Full Transcript for $100M hedge fund manager: Do not make the mistake of dying rich

I kind of wanted to be like Jesus and just like go forth and build a church. I'm not here. Like, I don't want to be the guy, you know, a lot of people write books to be the guy. I don't want to be the guy. I want to live my life. I want to be Jesus, but I don't want to be the guy. 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 day. Bill, on that note, welcome to the show. Thanks. I don't know if you know what you're getting into. So basically, we're a bit of a catfish show. So the show is called My First Million. And it's a very obnoxious name that I picked six years ago. But the show got popular, so we didn't change it since then. And so people come because they think it's all about making money and getting rich.

And it kind of was at the beginning. And then as we got rich, we started to turn our attention as one does to the, to living a rich life versus getting rich, which is the subject of your book. That is how I discovered you. And so we're going to talk, I want to talk a little bit about both the making of, as well as the using of money. And so maybe we start with, can you just explain how'd you make your money? I made my money, the original pool of capital, I made my money trading commodities.

I trade natural gas derivatives. Started out as like assistant peon as a clerk on the New York Mercantile Exchange floor. When the natural gas futures contract started, I really wanted to get into that. I became an over-the-counter broker, made like moderate money as a broker, but really hated brokering. And then when deregulation hit in 1995,

They were recruiting a lot of people from New York to come run the derivatives desk in Houston, Texas. I moved to Houston, Texas, and that's when I started as a trader making real money. Sam, when he says energy, he's an energy trader, commodities, derivatives, what does that mean to you, Sam? How much of that do you understand? Yeah, not much, frankly.

We create websites that people come and they either buy something or we make money via ads. So when I hear that, I'm like, are you buying barrels of oil and selling it to someone else who needs it? I'm kind of an idiot when it comes to that. Yeah, you're basically just betting on price go up, price go down, or vol go up, vol go down with spreads, et cetera.

How did you get good at knowing if the price would go up or go down when every other smart guy is also trying to figure out if the price is going to go up or down? How do you win that game? Well, you know, we're really not in competition with the other smart guys. We're kind of glorified insurance agents. Like, we don't want to trade. We get induced to trade based on what the market is doing versus what we perceive for fair value.

And so that's kind of like what an insurance agent does, right? Like, it's like, okay, this is the... distribution of outcomes. Here's fair value. Here's my, you know, theoretical edge, right? I'm going to charge you X for this insurance product. Can you give, can you give like an even more dumbed down example? So like, for example, a company needs to acquire a bunch of oil.

Are you the middleman who would go and acquire it and you would try to get a small profit? Yeah, let's say the The winter's coming and people are afraid prices are going to go up. And generally, I was always short, right? Because people are always afraid prices are going to go up in the winter for natural gas. And we'd be like, okay, we'll sell you futures contracts.

They've locked in a hedge from it going up and I'm exposed to it going up. But, you know, by and large, prices generally went down. The winter risk premium usually bled out and the prices would go down. And most of the money I made was from being short natural gas over time. Being a trader like this, it's one of the few gigs when you can get pretty rich as an employee working for someone else.

I think I read that you made close to a billion dollars in profit for the company that you were working for. Were you personally making any money? Yeah. I mean, had I been smart or smarter about it, I would have made a lot more money by having a lot of my money invested in the fund. But we had this theory back in the day, which was actually wrong because I was younger when I look back.

That it's okay to have no money and a job, and it's okay to have no job and money, but it's not okay to have no job and no money. And so we were like, okay, if I get blown up here trading, it didn't mean I don't want to have all my money parked in the fund as well. Now, what I didn't take into account is that I was very young and maximizing risk at that age is probably the way to go.

And I should have been fully concentrated and just bet the farm because I was always going to be able to get another job. So, yes, as a trader, most traders at independent hedge funds, not necessarily the banks, et cetera, you eat what you kill. So you don't really get anything if you don't make money and then you get a percentage of the money that you earn when you do well.

And you were saying, you said, well, I initially made this

pool of capital by trading. Were you sort of broke and then you just had like a killer year or a killer deal and it just, you had a windfall or were you making it as you went? I was kind of climbing the earnings tree first as a broker. I was an OTC broker, which I hated. I was good at, right? But you're going to make six figures, you know.

You can make more if you like start a firm and be part of a firm. But the analogy I would use is somebody who buys and sells houses versus somebody who's a real estate agent. I hated being a real estate agent. I wanted to be a guy who bought and sold houses, right? And so I wanted to be the trader. And so I was

well off as a broker and got rich as a trader. Now, we've had a couple of different types of investors on the podcast in the past. We've had like Howard Marks, Ray Dalio types. And I would say a lot of what they talk about, there's kind of three ways to win that I've picked up. So one is superior temperament. So, you know, the kind of Buffett model of, you know, be greedy when others are fearful, be fearful when others are greedy, people who can handle swings better than others.

And that led to superior returns. The second one was like an informational edge. They understood something about a technology or a market and where the puck was going. And they understood the implications of it better than others did. And then the third is just straight up arbitrage. You know, I'm buying an ETF and I realized that the underlying hundred stocks underneath it are not priced exactly, you know, in sum to the ETF price.

And I could just kind of with no risk, make a spread here and I'll do it until that arb disappears. Were you one of those three or were you a fourth way of making money? I would say we were one and two. We weren't the arbitrage. We were one and two. So the idea is that the market is comprised of a lot of people who are some people punting around and just straight gambling, people that need to hedge, and then people who really, really understand the market very well, study every single aspect that drives supply and demand, right? And then what may happen.

And then... will have a position based on that, irrespective of your superior knowledge. If you are not stoic about losses and can handle that, your prefrontal cortex will not work while your amygdala is going crazy, right? Or you're thinking about, wow, I lost a bunch of money, or you're that type of person that needs five wins for every loss because that doesn't exist in trading.

And so... No matter how bright you are, you need to have that temperament, that stoic temperament, that ability to handle losses or

be robotic about trading. But your temperament is a little bit different, and I kind of find it more interesting. So like we've had, like you said, Howard Marks, let's say. Howard is sort of an academic. He's like part philosopher, part academic, same with Ray Dalio. Like they're sort of this very unique type of thinker. Your attitude, from just reading about you, you appear far more Texas cowboy.

Like when I read books about like H.L. Hunt, you know, one of the guys who like got oil going in Texas in the mid, you know, 1900s. It seems like you have that energy because it seems like you are way more risk on than some of these other guys that we've mentioned. Is that accurate? To certain, it depends on the product you're pushing, right? Like our product is like a high vol product.

And so like, I always say that like, hey, this is a fund to get rich, not stay rich. And get rich is concentration risk. And so like it comes off as like yeehaw, but it's really a thought out thing, right? Like you can invest in my fund and you can lose 100%, but my fund can also return 300, right? So like it's really the expected outcome and what are you trying to do here? Did you ever almost lose it all? Yes, a couple of times.

Hey, this is one of those episodes. So I don't want to show you my notes, but just imagine this is full of notes because the other pages are. Sean and I have been sitting here taking notes for this episode. And whenever that happens, what we decide to do is make life easier for you and put all of our notes into a document that you can just click here in the link below and download.

It just makes your life a lot easier. So no need to take notes. Just download what we did. And we made it pretty actionable, very easy to understand. So click the link below and get it. Now enjoy the rest of the episode with Bill.

What were the swings in numbers? Down 50% to plus 250. On how much money are we talking about? 100 and something million, 200 million, you know? So 100 million to 250 million. Yeah, by, you know, a year, and then we go through the winter, we build it up, we chop wood, and we go there. And that's why I like to, you know, we say, I said the name of the game is to stay in the game.

You know, we're in a market that provides edge to people that really study it and keep their wits about them. And so... if you are able to not completely blow up and get knocked out of the game, you will eventually have outsized returns. It's the same thing with insurance, right? Like you're saying like, oh, they're cowboys. These insurance guys wrote these insurance policies against hurricanes and then two hurricanes came and they have a terrible year.

Like some almost get wiped out, right? But then they keep writing insurance the next year. The insurance goes up and they just print money and print money. And so unless you're in the arbitrage game, you will have a bad, you will have a very bad year. Sean, this seems like your style a little bit.

I do enjoy myself a little gamble. Now, let me ask you a question. You seem today like you're a pretty chill guy and you have all these hobbies and interests and friends and the kind of well-rounded life. But everything I know about traders is that they, you know, I asked one guy, well, you know, were you kind of a maniac back in the day? He's like, Dude, we were pissing in Coke bottles on the floor.

It was intense. The intensity of trading is crazy. You wake up at certain times to check what's going on in Tokyo and blah, blah, blah. Did you have a decade of your life where you had to be a bit of a maniac or no? Yeah, you become obsessed with the puzzle. And that obsession helps you to have informational knowledge edge or to think about things that could happen that other people are not thinking about.

and scoop up the money. And so I think that happens to all traders, to whatever they're trading, right? Like, because it is a very, very difficult thing to do. It's complex. There's many variables moving around and you have capital at risk. So you're always, whenever you have a position, you're always working. You're never off, right? Knowing what you know now, would you have advised your younger self to go into that field? Or would you have said, hey, just build a company that's going to sell a product? Yeah.

I would have went into equities. It's just much bigger. And it's, you know, guys have $6 billion funds, $10 billion funds, right? With like what I would consider okay track records, you know what I mean? Or not that exciting track records. And you get positive drift on your side from the stock market. Does the skill set translate? So equities, meaning you would evaluate different companies and figure out which ones are great and buy.

Yeah, have a basket of stocks. There's just so much more capital available for people to invest in equities. It's kind of like, you know, there was a period where there's nowhere else to go type of mentality. Like, we have to be allocated equities. And so... And, you know, the fees they charge in equities are quite amazing on these giant funds, right? Like, you have a $6 billion fund charging one, one and a half.

I'm like, what fund costs that much money to run? You know what I mean? Like, it doesn't, right? So, like, you're...

your maintenance becomes a profit center and then your upside is just amazing, just in terms of the notional dollar amounts. In terms of personal wealth, how could I have been much richer, would have went into equities. Do you do that now with your personal money? Yeah, I do. But I'm 57. I'm not here trying to have a party at 85. You know what I'm saying? Like my life is now, you know, like if I were younger, that makes sense.

But like for me, I'm at the back quarter of my life. And so it doesn't make sense for me to be wasting my current years to earn a bunch of capital for future years, given my age. Yeah. When you were coming up, did you have like a number in mind, a goal? And then did you hit that number? Did you just simply like most people move the goalposts and say, no, no, no, that's not enough.

Like describe to me kind of your, what your relationship was with the number. Yeah, the number was, I just wanted to be a millionaire before I was 30. It was kind of a thing, you know, I blew through it, but there was never like a cap number. Like if I make X, I'm going to quit. I didn't really think it through at that time. about what it was.

Like I was young, I wanted girls and a rockstar life and all the bullshit that comes along with it. So I didn't have like a really thoughtful process about like, what do I want out of life and what does that cost? I just knew that I wanted a lifestyle. I wanted to be rich. I wanted to be able to get the girls. That type of thing. And then everybody kind of parrots.

Like, I want to be a millionaire before X date. It's almost like a Miss America cookie cutter answer type thing that people starting out do. They're not really thinking about it. It wasn't until later in life that I really... I was thinking about like, what does that mean? And what does the number mean? And is it even a number, right? Is it really a date? When you're talking about later in life, is that like in the last five years or that was when you were 32? It was probably in 30s started really starting cementing the ideas of like, the number doesn't matter.

The age date matters. Like your net worth peak is actually a date, not a number. Just given the fact that your body is a decaying asset and its ability to convert that money into fulfillment and useful experiences declines. And that rate of decline starts approaching affinity as you get close to your deathbed.

More money means nothing at a certain point in your life. And so that slope matters more. And so that isn't when you're 20. That isn't when you're 30. So somewhere between 30 and 65, that slope starts to really pick up such that more money doesn't really mean anything to you. What was that moment that changed that where you realized there's a different way to live? Like, did you read something? Did you experience something where you're like, where you got smacked in the face and you're like, there's a better way.

And this is where I'm going to carve out this new path. Yeah, it wasn't like I was on my horse on the road to Damascus and then I fell off it and got a vision. It was more like there are many things. I read a book called Your Money or Your Life, which kind of introduced the concept that the best definition of money is something you exchange hours of your life for.

And then that kind of like set off a whole bunch of other thought processes about like, okay, I'm exchanging hours of my life for capital. What's that capital for? Like, what are my values? And then started thinking about that. Like, okay, I'm giving up hours of my life to get hours of other people's life to do X. What are those things, right? And why? You know, that started coming along.

And then, you know, really thinking about death, And when do certain things happen? Like, you want to get the girls, but it's not when you're 40. You should probably be married by then. You know what I mean? Like, you want to do all the rock star stuff, but it's not, you know what I mean? It's not at 55, right? And so, like, it's kind of like what experiences belong when and what does the arc of my life look like? How does money fit into that? How does health affect that? And so, those thoughts...

were reinforced by different conversations, books I've read, et cetera, to come up with that comprehensive way I thought about wealth, health, and time, and how to allocate those resources throughout my life to get the maximum amount of fulfillment. And, you know, I had to answer what is the purpose of life and the purpose of life is to be fulfilled according to your own values.

And so then I was like, okay, what does that mean to me? And then how did these variables fit, you know? And so that was over a time period. It wasn't just like, oh shit, here it is. I have this formula, you know? E equals MC squared or, you know. It kind of is like that. It's sort of funny. Like the reason Sharda and I aren't particularly investors, but we'd like having these investors on because it's sort of funny to see them take their Rain Man like abilities to like analyze numbers.

But they use it towards other parts of life. And that's where it starts getting interesting because they're sort of very rational, whereas most people do things just because that's how everyone else does it. And you start hearing these fairly rational, somewhat controversial opinions on how to live life or handle risk or whatever. And that's where things start to actually get really interesting because...

they kind of break the mold. And that's what you're describing. And so it's pretty funny to hear you talk about like the balance sheet of life, just like a decaying asset. That's kind of interesting to me. It's funny because, you know, one of the things that had an impact on me that was like, I was in an argument with a friend on a football team named Dwight Sistrunk at the University of Iowa.

And we were talking about something, I don't know. And he was like, Yeah, I don't want that. That's what you want. Like, I don't want to pick a fence in a White House or whatever and go get a job and work like that. I don't want that cookie. I want a different life. And I remember thinking, like, well, what could he possibly want? Like, I was so inculcated with, like, the bullshit and the Chevy Chase movies and get married, have kids, get a nice car, climb the corporate ladder that I couldn't even see past that, right? Like, um...

And that conversation haunted me later on over years combined with other things to like think about, okay, different people have different values. Fulfillment means different things. What's a values agnostic way to look at these variables in order to have the most fulfilling life? I want to read you an email I sent to my sister and my mom.

That's from your book. It's an excerpt from your book that resonated so much that I hand typed it back out by hand. I like that. I was like, y'all aren't going to read this book, but I need you to read this. And so it says, death wakes people up. And the closer it gets, the more awake we become. And when the end is near, we suddenly start thinking, what the hell am I doing? Why did I wait this long? And then you go on and you say, Most people live their life like this.

They build a well and start to pump water. As the well fills, they use a cup to scoop out a tiny amount of water. They take a sip, and then they go back to pumping. Higher and higher goes the water. And at the end of their lives, after a lifetime of pumping, they are still thirsty. They spent their whole life pumping rather than drinking.

You talk about a couple of the principles. One, timing matters. Some experiences can only be enjoyed at certain times. You can't water ski when you're 90. Number two, what to worry about. You can always make more money in the future, but you cannot make more time in the future. So it makes sense to not worry about squandering our money. Squandering our lives should be a much greater worry.

That's like the why you write this book. Why do you think about this? Is that I was very, very afraid of wasting my life. Very, very afraid. A lot of people, they're like, they get so caught up in the game of making money, whatever. And they're like, oh, I fear losing money. I fear losing all I built. And I fear losing my status, whatever.

And I'm just like, that shit. I fear wasting my life. The money is just a tool. How do you balance career ambition, ego,

and living where you're going to die soon and all that? I mean, that's really hard. Yeah, I think if you really want to be successful and do something different and live a non-standard life, you really have to crush your f***ing ego constantly. There are some high ego people that somehow make it or whatever in a narrow lane, but then I tend to think they suffer the other balancing points and having a real fulfilling life.

Can you explain what you mean by crush your ego? What does that mean for you? When did you do that? Well, most people who don't start a business or don't go chase an opportunity, et cetera, don't do it because of ego. not because of the money risk. They can handle the money risk. They can handle losing that job and becoming a waiter or whatever, but their ego cannot take the status drop.

They cannot take, oh, wow, I'm now less than my friends on this poll of measuring money making. I'm going to look like a fool doing this to other people. And so... Yeah, they'll argue with you and give you motivated reasoning that this is why they didn't do it because it was hard or it was, you know, this was difficult, whatever. And I always tell them, like, I don't give a fuck what the adjectives are.

I don't care if it's salty. Is it a shot at the life you wanted to live? And why, you know, why didn't you take the risk? And when you really break it down, when you really talk to somebody, you know, it's ego. They're just chicken shit.

And, you know, like, it's hard. Like, if I don't know a person, like, I'm not going to be, like, calling them chicken shit to their faces. But my friends who get the straight dope, I'm like, you're just a f***ing pussy. You're just a straight pussy. And they know it. They know they are. They don't... They cannot take the ego risk. They can't take the judgment of their own selves, their parents, their friends, wider society, that they went out, tried this thing, and failed.

And it's the reason why people... root for you to, you know, quietly root for you to fail when you try something because you expose their own cowardice. Let's say you point out to a friend. You say, look, man, I think you're just being scared. I think you're just being a pussy about this whole thing. Is there more to it than just That's what it is.

Get over it. Hey, you need to just do it anyways. They still don't do it. I mean, a lot of them still don't do it. For the few that do, what works? What works to get them out of that state? I mean, awareness is half the battle, but there's a whole other half that has to be done, right? Like, it still has to turn into action, right? There's a lot of alcoholics that are aware they're alcoholics and they still drink, right? Like, the action plan still has to happen, right? But let's assume that you are a person who is not being soft and living the life that you like.

What percentage of the year are you actually not being soft? What does living to this standard actually look like? Because it's easy to say that, But I'm sure you, like, you're a human. You get soft like everyone else. Yeah. So, like, how many times a month are you doing something where you're like, shit, I gave in. I shouldn't be doing this.

I followed my ego. Or I said I will. I committed to something that I shouldn't have committed to. Whatever. I mean, it's a constant conversation I have to have with myself about a lot of things. It could be an interpersonal relationship on having an ego and not saying I'm sorry. Like, I don't want to look wrong. You know, I don't want, I don't want to appear wrong.

I don't want to appear like I'm the person. It could be like, I don't want to look like an idiot. I don't want to go get up and do this. Or I, I, I, I'm being soft about this situation. I, you know, I've had a lot of training and not giving a what other people think. both in compliments and derision. And so it allows me the freedom to be me and try things that other people would be scared to do.

How often do you get accused of being an asshole? Like, how do you live this life

But like, you know, being kind and loving to the people you care about. It's very important to be kind. I'm a big supporter of people. Like I want people to win, give them my time and show up for them. But my time is extremely valuable. I don't know. Probably my wife was like, you're being an asshole. It's probably like a month ago or whatever.

It's usually when it's just like an argument and being forceful about being right. And you just don't need to be right. You need to be loved and like, you know, let it go type of thing. That's a good line. And so I think it comes across. And I'm also very, I'm like, you know, on the complete empath, an empath to a autist. You know, I'm kind of over here, like one shade in the autism.

Like I give people the straight dope and, you know, I don't pull punches. I don't feel people get any value from me if I'm performing some sort of social niceties. I think you should get like the straight dope from me. So I think if you are not, aware and value that type of feedback, you might be like, oh, he's an asshole, as opposed to, wow, you actually told me something that my closest friends won't tell me and are giving me the straight dope.

Whether it's accurate or not, that's up to you. You can take it or leave it, but I'm providing you a proper mirror. Like, I'm the type of guy who will tell you, like, you got a booger hanging out of your nose and some people won't. You know what I mean? And so, like, but you got friends that are just like, I'm not going to say anything while you're sitting there talking with a booger out of your nose.

Like, so, like, it's just, you know, that's how I show up. I don't want to embarrass you, so I'll let you embarrass yourself. Yeah, exactly. Like, exactly that type of thing. And for whatever reason, you know, it doesn't mean they're being an asshole or whatever. It's just that's their programming, you know? Hey, so a minute ago you were talking about, like, You had a friend who was saying, look, I don't want that kind of cookie cutter life.

And you realized that you had been wanting this kind of cookie cutter life, this vision that had been set for you, whether it's from the movies or your parents or whoever, right? I think every man goes through this. Cultural osmosis, as I like to call it. Yeah, exactly. And it sounded like you had to go redefine with a blank sheet of paper What do I care about? What kind of life do I want? And you had to put some definition behind it.

Something that meant something to you. And even if others wouldn't want that, you really wanted it. What did you come up with? What is the answer to that for you? I really, you know, it wasn't like I sat down and like I cracked through and sat down with the Dalai Lama and meditated. But I realized like, hey, What I wanted at the time, I was going to go for it.

And then I realized that a lot of the things that I thought I wanted had just been great marketing, either by society or the movies, and I had been inculcated with it. And so, you know, I realized like, holy shit, the foods I like, the things I do were really just programming. I don't eat fried crickets because I didn't grow up in Asia. If I grew up in China, I'd be like, when can we get some fried crickets, man? Things are really good, right? To me, it's repulsive.

But the only reason why it's repulsive is I didn't grow up eating fried crickets. And so almost all the things that I like We're programming, not innate, right? And so I realized that it was going to take a lot. And it's not that all programming is bad. Like some of them was like, I like it. Copy, paste, repeat. But a lot of the programming did not work for me.

It was that conflict of what I really wanted. And it was going to take some... Thinking and discovery to actually come to what kind of life I wanted, you know, how do these conflict with my values or my values, the right values, yada, yada, yada. And that was going to happen over time. It wasn't something that was going to happen like right away.

I wasn't going to release 20-something years of programming in a day, right? Give us a couple of the bullet points. What were some of the principles or tenets that you did end up replacing that actually you do live by now or you do chase now? Oh, there's a lot. I mean, how I react to people when they trespass against you, how I show up with kindness.

Like you're in Jersey City, right? You're going to a club. Somebody steps on your sneakers. Somebody might die, right? Like that's a cultural programming. What can you decide that you're going to do? I'm not going to be punching people in the face because they stepped on my sneakers in a crowded spot. Okay, so rule number one, I'm not going to be reactive.

I'm not going to be a hothead. Yeah, well, I'm reactive, but what are my response cries to certain stimulus, right? Everybody has certain stimulus, like somebody dies, somebody cheats you, somebody does this, somebody does X, Y, and Z. This happens, that happens, and then you have your responses, right, out of your toolkit. And, you know, I started to look at, out of all the infinite ways you can respond to a stimuli, why was I choosing these ways? Right? And the judgment was, does it work or not work for my goals? So there's no, you know what I mean? Like, it wasn't like a judgment in terms of like, this is the right way, this is the wrong way.

It's like, does this work or not work for my goals? What are my goals? So there's a lot of thinking and going on there about everything. Like if, you know, You see certain things in the news or people like, oh, this bad thing happened and they did this. And you're like, okay, why did they behave that way? Somebody insults you. What did you say? How did you react? You know, people write tons of books on this stuff, like, you know, controlling yourself or whatever.

But ultimately, it's like you have lots of stimuli and lots of responses and you're which ones work for you and which ones don't. And with the ones that work, you know, you rip them out and replace them with something else. That's been, you know, people ask us, we've done almost a thousand of these episodes. People like, what are some of the commonalities of people who win? And I always say, well, the first thing is like there's like for every rule that you read about in business, like I can point to many examples of people who have broken that rules and are equally successful and success is defined as, you know, they are where they want to be.

But the other thing is that there's this like internal locus control amongst winners, which is like basically I can only control me, how I feel, how I react to the situation. It's all up to me. Those are probably one of the only two things that are true that we've noticed about successful people. But that attitude that you just described is one of the common ones.

Yeah, essentially, it's maximum accountability, right? It's just like you are ultimately accountable. Do you know, you're a poker guy, you know Daniel Negreanu? Yes. So Daniel came on the podcast and, you know... Obviously, I wanted to nerd out about poker, but we asked him one other question. We're like, what was an important turning point in your life? I thought he'd say some tournament win.

And he was like, dude, I went to this self-help seminar. He went to choice. Yeah. I went before him. Oh, okay. Maybe you were the guy who told him. He was like five or six classes after me. He was like, someone I really respect had done it. And so, you know, I said, all right, fine, I'll go do it. And he talked about this maximum accountability principle where you had to write a story of your life or something that went wrong in some way you were wronged or, you know, something that went wrong in your life and then rewrite the story instead of in the victim mindset, but with 100% ownership of your part of that whole thing.

And he goes, it was the most freeing moment of my life. And it really stood out to me. I think a lot of people would benefit if they just rewrote one story in their life From the point of view of maximum accountability. Did you do that same exercise? Yeah, I've done that and many more in terms of accountability and not being in a victim mindset.

And it's a natural thing. I mean, we've taught it. It's in the culture. Your ego doesn't want it to be wrong. So, you know, getting the maximum accountability aspect going is a constant practice, right? Like you never get to perfection. You just, you constantly have to practice that. Can I ask about living this life with a family? Because you guys, you were talking about the white picket fence and stuff.

And what's funny is I never wanted any of that. Then I had kids and I actually had a retrain where I'm like, I actually do like being home at five and not going out at night. And I don't particularly love traveling that much because I want to be with my family. I wanted a more of a boring life. And I actually think a lot of young men in America probably need a little bit of where it's like, it's kind of nice to work 40 hours a week and also have a family that you're with all the time versus partying and going out.

How do you live this pretty dope life when you have young kids? I think your kids are more grown now, but what were you doing when your kids were in school and trying to like live this life where you're trying to be fulfilled? Yeah, just trying to balance it. I mean, I have 11 months old now. My kids are 22 and 19 and they definitely want to come.

Like I had a big party My daughter's like, can I come? Can I come? I'm like, yeah, you can come, but you can't stay. I was like, look, you guys have Sixth Street and all the partying. I was like, why can't us adults hang out and get our swerve off? Like, why are you going to come? But she wants to hang out. She's like, dad, you're cool. I want to hang out now.

Whereas before, I was like, dad, you're so strange. Like, why are you so weird? Like, why do you do this? Like, why do people know you? And now we hang out and we have a good time. And, you know, traveling, I take my kids traveling. We try and arrange a life. I'm like... Listen, there's something very seductive about a bucolic life that I want later.

You know, I ultimately want to be a farmer. And, you know, I've thought about how do I get everybody into life that I want to live? And, you know, balance for me is like the pendulum. Like, how do you manage the pendulum swings? your life is not perfectly balanced for each time period, right? It swings into I'm grinding really hard to I'm vacationing really hard.

I'm partying really hard. I'm relaxing really hard. I'm, you know, I'm doing spiritual work very hard, right? It's a swing, right? It's never the pie is cut evenly each day or even each month or even each decade, right? Like this might be the decade of, you know, learning all this shit and then I'm a doctor and then it's a decade of practicing, right? It's a matter of like getting buy-in and enrolling other people in the vision and making sure it works.

You know, there's people who are, you know, military parents and their kids travel all around with them. And that's their life. And they make the best part of that life. There's some people that that's just who they are. They don't have an obligation to the United States government. They travel around with their kids and they want to live somewhere.

My wife and I were like, hey, we want to live in Japan for a little bit. So we're going to. pack up our little boy and go to Japan. It's really about just making it the best ride. There's infinite rides. I don't think one's necessarily better than the other. It's really just a preference. And then designing the life that you want and trying it out.

You know, there's nothing wrong with people that just like, hey, I just want a nine to five. This is a job. I'm gonna join the Rotary Club, you know, get a nicer car, go on vacation two weeks a year and then die. Like there's nothing wrong with that. It's just not for me. Hey, let's take a quick break. You know that feeling when strategy is done, the brief is written, everyone's aligned, and you realize someone still has to sit down and actually create all the content? That someone is usually you, and it's due tomorrow.

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Can you explain this idea of time buckets, not bucket lists? Yeah. The idea of, like, a lot of people think life is like, oh, I have a bucket list and, you know, like the movie, you know, a month before I'm going to die, I'm going to run around, do all these things, I'm going to be happy, right? My life is complete. And The main thing is, is that each period of your life, like you don't have one death, you have many deaths, right? There was the college you that died.

There was a single you that died. There was you with young kids that died, you know, first job, first startup, et cetera, right? And they're largely in age brackets, right? Like for most people. And so each period in your life, certain experiences are optimal, depending on who you are, the arc of your life. in that time period and don't transfer well to the next time period, or they don't transfer at all.

And so it's like, hey, if your life, if a satisfactory life for you was like, I want to go skiing in my life 500 times, well, the distribution of those ski trips are probably going to come earlier, right? And if it's skiing with friends, it's probably earlier, right? Because they get married, they have life or whatever. And if you just kind of like, oh, I have a bucket list ski 500 times and those activities get shifted later into your life, well, you've kind of f***ed it up, right? Like, because you're really not going to get those 500 ski trips.

And so life is like Tetris. You kind of have to get the order right in order to get the high score and fulfillment. And so, but what that requires you having kind of a good understanding of what you want out of life and thinking about like, okay, what I want in life with respect to my kids and my family and my job and my career, my own leisure, my own hedonistic activities, my own altruist activities, et cetera.

You're not going to know it all because life is discovery. Right. You don't know what you want. You discover what you want. But having kind of like a time bucket of each period of your life, maybe three to five year brackets and say, OK, what experiences, what choices do I want to make in this period or in this period, in this period? And when you do that, you go, oh, my gosh, I have this here and it should be here and this here and it should be there.

Right. And then you'll have a much more fulfilling life because you'll actually get to do both of them as opposed to f***ing up the order and not getting it at all. Do you do any type of annual planning? Yeah, we do kind of a period, time bucketing period. This is what we want to do. We know while Kai is under five, we definitely want to go live in a different country, particularly Japan.

And we're like, okay, how long is that going to be? Is it just going to be a summer? Is it going to be a year? Is it going to be two years? We're actively discussing how that fits. you know, what's going on. And then all the other things, you know, people have multifaceted, multivariate experiment running their lives, right? Like how do all these pieces fit in? And it's kind of fun doing that.

Do you sit down with your wife and you're like, okay, because we talked with Jesse Itzler and I think Sean does this now. Do you do this, Sean? Were you like Jesse where he plans his quarterly trips? I carve out three days now a year because it just seemed crazy to me that I wasn't spending 1% of my year just trying to think through how to spend the other 99%.

And so now I spend three days and I try to get creative and think about what I want this year to look like and what would be the most exciting version of the year. And then I put dates on stuff and I try to make it happen then. Yeah, that's awesome. I mean, we sit down frequently, but our life and our travel schedule is so packed and there's so many, we're reacting to a lot of events, right? Like we're in the...

Playing a game like catching events and trying to move them around. Can we go? But then the larger arc conversation, like where do we want to be and set up camp? What culture do we want to discover? You know what I mean? What activities? Those are ongoing. But what part of your life are you most dissatisfied with right now? And I ask this because I think when people listen, it's cool to hear somebody who's got their shit together and inspires you.

But also it's good to remember like everybody's still a work in progress. Everybody's got some level of what's about. They're still trying to shift around, whether it's their health or their relationships or whatever. I'd have to say health adherence right now. I got married four years ago. Four years ago. And I was...

8% body fat, VO2 at the top 1%, yada, yada, yada. And now I'm probably like 16, 18% body fat and VO2 is like barely at the mid for my age, which is not the way to be. And so I would say that's probably the most dissatisfaction. I got a lot of victim stories of like, you know, I get up twice a night because we have a small baby. I'm too tired to do the things, you know, just went through a pregnancy and just kind of ate like, you know, I was a prisoner on death row.

You know what I mean? Like, but that's just all bullshit. So like, I'm just being lazy and not doing the thing. So I've broken all the stay in top 1% health and I'm, you know, down in the mids or below in certain areas. That's not too bad, though. I mean... And it's also... Like, I just had a kid, too. And I'm... I was... peak. Now I'm a little less in peak, but it's like, for some reason I, in this phase, I'm like, I'll be a little less in peak.

I accept it. I would say it's actually pretty horrible because you're using the US averages and the US averages have like a 40% obese rate. So I actually think it's pretty, pretty bad. No, but I mean, looking at you now, looking at you now, I think you said you're 57. I could be like, you're, you're probably decently fit. Yeah, I mean, it depends on what you want out of life.

Like, you know, my doctor has a thing called the Centurion Olympics, and it's kind of like, okay, in the last decade of your life, what activities would you like to do? And they have like, I don't know, 50 or whatever activities, but you pick them. And the things are like, pick up a small child, walk a hike, have vigorous sets for X minutes, do these things.

So you pick 10 that are important to you, right? Be able to wake, wake surf is one of mine, right? Yeah. And they run the calculations on, like, here's your VO2 now, and here's the decline that you would have, like, for each decline where I'm at. And then the activities on one side of what you can do. And it's one of the things I tried to do in the book way back when, before, like, the technology and stuff was there, is kind of like, how many watt hours per kilogram of energy do I need to climb a flight of stairs to do X activity, et cetera? And here it's basically VO2 max is kind of like the best indicator.

And the things I want to do in my last decade of life, like 80% of them I cannot do at this current trajectory. So you're saying that bad like now, but I'm kind of f***ing future bill over. And I don't want to f*** future bill over that much. So you really have to think about that. Like this whole book is like think about the total arc of your life and your total fulfillment.

and the net present value of that. And I'm completely over future bill right now. Well, this is actually interesting because most people are probably over their future self. You just said you're screwed it up. What are you going to do to change? I've taken some of the capital and we just hired another trainer that's here that can work, come with on time.

I'm actually evaluating that person Or another person to be like, travel with me too, because I travel so much and that's always an excuse. And it's like, well, if I have somebody who just travels with me and they're a trainer, then I don't, you know what I mean? I got somebody to like keep that motivation and accountability. Like if I can't be accountable, I need to outsource accountability.

But I need to do whatever I can in my power to make sure that I don't f*** over a future bill. Yeah. You wrote the book, and the book has an amazing title, like one of the best book titles ever, and I've studied this stuff. I do think so. It's almost too good. You don't even need to read it. Yeah, exactly. You can give somebody the book cover, and they should judge it by its cover.

So the book is called Die With Zero. What was the original title going to be, and would you wake up one day and have that? Did you hire somebody to come up with that line? Where did that come from? No, we, we, it was just like, we came up with like 10 or 20 titles. Like, what is this book going to be? You know, die with nothing, maximize your life, like kind of like descriptions of the book.

And the ultimate concept is, is that like you use all your resources here on this vacation on planet earth. You leave it all on the field. Right. So you die, you know, and people are attached to the money aspect of it. So die with zero just hit. It's like there it is. And it's also die with zero regrets. Right. Like it's like if you if you leave everything that you do your best and you leave everything on the field, you have zero regrets.

Like most people say, do you have regrets? I go, yeah. And all my regrets are a version of when I didn't do my best. So whether I lost my temper or I did this or I behaved this way or I was fat and out of shape, it's like I didn't do my best and therefore I have regrets. When I do my best, that's all I can do. There's no regrets. It's unfortunate.

Like unfortunate things still happen, but I don't regret that. Like I don't regret my ass, you know, what I'm accountable for. And then the publishers love this. Like, you know, there was a little bit worry about like, well, people getting on airport tickets. Riding through an airport, you know, and the air is like, die. You know, like, that's going to be hard sailing in an airport.

But it was like, it just hit. It was provocative, and we went with it. I've used your book. It's changed two parts of my life. The first is now when I take vacations, the way that we roll is we get a big house. And for those who can afford it, we say, here's the dates that we are going. Everyone's welcome. Come and do vacation with us. Like to like my parents or my in-laws.

And it's pretty awesome. It's made vacation so fun. And then the second thing is I have in-laws who created a business and they're very successful. And one day they're having a conversation. They're like, look, when we die, here's what we want to leave everyone. And I was like, look. Here's what I think you should do. You're not asking for advice, it's your money, do what you want, but you should do one of these three things.

The first thing that you should do, give it to us now. We don't need any money, so that's probably the least good one, but if you do wanna give us money, give it to me right now. But don't do that one probably. The second thing is go and do something for yourself. Be selfish. Whatever you wanna do that makes you happy, just go and spend all the money on yourself.

Or the third thing, go and do something that we could all enjoy together. You guys have been talking about getting this bigger vacation home. don't even think twice, get it and we will all enjoy it with you. Or if you want to go on this awesome vacation, pay for all of us, we'll go with you. And they're starting to do it. And it's made life so much more fun.

And so they actually got a new vacation house that like, it's kind of like vacation homes are like definitely a hack for like really wealthy people. Because if you get a place that's big enough for everyone to be really comfortable, you 100% spend more time with your family. That's what I've noticed about that. And it's changed everything for us.

Yeah, like now, because I had this conversation with you, they're going to have a more fulfilling life and they're not going to be like 85 on their deathbed going like, why didn't I do this? Or I didn't get as much time with so-and-so during this time period, et cetera. Like you've completely eliminated that future regret. And it still exists, by the way.

Like there's still fear. Like everyone, particularly if you're like retired, you're like, will I have enough to take care of myself? That still exists. But I do think like having a large dose of enjoy it now is good. Yeah, I mean,

what fear should be greater? Having a little bit of money and eating beans or wasting your entire life and missing out on your own life? So I think for me, it's the latter. You must get stories like this all the time. Somebody reads the book and they make a change, and that's obviously got to be fulfilling. What are some of the stories that stand out to you, or what's a pattern you've heard from a lot of people who've read the book, kind of like what Sam's saying, a change, a decision? What comes to mind is a lot of the inheritance one, because everybody's kind of like, that just...

it makes no fucking sense. It's so obvious. And then they read it in a book. You're like, you're right. This is so fucking obvious. Like, why am I waiting to die to give somebody their inheritance? Like an inheritance shouldn't be a bequest. They're not kids. They're 60, et cetera. So that's like most of like the older cohort, like, that have discretionary income or they plan on leaving something behind, they've somehow changed their estate planning and they're actually taking estate planning seriously.

Other than, oh, when I die, whatever's left over is going to go to this person, this person, this person. The second one is like, we've completely, you know, people shifted retirement dates. They've completely rethought what they should be doing in the time bucket that they're having, or they've done it for their parents. They're like, I've made my parents retire and their sole job is to hang out with their grandparents.

Like I've had that, like, that's it. Like your job is now to hang out with the grand, I'm sorry, with the grandchildren and, and, and, and just spend time with them and be around. Right. Or I've done this or, you know what I mean? These things I was putting off or, you know, just kind of woke up to what I wanted. And then they, they're now doing that.

What about people who don't have money? What are some interesting examples of people who have read your book who are retired teachers or are teachers,

not wealthy people? They have money. If somebody in the military reached out and it's like, yeah, it doesn't make sense. I have a guaranteed pension until I die. Why am I saving up all this money? Like they have no risk, right? Like they're a military pension, right? They have no risk, right? Like, so they're like, what is this lump of cash doing there, right? When I know I'm going to get X per month, like they started going to live life.

The other people that want money is like, they're making different decisions, right? Right, because really it's about how do you allocate your time, right? It's really about choices, right? Money is just one of the tools you have in your toolbox, your health and your time, right? And so like they're making different decisions on how they spend time and who they're spending it with, you know, that costs no money, right? Making a decision to go see your mother or go play cards with the boys, right? Or play basketball with the boys or watch TV, right? Neither decision requires much money or money at all, right? It's, but how do I allocate my time in this time period? And

where does my time belong, right? Some of the people are like, yeah, I'm now driving my kids to school and not complaining about it, or I'm reading them books more or et cetera, right? It wasn't a money decision. It was a, how do I allocate my time decision? And then I get some of them was like, the health part really hit me. The idea that I won't be able to do certain things in the future.

People are like, I'm getting in better shape, right? So there's things like that. So people look at the three variables and they look at kind of like, which one, which tool am I not using properly? A lot of people, most of it by and large focuses on the money, either earning it, right? Like I'm spending, there's the other side, I'm spending too much and I'm screwing over my future self, right? There are things that should be delayed, right? But, you know, somebody has something to optimize to get a more fulfilling life amongst those three tools, their wealth, their health, and their time.

By far, my favorite story in the book is at the beginning. It's the story of when you were working somewhere in your 20s. So you didn't have a ton of money at the time. You had a job. It's my least favorite story.

And he goes, and you're like, dude, I can't just, how are we going to get six weeks off? He's like, we're not. We're going to quit and we're going to go and we'll try to get a job when we get back. And you did what you thought was the responsible thing. He seemed reckless. You seemed responsible for not going. And, you know, you're like, as soon as he got back, I could see the glow in this motherfucker's face.

And I knew I did it wrong. Like he, he had made the correct decision. And he got, his job was waiting for him. We were f***ing peons. I mean, like, what were we doing? What did we have to lose? And then you said you, you finally went in your thirties and you're like, you know, what's not cool? Staying in hostels when you're 33, backpacking through Europe by yourself because your friends aren't going with you.

Sleeping on trains, you know? Yeah, you're a millionaire, but I'm sleeping on trains and going, it just didn't happen. I was too bougie. You know, there's not just the physical aspect of it. It's just the aptitude, you know, like kind of like your personal, you know, like glow sticks and raving in clubs used to be fun. You know, it's not as fun anymore.

When I was in my early 20s, I used to call myself a $50,000 millionaire because I would host these conferences and I would make 50 or 100 grand or something. And then I would go and ride my motorcycle across the country or do some type of trip for like six or eight weeks. And it literally costs like... I think I paid $1,800 for a six-week trip to ride my motorcycle.

I used couchsurfing.com, which was fun, right? It was fun to sleep on someone's couch and get to know them. And it was the most fun that I ever had. And I look back at that, and I was like, I'm so thankful that I was kind of silly at that era and was willing to do that. And it was so much fun. And it kind of creates this like... write a passage a little bit when you do travel like that when you're young and you are reckless.

And it was so much, it was so impactful for my life. And I would never do that now. Like it was too grimy. I don't want to do that shit. Yeah, I'm so envious of his story. I'm like so envious. I'm like, God damn it, I want his life. You know what I mean? Dude, I get envious of my younger life at times. And what's interesting is I don't want that.

If you offer that, I could go do that now. I don't want to do that. But it was fun to want that then and to be able to do it. Yeah, that's a great example of time bucketing. Like that experience belonged in that time period and doesn't transfer well to the next one. Even though you can still do it, you just don't want to. I don't want to.

So have you completely slayed the money monster? Like, do you wake up and do you have businesses? Are you like investing? Are you trying to do deals still? No, I have businesses. I still work. It's not that you can't work or you can't enjoy solving the puzzle. Like, we get addicted to puzzles and those puzzles become fun to us. It's just that, you know, using your resources, you know, I use the resource, right? Like, there's no amount of capital I can't convert into fulfillment for me.

What do you do now for work? So I have two startups. One's called SkyFi. One's called SimMax. One's a geospatial intelligence platform, kind of like Uber for satellites. Like you can order on your phone a satellite image. And I have an intelligence firm called SimMax, and I still trade. I run the hedge fund. But I make sure that in each time period, the things I really want out of life, right, that there's value into doing that.

And so if I was sitting here and I go, you know, To the day I die, I'm not going to spend the money I have. Like, I have no need for any other money. There's no additional fulfillment to a marginal dollar. Quit it all in a heartbeat. Right? Just stop. Like, what are you doing? You know, but there is marginal utility for me. For some people who their concept is enough, they hit it.

Like, hey, I just like playing checkers with my friends. I grow potatoes in my yard. You know, I go to school, whatever. You know, I do whatever. Like, for them, it's a different decision, right? Like, it's like, no, I'm wasting my life. What is it for you? Because you said, ultimately, I want to be a farmer. So, that doesn't cost that much, right? No.

So, my farming years are really, you know, like, I know I'm going to be spending a lot less money in years, but like... If I keep my VO2 here and higher, as I should, there's a lot of other activities and things I would like to do. I really fell in love with yachting. They're very expensive. I do like private travel. It's a time saver, and the party actually starts when you get on the plane as opposed to when you get to the destination.

So I do think it's worth working for that. But at a certain time, I'm almost getting close to the age where it's not really worth working for it. It's not worth giving up current hours of bill and other activities for future bill to have this thing. You know what I mean? And so I'm constantly measuring that. And, you know, it's also probabilistic.

Like I could lose money. I could make a bunch of money, et cetera. Dude, every man, it's like they think of either World War II or the Roman Empire, and they think of retiring on land and being a farmer.

I did that once. I tried it. It wasn't for me. Not in that time bucket. Yeah, not in that time bucket. But walk me through this vision. What are you going to do? You're talking about later in life? Yeah. What's this farm vision? I mean, I just want to have like a hobby and not like a big giant farm with a tractor, right? How many acres? Like a couple acres, some gardens, maybe grow some tomatoes or whatever.

You'd be surprised. That's like a garden. It's like a large, it's a large garden. A large garden. You live in Texas. Ranches are pretty big. I had 20 acres. I don't want a big ranch. I had 20 acres and the Texans called it a ranchette. Yeah, that's a ranchette. You need like a thousand acres to like, I got a ranch, you know? Yeah, I thought I was going to be cool.

They were like, sick yard. No, no, no. I want like basically a large garden, a big gardener, some bees, you know? I had bees. Yeah, you got the bees, you had the whole thing, right? Yeah, I had bees, I had honey, it was great. Beekeeping is probably the only ranch-adjacent activity that is not a lot of work and is worth it. Yeah, and I love the pollinators, so that would be great.

You know, just kind of enjoying grandchildren and friends and visiting and like, you know, when you're younger, you're seeking adventure, right? Right. You're looking to create a story. Right. Like you're looking to create stories and memories. And when you're older, you have stories looking for friends to talk about them.

And so when you're older, when my knees are finally gone, I guess there's knee replacement surgery, but my back and I'm tired and my mental acuity is on the decline, lung capacity is on decline. The things that I will do because it's difficult to walk four miles or it's difficult to whatever, my world is going to shrink. And I'm going to be looking for friends to tell stories.

And I want to have a bunch of stories to retire my memories and do the simple things, enjoy the simple pleasures of life. So a lot of times people at the podcast, they'll reach out to me and they're wondering, hey, Sam and Sean, how do you meet all these amazing entrepreneurs? How do you find all these stories? Well, I have a hack. You see, I actually have a community called Hampton.

It's a community for entrepreneurs doing at least $3 million in revenue, although we do on average something like $25 million a year in revenue. We have the founders of DoorDash, of Figure, of Bluetooth. All these amazing companies are part of Hampton. And what's interesting is because of the environment in Hampton, which frankly is very similar to my first million, we have a very unique high trust environment.

When people apply and go through the vetting process, they're put in groups of like eight or nine other entrepreneurs, and they get real about everything that's going on in their life and in their business. And sort of like when people listen to MFM, they get inspired to come up with new solutions for business. That's what happens in real life in Hampton.

It's life changing. And so if you're a founder of a startup that does at least $3 million in revenue and you just want to go ahead and pull forward five or 10 years worth of success, then check it out. The URL is joinhampton.com. Again, the URL joinhampton.com. When was the last time you worked from an office and has that impacted your life? I have offices, you know, but I don't go into office.

I mean, I have this like kind of like an ankle monitor called a cell phone that allows me to trade from anywhere, but it's always with me so I can trade and do work from anywhere. And so it's like, you know, it's like I am tethered to the work world, but it does make for great office spaces, right? Like when I'm on a boat on vacation, my office is the boat on vacation.

Wherever I am, that's the office, right? So it's both a blessing and a curse because it extends the amount of neurons that I apply to these puzzles, these work puzzles. And I'm not so sure if that's a good thing or bad thing. I'm constantly evaluating it. given how old I am. Sean, do you miss having an office? Because Sean has the same thing.

Diego comes and works from your house. Not at all. I did have a commute at one point where I was biking and walking to work. I think that's the only part I miss is the habit of getting up in the morning and getting outside and walking or biking. But now I just do that with my kids' school drop-off. That scratches that itch for me. I never...

I never want to go to an office again. I like having a dope home office and I have one or two people that will come over and work from here. And then they get out of here halfway through the day and then I'm just back at home. I'm not looking to go into an office. You love that, Sam. You love going into an office. I do like it. So I go to my office three days a week.

I'm at my office here. And I live in Manhattan. And so it's nice to have the separation because we don't have Texas-sized houses here. But there is something that I like about getting dressed up. And I like laying out my work clothes the night before. I kind of like that routine. I know it sounds like- My daughter loves that too. Dude, I'm kind of a square in that regard.

I like the routine of like getting here and going home. There's something about it that I enjoy, but I do find myself significantly more productive at home. Yeah, I mean, you know, when I talk to people about like offices or going with it, you know, when we deconstruct it, it's like, well, I like the people and I like spending time with people and I like, you know, the walk here or whatever.

And I'm like, you can do that without having the office. You can actually... Take those people out to dinner and spend more quality time as opposed to right next to them while they're doing this and you're doing this. You can actually just take a walk to Central Park and back and forth and make that part of your routine. You can actually have them have a walking, working thing and walk around the track and work with the phones and devices.

You can reconstruct it and it might be better, but some people, whatever your value systems are, I think it's better for young people, though. And so one of the reasons my company, we have an office is I remember I was talking to one of our employees was in Manhattan and I was zooming her when she was in her shitty apartment. And I'm like, this is a horrible existence.

Are you miserable? She goes, I hate this. I was like, we got to get an office like this. It was it's not particularly fun, I think, for a 22 year old to be working from home. I think it's a lot more fun when you have children or when you're the boss. Yes, I agree that. Like, I think we need to help. The younger generation connect with other humans because there's so many devices that are actually disconnecting them from other humans.

It's the illusion of connection with social media, the in-person mixing and hanging out and discussions and meeting that art is being lost amongst younger generations. So I do, I am a proponent of that. Sean, did you see this story about this painting that he just bought? They did a good job of, I think it was on the Wall Street Journal, covered this painting bill that you got.

I think it was called Sugar Shack. Have you seen this, Sean? I saw this a long time ago. It was a YouTube video, right? You spent some ungodly amount of money on this painting. What's the story? I mean, it's a very unique piece in American art Particularly because one, you know, you say like, well, who was the African-American da Vinci or whatever? And the answer is no one because they were slaves.

And so it wasn't until after slavery and the formation of families and they started growing up where people can actually afford paintbrushes and have the time to actually paint. And so you kind of get like your first generation of like masters, African-American masters and the narratives that they would paint about. born in like the 40s or 50s or second generation, depending on what you use is like 1910, 1920s, and then the 40s.

And so this artist was a football player. He was an artist in an athlete's body and started painting. And he was painting, and this particular painting was about a sugar shack, which he had passed growing up in the South. It's like a party house about black joy in the South during segregation, which is a uniquely American theme, right? Like you can still live ice rink or whatever, but it's uniquely American.

And not necessarily from like, oh my gosh, slavery was bad or segregation was bad, but just like, you're just not going to get that narrative, right? It's like jazz is the only original American art form. Like this painting is very, very unique culturally by like the first or second generation artists And it was featured on Marvin Gaye's album that won a Grammy.

And it was on the opening outro of Good Times, which Norman Lear was like kind of the first producer to put stories of young Black families on TV back in the 70s. And so this is very culturally relevant stuff. Very historically significant. A narrative that's not going to be painted in China or anywhere else, etc. So it's uniquely American.

And I was in love with it. I had seen it since I was a kid. And any Black person in my age range knows about this painting, has seen this painting and other works by Barnes.

And when it came up, John Arlo messaged me, sent me an email. He goes, hey, isn't this the painting you've been looking for? I've been looking for it because there's two copies of it. One, it was painted. It was in the back of the artist's car. Marvin Gaye sees the painting, freaks out. He's like, can I have this? I must have this for my album.

And when the biggest music star of the time asks you for a painting and you're a struggling artist, you do what he says. So he changed the painting and painted on Marvin Gaye's thing. And it's on, I think, his album called After the Dance. But it wasn't about that. So he went and made another copy of it. He painted another exact copy of it for what the painting was really about.

And so I tried to buy that piece from Eddie Murphy. and basically got crickets, you know, like wouldn't respond. And then John called me and goes, this is up. And I almost cried when I heard about it. And I was like, okay, I'm not going to telephone auction this thing because what if the telephone goes down? Like I had all this nervous, I'm going to fly.

It was the first live auction I've ever been to and I flew to Sotheby's and I stole that painting, you know? So like a lot of people focus on the price and they're just like, oh, you paid this much. There was a one of four Warhol that went for a hundred million dollars. What did you pay? I don't know what you paid. The total price was $15 million.

Describe the auction battle. It was chaos because they did some chicanery. So there's an evening auction and a day auction. And the evening auction is particularly the more expensive works, right? But this had an estimate that did not fit the evening auction, right? Like an estimate of $252 million.

it's like it was in a hundreds of thousand top million right like a millions and i was just like you know people were like why the is this in the evening auction but so i knew there were some players who who wanted to get this thing but i figured like okay oh there's a bit of three million take it scare everybody off and walk out the building with this with this painting and And it just, like, was chaos.

Like, everything was pretty standard. Like, you know, whatever it was. Andy Warhol, Pinto, what else? Do I have a bid here? Do I have a bid? This was like a trading pit. It was like trading places for the first five minutes. Then you can hear me yelling out, two million! And then, two million, three million, three million, four million. And it just goes crazy until we get to, like, around seven million.

And it's like... three people, then two people, and then it's just I and this other bidder going back and forth on this painting. You could see them, right? You're there live. They're there live. The funny thing is the guy who was bidding against me was like two seats ahead of me. He was empty row and he was right there. And it was just he and I.

going back and forth and me pausing and me thinking like, what is going on here? Who was he? I don't know. He was an art consultant, a very respectable art consultant, working for somebody who never revealed who the buyer was. The only thing that was odd, aside from me, you know, I told... is that during the middle of bidding, which, you know, bidders don't talk, you don't talk to each other, whatever.

He turns around to me, he goes, I'm not going to stop. And then I said to him, well, then I'm going to make you pay. And then, you know, people kind of like chuckled who heard all that, laughed, and then it kept going. And, you know, during the, before the auction started, I told my wife, I said, listen, babe, don't worry about me if I faint or anything, just keep bidding.

And this is a true story. I said, do not. And there was like a painting that went before and I was like, I should, I should, this is really a good painting. I should buy this. I was like, no, you need to save your money just in case. Thank God. Because I was way over the amount I was willing to pay for this before the auction started. Going in, what did you think your backs was? I thought I was going to pay like three to $5 million, you know? And it was what? You said 15? 15.

At the end. Did you, at the end, were you wobbled? Were you shook a little bit? Or you were like, I'm going. I was in, my eyes were watering. I was so happy.

What do you feel like? You feel like a historian or something? Like you're the steward of history? Why is this so important that you have? Yeah. I mean, like the role of the collector is to signal to future generations what is worth preserving. So what you see in museums, et cetera, were the commissions of wealthy people back in the day or things that they collected.

You may not be seeing the best art. Actually, statistically speaking, you probably are not seeing the best art, right? Like some of it was probably burned or it was in people's houses or whatever and didn't make it or didn't show. What you're seeing is what prior people had signaled to future generations what was worth preserving. And so given that context of this piece and in the historical context I gave you of like American art, particularly African-American art, there was just an arbitrage going on because of the perception, right? There's a lot of people that are like, oh, a black guy should own it.

And I'm like, no, a black guy shouldn't own it. The world should own it. A Russian billionaire should own it. But we get to steal this because people have these kind of like, you know, historical racism in the art community where museums would not collect African-American art and they would not put it in or not have it. And then now, Kind of that makeup here, that kind of like social stigma of, you know, who should own this art, whatever.

It's stuck in even the black community. I'm like, you guys are idiots. Like it's creating an arbitrage between the valuable things that should be signaled and preserved for future generations and what the market is paying. So I was ecstatic. I felt like. You know, I arbitraged the market. I like I had made it. I had finally made it that I can actually own this painting that I used to watch on TV all the time.

So I was super happy. That's so awesome. It's also awesome to like. I think it's cool to be like this kind of like man's man and also like be into some of the other shit. It's like this, it's a very eclectic person. Did you guys see that story about Sylvester Stallone? Apparently in the 80s, he'd bought this Monet. I think it was called Haystacks.

I think he bought it for $110,000 in the 1980s. Years later, he had some bills to pay or something like that. And he sold it for 3 million. And then like five or 10 years later, that same painting sold for $130 million. Yeah.

And he was telling this story and he was like, I was so foolish to sell. He's like, because art, it doesn't require upkeep. Like I don't have to like move it or fix it or repair it. He's like, I was foolish. Why did I sell this? And it was a really cool story to see. But also it's like Sylvester Stallone, you know, he's supposed to be this like guy's guy, yet he writes this badass movie by himself.

So he's clearly has an artistic side and he spots a Monet before the world does. And it's just kind of cool to see like an eclectic human being. Oh, you should, you should watch the, there's an interview with him about Rocky and the characters and him writing the characters. he is an artist. He wrote that and it's like, when he talks about the development of the characters and what it's about, it's an amazing thing.

Like the sequel's all about the boxing and Clever Lang and whatever, but like, and he became an action star, but like, he's an artist. Like people are multifaceted. So, you know, you look at like the highlight of my life on Instagram or you look at whatever and you might like have an idea or a good view into a certain facets of people's lives.

But like, everybody's a multi-cut diamond. And some of those facets that you don't see are actually a bigger part of their lives. In a strange way, by having that bidding war, telling this story, buying it at the price you did, you increased the value of the art, right? So it's kind of reflexive in that way where the art actually increases in value because you paid more and because of the way it went down in a strange way.

Yeah, I mean, I signaled to the market, Barnes's works are important, at least his A-grade works, right? Like every Arctic has their A work, their B work, their C work, their D work, and, you know, et cetera. And so the market got a signal and there was another piece at auction that I wanted to buy and then I couldn't afford it because- You know, that was a piece that had I bought that first, I probably would have bought it for a couple hundred grand.

It went for like two million to some Asian buyers or something like that, right? And this was the day auction, right? This is the cheaper stuff, right? And so I completely reset the Barnes market You know, and it wasn't me. It's just the market became aware, right? Like, you know, when people like, well, why did you pay this much? And why is this significant? You know, I had like three, you know, Artnet interviews and Wall Street Journal and interviews.

And I went over the thesis and everybody's like, you're absolutely right. There's this photo of you like holding up your arms. It's a great photo. I would have held up my arms when the guy turned around and said, I'm not going to stop. And then you had a cool thing to say back. You know how hard it is to have a cool thing to say back in the moment? I would have already been celebrating the victory of having the cool one-liner ready to lock stock and barrel, right? And then not like 10 minutes later thinking of what I should have said.

No, I don't know. It's just it just flowed. You know, it was it was, you know, some people it's like, I got to have this car or I made it when this this this was the thing, you know, and I'd become a peon, minor art collector, a thief of collecting black works. And my friend John Arnold was helping me. He's an extremely astute collector. He saw it first.

He's like, would you? I said, what do you think? He goes, it's exquisite. And so, and he's the one who notified me because I was after it. And kind of guide me on like, collect what you like, you know, collect A-works, et cetera. And so anyway, yeah, it does help, but I don't expect to close the arbitrage in my lifetime. I'm just, you know, I get to, Show people and carry it.

Where's it now? Right now it's on loan in a museum. I think it's in Ohio. And then it's going to Art Basel on loan. And then it's on loan. It's on a lot of loans. People borrow it. How does that work? So they're paying you to be able to exhibit it? They pay the insurance and they carry it, et cetera. When I first got it, my kids were like, don't you dare bring that to the house.

You can't have $15 million hanging on the wall. We're going to get robbed. And so they were all scared. People know who you are and they're going to come take the painting. So

it's on tour right now. Man, thank you so much for coming on. You and I, I don't know if you know this, we've been trading DMs back and forth like four years now trying to get you on. You know, we have all types of amazing people come on. I think that you're, and we don't look up to everyone. We like most of them. We don't look up to everyone.

But I think you're one of the handful that we, you really have some parts of your life that we really, really, really admire. And yeah. you know, we ask ourselves like this flavor of advice, what would they advise that we do in this period of our life? And so you're definitely in the mix. So we appreciate you. Yeah, I tell people I'm not a role model, but I can be an inspiration.

You don't want to live my life. I make way too many mistakes, but you can, you know, the words are pure, right? Like a lot of like, and I don't want to be famous or too famous. You don't want to be too famous because you can't get naked at a party. And, you know, without the end of the paper, I always tell people, and I reserve the right to get naked at a party.

It's kind of my line. And you also then become in service of this persona, right? Like if you become that guy and the words are pure, right? The words in the book are pure. The stories are pure. Like the concepts are pure. I am- But you're kind of gotten famous. You're sort of famous right now. Like Z level. Z level is okay. Popular. Yeah.

Z level is okay. You know what I mean? You don't want to be like, you can't enjoy life. You can't go walking. Wait, were you popular before you had the book? Yeah, for different reasons. I was trying to... Poker? Poker. I was running around a hedonistic life when I got divorced. I was running around girls and I was like gonna... I was gonna go climb the fame game, right? And I was like...

You were like a Dan Blazarian guy, weren't you? Yeah, I was like a... I was like, I'm not a Dan Blazarian guy. He's a different guy. But like, yeah, I was in this whole like... I'm just going to date a bunch of people. I'm going to have like kind of this movable feast of a life, you know, like the sun also rises, Hemingway type life, you know what I mean? Traveling around, living this life.

And I saw the value and fame was like, this is great marketing. Like you can get a lot of girls, you know, being famous. And then I saw... That it robs you of your life. Fame shrinks your world and you go into a bubble. You can't walk around. You can't do things. You can't whatever. And I saw that with Michael Phelps. And I saw that with Dan.

We would go places like, okay, we're in Capri. We're going to go out and walk these shops or whatever. And they can't go because of all the, you know, Dan, Dan, Dan, Michael, you know, all those types of things. And I thought, oh, that's hell. That would be hell for me because I like traveling and I like exploring new cultures and I like meeting new people.

And if I have this fame persona that like, one, can't do it without security, people constantly interrupt you. And two, you play up to that, you become a slave to that persona, right? If your persona is I'm the nice guy, then you're always playing the nice guy. Even when you don't want to be nice or you need to be forceful or assertive, right? Not even a dick, but just assertive, right? Or if you're always a calm guy, you have to always play the aggressive.

Or if you're always the bodybuilder, aggressive action star, you're always playing a role of like, I'm the rock. Can you smell what I'm cooking? When you might be into like lilies and bee farming, you know, you have to play up to it. And so I care about being able to have the most fulfilling life. And so that's why you never want to be that famous.

You're going to write another one? My wife says hell no. It takes a lot of time. But actually, it is seductive.

Do you guys know Tim Urban? Of course. And so he's like, we should write a book together. We have a bunch of ideas and write a book together. That's a crazy combo. He just goes, that would be fun. He goes, yeah. So I've been like, yeah, I just need to kill a couple of projects so I can have the time. What topic? Right now I have a no new projects thing for my wife and she's right.

She's helping me be accountable to have the most fulfilling life. But

this is seductive to me. What topic? Don't know yet. We've been thinking about a couple. What are you obsessed with? Well, there's a lot of things on relationships and purpose. The one thing about the book I don't tell people is like, Whether whether their values, you know, like you choose your values. Right. And what what is fulfilling. And so I have a couple of theories about purpose and fulfillment.

Like, I think there's a lot of purpose born out there. I think it's complete bullshit. I think the purpose of life is to be happy and purpose comes in design. And there's a lot of design cues from your biology that tell you your purpose, the same design cues and pair of scissors that tell you it's for cutting. Right. And so I think I have some theories about that.

I won't go into the long story about it. There's a couple of things. Relationships. Like a lot of people wanted the cookbook version of this book. They're like, great. I get the high level concepts. Tell me what to do, you know? I don't think I want to do that, but, you know, I can mix in some of that. Well, a lot of the books now are having like handbooks, which I actually think, I think those are cool.

Like I know that there's Design Your Life, which was that Stanford course. They had like a handbook. I did that like 10 years ago. It was awesome. Nobody does the handbooks though. Dude, it was great. You buy it though. Nobody does them. You can give it to them. Nobody's going to fill it in. Yeah, it's tough. I left it for other people to write the computer programs, to write the handbooks, to actually do the math, you know, to have, you know, I want them to be in my church and go build it.

I kind of wanted to be like Jesus and just like, you know, go forth and build a church. I'm out of here. You know what I mean? That type of thing, you know? Like, I don't want to be the guy, you know? A lot of people write books to be the guy. I don't want to be the guy. I want to live my life. You don't want to be Jesus, but I don't want to be the guy.

I just want to be the guy. Jesus got nailed to a cross, my friend. Like, there's a price to pay. Exactly. I get nailed to the fame cross, right? Like, a lot of people, like, write books and it's like, they have the chorus and the podcast and the thing. As a matter of fact, there's a guy coming out named Austin. who is like the number one fan, my number one fan of the book, gives out the book all the time, spoke at like conferences about my book.

And he's like, hey, can I do a Die With Zero podcast? I'm like, have at it, have fun.

I'll do one show, but I don't want to be the guy, right? Like I wrote the book to like have a fulfilling life, not to get famous. Well, we appreciate you doing this. You're the man. All right. Appreciate it, guys. Thanks for having me. All right. That's it. That's the pod. I feel like I can rule the world. I know I can be what I want to. I put my all in it like no days off.

On the road, let's travel never looking back. All right, my friends, I have a new podcast for you guys to check out. It's called Content is Profit, and it's hosted by Luis and Fonzie Cameo. After years of building content teams and frameworks for companies like Red Bull and Orange Theory Fitness, Luis and Fonzie are on a mission to bridge the gap between content and revenue.

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