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

26:32If 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 a thousand different ways to approach it. What does Steve do? You were saying. I know Steve pretty well, but I don't know his exact process. But I would tell you he's one of the most competitive guys out there. He used to go on vacation and have all his screens set up. And if he didn't, and he wasn't feeling things right, he'd fly right back to get it to his desks. like he was obsessed with beating the markets.

27:05You think you're competitive? I'm not as competitive, which is interesting. When I think about like with Stan Druckenmuller and Louis 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, Louis Bacon, I remember playing croquet against them, and I'm like, how's this guy 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 disciplined. And those two cross factors.

27:39Creates a maniac. Well, creates an amazing performer. Yeah. Maybe not the easiest person to go to cocktails with. Sometimes they are, you know, but like an amazing performer. And I don't want to discount, I've had an amazing run of success at trading. I just know myself as I compare myself to the other guys a little more disciplined 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 Hoobrock, I was miserable because I was feeling so much pressure.

28:32And 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 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, you don't get it from sitting in a box. There's a tremendous amount of information 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.

29:11There'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. A lot of it's historical, too. Like, you see things, they repeat themselves. Yeah, I heard one of my heroes is John Rockefeller, and I was listening to Business Untitled, and you were like, when I was in fifth grade or eighth grade or something, I wrote a paper on Jadon D. Yeah. And I thought that was cool, because he's a fun-ass dude to learn about. And you also, you and your partner Wes did the train thing. Wes did the train thing.

29:37I 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. Yeah. I went and talked to a bunch of friends of ours who, we have mutual, you and I have some mutual friends and uh i want to tell you what they said they go 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 um uh he's blown up a couple times and he's won a lot more i'm amazed at how good he is at managing risk and i actually talked 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 uh you got lucky that bitcoin exists when it does i think that you're a guy who um you enjoy risk you enjoy i think you you were telling i heard a story about how you said like you are a 37 out of 40 in terms of like uh some type of personality test of freaking rules and you're like it's funny my kid like is the exact opposite and then you hear i read the new yorker or some article where they're like he flew a helicopter down the street like during the prince's graduation like there's a 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 so part of it is there's this balance between like yeah there's a there's an adrenaline need like i i like adrenaline like in sports and in trading and then 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 have 1500 per month paycheck uh pat tyranny who's a buddy of mine still was one of my buddies down there and we had the time of our lives i when i look at how much fun and how much i enjoyed that in the middle of freaking lower ugly 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's 700 guys and a few women at flight school 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?

32:10I 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. I would be embarrassed. I'd be frustrated. Because all the money really does at one point is 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. 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.

32:50I do spend lots of money. But I threw 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. 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.

33:28And he talks in his book about how he was like, I research like crazy. Like anytime I get into a business, I research like crazy. So I read all the books. I use Tejas or whatever else, like the services and alpha sites or whatever they are. And like I hire experts. 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, 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.

34:01It was. like so that's like pretty magical like to be around and hear stories of that family and then like your other roommate helped create ethereum uh 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 it's like you i'm a good guy to sit around a campfire with drinking because i got a lot of stories but there's just so many times where it's like oh i just 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 they just happen to be like these like wild crazy people who what was the story about how you first heard about Bitcoin.

34:33So Pete Brigger, who had been my... He lived above me my freshman year at Princeton. He lived in the room above me. This dorm was amazing. We had a pretty cool little group of people. Right? Is this wild? It's like the greatest dorm on earth. He lived above me. How many billionaires are from that dorm, do you think? 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 Bleecker Street, a little drunk, 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.

35:14And then we lived in Hong Kong together, and we slowly became very good friends. I'm the godfather of his youngest son. Then we did Fortress, and he was the guy, I said, was the distressed debt investor. Well, because he made a promise to his wife that at one point they'd move back to California. He moved his entire business or the bulk of it to Stanford area, Palo Alto. 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, but he's not a tech guy. But his brother-in-law was a tech guy and the group of friends he had were tech guys.

35:49And they all started talking about Bitcoin. And Pete wanted to be part of the, you know, the clan. And so he called me up. He said, I'm hearing about this thing. 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. And this was in 10? This was in 2012, 2013, maybe. Bitcoin was at like$96. So it was nothing, really. I mean, there's not, there would have been like Bitcoin.org or like some forums. There wasn't a lot, but it was online. The Chinese had just started buying it. And I made a thesis. I said, oh, we got to buy it.

36:24And 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. 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 invested, who had, you know, had a similar... Went to Princeton, he'd 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.

36:55He was trying to figure out what to do. He'd done 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 fortunes had gone public than Dan at the time. And we're like, if he's putting that much in, we need to put at least that much in. And, you know, that's the way guys think. And so we all roughly put similar amounts in. Was it like eight figures? Or you can even say that? It was seven figures.

37:28Seven 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 it's worth$100 ,000, your friend's like dude you gotta take some yeah you can buy a house you can 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 having made lots of money in crypto it was easier having started rich and it's gotten me thinking why this world is so off sides when you're wealthy you have assets Assets are basically chips on a table.

38:20You know, I bought SpaceX when it was, when 20th was today, because everyone was like, ah, you got to buy some SpaceX. And you looked, you're like, Elon Musk is killing it. 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. It's why Piketty 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.

38:59And 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. and through that network, you learn stuff. So for our podcast, my listeners will make fun of me. 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 S &P 500 and bonds. You invest like you're a white guy from Missouri. Oh, yeah. Look, it's worked out. White bread, boring. Which means I've outperformed about 90 % of hedge funds.

39:39So it's worked out. But like... Listen, it's been a great... Yeah, I've like, I started making money in the greatest bull market of all time. And do you, for your personal finances, do you have any boring stuff? Or are you active for the whole thing? No, I... Listen, I have a chunk of money in, you know, these credit funds, like the one Pete ran, 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 you get rich real quick and so i have someone private credit i have a lot in my own company uh 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 they're the group that owns it is putting it up for sale so hoping hoping that sells for a high price but i i haven't really ever done bond stocks partly because that's what i do yeah and my money has often been tied up in the enterprise that i'm engaged in at fortress i owned a lot of fortress stock i guess you've been illiquid like for a large portion of i i probably have run the the 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 i i've always had a lot of I think that I'd make money.

41:06And so I've always either wanted to live a big life and also make a lot of investments, and so... So you spent, you just spend a lot? Spend a lot. I live large, I invest large, and I always think I'm gonna win. And so in 2021, we thought we were gonna be able to take Galaxy public, and I was gonna get a lot of liquidity. And it turned out we took a little too long to get into the SEC queue. The administration changed, Gary Gensler shut the door. And so for four years, no liquidity out of Galaxy. You know, my other stuff, I made some good investments, some bad investments and didn't really change lifestyle and you slowly start burning the furniture of liquidity right and so we just did a we just did a deal we took some chips off the table in terms of liquidity did you you live life on the edge i mean i think that i i admire like your ability like i'm an adrenaline seeking too 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 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 goldman sachs and so that that was painful coming back from that gives you a lot of confidence that yeah you can fall down and like you can lose money it's not the end of the world you're gonna you gotta learn how to get back up and being a wrestler teaches you that.

42:31Like, no wrestler wins every match. Cale Sanderson did it in college, but then he lost in 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 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, it 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, he lost 48 % of the points he played. He was the greatest tennis player of all time or one of the top three.

43:05That 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? 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 figuring out who they are. Like, like literally trying to understand like who they are and why they're who they are. It's always your parents. You've got a relationship with your mom and your dad. Whatever the story was, dad disappeared, processing that, right?

43:46That'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. I'm 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.

44:21Most people don't invest in themselves. 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 ran 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 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.

45:01You sit there for frickin' 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. Hey, this episode is brought to you by Mercury. They are the fintech of choice for over 200 ,000 companies. I myself use it for eight different companies. The reason why we all choose it is because it has everything you need under one roof. So like my e-commerce company, it's super important for us to be able to easily wire transfer, pay all our different vendors and suppliers all around the world.

45:39And the old way with our more traditional bank that shall now be named, I try it online. It would say no. It would freeze my account. Then I'd have to go in, book an appointment, speak to a specialist who would try to upsell me on something I didn't need. and then finally after you know 30 minutes there then they charge me 50 bucks for the pleasure of that terrible interaction and now with mercury i just go online push two buttons and i'm done it's such a seamless experience it's very intuitive everything's under one place they basically took all the things any company would need for their financial tech and they made it super easy to use to put it under into one platform so highly highly recommend it if you're not using mercury i question your judgment so that's it you've heard it on my first million for more information check out mercury.com.

46:17Mercury is a financial technology company, not a bank. Check show notes for details. Do you set goals like this? Like, 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 week meditation and then this party here. Are you setting, um, 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.

46:52And 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 in 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, 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.

47:32But my brain, you know, like how do I have fun? think, 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, a 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. 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.

48:13My wife wakes up every day, 6.30, and meditates an hour, and meditates an hour at night, and doesn't miss. I'm just like, she's like a metronome. And I'm like, I know that would be good for me. And I do meditate once in a while. When I'm stressed, I can 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 the first time ever. And the thing was like, I got to love myself and forgive myself. And you're like, that was like a huge breakthrough. And I'm like, in my head, I'm like playing armchair expert here.

48:46But I'm like, you're doing it again. You know what I mean? I'm like, dude. 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 time you see those people is when they literally hit some horrific rock bottom that the only way to live is to change. Right. That's the whole AA cycle where they just give up and say, OK, 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.

49:28Right. Yeah, I mean, I love hearing about this shit because I think that, um, I think that, you know, this is gonna sound pompous of me, but in my head, I'm like, I can be like, you know, he's, you know, I'm 35, so I'm like, okay, he's 25 years ahead of me, and like, I had - And we both can't hear. Yeah, we're both a little bit deaf, and I came from a blue-collar, like, uh, family, and I - I think you talked about Princeton, about, uh, like, you're 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 I've felt that, like, I hadn't been in New York City until I was 26 years old, hadn't been on an airplane until I was 21.

50:04And so 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 and I'm like, and I'm looking at apartments 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 turn on the TV, I see Timothee Chalamet, I see the Jenner girl, and then I see Mike. And I was like, oh, motherfucker, we were supposed to do a thing.

50:40And then I was like, my wife was like, can you blame him? I'm like, no, I can't. Nick's in the playoffs is his mud. This city erupts. Dude, you had, like, there was Timothee and then you. We got good seats. You were like the man. How much does a playoff seat cost? Where he's, I imagine his referee. Seats are free. And if you want to buy front row in the playoffs, you know, they can cost as much as$50 ,000,$80 ,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? Well, no, ours, we have season tickets. Okay, got it. And so you just pay the normal, whatever Knicks charge you for playoff tickets.

51:16That's crazy, man. And so. Do you see, you know who Ryan Cohen is? Yeah. Billionaire Ryan Cohen. I don't, 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 Jalen Brunson fell in his lap and he didn't break eye contact from the beautiful woman he was with. 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, and DeVito, the Nigerian superstar, there are two guys in Afrobeats, right? DeVito's one of them. The other guy's Burna Boy.

51:52Was there and I didn't know who he was, but he had a great Shane. I like Shane's. And I'm like, dude, where'd you get that Shane? And I went to get a beer. And I was like, you want a beer, a Coke or something? And he did it one way. He came back, he turned around and he's like, you know, no one's offered to get me a beer in a long time. And I really appreciate that. And we started talking. I had no idea he was this mega star. And he posted a picture and then his uncle texted him and was like, dude, dude, that guy knows more about crypto. Get to know him. And so he came on, he was on our podcast.

52:20No shit. Became friends with him. That's the power of the gift of gab. 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, people are scared to be nice to people. I don't want to, I don't want to, I think I sit in front of you, you know, ask him where he had his Jane. Like most people like to be at. And you ended up doing some type of business with him. No, he came and got our podcast. He invited me to Nigeria. I, I made a huge mistake. He invited me to his wedding in Nigeria, which turned out to be like the coolest looking thing of all times.

52:53but it was like a week before my daughter's wedding and i didn't think i could go and wait 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 like it's just funny that serendipity i guess serendipity might happen to everyone but not everyone capitalizes off of it and i've noticed a pattern where like there's so many like you're like oh i just happened to do this and it like i've heard that like 12 times you know what I love other people's stories that you must as well, otherwise you wouldn't do the podcast.

53:27And so I get excited for other people. Like you meet Davido, you're like, that's freaking so cool. And I wanted to know his story. And, you know, I didn't realize he grew up with 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. 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.

54:03The 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 Venerable's son. Unfortunately, he ended up committing suicide later on in life and it was so painful. because he was such a nice kid. Would that have been Anderson Cooper's brother? His 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 how I'm meeting Gloria Vanderbilt. I'm like, oh, my God, I'm, you know...

54:31Like with royalty. I'm with royalty, and 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 a 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 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 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, and everyone's trying to figure out who they are.

55:20You 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, it was a newsletter company, whatever, it was like this media company, and we owned trade shows, or conferences, like a TED talk. And I would, I was 24 when I started doing it, and we would get like the founder of like WeWork or like Casper or Bonobos, like brands that, or Zapier, which is now like a$10 billion company. These companies that were like, at the time, obviously before we knew WeWork, we were like these$10 billion whatever companies.

55:53And 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, the mic works. But I just wanted to be around them in the green room. And I would hear these billionaires complain. It would be, I would just be sitting 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 to 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.

56:28I'm like, dude, I just read about you in the New York Times. 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're, they have the same downside. 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. Everybody is, is going through a similar journey. Like there's very few people that are enlightened. I've met a couple. I've met one or two.

57:02Um, 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 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 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 and be like, dude, I got this great idea.

57:46I 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 shit's on that same toilet as you do. Like, you know. 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, the greatest storyteller, and she pushed us.

58:26Not 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 off a 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, Jacqueline, her first daughter. So we had Jackie, Robert, John John. Do you really have a John John? John, yeah, John. Oh, my God. like I was like mom you named us after the Kennedys I did not my mom and dad got married right when Kennedy became elected you know I mean it's Kennedy Kennedy's one of my I'm a huge history buff in the Kennedy family I've probably read 12 books about him thank god you aren't the Kennedys right like 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, pressured.

59:24But like there was an internal sense of, of course you can do this. 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, one son who was a whippersnapper a few times and was like tough on his brother. Then I'd say, 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.

59:55And 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 one of the grass, my mom or dad had to, if I wasn't doing the dishes, my mom or dad had like, we had a labor force besides my kids. And so you couldn't like fake, you've got to do, This doesn't make any sense. And so I thought, and my wife probably 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 are in your house and the cab driver, be kind to them.

1:00:35If 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 things. 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, so far they've turned out lovely. 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.

1:01:10Like for us, our success was providing. it's going from here to there. We wanted to make money so we could go on a date, so we could get laid, so then we could buy a house, so we could send our kids to school. You want to be better than your parents, and your parents want you to be better than them. Yeah. And with my situation, I'm like, man, I got really lucky at a young age, which means compounding is like, it's like, and I feel actually sorry for my children. 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 you.

1:01:39The 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. Yeah. At one point, 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, 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, wait, I don't have$500 billion. Like, it becomes idiotic.

1:02:14And then you're like, you're talking about it, dude. And so I think the moment you get even half as wealthy as you, 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, and we will cheer him on. Appreciate you doing this. You're the man I really admire. I admire your business stuff, but I don't think that's what you're great at.

1:02:48I think you're great at 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, I enjoy. If life is like five different facets, I'm like, I really admire up to four or even five of the way they live life. Whereas there's a bunch of people who are like amazing at business and like, yeah, he's amazing at 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.

1:03:20So thanks for doing this. And this is awesome. I appreciate you. Thank you.

1:03:38All right, this episode is brought to you by Mercury. They are the finance platform of choice for over 200 ,000 companies. Shouldn't be surprised because I use it myself for not one, not two, but I have eight different Mercury accounts. I have seven for different companies that I'm a part of, and then I have my own personal account because now they have personal banking, which is a really cool feature. I highly, highly recommend it. Like I said, I use it myself. And the reason why is because the way that Mercury works is beautiful. It's very intuitive. And you could tell that it's actually made by a startup founder.

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