$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 out of here Like I 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 He's like 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 days off on the road. Let's travel never look on that note. Welcome to the show Thanks I don't know if you know what you're getting into. So basically, uh, 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, uh natural gas derivatives started out as like Assistant assistant peon as a clerk on the new york mercantile exchange floor when the natural gas futures contract started I went really wanted to get into that Became an over-the-counter broker made like moderate money as a broker, but really hated brokering And then when uh deregulation hit 19 or 1995 Uh, they were recruiting a lot of people from new york to come run the derivatives desk in, uh, houston, texas I moved to houston, texas and that's when I started as a trader Making real money sam when he when he says and 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 we we create websites that like 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 and and selling it to someone else who needs it? I 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, etc How did you get good at knowing if the price will go up or go down when everyone every other smart guy is also Trying to figure out if the price is going to go up or down. How do you how do you win that game? Well, you know, there's there's you know, we're really not in competition with the other smart guys Like we're kind of glorified insurance agents Like we we don't want to trade we get induced to trade based on what the market is doing versus what we perceive for that 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 a an even more dumbed down example? So like for example, uh a company Needs to acquire a bunch of oil. Are you the middleman who would go and acquire it and you try to get uh, yeah Let's say the the winner's coming and people are afraid price is going to go up and generally I was always short Right because people always afraid price is going to go up in a winner for natural gas and we'd be like, okay We'll sell you futures contracts They 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 winner risk premium Usually bled out and the prices would go down and most of the 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 Uh, 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 absolutely wrong because I was younger when I look back That it's okay to have no money in 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're like, okay if I get blown up here trading You know, I 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 is that I was very young and maximizing risk at that age is probably the way to go Uh, and I should have been fully concentrated and 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 Etc. 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 when you do well and you were saying you said why I initially made this, uh, this this pool of capital uh 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 I was kind of climbing the the earnings tree First as a broker. I was an otc broker, which I hated I was good at right, but you're gonna make six figures You know You can make more if you like start a firm and be part of a firm But it's I 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 you know, I 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 the howard marx redalio 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 buffet 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 Uh, you know i'm buying an etf and I realized that the underlying hundred stocks underneath it are not priced exactly In 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 in two. We weren't the arbitrage. We were one in two. So the idea is is that you know, the market is comprised of a lot of people who who are You know some people punting around and just just straight gambling Uh 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 We'll have a position based on that Irrespective of your superior knowledge. Um 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 how bright you are Uh, you need to have that temperament that stoic temperament Um that ability to handle losses and um or be robotic about trading But your temperament is a little bit different and I kind of find it more interesting Um, so like we've had like you said howard marx. Let's say howard is sort of an academic He's like part philosopher part academic same with ray dalio like they're they're they're sort of um, this 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 hl hunt, you know, one of the guys who like, um 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 fun 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 fun. You can lose a hundred percent, but my fun can also return 300, right? So like it's really the expected outcome. And what kind what are you trying to do here? Did you ever almost lose it all? Yes a couple times. Hey, uh, 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 uh, 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 bill What were the 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, but you know in 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 like right like you're saying like, oh, they're cowboys These insurance 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 army, you're not going to get a lot of insurance And so unless you're in the arbitrage game, uh, 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. Uh, let me ask you a question you uh, You seem today like 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 Like you don't you know, it was intense like the intensity of trading is crazy You know, you wake up at certain times to check what's going on in tokyo and blah blah blah Yeah, were you 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 Uh, 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, um, 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 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 dude build build a company that's gonna sell a product knowing what I mean No, I would I would have went into equities It's just much bigger and it's you know guys have six billion dollar funds ten billion dollar 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 Just a skill set translate. So equities meaning you would you would evaluate different companies and figure out which ones? 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 are quite amazing on these giant funds, right? Like you have a six billion dollar fund charging one one and a half I'm, like what fund costs that much money to run? Like it doesn't right? So like you're you're you're you're Your maintenance becomes a profit center and then your upside is just amazing just in terms of the notional dollar amounts And so in terms of like personal wealth, like how could i've 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 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 uh 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 when you um 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 goalpost and say 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 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 rock star 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? Right. 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, right? And then everybody kind of parrots like I want to be a millionaire before x date, right? 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 till later in life that I really um 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 not a number uh, just given the fact that Your body is a decaying asset and its ability to convert that money into uh fulfillment and useful experiences declines net rate of decline starts approaching affinity as you get close to your deathbed and so Like 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? Did you read something? Did you experience something 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 set off a whole bunch of other thought processes about, okay, I'm exchanging hours of my life for capital. What's that capital for? 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, and why? That started coming along, and then really thinking about death, and when do certain things happen? 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? 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 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? 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. 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 do these variables fit? 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, Sean 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 analyze numbers, but they use it towards other parts of life. And that's where it starts getting interesting, because they're sort of like 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 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 the balance sheet of life, just like a decaying asset. That's kind of interesting to me. It's funny, because one of the things that had an impact on me that was like, I was in an argument with a friend on the 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 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, 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 to them. 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? I was very, very afraid of wasting my life. Very, very afraid. A lot of people, 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, fuck 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 fucking 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 this was difficult, whatever. And I always tell them, 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 don'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 it's hard. If I don't know a person, I'm not going to be calling them chicken shit to their faces. But my friends who get the straight dope, I'm like, you're just a pussy. You're just a straight pussy. And they know it. They know they are. 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 a reason why people 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. Is there more to it than 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? 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? 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 the standard actually look like? Because it's easy to say that, but I'm sure you're a human. You get soft. Of course. Yeah. Of course. So 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 ego and not saying I'm sorry. Like I don't want to look wrong, you know? 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'm being soft about this situation. I've had a lot of training and not giving a fuck what other people think, both in compliments and derision. 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? How do you live this life but being kind and loving to the people you care about? It's very important to be kind. I'm a big supporter of people. I want people to win, give them my time and show up for them. But my time is extremely valuable. I don't know. Usually my wife is 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 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. And I'm kind of over here, like one shade in the autist. Like I give people the straight dope and I don't pull punches. I don't think I'll 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. And so like, but you got friends that are just like, oh, I'm not going to say anything while you're sitting there talking with a booger out of your nose. 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. Exactly. 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 know, 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, you know? 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? 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, we're really just programming, right? I don't eat fried crickets because I didn't grow up in Asia. You know, 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, right? And so almost all the things that I like were 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 was going to erase 20-something years of programming in a day, right? But give us a couple of the bullet points. What did you, 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, I show up with kindness. Like you're in Jersey City, right? If you go in 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 and it crowded. So you said, okay, so rule number one, I'm not going to be reactive. I'm going to, I'm not going to be a hype. Yeah. Well, I'm reactive, but what are my response cries to certain stimulus, right? Like there's, 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. You, what did you say? How did you react? You know? And, you know, people write tons of books on this stuff, like, you know, controlling yourself or whatever. But ultimately is like, you have lots of stimuli and lots of responses and which ones work for you and which ones don't. And 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. you'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 were like, what was, you know, 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, you were, okay. Maybe you were the guy who told me. 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 for 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 where, 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 on 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 like 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 to like 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. Like I wanted a more of a boring life. And I actually think a lot of like 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 or were you trying to be fulfilled? Yeah, just trying to balance it. I mean, I have 11 month 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 party and 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 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? Because 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. 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, we're 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. Well, the Breeze Assistant from HubSpot can help. It works right inside HubSpot. You can draft a campaign copy, blog posts, emails, all in your brand voice, all using your actual customer data. So you don't create just content, you create content that converts. Check out HubSpot.com, the agentic customer platform for growing businesses. 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 like the movie, a month before I'm gonna die, I'm gonna run around, do all these things, I'm gonna be happy, right? My life is complete. And the main thing is that each period of your life, like you don't have one death, you have many deaths, right? There was the college year that died, there was the single year that died, there was you with young kids that died, 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 wanna go skiing in my life 500 times, well, the distribution of those ski trips are probably gonna come earlier, right? And if it's skiing with friends, it's probably earlier, 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 fucked it up, right? Like, cause you're really not gonna get those 500 ski trips, right? 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 do I want out of 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 gonna 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, okay, what experiences, what choices do I wanna make in this period, or in this period, in this period? And when you do that, you'll 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 fucking up the order and not getting it at all. Do you do any type of annual planning? Yeah, we do like kind of a period, time bucketing period, like this is what we wanna do, like we know while Kai is under five, we definitely wanna go live in a different country, particularly Japan, and we're like, okay, how long is that gonna be? Is it just gonna be a summer, is it gonna be a year, is it gonna be two years? We're actively discussing how that fits, what's going on, and then all the other things, 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, here, like, because we talked with Jesse Itzler, and I think Sean does this now, where he like, do you do this, Sean? Were you like Jesse, where he like 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, 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, right? 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. Like I got married four years ago, or was it four, yeah, 24 years ago. And you know, 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? But that's just all bullshit. So like, I'm just being lazy and not doing things. 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, I did like, I just had a kid too, and I was peak. Now I'm a little less than peak. But it's like, for some reason I, in this phase, I'm like, I'll be a little less than peak. I accept it. I would say it's actually pretty horrible because you're using the U.S. averages, and the U.S. averages have like a 40% obese rate. So I actually think it's pretty bad. No, but I mean, looking at you now, I think you said you're 57. I could be like, 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 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 surf is one of mine, right? 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 fucking future bill over. And I don't want to fuck future bill over that much. And 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 fucking over future bill right now. Well, this is actually interesting because most people are probably fucking 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. Cause 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 fuck over future bill. You wrote the book and the book has an amazing title. Like one of the best book titles ever. And I've studied this. It's almost too good. You don't even need to read it. Yeah, exactly. You can give somebody the book cover and they can, they should judge it by its cover. So the book is called Die With Zero. What was the original title going to be? And how did you, what would you wake up one day and have that? Did you hire somebody to come up with that line? Like where did that come from? No, we were, it was just like, we came up with like 10 or 20 titles. What is this book going to be? Die with nothing, maximize your life. Kind of like descriptions of the book. And the ultimate concept is that you use all your resources here on this vacation on planet Earth. You leave it all on the field, right? So you die 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 leave everything, that if you do your best and you leave everything on the field, you have zero regrets. Like most of, 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, you know, what I'm accountable for. And then the publishers loved this. Like, you know, there was a little bit worried about like, well, people getting on airport, riding to an airport, you know, and it's like, die, you know? Like, that's gonna be hard sale in an airport. But it was like, it just hit. And so it was like, 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. to 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 were having a conversation. They're like, look, when we die, here's what we wanna 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 wanna 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. It's kinda like, vacation homes are definitely a hack for 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. But, and it's changed everything for us. Yeah, now, because I had this conversation with you, they're gonna have a more fulfilling life, and they're not gonna be like 85 on their deathbed going like, why didn't I do this? I didn't get as much time with so-and-so during this time period, et cetera. You've completely eliminated that future regret. And it still exists, by the way. There's still fear. Particularly if you're retired, you're like, will I have enough to take care of myself? That still exists, but I do think 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 gotta 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, like 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 the older cohort that have discretionary income or they plan on leaving something behind, they somehow change their estate planning and they're actually taking estate planning seriously. Oh, when I die, whatever's left over is gonna go to this person, this person, this person. The second one is like, we've completely, 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. So like I've made my parents retire and their sole job is to hang out with their grandparents. Like that, like that's it. Like your job is now to hang out with the grand, I'm sorry, with the grandchildren 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 I just kind of woke up to what I wanted and then they're now doing that. What about people who don't have money? Have you had, what are some interesting examples of people who you learn, who have read your book who are just, who are retired teachers or are teachers? Not wealthy people. Oh, they have money. There's 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 gonna get X per month, like they started going to live life. The other people that have money is like they're making different decisions, 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? 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 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're working somewhere and you're 20, so you didn't have a ton of money at the time and 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 gonna get six weeks off? He's like, we're not, we're gonna quit and we're gonna 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. Yeah. And you're like, as soon as he got back, I could see the glow in this mother's face and I knew I did it wrong. Like he had made the correct decision. And he got, his job was waiting for him. We were pee on, so I mean, like, what were we doing? What did we have to lose? And then you said, you finally went in your 30s 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. Backpacking, 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 like fun to sleep on someone's couch and like 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 rite of 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. Not, I would like, it was too grimy. I don't wanna do that shit. It wouldn't even be- I'm so envious of his story. I'm like so fucking 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. I don't, if you offer that, I could go do that now. I don't wanna 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. 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, you don't want to. I don't want to. Yeah. 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 using your resources, 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, to the day I die, I'm not gonna 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? 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. I go to school, whatever, I do whatever. 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 wanna be a farmer. So that doesn't cost that much, right? No, so my farming years are really, I know I'm gonna 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 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. So I got rid of it. Yeah, not in that time bucket, yeah. But walk me through this vision. What are you gonna do? You're talking about later in life? Yeah, I just really wanna- Yeah, what's this farm vision? I mean, I just wanna have 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. No, I 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 gonna be cool. They were like, sick yard. No, no, no. I want like basically a large garden. Some big gardener, some bees, you know? I had bees. Yeah, you had the bees, you had the whole thing, right? Like- 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 kinda enjoying grandchildren and friends and visiting and like, you know, when you're younger, you're seeking adventure, 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, right? 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's on the decline, you know, lung capacity's on the decline. You know, the things that I will do because they, you know, it's difficult to walk four miles or it's difficult to whatever. My world is going to shrink and I'm gonna be looking for friends to tell stories. And I wanna have a bunch of stories to retire, you know, retire my memories and do the simple things, enjoy the simple pleasures of life. So a lot of times people at the podcast will 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 three 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 this 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 three million in revenue and you just wanna 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 do like, 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 like 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 wanted, I never want to go to an office again. 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-size 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 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, when I talk to people about offices or going with it, when we deconstruct it, it's like, well, I like the people, and I like spending time with people, and I like 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, you do it. 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, 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 gotta get an office. 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 would agree with that. 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 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 say, 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 your first generation of masters, African-American masters, and the narratives that they would paint about, born in 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 was like a party house about black joy in the South during segregation, which is a uniquely American theme, right, like you can still leave an 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 gonna get that narrative, it's like jazz is the only original American art form. This painting is very, very unique culturally by the first or second generation masters. And it was featured on Marvin Gaye's album that won a Grammy, and it was on the opening or 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 was very culturally relevant, very historically significant, a narrative that's not gonna be painted in China or anywhere else, et cetera. So it was 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 Arnold messaged me, sent me an email, he goes, hey, isn't this the painting you've been looking for? Like I'd 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, shouldn't struggle an 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. It wasn't about that, right? 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, 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 gonna telephone auction this thing because what if the telephone goes down? Like I had all this nervousness, I'm gonna fly. And it was the first live auction I've ever been to and I flowed to Sotheby's and I stole that painting. 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. It was like, it was in the hundreds of thousand top million, right? Like a millions. And I was just like, people were like, why the is this in the evening auction? But so I knew there were some players who wanted to get this thing, but I figured like, okay, I'll just bid up 3 million, take it, scare everybody off and walk out the building with this painting. And it just like, was chaos. Like seven, like everything was pretty standard. Like, you know, whatever it was. Andy Warhol, Penn, 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. So then you can hear me yelling out 2 million and then it just goes crazy until we get to like around 7 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. You know, the funny thing is the guy who was bidding against me was like two seats ahead of me, 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? Like, who was he? I don't know. He was a 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, is that during the middle of bidding, which bidders don't talk, you don't talk to each other, whatever. He turns around to me and goes, I'm not going to stop. And then I said to him, well, then I'm going to make you pay. And then people kind of like chuckled who heard all that, laughed, and then it kept going. And 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 buy, 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 max 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. 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. And I was just like, I gotta go. 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, the role of the collector is to signal to future generations what is worth preserving. So what you see in museums, et cetera, where 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 should 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 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 period, that kind of like social stigma of 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 I arbitrage 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, yeah. And he was telling the 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, he's supposed to be this like guy's guy. Yeah, he writes this bad-ass 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 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 is all about the boxing and Clever Lang or whatever. And he became an action star, but like, he's an artist. Like people are multifaceted. So, 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 increase the value of the art, right? So, it's like, 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 artist has their A work, their B work, their C work, their D work and 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 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 2 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 and it wasn't me, it's just the market became aware, right? Like, when people like, well, why did you pay this much and why is this significant? I had like three 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. Yeah, I would have held up my arms when the guy turned around and said, I'm not gonna 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? Like, I would have already been celebrating the victory of having the cool one-liner ready to lock, stock and barrel, right? Then not like 10 minutes later thinking of what I should have said. No, I don't know, it just flowed. Some people it's like, I gotta have this car or I made it with this, this was the thing, you know? And I'd become a peon, minor art collector 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, 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. loan and then it's on it's on loan it's on a lot of loans like people borrow it it's on tour. How does that work so they're paying you to be able to exhibit it? No they don't pay they take they pay the insurance and they carry it etc. When I first got it my kids were like don't you dare bring that to the house you can't have 15 million dollars hanging on the wall we're gonna get robbed and so they're like they were all scared like somebody you know people know who you are and they're gonna come come take the painting so it uh so it's it's on tour right now. Man thank you so much for coming on I you know I don't know if you notice we've been trading dms back and forth like four years now trying to get you on uh you know we uh we have all types of amazing people come on I think that you're um and not 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 uh you really have some parts of your life that we really really really admire and um you know we ask ourselves like uh like this this flavor of advice what would they advise that we do in this period of our life and so you're definitely uh 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 like and I 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 you being in the paper I always tell people and I reserve the right to get naked at a party it's kind of my line um and 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. But you're kind of gotten famous you're you're 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 gonna date a bunch of people I'm gonna 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 in fame was like this is great marketing like you can get a lot of girls you know uh 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 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 gonna 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 type 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'm 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 gonna write another one? My wife says hell no uh it takes a lot of time but I actually um I'm being I'm it is seductive um you guys know Tim Urban? Of course. And so like he's like we should write a book together we like 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 we I've been like yeah I just need to kill a couple 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 like she's helping me be accountable to have the most fulfilling life but like if I I do I do this is seductive to me. What what topic? Don't know yet we've been thinking about a couple. What what's what's what's what are you obsessed with? Well there was there's a lot of things on like um relationships and purpose you know the one thing about the book I don't tell people is like whether whether their values you know like you you choose your values right and what what is fulfilling and and and so I have a couple 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 uh and purpose comes in design and there's a lot of design cues from your your biology that tell you your purpose the same design cues and a pair of scissors that tell you it's for cutting right and so I think um I have some theories about that I won't go into the long story about it there's a there's a couple things uh relationships but 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 hand books which I actually think I think those are cool uh like uh I know that um 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 handbook stuff dude it was great you buy it though nobody does them you can give it to him nobody's gonna fill it in yeah it's it's it's tough I left it for other people to write the computer programs to write the handbooks to the to actually do the math you know to 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 I mean that type of thing you know okay like I 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 yeah I mean I was the guy I just want to be the guy well Jesus got uh nailed to a cross my friend like yeah 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 uh named Austin who he 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 the but my book and he's like hey can I do a die with zero podcast I'm like have at it have fun I as well what 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 could be what I want to I put my all in it like no days off on the road less 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 in each episode you're going to hear from top entrepreneurs and creators and you're going to hear them share their secrets and strategies to turn their content into profit so you can check out content is profit wherever you get your podcasts