Insights From History's Greatest Thinkers - David Senra

1. 0:00 – 0:35

   Intro

   1. DSDavid Senra0:00

      He's writing the book as a cautionary tale, right? And he says, "Listen, if I could do it all over again, I would still try to get rich, but I would've, instead of making, you know, hundreds of millions, maybe make $10 million or $20 million," whatever the case is. "But the most devastating part is, if I could do it all over again, I wouldn't have missed my kids growing up and I would've had fun." What is the point of living in a 30,000 square foot house owning a NBA team and you didn't even have fun? As he's trying to write this book, his co-author is interviewing his wife and she says the most devastating thing that, "If my family said this about me, I don't care if I have a billion dollars, I'm a failure." And she goes, "I miss him, but it's not like he was here when he was alive anyways." When you read a book like that, you get to the end and it's like, "I'm not going out like that."

   2. CWChris Williamson0:34

      (wind blowing)

2. 0:35 – 5:40

   The Mental Athleticism of E-Sports

   1. CWChris Williamson0:35

      I, last night, was with one of the first esports performance coaches. So, he is a mental performance coach that is employed by an esports organization to train their mental athletes, as they call them-

   2. DSDavid Senra0:50

      (laughs)

   3. CWChris Williamson0:50

      ... to maximize their performance.

   4. DSDavid Senra0:51

      Yeah.

   5. CWChris Williamson0:51

      And the stuff that they're- the stuff that they are doing with these kids is so cool. Taking across all of the stuff that we've seen from physical training now and importing it across into something which is actually, I think, the most mentally taxing sport that's- that- that exists-

   6. DSDavid Senra1:06

      Yeah.

   7. CWChris Williamson1:06

      ... because you can move your avatar on the screen significantly quicker than you can move your body, which means that you're basically overclocking your brain. Your brain was meant to move limited by the pace of your body moving when it comes to reaction times.

   8. DSDavid Senra1:20

      Yeah.

   9. CWChris Williamson1:20

      And what you're doing now is you've managed to overclock the physical world and you're now trying to catch up mentally. This guy was fa- uh, Thanksgiving dinner, nerded out with this guy for, like, two and a half hours. It was brilliant.

   10. DSDavid Senra1:31

       That industry is very fascinating. Do you know Blake Robbins by chance?

   11. CWChris Williamson1:34

       No.

   12. DSDavid Senra1:35

       Okay. Blake Robbins, he's a venture capitalist. He's over at, uh, Benchmark now, but he actually incubated 40 Thieves, that- that, uh, esports team and the brand and everything else. But his focus and why he's been, uh, invited to take part in one of maybe, you know, maybe the most prestigious or one of the most prestigious venture capital firms at a relatively young age, I think Blake's, like, late 20s, whatever the case is. He's obsessed with the edge of the internet and, um, he has this great line that has actually taught me a lot, that everything is a game. And his point is- is like if you look at g- uh, gaming as an industry, it's bigger than music, movies, and all- and a bunch of other things combined. Um, so I do think, like, it doesn't surprise me that they- they're at the cutting edge. Of course they're gonna have some kind of performance coaches. I think everybody does. Like, e- almost all the top performers have somebody that they actually want to bring in. In fact, I just re-read, um, so I've done, I've probably done, I don't know, 10 or 12 bi- uh, biography, uh, uh, ep- episodes on Steve Jobs. And then not only do I- do I reread, uh, like I read every single book I could find about him and then I would reread my favorite ones and then make episodes every new time, because the words on the page don't change, but, like, everything that you've learned since the last time you read it has changed, right? And then I would map out in the book, um, all of the people that he was inspired by, 'cause none of these ideas are new. And I- I wound up mapping it out and I did, like, a little bonus episode called- called, uh, Steve Jobs and His Heroes, and it just traces, I've done 39 episodes on Steve Jobs and the people he actually mentions, whether it's Da Vinci, Alexander Graham Bell, Edwin Land, the founders of HP, uh, all these people that, like, influenced the way he thinks about his work. And something Steve did on the second time he went to Apple, right? Uh, the time where he created all that value, c- um, 'cause if you think about it, he's kicked out of Apple, spends 13 years in the wilderness, right? From, like, age 30 to 43. Comes back and essentially the way you think about it is, like, Apple's in terminal decline. It's almost bankrupt, right? It's running out of money. They pay $500 million for NeXT, and you can think about it as, like, they paid half a billion dollars to rehire Steve Jobs and they got the deal of a fucking lifetime, right? Fast-forward, you know, now, what, uh, 20 years later, it's the most valuable company in the world. Worth, like, $2.4 trillion. But what he realized was it was very helpful and I actually heard a bunch of episodes you reference, me and you both share, uh, an admiration for Charlie Munger, he's like one of my personal heroes, and he says this. He's like, the role that he plays with Buffett, he's like, "It's very useful to have somebody else to organize your thoughts with professionally." Right? That's the role that he plays with Buffett. So, what Steve did is he hired this guy and he didn't have no official role inside of Apple. So he'd fly down, he lived in Seattle, he'd fly down to Cupertino on Sunday night. I think he would spend from Monday, Tuesday, and Wednesday all he would do is shadow Steve. He could not say, he had no authority inside of the company, he's just, he's with Sh- Steve a- all the time, and when they have a minute they'd have lunch together or they'd pull him to the side, they'd have one-on-one conversations. And it's that same thing. It's like, you might not call it a coach, but it's somebody that is not a part of your company, right? Doesn't technically work for you, but is very helpful to- to bounce ideas off of and to, like, organize your thoughts. So, whether you call it a coach, performance coach, you know, a friend, a confidant, I think that- that you see that idea over and over and over again.

   13. CWChris Williamson4:42

       There's that story about Marcus Aurelius, as he was walking through the streets of Rome, he would pay another guy as all of the- the small folk were throwing flowers at him and saying, "You're amazing. You're this sort of god-emperor. We're so glad that you're here." And the- the empire was flourishing. And there's this guy walking behind him just whispering in his ear, "You are only a man. You are only a man."

   14. DSDavid Senra5:01

       Yeah.

   15. CWChris Williamson5:01

       So, you could imagine if you were able to bring somebody back down to Earth like that but also have that as a confidant, someone that you can bounce ideas off, just how powerful that would be. I've noticed since moving from, um, having a business partner in my last company to now-

   16. DSDavid Senra5:13

       Mm-hmm.

   17. CWChris Williamson5:13

       ... doing the podcast where it's me at the sort of top of the tree doing it on my own, I do miss being able to speak to someone and just go, "Dude, I've got this- I've got this idea. Am I being a dickhead? Like, is this- is this a good idea?" And you go, "Yeah, of course it is." "Yeah, I- I knew it was. Thank you. I knew it was. I knew it was a good idea."

   18. DSDavid Senra5:28

       Mm-hmm.

   19. CWChris Williamson5:28

       I just needed someone to externalize, like, to just blow off all of that extra kind of mental, uh, energy and just cut- cut through the noise. Um, one of the guys that I've

3. 5:40 – 11:40

   Studying How Paul Graham Thinks

   1. CWChris Williamson5:40

      heard you talk about a good bit, and I keep on hearing about him from people that I respect a lot but I don't know much about him-

   2. DSDavid Senra5:45

      Yeah.

   3. CWChris Williamson5:45

      ... is Paul Graham.

   4. DSDavid Senra5:46

      Yeah.

   5. CWChris Williamson5:47

      What do I need to know about Paul Graham?

   6. DSDavid Senra5:49

      So, Paul Graham's a- I just spent the last, like, three weeks inside of his mind, because he's got, you can read all of his essays online for free at paulgraham.com. And he's been writing for, you know, over two decades. In fact-... a... I was talking to a friend of mine, um, my friend Patrick, who runs the Invest Like Best podcast. Um, and we were talking about that 'cause, you know, every single, as far as like influential writing for technology startup founders, it's like Paul Graham's essays, and I'm talking about the last like, you know, 15, 20 years, it's like Paul Graham's essays, uh, Jeff Bezos', uh, shareholder letters, which are absolutely fantastic, I've read, you know, multiple times, and then Peter Thiel's book, Zero to One. And so, I read, I spent the last three weeks, I read, I did three separate episodes on Paul Graham's essays and I was like, "You know what? I'm gonna re-read Zero to One." I think this is the third time I read it. But in the view of how does this relate to what Paul Graham, like how he thinks? Um, and the thing that I think relates to what you and I do is, he has this idea i- i- in fact the collection of his essays is, you can buy the book, it's called Hackers and Painters. And he's like at the very top levels, it's, you, there's no like painting by numbers, right? A lot of the best things, um, are, I hate to use this word art, because that's not the way I think about when I make a podcast, I think of like it's a craft, and it's like I'm actually making something. But it's, it's not science, and it't not art. There is like a, a, a form of taste to it, right? Um, and so he's like, the best painters are that way, the best computer software, like, uh, the best programmers are that way, 'cause he's a programmer. Um, he says, like, the best musicians are that way. I think podcasts are the exact same thing, where there's this great, I just, I watched your, uh, your appearance on Joe Rogan Experience, which was f- which was fantastic by the way, you did a good job.

   7. CWChris Williamson7:24

      Thank you.

   8. DSDavid Senra7:25

      And it was fascinating because, um, Spotify, before they tried to do that deal with Rogan, this came out, the person, the, the, I forgot her name, but the, the woman that was in charge of this is like, "Well, is there a way for us to say, like can we replace Joe? There's nobody who has an audience his size, right? Uh, but can we replace him with like maybe five that are similar and like we'll kind of package it up and it like replaces them?" And so they ran this test and like, no, we have to back up the truck and like there's only one Joe Rogan. And so if you would even ask Joe, like, "Why is your podcast so popular," right? Or like he's, it's, he's gonna have a hard way describing 'cause he's like, "I'm just being me. I'm following my natural interests." And one thing that I always say, and this relates to the program too, is like the most interesting people are the most interested, right? So like o- like I'm obsessed, my four interests happen to be entrepreneurship, reading, history and podcasts, right? And some people are always like, "Hey, what are your favorite podcasts?" And they're surprised by one of my favorite podcasts is this podcast called MeatEater and there's this guy named Steve Rinella, right? It is an outdoor hunting podcast. I don't hunt. I have nothing against it, like maybe I will one day, right? But the point was is like I've read all of Steve's books. He is deeply interested, he has dedicated his entire life to the outdoors and conservation and, and the, his way of life. And his l- his, his level of detail that he's able to talk about and the passion is just infectious. So it's like I'm not even into what you're into, but I just find the fact that you're so into it interesting, so now I'm interested.

   9. CWChris Williamson8:46

      Dude, my, my housemate, Zack, is the most infectious person when it comes to energy. So you know the, uh, m- is it motocross? What's the thing that Colin McRae used to do? Rally cross. Um, where these guys are flying down dirt tracks at 100 miles an hour-

   10. DSDavid Senra9:02

       Yeah.

   11. CWChris Williamson9:02

       ... and they've got the co-pilot with them, and there's people that go out to take photos and then they'll usually have a little bit of a crew with them and there'll be these special spots along the track-

   12. DSDavid Senra9:11

       Mm-hmm.

   13. CWChris Williamson9:11

       ... presumably ones that are maybe a little bit more safe, th- not at the corner of bends on the outside of them and stuff like that.

   14. DSDavid Senra9:17

       Yeah. (laughs)

   15. CWChris Williamson9:17

       And these guys will have gone, it'll be the middle of the night, it'll be pissing cold, it'll be raining-

   16. DSDavid Senra9:23

       Mm-hmm.

   17. CWChris Williamson9:23

       ... and they'll stand there to see (imitates car noise) and these dudes just are like, "Whoa!" And they'll look at each other, they'll lose their shit.

   18. DSDavid Senra9:32

       Yeah.

   19. CWChris Williamson9:32

       And Zack likes to watch that to gas him up before a training session, like he just gets so infected-

   20. DSDavid Senra9:37

       Yep.

   21. CWChris Williamson9:37

       ... by other people loving their shit.

   22. DSDavid Senra9:40

       Yes.

   23. CWChris Williamson9:40

       And, uh, this guy, the esports guy last night, same thing, fucking loves his, loves his shit. Couldn't tell me anything about like Valorant or fucking Rocket League or League of Legends or any of this stuff, but he loves his craft. And that gassed me up to hear him be so passionate, gassed me up.

   24. DSDavid Senra9:53

       So that ties into what is the main theme across multiple decades? 'Cause like Paul Graham starts out as a computer programmer, right? Starts this company called Viaweb in the late 1990s, like two months or two years later, sells it to Yahoo for like $50 million, right? Then he's like, "Well, now I got money for the first time in my life, what should I do?" He's like, "I should learn how to invest." Starts this thing called Y Combinator, Y Combinator, you know, is the most prestigious startup school ver- version of like, i- if there was a college for entrepreneurship, which is impossible to ever have one, it would look t- a lot more like Y Combinator or anything else, that inve- he invests in, you know, thousands of companies, winds up becoming a billionaire off of this. And his entire theme relates to this, is like, what do you, like who are you as a person? What are you naturally interested in? Jeff Bezos has this great line where he's like, "We don't pick our passions, they pick us." Right? So Paul starts out, it's like, who you are as a per- like what are you into? He's like, "I'm really into painting. I'm really into computers. I like reading." He has like this deep historical knowledge of, you know, English history and everything else. And so it's like you start with who you are, then like what do you actually wanna do, like how do you find... A, a an essay that changed my life that I recommend everybody reads is How to Do What You Love. Um, and it's like, first of all, find out who you are, then find out like what you actually love to do, find a way to, to do what you love, but make sure that it's valuable to other people, right? And if it, and if you're making something people want, whether it's a podcast, a software program, a service, whatever it is, and you are, you really love to do it, you'll be really good at it, and if you're really good at it, you'll do it for a long period of time. And if you're really good at something, you do it for a re- long period of time, that's a, you have a high likelihood of getting wealthy. And so that is the main theme. That is why I think w- it doesn't matter what, whether you're working inside of a company, whether you're an entrepreneur, whether you're a podcaster, it doesn't matter, it's like I would read, I'd find Paul Graham's essays and read the ones, I, find the ones that you like and then read them over and over again, because I think they're extremely powerful. His clarity of thought and the clarity of writing is second to none.

4. 11:40 – 21:08

   The Hardest Workers of All-Time

   1. DSDavid Senra11:40

   2. CWChris Williamson11:40

      There was a internal Apple meeting with Tim Cook and someone asked Tim about whether it should feel like hard work when you do something that you love. And one of my friends was at this internal meeting, and he told me what Tim said in re- in response. He said, "You'll have to work harder than you ever have before in your life, but the tools will feel light in your hands."

   3. DSDavid Senra12:00

      Yes. So-

   4. CWChris Williamson12:01

      So fucking cool.

   5. DSDavid Senra12:02

      Think about, if, if you ask anybody...... who's the, who has the most drive or who's like the hardest worker you've ever seen and then one name will pop up over and over again, it's Michael Jordan, right? And I read, uh, not only did I read Michael's autobi- autobiography, Driven From Within, but I read this like 700 page biography which changed my fucking life and it's called, uh, Michael Jordan: The Life, I think, by Roland Lazenby. And what was so fascinating is Michael even says, he's like, "Everybody talks about how my work ethic and how hard w- uh, I, how hard a worker I was they didn't understand that it was all play to me." Like me, I've heard you speak enough where me and you also share love for the, the philosophy and the thinking of Naval Ravikant. Uh, in fact, our mutual friend, the way, the way we connect is Eric Jorgenson. And I, at Eric's book, The Almanack of Naval, it's like I give that away, uh, I think I may have bought that, more copies of that as like somebody to give away than almost any other book that I could think of. And especially for somebody that doesn't know what to do. They're like, "Man, I'm, I'm struggling. I don't know like what direction I should take my life." It's like read, read The Almanack of Naval. And so what Naval has this idea, it's like find work that feels like play, that's also in Paul Graham's essays, and you see it again in Michael Jordan. So it's like wait a minute, like maybe Naval was influenced by Paul Graham, but Michael Jor- Jordan sure as hell wasn't, and yet he arrived at that same conclusion. He's just like, "I'm the laziest..." And you would see this in his childhood. They're like, "Man, we couldn't get this guy to clean the kitchen, he couldn't do his homework, but when it came to playing sports, baseball first and then basketball, you couldn't, y- he would never get off the field." And then he'd realize, "Oh, where am I weak?" Then he'd go find, he's like, "Oh, I need to lift weights," or, "Oh, I need to work on my endurance. Oh, I need to find a coach that can actually teach me." And he was just an absolute sponge because it felt like play to him, and that's the whole thing. It's like it's very difficult to get really world-class, go back to the Joe Rogan. It's just like what are his, what are the things that he's obsessed with, right? He's obsessed with... And they all interconnect if you really think about it. It's like he was doing UFC commentary for free when it was nothing, you know. Uh, I wish somebody would write a biography of Dana White because that's a fascinating story that needs to be told. It's like you, you, you buy this, uh, company so, that's almost going out of business for $2 million, you blow it up, make it a worldwide sport, sell it to, uh, ESPN for what, $4 billion or something like that, um, and then you ask him, "Well are you ever gonna quit?" He's just like, "Uh, I love what I do. Uh, I travel the world. I stay at the best restaurants. I eat at, uh, or stay at the best hotels, eat at the best restaurants and watch the best fights in the world." He's like, "I'm not even working." (laughs) Like why would I, like there is nothing to quit. Like this is, there's nothing I'd rather do than this. Um, and so I, I think that that's like, you picked up on like that's the key. It's like if you really wanna be great at something, you have to do it for a long time and if you don't really love to do it, you're not gonna do it for a long time.

   6. CWChris Williamson14:39

      There was this story I heard about Steffi Graf, German tennis player, like savant when she was still playing.

   7. DSDavid Senra14:45

      Mm-hmm.

   8. CWChris Williamson14:45

      Uh, and as a kid they did an assessment of motivation and of, uh, technical skill and some people were coming in high on one and low on the other and so on and so forth. Steffi Graf came back as 10 out of 10 on both. So what you have with this person is not only someone who has the raw talent to be able to beat you, but they're gonna continue outworking you and to them it's not even gonna feel like work. And it feels trite to talk about this now, right, like no one can beat you at being you, it's very difficult to beat someone that's having fun, like, you know, uh, how many times do we need to drill this home? But perhaps one more time. Like it's an important lesson.

   9. DSDavid Senra15:19

      Actually I have so, I have something interesting to say about that because th- this is something that I discovered 'cause so like fundamentally, right? Um, I should back up, like for the podcast so far I've read, you know, close to 300 biographies of history's greatest entrepreneurs, right? Uh, to even get on Founder's podcast you have to be so good at your job, somebody wrote a fucking book about it. Like that's an insanely high bar, maybe the highest bar that you could possibly have, right? And so every, where everybody thinks is like these people must know something we don't, right? It's like must be super complicated or something. It's like no, no, no. It's like they identify the very, the basics, right? They fi- they identify a handful of things that are important to them and they repeat them f- decade after fucking decade. Jeff Bezos is a great example of this, right? Uh, if you think about it, like Jeff Bezos mastered, uh, what it means to run a high growth technology company on the internet before there were any playbooks, right? Like he essentially wrote the fucking playbook when he started in '97. How many people started s- uh, an internet company in '97 that are still going today? Like i- he wins by endurance. Let me actually show you something real quick 'cause this is gonna tie into it in case I forget. But like this is, this is, uh, my lock screen, right? That is a cover of Ernest Shackleton. This is a fantastic book written by Alfred Lansing called Endurance, right? And the reason I have Ernest motherfucking Shackleton looking at me every time I look up through my phone is because he had a family motto. His family motto was, "By endurance we conquer." And so something I've noticed from sitting in a fucking room by myself for four years seven days a week reading every single day of my fucking life. I read a biography of an entrepreneur for hours. That's the first thing I do. After I wake up, uh, I wake, wake up, work out, and then I read forev- for hours. As long as I do that for the rest of my life, I'll get whatever I want out of my life because then I package up what I learn and I put it on a podcast for other people to, to benefit from, right? And so what I noticed about these people is just like Je- ju- go back to Jeff Bezos example. It's like, um, he has a, an i- they call him Jeffisms. He ha- it's not like he needs to remember 25, 30 different things, right? It's a handful of principles that are very important that he's gonna repeat over and over and over again for decades. So I don't, I, I understand people say, "Oh, it's trite to say 'Do what you love.'" Or, "It's trite to say that you have to have endurance. It's trite..." It's like, no these are the fundamentals. There's a great conversation that happens between... So I've done, I don't know, uh, two podcasts on Michael Jordan and I've done like, uh, two or three on, uh, Kobe Bryant, I just read another 600 page biography on Kobe Bryant, right? That one of the last interviews Kobe did, right? This is so fucking important to understand 'cause you see this in every single domain. One of the last interviews he did right before he died, he talks about that he was on the phone with Michael Jordan, right? And he's like, "Michael," he's like, he's watching, uh, unfortunately the daughter that passed away with him in, in the, um, in the helicopter crash. He's like, "Man, I don't really like what their coaches are teaching. It's like they're teaching these 12 year old kids like all this fancy shit." He's like, you know, "spin moves and all this other stuff." And he's like,I am pretty sure I didn't learn this when I was, you know, when I was playing. So I was like, "Let me call Michael and see what he says," right? So he called, he's calling up Michael, he's like, he's like, "Hey man," um, you know, he explains the story. "I think they're, they're teaching these kids way too much fancy stuff. They're not focusing on just mastering the fundamentals on a deep fucking level. And the way to do that is repetition over and over and over again for a long time." And he go- and he's like, "Michael, what do you think?" He goes, he goes, he's like, uh, "Michael, what were you learning, uh, what were you doing in, in, uh, basketball, uh, when you were 12?" And Michael goes, "Dude, I was playing baseball." And then Kobe says, I'm pre- pretty sure he's being interviewed by Alex Rodriguez, the famous bas- uh, baseball player and he goes, "Think about that." And his point being is like, the greatest basketball player to ever live hadn't even picked up a fucking ball yet. Your 12-year-old does not need to know these spin moves and all this other fancy shit. Focus on the fundamentals. And they do that for, on a deep, fundamental level for decade after decade after decade. I want to go back to this idea that you and I both share, an admiration and love for Charlie Munger. He has this great thing where he's saying, "Hey master, the big ideas in all these domains." So he has this thing, he says like, "They carry most of the freight," I think is the term he word- uh, he, uh, he, uh, uses. He inspired me to be like, how can I, what am I learning from, you know, doing this rather unusual work that I do? It's like, my version is like, time carries most of the weight. I just heard, or I saw a tweet that you said where it's like, you've been doing this podcast 500 and some fucking episodes, right? First of all, you know as, as, as I do, and we don't have to get into the business of podcasting, 'cause I'll never shut up about it, 'cause I'm clearly obsessed, but like, everybody's like, "Oh, it's too late to start a podcast. There's millions of them." And then you actually look at the data and it's just like, how many of them are producing, uh, how many of them, basically how many of them are still producing to this day, have done more than 10 episodes, and haven't fucking quit? And it's like, a couple 100,000. And so my whole point is like, imagine being able to go back on the internet when there's only a couple 100,000 blogs or a couple 100,000 websites and you're telling me it's too fucking late? What are you talking about? That's insane, 'cause everybody quits at everything. And the reason I was so interested is like, not only do I respect Eric Jorgenson's opinion a lot and I find him an extremely sharp and articulate person, but he's like, "Chris is the real deal," but I can see that you're the real deal because it's like, this dude has done something 500 fucking times. How many people have done that? And then you had said something, it's like, "I've been grinding away, trying to get really good at my craft," and I want to talk about this conversation that you had with, uh, somebody I also admire, George Mack. Which, I didn't know his name was George McGill until you said something. I've been following him on Twitter for years. Um, and we've been DMing and stuff, 'cause he listens to founders, too. But he, another sharp guy. But, um, uh, but, the, the, the point I was making is just like, you made the points, like, "I've been grinding, grinding, grinding" and yet, this is something I also, uh, talk about on the podcast is that, you have to stay in the game long enough to get, to get lucky. Because there's an opportunity, right, that's gonna happen year five, six, seven that you cannot comprehend in year one, two, three. This is very similar to what Jocko said in your conversation. He's like, "I don't have a five-year plan." Guess what? The way Jocko talks about, eh, the fact that he's optimizes for flexibility, uh, and optionality, is how all of the best entrepreneurs that have ever lived they talked the exact same way.

   10. CWChris Williamson20:57

       Do you think that's, do you think that's the case, they have this sort of emergent, uh, outcome in life?

   11. DSDavid Senra21:02

       There is, I don't know about an emergent outcome, but they definitely optimize for optionality. So there's this guy, um, I don't want to lose the

5. 21:08 – 26:37

   Optimising for Optionality

   1. DSDavid Senra21:08

      thread. Real quick, let me, so I'll tell you about Henry Singleton in a minute, but how I like what you said. It's like, that one opportunity that you had to grind away at for years and years, and you never probably predicted it would happen, but once it happens, I think you said you had more downloads in like, you know, a week or whatever, than all the years combined.

   2. CWChris Williamson21:23

      Yeah.

   3. DSDavid Senra21:23

      That's a perfect fucking example of stay in the game long enough to get lucky. There's a million fucking examples like that in the history of entrepreneurship. You just have to go and read old books to find them. So, let me go back to this optionality person. So, what I'll do is when I find somebody that's very interesting to me, right? Um, I, what you'll be shocked is, is like how almost none of their ideas are unique to them. Right? So like, I'm obsessed with Warren Buffett and Charlie Munger. Uh, I read all of Warren Buffett's shareholder letters. Uh, I read all the biographies I could find about both Warren Buffett and Charlie Munger, and when they say, "Hey, go study this person," and they do, because they're both obsessive readers, they, they're both biography nuts. Uh, Charlie Munger has probably read more biographies than me, but I don't think I'll catch him, 'cause I got 60 years, you know? He's got 60 years. So there, but they, what's fascinating is like you find all these great people buried in history. And we can talk about why I don't, don't worry your legacy and all that other stuff, 'cause it's, a lot of it's fake, you wouldn't imagine how so few people actually go back and we could talk about, uh, some examples in the history of entrepreneurship. But, what's fascinating is like Charlie Munger's the wi- one of the wisest people alive, right? And he's like, "Hey, the smartest person I ever met was this guy named Henry Singleton." I'm like, "What the fuck?" And he's like, "His returns were, uh," he's like, "utterly ridiculous." You know how Charlie talks. Then Warren Buffett's like, "You guys need to go back and read about Henry Singleton." (clears throat) He built a conglomerate very similar to Berkshire, but like 20 years earlier, right? And they're like, Warren says, "Hey, it's a crime that American business schools don't study this guy." So wait a minute. So let's pause right there. You have how many people on the planet have studied more entrepreneurs and more businesses than Warren Buffett? A tiny, m- he might, you know, have studied more than anybody else and this, and he's telling you, "Yo. This is the guy. Go fucking pay attention to this guy." And then he says some shit like, "Hey if you add up the top 100 business school graduates, uh, MBA graduates ever, uh, their record, and, and then compile their record together, it would still be inferior to Henry Singleton." So then you go and you read, there's not a lot of material on Singleton but I read everything I could find, and I did an, uh, uh, a podcast on this book called The Outsiders, which is one of the very few books that profiles wha- what made Singleton so i- uh, so interesting. And I absolutely flipped my shit because all of the ideas that I thought were Buffett's, a lot of them, came from Singleton. And to me that's inspiring 'cause it's like I don't, I can, I can thrive and be wildly successful and I don't need one single original idea of my own. I just need to master what o- uh, what some of the best people in history have already figured out for me. And then you could pick up the book and in, you know, 10, 15, 20 hours you get the distillation of a career and lessons they had to figure out over 40, 50 years. That's absolutely insane, so Henry Singleton's like, listen. He has got this famous quote, uh, he's like, you know, everybody has a, a lot of, eh, eh, especially in the 1960s and '70s, there was this theory that you need like a five-year plan, you need a 10-year plan, you need to have all these projections. He's like, "The world is so much more complex than that."He's like ... And we have so little control over outside things. So, he's like, "I like to steer the boat every day." He's like, "My only plan?" You know what his fucking plan was? Same plan as Jocko. "I'm gonna show up every day, go to work, and I'm gonna steer the boat a little bit. Like, in one direction. And I'll go and I'll try something and if it works, I'll do ..." What Jocko said, "I'll do more of it. Oh, it didn't work? I'll stop doing that." That's fine. And I love what he made, the point he made on your episode, which was fantastic, uh, which was, "Hey, if you asked me six years ago what my five-year plan was," he's like, "I didn't have a podcast." And then all the stuff. He's like, his podcast blows up, he sells all these books. Now they're being turned into movies. He's got his manufacturing company. He's, I ... Yesterday, I came back just for this, by the way. Uh, I was out of town for Thanksgiving and I was like, "Sorry, I'm leaving. I have to go record with Chris tomorrow." And so all the way, I, I had to, I had to do this like four and a half hour drive yesterday, and I'm just sh- uh, slamming Jocko Goes 'cause all the Starbucks are closed (laughs) on Thanksgiving Day (laughs) . So I was like-

   4. CWChris Williamson25:02

      Jocko Goes is legit, man. I was really, really impressed with him.

   5. DSDavid Senra25:05

      The only things that are open are the Wawas. And Jocko has made a huge influence on my life, and I'm not an energy drink person. I'm a espresso person, like all day long. But I was like, "Fuck Monster, you've never done anything for me." It's like, Jocko has given me hundreds of hours of fantastic content. His ... I, I don't read a lot of books that are not biographies, but his book, Extreme Ownership, is the be- to me the best, single best book on leadership that I've ever read. And I was like, "I'm loading up on Jocko Goes," so I was just slamming 'em down a- as they went by. But yeah, so what I saw with Jocko, I saw, uh, even, uh, Warren Buffett and Charlie Munger saying the same thing. It's like, "We don't have a master plan." He's like, "We're gonna ... D- d- the opportunities are gonna come in. A lot of them we can't predict. We're gonna say, 'Do we wanna pursue this opportunity or not?'" And-

   6. CWChris Williamson25:41

      Why-

   7. DSDavid Senra25:41

      So my-

   8. CWChris Williamson25:41

      Why-

   9. DSDavid Senra25:42

      Go ahead.

   10. CWChris Williamson25:42

       I think that's reassuring to people is that ... I, I struggled. I was one of those people that didn't have a very good plan. If you would say, "What do you want written on your obituary? W- w- what, where would you like to see yourself in 25 years?" That's something I've always struggled with. And yet because I came from a productivity, efficiency background, at least when I first started this show, that was one of the things I was obsessed with, I always felt like a, I don't know, a little bit of a fraud because I didn't have that as it was laid out. And (clears throat) I think that you're right. Understanding principles and allowing things to be directed from there each day, one step at a time, permits you to have enough optionality to take advantage of good opportunities when they come to you. But it is important to have the principles. I think without an understanding of what it is that I need to be doing, consistency, enthusiasm, discipline, ensuring that I fall, uh, I, I continue doing the good stuff. Whatever the things are that facilitate your performance, those need to continue, but you don't necessarily need to have the plan all the way out.

6. 26:37 – 35:14

   Most Common Traits of High Performers

   1. CWChris Williamson26:37

      So when it comes to looking at all of the guys and girls that you've studied from history, what are the most common threads in terms of personality types, the ways that they show up, that all of the high performers have had?

   2. DSDavid Senra26:50

      So it's not ... It, uh, it's funny because I've been approached by a couple of publishers and they're like, "Hey, why don't you write a book on, like, the top 10 traits?" I'm like, "Fuck you." Like, it, it ... They ... If, if you think about it, like, the world is much more complex than that. And what we're doing, right? Like, a podcast is a business, it's a form of entrepreneurship. Like (clears throat) entrepreneurship done at the highest levels yields the greatest financial results in the world, right? There is no formula possible. So what, the way I look at it is, uh, same way where, like, um, when I just re- read this, this 600-page biography of Kobe Bryant. Like, you would go to his house at like 17 years old and like you'd open the closet and it'd be VHS tapes of Michael Jordan, of all these different ... Magic Johnson, all these other people. His girlfriend, his high school girlfriend in that book, is, gives this interview, and she's like, "What was it like to date Kobe Bryant in high school?" She's like, "Well, uh, a lot of Saturday nights at his house watching tapes of Michael Jordan." Right? So the way I think about it is, like, reading biographies of history's greatest entrepreneurs is, one, all of history's greatest entrepreneurs did this. The more biographies you read, right? The more you realize that people who lived lives so remarkable that somebody wrote a book about them all read biographies. Like, it is ... You can read other things and you should read other things, but I don't think, uh, uh, you can have a complete human life without reading biographies consistently. You know? Uh, the way I always say it is like, uh, ah, like people are like, "How should I use Founder's Podcast 'cause now there's like 400, over 400 hours and like I add to it constantly?" It's like, listen to an episode, find one book that you like, read one biography a month, right? Uh, this is like the minimum, like, requirement, in my opinion. Read one biography a month and then listen to two episodes a week. It would ... That means after a year you would have downloaded key insights and lessons from 100 different history's greatest entrepreneurs every year. And then you gotta go deeper, because my episodes are only an hour, maybe 90 minutes. It's like these books take me ... For every one hour of audio that I create, I'm reading at least 20 hours. Like, this is not a fucking game to me. Like, I take this dead, dead seriously, just like history's greatest entrepreneurs do. So, one thing I, I would say, like one trait all, uh, like, that a lot of them have is the importance of practice. Um, and so there's this maxim that I repeat over and over again, that the public praises people for what they practice in private. The public praises people for what they practice in private. I repeat that to me over and over again. And I mentioned earlier, I was like, "How, why did this guy say that reading a biography of Michael Jordan changed his life? Like, what the hell does ... Like, that sounds silly to me. Like, how could that possibly be true?" And there's this one story in there that I thought was so fucking remarkable because it talks about the difference even at the highest level. So, to get into the NBA there's like, what? 400 NBA players total, right? Out of millions of kids that want to do it, and have maybe attempted to do it. Then you get to like the All Star and maybe you have, you know, 24. Now the 400 is down to 24. Then in 1992, Jordan is invited to play on the Dream Team in the Olympics, right? He, uh ... So now you have 12th. Like he, they ... You can't get higher than where he's at, and he was thinking about not doing it 'cause he's like, "I've been in the playoffs, we're winning championships." He's winning every single award he could possibly have, he's at the top of his game, but he's like, "I'm going to do it even though my body's beat up because these are the best basketball players in the world," right? "And I want to see their practice habits." So the main ... The reason I say that business, uh, that book changed my life is because Jordan says he'd rather miss a game than miss practice. And so he gets there and ... I get goosebumps. I already have goosebumps when about to ... 'Cause I know where the story's gonna end. And he gets there and he sees the practice habits of the other people on the Dream Team, which they are at the top of their cla- uh, uh, of their profession, but he's winning more championships than them, he's ha- his accolades are just better than ... He's a- he's at the very top. And he said something that fucking changed my life, and he said that they were deceiving themselves about what the game required.And so that, from there, how I apply it to my work is like, I'm gonna work on the podcast seven days a week, I'm gonna read, uh, biographies for, uh, for hours and hours every morning. When I'm done, I store all of my highlights, uh, and my notes in this app called ReadWise. I have over 20,000 highlights and notes from all the books I read. And so what it, what's my, my second half of my day is fucking practice, which is now rereading. It's not good enough that I read a book a year and a half ago. That's not fucking good enough, dude. You're asking people to spend an hour and a half of their time with you in their ear. So I have to make sure that I am not only, like, I have to live this stuff every single day. I was just invited to speak at a company. It's a private investment company, it's 93 years old. The CEO of the company is one of the successful founders. They have $250 billion of assets under management. And the CEO, me and him get on a Zoom beforehand, uh, they're having a company offsite with like 40 to 60 other partners. And he's like, "Hey, do we want an outline?" Or whatever the case is. I go, "I'm perpetually prepared. I promise you, I will show up, you can ask me whatever the fuck you want and I will know it backwards and forwards." And he's like, "Why?" And I explain my, like, I go, "I got this idea from Michael Jordan." And then, "I'm not fucking playing basketball over here. I'm making podcasts and reading books." But this, the principle is the same thing. So let me tie this to one of history's greatest entrepreneurs. Sam Walton, right? If you think about how fucking crazy Sam Walton's story is. That dude started out in retail when he was like in his early 20s, right? Doesn't hit it for like 25 years. He was like 44 when he founded Walmart, right? But he wasn't like lollygagging. He was like working at different forms of retail. He was just having to go through that experimentation, the time carries most weight thing, right? And so he had this idea for Walmart. He was under fine- finance, and his idea was, "Hey, uh, all the big retailers in the big cities, I'm gonna see if I can build these stores that are far out in rural America, right? In tow- towns of 8,000, 10,000, 15,000 people, right? Uh, I'm gonna pick cheap real estate and I'm only gonna compete on price." His th- the thesis behind Walmart, which if you think about this, this thesis was proved correct. As a result this, of his thesis being proven correct, he generated one of the largest fortunes the world has ever seen. His fucking kids are still like, if you combine all of Walmart's kids, like, uh, like his descendants into ... He split it up, right? But if it was like one person, they'd be the richest, one of the, if not the richest person in the world, right? Um, and that idea came from this, it's just like, "Well, I think there's an opportunity here that no one else is pursuing. I have an hypothesis, let me test it." He didn't have money. He goes to, uh, it was a, this company called Ben Franklin Stores, which is ... I, I might be getting the name of the company wrong, but it was essentially like a, a early franchise, uh, co-, uh, headquarters that would franchise. Uh, you could buy retail franchises from them. And Sam was running one of those. And he pitched them on the deal. And they're like, "No, no, we don't want to do this." That was a Friday. The next day, the guy that told him no goes to his local Kmart, right? Just to go shopping for whatever, 'cause Kmart was a giant company. And he hears this voice, he's like, "Who the fuck? Why does that voice sound so familiar?" And it's Sam Walton in there, in Kmart with his notebook, which he would go ... Sam Walton went in more, his version of practice is going in more retail stores than anybody in history. His kids talk about this. He's like, "It doesn't matter if we're in Europe on vacation or anywhere, any vacation." He's like, "We have to stop and Dad has to look at the stores every day." And so this guy that had just turned him down from one of the best opportunity, which turns into Walmart, right? So he fucked this up. He just said no to the best opportunity of his life, sees Sam Walton talking. He's like, "Okay, how do you guys do inventory? Okay, why is this priced this way?" Taking notes on a Saturday morning. That's his version of professional practice. And I saw somebody tweet about this and, um, they're like, "Imagine competing with Sam Walton." And so the way I look at it is like, when you're reading these biographies, when you're picking up these ideas, you might read a 400 page book or you might re- listen to an hour and a half of my podcast to pick out one or two ideas, but those ideas will stick with you forever. And then you can figure out how that applies to your actual craft. No one, goes back to the, the Henry Singleton thing. You, you mentioned something I, I wanted to jump on where it's just like, none of this works if you don't work yourself in a position to trust your own judgment. As a podcaster, as an entrepreneur, as an investor who obviously I, I ... These are the people I make my podcasts for primarily, right? If you can't trust your own judgment, you were just saying you used to have a business partner, now you're at the top of the heap. It's, uh, which you'll also see Paul Graham talks about. It's like founders talk ... They, they realize like other founders outside of their company, and Paul talks about this in his essays, have a more of an understanding of what they're going through than their employees. They can't talk to their employees about that. You also have, uh, you and I have a gift where the easiest way to make friends is to have a podcast and then you listen to other people's podcasts and now you're friends. (laughs) So like you can talk to other people. Um, so those are just some of the ideas. I don't wanna keep rambling, but those are just some of the ideas that appear over and over again. It's like the importance of practice. It's like, uh, the un- unbelievable amount of dedication. Jocko said that, uh, on his podcast. It's like how many, uh, I, I heard him say something on, uh, on Instagram Live one time that just made me laugh. And you know, he's like looking at his phone, like reading the questions and they're like, "How many hours a week do you work?" He goes, "All of them." (laughs) It's that kind of thing. 'Cause even if they're not physically ... Even if Sam Walton's not physically working at his business, he's thinking about it. That is a form of work.

   3. CWChris Williamson35:12

      So that to me is obsession

7. 35:14 – 43:55

   Are the People David Studied Generally Happier?

   1. CWChris Williamson35:14

      and obsession's not necessarily a bad thing. I would have said one of the most common threads that I've seen amongst high performers that I've had on the show is obsession. You could argue that that might be compulsion, uh, by a different lens. Do you think on average that the people that you've studied from history were happier than the average person?

   2. DSDavid Senra35:35

      That is a great question. I think for a large percentage of them, happiness is besides the point. So this is, we- we can seg-

   3. CWChris Williamson35:41

      That's not the question though.

   4. DSDavid Senra35:43

      Go ahead. Good. Say it again then.

   5. CWChris Williamson35:44

      The question is, on average do you think the people that you studied from history were happier than the average person?

   6. DSDavid Senra35:55

      Yes. This is the reason why. Even if they're n- not over ... First of all, I, I, I don't, I think you were talking about this with Ryan Holiday. Which is like, there is no evolutionary point to be satisfied or to be happy. There like a finish line which I think is, uh, a big mistake. People will always ... Like the hedonic treadmill. It's like people are always chasing after something, they get it and they don't understand why they're not content.So, I, it's, like, something I don't even worry about anymore. I just do what I wanna do every day and it's just like I know I'm always gonna ... A 10 or 20% of my life is always gonna be discontent somehow. You know? As a driven person trying to build a business, like, if you were content you wouldn't do anything. Um, the reason I would say they might be happier, though, is because a lot of people think entrepreneurs are motivated by money, right? And the money obviously, you know, Jeff Bezos likes, probably likes his $200 billion. Probably feels really good (laughs) , right? But, uh, i- it's very clear, it's like they're motivated by control and independence. They want control on how they spend their time. Like, business building is world-building, right? You're able to build, uh, the, a world within your world. Like, in your c- in you and I case, right, we get to choose wh- what we're gonna do when we wake up tomorrow. You get to choose who you speak to. You get to choose ... You have complete control over people around you. I have friends, man, that e- even if they like their job, they hate some of their coworkers. Imagine how unnatural that is from an evolutionary perspective, to spend half of your waking time around people you dislike or don't trust. Like, th- so, and to that degree, I think because they have control and they ... And Sam Walton's case, he's like, "I had fun." You know? It just, that's a, it's a ... He ... One of my favorite quotes of his is like, uh, "Most people don't enjoy what they do. I, like, I really enjoyed it." And he wrote those words when he knew he was dying of cancer. He had cancer all over his body. He knew he was dying. And he's looking back, he's like, "No, I w- there, I, there's very few things I would change." The ending of Phil Knight's, uh, founder of Nike, his, he has a fantastic, uh, uh, autobiography called Shoe Dog. What was crazy is, that talks about, like, th- he, he has this dream, right, of ... He has this goal he wants to do or this idea he wants to do. And then that book, every chapter is a year, it goes in, uh, in chronological order and it ends with the IPO of Nike. And the crazy thing is, this guy overnight, you know, now he's worth 100, 100 and, like, $75 million overnight. He's like, "This is amazing." And then he gets to the end of the book, he's like, "What do I wish?" He goes, "Oh my God. I wish I could do it again. Like, I wish I could go back and literally redo this." And now he's writing those words as a 70-year-old man. He knows, like, there is no time for that. That's not gonna happen. Um, so yeah. They may be happier than the average person because they have more autonomy and control over what they're doing. But these are not, like, I don't even know if they're, it- it's possible for many of them to be, quote-unquote, happy.

   7. CWChris Williamson38:24

      Yeah. I-

   8. DSDavid Senra38:25

      Or content.

   9. CWChris Williamson38:25

      So, the common ... Like, the answer that I would usually give when people ask about high performers, I had, uh, the performance coach, Michael Gervais, who was the guy that looked after Felix Baumgartner's psychological training for him to jump from the edge of space.

   10. DSDavid Senra38:41

       Oh God (laughs) .

   11. CWChris Williamson38:41

       Had, had him on the show. Uh, and Felix-

   12. DSDavid Senra38:43

       Yeah (laughs) .

   13. CWChris Williamson38:43

       Felix was struggling. He had claustrophobia when he got inside of his suit and there was pressure. Michael was brought in to coach him back out of that.

   14. DSDavid Senra38:49

       (laughs) .

   15. CWChris Williamson38:49

       And I asked Michael, "On average, do you think that the highest performers in the world are happier or, or more miserable?" Uh, and his opinion was that they're more miserable. And the reason that he gave was that a lot of people that are high performers are driven by a sense of insufficiency, that they're looking to achieve success in the outside world to fill a void which is inside of them. And that is a common thread that I've seen with people that I have spoken to, that I've worked with, that I've been around. Um, but I'm also perfectly open to hearing from you, someone that's been exposed to tens of thousands of hours of intimate connection with some of the most smart and successful people from history, that that might not be the case. Um, I do think a lot about whether people are sacrificing the thing that they want in order to achieve the thing which is supposed to get the thing they want. So for instance, a lot of people would consider that being successful might make them happy, and in order to be successful, they will sacrifice happiness in the short term. And you go, okay, so you have an equation here, where if all that you do is remove success from both sides, i.e. the strive, what you're left with is just happiness. And it's that story about the fisherman, the guy that goes down to-

   16. DSDavid Senra39:58

       Yep.

   17. CWChris Williamson39:58

       ... see the fisherman and he says, "You could build this up into a business and then if you built the business so big, all that you would be able to do would be a fish all day." And he goes, "Well, that's what I do right now."

   18. DSDavid Senra40:05

       (laughs) .

   19. CWChris Williamson40:05

       And I do wonder how many people, uh, are the fishermen. Uh, sorry, are the businessmen going to see the fishermen looking at him and saying, "Look, th- there is, there is a void inside of me that can be filled by success in the outside world, and the success will ultimately lead to happiness"? The problem is that we look at the modern world through such a narrow band, a narrow domain of competence. You saw this with, uh, who was the dude that did Fyre Festival?

   20. DSDavid Senra40:28

       Oh, the one that went to jail?

   21. CWChris Williamson40:29

       Yeah, him. That guy.

   22. DSDavid Senra40:30

       Yeah, yeah. Uh, yeah.

   23. CWChris Williamson40:30

       Anyway. The, the only reason that people don't like that guy, and it's a hilarious story, is because the event didn't succeed.

   24. DSDavid Senra40:37

       Yeah.

   25. CWChris Williamson40:37

       If he'd had different weather, if he'd had different beds, if he'd managed to get the, the tents to look even remotely okay-

   26. DSDavid Senra40:43

       Mm-hmm.

   27. CWChris Williamson40:43

       ... he would have been hailed as the greatest event p- promoter of the last few decades, right? It would have been the greatest thing since Woodstock.

   28. DSDavid Senra40:50

       Yeah.

   29. CWChris Williamson40:50

       Uh, the only difference is that he didn't get the outcome that he expected. Well, hang on a second. People aren't pointing the finger at him because he didn't get the outcome when it failed. They're pointing at him for these unethical business practices in the lead up to it. So what that suggests is that the ends always justify the means to people. Do you understand where I'm coming from here?

   30. DSDavid Senra41:11

       I do.
8. 43:55 – 1:00:35

   Do the Ends Justify the Means of Success?

   1. CWChris Williamson43:55

      sad about that, though? That a lot of these people have got families, you know? They could've spent more time with their kids. They could've spent more time connecting with the people that they care about. This is my concern with unfettered, complete blue sky ambition and ruthlessness, that it, I worry that it sets a trend for people to believe that they need to go searching outside of simple lifes, simple lives, in order to achieve something that they, that will fulfill them, when what it is that they're looking for is right in front of them. Like, these people are unbelievably ambitious. They're very obsessed. And what that leads them to do is to engineer a life which allows them to manifest that obsession, and it may be one of the greatest things for this particular person to go and do. Enzo Ferrari may have been built to create cars, probably was, but would his life in retrospect have been better had he have spent more time with his kids? Would his kids' lives have been better had he had spent more time with his ch- ... I don't know if he had kids. My point being, like, looking at it through the lens of how do I maximize impact in the world, whether it be legacy, whether it be growth, whether it be money? And it's often not just the cash, as you've said. It's people continue after that, and you go, "Okay, well, like, what are you doing this for? You're doing this in pursuit of the pursuit itself." Cool. Great. Is that all that there is to life? Is a bigger question.

   2. DSDavid Senra45:19

      So, out of every single person that I've ever studied, they have all over-optimized their professional life at the detriment of their personal life, by far. There is one lone exception to this. Uh, it is episode 222. It's this guy named Ed Thorp. He is, uh, the title in the fucking podcast I made is My Blueprint for Life, right? And, um, he's got a fantastic autobiography. I recommend everybody read it. It's called A Man For All Markets. Um, Nassim Taleb wrote the forward, and you can actually read the forward for free on Nassim's website, which is, uh, uh, fantastic, and he outlines why Ed Thorp is so unique. Now, I have to preface this. Ed Thorp is a genius, way smarter than I am, by far, way smarter than I'll ever be. I could read 10,000 books, I'll never be as smart as that guy, right? So, what Ed Thorp realized is, like, enou- when enough was enough, so he identified a handful of things that were really important to him. He's like, "I wanna get wealthy," right? "I wanna have work that's intellectually stimulating. I wanna be a good father. I wanna be a good husband, and I wanna take care of my health, and I wanna have fun. I wanna treat life like the adventure it is." There, Tim Ferriss just is, is fantastic. He's still alive, right? You can go ... Tim Ferriss did a two-part interview with Ed Thorp recently. You can listen to it, but I recommend seeing it on YouTube because, let's start with the health thing, which I know you're into as well, right? Um, I sent that video to a ton of people, and I was like, "Tell me how old you think that guy in that video is?" And everybody's like, "I don't know, 65?" I was like, "He's 90. He's 90." And so what the genius in Ed Thorp is, like, he had, uh, a few simple systems and simple rules to guide his entire life. So, he got into physical fitness when he was a really young man. I think he was in college, right? Which is extremely rare, you know, 60-something, 70 years ago. And what he realized, he's like, um, "Every hour I spend in, uh, working out is one less day I'll spend in the hospital at the end of my life." And he dedicated himself to eating healthy, to taking care of, uh, of his physical fitness, and that's why he looks the way he does. He has actually a simple system I, I, I use in that book where he gets up every morning, obviously go to the bathroom, and then he weighs himself. And the reason he does that is, like, it's impossible for me to give, like, he, he has tight food feedback loops for everything. He's just like, "You're gonna know when, oh," he's like, "I lost a couple pounds. I can eat a little bit more today," or, "Oh, I can have that dessert," or whatever. It's, like, a very simple feedback loop, right? He was the inventor of the first quantitative hedge fund, okay? Uh, he, he would turn down, after he got independently wealthy, and it was all, like, uh, something that he found intellectually stimulating, he had unbelievable amounts of business opportunities that come through the door, and his whole point is like, "Even if I'm not a billionaire, I have hundreds of millions of dollars. I have this giant house in Newport Beach, California," right? "Uh, I have more money than I'll ever spend. Why would I take time away from my, raising my sons, uh, spending time with my wife, uh, having fun, to go chase more money? Something's wrong with me if I'm doing that. Now, if I happen to be, uh, intellectually stimulated and I find what I'm doing fun, then I'll go do that." But it was, like, invest in oil tankers or stuff like this. Like, "I don't give a shit about any of that." Um, he writes the book after his wife dies of cancer, and he talks about, he's like, "They were married for 50 years." He's like, "We spent ..." He goes, "I went home every day and had lunch with my wife."He's like, "I worked 40 hours a week." Right? Like, he was not a compulsive workaholic like a Steve Jobs or an Enzo Ferrari or Jeff Bezos, whatever the case is. Uh, he has great relationships with his sons and ... He might have a daughter too. And now their kids. Where, uh, the founder of IKEA, right, which is a fa- fascinating story. It's called In- His name's Ingvar Kamprad. He started IKEA when he was, like, 14, worked on it till he was, like, 87. Right? And he has a line in his autobiography that fucking gives me the chills. And this is something ... I have two kids, so I'm not fucking this up. And he says, uh, he goes, "I sacrificed the relationship with my three sons. I missed my three sons growing up to build IKEA." And he's like, "Don't do this." And he says a line, he goes, "Childhood does not allow itself to be reconquered." That is a very common mistake at the end of a lot of these autobiographies and biographies is like, "I didn't- I missed my kids' childhood and, uh, you can't get that back and I fucked it- fucked that up." Right? Um, let me go back to Ed Thorp and then I wanna tell you about this guy Larry Miller, who wrote a book that I think everybody should read. It's called Driven: An Autobiography. He was the richest entrepreneur in Utah, had a 30,000 square foot looking- uh, 30,000 square foot house overlooking Utah, owned 93 different companies. He's writing the book as he's dying and he's like, "My life is a cautionary tale. I didn't have fun. I didn't take care of my health." He owned the Utah Jazz. Go look up Larry Miller Utah Jazz. You see this obese man sitting there on- in one of those, you know, scooters or whatever, like the- that people came along-

   3. CWChris Williamson49:38

      Like a Little Rascal.

   4. DSDavid Senra49:39

      Yeah, yeah. Like, so, uh, I'm gonna run down what he said too, 'cause I think that- that's valuable even if people don't read the book. Let's go back to, uh, Ed Thorp. So then he- he builds this wonderful business, right? He meets ... He- he has a- he lives with a life adventure. He winds up having dinner or, uh, ha- he has dinner, they're both in their late 30s, with a 38-year-old Warren Buffet. Right? He has dinner, leaves the dinner, they wind up being friends. He leaves the dinner, turns to his wife and she- he goes, "He's gonna be the richest man in America one day." Imagine being able to, like ... Everybody sees Warren Buffet now as, like, this old guy, you know, kind of chubby or whatever, eating fucking Diet Coke and McDonald's and stuff. But like, I always, like, what I always do is, like, when I'm studying somebody, it's like, I'll write in a book. It's like, I wanna know when were they born and then as I work my way through the book, I look at the years like, "How old was that person? What were they thinking when they were 25?" I'm in my late 30s. Like, what were they- what were they doing when they were my age? It's like, we- we know the older version of them, but it's the younger version that built th- their empire. It's like, what did that person look like? You can see what Warren looked like when he was ... He had hair, he had glasses, he dressed nicely, he looked- he was, like, a sharp-looking dude. Charlie Munger too. Um, he winds up being the first LP in, uh, Citadel, which is, like, one of the largest funds in the world. So, my point is, like, the guy had all these interesting ... Uh, he built the world's first wearable computer with Claude Shannon, the father of information theory. Uh, he, uh, uh, Ed Thorp invented card counting for blackjack when you know ones and zeros and all that stuff. He- he's the one that invented that system, writes a book in the 1960s called Beat The Dealer, sells millions of copies. This is my blueprint because it's like, yeah, uh, he was smart as hell, he made a lot of money, but he was good- he was a good friend, he was a good father, he was a good, uh, husband. He took care of his health. And then he had fun. You wouldn't believe how many of these people get to the end of their life and it's like, "Oh shit, I didn't make any time for fun." And that's not how I think. It was like ... Dee Hock is the founder of Visa. He just passed away. He's 90- I think he was 93 years old. A very wise person. He- he turned his back. He- he, uh, he created Visa, ran it for, like, 15 years then he's like, "I don't wanna do this anymore. I don't give a shit about money." He would wake up in the morning, at 5:00 in the morning, write. He was obsessed with reading and writing, like almost all these people are. And would write a thousand words. Then he'd go out and spend the- his day working the land, physically restoring the health of the land he bought. It was somewhere in the Pacific Northwest. So, he said something that was fantastic. He's like, "Life is a magical odyssey to be experienced." And that's where, um, I- I don't ... I hope people realize, like, when you read these books, yes, you celebrate their accomplishments, but the reason that you re- need to read biographies over business books is the human element. They get to the end and they'll tell you, "Don't do this." Or, "Yes, do this."

   5. CWChris Williamson52:09

      What's the price that they paid for that?

   6. DSDavid Senra52:11

      Yes. And so we go to Larry Miller, Driven. Uh, it's called Driven: An Autobiography by Larry Miller, right? And this guy, you know, raised in fucked up situation. His- h- like, he'd get in a fight with his mom and his mom didn't know how to deal with him, so she'd call the cops. She put her son in jail over and over and over again. Then eventually kicks him out, right? And so he's got no education, no skillset. He is working in- as- in a parts department of a car dealership. I think he's, like, 25 or maybe 30 years old and he just fucking snaps. And he's like ... He had a fanatical desire to achieve something. And so then he just starts working literally. He's like, "If my eyes are open, I'm working." Right? Winds up building over the next 30 years, doesn't take care of himself is all. Uh, he's- they said if- if you lived in Utah, it'd be impossible not to ... Uh, it was impossible for an average Utah citizen to not spend money at one of his businesses. So he owned car dealerships and movie theaters and the Utah Jazz and all this stuff, right? Didn't take care of his health, didn't know his kids, didn't know his wife. Uh, gets to the end of his life, it's like they're having to cut off his fingers and his hands 'cause of his poor circulation. He's, like, obese. Really, like, disgusting. He's writing the book as a cautionary tale, right? And he says, "Listen, uh, if I could do it all over again, I would have, like, stopped, you know. I- I would- I'd still try to get rich but I would've, you know, maybe instead of making, you know, hundreds of millions, maybe make 10 million or 20 million," or whatever the case is. But the most devastating part is, like, "If I could do it all over again, I wouldn't have missed my- my kids growing up and I woulda had fun." And I'm like, "What is the point of living in a 30,000 square foot house owning a fucking NBA team and you didn't even have fun?" Then the co-author ... He dies in the middle of the book, right? As he's trying to write this book, his co-author is interviewing his wife and she says the most devastating thing, that, "If my family said about this me ... uh, about me, I don't care if I have a billion dollars, I'm a fucking failure." And she goes, "I miss him but it's not like he was here when he was alive anyways."

   7. CWChris Williamson54:05

      Dude.

   8. DSDavid Senra54:08

      Yeah. So that's the power ... When you read a book like that, um, you get to the end just like, "I'm not going out like that." You- you either- you either have the abi- Let's go back to our mutual love for- for (laughs) Charlie Munger. He says, it's like ... He quotes Cicero where he's like, "A man that doesn't, uh, know what took place before him is like- goes through life like a baby." He's like, "If you don't learn-"If you- if you are only capable of learning through your own experience, which most of humans are, right? It's very hard to learn through the experience of other people. It's like, you're gonna have a rough go at life. You will not have a great life. Okay?

   9. CWChris Williamson54:36

      Uh, what you will probably be able to do would be learn from the experience of other people that are similar to your sort of age cohort, right? Like, you're gonna be around most of your friends, "Oh, what did you do?" "Oh, I tried this thing with my business. I tried this new strategy for getting up early in the morning. I went to bed and took this supplement," did whatever. You don't get to do what people who have got to the end of life, and then subjectively looked back and told you, "This is what I would have done if, in retrospect, I had lived a life worth living." That's what you're optimizing for. I think there's, like, a really, really strong case to be made that a good life is one which, in retrospect, you're glad that you lived. There is some elements of that that you miss off, particularly the hedonic stuff. Like you don't- you don't embrace s- um, more hedonic pleasure in retrospect, and yet it does provide you pleasure in the moment. And that's a little bit of a paradox. Uh, or maybe-

   10. DSDavid Senra55:25

       Yeah.

   11. CWChris Williamson55:25

       ... a- a dichotomy to be managed rather than a paradox to be solved, as Hormozi says.

   12. DSDavid Senra55:29

       Mm-hmm.

   13. CWChris Williamson55:30

       Um, but I think that, especially if you're the sort of person that's listening to this show, that listens to your show, you're gonna be a bit more ruminative. You're gonna do introspection. You're gonna consider, "Why am I here? Am I adding value?" You need to optimize your life to be one which, in retrospect, you feel good about. Because not only will that probably be things that are good for you, both in the moment and in future, but in the future, it's like a gift that you give yourself. You get to accumulate all of these senses and feelings of goodwill and of achievement in a holistic, organic, ecological view. It's wholesale, right? It's everything. It's not just this narrow domain, it's everything. And that's why it's so important to be able to have a clear view of your life because I wonder how many of these people, maybe some of them in the autobiographies, are still retreating to their own inner citadel, which is, "I am happy that I achieved this much. I am happy that the business did all of these things." Because the temptation to open up the lid of looking at what they maybe missed would be so catastrophic, especially as you're perhaps a bit more frail at the end of your life, would destroy them.

   14. DSDavid Senra56:36

       Yeah, I- I- I'm glad you brought that up because one of my favorite ideas that I've ever come across from any book, and it ties to the last part of the- your sentence there, was (clears throat) Jeff Bezos has this thing called the Regret Minimization Framework, which is like this nerdy way to just- to describe how can you get to the end of your life with the least amount of regrets possible, right? And so he is in ... People, like, don't, like, they- they know, like, I think it should be obvious that Jeff's super, like, super smart, but he's like genius-level smart. And so even way before he started, uh, Amazon, he's working for this quantitative hedge fund in, uh, New York City called D.E. Shaw. Uh, or, yeah, I think, I can't remember if the- the guy, the founder is D. E. Shaw or if the actual fund is D.- uh, D. E. Shaw. But anyways, it's run by this, like, quantitative brilliant billionaire, right? Jeff is making a ton of money. He's got this beautiful apartment, uh, in Manhattan, and he sees, he's doing research for something, he sees how fast the internet's growing. This is like the mid 19-, this is like '95, '96. He's like, "Oh my God." He's like, "Things just don't grow this fast. Like this is a once-in-a-lifetime opportunity. I want to take part of this." And so he can't get this idea out of his mind and, but all the external things is like, "No, Jeff, you're already successful." Like, like, "If you can't leave now, what about your bonus?" And so he's like, he goes to his boss and they go for a long walk in, um, in, uh, Central Park for like two or three hours 'cause his boss is trying to talk him out of not quitting. 'Cause in, the code name for what turns into Amazon inside the hedge fund was c- called The Everything Store. Like that is why the biography by Brad Stone is called The Everything Store. And so Jeff- Jeff's like, "I- I think I wanna take a risk, quit a job while I can still do this, and, like, try to play a role in what I feel is gonna be, uh, a life, like, uh, uh, an Earth-changing time," which is like the birth of the internet, which obviously has changed our entire life. The idea of me and you even connecting could not have happened without the internet, right? And so they take a long walk. He's like, and his- his boss is like, "You know, you can stay here. You're gonna be rich. You- you have this big bonus." And he's like, "I'm gonna go home and sleep on this." And he says th- he's like, "I struggled with this decision until I figured out the Regret Minimization Framework." He's like, "27 or 28-year-old Jeff Bezos is not capable of making this decision, decision, this decision. But 80-year-old Jeff Bezos is capable of making this decision." So he, he tried to view his life looking back. And he's like, "When you're on your deathbed in your 80s or hopefully 90s or whatever it is, you're surrounded by the ones you love. You're gonna be telling yourself the story of your life. And that person is not gonna say, they're not gonna give two shits that you- that you quit your job and you don't get your quarterly bonus, right?" But what they would give a shit is like, you had a chance to play a role in the birth of the internet, right? The way Jeff thinks about internet is the way I think about podcasting and I think, like, you also as well. It's like, we're at the very beginning of an industry. We have a role to play here. Like, this is amazing. I don't want to do anything else, I'm focused on this. And so he goes, "Once you make, once you look at it in that- in that, once I looked at it in, uh, that framework," he's like, "the decision was easy." He's like, "Jump. Try to do it. If you try and fail, 80-year-old you is like, 'Good, at least you got off your ass. You took a goddamn risk for once in your life, good. Try again.'" But 80-year-old you is like, "Oh, you were comfortable. Like you were young and smart and had ..." He had no kids at the time. He wasn't even married yet. I think- I think they eventually got married 'cause she, uh, she, uh, MacKenzie winds up quitting and driving cross-country with him. Now, how does that tie with what you just said? 'Cause that makes sense, right? But then what happens? He- he starts out with his wife. His wife knew him before he was Jeff Bezos of Amazon. She helps him build the company. That's why she got this huge divorce settlement. But now you fast-forward, he's one of the richest people in the world. He's an empire builder. Complete, like, alpha nerd, right? Genius guy. Then he lets his family fall apart. Now, you and I will never know, like maybe he's like, "Hey, I don't care. I just want to sleep around. I can get the best women in the world or whatever." Maybe that is what makes him happy. I don't know. But I would- I would love to, in like these quiet moments, does he regret destroying his marriage or not?

   15. CWChris Williamson1:00:24

       That would be a great question to ask. The price that people pay to achieve the things that everybody else desires is a question that endlessly fascinates me. I'm always thinking about it. I'm always thinking about it.Let's

9. 1:00:35 – 1:16:57

   The Most Ruthless Entrepreneurs

   1. CWChris Williamson1:00:35

      go to the other end of the scale. So we've spoken there about some examples of people that have tried to create more holistic, um, views of success. Who are some of the most ruthless, ambitious, just stone-cold killers that you've studied?

   2. DSDavid Senra1:00:56

      Steve Jobs, to me, is the greatest entrepreneur to ever do it. And in, like, i- a lot of this is subjective, like, but if you had a Mount Rushmore of history's greatest entrepreneurs, he's gotta be on there. He's like at lea- you, you can't have four other people on there that's not him, right? And the sad part about the fact that he was, um... I li- I just liked the, like, the quality of his thinking, the clarity of his thinking, the fact that he started the company ... The first sale Apple ever made was made barefoot. Like, he walks into the Byte Shop in Palo Alto, or maybe Menlo Park, can't remember exactly where it was, and he makes Apple's first sale, and he doesn't have shoes on. He doesn't take baths. He, like, he was completely, like, an inner scorecard person. There's this idea that I learned from, um, reading, uh, th- this book called The Snowball, which is like a most well-known biography of Warren Buffett. And he talks about, he's like, "It's very hard to have a, a happy life if you, if you have an outer scorecard as opposed to an inner scorecard." So what does that mean? And he compares his growing up. He had a real bad relationship with his mom, who was all outer scorecard, and yet his dad was his hero. All inner scorecard. And what inner scorecard means is, like, you're doing what you want to do based on how you feel about it, right? Not his mom would make decisions. Should I do, if I do this, what will other people think? And so I also like the writing of Tim Urban from Wait But Why?, and he really helped crystallize this. He has this post called, like, The Mammoth or something like that. But essentially, it just proves, it's like, the idea that other people are thinking about you is a myth. People think about themselves, and he has, like, these little stick drawings. And it's like, in our mind, it's like we're in the center, and all these people are looking and pointing at us, right? And then he goes, "This is what you think, and this is what happens." Like, you're still in the center, but everybody's, like, looking at their phone or they're, they're worried about other stuff, right? And so that, to me, it's very, very freeing. And so he said his dad made decisions based on how he truly thought. He didn't care what the outside world thought, which I think is extremely, um, like I- I think, like, is extremely, uh, important, uh, and I think it is a skill to develop. And his, his, his, it destroyed, like, his relationship with his mom, the fact that she wanted to, him to make decisions based on, like, what will other people think. He's like, he didn't even want to go to college, which was crazy at the time, 'cause his dad was a congressman and everything, and he's already owning businesses. He owned, like, a farm. He had a bunch of stocks. This is like a young Warren Buffett. He's like, uh, he's like read 100 books on investing. He's like, "What, what else am I gonna learn?" And so he, they wound up making him go to, uh, uh, go to school or whatever the case is. But what I like about Steve is, like, Steve is all inner scorecard. He's like, he had one obsession. "I'm going to make insanely great products." That is a term that he says, "insanely great products". He says that when he's, like, 20. He says that when he's 30, 40, he says it right before he dies. That's how he describes the iPad, way before he dies. And so what I respect about him is just, like, how the hell do you make great world-class products in the '70s, the '80s, the '90s, 2000s, and in 2010 right before he died, right? Um, but what's sad is, I respect him for what he did professionally. But he says in this au- this biography that he's working on as he knows he's dying with Walter Isaacson, and at the end, I recommend, even if you haven't, even if you don't want to read the whole book 'cause it's giant, read the last page, pa- last chapter, or maybe last two chapters, where he describes his legacy. So it's like why he did what he did, and then he describes why he's spending hi- some of his final days working on a book. And he said something that was devastating to me. He's just like, "I wasn't around much, and I want my kids to know why I did this." And so, like, that completely ... He's, his ruthlessness was not, "Hey, I'm gonna be the richest person in the cemetery." He doesn't give two shits about that. He's like, "I'm gonna make world-class products, right? And I'm gonna spend all of my time and energy on my world-class products." And as a result, he's sac- uh, where is that time coming from? Time is coming from taking care of his health, spending time with his wife and his kids. Maybe he spent time with his wife. I, uh, th- that part I don't know, but, like, he definitely missed out on, you know, some part of his, his kids' life.

Episode duration: 1:47:52