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My First MillionMy First Million

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

*Free guide: how to build wealth (and use it well):* https://clickhubspot.com/ac8r Episode 878: Shaan Puri ( https://x.com/ShaanVP ) and Sam Parr ( https://x.com/theSamParr ) talk to Bill Perkins ( https://x.com/bp22 ) about how to die with zero and never have a regret about it. — Show Notes: (0:00) Intro (0:55) How Bill made his money (1:55) Price go up or price go down? (3:45) Maximize risk when young (5:15) The 3 edges of the greatest investors (9:15) The name of the game is to stay in the game (10:25) A decade of intensity (12:20) No parties at 85 (13:00) Define your net worth peak (18:15) Shaan reads an email to Bill (19:25) The fear of a wasted life (20:00) Crush your ego (25:45) Set your cookie cutter life on fire (26:10) Reprogramming your brain (30:00) Rewrite for maximum accountability (32:55) Seasons of balance (34:25) Time buckets vs. bucket list (37:15) Plan your year (38:30) What Bill regrets right now (41:05) Don't fuck your future self (42:15) Die With Zero (52:35) Playing the money game for fun (54:05) What Bill spends his money on (1:00:35) Spending $15M on a painting (1:09:05) The art of Sylvester Stallone (1:17:05) Bill's follow-up book — Links: • Die With Zero - https://diewithzerobook.com/ — Check Out Sam's Stuff: • Hampton (joinhampton.com): My community for founders. Average member does $25m/year. Many of the guests are members. Get after it...apply: http://joinhampton.com/mfm — Check Out Shaan's Stuff: • Shaan's weekly email - https://www.shaanpuri.com • Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents. • Mercury - Shaan uses Mercury across all of his companies. you can too: http://mercury.com/ Mercury is a fintech company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., Members FDIC • I run all my newsletters on Beehiiv and you should too + we're giving away $10k to our favorite newsletter, check it out: beehiiv.com/mfm-challenge My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano /

Bill PerkinsguestShaan PurihostSam Parrhost
Nov 2, 20261h 20mWatch on YouTube ↗

Summaries, chapters, transcripts, and FAQs on this page are made by uListen, not YouTube.

EVERY SPOKEN WORD

  1. 0:00 – 0:55

    Intro

    1. BP

      I kinda wanted to be like Jesus and just like, "Go forth and build the church. I'm out of here." Like, I, I, I don't wanna be the guy, you know? A lot of people write books to be the guy. I don't wanna be the guy. I wanna live my life.

    2. SP

      He's like, "I wanna be Jesus."

    3. BP

      [laughs]

    4. SP

      "But I don't wanna be the guy." [upbeat music] Well, Bill, on that note, welcome to the show. [laughs]

    5. BP

      Thanks. [laughs] Thanks.

    6. SP

      I don't know if you know what you're getting into.

    7. BP

      No, no.

    8. SP

      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, but the show got popular so we didn't change it since then.

    9. BP

      Right.

    10. SP

      And so people come because it, they think it's all about making money-

    11. BP

      Right

    12. SP

      ... and getting rich. And it kinda was at the beginning.

    13. BP

      Okay.

    14. SP

      And then as we got rich, we started to f- 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-

    15. BP

      Correct

    16. SP

      ... how I discovered you. And so we're gonna talk, I wanna talk a little bit about both, the making

  2. 0:55 – 1:55

    How Bill made his money

    1. SP

      of as well as the using, uh, of money. And so maybe we start with can you just explain how'd you make your money?

    2. BP

      I made my money i- the original pool of capital, uh, I made my money trading commodities. I traded, uh, natural gas derivatives. Started out as, like, a assistant assistant peon, as a clerk on the New York Mercantile Exchange floor. When the natural gas futures contract started, I want, 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, uh, deregulation hit, 19 or, 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.

    3. SP

      Sam, when he, w- when he says an- when he says energy... He's an energy trader, commodities, derivatives. What does that mean to you, Sam? Y- how much of that do you understand?

    4. SP

      Uh, yeah. Not much, frankly.

    5. SP

      [laughs]

    6. SP

      We, we, we create websites that,

  3. 1:55 – 3:45

    Price go up or price go down?

    1. SP

      like, people come, and they either buy something or we make money via ads.

    2. SP

      [laughs]

    3. SP

      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.

    4. BP

      Yeah. You're basically just betting on price go up, price go down, or vol go up, vol go down with spreads, et cetera.

    5. SP

      How did you get good at knowing if the prices go up or go down when everyone, every other smart guy is also trying to figure out if the price is gonna go up or down? How, how do you, how do you win that game?

    6. BP

      Well, you know, there's, there's... You know, we're really not in com- 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 a vet- fair value. And so that's kinda 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 gonna charge you X for this insurance product.

    7. SP

      Can you give, can you give, like, a, an even more dumbed-down example? So, like, for example, uh, a, a company needs to, uh, acquire a bunch of oil. Are you the middleman who would go and acquire it, and you would try to get, uh, a small profit?

    8. BP

      Yeah. Let's, let's say the, the winter's coming, and people are afraid price is gonna go up. And generally, I was always short, right? 'Cause people are always afraid price is gonna go up in the winter 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 fr- to, 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, most of the money I made was from being short natural gas over time.

    9. SP

      Being a trader like this, it's one of the few gigs where you can get pretty rich as an employee working for someone else.

    10. BP

      Yeah.

    11. SP

      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?

    12. BP

      Uh, yeah. I mean, it... Ha- had I been smart or smarter

  4. 3:45 – 5:15

    Maximize risk when young

    1. BP

      about it, I would've 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 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, you know what I mean, I don't wanna have all my money parked in the fund as well. Now, what, 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've been fully concentrated and, and just bet the farm because I was always gonna 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, a percentage of the money that you earn when, when you do well.

    2. SP

      And you were saying, you said, "Well, I initially made this, uh, this, this pool of capital, uh, by trading."

    3. BP

      Right.

    4. SP

      Were you sorta 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?

    5. BP

      I was, I was kinda 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, it, it's... I, I... The analogy I would use is somebody who buys and sells houses versus somebody who's a real estate agent. I hated being the real estate agent.

  5. 5:15 – 9:15

    The 3 edges of the greatest investors

    1. BP

      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.

    2. SP

      Now, we've had a couple of different types of investors on the podcast in, in the past. We've had, like, uh, the Howard Marks, Ray Dalio types. And I would say a lot of what they talk about, uh, uh, there's kind of three ways to win that I've, I've picked up. So one is superior temperament. So, you know, the kinda 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. Uh, you know, I'm buying a ETF, and I realize that the underlying 100 stocks underneath it are not priced exactly in, you know, in some 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?

    3. BP

      I would say we were one and two. We weren't the arbitrage. We were one and 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 d-drives supply and demand, right? And then what may happen, and then will 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 b- how bright you are, uh, you need to have that temperament, that stoic temperament, um, that ability to handle losses and, um, or, or be robotic about trading.

    4. SP

      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 Marks, 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 m- far more Texas cowboy. Like, when I read books about like H.L. Hunt, you know, one of the guys who, like, um, got oil going in Texas in the, um, mid, uh, 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?

    5. BP

      Uh, uh, 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, you can invest in my fund and you can lose 100%, but my fund can also return 300, right? So, like y- it's really the expected outcome and what kind- what are you trying to do here?

    6. SP

      Did you ever almost lose it all?

    7. BP

      Yes, couple times.

    8. SP

      Hey, uh, this is one of those episodes, so I don't wanna show you my notes, but just imagine this is full of notes because the other pages are. Uh, Shaan 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, uh, 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, what were the swings in numbers?

    9. BP

      Down 50%

  6. 9:15 – 10:25

    The name of the game is to stay in the game

    1. BP

      to plus 250.

    2. SP

      On how much money are we talking about?

    3. BP

      100 and something million, 200 million, you know. So 100 million to 250 million. Yeah, by, you know, in a year, and then we go through the winter, we build that up, we chop wood, and we go there. And that's why I like to, you know, we say, uh, 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 insur-insurance guys wrote these insurance policies against hurricanes, and then two hurricanes came, and they have a, a terrible year." Like some almost get wiped out, right? But then they keep writing insurance the next year. The insurance goes up.

    4. SP

      Right.

    5. BP

      And they just print money and print money. And so unless you're in the arbitrage game, uh, you will have a bad, you will have a very bad year.

    6. SP

      Shaan, this seems like your style a little bit. How, how-

    7. SP

      [laughs] I do enjoy-

    8. SP

      You know?

    9. SP

      ... 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

  7. 10:25 – 12:20

    A decade of intensity

    1. SP

      friends and a kinda 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.

    2. BP

      Yeah.

    3. SP

      Were, were you... Did you have a decade of your life where you had to be a bit of a maniac or no?

    4. BP

      Yeah, you become obsessed with the puzzle, uh, and that obsession helps you to have informational and 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?

    5. SP

      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, build a company that's gonna sell a product"?

    6. BP

      No, knowing what I know, I would've went, I would've went into equities. It's just much bigger, and it- 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? [laughs] Or not that exciting track records, and you get positive drift on your side from the stock market. And so-

    7. SP

      Does the skill set translate? So equities meaning you would, you would evaluate different companies and figure out w-which ones are bringing-

    8. BP

      Yeah

    9. SP

      ... and buy-

    10. BP

      I have a basket of stocks. There's just so much more capital available for people to invest in equities. It's kinda like n- 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, 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?" [laughs] You know what I mean? Like, it doesn't, right? So like your, your, your, your, your,

  8. 12:20 – 13:00

    No parties at 85

    1. BP

      your maintenance becomes a profit center, and then your, 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 have been much richer? I would've went into equities.

    2. SP

      Do you do that now with your personal money?

    3. BP

      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 e- w- 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.

  9. 13:00 – 18:15

    Define your net worth peak

    1. SP

      When you, um, were coming up, did you have like a number in mind, a goal, and then did, did you hit that number or did you just, just simply, like most people, move the goalpost and say, "No, no, that's not enough." Like, describe to me kind of your, uh, y- what your relationship was with the number.

    2. BP

      Yeah. The number was I just wanted to be a millionaire before I was 30. It was kind of the thing. Y- 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 the 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, right?

    3. SP

      Mm.

    4. BP

      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 wanna be a millionaire before X date," right? It's almost like a Miss America cookie cutter answer type thing that like-

    5. SP

      [laughs]

    6. BP

      ... people starting out do. They're not really thinking about it. It wasn't 'til 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?

    7. SP

      When you're talking about later in life, is that like in the last five years, or that was when you were 32?

    8. BP

      Pro- 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-

    9. SP

      Right

    10. BP

      ... and its ability to convert that money into, uh, fulfillment and useful experiences d- declines. Net rate of decline starts approaching affinity as you get close to your deathbed, and so d- like more money means nothing at, at, 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.

    11. SP

      What was that moment that, that changed that where you realized, uh, 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 gonna carve out this new path"?

    12. BP

      Yeah. It wasn't like I, you know, I was on my horse on the road to Damascus, and then I, I fell off it and got a vision. It was more like there were, there were many things. I read a book called Your Money or Your Life, which kinda introduced the concept that the best definition of money is something you exchange hours of your life for. And then that kinda 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, and why? You know, that, that, that started coming along. And then, you know, really thinking about death and when do certain things happen. Like you wanna 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 wanna do all the rockstar stuff, but it's not... You know what I mean? It's not at 55, right? And so like it's kinda like what experiences belong when, and what does the arc of my life look like? How does money fit into that? How does health effect, effect that? And so those thoughts were reinforced by different conversations, b- books I've read, et cetera, to come up with like 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 do these variables fit, you know? And so that was over a time period. It wasn't just like, "Oh, shit, is it, it, here it is. I have this formula," you know? Uh, E equals MC squared or, you know, [laughs] you know, that, that-

    13. SP

      Well, it's, it, it, it kind of is like that. It's sort of funny. Like the reason Shaan and I aren't particularly investors, but we 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, but they use it towards like other parts of life.

    14. BP

      Yeah.

    15. SP

      And that's where it starts getting interesting because they're sort of like very rational, whereas most people do things just 'cause that's how everyone else does it. And you start se- hearing these like 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 y- they kinda 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, [laughs] just like a decaying asset. That's kind of interesting to me.

    16. BP

      It's funny because, uh, th- you know, one of the things that had an impact on me that, that was like, uh, 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 wanna pick a fence in a white house or whatever and go get a job and work like that. I don't want that cookie cut- 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,

  10. 18:15 – 19:25

    Shaan reads an email to Bill

    1. BP

      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, to have the most fulfilling life?

    2. SP

      I wanna read you, uh, an email I sent to my sister and my mom that's from your book. It's a excerpt from your book that, that resonated so much that I h- hand typed it back out by hand to them.

    3. BP

      I like that. [laughs]

    4. SP

      I was like, "Y'all aren't gonna read this book, but I need you to read this." And so it says-

    5. BP

      Okay

    6. SP

      ... "Death wakes people up, and the closer it gets, the more awake we become. And when the end is near, we start, suddenly start thinking, 'What the hell am I doing? Why did I wait this long?'" Um, 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 there 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." And then you talk about a couple of the principles-

    7. BP

      Yeah

    8. SP

      ... to, you know, one, timing matters. Some experiences can only be enjoyed at certain times. You can't water ski when you're

  11. 19:25 – 20:00

    The fear of a wasted life

    1. SP

      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.

    2. BP

      That's like the why you write this book, why 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, or I fear losing all the, all, all, all I built, and I fear losing my status," whatever. And I'm just like, [censored] that shit. I fear wasting my life. The money is just a tool

  12. 20:00 – 25:45

    Crush your ego

    1. BP

      to get-

    2. SP

      But how do you, how do you balance, um, career ambition, ego, and living where you're gonna die soon and, and, and all that? I mean, that, that's, that's really hard.

    3. BP

      Yeah. I think if you really wanna be successful and, and do something different and live, live a, like a non-standard life, you really have to crush your [censored] ego constantly. There are some high ego people that somehow make it or whatever, uh, in a, in a narrow lane, but then I, I tend to think they suffer the other balancing points in having a real fulfilling life.

    4. SP

      Can, can you explain what you mean by crush your ego? Like, what does, what does that mean for you? When, when did you do that?

    5. BP

      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 pole 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 [censored] 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 aren't you, 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.

    6. SP

      [laughs]

    7. BP

      And, and, and you know, like it's hard... Like if I don't know a person, like I'm not gonna be like calling them chicken shit to their faces. But my friends who get the straight dope, I'm like, "You're just a [censored] 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, 'cause you expose their o- their own cowardice.

    8. SP

      Let's say you, you point out to a friend, you say, "Look man, I think you're just being, 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, that's what it is. Get over it. Hey, you need to just do it anyways?

    9. BP

      They still don't do it. I mean, a lot of them still don't do it.

    10. SP

      For the few that do, what works? What, what, what works to get them out of that state?

    11. BP

      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?

    12. SP

      But let, let, 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? Like, what does, 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, you, you get soft-

    13. BP

      Of course

    14. SP

      ... like everyone else. Yeah. So like-

    15. BP

      Of course. [laughs]

    16. SP

      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, I will. I, I committed to something that I shouldn't have committed to," whatever.

    17. BP

      I mean, I, it's, it's a constant conversation I have to have with myself about a lot of things. It could be in an interpersonal relationship on having ego and not saying I'm sorry. Like, I don't wanna f- I don't wanna look wrong, you know? I don't want, I don't wanna appear wrong. I don't wanna appear like I'm the person. It could be a like, I don't wanna look like an idiot. I don't wanna go get up and do this, or I, I, I, I, I'm being soft about this situation. I, you know, I've had a lot of training in not giving a [censored] what other people think, both in compliments and, and derision, and so it, it allows me the freedom to be me and, and try things that other people would be scared to do.

    18. SP

      How often do you get accused of being an asshole? Like, how do you f- how do you live this life but like, you know, being, uh, kind and, and loving to the people you care about?

    19. BP

      It's, it's very important to be kind. I'm, I'm a big supporter of people. Like, I, I want people to win, give them my time and, and show up for them, but my time is extremely valuable. I don't know. Uh, probably my wife is like, "You're being an asshole." It's probably like [laughs] a month, you know, it's like maybe a month ago or whatever. It's usually when it's just like a, an, a 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.

    20. SP

      That's a good line.

    21. BP

      And so I, I, I, I think- It comes across. And I'm also very... I'm like, you know, on the complete empath- em- an empath to a autist. You know, I'm kinda over here, like one shade in the autist. So like I, I, I give people the straight dope and, you know, I don't pull punches. I, I don't think you'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, 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. [laughs] You know what I mean?

    22. SP

      [laughs]

    23. BP

      And so like, but you got friends that are just like, "Ah, I'm not gonna say anything while you're sitting there talking with a booger out of your nose." Like, so like it, it's just, you know, that's how I show up.

    24. SP

      Like, I don't wanna embarrass you, so I'll let you embarrass yourself.

    25. BP

      Yeah, exactly.

    26. SP

      Uh [laughs]

    27. BP

      Like you, you... Exactly, that type of thing. And, and for whatever reason, you know? It doesn't mean they're being an asshole, whatever. It's just that's their programming, you know?

    28. SP

      Hey, so a, a minute ago you were talking about like, you know, you had a friend who was saying, "Look, I don't want that kinda cookie cutter life," and you realized that

  13. 25:45 – 26:10

    Set your cookie cutter life on fire

    1. SP

      you had been wanting this kind of cookie cutter life, this, uh, this vision that had been set for you, whether it's from the movies or your parents or whoever, right? I think every, every man goes through this where-

    2. BP

      Cultural osmosis, as I like to call it, you know?

    3. SP

      Yeah, exactly. Um, and, 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 r- you had to put some definition behind it, something that, that meant something to you. And even if others wouldn't want that, you really wanted it.

  14. 26:10 – 30:00

    Reprogramming your brain

    1. SP

      What, what did you come up with? What, what, what is the answer to that for you?

    2. BP

      I, 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, I r- I realized like, hey, what I wanted at the time, I was gonna 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, right? I don't eat fried crickets 'cause I didn't grow up in Asia, you know? If I grew up in China, I'd, I'd be like, "When can we get some fried crickets, man? Those 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, I realized that it was gonna take a lot, and it's not that all programming is bad. Like, some of them it's like I like it. Copy, paste, repeat. But a lot of the programming did not work for me and was at conflict at what I really wanted and, and it was gonna take some thinking and discovery, um, to, to actually come to what I, what kind of life I wanted, you know, what, what, what, what, h- how these, how do these conflict, what my values. Are my values the right values? Yada, yada, yada, and that was gonna happen over time. It wasn't something that was gonna happen, like, right away. I wasn't gonna erase 20-something years of programming [laughs] in a day, right? Or, or a month.

    3. SP

      But give us a couple of bullet points. What did you, what did, what were some of the principles or tenets that, that you did end up replacing that actually you do live by now, or you do chase now?

    4. BP

      Oh, there's a lot. I mean, the, the... how I react to people when they trespass against you. I, 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?

    5. SP

      [laughs]

    6. BP

      Like, that's a cultural programming. Like, I'm not gonna-

    7. SP

      What did you decide that you were gonna do?

    8. BP

      I'm not gonna be punching people in the face 'cause they stepped on my sneakers in a cr- crowded club.

    9. SP

      So you said, okay, so, uh, rule, rule number one, I'm not gonna be reactive. I'm gonna... I'm not gonna be a hothead.

    10. BP

      Yeah, like how, how... Well, I'm reactive, but what are my response cries to certain stimulus, right? Like there's, everybody has certain stimulus, like s- 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, 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 jud- You know what I mean? Like, it wasn't like a, a, 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, you, 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, 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 e- ultimately it's like you have lots of stimuli and lots of responses, and which ones work for you and which ones don't? And, and the ones that work, you know, you rip them out and replace them with something else.

    11. SP

      That's been, um... You know, people ask us, we've done almost 1,000 of these episodes, people like, "What, what are some of the commonalities of people who win?" And w- 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 wanna 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, uh, that we've noticed amongst successful people, but that attitude

  15. 30:00 – 32:55

    Rewrite for maximum accountability

    1. SP

      that you just described is, is one of the common ones.

    2. BP

      Yeah. Es- essentially, it's maximum accountability, right? It's just like you are ultimately accountable.

    3. SP

      Do, do you, do you know... You're a poker guy. Do you know Daniel Negreanu?

    4. BP

      Yes.

    5. SP

      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, a 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-"

    6. BP

      He went to Choice

    7. SP

      ... he says.

    8. BP

      Yeah. I went before him.

    9. SP

      Oh, you were-- Okay, maybe you were the guy who told him, 'cause he said-

    10. BP

      Yeah, he was like five, he was like five or six classes after me.

    11. SP

      He was like, "Someone I really respect had done it," and, and so, you know, I'd said, "All right, fine, I'll go do it." He talked about this maximum accountability principle where you had to write a story of your life of something that, 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 in- instead of in the victim mindset, but in, with 100% ownership of your part of that whole thing. And he goes, "It was the most freeing moment of my life." And I, and it really stood out to me. I think of a, I think a lot of people would benefit if they just rewrote one story in their life with, from the point of view of maximum accountability. Did you do that same exercise?

    12. BP

      Yeah. I've done that and many more [chuckles] on, in terms of accountability and, and not, not being in a victim mindset. And it's, it's, 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 y- y- you know, getting the maximum accountability, uh, aspect going is, is a constant practice, right? Like, you never get to perfection. You just, you constantly have to practice that.

    13. SP

      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 5:00 and not going out at night," and I don't particularly love traveling that, that much, 'cause I wanna be with my family. Like, I wanted a more of a, a, 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 kinda nice to work 40 hours a week and also have a family that you're with all the time versus partying and, and going out. How do you live this pretty dope life when you have young kids? I, I think your kids are, are, are more grown now, but what were you doing when your kids were, um, in school and trying to, like, live this life where you're trying to be fulfilled?

    14. BP

      Yeah, just trying to balance it. I mean, I have an 11-month-old now. My kids are 22 and 19, and they definitely wanna come... Like, I, my, I had a big party. My daughter's like, "Can I come? Can I come?" I'm like, "Yeah, you can come, but you, you can't, you can't stay." I was like, "Look, you guys have 6th Street and all the partying." I was like, "Why can't us adults hang out and get our swerve off? Like, why you gotta come?" But she wants to hang out. She's like, "Dad, you're cool. I wanna hang out now." Whereas before it 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. Uh, and you know, traveling, I take my kids traveling. We try and arrange the life. Like,

  16. 32:55 – 34:25

    Seasons of balance

    1. BP

      listen, there's something very seductive about a bucolic life, um, that I want later. You know, I ultimately wanna be a farmer. And, you know, I've thought about, how do I get everybody into the life that I wanna 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, 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, uh, 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, and enrolling other people in the vision and, and making sure it works. You know, there's people who are f- you know, military parents, and their, 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 a obligation to the United States government. They travel around with their kids, and they wanna live, you know, live somewhere. My wife and I, we're like, "Hey, we wanna live in Japan for a little bit, so we're gonna pack up our little boy and, 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, and, and, and trying it out. You know, I, I don't, um,

  17. 34:25 – 37:15

    Time buckets vs. bucket list

    1. BP

      you know, there's nothing wrong with people that just like, "Hey, I just want a 9:00 to 5:00. 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.

    2. SP

      Can you explain this idea of, uh, time buckets, not bucket lists?

    3. BP

      Yeah. The idea of, like, a lot of people think life is like, "Oh, uh, I have a bucket list," and, you know, like the movie, you know, "A month before I'm gonna die, I'm gonna run around, do all these things, and I'm gonna be happy," right? "My life is complete." And the, 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 the single you that died. There was you with young kids that died. You know, first job, first startup, et cetera, right? And, and, 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 and 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 the, if a satisfaction, 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, right? 'Cause 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 y- th- those activities get shifted later into your life, you, well, you've kind of [censored] it up, right? Like, 'cause you're really not gonna get those 500 ski trips, right? And so life is like Tetris. You kinda 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, a, 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 kinda like a time bucket of each period of your life, maybe three to five-year brackets and saying, "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 [beep] up the order and not getting it at all.

    4. SP

      Do you do any type of annual planning?

    5. BP

      Yeah, we, we, we do, we do, like, kind of a period, time bucketing period. Like, this is what we wanna do. Like, we know while Kai is, you know, 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?" You know,

  18. 37:15 – 38:30

    Plan your year

    1. BP

      we're actively discussing, like, how that fits, you know, what's going on. And, and then all the other things, you know, people have multi, uh, faceted, multi-varied experiment running their lives, right? Like, how do all these pieces fit in? And it's kind of fun doing that.

    2. SP

      Do you sit down with your wife and you're like, um, okay-

    3. BP

      Yeah

    4. SP

      ... here, like, 'cause we talked with, um, Jesse Itzler, and I think Shaan does this now, where he, like... Do you do this, Shaan, where you, like, like Jesse, where he, like, plans his, like-

    5. SP

      Yeah

    6. SP

      ... quarterly trips?

    7. SP

      I carve out three days now a year, 'cause 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, uh, I try to get creative and, 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, I try to make it happen then.

    8. BP

      Yeah, that's awesome. I mean, we sit down frequently, but our, our, our life and our travel schedule's so packed into so many... We're reacting to a lot of events, right? Like, we're in the, playing a game like catching events, [laughs] like, and, and trying to move them around. Can we go? But then the larger arc conversation, like, where do we wanna be and set up camp? What culture do we wanna discover? You know what I mean? What activities? Those are go- ongoing.

    9. SP

      But what, what, what part of your life are you most dissatisfied with right now? And I ask this because I think when people listen,

  19. 38:30 – 41:05

    What Bill regrets right now

    1. SP

      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 the matter they're still trying to shift around, whether it's their health or their relationships or whatever.

    2. BP

      I'd have to say, um, health adherence right now. Like, I got married four years ago. Four, was it four? Yeah, 20- four 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 'cause we have a small baby. I'm too tired to do the things. You know, just went through a pregnancy and just kinda ate like, you know, I was a, a prisoner on death row. You know what I mean? [laughs]

    3. SP

      [laughs]

    4. BP

      Like, but, uh, that's just all bullshit. So, like, I'm just being lazy and not doing the thing, so.

    5. SP

      [laughs]

    6. BP

      I've broken all the, all the, all the stay in top 1% health, and I'm, I'm, you know, down in the mids or below in certain areas.

    7. SP

      That's not too bad, though. I mean... And, and it's also, I did, like, I just had a kid too.

    8. BP

      Right.

    9. SP

      And, and I'm, I'm, I w- 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."

    10. BP

      I, I, 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. [laughs]

    11. SP

      No, but I mean, looking at you now, looking at you now-

    12. BP

      [laughs]

    13. SP

      ... I think you said you're 57. I could be like, y- you're, you're probably decently fit.

    14. SP

      [laughs]

    15. BP

      Yeah, I mean, but it, it depends on what you want out of life. Like, uh, you know, my doctor has a thing called the Centenarian Olympics, and it's kinda 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 sex 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? And they run the calculations on, like, here's your VO2 now, and here's the decline that you would have, like, for each climb where I'm at, and then the activities on one side are 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 kinda like how many watt hour, how many watt hours per kilogram of energy do I need to climb a flight of stairs to

  20. 41:05 – 42:15

    Don't fuck your future self

    1. BP

      do X activity, et cetera? And here it's basically VO2 max is kinda like the best indicator. And, and the things I, the things I wanna do in my last decade of life, like 80% of them I cannot do at this current trajectory. So you're saying not bad, like, now, but I'm kinda [beep] future Bill over, and I don't wanna [beep] future Bill over that much. And so you really have to think about the... Like, this whole book is like thinking about the total arc of your life and your total fulfillment and, and the net present value of that, and I'm completely [beep] over future Bill right now.

    2. SP

      Well, this is actually interesting, because most people are probably [beep] over their future self. You just said you're, you're, you're screwed it up. What are you gonna do to change?

    3. BP

      I've taken some of the capital and j- you know, we just hired another trainer that, that's here, that can work, you know, 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, 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

  21. 42:15 – 52:35

    Die With Zero

    1. BP

      in my power to make sure that I don't [beep] over future Bill.

    2. SP

      [laughs] You have a... You know, you wrote the book, and the book has an amazing title. Like, uh, one of the best book titles, uh, ever, and I've studied this stuff.

    3. SP

      Can I do the excitement?

    4. BP

      [laughs]

    5. SP

      It's almost too good. You don't even need to read it. [laughs]

    6. SP

      Yeah, exactly. [laughs] You can give somebody the, 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 gonna be, and how did you... What, would you wake up one day and have that? Did you, did you hire somebody to come up with that line? Like, where, where did that come from?

    7. BP

      No, we, we w- it was just like we came up with like 10 or 20 titles, like what is this book gonna be, you know? Die With Nothing, Maximize Your Life, like kinda like descriptions of the book. And the, 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, y- you know, and, and people are, 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... 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?" And 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 a fa- or, you know, 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 asp- you know, what I'm accountable for. And then the, the publishers loved this like, you know, they were a little, there was a little bit w- worry about like well people getting on airport, d- riding through an airport, you know, and it's there, it's like die.

    8. SP

      Die. [laughs]

    9. BP

      You know? [laughs] You know, like that's gonna be hard sell in an airport. But it was like it just hit and so it was like it was provocative and we went with it.

    10. SP

      I've used your book, um, 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, um, "Here's the dates that we are going. Everyone's welcome. Come, come and do vacation with us." Uh, like to our, to like my parents or my in-laws.

    11. BP

      Right.

    12. SP

      And it's pretty awesome. It's made vacations so fun. And then the second thing is I have, um, in-laws who ch- 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 o- 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, um, 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 v- 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, let... Pay for all of us. We'll go, we'll go with you." And, um, they're starting to do it, and it's made life so much more fun. And so they actually got a, a new vacation house that like, like it's kinda like va- 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, uh-

    13. BP

      Yeah

    14. SP

      ... about that. But it's, and it's changed everything for us.

    15. BP

      Yeah, like you, you... They're... Now because they 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?" 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.

    16. SP

      And it still exists by the way. Like y- 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, that still exists. But I do think like having a large dose of enjoy it now is good.

    17. BP

      Yeah. I mean y- y- y- what fear should be greater? Having a little bit of money-

    18. SP

      [laughs]

    19. BP

      ... and, you know, eating beans or wasting your entire life and missing out on your own life, you know? So I, I think, you know, for me it's, it's, it's, it's the latter.

    20. SP

      You must get stories like this all the time. Somebody reads the book and they make a change and, uh, th- you know, 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 a th- like kind of like what Sam's saying, you know, a, a, a change, a decision?

    21. BP

      What comes to mind is a lot of like the inheritance one because everybody's kinda like that just... It, it makes no [censored] sense, it's so obvious, and then they read it in the book, you're like, "You're right, this is so [censored] 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, [laughs] et cetera. So that's like most of like the older cohort like that, 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 gonna go to this person, this person, this person." The second one is this like we've completely... You know, people shifted retirement dates, they've completely rethought what they should be doing in the time bucket they, they, they're, 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- with, w- 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, I just kinda woke up to what I wanted and then they, they're now doing that.

    22. SP

      What about people who, who don't have money? Have you had... What are some interesting examples of people who you lear- uh, who, who have read your book who are just, who are retired teachers or are teachers, you know? Um, n- not wealthy people.

    23. BP

      Oh, they, they, they have money. Um, there's somebody in the military who reached out and it's like, "Yeah, it doesn't make sense. I have a guaranteed pension till I die. Why am I saving up all this [censored] money?" [laughs] Like they have no risk, right? Like their, their... A military pension, right? [laughs] 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, per month? Like they, they started going live life. Uh, the other people that want money is like they're making different decisions, right? 'Cause really it's about how do you allocate your time? Right? It's really about choices. Right? Money is just one of the to- uh, 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, 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 a... Some of them was like, "Eh, 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, there's, there's things like that. So people look at the three variables, and they look at kinda 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 spend- you know, 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 who, a- amongst those three tools, their wealth, their health, and their time.

    24. SP

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

    25. BP

      Yeah, yeah.

    26. SP

      You had a job.

    27. BP

      Yeah. It's my least favorite story. [laughs]

    28. SP

      [laughs] And he-

    29. BP

      But, you know

    30. SP

      ... you know, he goes, and you're, you're like, "Dude, I can't just... We, we, you know, how are we gonna get six weeks off?" He's like, "We're not. [laughs] 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.

  22. 52:35 – 54:05

    Playing the money game for fun

    1. SP

      do it.

    2. BP

      Yeah, that's a, 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 could still do it, you just don't, you don't want to.

    3. SP

      I don't want to.

    4. BP

      Yeah.

    5. SP

      [laughs]

    6. SP

      So have you completely slayed the money monster? Like, do you, do you a- wake up and do, like, do you have businesses? Are you, like, investing? Are you trying to do deals still?

    7. BP

      No, I have businesses. I still work. It's not, it's not that you can't work or you can't enjoy solving the puzzle. Like, we get addicted to puzzles, and those t- puzzles become fun to us. It's just that, you know, using your resources dur- you know, I use the resource, right? Like, there's no amount of capital I can't convert into fulfillment for me.

    8. SP

      W- what, what do you do now for work?

    9. BP

      Um, so I have two startups. One's called Sky5, one's called SimMax. They're, one's a geospatial, uh, intelligence platform, kinda 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, um, 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, if I was, if I, if I was sitting here and I go, "You know, to the day I die, I'm not gonna spend the money I have," like I, I have no need for any other money, there's no additional fulfillment to the, to a marginal dollar, quit it all in a heartbeat. Right? Just stop.

    10. SP

      Yeah.

    11. BP

      Like, what are you doing? You know? But there is marginal utility for me. For some people who their concept of enough, they hit it. Like, hey, I just like playing checkers with my friends, I grow potatoes in my yard, I, you know, I go to school, whatever, you know, I do whatever. Like, for them,

  23. 54:05 – 1:00:35

    What Bill spends his money on

    1. BP

      it's a different decision, right? Like, it's like, no, I'm wasting my life.

    2. SP

      Well, what, what is it for you? 'Cause you said ultimately I wanna be a farmer, so that doesn't cost that much, right? Uh, what, what-

    3. BP

      No, so my farming years are really... You know, like 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, you know, there's a lot of other activities and things I would like to do. I really fell in love with yachting. Uh, they're very expensive. I do like fl- 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, I do think it's worth working for that. But it, at, at a certain time, I'm almost getting close to the age where it's not really worth working for it. It's n- 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, I could lose money, I could, I could make a bunch of money, et cetera.

    4. SP

      Dude, every, 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. [laughs]

    5. BP

      [laughs]

    6. SP

      I, uh, I, I-

    7. BP

      I, I-

    8. SP

      I did that once. I tried it. It wasn't for me. Not at that ti- not, not in that time bucket, so I got rid of it.

    9. BP

      Yeah, not in a time bucket. Yeah.

    10. SP

      But what, um, what's... Walk, walk me through this vision. What are you gonna do?

    11. BP

      Uh, you're talking about lat- later in life? Yeah, I just kinda wanna-

    12. SP

      Yeah, what's this farm vision?

    13. BP

      I mean, I just wanna have, like, a hobby, not, like, a big giant farm with a tractor, right?

    14. SP

      How many acres?

    15. BP

      Like, couple acres, some gardens. Maybe grow some tomatoes or whatever. You'd be surprised.

    16. SP

      That's a garden.

    17. BP

      It's, like, a large, it's a large, it's a large garden. A large garden. It's probably a, a-

    18. SP

      You, you live in Texas. Ranches are pretty big.

    19. BP

      No, I don't want, I don't want a big ranch.

    20. SP

      I, I had 20 acres. I had 20 acres, and the Texans called it a ranchette. Uh-

    21. BP

      Yeah, that's a ranchette. You need, like, 1,000 acres to, like-

    22. SP

      [laughs]

    23. BP

      ... feel like I got a ranch, you know?

    24. SP

      Yeah, I thought I was gonna be cool, and they were like, "Sick yard." Uh, so-

    25. BP

      No, no, no. I, I want, like, basically a large garden. A big, big gardener, some bees, you know? Just-

    26. SP

      I had bees.

    27. BP

      Yeah, you had the bees. You had the whole thing, right? Like-

    28. SP

      Yeah, I had bees. I had honey. It was great. H- bee- beekeeping is probably the only ranch adjacent activity that is not a lot of work and is worth it.

    29. BP

      Yeah. And I, I love the pollinators, so that would be great. Um, you know, just kinda enjoying grandchildren and friends and visiting and, like... You know, y- y- 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, you know, 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, on the decline. You know, lung capacity's on 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. The, my world is going to shrink, uh, and I'm gonna be looking for friends to tell stories, and I wanna have a bunch of stories to retire, you know, retire in my memories and do the simple things, enjoy the simple pleasures of life.

    30. SP

      When was the last time you worked from an office, and has that impacted your life?

  24. 1:00:35 – 1:09:05

    Spending $15M on a painting

    1. BP

      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.

    2. SP

      Shaan, did you see this story about, um, this painting that he just bought? It was, it was... They, they did a good job of... I, I think it was on The Wall Street Journal covered this painting, Bill, that you got. Uh, I think it was called Sugar Shack. Have you seen this, Shaan?

    3. SP

      I saw this a long time ago. It was a, a YouTube video, right? You, you spent some ungodly amount of money on this painting.

    4. BP

      Yeah.

    5. SP

      What's the story?

    6. BP

      I mean, it's a, it's a very unique piece in, in American art, uh, particularly because o- one, you know, you say like, "Well, who, who was the African American da Vinci or, or whatever?" And the answer is no one, because they were slaves. And so it wasn't till after slavery and the form- formation of families, and they started growing up where people could actually afford, uh, paintbrushes and have the time to actually paint. And so you kinda 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, it's like 1910, 1920s, and then the, the '40s. And so this artist was a football player. He was a, a artist in a 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 lay f- ice- ice rink or whatever, but it's uniquely American. And not, 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, right? It's like jazz is the o- the, the only original American art form. Like, this painting is very, very unique culturally by, like, the first or second generation masters, and it was featured on Marvin, Marvin Gaye's album that won a Grammy, and it was on the opening or, uh, outro of Good Times, which Norman Lear was, like, kinda the first producer to put stories of young Black families on TV back in the '70s. And so this is very culturally relevant, very historically significant, a narrative that's not gonna be painted in China or anywhere else, et cetera, so it's uniquely American. And, and I was in love with it. I had seen it since I was a kid, and any, uh, Black person in my age range knows about this painting, has seen this painting and other works by Barnes. Uh, and when it came up, John Arnold messaged me. He sent me an email, and he goes, "Hey, isn't this the painting you've been looking for?" Like, I, I'd been looking for it 'cause 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, um, album." And when the biggest music star of the time asks you for a painting and you're [laughs] a struggling artist, you do what he says. So he changed the painting and painted on, you know, Marvin Gaye's thing, and it's on, and it's on I think his album called After the Dance. But that wasn't what... It wasn't about that, right? So he went and made another copy of it, okay? He painted an- 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? [laughs] Like wouldn't, wouldn't respond. And then I s- uh, John called me. He 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 'cause what if the telephone goes down?" Like, I had all this nervous energy. I'm gonna fly. And 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 lotta 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 $100 million.

    7. SP

      What did you pay? I, I don't know what you paid.

    8. BP

      Uh, the total price was 15 million.

    9. SP

      Describe the auction battle.

    10. BP

      It was, it was chaos because they did some chicanery. Um, so there's an evening auction and a, and a day auction, and, and the evening auction is particularly the more expensive works, right? But this, this had a estimate that did not fit the evening auction, right? Like, at an estimate of 250 to, uh... It, it was like it was in the hundreds of thousand, top million, right? Like, a millions. And I was just like w- you know, people were like, "What, why, why the [beep] is this in the evening auction?" But I... So I knew there were some players who, who wanted to get this thing, but I figured, like, "Okay, I'll just bid up three million, take it, scare everybody off, and walk out the building with this, with this painting." And it just, like, was chaos. Like, seven... Like, everything was pretty standard. Like, you know, you know, yeah, whatever it was. "Andy Warhol, Pinwood. Oh, yes. 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. "70. " Then you can hear me yelling out, "2 million," and then, "2 million, 3 million, 3 million, 4..." It, 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 are going back and forth on this painting. I'm going like-

    11. SP

      You could see them, right? You're, you're there live. They're there live. You know the person-

    12. BP

      The funny thing is the guy who was bidding against me was, like, two seats ahead of me. It was a empty row, and he was right there.

    13. SP

      [laughs]

    14. BP

      Uh, and it was just he and I going back and forth, and me pausing, and me thinking like, "What is going on here?" Like-

    15. SP

      Who was he?

    16. BP

      Uh, I don't know. He was a, he was a art consultant, a, a very respectable art consultant, uh, working for somebody who never revealed who the buyer was. The only, uh, thing that was odd, aside from me... You know, I ta- uh, is that during the middle of bidding, which, you know, bidders don't talk. You don't talk to each other, whatever. He, he turns around to me and he goes, "I'm not going to stop." And then I said to him, "Well, then, I'm going to make you pay." [laughs] And then, you know, people kinda like chuckled who heard all that-

    17. SP

      [laughs]

    18. BP

      ... laughed, and then it kept going. And at, you know, during the, 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."

    19. SP

      [laughs]

    20. BP

      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, I should buy... This is a really good painting. I should buy this." I was like, "Nope, you need to save your money just in case." Thank God-

    21. SP

      [laughs]

    22. BP

      ... because I was way over the amount I was willing to pay for this. Before the auction started-

    23. SP

      Going, going in-

    24. BP

      But I realized, you know

    25. SP

      ... what did you think your, what did you think your max was?

    26. BP

      I thought I was gonna pay, like, th- th- $3 to $5 million, you know?

    27. SP

      Wow.

    28. SP

      And it was, what, fif- you said 15?

    29. BP

      15 at the end.

    30. SP

      Did you-

  25. 1:09:05 – 1:17:05

    The art of Sylvester Stallone

    1. BP

      that I can actually own this painting that I used to watch on TV all the time. So it was, I was super happy.

    2. SP

      That's so awesome.

    3. BP

      I was super happy.

    4. SP

      It's, it's also awesome to, like... I think it's cool to be, like, this kinda, 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, uh, Sylvester Stallone? Apparently in the '80s he'd bought this, um, a, a Monet. I think it was called Haystacks. I think he bought it for, um, $110,000 in the 1980s. Years later he had some, um, bills to pay or something like that, and he sold it for 3 million. And then, like, 5 or 10 years later, that same painting sold for $130 million.

    5. BP

      Yeah. Yeah. It-

    6. SP

      Um, 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, why did I sell this?" And it was a really cool story to see. But, 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 clearly has an artistic side, and he spots a Monet b- before the world does. And it's just kinda cool to see, like, an eclectic human being.

    7. BP

      Oh, you should, um, you should watch the, uh... There's an interview with him about Rocky and the characters and him writing the characters. He is an artist. [laughs] He, he wrote that, and, and it's like, uh, when he talks about the development of the characters and what it's about, it, it's, it's a, it's an amazing thing. Like, the sequel's all about the boxing and Clubber Lang and whatever, but, like... And he, 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 certain facets of people's lives. But, like, everybody's a multi-cut diamond, uh, and, and some of those facets that you don't see are actually a bigger part of their lives.

    8. SP

      In a s- strange way, by having that bidding war, telling this story, getting the, buying it at the price you did, you increased 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, in a strange way.

    9. BP

      Yeah, I, I mean, I signaled to the market, uh, 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-

    10. SP

      Mm-hmm

    11. BP

      ... their D work, and, you know, et cetera. And so, um, 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've bought it for a couple hundred grand. It went for, like, 2 million to some, some Asian buyers or something like that.

    12. SP

      Mm-hmm.

    13. BP

      Right? And it, and this was the, the day auction, right? This is the, the cheaper stuff, right? And so I completely reset the Barnes market, you know. And, and it wasn't me, it's just the market became aware, right? Like, you know, when people are like, "Well, why did you pay this much, and why is this significant?" You know, I, I had, like, three, uh, you know, Artnet interviews and Wall Street Journal and interviews, and I, I, I went over the thesis, and everybody's like, "You're absolutely right."

    14. SP

      There's this photo of you, like, holding up your arms.

    15. BP

      Yeah, yeah.

    16. SP

      It's a, y- it's a great photo.

    17. BP

      Yeah.

    18. SP

      Dude, I would've 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?

    19. BP

      Yeah.

    20. SP

      Like, I, I would've already been celebrating the victory-

    21. BP

      [laughs]

    22. SP

      ... of having the cool sh- the cool one-liner ready-

    23. SP

      Yeah, yeah

    24. SP

      ... ready to lock, stock, and barrel, right?

    25. BP

      Yeah.

    26. SP

      And then not like 10 minutes later thinking of what I should've said.

    27. BP

      No, I don't know. It just, it just flowed, you know? It, it was-

    28. SP

      [laughs]

    29. BP

      It was a, it... You know, some people, it's like, "I gotta have this car," or, "I, I made it when this." This, this was the thing, you know? And I'd, I'd become a, a, a, a peon minor art collector thief of collecting Black works, and my friend John Arnold was helping me. He's a v- e- extremely astute collector. He saw it first, and he's like, "Would you..." I said, "What do you think?" He goes, "It's exquisite." And so, uh, and he's the one who notified me 'cause I was after it, and he, and, and kind of guided me on, like, collect, like, collect what you like, you know, collect A works, et cetera. And so anyway, yeah, it, it, it does help, but I don't expect to close the arbitrage gap in my lifetime. I'm just, you know, I get to show people and carry it and-

    30. SP

      Where's it now?

  26. 1:17:05 – 1:20:35

    Bill's follow-up book

    1. BP

      to have the most fulfilling life, and so that's why you never wanna be that famous.

    2. SP

      You gonna write another one?

    3. BP

      My wife says hell no. Uh, [laughs] it takes a lot of time, but I actually, um, I'm being sed- I'm, there, it is seductive. Um, do you guys know Tim Urban?

    4. SP

      Yeah.

    5. SP

      Of course.

    6. BP

      So, a- and so, like, he's like, "We should write a book together. We, like, we have a bunch of ideas. We'll write a book together."

    7. SP

      That's a crazy combo.

    8. BP

      And he just goes, "That would be fun." He goes, "Yeah." So we, we've, I, I've been like, "Yeah, I just need to kill a couple projects so I can have the time."

    9. SP

      What topic?

    10. BP

      Right now I have a no new projects thing from my wife, and she's right. Like, she's helping me be accountable to have the most fulfilling life. But, like, I, if I, I, I do, I do, this is seductive to me.

    11. SP

      What t- what topic?

    12. BP

      Don't know yet. We've been thinking about a couple.

    13. SP

      What, what's, what's, what's, what's, what are you obsessed with?

    14. BP

      Well, there was a, there's a lot of things on, like, um, relationships and purpose. You know, the, 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, I have a couple theories about purpose and fulfillment. Like, I think there's a lot of purpose porn 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 in 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. But there's a, there's a, there's a couple things. Uh, relationships. The, the, 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." [laughs] You know? I don't think I wanna do that, but, you know, I can mix in some of that.

    15. SP

      Well, a lot of the books now are having, like, handbooks, which I-

    16. BP

      Yeah, yeah

    17. SP

      ... I actually think, I think those are cool. Uh, I'd, 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.

    18. BP

      Yeah.

    19. SP

      Nobody does the handbook stuff.

    20. SP

      Dude, it was great. You buy it, though.

    21. SP

      Nobody, nobody does them.

    22. BP

      Yeah.

    23. SP

      You can put it in. You can give it to them. Nobody's gonna fill it in.

    24. BP

      Yeah, it's, it's, it's, it's tough. I, I've, I left it for other people to write the computer programs, to write the handbooks, to, 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 kinda wanted to be like Jesus and just, like, you know, "Go forth and build a church. I'm outta here." You know what I mean? That type of thing, you know? [laughs] Like, I, I, I don't wanna be the guy, you know? A lot of people write books to be the guy. I don't wanna be the guy. I wanna live my life.

    25. SP

      I wanna be Jesus, but I don't wanna be the guy. [laughs]

    26. BP

      I mean, I'm a-

    27. SP

      Jesus was the guy.

    28. BP

      I, I just wanna be the guy who wrote the-

    29. SP

      Yeah, well, Jesus got, uh, nailed to a cross, my friend. Like, you-

    30. BP

      Yeah, exactly

Episode duration: 1:20:35

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