David Senra, creator of the Founders Podcast, joins Sam and Shaan to explore what separates the world’s greatest from the merely good — arguing it’s not 10% better but orders of magnitude different. The conversation covers David’s obsessive approach to reading, the concept of “constant refinement of association,” his personal journey from 1,500 downloads to building relationships with the world’s elite entrepreneurs, and why he doesn’t optimize for happiness but for impact.
Speakers: Sam Parr (host), Shaan Puri (host), David Senra (guest, Founders Podcast)
Introduction: The Gap Between Good and World-Class [00:00:00]
Shaan: David Senra. The guy’s name is David Senra. He’s got a podcast called Founders. To even get on Founders Podcast, you have to be so good at your job that somebody wrote a book about it. That’s an insanely high bar.
David: It’s almost like it’s an obsession.
David: It is. I’m addicted.
Shaan: I’ve known you now for — I don’t know — four or five years. I think you are crazier now than you were.
David: I’m not balanced. I don’t think I can be balanced. I don’t think I want to be balanced. I want to be the best in the world at what I do. People are like, “Oh, 10,000 hours.” I’m way past that. Way past that. So of course I’ve changed. I’m not doing this to stay the same.
The difference between the world’s greatest and pretty good — it’s not a little bit better. It’s not 20% better. It’s like a thousand times better. And that is hard to grasp.
Mediocrity is invisible until passion shows up and exposes it. I’ve become intolerable for people that are casual. And I don’t even know why I’m like that.
I think I was lying to myself for a while that I don’t need anybody else. I wanted professional success to say: I was born in the wrong environment and I will prove to you that I am not like the rest of these people. It’s almost like a revenge for being born.
Sam: Are you a happy person? I don’t think you’re happy.
Eliud Kipchoge and the Magnitude of Greatness [00:01:30]
Sam: Okay. So you have to look this guy up — Eliud Kipchoge. You have to see what he looks like. He looks more like a gazelle than a human being. Because the thing about world-class athletes and runners is you see them exerting themselves, wearing their running gear, and you’re like, “Yeah, he looks amazing.” But then you see him up close and you’re like, “Oh my god, that person is so much skinnier, has so much less body fat than the average person. How on earth are these two human beings both human beings?”
He runs the marathon in something like 2:01, which works out to about 4:36 per mile. Crazy fast. And what we were saying was: the difference between the world’s greatest — the best there ever was — and pretty good? It’s not a little bit better. It’s not 20% better. It’s 10 times, 100 times, a thousand times better. And that is hard to grasp. Do you agree?
David: Yeah. I mean, you asked me right before we started recording — you saw what I was doing and you said, “What are you thinking about?” And I was like, “I’m thinking about how this looks.” And you said, “But does that matter?” I was like, “Everything matters. We’re trying to be the best in the world at what we’re doing, so we have to take everything very, very seriously.”
I think the only thing I’m obsessed with — and actually one of the best pieces of advice I ever got, that I won’t shut up about and think about literally every day — is this idea of constant refinement of association that my friend Jared Kushner told me. And Jared is unbelievably honest.
There’s a great line — I just finished reading Bruce Springsteen’s autobiography, and he talks about his deep friendship with Jimmy Iovine. He says: you want Jimmy in the room because he’ll tell you the truth. Like everybody around Bruce is kissing his ass, and Jimmy’s just like, “This album sucks,” or “This is great.” Trust his judgment. And Jared’s like that too — if he’s your friend, he’s very kind, but he’ll say, “Hey, what you’re doing is not good enough for you. This person is not good enough for you. Be careful with this.”
So this concept of association is important because as you keep getting better at what you do, you get access to people that are great at what they do too. There are a lot of commonalities between them. And once you’re exposed to that — I always have this line: mediocrity is invisible until passion shows up and exposes it. I’ve become intolerable for people that are casual — the way they push their work, the friends they choose, just anything that is not them striving for excellence. And I don’t even know why I’m like that. It’s just: I want to be, I have to be the best in the world at what I’m doing.
Nature vs. Nurture: Born This Way or Built by 400 Biographies? [00:05:00]
Shaan: Were you like that, or did you become like that because you’ve studied 400 biographies of greatness?
David: That’s a great question. I don’t know. Michael Dell has this great line in his autobiography — he’s 19 years old, in his dorm room at the University of Texas, he’s got $1,000, and he’s like, “I’m going to compete with IBM.” That is delusional. IBM at the time was the most valuable company in the world — the first company to get to a hundred-billion-dollar market cap in history. And you have this kid saying he’s going to compete head-to-head with them. The next line is: “Was I a little full of myself at 19? Sure, I was. I think you have to be to do anything special.”
So I always had this deep, delusional self-confidence and default optimism — if I focus on something, I will figure it out. But I also think it’s impossible to separate. I’ve been doing Founders Podcast for almost 10 years. I think I’m at like 407 books by now. That’s hundreds of thousands of pages. People are like, “Oh, 10,000 hours.” I’m way past that. So of course I’ve changed. I’m not doing this to stay the same.
Shaan: I’ve known you for four or five years and I’ve listened to you for longer than that. I think you are crazier now than you were. I think you are more obsessed now than you were.
David: Sometimes I think I should shut up and not say the things I say on podcasts. I don’t like having a filter. I don’t like having two different sides of me. It makes me fundamentally uncomfortable.
I just did this on Tim Ferriss’s podcast. Tim didn’t tell me what we were going to talk about — other than his team said, “Please tell David not to curse so much.”
Sam: That’s what I told you five years ago.
David: And I hesitated for half a second, thinking: man, I should not say this stuff. And I just let it go. Since then, I got a call from the founder of a public company — relatively young, wildly successful — and he was just like, “Hey, I listened to your Tim Ferriss interview. I know exactly what you’re talking about because I went through that too.”
So to answer your question: am I crazier, more intense? I think I was lying to myself for a while. If you look at episode 222 of Founders Podcast — Ed Thorp — it says in parentheses “my personal blueprint.” Ed Thorp is a legitimate genius. I am not a genius. Whatever he directed his talents toward, he was going to succeed. And what I liked about him was he was a real, balanced person.
Ed Thorp: The Blueprint David Rejected [00:09:30]
David: Quick TLDR of his life: he was the person who invented how to count cards in blackjack. He was a mathematician and a professor for a long time.
Shaan: He wrote a book called Beat the Dealer in the 1960s. Sold millions of copies. He started the first quantitative hedge fund of all time. He was one of the first investors in Berkshire Hathaway. He meets Warren Buffett when they’re both in their 30s, gets in the car, and says, “That guy’s going to be the richest person in the world one day.” And he invented the world’s first handheld wearable computer with Claude Shannon, the father of information theory. How did one guy do all this?
Sam: He’s like the Forrest Gump of finance.
David: That’s a great way to think about it. But he also came from a messed-up family. He got into weightlifting and taking care of his health before there was anything like bodybuilding. He figured out in college: every hour I spend in the gym working on my health now is one less day in the hospital when I’m 80 or 90. He went on Tim Ferriss’s show and you look at him — people guess he’s 60, and he’s 92.
His whole thing was: I want a balanced life. Work nine-to-five, spend time on his health, his family, have fun. Once he made more money than he could ever spend, he stopped trading time for money. He’d pass on opportunities — “Oh, I could make $30 million on this” — and just say, what’s the point?
For a long time, after reading maybe 200 of these books, I thought: he’s the outlier. Most of these people are singularly obsessed with their work. And so for a long time I was lying to myself: “Yeah, I want a balanced life.” And it’s just like — no. I’m not balanced. I don’t think I can be balanced. I don’t think I want to be balanced. I want to be the best in the world at what I do.
I narrowly define that. That’s what drives me. That is when I feel comfortable. Maybe I’ll change in the future, but I am fundamentally uncomfortable not working toward some kind of professional goal.
How David Reads and What He’s Looking For [00:15:00]
Sam: I read a lot — almost a book a week. My philosophy toward reading is: I want to see what worked for the winners I love, what strategies they used, and what mistakes they all made — the common flaws. And I just want to avoid that.
How do you become sensitive enough, when you read something, to know that that’s a point worth remembering? I’ve read things and I forget them. I love the American Revolution and I’ll reread books and be like, “I didn’t even remember this.” You do a really good job at recall. You bring the points of the story that actually matter. How do you develop that sensitivity — to see what’s important, what isn’t, and then use it to change your life?
David: I’m a big believer in intuition and constant refinement of your own taste. I’m sure I didn’t have that skill in September 2016 when I started — not nearly to the degree I have it now.
Right before Kobe Bryant died, he was asked about what he sees in Steph Curry that makes him such a formidable competitor. And Kobe said: there’s a calmness about him. And when you match that calmness and belief in his skill set with his intense desire and work ethic to practice, that is a very dangerous combination. What Kobe was referring to was Steph saying, “People always ask me what I think about when I’m shooting.” And he goes, “Absolutely nothing.”
So I don’t overthink this. I read the book. If something speaks to me — it’s all intuition. This line is jumping out at me. I’m going to underline it and jot down exactly what came to mind right now. Do not overthink this.
We don’t see the million times Steph was alone shooting threes. I always say: the public praises people for what they practice in private.
David: The other thing about taste — when I talk to people who are really great at what they do, and then to people who want to be great but aren’t yet, they’re trying to figure out: why am I not breaking through? It’s because you’re not actually interested in this. You are lying to yourself. I am intensely interested in this.
You could ask my partner Rob — we go through this all the time with the new show. Someone will suggest a big name and I just don’t care. The only way I’m going to do this for the rest of my life is if I’m doing it for the right reasons. I cannot overcomplicate things.
Munger has this line about how the hardest thing is to remember why you set out doing what you’re doing and to keep things simple for a very long time.
So the way I think about it: Founders is the books I’m intensely interested in reading — not books I think are going to get downloads. There have been times where everyone says, “Read this book.” I read it. I hate the guy. I literally throw the book across the room. I’m not going to spend a week in that person’s mind.
And the new show is the people I’m intensely interested in having conversations with. I’m interested in people that have singular careers — doing what they do in a way that’s completely natural and authentic to them, with an inner scorecard. They make decisions that may not make sense to you but make sense to them.
The Inner Game of Tennis and Self-Criticism [00:20:30]
Sam: Have you read The Inner Game of Tennis?
David: No, but everybody tells me about it.
Sam: The guy’s name is Tim Gallwey. I think he wrote it in the late ’60s or ’70s. He was a tennis instructor trying to get his students to play better. He developed this idea of Self One and Self Two. Self One is the critic — when you hit a ball, you say, “Shit, that was horrible. I got to move my hand this way.” Self Two is someone who doesn’t listen to the brain but listens to the body. You say: I’ve practiced this a thousand times, just like Steph Curry. I don’t need to criticize myself. Instead, I’m going to be objective: let’s try moving the hand a little this way and see what happens. You just feel it.
The idea is you listen to your body more than your brain. Very similar to what you’re saying about being simple and following intuition. Bill Gates wrote the most recent foreword to the book — it was launched in the ’70s, republished, now a business classic.
The criticism thing — me and you have talked about this a lot in private. We were both maniacally driven to fix ourselves and achieve financial success, and a lot of times that doesn’t come from a positive place.
David: Yeah. The way I see it — I build businesses because I feel like I’m not good enough. And I try to fix myself because you have to fix your personality to build a great company.
Mine is a little different. There’s this movie called Tombstone — one of my favorite things. I watched it as a kid over and over again. There’s a line where Doc Holliday and Wyatt Earp are true friends, and Wyatt is about to have a life-or-death duel with Johnny Ringo. They’re talking about what drives Johnny Ringo. The performance by Val Kilmer is incredible. He says: people like that have a giant hole in their heart that no matter what they do, they can’t fill.
Then Wyatt asks: “What does he want?” And Doc says, “Revenge.” “Revenge for what?” “Revenge for being born.”
And I think what drives me — I wanted professional success to say: I was born in the wrong environment, and I will prove to you that I am not like the rest of these people. I knew that since I was like six. I felt very different. And I’m going to do this for myself, but you’re also going to see that I’m not going to wind up like these people. It’s almost like a revenge for being born in the environment that I was in.
Now, the self-criticism — you see this with a lot of high performers — constantly, overtly negative. What I’ve changed to now is: that drove me to work all the time, to find a craft I could be really good at. That has already happened. So it was useful back then. Is it still useful today?
Brad Jacobs — I think the third person on the new show — has more years of experience as an entrepreneur than I’ve been alive. The amount of information they can transfer to you in an hour-long conversation, in a sentence, is not something you’re capable of unless you have this hard-earned wisdom from experience. And so much of his new book is about reframing negative thoughts into positive ways. He realized: when I was just negative and beating myself up, I was not as effective. I thought that was a tool. It wasn’t a tool.
What I’ve been thinking about a lot lately: that negative inner monologue served me back then. It doesn’t serve me now. Learning is not memorizing information. Learning is changing your behavior.
Sam: That’s the hard part — in general, people don’t change. Robert Greene has this great line: assume most people won’t change.
David: Most people — I’m not trying to be most people.
Sam: But we still have that in us. You have to fight inertia.
Bruce Springsteen: Work, Love, and Therapy [00:26:00]
David: So we were talking upstairs — you’re a Bruce Springsteen fan. His autobiography. I would highly recommend people go watch the movie Deliver Me from Nowhere. I thought it was going to be a standard biopic. That’s not what it was. It was about a guy who had an unbelievably tumultuous childhood that funneled that pain into an unbelievable work ethic to get him what he thought he wanted most — being a rock star. And then right after he hits that, after years and years of struggle, he plunges himself into deep depression.
What he realizes is: his childhood was so messed up, it didn’t give him the ability to form stable, loving relationships with women. What he desperately wanted was a stable relationship, to have kids, to raise his kids and break the chain his parents left him with. And yet — he’d fall in love with a woman and then think: something’s wrong with her. If she loves me, I must be unlovable. So he’d run away, start dating somebody else, over and over again. Until he ends up in therapy.
He basically says: my life is going to be like this — I’m going to be world famous, I’m going to be wealthy, I’m going to have a job I love, and I’m going to be depressed and miserable.
The book is 600 pages long. The first half, you think you see where it’s going — and then this curveball: life is more important than work.
What Bruce was figuring out is that every human wants relationships — whether romantic or a true friend, somebody who understands you, that you can do life with. And I now have a friend group that is crazy because of how high quality they are in all areas of their life. Almost every single one of my new friends has come from the podcast. In some cases they’ve become best friends — people I’ve spent years getting to know, hours and hours talking to. And I realized: relationships are really important to me in a way I didn’t understand before. Maybe I was lying to myself about this.
And then why I bring up the Bruce thing: he’s messing up at something he deeply desires, yet he’s smart enough to realize what tools he needs to fix it. Because if he doesn’t fix it, he’s going to have another 40 years of being miserable. So he changed his behavior. That means he learned. You’re not learning if you didn’t change your behavior.
Finding Your Passion Early — and the Envy That Creates [00:31:30]
Sam: You know what’s crazy? Every time I listen to your podcast, I have envy — not because of people’s success, but because a lot of them found their passion very early in life. Whenever I go to concerts — I’ve loved Green Day for years — Billy Joe Armstrong will play a song he wrote when he was 15. And I’m like: how fortunate are you that you were able to create stuff at 15 that’s still relevant to you in your 50s?
One of my favorites you’ve done — the Luxottica guy. What’s his name?
David: Oh yeah. Del Vecchio.
Sam: Basically this guy started a sunglass conglomerate, built a monopoly, an $80 or $100 billion company, tried to pass it on to his sons, make it a family dynasty — but there’s a ton of darkness, with family and just being generally angry.
David: Like an orphan.
Sam: Yeah. He had a lot of darkness.
David: But he never dealt with it. I just gave you the example of Bruce — Bruce said, “I’m not going to let this continue.”
Sam: Well, he dealt with it at the end. At the end of your episode you said the thing he wished he did differently was how he treated his children.
David: Yeah, but on the episode I said: I don’t believe him.
Sam: Right, you said that. But what I do envy of him and many of the others is that they found their passion early.
David: I could see that. But I was 32 when I found what I do. Really.
Sam: Bruce Springsteen was 15. Kobe was like 11. Del Vecchio was what, 17?
David: 32 was young. But the fact that you find it at all — this is why, when you ask why I’m taking everything so seriously: I understand how rare it is for somebody to make a living doing something they love. This is why I hate when I see people engagement farming and giving advice like, “The worst thing you can do is work on what you’re passionate about — just start a trash hauling business.” And I’m like: no, man. It’s the best thing in the world. It’s excessively rare. And if you find it, you should do everything possible to hold on to it and not mess it up.
Michael Dell, Jimmy Iovine, and the Four Ways People Destroy Success [00:36:00]
David: There’s a piece of advice I got from Michael Dell. Before we recorded together, we spent five hours talking. He told me: most entrepreneurs sabotage themselves. You’re not taken out by a competitor. You do something where you’re having success and then you go to sleep on a win and wake up with a loss.
Jimmy Iovine — he’s in this documentary called The Defiant Ones, one of my favorites. He had this crazy 50-year career. And one of the things I learned from him was the importance of actually having a full life with crazy experiences.
He did an episode of Rick Rubin’s podcast in 2023 — it was the best single podcast episode I listened to that year. I not only want to be really great at what I do, but I want to have a very full life.
Jimmy was kind enough, when I did a Founders episode on him, to invite me to his house. The guy has more practical knowledge in his pinky than I have in my entire body. And he’s like: most people cannot handle success. He’s been around super-talented people, legitimate geniuses, and they destroy their lives. I’m not interested in being successful for a year or five years. I want to do this until I decide I’m going to stop. So his whole thing was: there are basically four ways people destroy their success.
Sam: What are the four?
David: First: drugs. Heroin, pills, all of that. I don’t do any drugs. That’s not going to happen to me.
Sam: Did you see the Eddie Murphy documentary?
David: No. Everybody keeps telling me about it.
Sam: Oh, it was so good. One of the main things — he’s been famous since he was 16, on SNL at 18, doing movies at 21. He said: I’ve never done drugs. And that’s one of the main reasons he is what he is. He’s going to be relevant to number three on your list.
David: Number two: alcohol. Could destroy your life.
Three: women. They attract the wrong kind of women. Fall in love with the wrong women. Let the wrong women into their lives.
Sam: Like Bill Belichick? You see what he’s doing now?
David: He’s with a 24-year-old or something.
Sam: She just calls the shots.
David: It can distract you. You want high-quality people around you in every single domain — friends, people you work with, people you date. High-quality people. It’s the most important decision you make in your life, the people you let in around you. People are way too casual about this. I can be very ruthless in this domain.
And then the fourth: megalomania. You start to think you’re successful because of you and not the work you put in. You start believing you’re a god, everyone should praise you, and you become completely disassociated from reality.
This is why it’s very dangerous to let a numbers-driven metric become the reason for your existence. I talk to founders all the time — “I want to build a trillion-dollar company, I want to be the first to a hundred million ARR.” And I’m like… none of history’s greatest entrepreneurs made that their primary reason for existing.
Sam: I’m calling you out on that. When I talked to the RAMP founders — they’re the best of the best — they said, “Our goal is to get to a billion-dollar valuation in 18 months.”
David: That was not their primary goal.
Sam: He said that was his goal.
David: Oh, that’s different from making it the reason you exist. Wasn’t I there with you in that office?
Sam: Yeah. And he said it a bunch of times — like, “I thought it’d be cool if we get to a billion in valuation.”
David: Okay. Their experience with Paribus beforehand was what gave them the insight into founding RAMP — that’s a longer story. But my point: I’m hugely skeptical when there’s some external metric where you’ll only be happy if you hit it, and that is the reason you’re doing this.
Mine is just: I want to make things I’m proud of, things that are good, things I put out into the world that add something. And never confuse — someone saying “I like what you do” means they like the work. They might like you as a person too. But never confuse it: they don’t like you. It’s the work. And once you stop putting in the work, everything else goes away. That’s how the megalomaniacs fail — they think, “I’m so talented I just show up, everything turns to gold.” They stop practicing. And they treat people like objects.
How to Find Your Life’s Work at 19 [00:43:00]
Sam: If you had to teach someone who is 19 how to find their life’s work — based on reading 400 biographies and now talking to dozens of successful entrepreneurs — what would you say?
David: My problem is I think at that age I wouldn’t have taken anybody’s advice. I’m only in the last few years been open to letting other people mold my mind.
There’s this great line — a 21-year-old kid comes up to Mozart and says, “I want to know how to write a symphony.” Mozart says, “You’re too young.” The kid says, “But you wrote symphonies when you were 14.” Mozart says, “Yeah, but I didn’t go around asking people how to do it.”
There’s something in there — you feel like somebody else has the answer. That doesn’t mean you shouldn’t ask for advice. I don’t think there’s anything magical I would say that would put them on the right path. You need to spend a lot of time thinking about what you actually believe.
A lot of people just lie to themselves over and over again. I had a long conversation last night that started with: “What’s the lie you’re telling yourself?” My lie — I’ll tell you right now, even though I’m probably sharing too much publicly — is that I don’t need anybody else.
Sam: That’s a lie.
David: That’s a lie I’ve been telling myself for a very long time. I learned that from the relationships I’m having now, realizing: you’re doing that because it’s a defense mechanism, not because it’s actually true.
So for a 19-year-old, I’d say: take the time to figure out what you actually want. That’s very hard to be truthful about. The one way I’ve found it is to just follow ungovernable curiosity. I cannot tell you why I like to read. When I started my first podcast, I thought: it’d be cool to build a life where I just get to read all the time. That sounds ridiculous, but it actually worked.
And then you just follow this. We recorded with Todd Graves — the guy from Raising Cane’s. People were like, “Why do you want to meet him? He sells chicken fingers.” I was like: because he’s been doing this business for 30 years. He built the first store by hand. He had no money. He had to risk his life fishing off Alaska to find financing because nobody would give him money. He worked as a boilermaker, highly leveraged, almost went out of business multiple times. He did all of this because he had his chicken finger dream. That’s what he calls it. Hasn’t changed his menu in 30 years.
So we fly to Baton Rouge. The conversation is incredible. We record for two and a half hours. Then we spend another two and a half hours one-on-one together after.
Sam: Was he any different in person?
David: No. Because these people — and he listens to the podcast, so he understands who I am. This is what I meant: I don’t make media. I’m building relationships.
Sam: He might be a top-ten person I’ve listened to on your podcast.
David: He’s incredible. And so this is the point about following the curiosity. I go back to the airport, call Sam Hinkie, he picks up, and I say, “I’m in big trouble.” He says, “What’s going on?” I say, “I am already wildly addicted to having these conversations.” I say, “I’ve never done ecstasy, but this is how I feel right now. I am high. I am wired.” This guy — three decades of experience, 915 stores, the company’s worth over $20 billion, he owns 90% of it, growing faster in year 30 than it ever has in its history, and he still has trouble sleeping because he can’t wait to wake up and get back to work. You get this download of information and energy that just made me euphoric.
Board of Directors: Dead Edition [00:50:00]
Sam: Who would be on your board of advisors? Six people. Living or dead?
David: Let me do dead first because that’ll give me time to think about living.
Rockefeller built the greatest company ever created. Charlie Munger told me to my face that he thinks Rockefeller built the best business in history.
Sam: I think he’s one of the few tycoons with essentially impeccable character and amazing success. I think he’s the best.
David: Debatable on impeccable character. He did lie on the record a bunch of times. But in general I think he was an ethical, honest person — got a little strange in his later years. I collect obscure Rockefeller biographies. I have one at my house I haven’t done an episode on. It’s 1,700 pages long, in a big binder.
Sam: He was a weirdo when he was like 90, giving people nickels and stuff.
David: Yep. But undeniably one of the best businesses ever created.
Munger would have to be on it — he’s dead now, unfortunately. I think he’s the wisest person I’ve ever studied. If I could only learn from one person, it’d be him.
Edwin Land — founder of Polaroid, patron saint of the Founders Podcast. He was Steve Jobs’s hero. He invented instant photography, monopolized the entire industry. One of the last great American technology companies whose patents were never beaten. Steve Jobs met Edwin Land when Steve was 25 and Land was 72. Steve said spending time with him was like visiting a shrine.
I actually had lunch with a friend yesterday and she told me: you need to take a minute to think about what’s going on in your life and the fact that you have this ridiculously incredible life because of the people you have access to.
Sam: Do you ever write this stuff down? Like a journal?
David: No. I run from my past. I don’t like thinking about it.
I just spent time yesterday with a 71-year-old guy who looks like he’s going to do his first-ever podcast interview with me. He just sold his company for $60 billion. In an hour he transferred more knowledge to me than I would get in weeks talking to a young startup founder.
Edwin Land did the same thing for Steve Jobs. Steve basically patterned Apple off of Polaroid. A lot of people don’t understand that. You can go watch Steve’s product demonstrations — the table and chairs on stage are the exact same ones Edwin Land used for Polaroid demos. If you’re not studying history, you don’t have this basis of knowledge in your head. You don’t know what you’re looking at.
This is why we’re wasting time watching short-form videos all day, being obsessed with the news, following X — that stuff is garbage. Read books, talk to amazing people, try to apply what you’re learning to be a better human. And then the better human you are, other better humans will open up to you. There’s a virtuous cycle.
Sam: You have three more.
David: Rockefeller, Munger, Edwin Land, obviously Steve Jobs — he built the most successful consumer product of all time.
I’ll say two things about Edwin Land. His personal motto was: don’t do anything someone else can do. That demands differentiation. When you listen to Founders, it’s a very weird show. You can read books and make a solo podcast, but you’re not going to make it like that. It’s a very weird thing. Even the way I’m doing the new show. Everybody says, “This guy interviews weird.” I’m not interviewing anybody. I am having conversations. What you’re hearing on the show is exactly what you would hear if we weren’t recording. This is the stuff I have.
Everybody who’s been on the new show besides James Dyson has listened to the Founders Podcast. Some of the messages I get: “You talk too much, you interrupt, you should do it like this other guy.” We just did 400 episodes about people who built phenomenal careers by being differentiated. And now you’re like, “Don’t be differentiated”? The differentiation I have compared to other podcasters is that they haven’t read 400 biographies about history’s greatest entrepreneurs. I spend time with Daniel Ek all the time. I just saw Michael Dell again last week. I promise you they don’t want me to not talk. That is not what they want.
So: don’t do anything someone else could do. Very simple sentence, very profound insight if you actually apply it.
Sam: Your recall is so good.
David: I wasn’t born with that. It’s work. Ten years of reading, then rereading, building my own database. I’ve done all kinds of things no other podcaster does. I forget everything all the time — but I don’t forget something if I’ve read it 15 times.
Sam: I was up in your room and I took a photo of your book — the Brad Jacobs book. I just wanted to see what you were underlining.
David: And?
Sam: You had underlined so much stuff. So many notes in there.
David: Because I love what I do. And if you love what you do, you’re going to do things not for financial reasons but because you want it to be great. I am killing myself over an edit right now. The episode I’m working on is probably four days late and I still don’t have it. I feel uncomfortable — but I know that’s a good feeling. Because when I get on the other side, it happens.
I did the episode called “How Elon Works.” I think it’s the most downloaded episode of Founders by far. And I remember — it was supposed to be out on Sunday, it’s not coming out. But no one’s going to remember if it came out four or five days late. They’re going to remember if it was great or not. Spending that extra time and sitting in confusion is a good signal. It means I care. I’m trying. I will find my way there.
Edwin Land’s Second Lesson: Anything Worth Doing Is Worth Doing to Excess [00:58:00]
David: Let’s go back to Edwin Land for a second. He says — and this is where I admitted I was lying to myself about wanting a balanced life — “There’s a rule they don’t teach you at Harvard.” He knows, because he dropped out of Harvard twice. He says: “Anything worth doing is worth doing to excess.”
I can’t hold myself back. I have to take things as far as they can go. That’s why I can’t do many things. I essentially can just do podcasts, take care of my health, and build relationships. That is all my 24 hours. I can’t do anything else.
So — Rockefeller, Munger, Edwin Land, Steve Jobs. I don’t think I need the other two. I like fewer, deeper relationships. I tend to talk to the same people over and over again. You could talk to a thousand people a year if you wanted to. I want to genuinely know who people authentically are, and I want them to know who I authentically am. Skip all the noise and get right to the actual stuff.
I want to talk about your relationships with women. I want to talk about the guilt you have being on the road all the time as a dad. I want to talk about the stuff you’ve been lying to everybody else about. That’s the only stuff I’m interested in. I cannot have superficial conversations.
I remember once a billionaire reached out and said he’d love to talk. I got looped in with his assistant, got a calendar invite for 30 minutes, and I thought: we’re not even going to get started in 30 minutes. This isn’t going to work. Tell me when you have more time.
Regrets of the Ultra-Successful [01:02:00]
Sam: What do you think would be the biggest regrets of all the people you’ve talked to? Top three?
David: This is where I don’t necessarily believe them. Sam Walton — he’s writing his autobiography as he’s dying. He’s got cancer all over his body, in immense pain. He took some of the last time he ever had and distilled what he learned from his 50-year career. I think it’s one of the top five entrepreneur books of all time. It’s such a gift to future generations that he did that.
He says: yeah, I missed parts of my kids’ lives, I was working a lot. But he also says: if I did it all over again, I would do it the exact same way.
And I think a lot of people feel that way. They get to the end of their life and they’re nostalgic, they think: what would I change? But they actually did exactly what they wanted to do.
Even Buffett says in The Snowball that whatever he did to push his first wife away, he’d go back and do differently. Maybe. I don’t know. I think he did exactly what he wanted to do. Maybe in that case he’s right — he was truly in love with her and he messed that up. I could see that being a true regret.
I think a lot of these people have a hard time accurately assessing their own regrets.
Sam: There’s this great book called How to Get Rich. Have you read it?
David: Felix Dennis. Episode 129.
Sam: Yes. One of my favorite books of all time. His writing is incredible — he’s like if Mick Jagger and Richard Branson had a baby. It’s one of the very few books that’s both tactical and written by a billionaire.
He was dying of cancer when he wrote it — I think he died around 60. And he said: if I could live life all over again, I would accumulate $50 million as fast as I can, hopefully by 35, and then spend the rest of my life writing poetry.
David: And I believe him. Because he spent the last 10 years of his life retired, writing books and poetry. His philanthropic thing was planting forests — he loved trees, which is very strange. He also said he spent $100 million on prostitutes and cocaine over a decade.
Sam: I didn’t know it was crack. When he died, his girlfriend was living with him.
David: These are nightclub types in the ’80s. Some people want that life. There’s a great line in Bruce Springsteen’s autobiography: “Some people’s five years is worth more than other people’s fifty.” Some people have to burn bright. That is their destiny.
I want a very interesting life and I want to succeed decade after decade after decade.
From 1,500 Downloads to Building the Podcast Business [01:07:00]
Sam: Were you making any money in the first five years?
David: So this is a long story. Podcast advertising wasn’t like it is now. At that time there were companies that would sell ads for you. I reached out to one and they said, “We’d love to sell ads for you. You need 50,000 downloads per episode.”
Sam: How many did you have?
David: Maybe 1,500. That number — 50,000 — seemed like something I could never reach. I couldn’t compute it. So then you try things like affiliate deals. Remember, Audible scaled on podcasts. People don’t understand the size of businesses you can build on the back of podcasting.
Sam: Like my business — I made a lot of money via podcasting because I promoted Hampton on there.
David: There are a million examples people don’t even know.
Sam: The hard part is that podcasts are the most challenging medium to grow, but also the most sticky.
David: Oprah understood the intensity of a real parasocial relationship back in the ’80s, way before any of us.
Sam: She had built-in distribution through the network when there were only 60 channels.
David: I did an episode on her — might be episode 332. Her key insight was: she’d have Brad Pitt on her show, and she noticed something different about how her audience responded versus how they responded to celebrities. With Brad, it’s “Oh my god, I love your movies.” With Oprah, it’s “Oprah, come over for lunch.”
Sam: When people walk up to me on the street, they just get right into it. They think they know you.
David: And in many cases, they do. They know what I’m into, what I’m intensely interested in.
To close the Oprah thing: I think people vastly underestimate the importance of frequency. She’s in your house one hour a day, five days a week. The intensity of the parasocial relationship would be much more diminished if she were doing it once a week. That’s very important.
Second thing she realized: at the time, the most profitable show on TV was local news — it cost almost nothing to make and you could sell very targeted advertising. If Oprah comes in as the lead-in right before the five o’clock news, she bumps up their Nielsen ratings significantly. For every one Nielsen point, local news might make another $5 million a year. So if you have to pay Oprah a portion of that — you’re going to say yes.
David: I couldn’t figure out how to sell enough ads. I’ll close this real quick. I found this socialist podcast called Chapo Trap House that did not run ads — they were not capitalists and thought it was immoral. They were using Patreon, and the Patreon API is public. There’s a website called Graphtreon. They were at the top of the list with about 20,000 people paying at least $5 a month. And I thought: oh, there’s a business model right there. Their model was simple — listen to every other episode free; if you want the others, pay $5 a month.
I was like: well, business people would obviously pay for business content. So I did it. But I sold it too cheap — $100 a year or $10 a month. I ground up to a couple thousand subscribers. So you’re making hundreds of thousands of dollars, but…
Sam: A few hundred grand a year isn’t dentist money.
David: It’s not bad. But then Rob — my business partner — said, “You idiot. Your biggest asset is your back catalog, and you have a giant ‘do not enter’ sign in front of it.” He’d been trying to send episodes to people and they’re so good he was buying gift subscriptions. “I spent $900 this week sending your episode to nine friends. I have to pay $100 every time I want to share something.”
And my friend Sam Hinkie was spending $2,000 to $4,000 a year just buying it for everybody. He’s the one who told Patrick about it, which obviously changed my life from there.
And here’s another thing I didn’t understand about podcasting. This is a lesson from Rockefeller — he realized one of his advantages was that the posted rates for shipping a barrel of oil over the railroad were a lie.
Sam: He gets rebates.
David: Yes. The foundation of his empire. And what I realized: Hinkie calls me one day. “Where are you?” “I’m in the Hamptons.” “What are you doing there?” “This guy DM’d me, we talked on the phone, I really liked him. He has this giant house and asked me to come speak to his company offsite.”
Sam says, “He’s paying you for that?” “Yes.” “How much?” I told him. Then he saw what the guy was paying for the hotel — $3,000 a night.
And Sam says: “You have got to stop selling things for $100 a year. You have one of the most price-insensitive audiences in the world. They would have paid $10,000 — it’s relative to their wealth.”
And then — you mentioned the Brad Jacobs book upstairs. He sent me an early copy and didn’t tell me I was in it. I’m reading along and on about page 76, he writes: most of the investors in his new company are repeat investors, but two of his top 20 shareholders didn’t know who he was before they discovered him through a Founders Podcast episode. And I know both those people — they both told me and told Brad. That means Brad raised $750 million from my audience, from people who had never heard of him before I did the episode. That was Sam’s point: you have one of the most price-insensitive audiences in the world.
Ben Wilson, Newspapers.com, and Primary Sources [01:17:00]
Sam: Dude, this is exactly — I told Ben Wilson years ago, I found his podcast How to Take Over the World, and I said: what’s going to happen in the future is you’re going to become a kind of guru because you’ve consumed all this historical knowledge, and billionaires are going to pay you to help them predict the future by not repeating the past. That could be the business model. And the joy of reading history is that it’s education wrapped in entertainment.
Do you ever use Newspapers.com?
David: I bought a subscription. I don’t think I’ve ever gone off it.
Sam: Dude, you have to use it. It’s so fun because the problem with biographies and listening to your podcast is that you’re telling me these stories when I already know the ending. It’s much better to go back. You can find Dan Gilbert’s very first newspaper profile from the ’80s. What were people saying about him right then? Could they spot it? Were they disrespecting him? There’s so much revisionist history.
I moved to San Francisco when I was 21. There are people who are ballers now and I’m like — I knew that guy when we were nothing. I did not see it. I did not know he had that in him. And this other person I thought was going to be the one — they were nothing. So it becomes hard to predict who’s going to be great.
David: This is why I say the only filter I trust is time. That’s why I gravitate toward people who were successful over many decades.
Board of Directors: Living Edition [01:21:00]
Sam: We didn’t finish the living board of directors.
David: I think it’s a good segue. It would probably be a lot of the people I’ve had on the new David Senra show. But the first spot — first spot would go to Daniel Ek for sure.
Sam: He was cool because he’s that successful but had a soft side that I liked.
David: He is like the Swedish Buddha. I don’t know how to describe him. He is unbelievably philosophical and he’s changed my life in so many different ways.
Sam: I can’t believe he’s that way at such a young age.
David: He is so much wiser than I am. And I’ve spent a bunch of time with him. He’s another guy who will call you on your stuff — in a very polite way.
Sam: Yeah, very politely.
David: The reason I started doing video, the reason I’m doing the new show — that’s because of him. We were having this crazy four-hour dinner in New York. He says: “Why aren’t you doing video?” And I was like, “I’m not doing this for fame. I’m a very private person. I don’t ever want to be recognized in public.” And he says, “A lot more people know what I look like than what you look like. I got recognized in the gym this morning. You know what they do? They come over and say, ‘Hey, I love Spotify. Thanks for building it.’ And then they go about their way.”
He said something like: “You’re easy to understand, so you’re easy to help. Because all you care about is podcasting, it’s very easy for me to help you.”
Sam: That’s a wise line.
David: If I only had one board member, it’s probably him.
At the beginning of the first episode of the David Senra show, he told the story about how he advised Dara Khosrowshahi to take the job at Uber. He tells this amazing story — “Dara, you should take this job. You seem like you’ve been complacent.” He convinced him basically to take the shot. And later he tells Dara: “I was the one who nominated you.” He never even told him.
Shaan: This is the important part — for someone to say “you seem complacent” to you, that looks like criticism, like an attack. This is why you have to get past: don’t listen to random people, but if that person genuinely cares about you, you have to be able to receive it. He essentially told me — I’m paraphrasing — you’re lying to yourself. Get off the fence.
The fact is: podcasts with video grow a lot faster than podcasts without. He gives interviews all the time and when people ask him his favorite podcast, he says Founders. He genuinely believes it’s good for the world. So me not doing video means less people see it. Less impact.
David: A horse dealer fighting the fact that Ford’s around now. What are you doing? Get off the fence.
Then Patrick was at that dinner too. We get in the car after and we’re like — we’re going to do video.
Shaan: Patrick didn’t want to do it either.
David: Neither of us did. But you have to be smart enough to change your behavior when you’re reacting to new information.
The Push to Start the David Senra Show [01:27:30]
David: This also leads to my obsession now. Founders will always be my obsession because I’m never going to stop reading. But I’m spending most of my time now on the David Senra show.
We get back to Patrick’s house after that dinner. He’s been pushing me for years to record more conversations. And I was like, “No, no, no.” We get in the car with the driver and he says, “You absolutely have to start recording these conversations you’re having.” He says, “I just spoke 2% of the time. Daniel spoke 49%. You spoke the other 49%. I’ve known Daniel for four years. You got more out of him in four hours than I have in four years. Nobody can speak to the soul of a founder like you can in the world. You have to start recording these conversations.”
And I thought: okay, conversations — that’s different. I can’t interview anybody. But maybe I can have conversations. There could be a differentiation there.
Earned Secrets and the Future of Monetization [01:30:00]
Sam: Are you ever going to monetize this in a different way than ads and subscriptions?
David: No, I don’t think I’ll ever do subscriptions again. I think the power of media is that it’s free and readily accessible, and therefore it can compound through word of mouth.
Sam: I have some other thoughts on that I’ll keep to myself. I think you have an earned secret there.
David: One of my favorite tweets — you mentioned how I take interesting ideas out of books — I read Cable Cowboy, which is a biography of John Malone. Everyone’s takeaway is: he invented the word EBITDA, he’s focused on cash flow. That’s not my main takeaway.
In the cable industry you had about eight major players. And what was fascinating was that Malone — one of the eight, essentially a competitor of the others — was the one all the other players came to learn about their own industry from. They were all essentially building the foundation of what’s now grown into this massive industry over 50-60 years.
This tweet said: “One of the most interesting ways to have a great career is to find an earned secret and exploit the hell out of it for decades.” It was talking about Mark Leonard at Constellation Software — saying, “These vertical market software businesses are shitty for VC, but if you put them in a conglomerate, they’re great.” He started with maybe $50-80 million and built it to over $80 billion. He had that earned secret and exploited it for three decades.
Because I’ve strived to collect more information about podcasting than almost anyone else, I think I have earned secrets. I don’t think there is any limit to the size or performance of the business.
Sam: And all the great ones — like Oprah — the breakthroughs don’t have a blueprint. We were also talking about how the people who are number one in certain things are literally a hundred times better than number two. I buy into that.
David: Jay-Z has a line: “If I’m going to make it to Billy, I can’t take the same path.”
I hate advertising in most cases. I ran an advertising business. When you rely solely on advertising, it’s a pain in the ass that only captures a fraction of the value you create. But if you can make money in ways where I own bits of companies I love to promote, or do it in some interesting way, then it becomes good.
I’ll be very eager to see how you change that.
Optimizing for Impact, Not Happiness [01:34:00]
David: I’m very comfortable putting out a lot more value into the world than I capture. And I think I’m going to capture more than people expect. Somebody asked me at lunch yesterday: “What would the 25-year-old version of you think of this?” And I was like: I don’t even know if I can think in those terms. It’s already wildly exceeded anything I imagined. I’m very happy with where I’m at and what I’m doing.
Sam: Are you a happy person? I would describe you as a happy person.
David: No. Happy with the way my work has gone.
Sam: Are you a happy person? I don’t think you’re happy.
David: This is why Daniel Ek is number one on my board. One thing he’s taught me: you get around these people and you realize you don’t have any ceilings.
Sam: Those people are really rare. I’ve been around a handful of them. It is contagious. I’m always curious: who gave you that?
David: This is the key. This is constant refinement of association. People hear that and think: great advice. They don’t actually do it. So few people will do it. I’m very interested in being one of those very few. I think about this a lot. I take it very seriously.
So — do I think I’m happy? Another idea from Daniel, which is on the first episode of the David Senra show — people should listen to it if they haven’t, and if they have, watch it again. I’m going to do a Founders episode based on the transcript of that conversation because there are so many good ideas in it. We print it out and it’s like 60-70 pages. It’s like a miniature book.
His whole thing: don’t optimize for happiness — optimize for impact. That’s exactly the advice he gave Dara for Uber, and the advice he takes for himself.
If I put out a lot of value into the world and only capture 1% of it — there are other things. You can go to my website right now and send me a message. Most of them are positive — people are like, “You changed my life.” And it’s not me changing their life. They changed their own life. But they say: I want you to know this has had an impact.
This guy chased me down at the airport and said, “You don’t understand the difference of my life pre and post discovering your work.” I can’t take that to the bank, but there’s a very real, tangible benefit there.
And then — the James Dyson episode we just did. God bless Rob Moore — it took 45 emails back and forth to get it scheduled. But everybody knew: he was my number one. His first book is episode 25.
Sam: I bought a Dyson because of you.
David: There you go. Episodes 25, 200, 300, 400 — it’s all about that same book. The book that changed my life. The book that encouraged me to persevere when I had no reason to persevere. There was nothing telling me this was going to be a success. Just relentless belief that I’m going to figure this out. If I focus on it and I want it to happen, I will make it happen. I feel like I have a very intense will to make what I want to happen in life actually happen.
The crazy thing is I’ve been talking about James Dyson for seven years. Seven years in the making. And when we started doing previews and trailers for the episode, strangers I’ve never met were messaging me saying they were unbelievably happy for me.
Sam: I was invested in it.
David: So what is that? That is me capturing value. And this idea where “I have to hit a certain number or I won’t be happy” — that’s not wise. I’m not trying to be smart. I’m trying to be consistently not stupid. And if I can be consistently not stupid over a long period of time, I think that’s going to result in me being wise. And that’s what I’m after.
Sam: That was a good ending.
David: All right, that’s it. That’s the part.