Why Balance Is the Enemy of Greatness | David Senra

Sometimes I think I should shut up and not say the things I say on podcasts. David Senra.

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, somebody wrote a fucking book about it. That's an insanely high bar. It's almost like it's an obsession. It is. I'm addicted.

I've known you now for, I don't know, 4 or 5 years. I think you are crazier now than you were.

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. Like, way past that. So of course I've changed. I'm not doing this to stay the same.

Are you a happy person? I don't think you're happy.

I— I feel like I could rule the world. I know I could be what I want to. I put my all in it like no days off.

Okay, so you have to look this guy up, Elud Kipchoge. You have to see what he looks like. He looks more like a gazelle than a human being. Because the thing about, uh, world-class athletes and runners is you see them like when they're, uh, exerting themselves and like wearing their like running gear or whatever. And so they're like, yeah, he looks amazing. But then you see him in real clothes and you're like, oh my God, that person is so much skinnier, has so much less body fat than the average Joe. How on earth are these two human beings, both human beings, like a normal person versus Eliud. And so, so he, he runs the marathon, I think at like 2:01, which is like 4:36, I think for the mile, crazy fast. And what we were saying was the difference between the world's greatest or the best there ever was and pretty good, you know, it's not a little bit better. It's not 20% better. It's like 10 times better or 100 times better or 1,000 times better. And that is hard to grasp. Do you agree?

Well, were you like that or did you become like that because you've studied 400 biographies of greatness?

Well, I've known you now for, I don't know, 4 or 5 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.

Sometimes I think I should shut up and not say the things I say on podcasts because I don't like having a filter. I don't like having two different sides of me. It makes me fundamentally uncomfortable. And so then I'm like, you know what? I'm just not going to hold back. I'm just going to say this. I just did this when I went on Tim Ferriss's podcast and I talked about— Tim didn't tell me what we were going to talk about other than he told my team, he's like, please tell David not to curse so much.

That's what I told you 5 years ago.

And I don't think that came from Tim. I think that came from Tim's team. And I think we did, we accomplished that goal. But he started asking questions and I like hesitated for half a second in my mind or half a minute. I'm like, man, I should not say this stuff. I don't, this is going to be bad. And I just let it go. And since then I was just on the phone. I won't say who I was talking to, but it's a founder of a public company. He's relatively young, wildly successful. And he was just like, hey, I listened to your Tim Ferriss interview. And he's like, I know exactly what you're talking about because like I went through that too. And you hear that over and over again. So to answer your question, like, am I crazier? Is that the term that you use? Or like more intense? I think I was lying to myself for a while. And if you look at episode 222 of Founders Podcast, it says Ed Thorpe, and in parentheses it says my personal blueprint. And Ed Thorpe's a legit genius. I am not a genius. Like whatever he directed his talents to, he was going to succeed because he's a legitimate, like, I think fundamental, like genius. And what I liked about him was he was like a real balanced person. You would love him because you are like this. And I think you're truly like this. A lot of our conversations are like this where he essentially bounded his professional life. He was very successful. I'll give a quick TL;DR of his life. He was the person that invented how to count cards in blackjack. He was a mathematician and he was a— College mathematician. A professor for a long time. He wrote a book called Beat the Dealer, which tells you how to Count cards, like the 1960s, sold millions of copies. He started the first quantitative hedge fund of all time. He was like one of the first investors in Berkshire Hathaway. He meets Warren Buffett when they're both in their 30s and he gets in the car and he is like, that guy's gonna be the richest person in the world one day. Uh, so, and he invented the world's first, uh, handheld wearable computer with Claude Shannon, who's the father of information theory and another genius. It's just like, how did one guy do all this stuff?

Yeah, he's like the Forrest Gump of like finance.

All right. I read a ton. I would say almost a book a week. And the reason I read so much is because my philosophy towards reading is I want to see what worked for the winners that I love and what strategies they use. And then I want to see what mistakes did they all make? What were the common flaws that they all had? And I just want to avoid that. And so HubSpot asked me to put together a list of the books that have changed my life so far in 2025, and I did that. And so I listed out 7 books that made a meaningful difference in my life, and I explained what the differences that they had on me or what actions I took because of the book. And then also I listed out my very particular ways of reading because I'm pretty strategic about how I read and how I read so much and how I remember what I read and things like that. And so I put this together in a very simple guide. It's 7 books that had a huge impact on my life, and you can scan the QR code below if you wanna read it, or there's a link. You guys know what to do. There's a link in the description. Just go ahead and click it and you'll see the guide that I made. So it's the 7 books that had a massive change in my life this year so far, and then also how I'm able to read so much. So check it out below. So I read a lot. I read 1 to 4 books a month, mostly history. You do more or the same. How do you become sensitive enough when you read something to know that that is a point that is worth remembering? Because there's been so many times where I've read something and I will forget it, right? You, I'm reading a, like I've read a, I love the American Revolution and then like I'll reread books. I'm like, I didn't even remember about this or that. You do a really good job at recall. You've done it many times here and you do a really good job Bringing the points of the story that actually matter. And I think this is an important lesson to learn of how do you be sensitive enough to see what is important and what isn't, and then use that to change your life.

I was like a big believer in intuition and just like this, like constant refinement of your own taste. Like, I'm sure I did not have that skill in September 2016 when I started nearly to the degree that I have it now. Right before Kobe Bryant died. He was asked this question about like what he sees in like Steph Curry that makes him such a formidable competitor. And he's like, there's like a calm— this is Kobe describing Steph Curry. He's like, there's like a calmness about him. And he's like, and when you match this like calmness and belief in what his skill set is with his intense desire and work ethic to practice and to get better, like that is a very dangerous combination. And what he was referring to was Steph says, people always ask me what I think about when I'm shooting. And he goes, absolutely nothing. And so I don't overthink this. I read the book. If something, it's all intuition. It's this line is speaking to me. This is jumping out to me. I'm going to underline it and I'm going to jot down on notes exactly what came to my mind. Right now, do not overthink this. Just like, you know this stuff over and over again. 'Cause like we see Steph hitting a crazy 3-pointer in the Olympics, like to win. You know, I, I watched that clip the other day. We don't see the million other times he was alone shooting the 3. I always say the public praises people for what they practice in private. The other thing about this taste, what I realize is when I talk to a lot of other people that are really great at what they do, other entrepreneurs, people that want to be great at what they do but aren't yet. I was like, they're trying to figure out, it's like, why am I not breaking through? It's like, 'cause you're not actually interested in this. Like, 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 about like, hey, let's get this person. And like, that person's like a big name. And I'm like—

You almost don't give a shit.

And I'm like, but this is the way I think about my work. Okay, like 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. And so I cannot overcomplicate things. Munger has this line where he says something about like, the hardest thing to do is to remember why you set out doing what you're doing and to keep things simple, right? And to do that for a very long time. So the way I think about it is like, Founders is the books that I'm intensely interested in reading, right? Not just a book that I think is going to be a lot of downloads. There's been times where like, I was like, read this book. I read it, I hate that guy, and I throw the book across, literally throw the book across the room. I was like, I'm not, I don't wanna spend a week in that guy's mind. Founders is the books I'm intensely interested in wanting to read and enjoy reading. And the new show David Center is the people I'm intensely interested in having conversations with. I was on the phone with somebody yesterday and I text her and I was like, I want you to fly to Malibu and I wanna do a show with you. And she's like, are you out of your mind? Are you crazy? Because she feels, because of the guest list has been like, kind of— She's below. Yeah. And she's, I was like, and she sent me this funny meme where it's like, where like Big Bird is sitting at like a table and like everybody else is like, it's just like a normal office and you got Big Bird. And she put like Daniel Ek and Michael Dell and all these other people I've had and then her name on this. I'm like, that's not, that's not what I'm interested in. I am intensely interested in people that have singular careers. They are doing what they do in a way that is completely natural and authentic to them. And they can't, they kind of have like an inner scorecard. So like they're willing to make decisions that may not make sense to you, but make sense to them.

Have you read The Inner Game of Tennis?

No, but everybody tells me I should.

So listen to this. So I think it's a, I think the guy's name is Tim Galloway. The idea is that he wrote it in the 1960s or maybe '70s. He was a tennis instructor and so he was like trying to get his students to be better tennis players. And he developed this idea of self 1 and self 2. Self 1 is a critic. And so when you would hit a ball, you'd say, shit, that was horrible. I gotta move my hand this way. I gotta do this. Self 2 is someone who doesn't listen to the brain, but listens to the body. And you'd be like, well, I practiced this 1,000 times, just like Steph Curry. Like, I don't need to criticize myself. Instead, I'm going to be objective. And I'm going to be like, let's try moving our hand just a little bit this way. And let's just see what happens. That one, that didn't, that hit that we just did, that didn't achieve the desired outcome. What would happen if I just do this? And you just kind of feel it. And so the idea here is that you listen to your, um, Use your body more than your brain. And it's very similar to what you're saying of like being simple and being, um, following, following intuition. And in fact, this book, I think Bill Gates is the most recent person to write the foreword, uh, of the book. It's, it was launched in the '70s and they've republished it and it's now, it's like a business cult classic. And the idea here is exactly what you're describing, which is like you, you keep things very simple, you practice a lot and you don't criticize yourself and you don't like think too hard about what will do well.

The criticism, and me and you have talked about this a lot, uh, like in private, like we both were maniacally driven to fix and to achieve financial success. And a lot of times that doesn't come from a positive place.

Yeah. The way that I see it a lot of times is basically I build businesses because I feel like I have, uh, I'm not good enough. And also I try to fix myself because you have to fix your personality in order to build a great company.

So, but that's the hard part because in general people don't change. You know, Robert Greene has this great book called Human Nature and he was like, in general, assume most people won't change. Yeah. Most people.

I'm not trying to be most people.

Yeah. But you're, but we still have that in us where like you have to fight inertia and that's, and that's quite hard. Yeah.

So we we were talking upstairs, this Bruce, 'cause you're a Bruce Springsteen fan and his autobiography, I would highly recommend people go watch this movie called Deliver Me from Nowhere, I think it is. I thought it was going to be a biopic of Bruce Springsteen. That's not what it was. It was about a guy that had an unbelievably tumultuous childhood that funneled that pain into an unbelievable work ethic to get him what he thought he wanted most in the world, which is being a rock star. And then right after he hits that, after years and years of struggle, he plunges himself into deep depression. And what he realizes is like he can't form, he's so, his childhood was so messed up. It did not give him the ability to form stable, loving relationships with women. And what he desperately wanted was, I, he wanted a stable relationship. He wanted to have kids because he wanted to raise his kids and break the chain that his parents did to him. And yet what he would do, he would freak out. He'd like, he'd fall in love with a woman or whatever the case was. And then he'd be like, something's wrong with her. She can't— if she loves me, I am unlovable. So therefore I'm going to hurt this person. He would run away and then he'd start dating somebody else and he would go through this over and over and over again, right? Until the point where he has to go wind up seeing a therapist. He basically is like, hey, my life is going to be miserable. 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. And the crazy thing about the book, the book is 600 pages long. Half the time you're like, this guy is— the first half of the book is about his love for his work and his work ethic. And so you think you see where it's going. And then this curveball happens in his life where he's like, life is more important than work. What Bruce was figuring out is that every human wants relationships, whether it's a romantic relationship or a true friend or something, somebody understands you that you feel like you can do life together. And I now have, like, my friend group is crazy because of how high quality they are in all the domains, like all areas of their life. And that was like, oh my God, it's not that I was like, didn't like, that I didn't want to let people in or I didn't like, other humans. It's like, I didn't have access to this before. And so like almost every single one of my new friends have come from the podcast. And in some cases, they've become like best friends, people that I've spent years getting to know and like spend hours and hours talking to. And so that's where it's like, oh, like, this is actually really important to me. Relationships are really important to me in a way that I didn't understand. And maybe I was like lying to myself about this. And so So that was like a huge learning for me. And then the reason I bring this up for the Bruce Feasting thing is because he's messing up at something he deeply desires, yet he's smart enough to realize, hey, what are the tools that I need to fix this? Because if I don't fix this, I'm going to have another 30 years, or in his case, 40 years of my life where I'm going to be miserable. So it's like changed his behavior. That means he learned. You're not learning if you didn't change your behavior.

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You know what's crazy? I think when I— every time I listen to your podcast, I have envy of the people, not because of their success, but because like particularly like Bruce, but there's a lot of people who found their passion very early on in life. And I don't know if that's luck, what it is, but I think that that's like the, whenever I listen to Founders and I, and now the David Sutter Show, I think like, how crazy is it? Like we were talking about music. I, I, whenever I go to concerts and like, if it's a band that I've loved for years, I loved Green Day for years. Billy Joe will play a song that he wrote when he was 15. And I'm like, how fortunate are you that you were able to create stuff at the age of 15 that's still relevant to you in your 50s or 60s? And so I get like, like one of the, my favorite, one of my favorite ones you've done. I didn't like this guy, but what's the Liz Zottica guy's name? Oh yeah. Dov'ecchio. So basically for the listener, this guy like started like a sunglass conglomerate. That's a monopoly and it's an $80 or $100 billion company and he tried to pass it on to his sons and try to make it a family dynasty. But there's a ton of like bad shit that he's done in his life with family and, and he seems like a pretty like angry, generally angry guy. He was like an orphan. Yeah. Like this is what I mean.

He had a lot of darkness, but he never dealt with it. Where I just give you an example. Bruce is like, no, I'm not going to—

well, he dealt with it at the end. I think at the end of the episode, you're like, he was like, the thing that I wish I did differently was how I treated my children.

Yeah. But on the episode I said, I don't believe him. Right.

And that's what you said. But what I do envy of him and many of the people is that they found their passion early.

I, I could see that, but like I was 32. When I found like what I wanted to do. Really? Yes. Bruce Lee was 15. Kobe Bryant was like 11. Leonardo, I think it's Leonardo da Vinci, was what, 17?

Yes, he was young. 32 is young. But the fact that you find it in the first place.

Ruin their success.

They are successful, they're talented, and they destroy themselves. Yeah. What are the 4? The first one was drugs, pills, heroin, all this stuff. I don't do any drugs. That's not going to happen to me.

Did you see the Eddie Murphy documentary?

No, everybody keeps telling me about it.

Oh, it was so good, dude. And one of the main things was, you know, he was famous since he was 16. He was on SNL, I think, when he was 18. And, you know, did all these movies when he was 21. He was like, I've never done drugs. And he's like, that's one of the main reasons why I am what I am.

So his, he's going to be number 3 on this list, which we'll get to in a minute about what could destroy you. And he wasn't destroyed by it, but he has a, he's addicted to something else, which we'll get to. Number 2, alcohol. Like, you just like can destroy your life. You know, I had— I went to dinner last night with a friend and like I had a glass of sake, like, but I didn't get drunk. It was like fine, right? 3, women. They just like, they attract the wrong kind of women. They fall in love with the wrong kind of women. They let the wrong women in around them. Like, they're like—

What's the Patriots coach? Bill Belichick? Yes. You see what he's doing now?

He's dating like a 20-year-old or something?

Oh yeah, man. She just calls the shots. Okay, that— well, it's exactly what you're describing. No, in case it gets a lot darker.

There's like, just, it can distract you. It's just, you have to, you want high-quality people around you in every single domain. Friends, high-quality people. People you work with, high-quality people. The people you date, you want high-quality people. Like, you just want high-quality people. It's like, it's the most important decision you make in your life is the people that you let around you. Which I see people are way too casual about this. And I could be really, really ruthless in this domain. And then the fourth one is megalomania. And the reason I say Eddie Murphy, because he's dated every single person. He's got like 10 kids. I think he's got a bunch of different baby mamas. Again, he's still living his life he wants to do, but he clearly likes that number 3. So number 4 is just megalomania. You start to think that you're successful because of you and not the work that you put in. And you start to believe you have, like, you're like a god and like everybody should, you know, praise you and you just completely become disassociated from reality. And this is why I say like, it's very dangerous, especially to like do numbers-driven thing. Like I talk to founders all the time. I'm like, oh, like tell me about your company. Like, I just want to be the first, you know, I want to build a trillion-dollar company. I want to be the first, the fastest company to $100 million ARR. I'm like, you know, like none of history's greatest entrepreneurs thought like that.

I'm calling you out on that. That's bullshit. Because when I talk to Ramp, The Ramp founders are amazing. They're like the best of the best. They said our goal is to get to $1 billion in valuation in 18 months. That was not their primary goal.

Their primary goal—

But they said that's what their goal— I mean, he was like, I think it'd be cool if we could do that.

Oh, that's different. That's— Oh, come on. No, that is different. 100%. I'm saying the reason for your existence, the reason what you're doing, these people are telling me I'm only starting this company so I can hit a certain financial number.

That's completely different. No, that's not what he said.

Yeah. Yeah. That's not what they— I was— wasn't I there with you in the office? I recorded with him and he repeats he says this all the time.

It's like, that's like a cool thing. He was like, I thought it'd be cool if we get to a billion in valuation in 18 months.

I don't know if I heard that episode, but like there's—

He said it a bunch.

Okay. Their experience with, uh, Paribus beforehand was giving the insight into the founding story of Ramp. So that's a longer story. But my point being is like, I'm hugely skeptical if you're— there's some kind of external metric that I will only be happy if I hit that metric, or that is the reason that I'm doing this. Where mine is just like, I want to make things that I'm proud of, that I think are good and like I could put out and they're like good into the world. And I don't confuse, like when we were just upstairs and you're like that guy sitting next to us. It's like, I don't confuse with somebody saying, hey, I like what you do. Like, that's the perfect way to say it. You like what I do. You might like me as a person. If we knew each other, we'd probably get along. We probably have the same interests, but never confuse that they don't like you. It's the work. And if once you stop putting in the work, everything else goes away. That is how the megalomaniacs, they just think like, I'm so talented, I just show up, I just, everything I touch turns to gold. I don't have to practice, I don't have to put any effort and everything's going to work out. And then they also, you know, treat people essentially not as people.

If you had to teach someone who is 19 how to find their life's work based off of talking to, reading about 400 people and now talking to dozens of hundreds of successful entrepreneurs, what would you say is the exercises that they should do?

My problem is I think at that age I wouldn't have taken anybody's advice. And I think I'm only now the last few years, like, been open to letting other people, like, mold my mind. Well, what would you say? The fact that they're asking the question, like, there's this great line where it's like a 21-year-old kid comes up to Mozart and it's like, I want to know how to write a symphony. And he says, you're too young. And the guy that is asking Mozart the question is just like, yeah, but you wrote symphonies when you were 14. He's like, yeah, but I didn't go around asking people how to do it. There's something in there where you feel somebody else has the answer. That doesn't mean you shouldn't ask for advice. Be very clear here. I don't think there's anything magical I would have to say that would put them on the other 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 and over again. And this long conversation last night and the conversation started, it was like, what's the lie that you're telling yourself? And we went back and forth, me and this other person for a while about this. My lie, I'll just tell you right now, which again, I'm probably sharing too much publicly, is this is like that I don't need anybody else. That's a lie. You think that. That's a lie I've been telling myself for a very long time, which again has happened And I learned that because of the experience I'm having, the relationships I have, like realizing that like you're doing that because it's a defense mechanism, not because it's actually true. And so for this, I would be like, take the time, like what do you actually want? And that's very hard to be truthful about. And the one way that I found it is just like, I just follow, like I have ungovernable curiosity about things. I cannot tell you why I like to read. And so like when I first started my first podcast, I was just like, oh, like It'd be cool if I could build a business and a life where I just get to read all the time, which sounds ridiculous, but it actually worked. And then you just follow this. And then now to the point where we recorded this conversation with Todd Graves, who's one of the people I wanted to meet the most, which people sounds crazy, but I'm like, he's like, what does he do? He's like, he sells chicken fingers. And they're like, what? Why do you want to meet him? I was like, because he grinded himself. First of all, he's been doing his business for 30 years, started out, built the first store by hand. He had no money, went to crazy risk to find the financing 'cause there was no venture capital. No one would give him money. He had to risk his life on a boat sailing off, fishing off Alaska. He worked as a boilermaker. He was highly leveraged and almost went out of business. He did all these crazy things 'cause he just found he had this chicken finger dream. That's what he calls it. And he's like, I have to do the chicken finger dream. I can't explain why. Again, he's not looking for external validation. I'm going to do this. Everybody's like, you're an idiot, you can't do that. Hasn't changed his menu in 30 years. So we fly to Baton Rouge. The conversation is incredible. We record for 2 hours, 2 and a half hours, 2 hours. And then we spend another 2 and a half hours one on one together after.

Was he any different? No, because these people—

and he also listens to the podcast, so he understands who I am. Like, it's just very— this is what I meant. I was like, I don't make media. I'm building relationships.

He might be a top 10 person I've listened to on your pod. Yeah, he's incredible.

And so This is the point about following the curiosity, going back to the 19-year-old. I go back to the airport and I call Sam Hinckley and he picks up and I go, I'm in big trouble. And he goes, what's going on? I go, I am already wildly addicted to having these conversations. He goes, I go, I've never done ecstasy, but this is how I feel right now. I am like high. I am wired. I am like high as a kite because I had this guy Again, he's got 3 decades of experience. He had 915 stores. The company's worth over $20 billion. He owns 90% of it. He's growing faster in year 30 than it ever has in his history. He still has trouble sleeping 'cause he can't wait to wake up and get back to work the next day. And so you just get like, you get this download of information and energy from him that like just made me euphoric.

Who would be on your board of advisors? Would he be on one of them?

How many people do I get? 6. I have to name them? Yeah. Living or dead? Either. Let me do dead just because that'll give me some time to think about living. And I think like, I don't know if I want to answer that question honestly, but I would have to. Dead, you know, Rockefeller built the greatest company ever created.

I would say Rockefeller, I think is one of the few tycoons of, in terms of like impeachable character and like amazing success. I think he's the best. Debatable and impeachable character. No. Okay. Impeachable's not the right word because he screwed up. He did lie on the record a bunch of times, but In general, I think he was a, he's an ethical, honest person.

Got a little handsy towards the end of his life. Let's just put it that way. I remember I collect obscure—

he was 100. I collect obscure Rockefeller biographies.

I have made my own. There's, I have one at my house I haven't done an episode on. It's 1,700 pages long. It's in a big binder.

He was a weirdo when he was like 90 and he was like giving people nickels and shit.

That's, yep, that's fine. Great bus— he undeniable, one of the best businesses ever created. Charlie Munger told me to my face. That he thinks Rockefeller created the best business in history. Yeah. Okay. Munger would have to be on it 'cause he's dead unfortunately now. I think he's the wisest person I've ever studied. If I could only emulate, learn from one person, it'd be him. Edwin Land, founder of Polaroid. Who's that? Founder of Polaroid, patron saint of Founders Podcast. He was Steve Jobs' hero. His whole thing, he's got a lot of things that, a lot of personal mottos. He invented the instant photography, the entire industry. Then monopolized the industry. It's like one of the last great American technology companies that were never like, his patents were never—

What did he die? I've never heard of him.

In the '90s. He met, when he was in his '70s, Steve Jobs met Edwin Land when he, Steve was like 25, Edwin Land was like 72, I think. And he said, Steve Jobs said that spending time with him was like visiting a shrine. This is how a lot, I get to meet like crazy people in the world, right? I actually had lunch with a friend yesterday and she told me something fascinating. She just was like, you need to take a minute to think about what's going on in your life and the fact that you have this ridiculously sick life because of the people you have access to.

You ever write this stuff down, like a journal? No.

I was up in your room and I took a photo of your book. You had the Brad Jacobs book. Yeah. And I was like, I just want to see what he's underlining. I was like, I just want to see like his thinking. You underlined so much stuff. You had so many notes in there. Yeah.

All right, let's take a quick break because I got to tell you a story. Let me tell you about the first time I tried to run payroll for my team. I was using a traditional bank and you know the type, it's got a janky interface. It's built like a 2002 tax form and it was open only during business hours. And I hit send and it froze. They flagged the transaction, they locked my account, they put me on hold for 45 minutes, and then they told me I gotta visit my local branch. And that was the day I started looking for a new banking solution. Uh, after asking a few founders what they were using, I found out about Mercury. And so now my payroll is 2 clicks. I can wire money, I can pay invoices, I can reimburse the team all from one clean dashboard. That's why I use it for all of my companies, and so do 200,000 other startup founders. And so if you're looking to level up your banking, head to mercury.com and apply in minutes. Mercury is a financial technology company, not a bank. Banking services are provided through Choice Financial Group, Columbine, and Evolve Bank and Trust, members FDIC.

What do you think would be the biggest regret of the, of all the people that you've talked to? What would be the top 3 biggest regrets that they've had?

I, I, this is where it's like with these kind of people, I don't, necessarily believe them, that they're regrets. So Sam Walton, he's writing his autobiography as he knows he's dying. He's got cancer all over his body. He's in immense pain. He took out some of the last time that he ever had in life, and he essentially distilled what he learned from his 50, 60-year career. And I think it's one of the best books, easily top 5 entrepreneur book of all time. And it's such a gift to future generations of entrepreneurs that he did that with his last time. And he said that he missed out a lot of stuff. Like, he was working all the time. He's like a fairly, he calls himself a fairly overactive fellow. Yeah, well, that's one way to put it, Sam, but like that you're just a conqueror, you're an insane person in a good way. He's trying to do something that he thought was good. And he's like, if I had to be honest though, like, yeah, I missed out on seeing parts of my kids' lives. Like I was working a lot, but he's like, if I did it all again, I would do it the exact same way. And I think a lot of people feel that way. And they get to the end of their life and then they're like, I think it's just natural to be nostalgic and to think, oh, what I would change. But even Buffett says in Snowball, whatever he did to draw, to push his wife away, his first wife, I would go back. He says, I would go back and do it differently. Maybe, I don't know. I think he did exactly what he wanted to do. Maybe in that case he's, he's right. He's like, I was like truly in love with this woman and I messed that up. I could see that being like a true regret. I think a lot of these people have a hard time assessing like their own regrets accurately.

There's this great book called How to Get Rich. Have you read that one?

Felix Dennis, episode 129. Yes.

Cocaine, cocaine over a decade.

I was going to bring that up where like, this is, this is, he was a crackhead. He was a legit crackhead.

No, it was crack.

He was like a crackhead. Right around here, actually, in this neighborhood.

I believe him because he got to like $500 to $800 million. Like he got way—

yeah, but this was like in the year 2002. So like even more.

Yeah. And so you read that book and again, this is why like I spent so much time with these older people because there's like a certain, like you don't know yourself as well when you're younger, you're still on the rise. And so you're incentivized to like put on a show. Essentially, like you're not being truthful. And you can't let the world actually see how you, like, what you believe about certain things. And especially in like this entrepreneurial ecosystem you're in, like most of these startup founders are just straight up lying so they can raise more money. Like it's really gross and disgusting. This is my whole thing. I am fundamentally, if I am like being, if I'm being dishonest about something or if I have like different sides of me, I don't like that. I need to reconcile that right away.

I get so much more value out of listening from old people than I have reading Twitter or whatever. It might be because they're willing to tell you the truth. Well, and it's also because once you get past a certain level, and that level honestly is pretty small, but like once you get past a certain level, the analogy that I heard recently was really good. It was like, I'm no, I'm, I'm, I'm the captain of a boat and I'm not trying to fix the engine, but steer the ship. And so I don't want, I don't necessarily need tactics right now. I just need, tell me how to live like a good life and a good life is a variety of things, but like I need to know about what the definition of a life worth living is, not how to make money or whatever. I don't know, whatever the tactics are. And so I've gotten so much more value. So my friend Noah Kagan's got this channel on YouTube where he interviews like 80-year-olds and, uh, mostly like entrepreneurs. I've gotten so much more value out of that.

You see this, if you can't interview them, you at least, you can pick up like Felix Dennis's book where how many people are going to be honest about that is a crazy thing to admit to that I spent $10 million a year. For 10 years, $100 million on prostitutes and coke.

Dude, when he died, his prostitute girlfriend was living with him.

Again, I'm sure I can't imagine the STDs this guy has or had and doing coke and drinking in nightclubs because these are like nightclubs, I think, if I remember correctly.

Yeah, like in the '80s.

Dude, it's just like, you don't want to do that. What are you doing? It's going to shorten your life. And some people want to. There's a great line in Bruce Lee's autobiography where he's like, some people's 5 years is worth more than other people's 50. So some people just have to burn bright and they're going to, that is their destiny. That's what they're going to do. I want to have a very interesting life and I want to succeed decade after decade after decade.

Were you making any money in the first 5 years?

Back then, so this is a long story, but the podcast advertising is not like how it is now, which is way more advanced and you can sell your own deals independently. So at that time there was, like these, they call them podcast networks, but they're not even, I guess they're not, there wasn't a network of podcasts. They would just sell ads for you. And so I just remember reaching out to one of them and they're like, we would love to, to like sell ads for you. It's like, you need 50,000 downloads per episode.

How many did you have? 1,500?

The number they said, I was like, 50,000? I was like, it seemed like such a, it's like, I will never have that. Like I just didn't, I couldn't compute to it. I don't even know what I had, a couple thousand or whatever the number was back then. Um, and so then you would like try to do like, you could do like affiliate deals. Like remember Audible scaled on podcasts. People don't understand the size of businesses you can build on the back of podcasts to this day. And now I don't even talk about this publicly anymore. Cause like, I think this is a secret of mine.

Like my business has made a lot of money via podcasting because I promoted my company Hampton on there.

And there's just a million examples that people don't even know.

Like I've collected all these case studies. The hard part is that it like podcasts are like the most challenging to grow. But they're the most sticky, I think, of all the mediums.

Oprah understood the intensity of a legitimate parasocial relationship back in the '80s, way before, like nothing we're doing is new.

She had built-in distribution, right? She hooked up with the network and that was, and there was only 60 channels. I did an episode on that.

That might be 332. I might be wrong on that episode. But the key there, and like, let me just tell you her insight and I'll tell you what she figured out, how to monetize it in such a huge way. Her key insight was, you know, she would have like Brad Pitt on her show or like these A-list celebrities. And she's like, Oh, I have something different because the way my audience responds to a movie star is not the way they respond to me. And so they're like, Brad, oh my God, you're handsome. I love your movie.

They're like, Oprah, it's nice to see you. No, they're like, Oprah, come over for lunch.

Yeah, more targeted. Huge target, you know?

And what she realized is like, if you have Oprah coming into being the lead-in from 4 to 5 to your 5 o'clock news, right? She's gonna bump up your rating, your Nielsen rating by like, I forgot what the number is. Let's say 3. And for every one Nielsen reading, your local news would make like another $5 million a year. So let's say you don't have Oprah, you just lost out on $15 million. So if Oprah says, oh, I'll sign with you, you have to pay me 5 of that. I'm making up the numbers. You have to pay me 5 of that 15. You're going to say yeah. So what I couldn't figure out how to sell enough ads. I'll close this real quick because I've talked about this on other podcasts too. I had found this socialist podcast called Chapo Trap House that was selling, that did not run ads because they were not capitalists. Right. So they thought it was, you know, immoral. And they were using Patreon at the time to sell subscriptions to podcasts. And the Patreon API is public. And there's a website called Graphtrion. And they were at the top of the list. And I found this and they had 25,000 people or 20, let's call it 20,000 people paying them at least $5 a month. And I'm like, oh, there's a business model right there. And their business model was simple. You can listen to every other episode for free if you want. The other episodes you're not getting, you have to pay $5 a month. And so I was like, well, this is like information for business. People for business would of course pay for this. And there's actually a story here. And so, but I sold it too cheap. It was like $100 a year or $10 a month. And then I ground to like a, grinded to like a couple thousand. So it's like you're making like dentist money or something like that is the way I would think about it.

But then— That ain't $24 grand a year ain't dentist money.

No, you're making hundreds of thousands a year.

I thought you said $2,000 a month. You got it. No, no.

Annual subscribers had like a couple thousand, like 3,000, 4,000, something like that. So that'd be like $400 grand or whatever the number is, right? But then let me, then I also, Rob was like, you idiot, I'm trying to send this. He's like, your biggest asset you have is your back catalog and you have a big giant do not enter sign in front of your biggest asset. He's like, I've been trying to send it to people and it's so good that you had to buy gift subscriptions. And so he's like, I spent like $900 this week sending your episode to my 9 friends. I have to pay $100 every time I wanna send somebody's, uh, to a friend. My friend Sam Hinkley, who he was spending like $2,000 to $3,000 or $4,000 a year. 'Cause he's like, this is too good. He was just buying it for everybody. He's the one that told Patrick about it, which has obviously changed my life from there. Um, and so then here's another thing which I didn't understand, that podcasts are not all, all is not that it appears from the outside. This is a lesson from Rockefeller. Where he realizes that one of his advantages was that not everybody— there's posted rates on how much it's going to cost to ship a barrel of oil over the railroad.

That posted rate is a lie. Yeah. So he gets rebates. Yes.

Dude, this is exact— I told Ben Wilson, I, so I found, I've been the history buff for 20 years and I love Ben and I saw Ben's podcast, How to Take Over the World. And I was, he sent me the graph. I think when I found him, he was doing 100 downloads an episode. And I was like, Ben, what's going to happen in the future is you're going to become sort of like a guru, but not in that type of way where because you've consumed all the— this was before AI— because you've consumed all this history knowledge, billionaires are going to pay you money to help them predict the future by not repeating the past. I was like, that could be like the business model. And it was like hard to understand at the time, but it's telling your time kind of sucks, but that's like the joy of reading history. It's basically, it's like sort of education that's wrapped in entertainment. That's why I love it so much. Do you ever use newspapers.com? I bought a subscription.

I don't think I've ever gone on.

Dude, you have to use it. It's so fun because the problem with biographies and like listening to your podcast is you're telling me these stories when I already know the ending and it's so much better to go back. So for example, you could read about like Dan Gilbert and he's just like one of the greats when it comes to being an entrepreneur. And you can read about him and watch interviews, but you know that he was successful. You already know the outcome of the story. And so it's really fun to go back. I use newspapers.com. Newspapers like I'm all the time because I go and find articles in the '80s when they, when, and I'll find his first profile, like the very first time a newspaper wrote about him. I'm like, what were they saying about him right then and there? Or how are they disrespecting them? Or did they like, could they spot it? Or like, because there's revisionist history, like what were people saying about him then and there? Because, because I was in San Francisco starting at, I moved to San Francisco when I was 21 and there's a bunch of like people that are ballers now. And I'm like, I knew that guy when we were nothing. I did not see that. I did not know that he had that in him. Or this person I thought was going to be the shit, they were nothing. And so it kind of becomes hard to predict who's going to be— I mean, obviously angel investing would be a lot easier if this were the case.

This is why I would say the only filter I trust, time is the best filter. And so that's why I tend to gravitate towards people that were successful for many decades. We didn't finish the— so if you think you asked me the living board of directors, I think this is a good segue into what you were just talking about where it's like it would probably be a lot of the people that I've had on the new David Center Show so far. So like— Lovitz, Dell. No, the first spot would go to Daniel Ek for sure. For sure.

He was cool because he, everyone's a shark who's that successful, but he had a soft side that I liked.

He is like 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.

I can't believe he's that way at such a young age too.

And that's the weird, like we're close in age, but he is like, so much wiser than I am. And I've spent a bunch of time with him. And I would say he's taught me a lot. Like, he's another guy that will call you on your shit in a very polite way, though. Yeah, he's great. So, like, the reason I started doing video, the reason I'm doing the new show, too, is because of him. And his whole thing was just like, we were having this crazy dinner, this 4-hour dinner in New York. He's just like, why aren't you doing video? And I was like, I'm not doing this for, like, fame. I'm a very private person. I don't want to ever be recognized in public. And he's just like, a lot more people know what I look like than what you look like. He goes, 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 ways. And he's just like, you, I'm paraphrasing what he said. He's just like, he knew I was like obsessed with podcasting. He gave me great advice. He's like, you're easy to understand. So therefore you're easy to help because all you care about is podcasting.. And so it's very easy for me to help you because I, you're, you're—

that's a wise line.

He's, this is what I mean. If I only had one board of directors, it's probably him.

He, in the beginning of the podcast, he tells a story about how he advised Dara to take the job at Uber. And, and he was like, he tells this amazing story. He was like, um, Dara, you know, I think you should take this job. And Dara is saying like, you know, somebody nominated me to like, uh, run Uber. And Daniel was like, yeah, you seem like you've been complacent, this and that. Uh, and then he like, Talks about how he convinced him basically to take this job at Uber. And then he later tells the story. He's like, I was the one that nominated you. He didn't even tell him. He was like, I nominated you.

This is the important part for somebody to say that to you. You seem complacent. That looks like you're criticizing. That looks like you're attacking. This is why you have to get over, don't listen to random people, but if that person genuinely cares about you, you have to be able, this is something I struggle with. Like you're, this is, he didn't curse. He was just like, essentially my paraphrase is like, you're lying. This is bullshit. Like get over, like he said something about like getting on, like I'm straddling the fence. I can't remember the exact words, but essentially just like, this is the business you've chosen. And the fact of the matter is podcasts that have video grow a lot faster than podcasts that don't. He gives interviews multiple times. People ask him what his favorite podcast is. He says Founders. Like the, he's like, he genuinely believes it's good for the world. So me not doing video means less people see it.

Less impact. A horse dealer fighting the fact that Ford is around now.

Yeah. And it's just like, what are you doing? Like, so get off the fence. And then, then me and Patrick's at this dinner too. We get in the car after that and we're like, we're going to do video.

Well, Patrick didn't want to do it either.

I know neither of us want to do it, but that's why my point is like, you have to be smart enough to change your behavior when you're reacting to new information. And so this also leads us to really what, like my obsession now, founders will always, always be my obsession because I'm never going to stop reading. But like, like I'm spending a lot of time, most of my time will be on David Senra. Is we get in the car, I'm going back to Patrick's house to spend the night at his house. And he's been pushing me to record podcasts and do more what he called interviews at the time than he did for years. And I was like, no, no, no. Whose house do you say? Patrick. And we get in the car with the driver and he's like, you absolutely have to start recording these conversations that you're having. He goes, I just spoke. He goes, I spoke 2% of the time. Daniel spoke 49% of the time. You spoke the other 49% of the time. He goes, I've known him for 4 years. You got more out of him in 4 hours than I have in 4 years. Nobody can speak to the soul of the founder like you can in the world. You have to start recording these conversations. And that is the push. I was like, oh, that conversation's different. I can't interview anybody. That might be interesting. There could be a differentiation there.

Are you ever going to monetize this in a different way than normal media ways, ads and subscription?

No, I don't think I'll ever do subscription again because I think that— So you're only going to monetize with ads? Yeah, I think the power of media is like it's free and readily accessible and therefore it can compound through word of mouth.

It's such a shitty business model for how much influence you have. I don't—

No. And all the great ones that like, you know, we were talking about Oprah the other day, like there is the breakthroughs don't particularly have like a blueprint where you're like, and we were also talking about how like the people who are number one in certain things are literally 100 times better than number two. So I buy into that.

Jay-Z has a line, if I'm going to make it to a Billy, I can't take the same path.

And so I'll be very eager to see what you're going to do. I hate advertising in most cases. I ran an advertising business. When you rely solely on advertising, I hated it. But if you can make money in ways where I own bits of companies that I love to promote, or if you do it in some interesting way, then it becomes good. But the traditional form of advertising, I think, is a pain in the ass business model that only captures a fraction of the value that you create. And so I'll be very eager to see how you will change that.

And here's the thing, I'm very comfortable. Putting out a lot more value into the world than I capture. And I just think I'm going to capture more than like, if you go back, somebody asked me, my friend at lunch yesterday asked me, he's like, what would like 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 like already wildly like exceeded. I'm just very happy like where I'm at and like what I'm doing. And I know that I have—

Are you a happy person?

I would describe you as a happy person. No, no, happy with the way my work is going.

Are you a happy person? I don't think you're happy.

I think this is, again, why is Daniel Ek number one on my board of directors? I already mentioned one of them, like he's pushed me in a certain direction. Another thing that he's taught me is like, you get around him and you realize like you don't have any ceilings.

Dude, those people are really rare. I've been around a handful of them. It is contagious. And I'm always curious. I'm like, who gave you that? This is the key.

Dude, I bought a Dyson because of you.

Exactly. There you go. 25, 200, 300, episode 400. It's all about the 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 that I was seeing that's like, this is going to be a success other than just relentless self-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. Like, I feel like I have a very intense will to change, like, what I want to happen in life to happen. And so the crazy thing is, I've been talking with this guy for 7 years. It was 7 years in the making. That when we started doing the previews for the episodes, showing the pictures, some of the trailers, some of the clips, then the episode comes out. Strangers I've never met are like, I'm unbelievably happy for you. I cannot— I know.

Yeah, I saw that. That was cool.

Like, how crazy is that?

I was already invested into it.

That was a good ending. All right. That's it.

That's the pod. I feel like I could rule the world. I know I could be what I want to.

I put my all in it like no days off on the road.

Let's travel, never looking back.

All right, my friends, I have a new podcast for you guys to check out. It's called Content is Profit and it's hosted by Luis and Fonzie Cameo. After years of building content teams and frameworks for companies like Red Bull and Orange Theory Fitness, Luis and Fonzie are on a mission to bridge the gap between content and revenue. In each episode, you're gonna hear from top entrepreneurs and creators, and you're gonna hear 'em share their secrets and strategies to turn their content into profit. So you can check out Content is Profit wherever you get your podcasts.