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Tim FerrissTim Ferriss

David Senra — How Extreme Winners Think and Win: Lessons from 400+ of History’s Greatest Founders

David Senra is the host of the Founders podcast. For the past nine years, David has intensely studied the life and work of hundreds of history’s greatest entrepreneurs. His new podcast, David Senra, showcases conversations with the best-of-the-best living founders and extreme winners. This episode is brought to you by: Cresset family office services for CEOs, founders, and entrepreneurs: https://cressetcapital.com/tim Our Place’s Titanium Always Pan® Pro using nonstick technology that’s coating-free and made without PFAS, otherwise known as “Forever Chemicals”: https://fromourplace.com/tim AG1 all-in-one nutritional supplement: https://drinkag1.com/tim *** David Senra: https://davidsenra.com/ [00:00:00] Coming up [00:32] Brad Jacobs [01:52] Rare positive archetypes [05:26] Michael Dell [06:11] Negative self-talk, excellence, and its ripple effects. [07:54] Jensen Huang [08:24] Dan Carlin’s Hardcore History. [09:28] Derek Sivers [10:34] Learning equals behavior change, not memorization. [11:20] Jeremy Giffon insight: biographies as substitute mentors. [13:45] Podcasting as “relationships at scale.” [14:04] Coping with trauma and breaking cycles. [15:33] Note-taking process [24:44] OCD tendencies and love of doing things the hard way. [30:24] A family falling out and the randomness of student housing. [34:38] David’s introduction to my work during his MySpace-era college years. [35:42] Podcasting influences: Jocko Willink, Kevin Rose’s Elon Musk interview. [38:34] 5+ years of obscurity before breakthrough. [43:41] Patrick O’Shaughnessy’s endorsement sparks growth. [49:34] Edwin Land [51:23] Lessons from Sam Zell, Jay Pritzker, and William Zeckendorf. [57:29] Edwin Land’s philosophies: Differentiation and doing to excess. [58:52] Entrepreneurial archetypes and conflicting advice. [01:00:25] Daniel Ek [01:05:21] Further founder archetypes [01:08:12] Anti-business billionaire? [01:14:35] Advice from “shark” Michael Ovitz [01:17:13] The hands-on approach of practical founders [01:18:14] Doing one thing relentlessly. [01:18:36] “This can’t be my life” as a powerful motivator. [01:21:40] Low introspection as a common trait among founders [01:24:33] Robert Caro. [01:27:15] James Dyson’s persistence vs. the risk of blind stubbornness. [01:28:56] Todd Graves (Raising Cane’s) as an example of relentless focus on one idea. [01:36:10] Considering trainable vs. non-trainable attributes [01:40:19] Charlie Munger’s library. [01:43:32] Dealmaking lessons on Eddie Lampert’s superyacht. [01:50:30] David’s obsessive craftsman approach to podcast creation. [01:52:20] Why David decided to begin a second podcast. [01:57:00] The benefits of cultivating a purposeful aloofness about current events. [02:02:54] New show frequency/dynamic and how David plans to balance the burden of running two shows. [02:08:30] Rockefellers “secret allies” strategy [02:10:28] Chris Hutchins: The mad scientist of podcasting? [02:10:58] Working with Rob Mohr and Andrew Huberman. [02:17:18] Does David worry that the extra workload will disrupt his lifestyle? [02:26:13] Impact vs. happiness. [02:28:27] Playing the status game when your heart’s not in it is for suckers. [02:26:05] Travel observations and the rarity of truly unique experiences. [02:38:10] Books as philosophical operating systems. Sign up for "5-Bullet Friday" (Tim's free weekly email newsletter): https://go.tim.blog/5-bullet-friday-yt/ Follow the Tim Ferriss Podcast: https://tim.blog/podcast/ Visit the Tim Ferriss Blog: https://tim.blog/ Follow Tim Ferriss on Twitter: https://twitter.com/tferriss/ Follow Tim Ferriss on Instagram: https://www.instagram.com/timferriss/ Like Tim Ferriss on Facebook: https://www.facebook.com/TimFerriss/

David SenraguestTim Ferrisshost
Sep 24, 20252h 42mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 0:32

    Coming up

    1. DS

      Edwin Land says, "My personal motto is very personal. It may not apply to anybody else or any other company, but is don't do anything that someone else can do."

    2. TF

      Mm-hmm.

    3. DS

      The importance of differentiation, I'm shocked at how few people understand how important it is. Dyson.

    4. TF

      Mm-hmm.

    5. DS

      Dyson's whole thing is like it has to be different even if it's worse.

    6. TF

      Mm-hmm.

    7. DS

      It should be different.

    8. TF

      That's interesting.

    9. DS

      He demands difference. He's got a very fascinating business philosophy. The, Dyson's mind's incredible. And then the other thing is he knows, 'cause he dropped out of Harvard twice, he goes, "There's something they don't teach you at Harvard Business School, that anything worth doing is worth doing to excess."

  2. 0:32 – 1:52

    Brad Jacobs

    1. TF

      So who is Brad Jacobs?

    2. DS

      So Brad Jacobs is I think the only person in history to start eight separate billion-dollar companies. So a lot of people like on the, the, the West Coast, you know, in tech scene, they don't really know who he is-

    3. TF

      Yeah

    4. DS

      ... 'cause he's just been an East Coast guy his whole life, but he started his first company when he was, like, 23. He's 68 years old.

    5. TF

      Mm-hmm.

    6. DS

      He is by far the most energetic person I have ever been, like, been around.

    7. TF

      Mm-hmm.

    8. DS

      And he wrote this book called How to Make a Few Billion Dollars.

    9. TF

      What are some of his companies? What, what industries and so on?

    10. DS

      So he does, like, he's like the roll-up king.

    11. TF

      Yeah.

    12. DS

      So, like, he'd roll up, like, logistics companies and trucking companies, and now he's got a massive one he just took public that's doing, like, building supplies.

    13. TF

      Mm-hmm.

    14. DS

      And so, like, you know, you, you, early in your career you might roll up, like, a $5 million company or a $20 million company. His first acquisition I think was, like, $9 billion. So he's like-

    15. TF

      [laughs]

    16. DS

      He just gets progressively, like, bigger and bigger and bigger.

    17. TF

      Mm-hmm.

    18. DS

      But what I find interesting about him is usually when you study, like, extreme winners, and he's obviously an extreme winner, what motivates them is, like, kinda dark.

    19. TF

      Mm-hmm.

    20. DS

      Like issues with their father.

    21. TF

      Yeah.

    22. DS

      Uh, some kind of insecurity, they don- never felt good enough. They grew up poor, and they, they felt they were born in, like, the wrong place. Brad does it out of love. He's got no negativity. He's just a very special human being, and the fact that I get to text him and call him and go to his house is insane. He's just an amazing

  3. 1:52 – 5:26

    Rare positive archetypes

    1. DS

      human being.

    2. TF

      There's another legend who defeated roulette and then went on to beat the market, Ed Thorp, probably another exception.

    3. DS

      The exception.

    4. TF

      The exception-

    5. DS

      Yeah

    6. TF

      ... where he did not eviscerate his personal life in the quest for business mastery.

    7. DS

      Yeah, I don't think anybody's mastered life clearly as much as Ed Thorp did. Your interview, your two interviews that you did with him were incredible.

    8. TF

      Thank you. Yeah, that was such a moment of gratitude to have the chance to interview him, especially because he is so, so sharp at his age. Can't recall his exact age right now, but-

    9. DS

      He was, like, 89-

    10. TF

      Yeah

    11. DS

      ... or something like that.

    12. TF

      That's the, if you want a holistic figure to consider emulating, Ed Thorp would be on a very, very, very short list.

    13. DS

      I can think of three out of 400.

    14. TF

      All right. Who are the, who are the three?

    15. DS

      Ed Thorp's at the top. Sol Price, who's the one that invented essentially, like, the warehouse model, like Costco. Like, Jim Sinegal was mentored by Sol Price when Jim Sinegal was, like, 18.

    16. TF

      Mm-hmm.

    17. DS

      So Jim Sinegal, founder of Costco, you know, went on, built one of the greatest companies in history, and he has this great line in Sol Price's autobiography, and Sol Price's son wrote his biography. And people are like, when Sol died, he's like, "You must have learned a lot from Sol." He goes, "No, I didn't learn a lot. I learned everything."

    18. TF

      [laughs]

    19. DS

      "Everything that I know, I learned from this guy." So Sol Price, same thing, good husband, good father, didn't chase after m- more money at the expense of other areas of his life after he already had enough money, which is what Ed- Ed Thorp turned down so much, hundreds of millions, if not billions. He could've, like, collected. He's just like, "I already have more money than I can ever spend. Like, why would I do that?" And then I would say Brunello Cucinelli.

    20. TF

      How are those examples different? Well, you should [laughs] explain for folks, I mean, look, everything I'm wearing I got for free. So you should explain to people, I did not know the last name you mentioned until a few years ago.

    21. DS

      Yeah.

    22. TF

      'Cause I won't dox him, but Tony, my friend Tony, is basically [laughs] covered in Brunello. Who is this?

    23. DS

      So Brunello Cucinelli wrote this, I don't even know the name. I've read the book. It's, like, something about Salomaio. Essentially he sells $5,000 [laughs] sweaters.

    24. TF

      Yeah.

    25. DS

      He sells sweaters that were more than my first car.

    26. TF

      Yeah.

    27. DS

      But he grew up in, like, very rural Italy, and then everybody at the time, there was essentially the hollowing out of his community. Everybody had to move to the cities. He is a very soulful dude. Brunello essentially works, he bounds his life where it's like you work 9:00 to 5:00. You're not allowed to, like, send an email to the, the company after 5:00. You have to, like, take a break for lunch, and they have this, like, great Italian food, and then he spends his nights reading and then going on long walks and then sitting in the cafes in this, like, little town that he essentially, like, rebuilt and reinvested in, and he likes having cappuccino and, like, debating philosophy. He's just, like, a real soulful dude. Now, the, the one criticism people have is like, yeah, that business model works when you have, you know, 70% margins and your sweaters are as much as a Honda Civic, [laughs] you know?

    28. TF

      Yeah.

    29. DS

      But I don't care what people do. He's just very intentional.

    30. TF

      So let me come back to this question of clean fuel versus, let's call it dirty fuel, and th- there's a lot in between, so I don't wanna look at it in a totally binary way. But why do you think of the, say, 400-plus that you can only call to mind three or four, Ed Thorp, Sol Price, Brunello Cucinelli, Brad Jacobs? Why are there so few who seem driven in that particular, let's just call it positive way, or that they can pursue business excellence without having a lot of collateral damage in their personal lives? What do you draw from that? And look, maybe these are just different animals, and out of the box, these four are just fundamentally different from the other 396 or so. But what is your take on that thin slice of the total?

  4. 5:26 – 6:11

    Michael Dell

    1. DS

      I would add another one to the list. You've also interviewed him, Michael Dell. Recently I've spent, like, hours and hours with him. We had, like, a five-hour dinner, and then I just recorded a two-and-a-half-hour conversation with him for the new show.

    2. TF

      Mm-hmm.

    3. DS

      He is in love. His is very positive. Now, he has a big fear of failure-

    4. TF

      Mm-hmm

    5. DS

      ... which almost I think me and you probably share this, is like, what are you, like, I think, I, I won't speak for you. I wanna ask you actually. Like, I am way more afraid of failure than, like, I love winning.

    6. TF

      I mean, that's true for everyone I know-

    7. DS

      Yes

    8. TF

      ... who wins a lot. I don't think I can think of a single exception In terms of someone who celebrates the wins as much as they punish themselves for the losses.

    9. DS

      Yeah.

    10. TF

      I'm not saying that's a good thing, I'm just saying that's pattern matching.

  5. 6:11 – 7:54

    Negative self-talk, excellence, and its ripple effects.

    1. DS

      But even now, with all the success that you've had, like is your inner monologue still negative?

    2. TF

      I mean, there's a lot of negative. I'm working on that. I look at some of the, I don't wanna call them maxims, but, uh, you've quoted the, I think it was the founder of the Four Seasons.

    3. DS

      Yeah. Excellence is the capacity to take pain.

    4. TF

      Right.

    5. DS

      [laughs]

    6. TF

      And there may be some truth to that, but I, I feel like it's very risky for me to take something like that and wear it as a marching order for life because I already tilt in that direction. And not all pain is productive.

    7. DS

      Mm-hmm.

    8. TF

      Right? [laughs] And I think for me, when you are already tilted in that direction where you believe if there isn't pain, if there isn't some degree of suffering and you're not trying hard enough, it's very easy to become a hammer looking for nails.

    9. DS

      Mm.

    10. TF

      And that can have a lot of repercussions for your relationships also.

    11. DS

      For sure.

    12. TF

      And if your self-talk is negative, at least in my experience and what I've seen in a lot of my friends and peers and founders, very often you end up having a similar type of dialogue with people around you, and that can have huge repercussions. So that doesn't give anyone a neat, tidy silver bullet of an answer.

    13. DS

      Yeah.

    14. TF

      But yeah, the negative self-talk, there's a place for it, but like the nuance to me matters a lot, right? If it's like, "You're a piece of shit, you always do X, why don't you do Y?" And that has a good outcome, I would still wanna refine the process.

  6. 7:54 – 8:24

    Jensen Huang

    1. DS

      I read this biography of Jensen Huang, which is fascinating, 'cause it's like right after one of the best quarters in Nvidia history, he said that, he [laughs] starts this meeting and he says, "I woke up this morning and looked in the mirror and said, 'Why do you suck so much?'" [laughs] So he's-

    2. TF

      Yeah

    3. DS

      ... definitely driven by-

    4. TF

      He's hardcore.

    5. DS

      Oh, he's very hardcore.

    6. TF

      He, he is. He's hardcore. He's hardcore. So I guess what I'd also like to ask you is about not necessarily the people you study.

    7. DS

      Mm-hmm.

    8. TF

      And hopefully you take this as, as a compliment. It's intended like the highest compliment,

  7. 8:24 – 9:28

    Dan Carlin’s Hardcore History.

    1. TF

      but when people ask me about you and they're like, "So what's the story? Like why do people like his stuff?" And I'm like, "Well, you know, I, I can only really speculate," but I feel like you are, in a way, what Dan Carlin did with Hardcore History, like you do for business. And Hardcore History is my favorite podcast of all time.

    2. DS

      I, I think Dan Carlin's the greatest podcaster to ever live. The reason I do a solo history show is because Dan Carlin. I've given away his back catalog.

    3. TF

      Yeah.

    4. DS

      I wish he would change his business model. [laughs]

    5. TF

      It is a bit janky.

    6. DS

      Yes. [laughs]

    7. TF

      But like if you wanna just listen to like the greats, I mean, The Wrath of the Khans.

    8. DS

      Blueprint for Armageddon. Wrath of Khans I think is the best podcast series ever created-

    9. TF

      Yeah

    10. DS

      ... in my opinion. Blueprint for Armageddon, like just everything. I've listened, he only has like 55 episodes. He was doing it for like 15 years. I just, I go to... I fall asleep at night. Right now, last night I fell asleep listening to his new one. It's not even new, it's like six months old, 'cause he n- never releases any episodes. Mania for Subjugation Part Two, about the relationship between Alexander the Great and King Philip.

    11. TF

      Amazing.

    12. DS

      He just-

    13. TF

      Yeah

    14. DS

      ... puts me to sleep. He is the greatest.

    15. TF

      So,

  8. 9:28 – 10:34

    Derek Sivers

    1. TF

      [laughs] so the, you know, the reason that I, I mention that is like I f- I feel like I've learned so much from Dan Carlin. I've learned so much from your episodes. I'm curious, though, as, and I, I know another person you're a fan of, Derek Sivers, who-

    2. DS

      Yeah

    3. TF

      ... I've known I think since 2007. Amazing entrepreneur. People can look him up. I'll give the one-liner, which he's sort of this like philosopher king, programmer entrepreneur who started companies, gave the vast majority to a charitable trust to fund musical education. At one point was the ringleader in a traveling circus, played guitar and sang at like a pig state fair, and has just crafted the most [laughs] unusual and Derek life for himself, and given his family permission to do the same for themselves. Really a true original thinker who also shows it in his actions, and this is where I'm going. So Derek has this line which is along the, the, the... I, I may be paraphrasing it slightly, but the gist is, you know, if more information were the answer, we'd all be billionaires with six-pack abs.

  9. 10:34 – 11:20

    Learning equals behavior change, not memorization.

    1. DS

      Yeah.

    2. TF

      So what do you see or surmise about people who make the leap from listening to your podcast about all of these icons and people who have not just, you know, once you're lucky, twice you're good, but in some cases they built, you know, eight-

    3. DS

      Yeah

    4. TF

      ... billion-dollar companies, or in that case, it might come back to the acquisition kind of roll-up archetype. So the people who make the leap from ingesting information to actually implementing and those who don't, like what's, what's the missing piece in the middle?

    5. DS

      The way I think about it, the, the maxim I've made for myself on this is like learning is not memorizing information, learning is changing your behavior. And so if you didn't change your behavior, you're, this is just all mental gymnastics for you. You know? You're just wasting your time. And so what I'm trying to do, I didn't even understand what I was doing.

    6. TF

      Mm-hmm.

  10. 11:20 – 13:45

    Jeremy Giffon insight: biographies as substitute mentors.

    1. DS

      I had to have as m- many, happens in many cases, like somebody outside of you seeing what you're doing actually gives you what w- like what this whole thing is about. So I have a good friend of mine, his name's Jeremy Giffon, and he's really quick-witted, and he has a way to like condense ideas really well. And we're just walking around, taking a walk in Miami Beach one day, and he's like, "Oh yeah, it's pretty obvious like what this whole thing is." And I didn't even think he was thinking about it, right?

    2. TF

      Yeah.

    3. DS

      And I was like, "What do you mean?" And he's just like, "Oh, you never had any positive influences. You didn't have any mentors. And so if you, you take somebody like you who's like psychopathically driven and really has an obsessive personality, like that's what this whole thing is. You're just reading book after book after book to try to find the path, to try to find the answer, and to try to find the way out." And I felt like naked [laughs] when he said this.

    4. TF

      Yeah.

    5. DS

      I'm like I think he's right. I think he's right. And so for me, like I'm definitely not just reading. Like, I've been taking all these ideas. The unfair advantage I have is like I have one-sided conversations with history's greatest entrepreneurs, right? So like every week I sit down and read another biography, and then because I like to talk, this is good because I, I have to shut up. I can only listen because this is what I think it is. That's why I think reading a biography is like a one-sided conversation.

    6. TF

      Yeah.

    7. DS

      And then I take that, and I would be doing this even if I didn't record it, but then sitting down once a week and condensing my thoughts, right, and reacting to it-

    8. TF

      Mm-hmm

    9. DS

      ... turns into an act of service, right? So then I take the ideas. I'm like, "Oh, that's a good idea." I'll take that and apply it to my business, which is the podcast, and it keeps getting better and better. I was like, "Oh, these ideas work, so I'll keep doing this." And then now what has happened is greats... The people that are trying to be great have studied great people that came before them throughout human history.

    10. TF

      Mm-hmm.

    11. DS

      You know, Caesar was studying Alexander, and like Steve Jobs was studying Edwin Land, and Edwin Land was studying Alexander Graham Bell. And everybody, if you're interested in American entrepreneurship, it all kinda goes back to Benjamin Franklin.

    12. TF

      Mm.

    13. DS

      Like, everybody looks backwards. Like, that guy or that woman was great. How did they do that? And so that is an enduring, you know, part of human nature that'll never change. It's gonna happen while we're alive. It's gonna happen 1,000 years from now. And so what I didn't understand what I was doing is that you put it out into the world, just like your work is like a tuning fork, right?

    14. TF

      Mm-hmm.

    15. DS

      Then the people that are really great also do this, and they have a deep love of history. And so if you look at the people that I've been talking to from the new show that's not even released yet, they came because they're fans. They're in the audience.

    16. TF

      Mm-hmm.

    17. DS

      And it's just like the, the parasocial relationship people have with podcasts.

  11. 13:45 – 14:04

    Podcasting as “relationships at scale.”

    1. DS

      I'm close to the people at Spotify. Spent, been to Stockholm twice in the last six months, and I was talking to the head of business at Spotify. His name's Alex. We were talking for two and a half hours, like pretty animated, and I was like, "I'm not building a media company."

    2. TF

      Mm.

    3. DS

      "I'm building relationships at scale." And he's like, "What? You say that again." I go, "What a podcast is, is building relationships at scale."

  12. 14:04 – 15:33

    Coping with trauma and breaking cycles.

    1. DS

      I have... This is the first time we've ever met.

    2. TF

      Yeah.

    3. DS

      Now, we could, we should talk about how I found you. I found you on MySpace. I'm gonna tell you that real quick.

    4. TF

      Oh, my God. [laughs]

    5. DS

      But like the reason we... And we'll go to like the influence that you played on having founders. It's just like, but I know who you are. Like, we could sit down and talk for eight hours because I know you. There's no possible way I can consume all of your books and, I don't know, 600 hours of your podcast and not know Tim. You can't act for that long.

    6. TF

      Right.

    7. DS

      And so what I didn't understand is like, oh, this other path of me trying to find good information, valuable information. Like, I came from a family. It was like, "Oh, I'm the first to graduate college. That's nice." No one even graduated high school in my family.

    8. TF

      Yeah.

    9. DS

      Like, there's no reading. There's no self-improvement. The only thing my family read is the Bible, and like that can be taken to a crazy extreme. My mom-

    10. TF

      You also didn't go to prison.

    11. DS

      Yeah, exactly. The first... And my grandfather, my... I shouldn't even say this, uh, publicly anymore. You have a big podcast. I, uh, I would say stuff on small podcasts and forget-

    12. TF

      [laughs]

    13. DS

      ... that things get bigger later on. So I say crazy stuff that I should not be saying, but whatever. We're too late now. But yeah, my grandfather, my father, my brother. Like, I remember being in high school and hearing bang and five guys at 5:30 in the morning come and grab my brother, and I don't see him for four years. Like, that's a fact. So my point being is then I'm like, oh wait, I put this podcast out, and then it attracts the same people that are in the books. And then, you know, the fact that I could spend five hours with Michael Dell, and he tweets about the podcast, and he LinkedIn's about it, and he's just giving me phenomenal advice-

    14. TF

      Mm-hmm

    15. DS

      ... with no... And then we obviously, we recorded our conversation, but before that, they just wanna help you because they got value from

  13. 15:33 – 24:44

    Note-taking process

    1. DS

      that.

    2. TF

      So let me pause you for one second, just because I wanna go back to the note-taking and then converting that into some type of action because you've done that. I mean, you're, you're hitting, and you've had a number of these, but inflection points where now you can sit down with some of these icons and have these extended conversations. Even if you did not have that direct access, maybe your process with the note-taking wouldn't change. I'm just curious how you read one biography or multiple biographies on a person and what the actual note-taking process looks like. I'll volunteer what I do a lot. I use Kindle, not for the convenience of the device, although that is convenient, not because I can listen on Audible or actually do it through the Kindle app and then stop and highlight things, which is also why I use it, but the highlighting overall is the reason.

    3. DS

      Yeah.

    4. TF

      And then exporting or using something like Readwise in addition to synthesizing my highlights, and I believe you also use, uh, Readwise quite a bit. I'm not sure if you still use it.

    5. DS

      Oh, yeah.

    6. TF

      But what does your process look like? And I know for instance like Maria Popova, who's this like voluminous, prodigious genius of a writer, used to be Brain Pickings. It's the Marginalian now. She has a very particular process for like synthesizing and, and putting everything together. How do you do that?

    7. DS

      So I actually think I'm gonna sit down and make an episode about how I make these. There's actually a, an older idea that I just went through when I reread James Dyson's autobiography, both of them actually. But the first autobiography I read like five times. The second one, I think this is the second or third time I read it. One of the genius things that he did, you know, when no one knew who he was, Dyson wasn't a thing. Like, now it's one of the most valuable privately held companies in the world. You walk into a retail store. He had one product in one market at the time, and you see, you know, I wanna buy a vacuum cleaner. Five of them kinda look the same, and then you have this like alien-looking thing at the end. But then what he said, he's like, "Hey, what is the advantage I have? I'm going against all these like huge multi, you know, national conglomerates, and I'm just some bloke that cares about vacuum cleaners in this remote part of England." And he convinced all the retailers to let him write a story on a little leaflet, and they would hang it on the handle of the Dyson, right? And it tells a story, it's like two, 200 or 300 words, of who made it, why they made it, why they love it so much, and why you should buy it.

    8. TF

      Mm.

    9. DS

      People buy stories.

    10. TF

      Yeah.

    11. DS

      And so what I was saying is like that's not the first time I came across that idea. You go back to the early 1900s, and there's this guy named Claude Hopkins. I am always interested. You are-

    12. TF

      I read-

    13. DS

      Scientific Advertising?

    14. TF

      Yes, in the very beginning.

    15. DS

      I'm always interested who influences the influencers.

    16. TF

      Right.

    17. DS

      Right?

    18. TF

      Yeah.

    19. DS

      So let me give you an example.

    20. TF

      God, I haven't thought of that name in so many years.

    21. DS

      I have so much shit on this guy.

    22. TF

      Claude Hopkins.

    23. DS

      So I became obsessed. We, we were talking before we recorded that we both Really, I, well, I won't speak for you, love and admire, and mine is borderline idolize Charlie Munger.

    24. TF

      Right.

    25. DS

      If I could only learn from one person for the rest of my life, if I could say, "Hey, you can only read this guy's words. Pick one person," I'm picking Munger. I just love everything about him, and the idea that I got to meet him is insane. Like, absolutely insane. So when I'm reading about Munger and Buffett, I'm like, "Man, these guys are really genius." I didn't know anything at this time. This is, like, 10 years ago. And I'm like, "These guys are genius." And then they kept mentioning this guy named Henry Singleton over and over again. And they, they will tell you, ev- if you just, if you admire somebody, what I think is hugely important, go... They will tell you who influenced them, and then you have to go and read about these people, and then you'll find who influenced them, and you realize that the ideas didn't start with them. They don't start with us. They can't die with us either. You have to push them forward down the generations. And so I'm like, "Oh, this guy's interesting." Charlie Munger said that the smartest person he ever met was Henry Singleton. He's best friends with Buffett. Like, Buffett's obviously... [laughs] I was... How did he say that? And then Buffett says that it's a crime that business schools don't study Singleton. That's a hell of a lang- like, that's... Right?

    26. TF

      Strong language.

    27. DS

      Strong language. And so then you start reading, and I'm like, "Oh my God, the, the ideas that I thought were Buffett and Munger's were Singleton's." And so you see this over and over again. I was obsessed. Another guy that Buffett introduced me was David Ogilvy. David Ogilvy I think is one of the best writers I've ever come across. Why is Buffett calling this guy a genius? Who is this guy?

    28. TF

      I read Ogilvy's stuff at the same time that I read Hopkins.

    29. DS

      So, 'cause if you read Ogilvy, he, what does he talk about? He's like, "That's the genius. I'm not the genius. I'm just regurgitating Claude Hopkins' work." And then he tells the story of Albert Lasker, who made more money... There's all these, let's call them a dozen great advertising agency founders.

    30. TF

      Mm.

  14. 24:44 – 30:24

    OCD tendencies and love of doing things the hard way.

    1. DS

      Okay. So then, uh, I'm writing it down, and then like, you know, I might have three sentences, but the Post-it Note's three by five.

    2. TF

      Mm-hmm.

    3. DS

      So I have to cut it. It has to be clean.

    4. TF

      Yeah.

    5. DS

      It has to look good.

    6. TF

      Yeah.

    7. DS

      Like, there's a beauty to it. Like, I'm irrational, like crazy when it comes to this stuff. I... This is why I think I picked up on your work right away.

    8. TF

      Yeah.

    9. DS

      'Cause I see a fellow n- nutcase and obsessive.

    10. TF

      [laughs] Yeah.

    11. DS

      Where like I hand edit now-

    12. TF

      Mm

    13. DS

      ... my transcripts.

    14. TF

      Mm-hmm.

    15. DS

      So everybody's like, "You should outsource it to AI. You should outsource it to India." No, I have to touch it. I have to feel it.

    16. TF

      Yeah.

    17. DS

      I have to like... I just love it. I'm not doing it to do it quicker. The har- I like what Jerry Seinfeld says, "The hard way is the right way." I like the hard way. This also goes back to c- obviously have some kind of like dark thing driving me, which w- we can dive into if you want. But, so then you go through the entire book, right? And so then it's, I have to take pictures of it-

    18. TF

      Mm-hmm

    19. DS

      ... into the Readwise app, 'cause you, you do it the smarter way.

    20. TF

      All right.

    21. DS

      Kindle will just automatically go to Readwise.

    22. TF

      Well, I still use physical. I'll explain. I'll trade. I'll tell you how I use physical.

    23. DS

      You wanna go do it now or you want me-

    24. TF

      Yeah, sure. Don't lose your place.

    25. DS

      I won't.

    26. TF

      All right, you got the scissors.

    27. DS

      Yeah.

    28. TF

      I wanna know about the ruler. Oh, I guess the ruler... Well, I want you to explain.

    29. DS

      Straight lines. It has to be straight.

    30. TF

      Okay. Got it.

  15. 30:24 – 34:38

    A family falling out and the randomness of student housing.

    1. DS

      So I went to like a shitty college.

    2. TF

      Mm-hmm.

    3. DS

      Because I remember, like, when I was in your senior year, but, you know, I went to a public high school, and everybody's like, "Where are you going to school?" And I didn't understand what they meant. I'm like, "The one I can drive to? Like, the one I can, like, go to at night because I have to work during the day? Like, I don't know what you're talking about." Like, there-- You-- I didn't know. I got kicked out of my house when I was 18, and I had to live in student housing.

    4. TF

      Why'd you get kicked out?

    5. DS

      My mom's side of the family has, like, severe mental illness, and just, like, some of the worst people you've ever met, and they just had this belief that you kick your kids out when you're 18. And like-

    6. TF

      I got it

    7. DS

      ... it's just like-

    8. TF

      Out of the nest

    9. DS

      ... it, it's not even that. It's like they, they pick a fake fight, and you have somebody that's very, like, I'm not-- That was a, the point of contention between my mom is she had undiagnosed mental illness for sure. Maybe not schizophrenic, definitely bipolar. Her sister was schizophrenic. And listen, man, as you get older, at the time, I had a lot of anger, like super, a lot of anger, because I didn't understand why they're doing what you're doing, and then you get older, and then you have your own kids. So I went through this crazy thing where, like, I think I, like, hated them even more because when my daughter was born, I'm like, I remember seeing her for the first time, I was like, "I've never loved..." Like, you think you love a woman? No. Enzo Ferrari has this great line that [laughs] it's not, it's impossible for a man to love a woman. He, the only true love he has is for his, his kids, and I understand what he meant. I think Ryan Reynolds said it best where it's like, "I never thought I'd l- love anybody as much as I love Blake Lively, and then she gave birth to our daughter, and as soon as I looked at the daughter, I knew if we were ever under attack, I would use Blake as a human shield to protect that baby." [laughs]

    10. TF

      [laughs]

    11. DS

      Like, it's funny, but it's-

    12. TF

      Yeah

    13. DS

      ... literally, when I heard him say that, I go, "Yes."

    14. TF

      Right.

    15. DS

      "That's it." And so-

    16. TF

      So that makes the memory all the more painful

    17. DS

      ... then I was like, "How do you do this to your children?"

    18. TF

      Yeah.

    19. DS

      And then you get more experience, and then you're like, "Yeah, but, like, imagine you grew up like they did."

    20. TF

      Right.

    21. DS

      Like poor white trash. My grandfather raped all his daughters, including my mom.

    22. TF

      Jesus.

    23. DS

      Raped all-

    24. TF

      Brutal

    25. DS

      ... of his daughters, raped his gr... I didn't know about this till after he died, or else I was, would've been the one to put him in his grave. Raped his daughters, raped his granddaughters. They lived in this, like, shitty house in Indiana with one bathroom that was in the ma- There was two bedroom. She had three sisters. The only bathroom is in my gram... I can't call them grandparents. I hate them with all of my being, in their room. And so if you wanted to go in the bedroom at night, he was a monster. He-- You had-- They would urinate in cups and pour it out the window.

    26. TF

      Wow.

    27. DS

      So again, it doesn't excuse the bad decisions they made and the unhappy marriage my parents had and all this other crap, but it's just like, all right, imagine that. Imagine that. You, y- you destroyed your kids. That person was supposed to protect them.

    28. TF

      Yeah.

    29. DS

      And like, we-- I can't even talk about this, but, so anyways, we would fight a lot, and she'd be alternate, depending on the day, like she'd be either the kindest person in the world or like, like a storm. And so the unfortunate part was when she got diagnosed with cancer, we hadn't spoken six months. So she only survived another, I think, two years. So that means the last two and a half years, I missed what? Like, that's 20%, 25% of her life. And somebody's like, "What were you guys fighting over?" I was like, "The sad thing is I don't remember."

    30. TF

      Yeah.

  16. 34:38 – 35:42

    David’s introduction to my work during his MySpace-era college years.

    1. TF

      You were taking a pause on Readwise and multiple reads, and you're like-

    2. DS

      Yeah

    3. TF

      ... "I gotta tell you how I found you."

    4. DS

      Oh, okay. So again, I'm at a crappy school. It's a state school in Orlando. U- UCF. I almost said UFC like we're-- It's MMA. [laughs]

    5. TF

      [laughs]

    6. DS

      That would've been probably more useful now.

    7. TF

      Yeah. [laughs]

    8. DS

      So UCF, and this is when Facebook was coming out, but Facebook was only at the fancy schools.

    9. TF

      Yeah, right. It was very much at the fancy schools.

    10. DS

      We didn't have Facebook. You know what we had? We had MySpace.

    11. TF

      Mm-hmm.

    12. DS

      And so remember like you'd go and there would be like music playing on somebody's profile? Well, people would list like their favorite movies and favorite books, and I think I was like looking at a girl's profile, and under favorite books it said 4-Hour Workweek. And I'm like, "That's a great title. What is that?" And I immediately ordered it on Amazon, and then I started reading it. Obviously, then that book inspired, I don't know, 25 million people, maybe even more by now. And then I start consuming all your stuff, so like I'd buy all your books. I bought your TV show.

    13. TF

      Oh, I appreciate that. [laughs]

    14. DS

      Like sometimes I'll forget because you go on-

    15. TF

      Yeah, yeah

    16. DS

      ... like whatever, it's not called iTunes anymore.

    17. TF

      Yeah.

    18. DS

      And like I don't buy anything because everything streams.

    19. TF

      Yeah.

    20. DS

      I'm like, "Tim Ferriss right there."

    21. TF

      [laughs] I know. From the Natural History Museum back

  17. 35:42 – 38:34

    Podcasting influences: Jocko Willink, Kevin Rose’s Elon Musk interview.

    1. TF

      in the day.

    2. DS

      So I was obsessed with podcasts. I discovered them in 2010, and before I started mine in 2016, I listened to thousands of them. And you had one that changed my life, which was when you did Jocko.

    3. TF

      Mm-hmm. Yeah.

    4. DS

      And that was 2015, if I remember correctly. And you told him to start a podcast.

    5. TF

      Mm-hmm.

    6. DS

      And I think Rogan told him to, to, to do it as well, and he's like, "Well, if I got these two guys," obviously sh- he's smart-

    7. TF

      Yeah, he's, he's smart

    8. DS

      ... to take the advice. And I started listening to his podcast, and he, he changed format, but in the beginning it was just him doing-- He would read a first-person account, so an autobiography of somebody in combat. And I could not believe what I was hearing. And so what I would do is I'd listen to 100 of his episodes and maybe buy a dozen of the books.

    9. TF

      Mm-hmm.

    10. DS

      So you learn, even on the episodes you don't read the book, you learn so much and you're inspired. And in the books, he kept introducing me to all kinds of crazy stories. And I was like, "Hey A couple months later, and then, uh, obviously, like I'd started reading biographies 'cause your friend Kevin Rose did this excellent interview with Elon Musk we can talk about from 2012, and I was like, "What if I do like Jocko's format?"

    11. TF

      Mm-hmm.

    12. DS

      Right? But I- I'm interested in like four things. I'm interested in reading, history, podcasts, and entrepreneurship. And so if you look at it, it's like it just sits in between those four. And I started doing that, and essentially I was just imitating Jocko. And no one gave a shit for five and a half years. [laughs]

    13. TF

      Wow, what a c- what a wild story. So I wanna dive into that. The interview with Jocko, I owe special thanks to, I think it was Peter Attia who made-

    14. DS

      It was

    15. TF

      ... the introduction.

    16. DS

      He said, "Just trust me on this."

    17. TF

      Yeah, and-

    18. DS

      And didn't he just show up at your house or something?

    19. TF

      Yeah, we, we hung out in San Francisco. I remember exactly which coffee shop we went to, and I made the mistake, I wasn't even thinking properly. I had a camo shirt on, and I was like, "I can't believe I wore a fucking camo shirt-

    20. DS

      [laughs]

    21. TF

      ... to meet someone as legitimate as Jocko Willink."

    22. DS

      Yeah.

    23. TF

      And I was just like, "Oh, face palm." But we ended up connecting. That was his first ever public interview-

    24. DS

      Yes

    25. TF

      ... which is wild.

    26. DS

      One of the best ones ever done.

    27. TF

      Oh, I mean, he really brought the heat as Jocko-

    28. DS

      He's my, he's my alarm every morning

    29. TF

      ... is good at doing.

    30. DS

      He's like, "Get up."

  18. 38:34 – 43:41

    5+ years of obscurity before breakthrough.

    1. TF

      So five and a half years.

    2. DS

      Yeah.

    3. TF

      How do you explain no one giving a shit for five and a half years? In other words, was there something that happened, a decision you made, something that changed things around the five-and-a-half-year mark? Was it a change in technology? Was it-

    4. DS

      No, change in business model

    5. TF

      ... the ecosystem? What happened? Yeah.

    6. DS

      Literally, I was doing nothing different. Change in business model. So you remember podcasting back in there 'cause you were-

    7. TF

      I do

    8. DS

      ... like one of the OGs. And like you had this massive audience, your blog was crazy, like you were huge, and still are.

    9. TF

      Mm-hmm.

    10. DS

      And I was none of those things. I was a weird introvert. I didn't have any social media. I didn't know anything about like the internet. I don't know how to describe. I just would like to read, right?

    11. TF

      Mm.

    12. DS

      And record, you know, a podcast in my kitchen on a $100 microphone. And I remember calling around and trying to figure out like what's the business model here? And everybody's like, "Oh, it's ads." I'm like, "Oh, that's great." And so at the time, there was like these ad networks where essentially they just sell ads for you. And they're like, "We'd love to work with you. You just have to have 50,000 downloads per show." And I go, "What?"

    13. TF

      Yeah.

    14. DS

      "I will never f- 50,000?" It seemed like such a big number. Like you're just like, "That will never, ever happen."

    15. TF

      In the universe of podcasts, that's still a big number.

    16. DS

      Yes, but now, like there's million-

    17. TF

      Right. Sure

    18. DS

      ... like think about how many people listen to Tim Ferriss Show and-

    19. TF

      Yeah

    20. DS

      ... like there's millions and millions of people, you know, like over the course of a year or whatever. So I was like, "Oh my God, that's never gonna happen." And so then you say, "Okay, well, what can you do?" And back then it'd be like affiliate. Remember Audible scaled massively.

    21. TF

      Mm-hmm.

    22. DS

      People don't realize how-

    23. TF

      Oh, sure

    24. DS

      ... big businesses can get on the back of podcasts and how many have-

    25. TF

      Huge

    26. DS

      ... Audible was, it was on every si- it was, Dan Carlin had one ad, and it was an Audible ad.

    27. TF

      It was Audible.

    28. DS

      Yes.

    29. TF

      They were very smart about that. They've been able to change a lot of their economics [laughs] -

    30. DS

      Yes

  19. 43:41 – 49:34

    Patrick O’Shaughnessy’s endorsement sparks growth.

    1. TF

      Yeah.

    2. DS

      The one benefit I had which really kept me going, and I don't think I would've quit anyways, I, I, I really don't think I had any other option. But, um, was that, you know, w- we don't know who's gonna listen to this one.

    3. TF

      Mm-hmm.

    4. DS

      We just see numbers on a screen.

    5. TF

      Right.

    6. DS

      But with a subscription, you see the email address, and the emails were, like, the top founders and top VCs, and I had a very small audience, and one of them was our mutual friend, Patrick O'Shaughnessy.

    7. TF

      [laughs] Yeah.

    8. DS

      And I was a huge fan of Patrick, and I saw, I'm not gonna repeat his e- email address here, but I know what the e... I was like, I saw that come across, and there were so few. Like, I saw [laughs] every single one.

    9. TF

      Yeah, sure.

    10. DS

      'Cause you're getting, like, 10 a day, I don't know, five a day or something like that, paid, and I'm like, "Oh my God, Patrick followed." He didn't know who I was. He didn't know I was a big fan of his. He didn't know anything. I had no followers. I think I had, like, 7,000 followers across all, like, every one of my accounts, and I was, like, trying really hard [laughs] back then. And he goes, "I never find good podcasts to listen to. I think David Senra's Founders podcast is excellent. You should listen to it." And he linked to that one on Estee Lauder, and I could not believe it, 'cause I was like, "Why do I have these mentions on Twitter? What is a mention? Like, I don't get mentions. Like, what is this new thing?" And then I log into my email, and it's just... 'Cause I would... Back then, you would get an email every time you get a new s- paid subscription.

    11. TF

      Mm-hmm.

    12. DS

      And off of one tweet, an endorsement by people tru- This is why, like, you and Andrew are kind of like the male Oprah, and I mean that in the mo- Like, you know how much shit I've bought because you told me that it's good?

    13. TF

      [laughs] Yeah.

    14. DS

      Like, why? Because of the trust.

    15. TF

      Yeah. Yeah.

    16. DS

      That's... People chase numbers. It's like that. You're not chasing numbers. You're chasing trust and relationships. I love what Warren Buffett said, "A brand is a promise."

    17. TF

      Mm-hmm.

    18. DS

      The fact that you guys have such high standards, I've never bought anything like, "What the hell was Tim thinking?" And so that's what makes you so valuable. So Patrick extended that trust to me, where I log into my email, and you couldn't stop scrolling.

    19. TF

      Yeah, that's cool.

    20. DS

      You couldn't stop scrolling, and so I screenshotted that because it was-

    21. TF

      Patrick's a good dude. Very smart, too, invests like the best.

    22. DS

      Yeah. You, you did a excellent episode with him for when you hit your 10-year anniversary, right?

    23. TF

      Oh yeah, 10 years. Crazy.

    24. DS

      I was a huge NBA fan, and one of the... But the person that found me that's been really, really helpful when I had, like, 1,500 listeners is a guy named Sam Hinkie, former general manager of the 76ers. Very, very intelligent, like, intense, and kind of a reclusive guy now. He's really hard to get to. We had talked a bunch, and he's just like, "I really think you have something here. I think what you're doing is important, and I've tried to help you as much as I can." And I knew him and Patrick were friends, and I screenshotted Patrick's tweet. I was like, "Look what your friend Patrick did." Sam didn't say anything. He just put it... And again, Patrick trusts Sam.

    25. TF

      Mm-hmm.

    26. DS

      And Sam's telling Patrick, "This guy's worth your time." He put us in a group chat. He goes, "You two need to know each other." And I was like, "Patrick, I'm a huge fan. I'd love to talk to you." And Patrick doesn't have a calendar. So I was like... He's like, "What about right now?"

    27. TF

      [laughs]

    28. DS

      And I was like, "Well, let me look at my calendar." Nothing.

    29. TF

      Yeah, yeah. [laughs]

    30. DS

      Nothing. Literally nothing. First time we talked was, like, an hour and a half, and we get to the end and he goes, "I thought I was into podcasts." [laughs]

  20. 49:34 – 51:23

    Edwin Land

    1. TF

      very good guy. So I'm gonna zoom into your sort of expertise subject matter for a second, and then I wanna talk more about podcasting. But just so it doesn't become too much inside baseball, I do wanna come back and talk about podcasting. But you had mentioned, you have mentioned a number of different names kind of at the top of your list, people to learn from. Where does Edwin Land fit into that?

    2. DS

      Oh.

    3. TF

      And who is Edwin Land?

    4. DS

      So Edwin Land is the patron saint of founders. [laughs] So I want a picture of him in my house, like, you know, the Last Supper just be, like, Edwin Land in the middle like Jesus. So again, I'm very interested in who influences the influencers.

    5. TF

      Mm-hmm.

    6. DS

      And, like, where do these ideas actually come from? And, you know, Steve Jobs, if you have a Mount Rushmore of greatest entrepreneurs, his face has gotta be on it undoubtedly.

    7. TF

      Mm-hmm.

    8. DS

      He created the most successful product in history. I think he did it for the right reasons. I think he's a very fascinating person, obviously incredibly flawed as, like, a human, which he even said, you know? But what's fascinating is if you go back and, and which I do, is like, when I read a biography of somebody, I will make a list going back to, you know, your outline of what I'll do in the front of the books, which you called, what was-

    9. TF

      Front matter

    10. DS

      ... front matter.

    11. TF

      Mm-hmm.

    12. DS

      I didn't even know that term till now. Thank you.

    13. TF

      Yeah.

    14. DS

      I will write down all the other founders or all the other people they'll talk about.

    15. TF

      Mm-hmm.

    16. DS

      And so, like, I just did it with James Dyson. He's, like, obsessed with Buckminster Fuller, and Isambard Kingdom Brunel, and Jeremy Fry, and Alex Tsakiris, and all these people. He just repeats them over and over again, and you just realize, oh, he studied these guys, and then took their ideas and said, "Those ideas are good. I'll use them," and then makes $60 billion or whatever his company's worth. So Steve Jobs-

    17. TF

      Everyone should read about Buckminster Fuller

    18. DS

      ... I haven't read the book yet. I've read his ideas, but not the book that James read when he was in college.

    19. TF

      Mm-hmm.

    20. DS

      It's fascinating to me how it's almost all, like, and you usually find it early.

  21. 51:23 – 57:29

    Lessons from Sam Zell, Jay Pritzker, and William Zeckendorf.

    1. DS

      I had lunch with Sam Zell. I'm talking to him. I was like, "Yeah, man-

    2. TF

      How did he make his money, for people who don't know?

    3. DS

      People consider him an investor. He calls himself an entrepreneur. He called himself an entrepreneur. So what he's most well known for is in 2007, he sold the, I think the biggest real estate company in history for, like, 38 billion to Blackstone, and it kinda, like, tipped at the very top of the market, but he, he just likes to essentially buy businesses, try to make them grow. He would sell some. So, like, that's why people consider him an investor, but he considered himself a-

    4. TF

      Entrepreneur

    5. DS

      ... an entrepreneur. By the time I met him, he had 61 years of experience as, as an entrepreneur, and I like... My favorite entrepreneurs are I love talking to these people that have 40, 50. I'm not interested in the startup founder at all, like this 25-year-old kid that thinks he's smart. He doesn't have enough experience yet. Life is going to [chuckles] teach you what you n- you know.

    6. TF

      People who've ridden, like, uh, multiple, many multiple macroeconomic cycles, who have had to contend with different challenges at different points in their lives, not just when they have no responsibilities and no dependents-

    7. DS

      Yeah

    8. TF

      ... et cetera, et cetera, et cetera.

    9. DS

      Well, he says something in his autobiography that you were speaking to earlier. He's like, "Yeah, in, in earlier in my life, my career fought my marriages, and my career won, and that's why I've been married three times." The reoccurring theme is that you look at life as, uh, everything that's not work as kind of an unpleasant distraction, and you wonder why your relationship's broken-

    10. TF

      [laughs]

    11. DS

      ... 'cause you're not spending any time there. Like, of course, it's the outcome, and they all make this mistake over and over again. So what's fascinating about this is, we'll go back to Edwin Land in a minute, Sam Zell, in his biography, he's like, "Dude, I'm in college." This guy was making millions of dollars a year when he was in law school. That's how good of an entrepreneur he was from day one.

    12. TF

      Was that real estate?

    13. DS

      Yeah.

    14. TF

      Mm-hmm.

    15. DS

      He was developing, I think, student housing at the time. I think the student housing, but he was also, like, doing deals. Like, he's just a very gifted deal maker, and you see this with Rick.

    16. TF

      Yeah.

    17. DS

      Understanding, like, you'll bring something to Rick, and you'll be like, "Oh, here's, like, 10 things that are important."

    18. TF

      Do you wanna explain who Rick is briefly?

    19. DS

      So Rick is, his name's Rick Gerson. He's one, one of my closest friends. You've known him for what?

    20. TF

      Yeah, I don't know, 15, 20 years, a long time.

    21. DS

      15, 20 years. He's one of the most generous, thoughtful, and also simultaneously super intense people I know.

    22. TF

      He's a master of finance, came out of this just sort of amazing training environment, we can just call that for what it is for now in, in simplicity, and is one also of the best connected humans I've ever met.

    23. DS

      He identifies, oh, there's, there's like one thing. He learned that from Sam, and then Sam learned that from this guy named Jay Pritzker.

    24. TF

      Mm-hmm.

    25. DS

      It's, it's very fascinating.

    26. TF

      Chicago royalty.

    27. DS

      Yes, 100%.

    28. TF

      [laughs]

    29. DS

      So I actually just backed, there's like a, it's not a Kickstarter, but it's almost like there's no biographies of Jay Pritzker. And so this guy named Rockwood Notes that essentially put his hat out, and he's like, "Hey, I wanna do this, but I need to make at least, I think, 40,000 a year to write this book," and he's selling, like, $800 or $1,000 a year subscriptions. I was like, "Yeah, I'll obviously sign up for this." Like, I want a Jay Pritzker biography. So Sam Zell in his autobiography, he's like, "Yeah, I read this book by William Zeckendorf, and it changed my life because there's one idea in this book." It's what Charlie Munger said. There's ideas worth billions in a $30 history book, and there was this thing called Hawaiian technique. William Zeckendorf was, like, this real estate developer in New York, and he came from nothing, and then made a lot of money, then lost it all, and then made a lot of money, then lost it all again, and dies with no money.

    30. TF

      Mm-hmm.

  22. 57:29 – 58:52

    Edwin Land’s philosophies: Differentiation and doing to excess.

    1. TF

      So if somebody wants to study Edwin Land, where do they start?

    2. DS

      So I read this biography of Edwin Land I thought was incredible. It's called Insisting on the Impossible. It's the most comprehensive biography of him. People read it, they're like, "This book sucks."

    3. TF

      [laughs]

    4. DS

      I think it's riveting. There is a book, I think it's called Land's Polaroid. That's the one I'd read because it's only 250 pages and it's written by a guy that worked for and with Edwin Land for like 20 years.

    5. TF

      Mm-hmm.

    6. DS

      And I love those kind of things because you see him over a decade. But my point being is like, Jobs is talking about this guy when he was 25. Jobs knows he's dying when he's working with Isaacson on the biography. He knows he's dying, and he's still talking about... Edwin Land appears in Isaacson's biography of Jobs like six times.

    7. TF

      Hmm.

    8. DS

      Why is he still talking about this guy? How could you not be interested in understanding why? What is it about this guy that, that he admired and liked? He has a personal motto that I love and that I try to do. There's two of them. Edwin Land says, "My personal motto is very personal. It may not apply to anybody else or any other company, but is don't do anything that someone else can do."

    9. TF

      Mm-hmm.

    10. DS

      The importance of differentiation, I'm shocked at how few people understand how important it is. Dyson.

    11. TF

      Mm-hmm.

    12. DS

      Dyson's whole thing is like it has to be different even if it's worse.

    13. TF

      Mm-hmm.

    14. DS

      It should be different.

    15. TF

      That's interesting.

    16. DS

      He demands difference. He's got a very fascinating business philosophy. The, Dyson's mind's incredible. And then the other thing is he knows because he dropped out of Harvard twice. He goes, "There's something they don't teach you at Harvard Business School, that anything worth doing is worth doing to excess." [laughs]

  23. 58:52 – 1:00:25

    Entrepreneurial archetypes and conflicting advice.

    1. TF

      [laughs] So how do you think about different archetypes, perhaps that's the best word to use, within the, the pantheon of successful entrepreneurs? The reason I ask that is that I imagine you get questions along the lines of, and I get questions like this also, when you look across all of the biographies, what are some of the common patterns? Give me the top five-

    2. DS

      Yeah

    3. TF

      ... top six, and then people wanna grab that recipe. But it could be like, just to use a sports analogy, it's like, all right, you're taking the stretching routine from LeBron James, the weight training routine from Arnold Schwarzenegger, and this, this, and this. You're grabbing habits from mutants that are in entirely different spheres [laughs] or have different bodies entirely, and then trying to cobble it together. It may not work, right? That's point number one. Probably won't work. Number two is that within the world of business advice, whether it's autobiographies, biographies, interviews, there's a lot that conflicts, right?

    4. DS

      Yeah.

    5. TF

      So you have one person who says, you know, anything that's worth doing is worth overdoing, and then there's like, you can tell who the novice is because they do too much.

    6. DS

      Yes.

    7. TF

      Right? And I'm wondering how you think of entrepreneurship for yourself in terms of modeling different people or taking advice because you have, you could have two people just to use a metric that's easy for everybody to wrap their head around, like two billionaires, and they give you diametrically opposed advice. How do you personally pick?

  24. 1:00:25 – 1:05:21

    Daniel Ek

    1. DS

      There's no formula. So this is actually something, one of the things I'm like so thrilled with is the fact that like I've become friends with Daniel Ek, the founder of Spotify, and this is something we're actually trying to work on together because he brings this up. He's like, "We need alternative founder archetypes." And I, back up. First of all, like Daniel is an alien. There is a specific reason- That I wanted him to be the very first guest on the new show.

    2. TF

      Mm-hmm.

    3. DS

      I'm able to, like, build relationships with other people. Daniel's very special in the sense that, like, he's only a few years older than me, but he's so much more wiser than I am. I don't know how I, I can put this in words and make sense, but, like, 'cause he's, he founded and is still running a $120 billion company. [laughs]

    4. TF

      Right.

    5. DS

      That he's been running for 19 years. But he's, to me, he's still so underrated. And the thing about Daniel is not only is he wicked smart, right? But he's given me some of the best advice, and he does it in a very, like, reserved and very precise way. He's got very clear thinking. And I just cannot get over, like, how generous he is with his time and his advice to me. And, you know, he, he told me one of the things that was really important, and he said it like an offhand comment, but he's like, "You're really easy to understand, so therefore you're easy to help."

    6. TF

      Hmm.

    7. DS

      And he's just like, "I know what is important to you, and so therefore you're easy to help. You're easy to interface with." And so his point is like, every young founder thinks they have to be an Elon or a Steve Jobs. But I'm not, like, an Elon or a Steve Jobs. And the massive success, not only what he's done for Spotify, one of the best apps ever created, I think they have the most... I think there's only one other company in the world that has more paid subscribers than they do, and that's Netflix. But think about the way you feel when you get done using Spotify, and this is why I like all of the top people there too, and they've also been working together for excessively long time, Gustav, Alex, Daniel, all of them, is they want you, when you're done using Spotify, to feel good. If me and you spend an hour listening to our favorite music on Spotify, you feel great.

    8. TF

      Hmm.

    9. DS

      You spend an hour listening to Tim Ferriss' podcast, you're inspired, you feel great. On audiobook now, you feel great. I spend an hour on TikTok or Reels, I feel like shit.

    10. TF

      [laughs] Yeah.

    11. DS

      Like, Twitter, ugh, I g- I can't. Like, it just, I feel like-

    12. TF

      It's like the anti-therapy if you want to send yourself backwards. [laughs]

    13. DS

      So I like what they're doing.

    14. TF

      Is there any other advice that has, uh, stuck from Daniel to you?

    15. DS

      So yeah, don't let me forget the archetype.

    16. TF

      Yeah, I won't lose track of that.

    17. DS

      So the archetype is, I think, is really important. I think you'll really vibe with what his perspective on this is. Daniel will tell you advice in, like, a very... He's like a wise old man. I don't know how to describe it. One thing is implied and never explicitly stated, he just doesn't feel he has any... There's no ceiling on what he can achieve-

    18. TF

      Mm-hmm

    19. DS

      ... or what he can learn or what the effect he can have in the world. And when you spend time with him, that is transferred to you. And it's, like, one of the most important things, and I don't even know if I told him this. I had, like, tears in my eyes thinking about it. I remember, like, hanging out with him in Stockholm and, you know, he's done phenomenal stuff with Spotify, one of the best apps ever created, uh, best businesses. He's, like, wildly successful as an investor too.

    20. TF

      Hmm.

    21. DS

      And so I remember asking him, this is the funniest thing you'll ever hear. I go, "Were you always interested in investing?" 'Cause I knew his story. Like, we've, we've talked a lot about this. And he goes, "No. I didn't even know anything about it. I started learning." I go, "When did you start learning?" He's like, "2018."

    22. TF

      Hmm.

    23. DS

      I go, "How'd you start learning?" He goes, "Patrick's podcast." [laughs] And so he would just listen to people. He's like, "I like that idea. I'll take that idea. Oh, I don't like that idea. I don't like that at all. I'll avoid that." And the way Patrick describes it is, like, out of anybody you know, Daniel has the ability to apply what he's learning faster than anybody else and at a grander scale.

    24. TF

      I think he's also a very, very, very good systems thinker, so he's not at a risk of cobbling together this sort of camel that is a horse designed by committee-

    25. DS

      Yeah

    26. TF

      ... that has a bunch of inherent problems and conflicts within it, right? Like, he'll, he'll be able to figure out how to put pieces together from first principles that function well as a whole.

    27. DS

      Let me tell one other piece of advice-

    28. TF

      Yeah

    29. DS

      ... that he gave me, and he tells it in a story form. This is why he's like the wise old man. And essentially was, "Remember why people love you. Like, you sit in a room and you read all the time, and then you make this thing on the other side that educates and inspires us and gives us energy. And as soon as you stop doing that and you start saying yes to all these distractions," and I don't even know if... I think I'm, we might have talked about this in the episode we did that comes out in a few weeks. But he tells it in a story.

    30. TF

      Mm-hmm.

  25. 1:05:21 – 1:08:12

    Further founder archetypes

    1. TF

      I'm curious what you think are some of the different archetypes because I think of the hundred-plus startups that I've invested in since 2008, and there's a lot of variability.

    2. DS

      Yeah.

    3. TF

      Right? You've got the engineer, let's call it the engineer founder, right? Somebody like, uh, Tobi of Shopify.

    4. DS

      Mm-hmm.

    5. TF

      Right? Or, uh, Luis von Ahn of Duolingo. Then you've got the sort of like genius operator, negotiator, warrior, like a Travis Kalanick, right? Very different personalities, very different superpowers. And you just go down the list and you see some people come from like a finance numbers kind of like spreadsheet god perspective, and, like, they just have an analytical advantage, right? Like, it's, it's very comparable to investing in some ways.

    6. DS

      Mm-hmm.

    7. TF

      Looking at the investing world. They have this analytical advantage, let's just call it. And I was trying to pick out what, if anything, might be commonalities because you also have, like, the crazy artist who then figures out how to harness some of their [laughs] superpower. And it strikes me that there are at least two that immediately jump to mind. One is longer term time horizon.

    8. DS

      Mm-hmm.

    9. TF

      Right? Kind of the-

    10. DS

      Those are the people I'm obsessed with

    11. TF

      ... like the Jeff Bezos type of mindset where it's like if, if you have the exact same toolkit, the exact same competency, out of the box genetically you're built exactly the same as someone else, but you are able to think And plan longer term, it can be a huge advantage. Second is something that you mentioned where Daniel was saying to you, like, "This is the magic." So just remember this is the magic-

    12. DS

      Yeah

    13. TF

      ... when other opportunities, other shiny objects show up, because they will, even in very early stages, and if you deviate, it's incredibly easy to sort of self-immolate if you lose track of that, right? You, you see that a lot when CEOs get replaced sometimes, founder CEOs. Sometimes they need to be replaced, but what else would you add to that or how would you expand on any of it?

    14. DS

      Just look at the founders of some of, like, the biggest companies in the world now, right? Like, they would go to war against each other, so think about, like, Oracle and Microsoft.

    15. TF

      Mm-hmm.

    16. DS

      You can't think of two different founder archetypes than Bill Gates and Larry Ellison. Larry Ellison's like, "I'm a sprinter. I have intense, very intense periods of work, weeks at a time, months at a time, and then I need to go on my boat with a bunch of Italian models."

    17. TF

      Mm-hmm.

    18. DS

      "Right? This is what I- how I have to live my life." Bill Gates is, he'd be walking into this room right here, and his feet would be under the ground, underneath his desk. He's sleeping for three hours. He's getting back up, and he's going back on the... He's a grinder.

    19. TF

      Mm-hmm.

    20. DS

      I've been trying to name some of these, and I, I haven't done this yet, and, but

  26. 1:08:12 – 1:14:35

    Anti-business billionaire?

    1. DS

      I... And the problem is I never write anything.

    2. TF

      Mm-hmm.

    3. DS

      And this is all, like, improv, you know? One of them is, like, the anti-business billionaire, and so in that category, it's like these people are so obsessed about one thing, and that's the quality of the product that they're making.

    4. TF

      Mm-hmm.

    5. DS

      They make non-financial decisions, like Steve Jobs making sure that the inside of the Mac looks beautiful even though you can't open it up and it costs more money. He doesn't care.

    6. TF

      Yeah.

    7. DS

      He wants the best product. James Dyson's like this.

    8. TF

      Mm-hmm.

    9. DS

      He's an anti-business billionaire. Yvon Chouinard, founder of Patagonia, anti-business billionaire. These guys, they're obsessed with two things, quality of the product that they're making and retaining control of their company over long term.

    10. TF

      Mm-hmm.

    11. DS

      And the funny part about that, the reason I call them anti-business billionaires, because if you make the world's best product, right, and you retain control over your company, you wind up with the money anyways.

    12. TF

      Yeah. I can think of a, a few people, I mean, within my portfolio who retained a lot of their equity at least, and that's it, which is kind of preserving the magic, right, in terms of the best product.

    13. DS

      Everybody's like, "Look at what happened to Larry Ellison right now." It's like, yeah, the guy, I think they raised... I could be wrong, but I think Oracle raised thirty-two million of equity in our IPO and no more after that, and then the guy would refuse, even when they were almost going out of business in 1990, he still wouldn't sell. They're like, "Sell your equity." Like, "No." He's like, "It might be worth nothing." He just wouldn't sell it, and then he's buying back stock. So he owns, I think, forty... I think he went down to twenty-four percent. Now he's back to, like, forty-one percent of Oracle. The company's fifty years old.

    14. TF

      Yeah.

    15. DS

      Like, forty-five years old. I think he was, like, thirty-something when he founded the company. He's just a- an anomaly. And then you have people like Elon, where it's just like, "I'm gonna run..." I wouldn't even think that's possible. How the hell do you run seven companies at the same time?

    16. TF

      [laughs] I can barely manage three employees. I don't know.

    17. DS

      Yeah, exactly.

    18. TF

      Not a good answer. [laughs]

    19. DS

      So like that is the point. I do think Daniel hit on something that no one else has put in front of me. It's like, man, there's not... Like, the people are gonna dominate. Obviously, Elon's the, the most famous entrepreneur in the world.

    20. TF

      Mm-hmm.

    21. DS

      But even, like, Bezos is very different, and then you have these people that just like to make money, and that is their scoreboard. This is another thing I learned from Michael Dell. There's two things, one thing you just said, where like protecting the magic. The advice that Dell gave me when I had dinner with him is, and he does this in story form too, 'cause that guy's been running his business for forty-one years.

    22. TF

      Mm.

    23. DS

      Forty-one years. It's insane. And his whole thing is just like, "You're not gonna be taken out by competition. You're gonna sabotage yourself."

    24. TF

      Mm-hmm.

    25. DS

      "Entrepreneurs sabotage themselves."

    26. TF

      Yeah, I believe that.

    27. DS

      "And the amount of people that were doing the same thing I was doing, and they were ahead of me," this is Dell talking. "They were ahead of me, but then they got to five hundred million a year in revenue, and they're like, 'I have a house on Lake Austin now.' They're in the same city. They're doing the same thing as him in the same city, and they're smoking him. They're a- ahead of him by, like, a few hundred million, right? And they're like, 'Oh, I can chill now.' No, you can't, 'cause you got Michael Dell right across the, the river, and he's not gonna s- chill. That guy has no chill."

    28. TF

      [laughs]

    29. DS

      He just... When I went to him, I was like, "What the..." I heard he's got this wonderful house in Hawaii. His son was telling me about this, and I was like, "We're in Austin in July, you know."

    30. TF

      It's hot.

  27. 1:14:35 – 1:17:13

    Advice from “shark” Michael Ovitz

    1. TF

      So I have a couple of bullets. You should explain who Michael Ovitz is. Why don't you do that first, and then I'll, I'll just talk to two questions related to Michael Ovitz specifically.

    2. DS

      [laughs] Michael Ovitz is a, is a, is a shark. He's, uh, one of the most intense people. He-- I think he's 80 by now. Rick and I live very close to each other in Miami, okay? And we always have breakfast at the same spot that I'm not gonna say publicly.

    3. TF

      Yeah, good idea.

    4. DS

      [laughs] And so we're hanging out-

    5. TF

      You can do a disinformation campaign. Sure, yeah. The, it's always at Denny's.

    6. DS

      [laughs] Yeah.

    7. TF

      Moon's over Miami.

    8. DS

      [laughs]

    9. TF

      [laughs]

    10. DS

      And so his phone's on the table, and it rings, and it says Michael Ovitz. And I gasp. I'm like, "Oh," 'cause I read... Everybody knows who Mike... Like, I-- Michael Ovitz was the most powerful man in Hollywood at one time. He had, like, 75% market share, 90% market share. He was the most powerful agent. He's the founder of CAA, which still exists to this day. And I'm like, "Oh, God." Like, "I know who that is. I've done episodes on this guy." And so he picks up, and they've been friends for like 20 years, 25 years, something like that.

    11. TF

      Mm-hmm.

    12. DS

      And he goes, "Hey, I, I'm sitting here with somebody you might know. Have you ever heard of David Senra and the Founders podcast?" And Michael pauses. He goes, "I listened to four of them yesterday." [laughs] He was on his boat in St. Barts.

    13. TF

      That's incredible.

    14. DS

      No, but this is how, why he's a shark-

    15. TF

      Yeah

    16. DS

      ... and a killer. He's on his boat in St. Barts. He's, like, studying Rockefeller and Vanderbilt. He's, like, quoting stuff from the episode.

    17. TF

      Rockefeller, one of the biggest sharks to ever live.

    18. DS

      Oh, 100%. And so we wound up having dinner, and this is one of the things I asked him, you know, because his whole thing is like you're gonna run through, you know, you're gonna meet thousands of people in your life. He's gonna definitely meet way more people than I will 'cause I'm an introvert, and he, he used to, like, call 300 people a day 'cause he was, like, kind of running Hollywood.

    19. TF

      [laughs]

    20. DS

      But his, Ovitz's advice to me was just like, you know, you're gonna meet thousands of people in your life, and what I would recommend is just spend all the time with the handful that really matter. And he's like, "For me, Rick is one of those people." And I go, "Why?" And obviously, you know, he, he's like, "Oh, he's intelligent and basically..." But he's like, " 'Cause he tells me the truth."

    21. TF

      Mm-hmm. That's one thing you can rely on Rick for. I'm not sure he can help himself.

    22. DS

      But, but I-

    23. TF

      Not sure it's a conscious decision. [laughs]

    24. DS

      But no, but in general, his whole point is like when you get to be as famous and as well-known, as wealthy as Ovitz, everybody's gonna kiss your ass.

    25. TF

      Yeah.

    26. DS

      Everybody wants something from you. They want, either wanna tell you how great you are, or they want money from you, or they want you to sell, like buy something. And he's just like, "There's so few people that you know that, like, truly love you for you and don't want anything from you. They just wanna be friends, and they will tell you the truth." And this is the very dangerous thing that really successful people do. They have, they surround themselves with people that don't tell them the truth.

  28. 1:17:13 – 1:18:14

    The hands-on approach of practical founders

    1. TF

      Mm-hmm.

    2. DS

      And this is an idea I got from Jim Casey, the founder of UPS. He realized that there's this weird, like, capture if you only talk to your top executives. So let's say you have 10 top executives, and then they distribute everything else throughout the company. They work themselves in a position where they have the ear of the king, and you hear nothing good. So he's like, "I don't wanna talk to them at all." He would stop and talk to every single... He'd make his driver stop every time they see a brown truck, and he would talk to the people doing the actual service.

    3. TF

      Because he wouldn't get the bad news or he would-

    4. DS

      They would tell them what actually is going on.

    5. TF

      Yeah.

    6. DS

      What is actually happening. And the crazy impressive founders that I've been able to spend a lot of time with, most of them are 60, 70, 80 years old. Those are my favorite. I like hanging... I'm, like, I love them. They're not in their office.

    7. TF

      Mm-hmm.

    8. DS

      They're in their warehouses. They're on the factory line. They're in their stores. They're constant contact with the customer and the person delivering the, the service to the customer. They're not looking at a whiteboard with their executives. They're very practical, non-theoretical people. I think it's, like, really important.

  29. 1:18:14 – 1:18:36

    Doing one thing relentlessly.

    1. DS

      So in my own thing, it's just like I like to be obsessed and focused on one thing. I don't like to multitask. So therefore, everybody's like, you know, every single publisher is like, "Write a book."

    2. TF

      Mm-hmm.

    3. DS

      "You should do this." Everybody says, "Hey, I like X, so do Y."

    4. TF

      Yeah.

    5. DS

      And I'm like, "But then if I do Y, I don't do X." And so my whole thing is just, like, very simple. I just wanna, I wanna do one

  30. 1:18:36 – 1:21:40

    “This can’t be my life” as a powerful motivator.

    1. DS

      thing relentlessly.

    2. TF

      So related to Michael Ovitz, there are a few notes here that I think relate to the new show-

    3. DS

      Yeah

    4. TF

      ... and the interview you did with him, and I wanna ask about two of them. So the first is the benefits of low introspection.

    5. DS

      [laughs]

    6. TF

      And the second, so you can tackle these in either order, is, "This can't be my life," in quotation marks, is a powerful motivator. Can you expand-

    7. DS

      Yeah

    8. TF

      ... on those?

    9. DS

      So this can't be my life is a very powerful motivator. You see it over and over again. I think the sense of drive, like the way you grew up on Long Island, the way I grew up, I was like, "I'm not going out like this."

    10. TF

      Yeah.

    11. DS

      "I don't care what I have to do."

    12. TF

      I'm not gonna replay this movie.

    13. DS

      No way. I think in many cases- Seeing examples of what you don't want your life to be is more powerful than seeing what you want it to be. I think maybe that one comes first, and then you start to see, "Oh, I actually... This is the, the path I wanna go down."

    14. TF

      There's an expression in Japanese which is hanmen kyoshi. Hanmen is, like, opposite side. Kyoshi is teacher.

    15. DS

      Mm-hmm.

    16. TF

      And it's someone who teaches you by showing you what not to do.

    17. DS

      Yeah.

    18. TF

      Right?

    19. DS

      Yeah. I would say my family definitely-

    20. TF

      I've got a lot of those

    21. DS

      ... a case. Yeah. Th- like, you just see this over and over again. And so with him, like, he could lit- he grew up in the Valley. He could see where he wanted to be. He could see the mansions of Beverly Hills. He saw the contrast between... This is what I'm worried about with social media. Before we grew up, what do you see? You basically see, like, oh, like, that's the nice neighborhood over there. That's kind of a bad neighborhood. Now you see, like, the richest people in the world every day and the poorest people in the world. Like, you're exposed to nothing but extremes, which is like we've never-

    22. TF

      Mm-hmm

    23. DS

      ... in human history, we've never been exposed to that. And, like, what is the long-term effects of that? I have a teenage daughter now, and I think there's a lot of negativity of this, like, you only see the most beautiful people. If you were just in a town like where we grew up, you might see a really beautiful woman. You're not seeing them all day long, like these, th- th- just, like, these unfair-

    24. TF

      Getting barraged with it

    25. DS

      ... yeah, barrage of unattainable, you know, standards. So with him, he was, like, fiercely driven to succeed. And one of my favorite parts of his book, the guy now, wildly successful. But even before that, when he s- he left, I think it was William Morris Agency, he starts CAA, they start to have a little success. He winds up buying a house in Brentwood, and it was like $650,000, right? Which is fantastic, but nothing compared to what's gonna happen over the next decades in his life. But he just woke up every morning, he's like, "I can't believe I live in Brentwood."

    26. TF

      [chuckles]

    27. DS

      "I can't believe this. I did this." And then once you start seeing results, the grind becomes very addictive. And he, if you had what's the archetype? Grinder.

    28. TF

      Grinder.

    29. DS

      Like, [chuckles] I'm going to throw sheer hours and energy. He's also an amazing, one of the best salespeople alive, very charismatic. He's got a lot of superpowers. I, I actually met Marc Andreessen, and I asked him this because Marc Andreessen's on record saying that when he started a16z, they essentially copied CAA.

    30. TF

      I think they brought Michael Ovitz in.

  31. 1:21:40 – 1:24:33

    Low introspection as a common trait among founders

    1. DS

      different." Now, the low introspection thing is I'm not a controversial person. I'm just sharing lessons from history that I read in a book. You don't have to listen. You don't have to pay attention. It doesn't matter. But when I bring up the fact that a lot of these people have z- low or zero introspection-

    2. TF

      Mm-hmm

    3. DS

      ... meaning that when they find what they wanna do in life, they wake up, and they know exactly what they're doing that day. Sam Walton was not waking up saying, "What are my feelings like today? What should I do? Should I think about the meaning of life?" He's like, "No, I found Walmart. I'm just gonna... I made one Walmart. I'm gonna make another one and another one [chuckles] and another one. I'm gonna make every Walmart better and better and better." And I think having low introspection after you, you've found your mission in life, and this is the sad thing, I think most people never find their mission. I know I found my mission. There's n- I don't think about, "What should I do today?"

    4. TF

      And we're gonna talk obviously about the new show, and we've been alluding to it and mentioning some of the guests. But before we get there, so you're about to meet Michael, and he had been ostensibly on vacation, but he's listening to-

    5. DS

      Yeah

    6. TF

      ... your episodes on Rockefeller and others. Do you recall any of the other episodes?

    7. DS

      The Vanderbilt one stuck up in my mind. I mean, we text about them. I don't remember the Rockefeller and the Vanderbilt, but the Vanderbilt especially 'cause Vanderbilt's like, uh... You know, what I say is, like, I'm kinda telling the same story over and over again. I think it's more like church, just like I went to church. I grew up as a fundamentalist Christian. We met together with like believers on regular intervals on Wednesday and Sunday, and it's not like the preacher got up there and was like, "Hey, we talked about that Jesus guy enough. [chuckles] We're gonna move on to somebody else." It's like we literally just go to the same book over and over again. And so I always say there's, like, always a historical equivalent to anybody we're dealing with today or in the past. But Vanderbilt, to me, there's not, like, an entrepreneurial historical equivalent.

    8. TF

      Mm-hmm.

    9. DS

      He's like Putin or something. When he died, he controlled 5% of the money supply, [chuckles] one out of 20 b- dollars.

    10. TF

      So I guess the reason I was asking about the episodes-

    11. DS

      Yeah

    12. TF

      ... and I don't know Michael, so-

    13. DS

      Yeah

    14. TF

      ... uh, this is not a judgment or, or criticism of Michael at all. But I suppose if you believe that there is a value to low introspection for the purposes of building a business, which I would agree-

    15. DS

      Yeah

    16. TF

      ... right, is there not a risk? And I have, I have not listened to those particular episodes on Rockefeller and Vanderbilt, but I've read a bit of the history. [chuckles] Like, these are not necessarily people you automatically want to model everything on all of-

    17. DS

      I think, no, I think Ovitz would. [chuckles]

    18. TF

      Well, okay. So this is, I suppose, my question is, like, is there a risk of ending up sort of amoral, immoral, or, like, sociopathic if one of the things you optimize for is low introspection because... Or maybe that's just hardwiring, frankly, and you're just not inclined to do it because there-

    19. DS

      That's a great question

    20. TF

      ... be- because this archetype does exist, right? Just like the rape, pillage, destroy archetype is an archetype.

    21. DS

      They're overrepresented in entrepreneurship be- why? Because if entrepreneurship done correctly yield the greatest material rewards in human history.

  32. 1:24:33 – 1:27:15

    Robert Caro.

    1. TF

      Yeah.

    2. DS

      So of course, it's gonna be full of psychopaths and sociopaths. Like, whatever... I don't know if you know the numbers on this. What, they, they assume 5% of the population's sociopathic or something like that? Do you know something like that?

    3. TF

      I don't know the number.

    4. DS

      Let's just make it up. It's 5% of the general population. It's probably, you know, five times that of entrepreneurs and investors and people like this or anybody, political power, power in general. This is why I think the work of Robert Caro is so interesting.

    5. TF

      Mm-hmm.

    6. DS

      And I always make the argument that, like, there should be a law. The only one law that I would foist upon society is that there's only one person allowed to write a thousand-page biography. I l- I have no problem reading. Almost none of the books that I've read that are a thousand pages needed to be a thousand pages. You just, they just didn't know what to put in there.

    7. TF

      Mm-hmm.

    8. DS

      Robert Caro is the only one that should be able to write long biographies because everything that he has in there should be in there. I think he's a master of his craft. He's the best to ever do it. But he's saying, "I'm not writing biographies. I'm writing about how Humans accumulate and then wield power

    9. TF

      Mm-hmm

    10. DS

      And I did it first on a local level in New York with Robert Moses, and now I'm showing what happens on a national level. And guess what? LBJ would sacrifice everything-

    11. TF

      Mm-hmm

    12. DS

      ... to get what he wanted. Personal ethics, his relationships, everything.

    13. TF

      Stealing elections?

    14. DS

      Yeah. This is the wonderful thing about studying history. History does repeat, human nature does. Me and you both love Will and Ariel Durant.

    15. TF

      Mm-hmm.

    16. DS

      Right? Read The History of Human Civilization. Read their 100-page book, Lessons of History. The same stuff repeats over and over again, so when it comes out and you see it's on the news, like, "Oh, of course no one stole the election." It's like stealing every election, like, in all different countries. Stealing elections i- is an American pastime.

    17. TF

      Yeah.

    18. DS

      Just read Robert Caro's... And it could be like a little, you know, Senate election in Texas.

    19. TF

      Exactly.

    20. DS

      If you don't think that-

    21. TF

      The missing ballot box.

    22. DS

      Yeah. The line I have about this is from Will Durant, where he's just like, "In every age, humans are dishonest and governments are corrupt." It's one of my favorite quotes from Lessons of History. In every age, nothing that we're doing is new. We're just, we're telling the same stories over and over and over again. You see the same people over and over again.

    23. TF

      Mm-hmm.

    24. DS

      So yeah, I'm sure there's a ton of people that read these biographies and that listen to my podcast that are absolute psychopaths.

    25. TF

      [laughs]

    26. DS

      I don't think Ovitz is a psychopath. He's an extreme winner. He wants to win.

    27. TF

      The line may be pretty thin.

    28. DS

      Yeah, of course.

    29. TF

      [laughs]

    30. DS

      Of course.

  33. 1:27:15 – 1:28:56

    James Dyson’s persistence vs. the risk of blind stubbornness.

    1. DS

      nature.

    2. TF

      I wanna ask you, and we, and, and then I'm gonna hop to questions about podcasting and the new show, about how you think about assessing leaders, entrepreneurs, reading biographies or autobiographies, and figuring out what people claim as things that help them to succeed actually help them versus hindering them. In other words, like, what are the because of versus the in spite of? So for instance, if high disagreeability or low agreeability is common across a lot of founders-

    3. DS

      Mm-hmm

    4. TF

      ... to what extent can you point to that as one of the causal factors for their success, as opposed to just an emergency brake they had on causing all sorts of problems that they managed to overcome, so they succeeded despite? How do you think about separating those two things?

    5. DS

      One of the things I love about James Dyson, who I, you know, is a hero of mine, it's the person that on the planet that I wanna meet that I haven't met, number one is him, and what I love about him is, like, how stubborn he is-

    6. TF

      Mm-hmm

    7. DS

      ... 'cause I see myself in that, right? And it turns out his stubbornness worked out for him because he had the right idea. But this is where it goes back to, like, you can't blindly copy. There's no formula. There's no formula, there's no track. So it's like he's stubborn on an idea that was a great idea, it just needed more time.

    8. TF

      Mm-hmm.

    9. DS

      You could be stubborn on an idea that's terrible and going nowhere, and then you did the exact same thing for the exact same amount of time, and on the other side of that, he has one of the most valuable privately held companies in the world, and you have a miserable life. There's no answer to that.

    10. TF

      Mm-hmm.

    11. DS

      There's nobody coming to save you. None of this shit works if you can't trust your own judgment and figure things out. That's why when people are just like, "Oh, more people should be entrepreneurs," I don't know about that. I wanna, like, encourage the people that think they can do it

  34. 1:28:56 – 1:36:10

    Todd Graves (Raising Cane’s) as an example of relentless focus on one idea.

    1. DS

      to do it, but I think in many cases, most people should work, like, they should choose a different path-

    2. TF

      Mm-hmm

    3. DS

      ... because it's very, very risky. You know, like, uh, Todd Graves, the Raising Cane's guy I told you about, right? His whole thing is entrepreneurs should have higher risk tolerance. James Dyson multiple times risked every single possession he had to chase his dream. He signed over his house multiple times. If he failed, they could have been homeless. It worked out for him. Todd Graves had this crazy way to finance the first 28 Raising Cane's, where essentially he goes to an angel investor, he goes to Tim Ferriss and says, "Hey, you gonna give me $200,000 loan, okay? It's gonna be subjugated loan to the bank. I'm going to guarantee you a 15% return on the $200,000 for X amount of time." You say, "Oh, that sounds great. You, you're paying me 15% on my 200 grand." But you don't get any equity. I take that 200,000 equity that I have from this document from Tim, I go to a bank and say, "This is ex- as collateral. Loan me the other 600 grand or whatever the number is to, to get this up and running." And he did that for 28 times and he's like, "Oh, I'm rolling, rolling, rolling." Leverage up to his eyeballs. What's the problem? I open up, every time I open a new Raising Cane's, there's a line out the door from day one. Well, then a little thing called Hurricane Katrina comes, and guess where? 28 of his restaurants are all in Louisiana [laughs] .

    4. TF

      Yeah.

    5. DS

      And he almost died. And he says, "If I didn't come out of that, there would be no story. It'd be gone." And then I guess the second part, I don't know why this popped in my mind, but you know, when you're reading history, right, we're reading about stories that happened 100 years ago, 200 years ago, 50 years ago. Some of them are from that person's own mouth. Like, imagine if you tell your own life story. Here's the good part. You're gonna, like, you, you're gonna hide the bad. You're human.

    6. TF

      Yeah.

    7. DS

      Right? And so people are like, "Well, how do you know if what you're reading is true?" The line is just like, if you think the news is fake, wait till you read history.

    8. TF

      [laughs]

    9. DS

      It's like-

    10. TF

      It's just old news. [laughs]

    11. DS

      [laughs] My idea is like, we're not taking a test at the end of this. I'm not saying like, "Did this actually happen in 1912?" It's like, is the idea behind what he's doing a good idea for me?

    12. TF

      Yeah.

    13. DS

      And so, like, the example of, like, Rockefeller, right? That you see that Elon used, where, like, Rockefeller tells this story. I don't know if it actually happened, but he tells this story where they would have to solder closed the, the barrels that they transport oil in, and he goes up one day and he says, "How many do you, drops of solder do you use?" He's like, "I use 40." He's like, "Have you ever tried 38?" And he's like, "No, we've never tried 38." "Can you try 38?" They try 38, it leaks. "Okay, try 39." They try 39, doesn't leak. That one drop of solder at the time of the business saved him, you know, $2,500 a year. The business grows and compounds for the next three decades, and now he's saving like, you know, hundreds of thousands from that then. Did that actually happen? I don't know, but that's a good idea to, to find the limit. To actually, hey, maybe I should control my costs a little bit more. Maybe I should, I need to actually see if I can do this in a more efficient way. I don't know if it happened. I just want the idea behind it.

    14. TF

      Just to reiterate what you're saying, it's, it's tough to separate the fact from fiction, right? And then sometimes this is actually why I just read fiction [laughs] 'cause I'm like, there still are truths to extract, right? There are principles that you can extract from, this is now cliched 'cause it's been made into a popular movie, but Dune or Stranger in a Strange Land. Like, you can actually pull a lot from just straight-up fiction. And then when it comes to the business side, you know, 'cause I've read so many, not as many as you, but tons of business books. Still have my early copies and my notes from those books with Losing My Virginity, Richard Branson, early Yvon Chouinard-

    15. DS

      Yeah

    16. TF

      ... you know, I think it's Let My People Go Surfing-

    17. DS

      Yes

    18. TF

      ... et cetera. Still have all those books. And part of the reason also that I like early biographies, so let's just say like Hard Drive on Bill Gates versus a later, I don't wanna say sanitized, but let's say sanitized version where-

    19. DS

      I'm going through this right now

    20. TF

      ... right, where it's like, look, Warren Buffett, love the guy. He's turned himself into like the aw shucks grandpa neighbor who takes-

    21. DS

      Killer

    22. TF

      ... his garbage out in-

    23. DS

      Killer

    24. TF

      ... a robe. But he's a killer.

    25. DS

      Yes.

    26. TF

      And I remember reading, I think it was The Making of an American Capitalist way back in the day, and the story that stuck out, and I hope I'm not inventing this, I don't see why I would, but his routine was to go home, walk upstairs, and read, uh-

    27. DS

      Step over his children.

    28. TF

      Exactly. So his, I believe his son who's like-

    29. DS

      Yes, step over

    30. TF

      ... fallen down the stairs, is like sprawled out like a chalk outline on a crime scene. Steps over his injured son to go upstairs to do more reading of S1 filings or whatever he was doing.

  35. 1:36:10 – 1:40:19

    Considering trainable vs. non-trainable attributes

    1. TF

      know?

    2. DS

      Timing. I think timing-

    3. TF

      Timing is a huge piece. By the way, these are not all reasons to discount anything, but I just wanna mention a couple that I try to think of. The other I try to think of, because I might try to mimic someone in sports, right, if I'm trying to learn something new-

    4. DS

      Yeah

    5. TF

      ... or language learning or whatever it might be, is what are attributes, what is trainable and what is not trainable, right? Because I've heard these stories from people who know Bill Gates and they're like, "Well, we were gonna go on this short vacation in fill in the blank." I can't remember. Costa Rica, right? And they're gonna go on a birding trip in the morning. It's just like a two, three-hour thing with a world-class birding guide. And they do the trip, and the night before, Bill has stayed up and read five books on birding, memorized them-

    6. DS

      Yeah

    7. TF

      ... seemingly without trying, and is basically having like a peer-to-peer discussion with the birding expert as they're going through the rainforest. That's not normal.

    8. DS

      No.

    9. TF

      That's like I'm gonna, I'm gonna do calf raises to make my body look like Michael Phelps. Like, no, you're not. That's not gonna work. So it's like when I'm looking for people to model, I'm trying to find people who have hopefully a comparable composition of strengths that I can amplify in myself or that are coachable, right? And so the, the question after all that is does anyone stand out to you of the biographies or people you've met where you're like, in terms of someone doing the most with the hand they have been dealt-

    10. DS

      So not aliens. Okay

    11. TF

      ... like they're not a freak of nature necessarily. 'Cause there are freaks of nature, right, among the people that You study, the people I study, but it's like, all right, these people might have a few strengths, but they're not complete freaks. They're not the Usain Bolts-

    12. DS

      Yeah

    13. TF

      ... of fill in the blank. And man, oh, man, did they play their hand well. They're just so good at playing the hands that they are dealt. That person. Does anybody stick out?

    14. DS

      Sam Walton.

    15. TF

      All right.

    16. DS

      Sam Walton's one of my favorite entrepreneurs. He had this crazy idea. He obviously didn't know what Walmart was gonna turn into, but one of the ways they avoided all the inheritance tax is if you give away the equity before it's valuable. So if you look at, the last time I checked, if you look at all of the Walmart equity owned by the family, that means the wealth that came from his idea would be like $432 billion today-

    17. TF

      Hmm

    18. DS

      ... if it was consolidated in one person, right? And when you study Sam, he's like obviously smart, but he would just like, he didn't really know what he was gonna do. Then he had this idea, he's like, "Well, maybe I can be good at retailing." And then he starts out in Newport, Arkansas, with one store. And this is what drives me insane about the modern-day entrepreneurship industry, is like how everybody's, they start out with weird goals. Like, "I'm gonna build a trillion-dollar company," or, "I'm gonna be the fastest person to 100 million ARR." And it's just like, okay, but none of these people talk like that. Like you-

    19. TF

      Mm-hmm

    20. DS

      ... you're doing it for the wrong reason, so you probably won't get there if that's just the case. Like what Jerry Seinfeld says, like if you're just doing it for the money, you'll only get so far. And with him, he was just fascinated by stores and trying to make it a little bit better every day.

    21. TF

      When he's on vacation, right, he would, didn't matter where he was, he would go into a retail store.

    22. DS

      His kids told a story, it was just like vacation was essentially driving to different towns and [laughs] checking out different retailers. The most important thing about his story, one of the most important things, is this idea to go slow now so you can go faster later.

    23. TF

      Mm-hmm.

    24. DS

      And so you're like, okay, the beginning of his career, he's like in one tiny store. I think they started doing like 25,000 a year, 25,000 a year in revenue. I think he gets up to like 250 grand. Took him five years. But for five years, he just had one store. He was like experimenting, understanding, trying to figure out what the different, you know, different parts of retail are, 'cause there's no such thing as discounting and wholesale and all the other stuff that he was doing that he's gonna do later on. And then what's fascinating is later in his career, after Walmart, he then takes that idea, he goes and visits Sol Price, who we mentioned earlier, and he takes that idea. He's like, "Oh, this is a great idea. I'm gonna do this." He does Sam's Club. And in that same five-year period, so you have the first five years, one store, separated by maybe 40 years in the career, that second five years when he's starting something else, in that five-year period, he doesn't have one store. He winds up doing, I think, 100 stores and like 7 billion in revenue-

    25. TF

      Hmm

    26. DS

      ... from this new category. Because you see him learning, and so like, yes, I think he was brilliant, but he's not memorizing five books overnight and doing that. This

  36. 1:40:19 – 1:43:32

    Charlie Munger’s library.

    1. DS

      is like mine. One of the reasons that I do what I do is because Munger became a hero, and he talks over and over again about being a biography nut, that he read more biographies than anybody else. I got to spend three hours inside of his house, right, talking to him right before he died. I don't care how many biographies I read, how many books I read for the rest of my life, I don't, I cannot have a brain like him. I will never have a brain like him. Anybody at 99 is gonna have some level of cognitive decline. You know what one of my first thoughts was about an hour and a half into the conversation with him? Was this guy had to be terrifying when he was 60.

    2. TF

      Yeah.

    3. DS

      Terrifying.

    4. TF

      Mm-hmm.

    5. DS

      Terrifying. Think about this. Everybody that I know, I always, when I get to meet fancy people, I always ask them like, "Who's the smartest person you know? What's the best business you know?" And it can't be like Apple. It's like these interesting, weird things. And every single person that says if they have no Buffett and they don't tell you it's Buffett, they're wrong.

    6. TF

      Mm-hmm.

    7. DS

      And Buffett chose this guy to let him mold hi- and shape his thinking. What does that tell you about his intelligence? And I remember, because this is what I do, again, I'm like laying bricks every day. I don't think I'm a brilliant person. I just like show up every day and don't quit. And so once I find Munger, I read e- literally, not, oh, I read some of the books. I read every single book on Munger. Then I reread my highlights over and over again. So my days, I wake up, work out, read for a few hours, have lunch, then reread past highlights in the afternoon. All my social media posts are just me rereading highlights. I read every single book on Munger, then I reread all the highlights. But then I read all the books he tells me to read.

    8. TF

      Mm-hmm.

    9. DS

      'Cause he'll tell you, "Read Les Schwab." He'll tell you all these things. He'll tell you Henry Kaiser. I was like, "Who the hell is Henry Kaiser?" Henry Kaiser started 100 companies. He built the Hoover Dam. He built Liberty Ships. I go, "What?"

    10. TF

      By the way, just the fact that pretty much everyone listening to this podcast will have no idea who that person is-

    11. DS

      Yeah

    12. TF

      ... just underscores, I think, how ridiculous it is to get overly fixated on legacy as an excuse for all sorts of behaviors.

    13. DS

      Yes.

    14. TF

      Nobody's gonna remember you.

    15. DS

      No, I'm anti-legacy and I'm anti-family dynasty. I think bequeathing your kids a bunch of wealth is, well, that's another story-

    16. TF

      Yeah

    17. DS

      ... for another day.

    18. TF

      But okay, 100 companies.

    19. DS

      So-

    20. TF

      Right.

    21. DS

      So-

    22. TF

      Hoover Dam, which by the way, was made in what, like eight years or s- 12 years or so? I mean, some insane-

    23. DS

      Crazy

    24. TF

      ... time span.

    25. DS

      And so then, first of all, I'm freaked out. I'm there. It's me, two other young entrepreneurs in their 30s, and they had both met Charlie before, and then I'm like 10 minutes in and I'm just like, "Ugh," like I just couldn't believe what's happening to me. I'm like, "That's fucking Charlie Munger over there."

    26. TF

      [laughs]

    27. DS

      And then you know he's looking at you because he's like blind, and so if he's looking at you like this, he's not looking at you. He's gotta go like this and this 'cause then he's gotta look through his glasses.

    28. TF

      [laughs]

    29. DS

      So you know when he's looking at you. And then my friend looks at me, he's like, "Get in here," like-

    30. TF

      Hmm

  37. 1:43:32 – 1:50:30

    Dealmaking lessons on Eddie Lampert’s superyacht.

    1. TF

      stock. Oh my God.

    2. DS

      [laughs]

    3. TF

      All right. We are gonna get to the things I promised, but-

    4. DS

      [laughs]

    5. TF

      ... I have to ask you, so in addition to smartest person, best business, what are some of your other go-to questions when you meet the fancy folks?

    6. DS

      It's who's the smartest person you know? What's the best business you know? I actually got to spend some time with Eddie Lampert. Eddie Lampert at one time was thought to be like the next Buffett.

    7. TF

      Mm-hmm.

    8. DS

      And he was mentored by Richard Rainwater. And I find Richard Rainwater really fascinating because Richard Rainwater has probably-

    9. TF

      Great name too.

    10. DS

      Oh, excellent. First, there was no biographies on him. He died rather young. He probably created more billionaire investors in America than any other person in direct mentorship. Eddie broke the record, I think in like the '80s or '90s, for like the most taxable income made by an American [laughs] and he was like super young. And so Eddie lives in Miami, and I was at his house.

    11. TF

      He was like, "Never again I'm moving to Miami." [laughs]

    12. DS

      No. That might be one of the best investments 'cause he probably paid $12 million for his house, and his house would probably sell for 150 million today 'cause it's on the island that Bezos lives on, and the house is beautiful.

    13. TF

      I'm sure he won't even notice it on his balance sheet-

    14. DS

      So-

    15. TF

      ... or in his life. [laughs]

    16. DS

      He, he's much more, like, out of the spotlight now and, but again, he's like one of these older guys, just very, very wise and, like, very quiet. He's like me, he's, like, introverted.

    17. TF

      Mm-hmm.

    18. DS

      Just, like, you go to his house, there's just books everywhere. He's got this insane yacht that I went on called the Fountainhead. I'll let people Google it.

    19. TF

      [laughs]

    20. DS

      It is insane.

    21. TF

      I mean, great name too. [laughs]

    22. DS

      Yeah, but same thing. You go on the boat, dude, and it's, like, full of books.

    23. TF

      Ran out of room at his house, had to buy-

    24. DS

      It's the weirdest-

    25. TF

      ... a superyacht for the books. [laughs]

    26. DS

      [laughs] It's the weirdest unintended hack ever to build a world-class network of just, like, read a bunch of history, and they'll come get you.

    27. TF

      Yeah.

    28. DS

      I've never sent a cold DM in my life, ever. I've never sent a cold email in my life.

    29. TF

      I had to hold one second.

    30. DS

      Yeah.

  38. 1:50:30 – 1:52:20

    David’s obsessive craftsman approach to podcast creation.

    1. DS

      I am obsessed with product. The fact that I work on my podcast for seven days a week, the fact that I hand-edit the transcript, MrBeast, he's like, "You're stupid. You need an editor. You need all these other things." And like, I just am obsessed. It's like, you don't work all your life to do what you love to not do it. I don't wanna outsource stuff. I like the craft of making the product. I'm very proud. Like, some people might consider this embarrassing. When Spotify, my Spotify Wrapped comes out this year, the number one podcast on that is going to be my own. I go back and listen to it. One, I think of it as a tool, right? I was on a treadmill in Malibu a few weeks ago listening to episode 221, which I think is a biography of Charlie Munger. I study Charlie Munger all the time. We forget how much we forget. I listen to this hour-long podcast. I'm like, "Oh God, he's got a lot of great ideas that I forgot." I'm not doing it because I like to hear the sound of my own voice. I also do it because do you think Kobe watched game tape? When I interviewed Michael Dell, really more of a conversation than an interview, but I listened to the Michael Dell episode that I just did a few months ago, and all I hear is the flaws.

    2. TF

      Right.

    3. DS

      All I hear is like, "You stupid idiot. You sh- used three sentences that could've been one sentence. That is not even interesting. Cut that next time." That's how I get better. I go back and listen to it. So I am obsessed with product. The people that I admire the most are like great products. It could be Jiro's Sushi. It could be the Spotify app. It could be... It doesn't matter. Shoes that I like. You know? I just love when people take what they do very seriously, and I like the craft of it, and I wanna dedicate my life to making a product that makes somebody else's life better. That is what drives me. I understand, and I have a bunch of friends that like the money, or like building the systems, if you wanna go back to archetypes, or just like having a big empire. I don't have any employees [laughs] .

    4. TF

      Mm-hmm.

    5. DS

      You know, you have three. I guess I have two technical subcontractors, you know, doing clips for me and thumbnails and stuff like that. But yeah, I don't, I don't have any desire for like a giant empire. I'm like a little craftsman in my little shed over

  39. 1:52:20 – 1:57:00

    Why David decided to begin a second podcast.

    1. DS

      here.

    2. TF

      So why do the new podcast? David Senra.

    3. DS

      Yes.

    4. TF

      Why do it? And we can use any number of different entry points here. So number one, why do it? You don't have to answer that as number one. I'm also curious where you see the podcast ecosystem. Is it early? Is it late? Is it oversaturated? Is it undersaturated? Et cetera. And then how do you diversify an interview-based podcast?

    5. DS

      Okay, so let's take the number one, the why to do it. I was resistant on doing it for years because I like to do one thing and I don't like to not focus, right?

    6. TF

      Mm-hmm.

    7. DS

      A huge thing... If you could summarize, you know, nine years, 400 biographies down to one word, what I've learned is focus. These people, whether they're psychos, nice people, different industries, they're remarkably focused compared to like-

    8. TF

      Mm-hmm.

    9. DS

      They're a different species than the current level of, you know, lack of attention spans that we have now that I think are getting worse. Focus is excessively important. If you look at how I spend my time though, right? We just talked about the importance of building a business that's natural to you. Half my waking time I would like to be completely alone, not in the, even the house with somebody else. Like alone in my... Just reading, thinking. I like solitude a lot to a scary degree. So that makes sense. Founders, you're reading books all day. That's, that's what you do. Like that makes perfect sense. When I'm not doing that though, if you look at what else I'm doing, I essentially do this data dump where I'm in silence half the day, and then I go out every night that I'm not with my family, I usually have dinner with another founder usually that I met through the podcast, and we talk for three, two, three f- There's no like... Some people are like, "Oh..." Really impressive people will send me like, "I would love to talk to you," and they like send me a calendar invite for 30 minutes. So I go, "Ah, I don't do thir-" Like, we're not even gonna start. We haven't even started.

    10. TF

      [laughs] Yeah.

    11. DS

      Like if that's what you think this is, like I don't care that you're a billionaire.

    12. TF

      Yeah.

    13. DS

      Like we're just never gonna meet ever. And it's always super long from the very first time. First time, I can mention all these people, we talked for a long time. So I'm doing this anyways. And for years people like Patrick were like, "You stupid idiot. You should be recording these. This is crazy."

    14. TF

      Mm-hmm.

    15. DS

      And so there's two things, to answer your question, that happened. One is the first time me and Patrick grab dinner in New York with Daniel Ek, okay? We talked for four hours.

    16. TF

      Mm-hmm.

    17. DS

      And we get in the car because we're leaving the city and going back to Patrick's house because I'm gonna spend the night there before I go back home, and the first thing Patrick says... And again, the piece of advice that Charlie Munger gave us when we were at his house, he's like, "Your job at your age is to build a seamless web of deserved trust with other people who are like you." He's like, "Everybody knows that me and Buffett, I met Buffett when I was 35, he was 28, but they didn't understand there's a bunch of other guys around our age that we'd built the same level of trust with and we did life with and did deals with forever. Most of them were dead by the time I met Charlie." And so relationships are very important, and Munger has a line that trust is one of the greatest economic factors in the world. I've never heard anybody else say that.

    18. TF

      Yeah.

    19. DS

      That's a truly unique idea.

    20. TF

      I agree with that.

    21. DS

      And so like there's a level of trust that I am very standoffish. People call me a turtle, like I get in my shell, right?

    22. TF

      [laughs]

    23. DS

      Once you've penetrated that, I have a level of trust that you want what's right for me. There's no like weird competitive vibes here. We're not secret adversaries. Like we just, I wanna see you win. And we get in the car and he's just like, "Goddammit, you need to record these."

    24. TF

      Mm-hmm.

    25. DS

      And he's like, "I've known Daniel for four years. You got more out of him in four hours than I did in four years." He's like, "I spoke 2% of the time. You spoke 49%. He spoke the other 49%." And he's just like, "There's nobody that can speak to the soul of the founder in the world that you can." And it's because he says something and it's not what he's saying, it's what Henry Ford did here and Henry Kravis did there and Jim Casey did over here. That's how my brain naturally works. So I was like, "Okay, that was interesting." And then part of the conversation was, you know, Daniel saying to take... I didn't, wasn't doing video.

    26. TF

      Mm-hmm.

    27. DS

      375 episodes because I didn't wanna be... I'm not doing it for fame. I'm introverted. And Daniel just saying in a very nice way What are you doing? Like, stop riding the fence. This is the game that you chose. And I have the data. Video obviously is important in podcasts. Like, you're lying to yourself again. You know, the importance of somebody telling the truth. I want people around me that check me. I don't want sycophants, you know? And I'll tell you the second person that influenced me that, that calls me and checks me all the time. And so that got in my mind for a while, and I was like, "Okay, that's interesting." And I get sad when I don't podcast. I would like to podcast every day, and I can't because I have to read an entire book before I sit down to make an episode. I cannot make more than 52 episodes a year. I just can't. I can't read. I- people are like, "You must read fast." No, I read slow, 25 pages an hour at most, and then I have to do all the other shit I just told you I had to do, [laughs] the highlighting and, like, you know how long this takes to like-

    28. TF

      Taking photographs.

    29. DS

      [laughs]

    30. TF

      Putting it into Readwise.

  40. 1:57:00 – 2:02:54

    The benefits of cultivating a purposeful aloofness about current events.

    1. DS

      And so then something that's also that's important to me is just like I'm not a political person at all. I don't even read the news. I will find out the important stuff. If there's a pandemic, I'll hear about it. If there's a war, I'll hear about it. Other stuff, no idea what's going on. I have no idea what's going on. I'm purposely aloof. But one thing that I am passionate about is that entrepreneurship is good for the world as long as you're spending your time building, 'cause all business is... You mentioned Losing Your Virginity by Richard Branson. He has the best description I've ever heard of a business. All a business is is an idea that makes somebody else's life better, and therefore, there's always opportunity because there's infinite ways to make other people's lives better. And so that's what I'm trying to do. And so another person I've become close with is Jared Kushner. We live in Miami together. We went and met for dinner, and Jared's, like, a really smart and, like, buttoned-up guy. And again, I don't pay attention to politics, so, like, the way I met him is actually he reached out to Rick, and it's like, "I'm a huge Founders fan. Can you contact, see if David would speak at my company off-site?" A lot of companies ask me to speak at their company off-site. I didn't know anything about Jared. All I know is that people on, on the internet like to argue about him because of the Trump stuff, but I judge people on how they are with me. This had to happen to you where you were like, "That person's great," and you deal with someone like, "Oh, that guy's terrible," or vice versa.

    2. TF

      Yeah, I've had both. Yeah.

    3. DS

      Yeah, exactly. So it's just like I'm gonna go into this. I'm not gonna do the research. I have no idea about all this stuff. I'm just gonna see how this is gonna go. And then we hit it off right away, and he was just like, "Try to pay me." I was like, "No, no, no. Like, I'm not... Like, it's in Miami. I can drive over there. I could talk about this shit all the time. I like talking about this." So, like, and then we just built a relationship and a friendship from that. We have similar interests. We meet for dinner one day, and it's right after basically he went and spoke at this conference in Miami, and he thought he was gonna go talk about his new fund, and he thought he was friends with the guy, and the guy's, like, selling tickets and making money off his name being there, and, like, it's not like you're paying the speakers. And the guy, like, essentially ambushed him and starts asking questions like, "How can you do business with Saudi Arabia?" They chop up Khashoggi and all this other stuff. And then before the talk was even done, his social media team was, like, clipping it and, like, sending it out in, like, press releases and stuff.

    4. TF

      What a mess.

    5. DS

      So I show up at this dinner, and Jared's always buttoned up and, you know, g- always got his shit together, and he's just like, "What the hell is going on here?" And as, by the time the dinner ends, it's everywhere.

    6. TF

      Yeah.

    7. DS

      And again, I'm like, this is weird that the business and tech press in America, they hate business and tech. They, like, cover things. I'm an enthusiast. I'm not a journalist. I'm not a critic. I read books all the time where I hate the person. You'll never see me do a podcast about it. I wanna talk about stuff I like, not things I hate. It's a weird thing to go through. Like, imagine waking up every day and your job is to, like, cover people that you secretly, like, wish you were. There's just weird stuff that, around this, right? And so we had this idea at dinner. I was just like there should be a place where, like, I'm not talking about sycophant. I'm saying, you know, Todd Graves, people make fun of him because he says that God made him good at chicken fingers and that he f- he's living a chicken finger dream and he thinks it's a mission. But I'll tell you what. He believes it. He's been offered billions. He owns over 90% of that company. He will never sell that company.

    8. TF

      Mm-hmm.

    9. DS

      He's not doing it for money. He's doing it because he wants to make money, and he does a lot of great things in the community, and I think people should know this, this guy exists, and his ideas should be spread. That's a good for the world. So those two things happened, and I'm like, oh, this is interesting. I have this weird base of knowledge. So the way Jared describes it is talking to you is like talking to 50 of history's greatest entrepreneurs at the same time 'cause, like, we'll talk about something, and same thing you see I do. And then Daniel's way of saying that, he's like, "You're like a LLM trained on history's greatest entrepreneurs with the temperature turned up 'cause you're crazy." [laughs]

    10. TF

      [laughs]

    11. DS

      And so it makes it, like, entertaining.

    12. TF

      I think that's no small contributor to why you have a diehard fan base. Like, it's the pulpit preacher kind of fervor that you bring to it.

    13. DS

      But I didn't understand that-

    14. TF

      Yeah

    15. DS

      ... until I thought about my childhood. When people say they go to church, that's not the kind of churches I went to. This is really gets me sad and where I was almost crying earlier. My mom deserved a better life. She didn't deserve to grow up with the monster of her father and the, frankly, the bitch that her mom was.

    16. TF

      Mm-hmm.

    17. DS

      The one thing that I remember about my mom's mom that she said to me was that I was a faggot.

    18. TF

      Hmm.

    19. DS

      That is literally the only memory I have. She was mentally ill. You'd go to her house. You know National Enquirer and, like, all those things that, uh... There's National Enquirer. There's, like, The Sun and all this other stuff-

    20. TF

      Right

    21. DS

      ... that you get, like, right when you go to the grocery store. She was, like, a hoarder, so she would, you'd go in the bathroom, and it had, like, stacks all the way up to the... She wouldn't throw them out.

    22. TF

      Yeah.

    23. DS

      But she read them like we read The Wall Street Journal. Like, you assume the stock is what they said the stock price is. She'd read it like, "This is true." Like, "Bigfoot is true. President..." This is, I was a kid. This is the memory. I was the age when President Clinton, when Clinton was in the White House, and she was convinced that Clinton was gay and his wife was lesbian.

    24. TF

      Hmm.

    25. DS

      And so she saw, like, conspiracy everywhere, and she would direct that at her grandchildren, which is, like, monstrous. And so my mom deserved better, and then the problem was my mom didn't have an education, and she was a very naive person, and so she turned to the church. But the church she turned to was like, do you know Benny Hinn is?

    26. TF

      I do know the name, yeah.

    27. DS

      Okay. That's, you come up there, and he blows on you, and you don't have leprosy anymore, or he hits you in the face, does this thing, and you can walk now. All this stuff was acting. They've caught these people over and over again. And, like, I remember my mom didn't have a bunch of money and her putting, like, a couple crumpled up dollars and giving it to them because she thought- This is like what she's gonna get in her life. And it's sickening to me now that that happened to her and that, you know, she fell prey to that, and that these people did this, and they have private jets, and they have all this kind of crazy... I'm sure there's some people that do that and they believe it. That's a different thing if they really believe it. I know that guy didn't believe. Like, he- come on, you didn't believe that.

    28. TF

      Yeah, it was a racket.

    29. DS

      And so, but then I didn't understand that, oh my God, that it [laughs] influences the way I make my podcast because it is like preacher.

    30. TF

      Mm-hmm.

  41. 2:02:54 – 2:08:30

    New show frequency/dynamic and how David plans to balance the burden of running two shows.

    1. DS

      So that's why I'm doing it, and then the other thing was like, I just like podcasting, and I can have a conversation every day. So we're gonna start out like every other week and then move up to every week, and then I wanna be having multiple conversations a week.

    2. TF

      Mm-hmm.

    3. DS

      That's what I wanna do because I'm doing it anyways. Let's just put a microphone there, and it's not an interview. Yeah, there's some questions I have for them, but it's like a conversation. The idea that I'm gonna do a business show interview and compete with Patrick, I think he's the best interviewer by far.

    4. TF

      Mm-hmm.

    5. DS

      He's so concise and perfect and like, he's just really good at it, and I like to talk. I wanna talk 49% [laughs] of the time.

    6. TF

      How will you balance the two shows? 'Cause it seems like Founders podcast takes a lot as it is.

    7. DS

      Yes.

    8. TF

      One of the benefits of that format is, now this might put a cap on growth to some extent, but if you're not playing the video game, it removes a lot of complexity, right? You don't necessarily need to travel. You just read. You enjoy your solitude. You do some long form audio. You can have notes in front of you. You can be picking your nose like-

    9. DS

      [laughs]

    10. TF

      ... as you take a deep breath. There's a lot of flexibility there. How are you going to balance the two without sacrificing Founders, like snuffing out the magic X when you're working on Y?

    11. DS

      That's a great question, and it's something I was like very concerned with, and that's why I said no for so many years. And so then you think, well, like if you said yes, then how would you do it? Instead of just blankly saying no.

    12. TF

      Mm-hmm.

    13. DS

      And there, there's a secret of dealing with me that everybody that knows me for a long time realizes, and essentially like it's like water on a rock, okay? This has literally happened multiple times. So let's say like Patrick or Sam Hinkie would be like, "I have this idea," and immediately I'd be like, "That's the stupidest idea I've ever heard," and I'll be like really like aggressive and angry. Just like, "Stupid idea. Terrible idea." Then they mention it like two weeks later. Now it's just, "Dumb idea."

    14. TF

      Mm-hmm.

    15. DS

      Mention it again like a few weeks later, silence. Then a few weeks later, I'm like, "Hey guys, I have a great idea." [laughs]

    16. TF

      [laughs] It's that idea.

    17. DS

      It's that idea. [laughs] So-

    18. TF

      The slow bake

    19. DS

      ... [laughs] then they just like, they know. They're just like, "Okay, I'm just gonna... It's just water on a rock. I'll get to it, but it's just gonna take a while."

    20. TF

      Mm.

    21. DS

      So, and now the problem is now I've said that. They know that, and then you have other people that have to deal with me that like, I'm very difficult to deal with obviously.

    22. TF

      Mm.

    23. DS

      You are too. I think like that's the one thing we can bond over.

    24. TF

      [laughs]

    25. DS

      And we don't mean... I, you're not trying to be mean. Just like-

    26. TF

      Yeah

    27. DS

      ... it's just a part of our personalities. And so the answer to your question is Founders is a one person. So like I read, I read research, I record, I set my own mics, I do all the editing, I hand do the transcripts, I do everything. The only thing I outsource is that I think I have, the clip guy I have is a little genius, a young kid living in Paris. His name's Maxim. He's incredible. And then I have somebody now because I have to play the YouTube game, which I hate-

    28. TF

      Mm-hmm

    29. DS

      ... and I refuse to do, and all this other, you know, the YouTube thing, like-

    30. TF

      Yeah. Yeah.

  42. 2:08:30 – 2:10:28

    Rockefellers “secret allies” strategy

    1. TF

      Mm.

    2. DS

      Books are made out of books. Everybody has read Titan by Ron Chernow. In the bibliography of that, there's a better, the best Rockefeller biography I've ever read, and I have like eight at the house I haven't read yet. I, I collect like obscure Rockefeller biographies that I'll eventually get to.

    3. TF

      What's your favorite one?

    4. DS

      It's called John D.: The Founding Fathers of Rockefellers by David Freeman Hawk.

    5. TF

      Better writer than, uh, titler, I guess.

    6. DS

      Yes. 250 page instead of 800, but all about what you really wanna know. You don't wanna know about where his grandfather was born. You wanna know how he built Standard Oil.

    7. TF

      Mm-hmm.

    8. DS

      And there's this idea in there that I've used called secret allies. And so he's... This is gonna answer your other question about podcasting, where he's at the beginning of the oil industry. It's the very beginning, and he's there. No one-

    9. TF

      Rough and tumble time.

    10. DS

      Yeah. No one knows shit about oil refining, so what does he do? He goes and builds a network of secret allies with other oil refiners, and they eventually do something that's even more nefarious, which they, they start something called, like, the Oil Refiners Association of America or something, and then he gets himself elected president to that. It's like if, if we had a podcaster union and we all... I'm president of the podcaster union, and then I go to you and like, "Tim, what's your downloads this month? Okay, and how much are you charging for ads? And then who's your next guest?" And he's getting all this data.

    11. TF

      Mm-hmm.

    12. DS

      So then he sees, that's a joker. I don't have to... He- that guy's already out of business. He doesn't even know yet.

    13. TF

      No, we don't have to worry about that guy.

    14. DS

      Yeah. That guy's a killer. I need to buy his company and make him a partner. And so this idea of secret allies-

    15. TF

      [laughs]

    16. DS

      So I'm obsessed with podcasting, and so what I would go do, I'd go around and I would talk to any podcaster who would talk to me.

    17. TF

      Mm.

    18. DS

      And we'd talk about everything, downloads, ads, who are you selling to, how are you selling, who are you using for editing, even clips.

    19. TF

      Maybe that's the spider sense I got.

    20. DS

      No. [laughs]

    21. TF

      [laughs] I'm kidding. Just kidding.

    22. DS

      No, 'cause I give.

    23. TF

      Yeah, yeah.

    24. DS

      I give-

    25. TF

      Yeah, I know. I'm kidding. I'm kidding.

    26. DS

      There's, there's people literally, like-

    27. TF

      [laughs]

    28. DS

      ... they'll even tell you, like, there's podcasters that literally, like, I took an idea from one podcast and gave it to another podcast 'cause that's the whole thing. I don't collect it and hold it.

    29. TF

      Yeah, yeah.

    30. DS

      We spread it around, and they've made millions and millions of dollars from these ideas.

Episode duration: 2:42:16

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