
Starting point is 00:01:26 And one of my kids and a few of my friends are like, dude, this is a little unfair because even at your lows, you still had a lot of freaking money. So your first hit was in your mid-30s, you're at Goldman, right? Yeah, listen, I was a partner at Goldman Sachs.
Starting point is 00:01:41 Goldman is an amazing firm. It might be one of the firms that everyone should study because they create a culture there where maybe not good for your mental health, but good for the firm. People define themselves by what their boss thinks about them. Lloyd Blank,
Starting point is 00:01:58 was like the big guy at Goldman in a later part of my career in every single person what does lloyd think about me you know you gave your heart and soul to this culture of goldman and it's a it's a culture of excellence it's a culture of world-class people you're competing and working alongside the best and the brightest and so you feel like you're on the new york yankees when the yankees are winning and one of the big advantages that is they paid you wildly less than market as you're on your working your way up because you had the right the privilege of being a Goldman Sachs and one day you might become a partner. And so I started at 24 because I had done the army and flew helicopters for a while. And April 1st, 1989, I got my job. And, you know, I moved out
Starting point is 00:02:40 to Asia, which was a great move. The Asian financial crises happened. And what you'll learn in a financial crisis is you're either on the right side of it or the wrong side of it. And if you're on the right side of it, i.e. if you're bearish when the world blows up, you may, you may made far more money than you thought you would for the firm. And so Goldman and me and the team I was with was very lucky that, you know, we got themselves on the right side of Asian Blount and we killed it. And so I became a managing director first and then a partner. What age were you when you left? I think 33 when I became a partner, 34 when I left. And what was your big year? 97, 98. I made a ton of money for the firm. Now in 97, I got paid too much. million dollars, which was by far the most I'd ever been paid, which was a ton of money no matter what you look at. I was a millionaire at 31. I wanted to be a millionaire by the time I was 30,
Starting point is 00:03:37 but I didn't have a net worth of a million dollars until I was 31. But the first year, I really felt like I got paid. I got $2 million, you know, in 1997. Now, me and my team had made the firm like $200 million. And so that was a 1% payout, right? If you work at Citadel or any big hedge fund today, you're broadly getting paid 15% to $20,000. of what you make. Goldman paid us one percent, but you're going to be a partner one day and it's part of them. And listen, you did it make it all on your own. There was a huge infrastructure. Goldman, you know, deserve more than, let's say, Citadel might. But they had this mythology at the place that allowed you to stay there. And I once in my most quit and that the bosses would take you out and say,
Starting point is 00:04:20 oh, you're going to be a partner one day. And listen, I made partner in 1998. And in 1999, the company went public. And listen, anyone who was a partner at Goldman Sachs when they went public in 199 was just lucky because the company had been built over 100 plus years. So all those people who had built that enterprise value that weren't partners that day, you know, we got all their hard-earned effort. We sold this enterprise that was built over 100 plus years to the public. It was one of the coolest IPOs of all time. And the junior partners, we all had 420.2,000. We all had 420,000, thousand shares and the stock was a $55 IPO which traded to $75 and you can do the $400,000 times 75 and we all were roughly worth $30 million overnight.
Starting point is 00:05:09 $30 million is still a huge amount of money. In 1999 it felt a lot bigger. Did you have to vest the, did that need to vest for the next four years? If you were a partner, it was automatically vested but you weren't able to sell it for three, four and five years, I think four or five and six years or three, four and five years. So when you left, you got to keep it. Yes. Okay, good. And listen, I left Goldman in not the nicest of ways.
Starting point is 00:05:35 I had a personal, I kind of blew up personally. I've been there, man. That was horrible. It was embarrassing. It was humiliating. It was, you know, you're letting people down. The guys had made big bets on you. You're like, oops.
Starting point is 00:05:51 One of the great conversations that we'll ever remember. At that point, I was working for a guy named John Thornton, who was the one of the two co-presidents of Goldman, and he'd taken a big risk on me. And I think, John, I just feel so bad for you. He said, bad for me. He said, I'm the president of Goldman Sachs. I'm worth a zillion dollars.
Starting point is 00:06:12 I've got a house here and here. I got a nice wife and kid. Like, you don't need to feel bad for me. You need to worry about yourself. And I was like, it was such a nice thing for him to say. And it was so true. You know, like, I was so worried about, what those other guys were thinking about me
Starting point is 00:06:28 and having letting him down. And instead of saying, oh, my God, like, let your family down, you let yourself down, like, go fix your own shit. I left their tail between my legs and spent a year, sorting myself out. I had a shrink for the first time in my life. I heard you told the story that, like, you said it one time,
Starting point is 00:06:48 and it kind of got glossed over, but it's kind of brilliant. I think you said your brother was near World Trade on 2001, and he calls you, and he's like, I think there's a terrorist attack. I think I'm in this, was he in the World Trade Center? He was like, what do I do? And what did you say your reply was? I was like, you should buy Euro dollars or two-year notes?
Starting point is 00:07:10 And he was like, what the lock? And I was like, maybe get out of the building? And then I was like, maybe I should go back to Wall Street. I literally thought that. I was like, well, partly I then decided to run down. I'd been the army. I want to run down to help. And I picked my kid up, and I'm running down the block.
Starting point is 00:07:24 We lived in Chelsea at the time. So I'm running to the West Side Highway so I could actually see the World Trade Center because you couldn't see it from my roof. And my kids started crying. And I was like, oh, that's not a good idea to run down there with a kid. So I ran back in and watched on TV.
Starting point is 00:07:39 But they wouldn't really take volunteers. The police blocked it off. And I was like, I felt a little impudent, like no way to participate. I couldn't participate financially. I couldn't participate like in safety or physical. It's like when you spent all your life trying to make money, trying to be charismatic, trying to be powerful,
Starting point is 00:07:57 and you're like, fuck, none of this matters right now. Yeah, and so I literally remember saying, I want to go back to work on Wall Street, and there's another chapter left in me. Because in between, I was looking at things like outward bound or just a whole different career path. I was like... You were going to be like a camp instructor?
Starting point is 00:08:13 I was going to try to run outward bound. You know, there was a, you know, you're looking at, you got headhunters, like, you know, what are jobs that you could qualify for? I remember I was the president of Goldman Sachs, Latin America. I was a young partner from Goldman. And so, that's wild. Camp instructor was below my pay rate at that point.
Starting point is 00:08:30 But I was trying to think of other ways to contribute to my life and to society than Wall Street. And that 9-11 thing was like, you know, go back to Wall Street. You got another chapter. And that's where you start Fortress? I actually, to be fair, didn't start Fortress. My partner, Pete Brigger, who was a partner of mine and a good friend both from Princeton, Goldman Sachs. and in Hong Kong, he had called me up and said, hey, why don't we partner up? And Pete's an amazing guy.
Starting point is 00:09:01 He said, how about this? You're pretty, you have a fun life and I'm a pretty good investor. And you're a decent investor. Decent. Thanks, Pete. And he said, we'll go together. We'll split it 50, 50. Half of what I make, half of what you make.
Starting point is 00:09:16 And at that point, his stock was trading at a premium to fair value. my stock was trading a huge discount to very, yeah, you know, like, and that he would make that call meant the world to me. And so I say, I'll do it. And so the two of us were going to partner up in something. And Pete had known Wes Edens, who had started Fortress a few years earlier. At that point, Fortress was probably 80 people in about a billion dollars acid. And it was a PE firm or a hedge fund? It had been a PE firm. And you were buying any type of businesses? Well, it was a PE firm that Wes ran with a guy named Randy Nardone and Rob Kaufman, who are still friends of mine and partners and some other things.
Starting point is 00:09:54 And they were doing mostly structured credit type P.E. But, you know, Wes was a genius. He, like, came up with the idea of, let's buy all the cell towers and then think of cell towers as a reet. And so he would look at business opportunities and literally craft companies that would then become a billion-dollar companies. And so we thought Pete has a real expertise in building a credit hedge fund. I was going to build a macro hedge fund.
Starting point is 00:10:19 And the three of us sat there. and said, one plus one plus one will equal 10. No one had ever taken a hedge fund or private equity company public. And we said, let's build a company where we all build our own businesses. And to be fair, 90%, 95% of the time we spent a loan. We didn't like each day, what are we doing today?
Starting point is 00:10:41 I built a company, Pete built a company, and West built a company that we all put in the same box. Did you have to come up with any of your own capital to join? I did. I did. And I actually didn't have that much capital. You know, you, you, when I said Goldman had, you know, we got $30 million after Goldman, well, that's pre-tax and the stock goes down.
Starting point is 00:11:02 And I think Pete and I put in roughly $10 or $15 million, this is all I had. So you were worth $15 or $10 and you put all of it into Fortress? All of it into Fortress. And actually borrowed some, I think. And you're what, 37? Yeah, 37. And, you know, started a hedge fund. and I started a macro fund.
Starting point is 00:11:20 Peace started a big distress fund, and Wes continued to build his private equity business. And part of our ethos was, if we do what we say we're going to do, people will trust us. I learned that at Goldman Sachs as well. Goldman Sachs Asset's management business didn't have the greatest returns, but they had lots of money because people trusted them. And so how do you build a sense of trust in investors?
Starting point is 00:11:43 It's doing what you say you're going to do. No one expects you to win all the time. what was wonderful about fortresses and very cool is that over the first five years, really 2002 to 2007, Pete's business, I don't think lost money in a month. He'd buy broken debt. He'd give loans to people. You know, I called him a loan shark. Like if you couldn't get a loan from Deutsche Bank, he came to Pete.
Starting point is 00:12:10 Like private credit. Now private credit's a huge business, but he was early in private credit. And so he built this very diversified portfolio of loans. Wes continued to do his stuff, and literally his track record just kept going up and up. And I had a very good run as a macro trader. And so by the time we went public, my macro fund in those five years was a top performing macro fund. You know, it was in the top 5% of macro funds. Pete had never lost money in a month.
Starting point is 00:12:43 And Wes's track record looked like Warren Buffett's. And that 15 million that you invested or 10 at its peak, what do you think it was worth? Well, when we went public, we were the only company ever. And I think to this day this holds where five guys became billionaires in a day. So in roughly 10 years, you turned one million into a billion. 2.7, 2.3 billion. That's what the – we're sitting around our office after we rang the bell at the stock exchange. And I got my two young daughters.
Starting point is 00:13:10 And all of a sudden, Bloomberg puts a picture of Wes E.D., I was like, oh, shit. Wes Eden's 2.3 billion. And then a picture of Pete Brigger. Pete Brigger, 2.3 billion. Picture of my, you know, I think Wes owned a tiny bit more. So Wes would have been 2.4 billion. And then Pete and I own the same.
Starting point is 00:13:25 2.3 and 2.3 billion. And my two, like, 9 and 10-year-old daughters, looked at each other and high-fived. Because we had never talked about money, right? You know, like 9 and 10-year-olds. Was there any difference? Is there any difference between making, let's say, $30 million? than from two point whatever? I think that fortress frenzy of us becoming rock stars almost
Starting point is 00:13:51 because we were the first company to take a hedge, we're the first guys to take a hedge fund, private equity company public, and that we were all on such a high. It didn't last long because the O8 financial crises happened. You get treated a little differently. All this are you getting calls from the president of university who wants to sit down and talk with you.
Starting point is 00:14:09 You're getting invited to cool dinners and, And so it goes to your head a little bit, and you're not ready, ready for the rush of excitement around it. You don't feel that different. I think the same friends and, you know, but there's a little bit of everyone gets a little bit full of themselves. Did your life stay the same, but the people who wanted to talk to you change? Yeah, you're getting emails and calls from people you haven't seen in years and people you don't even know that say they know you. Yeah, you get this. There's a, especially because it was public, right?
Starting point is 00:14:41 If it doesn't quietly, no one would have known, but we were like on newspapers and magazine articles. And so, and it goes to your head a little bit. And then, you know, the wonderful thing about being having six brothers and sisters is, they don't treat much differently. They're, like, excited for you, but they. Well, and you have six or seven, you have a bunch of siblings who are also ballers too.
Starting point is 00:15:00 And friends. And so, you know, and then the markets always take their pound of flesh. You know, we made a bunch of mistakes. 08 happened. And next thing you know, not only aren't you worth $2 billion, but you're going under the billion pretty quick. And you're like, oh, sh- You lose it a comma. Oh, shit, that sucks.
Starting point is 00:15:21 Some of this goes back to, and this is going to sound crass as heck. But if you were a kid in high school that played sports and the girls liked or the guys liked if you were a girl and had a decent social life and didn't have a chip on your shoulder, it doesn't seem like it success is a little easier to handle. because you were used to it. And it's not the same magnitude of success, but like if you got lucky with the girls in high school, you usually turn out to be okay. Like, it's often you see the problems of people that really have a hard time adjusting
Starting point is 00:15:56 was when they were misfits or social, and that chip on their shoulder drove them to this craze success. And you, the reason I'm interested in you is because you've won in a bunch of different parts of, life. So you were a great wrestler. You went to Princeton. Like you did a lot of amazing things. But then you, you, what's funny is because your personality is so loud and because you're so funny and tell these crazy stories, like you talk about trading and you're like, oh yeah, I forgot. You actually had to be skilled at something. The people who are around you, what do you think
Starting point is 00:16:28 they would say you're good at? I have a weird insight into looking at what the future is going be. You know, it's called pattern recognition. I can look at the charts and say, this is going to happen, or I can synthesize information well. And so I'm a good speculator because I see the future pretty well. Do you read a lot? I used to. I watch a ton of TV now, but I read a lot of, like, nonfiction stuff that's coming through my desk all the time, right? So I keep up on news in the world and talk to people. Most of the great CEOs read a lot. They're curious. I'm curious as heck. I get a lot of my curiosity and learning from conversation, from this amazing network of people
Starting point is 00:17:10 that I've met in the world, and I'm learning all the time. I literally had lunch with Goldman's chief information officer. So he's got 19,000 of Goldman's 45,000 people that worked for him. And, you know, it was a master class in AI. And so then I'm like meeting some other guy in AI.
Starting point is 00:17:30 And so I'm learning AI from reading articles, playing with it, but mostly finding out the world experts and learning from them. And that's the way I've been learning as I've gotten older. So you think that people would say that you're good at seeing patterns? What else would they say? You think they think you're good at? And I'm a good storyteller.
Starting point is 00:17:48 And so why that's been important is crypto, in the last 10 years, has been about narrative, right? It has been about the story of understanding the world and then telling that story. And I think I'm not. been unbelievably well suited for this moment of time to be a crypto CEO because I'm a good storyteller, right? How do you convince someone to buy Bitcoin? You've got to tell them a story. What about being a good trader? Because you were actually a trader for a long time.
Starting point is 00:18:17 I still am a trader. That's a hard job because you have to, first of all, develop a process, an internal algorithm that wins more than it loses. You've got to be really honest with yourself. I good at this. It's not, am I intelligent and am I smart, but am I good at this? Am I good at taking this information and making bets on it? And even if you are, then you need to develop a discipline that allows you to make sure that your guesses are in your portfolio. There are so many people that say, oh my God, you've got to be short the dollar right now. The U.S. is on a downtrend, right? Trump is pissing everybody off. The short dollar is. is the biggest, easiest trade to see.
Starting point is 00:19:06 Every single macro investor, almost every single investor right now, believes that you should be short the dollar. And it's a maximum conviction belief. I would bet if you took all their portfolios, only 40% of them have a really big position. It should be tautological that if you're bearish, you're short,
Starting point is 00:19:29 and if you're bullish that you're long. But it's not because of fear. What if I'm wrong? And so much of trading is anxiety management. So much is how do I overcome my fear? I heard a guy the other day say anxiety is just when your brain is a lot bigger than your balls. And so we, listen, anxiety is real, right? Like there is this, the lion that shows up and you go into the fighter flight.
Starting point is 00:19:59 In trading, you see the lion all the time. And you get nervous when the market's. going higher and you're long, well, what if it goes back down? I'll give my money. And so there are all these different reasons you get scared. How do you learn to trust yourself?
Starting point is 00:20:13 That's a really hard process. What I've learned from the best, and I'm really good at this, but there's a group that's better than me, and I think about this all the time. Let me say this. You're good at being a macro trader. But does that mean you're good at managing anxiety?
Starting point is 00:20:29 The whole process of seeing the world and then betting on it and making money from it. And so there are 25 macro traders that people probably heard of Stan Drucken Miller, David Tepper, Paul Tudor Jones, Lewis Bacon, you know, Alan Howard, Chris Rokos, there's a bunch of people that are great at this.
Starting point is 00:20:45 The gap between the really greats and the next level, and I put myself in that next level, is discipline. And so you have to have a set of rules that you follow. Well, do you consider yourself a highly disciplined person? I think I'm a really hard working person who has,
Starting point is 00:21:03 And I was really disciplined at parts of my life. And I think I have sporadic lapses of discipline, partly because I have this really diverse group of interests. And I get excited. I'm a people pleaser. So I'm trying to help things out, people all the time. And it's a prioritization. Like Stan Druckler, for instance, who I think is the best, or, you know, David Tepper's pushing on it. But the best trader, certainly of his generation, Tepper's a little bit young.
Starting point is 00:21:33 32 years, never lost money, compounded over 30%. Everyone in our seats look at him as like, the guy. The guy. A ton of integrity on how he lives his life and how he lives his portfolio. When he was managing other people's money, he never golfed during a workday. And he loves golf.
Starting point is 00:21:54 But what you said, you had this great quote, you go, you were quoting Napoleon or someone, but you said, I hire lucky generals, not skilled ones. So this was, how did I learn that I had the right to be good at this, right? I was making money lots and I was like, yeah, everyone has a bit of imposter syndrome. And Ahud Barak who had been the prime minister of Israel, I'd hired as a consultant. How do you hire the prime minister of Israel as a consultant? One of my investors said, you need to meet Ahud Barak.
Starting point is 00:22:21 And Houd Barak was looking ways to make money and he had just started this business. And he had two clients, Lewis Bacon, who was a multi-billionaire, you know, one of the pantheon of the greats. And Bruce Covener, multi-billionaire, one of the pantheon of the greats. And Mike Norgratz, who was a little peanut at that point. What was his rate? Maybe it was $200,000 a year or something. So you got the former prime minister for $200,000 a year to give you feedback and advice. That's pretty good deal.
Starting point is 00:22:49 I just remember thinking, I've read the same consultant. He only had like three clients as two of the world, like literally the great traders of all time, Bruce Covner, who built Kackston and Lewis Bacon, who built more capital. And I'm sitting with a hoot for lunch, and he said, you don't know if I figured you out. He said, you know, you're not so smart, but you're lucky. And I was like, that's the compliment. He said, don't worry about it because, you know,
Starting point is 00:23:17 I was just with Lewis Bacon and I spent time with Bruce Covenner. He said, Covner might be smarter than you, but, but, you know, all of you guys have an intuition. You know, and they gave me this quote from Napoleon. He said, and of course I didn't know French. He said, I forgot you're not so smart. You don't know French. You're just a son of a bitch.
Starting point is 00:23:31 And Barack, at least allegedly, had the highest IQ of anyone in the Israeli military. And he was the most decorated soldier in the Israeli military. He was a wonderful guy, charming. And he said, you guys have an intuition, a pattern recognition, an ability to sense where things are, like a general did. And that's your intelligence. Instantly, I was like, that's why I'm right more than I'm wrong.
Starting point is 00:23:56 I never knew why I was right more than I was wrong. It's easy to know you're being commercial, right? You and I can be commercial. If we can make these cups of broth for 50 cents and sell them for $2, we're both going to say, how many can we sell? Right? That's not hard. But why should I be able to predict where dollar yen is going to go in a year better than you?
Starting point is 00:24:16 Are you able to do this in other facets of your life where like, man, I met this person. I predict that they're going to face these problems or whatever. Well, what's interesting is without being conscious of it, like I've invested in a few independent movies, nobody makes money in independent movies, like almost nobody. And I've invested in two of the top three selling independent films of all time. Independent films that sold for the top prices, right? Birth of a Nation still, I think is the highest. 19 or what?
Starting point is 00:24:47 19 million that sold for, I think. 19 million. And then there's a movie called Assassination Nation, which didn't do well in the box office, but sold for like 13 million. Like those are two of the top, you know, five prices for independent movies. at least they were. And was that just luck or was it intuition?
Starting point is 00:25:04 I mean, it's not luck if it happens twice. Right. And so for me, that conversation with Barack was giving me confidence that my decision process wasn't random, that there was something in it. So I went back and I thought about, like, how do I make decisions? And it is at the intersection of lots of data and a gut feeling. and there's that, I think, moment. And so once I understood that, I was much more confident
Starting point is 00:25:33 in telling investors how I made decisions. My hedge fund went from $300 million under management to $2 billion, and my performance went straight up over like the next six months. But mostly because investors could feel my confidence. And so the lesson for you or for listeners is spend time figuring out what you're good at and where that comes from.
Starting point is 00:25:55 and not everyone has the same skills. Where does it come from for you, though? I mean, because I remember reading about, I'm not in the finance world at all, but I read Blackfish, which is about Steve Cohen, and they told stories about how in the 80s that there was a physical ticker, and he would like, he could just hear the rhythm of the ticker and make,
Starting point is 00:26:16 and I'm like, that is just so vague, and it's a pain in the ass because I'm like, you're explaining it like an art, but I want it to be more of a science because I want to learn. But that's how you're describing it. Like, it's more of, it's very artistic. For me, the type trading I do,
Starting point is 00:26:30 it's very intuitive and it's very pattern recognition. If I went blind, I couldn't trade. I need to see the ballet of the charts. There are other people that do things very differently. Like, the interesting thing about training is there are 1,000 different ways to approach it. What does Steve do you? You were saying, but I know Steve pretty well, but I don't know his exact process.
Starting point is 00:26:50 But I would tell you he's one of the most competitive guys out there. He used to go on vacation and have. have all his screens set up. And if he didn't, he wasn't in feeling things right, he'd fly right back to get it to his desks. Like he was obsessed with beating the markets. Are you, you think you're competitive? I'm not as competitive, which is interesting.
Starting point is 00:27:09 When I think about like with Stan Drucker and Lewis Bacon, and like why those guys have been in that, and maybe one day I'll catch them, but I'm not in their category at this point. They're more competitive than me. They just, I mean, Lewis Bacon, I remember playing croquet against them. And I'm like, how's this guy
Starting point is 00:27:25 killing me in croquet. Well, he had hired the world's best croquet guy to teach him. He doesn't like to lose. There's partly, these guys are ultra-competitive, but they also are ultra-discipline. And those two cross-factors. Creates a maniac. Well, creates an amazing performer. Yeah. Maybe not the easiest person to go to cocktails with. Sometimes they are something, but like an amazing performer. And I don't want to discount. I've had a, amazing run of success at trading. I just know myself, as I compare myself to the other guys, a little more disciplined.
Starting point is 00:28:03 Now, I would probably argue I've had more fun. I've done more different things than most people. But again, each person makes their own decision on what path they want to take. And I'm not making a value judgment on how people live their lives. The key is to figure out how you want to live your own life, but figure out what you're good at. And again, that comes from mentors. it comes from sometimes chance. Without that conversation with Hubrach,
Starting point is 00:28:28 I was miserable because I was feeling so much pressure. And I remember telling my wife, I said, I might even just shut this hedge fund down if I can't have more fun. And I was winning, but I was feeling so much pressure. And I think I was feeling pressure because I didn't know why it was good. And that literal conversation over lunch
Starting point is 00:28:45 unlocked this story in me that said, hey, this is why I should, this is why I win. And that was intuition. You're just good at, you feel certain things and you should trust it. And it doesn't come just, like, you don't get it from sitting in a box. There's a tremendous amount of information.
Starting point is 00:29:03 I'm shoving in my brain, right? Looking at charts, talking to people, understanding psychology, looking at, you know, who's long and who's short. There's tons of stuff that goes into the algorithm, but it was at that intersection of the intuition. It's all in the part of your brain that you're not tapping normally.
Starting point is 00:29:19 A lot of it's historical, too. Like you see things, they repeat themselves. Yeah, I, I heard one of my heroes is John Rockefeller, and I was listening to Business Untitled, and you're like, when I was in fifth grade or eighth grade or something, I wrote a paper on Jadendee. Yeah.
Starting point is 00:29:31 And I thought that was cool because he's a fun-ass dude to learn about. And you also, you and your partner, West, did the train thing. West did the trade thing. I was a cheerleader and an investor. But, yeah, that was fascinating when I went down there and I was reading about Flagler. Yeah, he's a man. These guys are hardcore.
Starting point is 00:29:47 Yeah. I went and talked to a bunch of friends of ours. You and I have some mutual friends. and I want to tell you what they said. They go up. He's max risk all the time, his entire life. He takes tons of risk and he lives life on the edge. And another person said, he's blown up a couple times and he's won a lot more.
Starting point is 00:30:09 I'm amazed at how good he is at managing risk. And I actually talk to some of the guys you work with, and they also use the word risk constantly. It's hard to be in the crypto business and not to be comfortable with risk. Like it's an asset that, you know, Bitcoin went up and crashed down. Yeah, I think it's bigger than Bitcoin. I think that you got lucky that Bitcoin exists when it does. I think that you're a guy who you enjoy risk. You enjoy, I think you were telling you.
Starting point is 00:30:35 I heard a story about how you said, like, you are a 37 out of 40 in terms of like some type of personality test of freaking rules. And you're like, it's funny. My kid is the exact opposite. And then you hear I read the New York or some article where they're like, he flew. a helicopter down the street, like, during the Princeton's graduation. Like, there's clearly, like, this thing of, like, this guy likes to push it, and he's pretty comfortable teetering on, like, big ruins. And so are you, for your personal finances, are you at risk often?
Starting point is 00:31:07 So part of it is there's this balance between, like, yeah, there's an adrenaline need. Like, I like adrenaline, like, in sports and in trading and, you know, it's a dopamine addiction. if you want to think about it. But part of it is I like my life. And I was a helicopter pilot at Fort Rucker, Alabama, and I made $18,000 a year after tax. I remember because I had $1,500 per month paycheck. Pat Tierney, who's a buddy mine still,
Starting point is 00:31:38 was one of my buddies down there. And we had the time of our lives. When I look at how much fun and how much I enjoyed that in the middle of the ugly corner of Lower Alabama, right, the wiregrass it was called by Dothan, with 700 other guys and almost no women around because all the women have gone off to college and there are 700 guys and a few women at flight school,
Starting point is 00:32:03 we still had one of the time of our lives. So when I think, was that year better or worse than the year I made lots of money? I can't tell. Like, that was a great year. And so I think if you enjoy your life, it's easier to take risk. If I lost my money, it would hurt my ego for a while.
Starting point is 00:32:21 I would be embarrassed. I'd be frustrated because all the money really does at one point is to allow you to help other people, right? And that's both a blessing. It's a huge blessing, but it's also a lot of responsibility and sometimes it's a pain in the ass.
Starting point is 00:32:37 And so I actually don't think I've tied how I live my life on a year-to-year basis to money. Now some of my friends say, oh, that's bullshit. Look at the parties. You throw you spend lots of money.
Starting point is 00:32:50 I do spend lots of money. But at two tons of parties, when I didn't have a lot of money either, I just threw cheaper parties. And so I think so much of being able to take risk is being okay with your life and not being defined by just your money. Have you met a guy named Brad Jacobs? No, I wish I have. He has a book. I've never met him. I've read his book.
Starting point is 00:33:10 It's called How to Make a Billion Dollars. He's created, I think, six billion dollar companies, like XO Logistics is one of them, if you ever heard of that. like these like huge like $10 billion logistic companies. And his whole shtick was he fragmented industries, bought all of them, operated them well, took a public, whatever.
Starting point is 00:33:28 And he talks in his book about how he was like, I researched like crazy. Like anytime I get into a business, I research like crazy. So I read all the books. I use TGIS or whatever else, like the services and are alpha sites, whatever they are and like I hire experts.
Starting point is 00:33:40 But then I go and talk to the employees. And I just research. So it's like I'm really confident that this is going to work because I've talked to literally 500 people and I have all these notes. what I've noticed a pattern with you is that you don't I don't know if you call it research
Starting point is 00:33:53 but you talk to a lot of people and so like I just on the way here I was hearing a story about how like your roommate was Gloria Vanderbilt's son or something like that. It was. Like so that's like pretty magical to be around and hear stories of that family
Starting point is 00:34:05 and then like your other roommate helped create Ethereum and then there was like this other story this other story there was like 20 stories where I'm like what the hell like it's like you I'm a good guy to sit around a campfire with drinking because I got a lot of stories.
Starting point is 00:34:19 But there's just so many times. It's like, normal people would be like, I know a guy, you know, I sat at a bar next to a guy and he did this. You just have all these stories except that they just happen to be like these like wild crazy people. Who, what was the story about how you first heard about Bitcoin? So Pete Brigger,
Starting point is 00:34:34 who had been my, he lived above me my freshman year at Princeton. He lived in the room above me. This storm was amazing. We had a pretty cool little group of people. Right? Is this wild? It's like the greatest storm on Earth.
Starting point is 00:34:46 He lived above me. How many billion? are from that door, what do you think? No, seriously. At least three. For real, in that dorm. But he's the reason I got my job at Goldman Sachs. I was literally wandering around Bleaker Street, a little drunk,
Starting point is 00:35:01 and I ran into him, and I was interviewing for jobs. He was like, bullshit, you got to work at Goldman Sachs. And I was from the Army, and so he got me an interview at Goldman Sachs. And 41 interviews later, they gave me a job. And then we lived in Hong Kong together, and we slowly became very good. friends. I'm the godfather, his youngest son. Then we did Fortress. And he was the guy that was the distressed debt investor. Well, because he made a promise to his wife that at one point they'd
Starting point is 00:35:30 moved back to California. He moved his entire business or the bulk of it to Stanford area. Yeah. And what year was that? This probably would have been, he probably moved his business out there 2010 or something. All right, good timing. And, and, but he's not a tech guy. But his brother-in-law was a tech guy. And the, the group of friends, he had were tech guys. And they all started talking about Bitcoin. And Pete wanted to be part of the, part of the clan. And so he called me up, he said, I'm hearing about this thing.
Starting point is 00:35:57 Bitcoin, all my smart friends are doing it. What do you think? And I never heard of it. And I quickly did a Google search and asked around. This was in 10? This was in 2000, 2012, 2013, maybe. Bitcoin was at like $96. So it was nothing, really.
Starting point is 00:36:14 I mean, there's not, there would have been like Bitcoin.org or like some forum. There wasn't a lot, but it was online. The Chinese had just started buying it. And I made a thesis. I said, how we got to buy it? And we started buying some of it. My friend Jeff Lowe, who's become a great investor, was working in my family office. And he bought my first Bitcoin for me.
Starting point is 00:36:32 And then Pete and I kept talking about it, and we were like, maybe this should be bigger than just us buying a little bit of it. So we called a third friend, Dan Moore, another Princeton guy who I had invest, who had, you know, had a similar, went to Princeton. He had worked on Wall Street. He worked at Goldman. he worked at Tiger. I had invested in his first hedge fund. And he was on the sidelines in between, you know, after 08, his hedge fund didn't do well.
Starting point is 00:36:55 He was trying to figure out what to do. He did some cool stuff in Argentina. He researched this for a while and came back and was like, guys, this is going to change the whole world. And Dan was really confident and was willing to put a whole bunch of his net worth into this thing. Pete and I were wealthier because fortune has gone public than Dan at the time. And we're like, if he's putting out of the time, much in. We need to put at least that much in. You know, it's the way guys think. And so we all
Starting point is 00:37:22 roughly put similar amounts in. Was it like eight figures? Uh, or you can even say that? It was, it was seven figures. Seven figures. But it was a significant amount in dollar terms at 100, but not in our net worth terms, right? We were very wealthy guys at the time. And it's one of the reasons we were able to hold it so long. Because even it went up, if you're a young guy and you put $10,000 into something and all of a sudden's worth a hundred thousand your friends like dude you have to you got to take some you can buy you can buy you your girlfriend wants you to buy you know like there's so many reasons you're going to sell that thing and almost nobody can hold but if you're already having a lot of money it's just another investment and so we get a lot of credit for
Starting point is 00:38:06 having made lots of money in crypto it was easier having started rich and it's got me thinking why this world is so off sides, when you're wealthy, you have assets. Assets are basically chips on a table. You know, I bought SpaceX when it was 120th was today because everyone was like, ah, you got to buy some SpaceX. And you look, they're like, Elon Musk is killing. He's brilliant. Let me get some private SpaceX. And so all of a sudden you make, you know, 100 million plus in SpaceX. You didn't do anything other than put a bet down. And so getting money, and getting network makes making money so much easier. It's almost unfair.
Starting point is 00:38:51 It's why Pickney wrote that book. He said that there's no way the rich, poor gap ever comes back into balance because once you're wealthy, you have such an advantage. And the advantage isn't just capital. It's capital in network. And one of my strengths is I like people, I like cheering people on, I like talking about people, and it makes it easy to make friends in network.
Starting point is 00:39:12 And through that network, you learn. stuff. So my, I'm, for our podcast, my listeners will make fun of me. I, I own a company now that does well, and hopefully that's going to be a huge home run. But my liquid net worth, I just do basically the SMP 500 and bonds. You invest like you're a, I got a white guy from Missouri. Oh, yeah. Look, it's worked out. Boring. Which means I've, I've offered about 90% of hedge funds, so it's worked out. But like, listen, it's been a great. Yeah, I've like, I started making money in the Gray's Bull Market of all time. And do you, for your personal finances, do you have any boring stuff? Or are you all we, are you active for the whole thing?
Starting point is 00:39:54 No, I, listen, I have a chunk of money in, you know, these credit funds, like the one Pete Rand, which are private credit funds, which, you know, roughly have done 10% plus a year compounded. And you can compound a piece of money at 10% a year for a long period of time. rich real quick. And so I have someone private credit. I have a lot of my own company, then I trade currencies and stuff on my own. And then I have a bunch of private equity investments and venture investments. I own a chunk of Bojangles, the chicken company that got announced yesterday that the group that owns it is putting it up for sale. So hoping that sells for a high price. But I haven't really ever done bond stocks, partly because that's what I do.
Starting point is 00:40:42 Yeah. And my money has often been tied up in the enterprise that I'm engaged in. I had fortress. I own a lot of fortress stock. I guess you've been ill-liquid, like, for a large portion of this. I probably have run the lowest liquidity to net worth ratio of anyone who's been on your podcast. Can you tell me more about that? You know, it's not necessarily what I would want it always.
Starting point is 00:41:03 I've always had a lot of faith that I'd make money. And so I've always either wanted to live a big life and also make a lot of investments. And so you spent, you just spend a lot? Spend a lot. Live large, I invest large, and I always think I'm going to win. And so in 2021, we thought we were going to be able to take Galaxy public and I was going to get a lot of liquidity. And it turned out we took a little too long to get into the SECQ. Administration changed. Gary Gensler shut the door. And so for four years, no liquidity at a Galaxy.
Starting point is 00:41:31 You know, my other stuff, I made some good investments, some bad investments. And it didn't really change lifestyle. And you slowly start burning the furniture of liquidity, right? And so we just did a deal. We took some ships off the table in terms of liquidity. Did you live life on the edge? I mean, I think I admire, like, your ability. Like, I'm an adrenaline seeking, too.
Starting point is 00:41:53 But I'm also way more risk adverse than you, I think. And I, but I admire people who are into risk because I think it's held me back. I think one of the things that people say you blew up twice. I, listen, I had a personal shit to deal with and I lost my job at Goldman Sachs. Actually, to be fair, I resigned. But that was embarrassing because I was on a high flyer track there and I loved Colton Sacks. And so that was painful. Coming back from that gives you a lot of confidence that you can fall down and like you can lose money.
Starting point is 00:42:26 It's not the end of the world. You're going to, you got to learn how to get back up. And being a wrestler teaches you that, like no wrestler wins every match. Kail Sanderson did in college, but then he lost an international. Like, you know, no one wins every match. and learning how to come, and I lost a lot. Learning how to come back from losing
Starting point is 00:42:45 is one of the most important things because losing doesn't mean you're a bad guy, it doesn't mean you're a shithead, doesn't mean you're not competent. It just means you lost that game. And I think Nadal, when he left tennis, gave the best, he was like, you know, I think he lost 48% of the points he played.
Starting point is 00:43:01 He was the greatest tennis player of all time or one of the top three. That process of stumbling, and coming back. And I think a lot about how I have managed to do that myself because I often ask to help people to think through it. What? Like a downfall and like, a rebirth?
Starting point is 00:43:22 Part of it is take some time off and do some work and understand like what the hell happened? Like how do you, most people don't spend enough time to figure out who they are. Like literally trying to understand like who they are and why they're who they are. It's always your parents. parents, you've got a relationship with your mom and your dad. Whatever the story was,
Starting point is 00:43:43 dad disappeared, processing that's the human condition, right? And trying to understand what moves you. Some people get there and the whole world. Other people just make progress getting there, right? I think I've made progress. I'm not sure I've ever gotten to enlightenment by anything, not even close, but I keep making progress and going on that journey. And there's lots of ways to go on that journey, right? It's through getting a shrink, through meditating, through prayer, through ayahuasca or psilocybin journeys. Like there's radical ways, there's subtle ways, there's taking time by yourself. But it's investing in yourself. Most people don't invest in themselves.
Starting point is 00:44:24 I was asked a room full of 800 wrestling coaches, how many in the last five years it's been one week with just themselves and not one hand run up? Not one. You do that now? I try once a year to spend a week by myself. My friend Chris, who has a public trade company, he's like, I mean, I screw up all the time, and I always try to journal, what's the lesson to be learned here? And I thought that was like a really good way
Starting point is 00:44:50 of asking himself that question. What questions are you asking yourself during that seven-day solitude? Well, I did the silent meditation in Cardiff, England. You sit there for fucking 11 days meditating. You can't read, you can't do music, you can't exercise, you can't even masturbate. I mean, it literally is for 11 days. Your back hurts. You starve.
Starting point is 00:45:18 Do you set goals like this? Like to have such a full life where you're running a, I don't know how many people work here, 200 people, a lot of people. 600. 600. Oh, my God. I didn't even realize it. And you have all the, you have a lot of shit going on. But then you're like, I do this weak meditation and then this party here.
Starting point is 00:45:35 Are you setting? like at the end of the year, this is what a win would look like. We do. We do set goals. We've got a management team that's got agenda of things that we wanted to happen. And I think the crypto business is in such an interesting, both crypto and the data center business. We have two businesses. Both are at the forefront right now of like explosive change. And there's a ton to do on both of them. And so when I think about my time for the next six months, galaxy is going to get a ton of my time. There's been times when we first started,
Starting point is 00:46:11 it was a smaller business. My philanthropy got a ton of my time when I started doing criminal justice. So I've dialed back my participation in philanthropy solely because this 600-person baby needs a lot of energy. And so I do think of it that way. But my brain, you know, like how do I have fun?
Starting point is 00:46:30 If I make this much money, what are we going to do with it? So my son and I are brainstorming on like a cool project, fantasy project that you would do if you actually had X hundred million dollars to give away to one thing, you know, what could you do to make New York City better? And so, like, and I'm on perplexity, I'm trying to figure out, I'm working with people. And so I multitask in that respect, but I got goals.
Starting point is 00:47:00 There was that, do what I say to what I do. I'm much better talking about, like, the meditating and the exercise, and this is where the discipline, my wife wakes up every day, 6.30, and meditates an hour, and it meditates an hour at night, and doesn't miss. And I'm just like, she's like a mitrono.
Starting point is 00:47:17 And I'm like, I know that would be good for me. And I do, I'm gonna take once in a while when I'm stressed like in meditate. But it doesn't seem broken. Yeah, when I break, I figure out how to fix myself, but no, I don't feel broken. Yeah, but on this other podcast you did, you were like, oh, I went to a therapist
Starting point is 00:47:32 the first time ever, and the thing was like, I gotta love myself, forgive myself. And you're like, that was a huge breakthrough. And I'm like, in my head, I'm like, playing an armchair expert here. But I'm like, you're doing it again. You know what I mean? Like, dude, like, people have a hard time changing patterns. One of the things you'll learn as you get older is that you see very few people that actually do enough of the hard work that they do change. And most of the times you see those people is when they literally hit some horrific rock bottom. that the only way to live is to change, right?
Starting point is 00:48:07 That's the whole AA cycle where they just give up and say, oh, Cal, I'll do what you tell me to do because I got to change. Change is hard. Even subtle change is hard. And again, if someone's living their fullest life, maybe they don't want to change, right? Yeah, I mean, I love hearing about the shit because I think that, I think that, you know, this is going to sound pompous of me. But in my head, I'm like, I can be like, you know, he's, you know, he's, you know, I'm 35. So I'm like, okay, he's 25 years ahead of me.
Starting point is 00:48:38 And like, we both can't hear. Yeah, we're both a little bit deaf. And I came from a blue collar like a family. And I think you talked about Princeton about like, oh my God, I thought I was the shit. And then I got around people that like kind of were the shit. And I'm like, oh, fuck. And so like I've like felt that like many, like I hadn't been in New York City until
Starting point is 00:48:56 I was like 26 years old, hadn't been on an airplane until I was 21. And so like I always felt like these. That line in New York, if you can make it here, you can make it anywhere. there's nothing like New York City because you're never going to be the guy. Like I go home and I'm like, I'm the man. And then I go to New York, I'm like, and I'm like looking at apartments
Starting point is 00:49:13 and I'm like, I'm nothing. But it's both so liberating and so awesome because, I mean, you go to a Knicks game. Oh, dude, we were supposed to do a podcast and you canceled. And that night, I turned on the TV, I see Timothy Shalamein, I see the Jenner girl, and then I see Mike.
Starting point is 00:49:31 And I was like, that motherfucker. We were supposed to do a thing. And then I was like, my wife was like, can you blame him? I'm like, no, I can't. Knicks in the playoffs is as much. This site city erupts when the next to the park. You had like, there was Timothy and then you. We got good seats.
Starting point is 00:49:47 You were like the man. How much is the playoff seat costs? To doubt where he's, I imagine. So those seats are free. And if you want to buy front row in the playoffs, you know, they can cost as much as $50,000. That's what I thought. The second row, the guy who sat next to me, I think paid $15,000. Wait, yours were free?
Starting point is 00:50:04 Well, no, ours, we have season tickets. Okay, good it. And so you just pay the normal whatever Knicks charge you for playoff tickets. That's crazy, man. And so. Do you see Ryan Cohen is? Yeah. Billioner Ryan Cohen.
Starting point is 00:50:15 I mean, I don't know him, but I know who he is. And I saw him sitting right in front of you during a game. And, like, Jalen Brunson, like, fell in his lap. And he didn't break eye contact from the beautiful woman he was with. He just, like, he had the conversation the whole time. Those seats are fun because you always have the celebrity sitting in front of you. I went to one game. just a regular season game.
Starting point is 00:50:35 And DeVito, the Nigerian superstar, you know, there are two guys in Afro beats, right? Davido's one of them. The other guy's Burnaboy was there, and I didn't know what he was, but he had a great chain. I like, dude, where'd you get that chain? He's got.
Starting point is 00:50:52 And I went to get a beer, and I was like, you want a beer, a Coke or something? And he did it one. When he came back, he turned around, he was like, no one's offered to get me a beer in a long time. And I really appreciate that. We started talking. I didn't know idea he was this megastar,
Starting point is 00:51:06 and he posted a picture, and then his uncle texted him and was like, dude, that guy knows more about crypto. Get to know him. And so he came on, he was on our podcast. No shit. Became friends with him. That's the power of the gift of gab,
Starting point is 00:51:18 I think, is what my father calls it. He did the same thing. But it's sort of like, it's like this weird blue collar grit or like hospitality, but with like big number swag. People are scared to be nice to people. I don't want to, I don't want her.
Starting point is 00:51:32 I think the guy sit in front. You know, ask him where you got is Jane. Like most people like to be out. And you end up doing some type of business with them. No, no, he came and got our podcast. He invited me in Nigeria. I made a huge mistake. He invited me to his wedding in Nigeria, which turned out to be like the coolest looking
Starting point is 00:51:47 thing of all times. But it was like a week before my daughter's wedding and I didn't think I could go and miss. But haven't you noticed the pattern of like this, all these silly small interactions have been like, I think you said with the Ethereum purchase, you like bought a golf stream or something crazy. And like it's just funny that serendipic. I guess serendipity might happen to everyone, but not everyone capitalizes off of it. And I've noticed a pattern where there's so many, like,
Starting point is 00:52:11 you're like, oh, I just happened to do this. And I've heard that like 12 times. You know what? I love other people's stories that you must as well advise you want to do the podcast. And so I get excited for other people. Like you meet David, you're like, that's freaking so cool.
Starting point is 00:52:27 And I wanted to know a story. And I didn't really think I grew up a rich kid. And even the relationship with the dad, It all fascinates me. And I think if you show interest in people and you're open with yourself, it opens up a lot of, you know, opportunity. And it's not a strategy. It's not like I think about doing this.
Starting point is 00:52:46 It comes from partly being raised with seven kids. It partly comes from, you know, feeling loved your whole life. Mom and dad love you. Your friends love you, you know, and so you feel comfortable in your own skin. The gift you can give your kids, the gift you can give your employees, is for people to feel comfortable in their own skin. When I went to Princeton, my great insight, you know, I had this roommate who was Gloria Vanderbilt's son. Unfortunately, he ended up committing suicide later on in life and it was so painful because he was such a nice kid.
Starting point is 00:53:14 Would that have been Anderson Cooper's brother? And Anderson's written about it. Yeah, well, I read Anderson's book on his mother. It's amazing. Yes. And, you know, I'm a young guy. I see, I'm meeting Gloria Vanderbilt. I'm like, oh, my God, I'm, you know.
Starting point is 00:53:26 Like with royalty? I'm a middle-class guy and my mom had grown up in Queens and so. Probably wore Gloria jeans. But she knew the whole story. And after about six months at Princeton, you know, Princeton's an unique place in that everyone lives in the same dorms, and they're kind of crappy dorms. There's not like a hierarchy of rich and non-rich.
Starting point is 00:53:51 And in terms of living space, and even quite frankly, social life. And you're like, they all shit on the same toilet as we do. You know, he's just, he's got his insecurities, he's got his strengths, just like. And the moment you realize, everyone's kind of the same. Everyone's a little bit insecure. Everyone's got an imposter syndrome. Everyone's trying to figure out who they are.
Starting point is 00:54:14 You had that realization in college? I had that realization in college freshman year. Man, so what I used to host these conferences called, my old company was a newsletter or company, whatever, it was like this media company, and we owned trade shows and or conferences, like a TED talk. And I would, I was 24 when I started doing it.
Starting point is 00:54:32 And we would get like the founder of like, WeWork or like Casper or Bonobos, like Brands or Zapier, which is now like a $10 billion company. These companies that were like at the time, obviously before we knew we worked was we were like these like $10 billion or whatever companies. And I would play a little trick on them where I was like, all right, your talk is at noon, but you got to be here for mic check at like 10. And like there's no mic check for conferences, right? Like it works.
Starting point is 00:54:57 The mic works. But I just wanted to be around them in the green room. And I would hear these billionaires completely. I would be, I would just be sit and listening with about four or five of them. And I knew, like, how big their companies were. And I would hear them complain about stuff about, like, I've had this CFO who I need a fire, but frankly, like, I just hate the confrontation. Or, like, you know, this one company had just raised $400 million and they were like, things are going horrible. I'm like, dude, I just read about you in the New York Times.
Starting point is 00:55:25 I thought you guys were the shit. And I remember thinking that that was, like, the most, like, enlightening lesson I'd had. probably in terms of business and how to live life, probably ever. And I was like, these people, they have the same downsides. They have the same issues I have, yet they're still like just moving forward and doing it. And I found it very freeing to know that the people I admire were broken. Listen, everybody is going through a similar journey. Like, there are very few people that are enlightened.
Starting point is 00:55:54 I've met a couple. I've met one or two. We're all on this path. And so I think the lesson I learned at Princeton wasn't that, I was the same as everybody, or is that I was no better or no worse than anybody. Sure. I did some things better than people and I did some things worse than people, right? Wrestling is a pretty objective.
Starting point is 00:56:15 This guy beat your ass. He's a better wrestler. And I've tried to keep that ethos my whole life. It's why at my parties, I got my friend, I got a real weird collection of people because I just like them. As opposed to a hierarchy of people. And I think that is what's brought me lots of joy. But it's also giving me, when I got to Goldman Sachs, I would walk into the boss's office.
Starting point is 00:56:39 It'd be like, dude, I got this great idea. I thought I deserved to be there. Now, often he'd say, that's a stupid idea. Oh, okay, good. And I'd go back to my seat. But the guys around me were like, dude, how'd you have the courage to walk into the office? I was like, he's on that same toilet as you do. Like, you know.
Starting point is 00:56:58 And so part of that sense. Were your parents confident? My dad was an all-American football player from West Point, but very quiet and stoic is the right word for him. Nice. He's become the kindest man in the world as he's gotten older, but he was tough but kind. But my mother was very aspirational,
Starting point is 00:57:18 the greatest storyteller, and she pushed us, not in a direct way, but like in an indirect way. Like, you know, we'd complain about some kid being able to do something and, well, she jumped up. Cliff, would you do it? Right? And there was almost this, like, we could be the Kennedys. I tease my mom all the time. She looked like Jackie O. She named my first daughter, my oldest sister, Jackal, and her first daughter. So we had Jackie, Robert, John, John, John. Do you really have a John, John, Michael? Like, I was like, Mom, you named us after the Kennedys. I did not. My mom and dad got married
Starting point is 00:57:56 right when Kennedy became elected, you know, I mean, it's. Kennedy, Kennedy is one of my eyes. I'm a huge history above. In the Kennedy family, I've probably read 12 books about them. Thank God you aren't the Kennedys, right? But it was very, my mother was very aspirational. She wanted the best for us, and she was a big cheerleader. She wasn't what you'd call, like, you know, the Jewish mom or the Korean mom that pressured, pressured, pressure. But, like, there was an internal sense of, of course you could do this.
Starting point is 00:58:22 And I think all of our, my brothers and sisters picked up on that. Are you nervous about raising rich kids? I think about that all the time. I thought about this when I became wealthy. I was like, there's nothing I can do about it. And so I had one rule to my children, be kind. And the only time I lost my temper, I had one son who was a whippersnapper a few times and was like tough on his brother.
Starting point is 00:58:43 Then I said, wow, where does that come from? Like I would really, only a few times in my whole life with my kids, I lost my temper. And it was always when I thought they weren't being kind. But I didn't think you could fake like not being rich. Like, I worked a ton for my, when I was a young kid, because I was kind of part of the labor force. And if I wasn't more on the grass, my mom or dad had to. If I wasn't doing the dishes, my mom or dad had, like,
Starting point is 00:59:08 we had a labor force besides my kids. And so you couldn't, like, fake, you've got to do this. It doesn't make any sense. And so I thought, and my wife, if I did a better job than me, all you can do is model good behavior. If you want your kids to work hard, work hard. If you want your kids to be kind to, the people that in your house and the cab driver, be kind of them.
Starting point is 00:59:30 If all you do is talk about money, your kids are only going to talk about money. If you talk about interesting things around the dinner table, your kids are going to talk about interesting. And so parenting really is modeling. And, you know, by no means have I been a perfect model. And my kids probably could give you 85 stories on how I haven't. But that was my philosophy. And they're going to be rich kids. And so far they've turned out lovely.
Starting point is 00:59:55 fingers crossed, you know, they've all finding their own path and doing cool things. And I think it's much harder to be a rich kid than a poor kid. Like, for us, our success was providing. It's going from here to there. We wanted to make money so we can go on a date so we can get laid, so then we can buy a house so we can send our kids to school. You want to be better than your parents, and your parents want you to be better than them. And with my situation, I'm like, man, I got really lucky at a young age, which means compounding is, like, Like, it's like, and I feel actually sorry for my children.
Starting point is 01:00:28 I'm like, the natural state is that you need to beat me, but I don't want you to feel the pressure that you need to do that. But they don't need to beat. The book Sapiens was all about humans are people of narrative, right? I love storytelling. The narrative in America was the American dream is your kids are going to have a better life than you. Yeah. So that got built into our system.
Starting point is 01:00:47 Yeah. At one point that's, you want your kids to have a good life. The European ethos is, I just want my kids to have a good life. And as you get wealthier, better better. I want my kids to feel self-actualized. I want them to have a wonderful life. Like, at one point, if you're Bill Gates' kid and he's worth $100 billion. Impossible. Like, I don't have 500, like, it becomes idiotic. And then you're like, you're talking about, dude. And so I think the moment you get even half as wealthy as you,
Starting point is 01:01:16 that narrative shifts. And it's like, how do I help my kids, how do I scaffold them to be self-actualized? whatever that means. I got one son, he's quirky and smart, and we have no idea what he's going to do. My wife and I, like, gamble on it. We're like, God, what do you think? It can go from here to there. He's hopefully going to find his niche and be successful,
Starting point is 01:01:36 and we will cheer him on. Appreciate you doing this. You're the man. I really admire your business stuff, but I don't think that's what you're great at. I think you're great at, like, living a full life. And I think that there's only a handful of people who I know from the outside or I know personally where I'm like,
Starting point is 01:01:51 I enjoy, if, like, life is like five different facets. I'm like, I really admire like up to four or even five of like the way they live life. Whereas there's a bunch of people who are like amazing at business. And you're like, yeah, he's amazing a business. But like, I don't admire anything else about him. And so that's kind of cool to like be able to hang out and meet with someone who I put on that list of people who I really look up to and how they live all different parts of their life. So thanks for doing this.
Starting point is 01:02:15 And this is awesome. I appreciate you. Thank you. I feel like I can rule the world. I know I could be what I want to. I'm out all in it like no days off. On the road, let's travel, never looking back.

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