David Senra: Mute the World and Build Your Own

Intro

David Senra: The best founders kind of don’t really rest on their laurels and they don’t sleep on wins. They essentially do something great, they’ll celebrate for like a day and then back to it. So like I just did Tony Xu of DoorDash, who I think you guys were investors in. He’s like, “We got so much more to do.” He’s like, “Okay, we had something good happen. Like, let’s go out to dinner. And by the time the dinner—before dinner’s over, I’m thinking of the 17 things that are not going right.” And that’s why he’s great.

Brian Halligan: Okay. Today we have David Senra on the show. I’ve been a huge fan of his pod for a long time. He basically goes way down the rabbit hole on great founders from Jesus of Nazareth all the way up to Jensen Huang. Very, very, very deep down those rabbit holes. So what I wanted to know is what do all the great founders have in common and how do we apply that to today’s founders? How do we apply that to picking the best founders and how do we apply that to coaching my best CEOs? I hope you like the episode.

Main Conversation

Brian Halligan: You have gone very deep on a lot of founders, a lot of CEOs, a lot of successful people from Jesus of Nazareth to Jensen Huang. [laughs] What’s the one thing they have in common?

David Senra: If I had to distill every single thing down to one word, it’d just be like “focus.” They’re just unbelievably focused compared to not only the average person—it’s almost like they’re a different species—but I would even say to today’s founders, they are just much more focused and less distracted and, like, not really looking around at what other people are doing. They kind of don’t really care how other people are doing what they’re doing. The way I put this is like there’s a maxim for this: mute the world and then build your own.

Brian Halligan: Yeah.

David Senra: And so let me give you an example of this. This isn’t out on my new show yet, but I just spent several hours with Dana White. I call him the founder of the UFC, even though it’s like, oh, they bought the company. And Dana, first of all, is one of my favorite conversations I ever had. We had so much fun. But when he tells the story of the UFC where it’s like, you know, he’s 19 years old, he’s a bellman in a hotel in Boston, and he’s self-described loser. He’s just like, “I’m just a loser. I have nothing going on, but I’m obsessed with fighting.”

And at that time it’s boxing. He’s a huge boxing fan. And he has this idea, he’s like, “I should just move to Vegas—fight capital of the world—and try to just work in the industry.” Now he’s trying to build the world’s biggest combat organization, but he’s just like, “I just need to work in this industry.” And he was going back and forth. He’s like, “This is stupid.” He goes, “I’m a bellman. I could be a bellman at 35. If this doesn’t work out. I could be a bellman at 35. I could be a bellman when I’m 50. So I have nothing. I have no wife, no kids.” And he just goes, starts working in the industry, taking any job he can get, starts promoting—excuse me, managing fighters—then starts managing this weird thing called MMA and these fighters for this thing called UFC, which is nothing. They’re in front of tiny crowds. There’s no money.

And so he’s on the phone because he’s a rep for two fighters, and one of the fighters is owed money by the UFC. And he’s like, “Dude, you need to pay him.” And the guy screams at him, the owner. He’s like, “There’s no fucking money! There’s no money!” So Dana hangs up, calls the Fertitta brothers, who their father built a casino. He’s like, “I think we could buy this whole thing.”

And what you realize is he’s a missionary founder. I think the best founders are missionary. Like, if you go back and look at Jensen or Steve Jobs or Bezos or any of these people—Elon—missionary. And he’s like, “I think we could buy this thing.” They buy it for $2 million. Takes him, like, six years. He’s making no money. They’re losing money. They have to dump another $40 million into it until it’s profitable. And then he tells this whole story. So I’ll get to the end because he’s still been running it for 26 years. And now they just did almost an $8 billion deal for their TV rights at a time where he’s making no money for the first six years. The first time he makes money, they write on the board the compensation for the partners, and he can’t believe it. He’s like, “Oh my God, I’m gonna make $1 million.” He thought he was rich. I can’t even tell you what he told me he makes now. He told me off camera, it’s just—it would blow your mind.

And the reason I bring this up is because I talked to him. He’s like, “I’ve never read a single book about business. I’ve never listened to a single podcast about business. All I did was like, I’m the fan. So when we bought the company—I never sold tickets, didn’t know anything about production.” He’s just like, “I just made what I wanted to see.” And so that’s mute the world and build your own. His entire world is his business. And anything outside of that, he doesn’t care about. He’s just unbelievably focused.

Brian Halligan: I thought you were going to say the word “obsession.” Is it the same thing?

David Senra: I think they’re closely related. I think if you are intensely focused on something, I don’t know anybody that’s intensely focused on something that you wouldn’t call obsessed.

Brian Halligan: Yeah.

David Senra: But I think focus—the difference between focus and obsession is—what does Steve Jobs say? Focus is saying no.

Brian Halligan: Yeah.

David Senra: Like Jony Ive has this great interview that he did with Vanity Fair a few years ago. And he’s just like, “Steve was the most remarkably focused person I’ve ever come across.” And one time we were talking about this and he’s like, “Well, how many things have you said no to?” And Jony’s like, “I said no to this and I said no to that.” And Steve’s like, “No, no, you didn’t want to do that. Focus is saying no to a good idea that you really want to do because it distracts you from a great idea.”

Brian Halligan: Where does this come from? Like, you’ve looked at their childhoods. Is there something that happened early to them? Do they have very normal upbringings? Are they normal kids or are they weird? Like, where does this obsession-focused thing originate?

David Senra: So there’s a great line. The answer is it’s not one thing. I came across it in this book I read back in 2022. It was actually the biography of Francis Ford Coppola, because I’m also obsessed with—when I think of entrepreneurship, I’m pretty sure the word originated from French, and I think it’s like, “Has ideas and does them.”

Brian Halligan: Okay.

David Senra: And so, like, you built HubSpot. I built a podcast. He’s a filmmaker. I think it’s all the same thing, it’s legitimately the same thing. I had a two-and-a-half-hour conversation with Ed Catmull, founder of Pixar, yesterday. He’s like the same kind of artist that these animators and storytellers and directors—the same kind of spirit that Steve Jobs had. And Ed worked with Steve Jobs longer—I think 26 consecutive years, longer consecutively with Steve Jobs than anybody else.

But I would say—because most of them are men, especially when you’re going back in history, if you’re building a company 150 years ago, most likely a dude. The line I read in Francis Ford Coppola’s biography that put into words a recurring pattern that I’d noticed over and over again is he says “You can always understand the son by the story of his father. The story of the father is embedded in the son.”

And so that’s why when Charlie Munger says, “Hey, I’m a biography nut—” I had met Charlie before he died. He’d read hundreds of biographies by the time I met him. And his whole thing is if you truly understand the ideas, you have to tie it to the personality that developed them, which I thought was fascinating. And so what is happening in Francis Ford Coppola’s life? His dad was a brilliant but failed musician. And what happens when you have aspirations and you think you’re talented and there’s no evidence of that? He starts to resent this. And he’s one of the most cowardly people I’ve ever come across because he tells his young son, “There can only be one genius in the family, and it’s me.” And he would just put down his son. So the world is not giving him what he wants, and so he’s taking it out on his son like a fucking coward, right?

Brian Halligan: Yeah.

David Senra: It’s the opposite. I know you have a son. I do too. It’s like, tell him you can do whatever you want in the world. It’s the exact opposite. But this guy is a coward and a terrible father. And so Francis Ford Coppola internalizes that, and he has this crazy work ethic. At the time when Francis Ford Coppola becomes a director, a feature film director in Hollywood, there was no such thing as young directors at the time. And so he’s a few years older than George Lucas and Steven Spielberg, and they see this guy doing it and they’re like, “Oh, I can do it.” Fast forward, the guy would work 24/7, fall asleep editing the movie. Like, unbelievable work ethic. A few years later, a decade later, he wins an Academy Award. And he let his dad do the soundtrack—or the score—of the movie. And his dad wins an Oscar.

Brian Halligan: Mmm!

David Senra: For the score of the movie that his son made. It’s almost like full circle. It’s like, who’s the genius now? You wouldn’t have even had this opportunity if it wasn’t for me.

Brian Halligan: Are most of these people normal, well-adjusted people, or are they kind of broken from an early age? And that brokenness causes this obsession?

David Senra: Do you consider yourself a normal, well-adjusted person?

Brian Halligan: I wouldn’t consider myself normal at all.

David Senra: Exactly. I don’t either.

Brian Halligan: I’m relatively well-adjusted.

David Senra: What does “well-adjusted” mean to you?

Brian Halligan: I can function in society relatively well. I can have a conversation with you.

David Senra: Yeah, but we’re the same kind of personality type.

Brian Halligan: I’m not so focused that I can’t pick my head up and look around.

David Senra: Can you—do you have the patience? Like, let’s say if your son was small, and you’re put into a random collection of parents, they’re not entrepreneurs, they don’t have that kind of personality, can you sustain a conversation with them for a few hours or would you go crazy?

Brian Halligan: I think I’m better at that than the average entrepreneur. [laughs]

David Senra: Okay. I can’t.

Brian Halligan: My co-founder could not.

David Senra: Okay, exactly. So you know this personality type. No, they’re obviously not normal. I would not consider them well-adjusted. That doesn’t mean you have to be a prick. This is a very important point.

Brian Halligan: Okay, I wanted to ask you that, because a lot of the best founders of my generation were described as assholes. So you have to be an asshole to be a good CEO?

David Senra: No. No, definitely not.

Brian Halligan: Okay.

David Senra: No, absolutely not. I’m actually working on something. Daniel Ek, founder of Spotify, and we just hired an author who’s going to write this book that may never be published, but we’re building this framework, because Daniel is very interested in mapping out all the different founder archetypes. And for this exact reason. Because when he started Spotify 20 years ago, everybody tried to imitate Steve Jobs. Founders today, who are they going to imitate? Elon or Jensen. And he’s like, “I wasted years of my life trying to imitate a person I am not.” He is much more like a coach. He describes himself as like a team player. He’s a very different kind of archetype. And he would try to almost wear somebody else’s clothes or wear somebody else’s personality, and he’s like, “This isn’t working.”

Brian Halligan: Yeah.

David Senra: And what he realizes now—you know, he knows himself way better, now he’s in his 40s. He has two decades of experience. He knows a ton of other founders. He’s like, “Oh, there are all these different types. We don’t have words for them.” And so the project that we’re working on right now …

Brian Halligan: I love this.

David Senra: Yeah. And if you want to help, let me know, because I think some feedback, some insights into it would be great. Every founder I talk to, they’re like, “We need this.” Because Daniel’s point is more important than product-market fit or even founder-industry fit, he believes the most important thing is founder-problem fit.

Brian Halligan: Yeah.

David Senra: Like, think about Demis Hassabis from DeepMind. There’s one great company he had in him. It was DeepMind. He was put on this planet to do what he is doing. That’s the perfect example of founder-problem fit. Steve Jobs, founder-problem fit, what he was doing. Perfect example. And so hopefully what we’re trying to do is map out these archetypes—there might be six, there might be eight. We’ll try to figure this out. And what we’re doing is going through the back catalog of founders and using that to try to map all these different archetypes out, and then have a way for you to identify, oh, this is my archetype. And then here’s maybe 10 examples of historical founders that also have the same archetype. So maybe you should go read about them and how they ran their company and what they did, and then what other archetypes founders work well together. It’s going to take a long time, but yeah, this idea I reject it completely that you have to come from a broken home or you have to be an asshole or you have to be X, Y and Z.

I went up to Canada and recorded a podcast with Tobi Lütke, who’s very fascinating. And he said it the best way. He’s like, “There’s not one right way to do what you’re trying to do. There’s probably 100. You’ve got to figure out what’s right for you.”

Brian Halligan: Let me ask you about a specific archetype—and this is a little awkward, but if you think about autism spectrum disorder, it’s a very wide spectrum. And for some it’s debilitating and for some it’s a superpower. And I’m not as deep as you, but if I look at the kind of modern trillion-dollar company CEOs from Jensen to Jobs to Gates to Bezos, Zuckerberg, Elon, Larry Ellison, six out of the 10 have publicly said that they’re on the spectrum, and maybe a couple others are too. I don’t know. What is your take on that?

David Senra: I just found this Peter Thiel quote about this that I think is interesting. And I do think for some people, for Elon in particular, it’s definitely a superpower.

Brian Halligan: Yeah.

David Senra: Because he has this line and he says—this is a direct quote from Elon— “I think it’s a real weakness to want to be liked. A real weakness. And I do not have that.” This is what Peter said about this. Let me read, like, four sentences to you. “Many of the more successful entrepreneurs seem to be suffering from a mild form of Asperger’s, where it’s like you’re missing the imitation socialization gene.” Now I think Peter’s take on this is really good. “We need to ask what it is about our society where those of us who do not suffer from Asperger’s are at some massive disadvantage because we will be talked out of our interesting, original, creative ideas before they’re even fully formed.” Think about trying to talk Elon out of building SpaceX. Good luck with that. This is the last thing that Peter says. “Oh, that’s a bit too weird. That’s a little too strange. And maybe I’ll just go ahead and open that restaurant I’ve been talking about that everyone else can understand and agree with, or do something extremely safe and conventional.”

Brian Halligan: Yes. So it’s pretty common today, even the current founders.

David Senra: Definitely in tech.

Brian Halligan: If you look back to Carnegie and Rockefeller, is there any evidence in what you’ve been reading that that was pretty prevalent back then, too?

David Senra: No, I don’t think so. That’s the interesting thing. Maybe there’s something particular about technology. We’re in San Francisco today, you know, and everybody’s like, “You should move here.” I think it’s a very beautiful—you know, physical beauty—but I have a very unique vantage point in the founder ecosystem, because all kinds of founders listen to Founders. And what I would say about dropping into these different communities is like the problem with the Bay Area and San Francisco is they’re all memetic about being anti-memetic, so that therefore makes them the most memetic of all. And I think a lot of this is people pretending to have autism or pretending …

Brian Halligan: You think?

David Senra: Oh, yeah, 100 percent.

Brian Halligan: [laughs]

David Senra: We naturally imitate. And even though Peter Thiel spread, obviously, the issue with being memetic, that then I think increased people being memetic.

Brian Halligan: Okay. You know a lot of VCs, and there’s some tropes about what VCs are looking for in founders. What do VCs have wrong? Like, you’ve studied the best.

David Senra: I don’t actually spend any time with VCs.

Brian Halligan: Chip on your shoulder.

David Senra: Yeah.

Brian Halligan: Carnegie, Ford, Jesus, da Vinci, Rockefeller. Did they all have a chip on their shoulder?

David Senra: I don’t know about all of them but, like, we could take specific examples. Like, if we go back to that father, the impact that the father has on the son, right? I mean, Rockefeller’s father was a bigamist. He had multiple families. He was a scam artist. He would try to cheat his sons. This is in all biographies—and I collect obscure Rockefeller biographies. I probably have, like, 15 of them. I made my own biography. I have a 1,700-page transcript that I’m going to do an episode on of Rockefeller giving this interview later in life. You can’t buy it. I got it from the Rockefeller Archives. I printed it and fucking bound it.

Brian Halligan: Nice.

David Senra: That’s how obsessed I am with Rockefeller. And it’s clearly that, like …

Brian Halligan: Was he on the spectrum?

David Senra: No.

Brian Halligan: Okay.

David Senra: I don’t think so.

Brian Halligan: But he was obsessed.

David Senra: Focused. And part of this …

Brian Halligan: Did he have a chip on his shoulder?

David Senra: Yeah, sure.

Brian Halligan: Did they all?

David Senra: I’m trying to think of counterexamples that did not. I can’t think of one right now. I’m sure …

Brian Halligan: So generally, yes.

David Senra: Yeah, generally, yes. I think talking absolutes, we’re obviously going to find some kind of example. But yeah, generally, yes.

Brian Halligan: Okay. This is sort of the immigrant advantage. VCs that are immigrants, people who landed in this country. I interviewed Kaz from …

David Senra: Opendoor.

Brian Halligan: Yes. Who I love, by the way. There just wasn’t a lot of options to him, and that risk-adjusted option, starting a company, was the best option. What is your take on that? It’s sort of a common trope amongst VCs. They like the immigrant advantage.

David Senra: I can only speak from my personal experience. My dad was born in Cuba. I’m the son of a Cuban immigrant. I grew up meeting people that came to this country, that risked their lives, literally on fucking rafts. And think about how much you love your son and how bad Cuba had to be and communism had to be to put your 14-year-old or 9-year-old son on a raft and hope to make that 90-mile journey to South Florida.

Brian Halligan: Yep.

David Senra: What does that tell you? That had a profound impact on me. And this is where I’m like, this is the most pro-American, pro-capitalist person that I know. Just because it’s like, no, I know what we have. I’m unabashedly pro-American, pro-capitalist. I think a lot of these people, even if they don’t become entrepreneurs, they have fierce work ethics, because they’re like, “Oh my God, I didn’t have any opportunity. Now I come to this country and it’s unlimited opportunity.”

Brian Halligan: Yeah.

David Senra: And it’s weird that people that their families have been here for multiple generations think, oh, there’s no opportunity, everything’s gone, this sucks. It’s like, yeah, look at what you have.

Brian Halligan: One of the things that surprised me when I looked at the modern tech CEOs, only three of the ten were immigrants. Jensen was an immigrant. Elon was an immigrant from South Africa. Sergey was an immigrant from Russia. Most of them were born here.

David Senra: But those three are responsible for what, like, 80 percent of market cap? [laughs]

Brian Halligan: There’s some other winners on the list, though. I was surprised. I thought it was going to be eight out of the ten.

David Senra: Bezos’s dad was a Cuban immigrant.

Brian Halligan: Yep. A bunch of them had dads.

David Senra: Bezos is a Cuban Latino.

Brian Halligan: Three out of the ten were immigrants. Three out of the ten dads were immigrants. But it certainly wasn’t the common factor.

David Senra: I would never be a VC in my life, but if I was, I wouldn’t waste time trying to be like, here’s these patterns and I’m going to run this sort of rubric. For me, I don’t even—I barely invest. And my whole thing is just like, I don’t—the investments I’ve done, it’s just like, I don’t even want you to tell me what the company name is or what it does. I just bet on you. Like, I knew for a fact that there was no way I wasn’t going to succeed. So I will fucking kill myself before I fail. And that’s what I would look for. I wouldn’t look for chip on shoulder, immigrant, anything—this person is going to figure it out. Like Ed Catmull yesterday, one of my favorite things he ever said. And keep in mind, Steve Jobs said he learned more about managing highly talented people from Ed Catmull than anybody else in his career. That’s a hell of a compliment. And Ed goes, “It’s all about the people.” Because he’d give these talks and he’d ask, like, what’s more important, ideas or people? And he’s like, “No one realizes this is a false dichotomy.” It’s like, ideas come from people, therefore people are more important than ideas. And his whole thing was it’s all talented people. So he’s like, if you give a great idea to a mediocre team, they’ll fuck it up. If you give a mediocre idea to a great team, they’ll either fix it or throw it out and create something new. So that’s what I would look for. Like Travis from Uber, just look into his history. That dude was going to make Uber work.

Brian Halligan: Yep.

David Senra: Or he was gonna die trying.

Brian Halligan: Yep.

Brian Halligan: Okay, you studied all these folks. Some founders who walk through the door at Sequoia, they’re solo founders. Some are co-founders, some have big teams. For the most part, when I look back at it, some had co-founders at the beginning, but generally it was the one person that drove the company.

David Senra: It’s always one.

Brian Halligan: And that other founder sort of …

David Senra: There could be some examples, but this is also …

Brian Halligan: Not many.

David Senra: Doesn’t—again, I don’t pay attention too much to the start-up scene, doesn’t Y Combinator heavily recommend co-founders?

Brian Halligan: I think in general the conventional wisdom is co-founders is a very good idea. In fact, MIT did a big study and they said the optimal number of co-founders is three. Not sure I buy that. Anyway, you spent some time with Charlie Munger, who was not the co-founder of Berkshire Hathaway, but sort of was.

David Senra: Yeah.

Brian Halligan: What have you learned about that co-founder situation? What about partnerships? You’ve studied all these folks.

David Senra: So we’re at Sequoia. I think people should read the foreword to the updated version of Michael Moritz’s book, Return to the Little Kingdom. So it’s a book he wrote before I think he even was at Sequoia. So it’s the first six years of Apple, then he did this updated version like 2009, 2010 called The Return to the Little Kingdom. Read the foreword of that book.

Brian Halligan: Okay.

David Senra: First of all, Moritz’s writing is fucking incredible.

Brian Halligan: Great writer.

David Senra: Oh my God. I want to do a podcast so bad on the biography he did of Don Valentine. It’s like the perfect biography. It’s like 60 pages long.

Brian Halligan: Believe it or not, I never read it.

David Senra: Oh my God, you need to do that today. Read it this weekend.

Brian Halligan: Okay.

David Senra: It’s phenomenal. He was talking about, you know, Steve is singular. It’s like, when had anybody essentially refounded—the way he frames it in the foreword, he’s like, Steve refounded Apple. He didn’t found Apple once, he founded it twice. And the second time he was alone. And then he pulled off the craziest turnaround in technology history. And so this is when I think of when they’re like, “Oh, Buffett’s not the founder of Berkshire Hathaway because it was—” shut up. And just like Munger. Munger’s his co-founder, dude.

Brian Halligan: Carnegie, Ford, all these folks, there weren’t many partnerships.

David Senra: No, that’s not true. So Carnegie didn’t even run his company. This guy named Henry Clay Frick ran his company. There’s a great biography on this I’ll send to you. You’ll love it. It’s called Meet You in Hell, and it’s about the bitter partnership between Andrew Carnegie and Henry Clay Frick.

Brian Halligan: Okay.

David Senra: Frick was the operator. Carnegie was often sailing around the world when Frick was the one building Carnegie Steel, and then kind of forced the sale to JPMorgan. It’s a fascinating story. Anytime there’s this new technological change and disruption, there is physical violence. And we’re seeing this with the attacks against the data centers and the founders of these AI companies. That is unbelievably predictable. It recurs throughout history. Frick, let me tell you about Frick. They’re going through this. It’s the Industrial Revolution, there’s all this change. You know, when you have strikes, people are—just go read the history. They died over this. Frick got shot in the neck. An assassin went into his office, shot him in the neck, grazed him, right? Then they arrested the guy. Frick had it sewn up and insisted on finishing his day’s work and then went home. So Frick is a very badass dude.

Brian Halligan: Is this an exception though? Like, is co-founders that are partners that last an exception rather than sort of …

David Senra: I would take them one on one.

Brian Halligan: You have 400 for, crying out loud.

David Senra: No, but okay, so Carnegie made all the money. He was the largest shareholder, but Frick was running the company. He was smart enough to acquire Frick’s company. How about Ford?

David Senra: No, Ford was an autocrat.

Brian Halligan: Okay.

David Senra: And wouldn’t listen to anybody else. And remember, by 1919 he owned a—he bought out all his fucking shareholders. He owned 100 percent of Ford Motor Company. Rockefeller built a team of founders. If you look at his board—it’s not a board, but they call them “partners—” all the people taking dividends from Standard, almost every single one was a previous founder. And he made essentially a board, or a company of founders. He happened to be the dominating personality. It was much more of like a—I don’t even know how—there might have been a dozen of them or eight. I forgot the number, but there were a lot of them. I talked to Munger about this. He was just like, Buffett is a once-in-a-century talent. And he’s like, you are so arrogant. Because Munger had a big ego. Like, when I met him, he told me the funniest thing.

Brian Halligan: I’m actually surprised to hear that. I thought he subjugated his ego a lot.

David Senra: He talks about this. He used that word “subjugate.” That’s exactly what he said. But he goes, “If I could do life again—I always thought I was smarter than everybody else. If I could do life again, I’d still think I was smarter than everybody else, but I would do a better job of hiding it.”

Brian Halligan: [laughs] Okay. Okay.

David Senra: But it’s funny. He goes, “I thought I was really smart, but I recognized the talent that Buffett had that I didn’t.” And Buffett was more singularly focused. He wanted to fish and boat and design architecture and do real estate and do all this other stuff. So he’s like, “How arrogant would I have to be to not subjugate myself to a once-in-a-century talent?”

Brian Halligan: Got it.

David Senra: His thing was more of, like, Buffett let him shape his mind and his thinking. But he realized that Buffett was the driving engine behind their success.

Brian Halligan: One of my a-has, though—and I haven’t listened to all your podcasts—is I don’t think there’s a lot of co-founding teams that lasted the test of time. I think it’s pretty rare. And I kind of see that today in Silicon Valley. There’s kind of one dominant person.

David Senra: Yeah. And then they go away. That second person, usually—Wozniak went away. All the people that—the co-founders of Facebook went away.

Brian Halligan: It’s pretty common.

David Senra: Yeah. This was my argument about this. It’s like, now maybe that one guy needed these other people at the beginning, but there’s always just one. There’s a singular drive, usually a singular driving force behind the company.

Brian Halligan: Let’s talk about these individuals. You get inside their heads. And some people have positive self-talk. I have negative self-talk.

David Senra: Still?

Brian Halligan: Yes.

David Senra: I just changed this about myself. It’s the best ever.

Brian Halligan: Okay. I’ve tried. What about these people you’re interviewing? Do they have imposter syndrome? Do they have negative self-talk that they overcome?

David Senra: The imposter syndrome is an interesting idea. An interesting question. I can’t think of anybody, I think, that has imposter syndrome right now. You still do?

Brian Halligan: Yeah, I feel kind of nervous right now.

David Senra: Why are you nervous?

Brian Halligan: Just am.

David Senra: [laughs] So I don’t know about the imposter syndrome.

Brian Halligan: I was just in a board meeting for the last three hours. Little nervous. It’s like, what am I doing here?

David Senra: Interesting. One of the greatest pieces of advice that Steve Jobs ever got he got from Nolan Bushnell. So Nolan Bushnell was, like, nine or ten years older than him. He was his mentor, founder of Atari. And he told Steve, he’s like, “If you pretend to be in control, everybody else will assume that you are.” [laughs] Steve took that advice and ran with it. So I don’t know about imposter syndrome. What was the other part of your question? Oh, negative self-talk.

Brian Halligan: Yeah.

David Senra: Yeah. I mean, Jensen. Dude. Like, he wakes up every day and he says he looks in the mirror and says, “Why do you suck so much?”

Brian Halligan: Yeah. Do you think that’s common?

David Senra: I mean, then you think about Elon. He says his mind is a storm. He doesn’t see—he seems to embrace chaos and need some kind of foil or some kind of problem. He seems to be freaked out when things are going well.

Brian Halligan: Yeah.

David Senra: So I definitely think he’s got a dark mind.

Brian Halligan: I’m kind of negative inside, but as a founder trying to project positive outside.

David Senra: I think it’s way more common. The best founders don’t sleep on wins. They essentially do something great, they’ll celebrate for, like, a day and then back to it. So I just did Tony Xu of DoorDash, who I think you guys were investors in. And his whole thing is like, “We got so much more to do.” He’s like, “Okay, we had something good happen. Like, let’s go out to dinner. And by the time the dinner—before dinner’s over, I’m thinking of the 17 things that are not going right.” And that’s why he’s great.

That’s also different than, like, being super critical and negative. And I think for me, Brad Jacobs, who started eight separate billion-dollar companies, he’s the one—reading his book and then building a relationship with him. I don’t know what happened. This has never happened in my life, but just something about being around him, because he has 45 years of experience as an entrepreneur, longer than I’ve been alive. And he used to be fucking ruthless with himself. He’s like, “It’s not serving me.” And we were talking about this. He’s like, “You love what you do.” He’s like, “Would you stop? Your source of drive, that negative source of drive is not serving you anymore. Now you love what you do. You found what you think is your life’s work. Your inner drive should be generative. It should be like, ‘Hey, I’m trying to make something that’s good for the world that I love to do, that I’m very proud of.’”And I’m telling you, it was almost like—might not have been overnight, but pretty—there’s just something that clicked. I’m like, I’m done with that. And now it’s just like I wake up every day and I’m like, I cannot believe! Like, I was texting my team last night when we got done with Ed Catmull. I was like, “How is this my life?”

Brian Halligan: Maybe that negative self-talk is what got you to where you are today.

David Senra: But then your fuel source has to change, because it could also destroy you.

Brian Halligan: Fine.

David Senra: And so it’s like, I don’t want to do something for five years, for ten years, for fifteen years. I want to do it forever. If you look at the people I’m selecting to talk to, they’ve been doing it for 30 years, 40 years. I’m obsessed with people that—people say, “Oh, if you love what you do, you do it for free.” There’s another level. If you love what you do, they couldn’t pay you to stop. Those are the people I love.

Brian Halligan: Yes. Okay. You brought up something interesting about platform changes. The Industrial Revolution, obviously a huge platform change. Even Henry Ford and the assembly line, kind of a big platform change.

David Senra: Massive.

Brian Halligan: When those things happened, did the profile of the founder CEO change? And did the way they ran their companies change? Because we’re going through something, maybe bigger, maybe not, but probably bigger now.

David Senra: What do you mean by the profile change?

Brian Halligan: I’ll give you an example. Paul Graham talked about this thing as founder mode and manager mode. Manager mode being kind of Jack Welch, military style, organizational structure, very top-down. Founder mode being Brian Chesky, who’s pretty distrustful of conventional wisdom, thinner layers of management, gets right down to the coalface as much as possible.

And so those are sort of the two modes I see of CEOs today. People are kind of tilting towards founder mode. In the Dorsey interview we were talking about a second ago, Jack Dorsey’s doing—I call it Dorsey mode, where he gets rid of the org chart, he gets rid of titles, and more and more of the decisions are actually made by his AI system in the middle of the company. And the people are in charge of just giving more context to that AI system in the middle, circular-shaped. They’re feeding context, they have judgment on the outside. Over time, the AI system makes very few of the decisions today, but maybe five percent, ten percent, and the percentage of decisions the AI system makes versus the humans starts to flip. And so I kind of call it Dorsey mode, like a new way to think about building a company—far fewer people than you would’ve needed in the previous generation. Did something like that happen to the profile or the way they built companies back in the previous …?

David Senra: It’s a great question. I just asked Michael Dell this, because if you think about Dell, he started his company, he was 19 with $1,000. He’s like, “Hey, I’m in my University of Texas dorm room, and I’m gonna take on the biggest company in the world, which is IBM.” Which is an absolute batshit crazy idea.

Brian Halligan: Yes.

David Senra: Most people don’t know—I just had a conversation with Marc Andreessen about this on my podcast. IBM was the first company in history to hit $100 billion market cap. It had 80 percent market share of the entire technology industry. I think Marc said on the podcast, that’s like having 10 Googles. It’s just like we haven’t seen that level of domination ever since. It’s just a crazy thing, and he wound up succeeding, and Dell was actually profitable every single quarter for the first, like, 20 years of its existence. It’s a crazy feat.

And I’m always skeptical that this time is different, because everybody in history says this time is different. And so Michael has had to navigate through how many different platform shifts and technological revolutions. I asked him that, because to me it feels different. And he’s like, “No, this is not like anything else that I’ve been through.” I actually think the way to run a company—Tobi Lütke believes this, too—I do think the way to do it and how you could do it and what’s available to you is completely different. This time, in my opinion, is actually different because the amount of leverage …

Brian Halligan: I think it is too.

David Senra: Yeah, exactly. So that’s what I would say.

Brian Halligan: I think the shape of the organization changes. I think the number of people you need changes. I think the way you compensate people—because you have 100x people now that are really proficient with these tools—changes. I think the planning cycle changes, because it’s moving so fast. I actually think it’s different, compared to, like, I went through the internet in the 1990s when I started my career and Google came along and SaaS came along and mobile came on. This is a lot different.

David Senra: There’s a great line in the Almanac of Naval that my friend Eric Jorgensen wrote about the book of Naval Ravikant. And he says, “In the age of infinite leverage, being at the extreme of your craft is very important.” That was before AI. And AI is just leverage. And I think this is why we talked about—I think we started this conversation, but me and you have had this conversation before. It’s like the premium on focus. Just trying to be the best in the world, whatever it is that you do, you’re going to reap so many more rewards. Being at the very frontier and the extreme edge of your craft is going to be unbelievably valuable to the point where you just said, you know, you can have somebody that makes 1x and then you can have the most talented people—we’ve already seen some of this. Well, they’re not 100 times more valuable. They’re like 1,000 times.

I don’t know. So I’m really close to John and Jordi of TBPN. I’m obsessed with podcasters. I’ve built relationships with all of them. And the way I put this is yeah, maybe they bought the show—the show is incredible. I spent a lot of time talking to him about this, but Jordi came into podcasting and it wasn’t like he was like 2x as good a marketer as the next best podcaster. He was like 100x better. And if I was OpenAI, I would make him the CMO of OpenAI. The value is like, he could produce—I’m not saying he will, I’m saying he could produce billions from a single individual. And the ideas that come from his very unique brain when it comes to marketing. He’s really gifted at this. Look what he did for this show that was only 17 months old. Everybody’s talking about oh, all these people are trying to clone them. It’s like, they can’t clone their minds. They have no idea what was coming. And so yeah, I do think you’re going to see people like that in other areas—marketing obviously, research, everywhere else—that you should pay them 10,000x.

Brian Halligan: I think that—I don’t know about that. One other thing that’s different I want to press you on a little bit is I was a preacher of focus inside of HubSpot. Every year it’s like, we can only do three things. What are the three things? What are the 50 we’re not going to do? I’ve noticed that the modern, AI-native CEOs like Winston from Harvey and Anton from Lovable, Mati from ElevenLabs, they’re not that focused. They’re doing tons of stuff and they’re able to do stuff fast. Bezos used to talk about his one-way doors and two-way doors.

David Senra: Yeah.

Brian Halligan: Things that used to be one-way doors, like we’re going to do a big initiative, we’re going to go international, some big thing—a lot of those one-way doors are two-way doors now. Like, okay, let’s press for a month and see how far we can get. Okay, if we miss, let’s just go back. What’s your take on that, that maybe focus isn’t as important in the age of AI?

David Senra: I don’t know if I have a take on it. I would say I’d be very wary. Like, these people that you mentioned have built great products. They haven’t built durable businesses yet. We have to see how this plays out.

Brian Halligan: Yes. Still early.

David Senra: Yeah. So that’s the issue I would have. It’s like, yeah, maybe those are good ideas, but I’m interested in people that build durable businesses. Again, I don’t want to be acquired. I want to be around running my business forever. I’ve spent a bunch of time with older founders. I’m talking 70s …

Brian Halligan: A lot of time with older founders.

David Senra: No, but I’m talking about recently, like 70, 75, 80 years old. You know what I realized? Like, if you sell your main thing, get out of the game completely. Because if you sell your best idea and then you have another decade, two decades, 25 years ahead of you, and then you’re just working on a bunch of bullshit. I don’t know how many people can found, you know, multiple great companies in their lifetime. Very rare. Elon, like …

David Senra: I think the second-time founder thing is really overrated, because most of the successes are first time.

David Senra: And so what I’ve seen is people that either sold their best idea that was a generational company, or maybe they had a falling out or something happened. Like, now you fast forward, they’re 75 years old. This happened maybe 25 years ago. You don’t want to be in that spot. And so my point is you’re all in or all out. But why would you be all in on your second, third, fourth, fifth best idea? And then they try to recapture that magic, and it’s almost impossible—especially at 50 or 60—to do what you did at 25 or 35. Like, that’s very difficult. That was just some weird sixth sense I had about having these conversations where it’s like, man, this is so far down from what you had accomplished in the past. And you’re just like, oh, I have to play the game. It’s like, I would just—if you’re out, then you’re done for the rest of your life. Go fucking on your boat or go do whatever.

Brian Halligan: They’re not capable of being out.

David Senra: And I don’t think so either. That’s why you don’t sell. And so that’s what I mean about being very hesitant of taking knowledge or ideas and be like, “Oh, look, this company that has raised a bunch of money and is a stone startup is working on 15 different products.” Well, let’s see how the—give it time. Let’s see how it plays out. I don’t know.

Brian Halligan: It’s fashionable in AI worlds for people to say the best founders have great taste. What’s your take on that? And when you look back through the 420 that you’ve studied, is that a common thing or is that new? Is it bullshit?

David Senra: I think taste is very real. Now what’s coloring this is like, I’ve been a big fan of Rick Rubin.

Brian Halligan: Yeah.

David Senra: Taste is very real. The guy’s built a wonderful career. Same thing. Started at 18 in his dorm room. He’s 62, 63, still doing the same thing. Why do people want to work with him? Because of his taste.

Brian Halligan: Yeah.

David Senra: And I realized he’s scary good at making podcasts, too. And we were talking before we started recording and I go, “Dude, I’ve been thinking about you, why you’re so good when most people that make podcasts are very, very bad.” And I go, “I realized you took a skill that …”

Brian Halligan: I’m very, very bad at this. Is this your way of telling me?

David Senra: No, I wouldn’t be here if you were.

Brian Halligan: [laughs] I’m kidding.

David Senra: Wouldn’t be here if you were. No, but I realized he took a skill from music and applied it to podcasts.

Brian Halligan: Yes.

David Senra: Which if you think about what his main thing—I go, you’re a professional listener. And he lit up. I started explaining my theory on why you’re so good at podcasting. And he goes, “Stop.” He goes, “We have to stop. We have to record this. This is too good.” And so he agreed with that, that his essential skill set was not just his taste, but most people when they’re talking—maybe even when I’m talking, maybe you’re listening, maybe you’re just waiting to respond. And it’s very common for humans. He’s just like not forming any opinions or judgment. He’s just really interested in these people. That’s why he’s very selective about who he works for or works with. And so yeah, he has very real taste.

Brian Halligan: Is he an exception, though?

David Senra: Oh, of course.

Brian Halligan: Like, did Bezos have taste? Jobs obviously had taste.

David Senra: Jobs obviously had taste.

Brian Halligan: Did Jensen have taste? Does Zuckerberg have taste?

David Senra: I think—so we mentioned the Broadcom guy, Hock Tan I think is his name.

Brian Halligan: Yeah.

David Senra: He was just speaking about this, and his whole thing was like, he thinks these founders that pontificate and, like, “I saw this strategy coming—” I think his company’s like $1.5 trillion now. He’s like, “Yeah, I had no fucking idea this was going to happen. The opportunity was in front of me. I made a good decision. Then I was like, oh, what can I do now that I got to the next rung?” And he looked around and then he’s like, that was a strategy. He’s like, there’s no fucking way. It’s way too many moving parts, way too complicated. I could not have predicted 20 years ago it was going to happen.

So I don’t know. I think be very wary of anything where there’s like this echo chamber on X where the current thing, the thing of the day, I think that’s almost useless to even pay attention to. So I don’t even think about it.

Brian Halligan: This is exactly what I want to ask you about. Like, a lot of the people that you see on X today or you read their biography, you’re studying them after they’re incredibly successful. They’ve hired a PR firm to make everything look good. They get advice on how to post on X and how to be in the world. Advice to founders, should they just be themselves or should they get some help?

David Senra: Depends on who you are as a person. I mean, some of these people are terrible people or they’re terrible communicators. I would not be yourself, buddy.

Brian Halligan: [laughs]

David Senra: I don’t want to tell you, but yourself sucks. So I would not be yourself.

Brian Halligan: How much shaping should you take? Like as a CEO, I remember coming up, and we’re going public and we hired people trying to shape me. And we did a little of it and I think it worked. Is that a good idea or a bad idea?

David Senra: I think obviously depending on the industry you’re working in, who you are as a person, everything comes down to, like, who you are as a person. Like, we have one shot at life. How do you want to do life? This is why I like reading biographies. It’s like, yeah, there’s a lot of good business ideas in there, but essentially every week I’m just like, this is how this person did life. We’re all doing life. We’re alive. You’re listening to us. We’re doing life. How do you want to do it? I want some ideas on how I could do life. And so for me, I’m unmanageable. I’ve run a fucking podcast for 10 years that had no employees by myself. What does that tell you? Like, I have a very hard time working with other people. I’m very disagreeable and, like, micromanaging and everything else. And my new podcast, like, ask my team, I am fucking—I can be ruthless. In a nice way. I’m not mean, but like, “Nope, we gotta redo that.”

Brian Halligan: Most of these great founders are disagreeable through time.

David Senra: Yeah, for sure, for sure. But what I would say is like, I don’t want to censor myself. A good friend of mine was mentored by Sam Zell for 25 years. And I was doing another episode on Sam Zell. He’s like, “Come over for dinner and I’ll give you some Sam Zell stories for your episode.”

And what you know about Sam is like, he always ran his own money. His company was like his family office and he made the investment decisions. He would raise money on an individual deal-by-deal basis, but never a permanent capital structure, no fund. You know, why do you do that? And my friend said the funniest thing. He goes, “Sam was constitutionally unsuited to manage institutional capital.” Meaning Sam was a wild man that was uncontrollable and he would say shit. He had no filter and he didn’t want LPs calling him saying, “You’re not professional,” that kind of thing. Sam knew who he was.

So it depends. Like, Sam should be who he is. Maybe in this case, this other founder shouldn’t. It really just depends on, like, the industry, who you are, what you’re going to be. I don’t want to have multiple sides of me. I’d rather just be like, this is what I believe. This is what I think is interesting. Like, if you think about founders—like when I go through the books, everybody’s like, how do you pick out what you want to talk about? Like, what are you thinking about when you’re reading? And I’m like, absolutely nothing. Like, I’m reading, that line sticks out to me for some reason, I underline it and then I jot down what comes to mind. And then before I sit down to record, I just go back to the highlights. And if I read it again the second time and it’s still interesting to me, I put it on the podcast. There’s no thinking at all. It’s all instinct.

Brian Halligan: Okay. You’re an interesting case on this because you did 400-plus podcasts of mostly dead people, and now you’re doing very much alive people. And it’s a little bit like you never want to meet your heroes.

David Senra: I met my hero, James Dyson.

Brian Halligan: Okay. Let’s come back to that. Any surprises in meeting these people face to face versus books? Is there whitewashing in the books? Are the people face to face very different than their whitewashed external presence?

David Senra: I would have to imagine if you’re—especially for autobiographies, you write an autobiography of your life, I write an autobiography of my life. Come on, man. Of course you want to look the best. And, like, even if you don’t lie about stuff, you’re going to omit stuff that makes you look bad.

Brian Halligan: Of course.

David Senra: And so this is the—I always get this, like, well, how do you know the stuff in the books is true? You don’t. But we’re not taking a history test. If I read an idea in the book that said, you know, Sam Walton found a way to beat back bureaucracy, and that never happened, but it’s still a good idea, and I apply that idea to my business. All I care is is this a useful idea? I can’t prove, nor do I care if it’s true. I’m just looking for interesting ideas. It’s not a history test. What I would say about all the people I’ve met is they’ve been unbelievably kind and generous and thoughtful. But I also don’t work for them. So who knows? And I’m not in their family. I’m not in their house. Like, it’s a different interaction. I don’t think …

Brian Halligan: Do you think people today, the great founders, are different than the ones of a hundred years ago?

David Senra: No, no. Same personality type.

Brian Halligan: Same phenotype.

David Senra: Yeah.

Brian Halligan: What else is in common?

David Senra: Kind of personality traits? So obsession, high-level disagreeableness.

Brian Halligan: Talk about that. So somebody comes in to pitch at Sequoia, let’s say. And some people are very charming and some people are a little disagreeable. I think it’s just very natural to want to do business with the very charming person. Is that a bad instinct?

David Senra: I’ve done like 15 episodes on Steve Jobs and read almost everything I could find on him. And I learned something about him that I never knew yesterday from Ed Catmull. And Ed said that Steve fired two people off the Pixar board, and he fired them because they never disagreed with him. And he’s like, “If they don’t disagree with me, what value are they giving me?” He wanted you to fight back and to be …

Brian Halligan: He was disagreeable himself.

David Senra: Yes.

Brian Halligan: Are they all disagreeable?

David Senra: Rockefeller had very advanced social skills, I would say.

Brian Halligan: Okay. Did they all?

David Senra: No, no, no. So Rockefeller is an interesting thing, because there are people that worked for him for, like, 40 years that said they never heard him raise his voice and never said an unkind word. That’s crazy. And then even the way he would arbitrate disagreements between him and his partners was essentially like, there’s this one thing where they wanted to invest, like, $3 million into some kind of new technology that I think would transport oil faster or refine oil faster, something like that. And there was a huge disagreement on the board. And Rockefeller sat there quietly and let them fight. And then he said, “I believe in this. If you guys don’t want to do this, I’ll put up the money myself. If it works, Standard Oil can pay me back. If it doesn’t, I’ll eat the $3 million.” And then his partner’s like, “Well, if you could take the risk, we can too.” And that’s how they agreed to do it. That’s not disagreeable. That’s something else.

Brian Halligan: Yeah.

David Senra: It just depends on the person. But yeah, there are these traits—obsession, focus, cost control, obsessed with having the lowest cost. They see that advantage compounds over and over again. You don’t see that with the new technology founders at all. I think it’s a great disadvantage. Micromanagers, what Paul Graham calls “founder mode.” That’s not new at all. I’m a huge fan of his essays, but when that essay went viral, we’re like, we’re bringing this back. I’m like, this is a new thing. It’s like, this is not new at all.

Brian Halligan: Interesting.

David Senra: At all. Nothing is new in this at all.

Brian Halligan: What is new?

David Senra: I think what we talked about earlier, like what Jack Dorsey was saying, what Michael Dell was saying. That I do think—I mean, Tobi Lütke, when I talked to him, he said that we’re going to look back on 2026 as the year that every single business was up for grabs. That you can rebuild almost every single business AI-native and have a massive advantage. And I think that’s an interesting thing.

Brian Halligan: When you look back at all these folks, how many of them had great, well-balanced personal lives, great families, had a really deep life beyond the business?

David Senra: I think three of them.

Brian Halligan: Out of all of them, only three.

David Senra: I think Ed Thorp, who is a very fascinating character, created the first quantitative hedge fund, invented the way to count cards for blackjack. Phenomenal investor.

Brian Halligan: But the fact that there’s only three …

David Senra: Three. Him, Sol Price. Do you know who Sol Price is?

Brian Halligan: No.

David Senra: So Sol Price is the most influential retailer of all time. Sam Walton said he took more ideas from Sol Price than anybody else. Jeff Bezos took a lot of ideas for Amazon from Sol Price, so he knows who he is. Bernie Marcus literally got the idea for Home Depot from Sol Price. Jim Sinegal of Costco literally said, “I didn’t learn a lot from Sol Price. I learned everything I know from Sol Price.” So he created all these billionaire retailers. The other one I would say is Brunello Cucinelli, but that was his autobiography. And I heard that may or may not be true.

Brian Halligan: Advice to founders. So I spend all my days with founders trying to build trillion-dollar companies. Advice for them on their lives?

David Senra: I don’t ever give advice.

Brian Halligan: Why not? I’m asking you for advice right now.

David Senra: For you?

Brian Halligan: Let’s use me as a proxy.

David Senra: I think people are going to do what they want to do, and so they’ll seek out useful information. But I think these people that go around—not you, but, like, anybody that just goes around trying to identify what’s going on in somebody else’s life, like, I think it’s almost relatively useless. I think people literally do what they want to do.

I talk to a lot of founders. Now there is this thing where they find it very useful to have a conversation. They kind of like dump what’s going on in their company to me, and I kind of run it through everything I’ve read. And maybe I come up with something interesting, but I wouldn’t consider it advice. It’s just like, oh shit, Rockefeller ran into that situation. This is what he did, or Ford did this, or …

Brian Halligan: Is it possible to build a trillion-dollar company and have a very well-balanced life like Ed Thorp?

David Senra: I don’t even pay attention to public markets.

Brian Halligan: There’s 10?

David Senra: There’s 10?

Brian Halligan: There are 12, including the Middle Eastern oil companies.

David Senra: Okay, let’s just take the American companies.

Brian Halligan: 10.

David Senra: Any of those guys well-balanced?

Brian Halligan: Here’s what I will say about them that I thought was interesting. Only two of them are divorced. Most of them were married before they were famous and stayed married. And most of them married—their spouse was kind of an intellectual equal. They met them, and they were very accomplished on their own. And so they started out with an intellectually formidable partner very early and stuck with them. I thought that was interesting. Of course, Larry Ellison’s had four wives.

David Senra: I think six now.

Brian Halligan: Okay.

David Senra: But yeah, he’s doing some heavy lifting for these other guys. [laughs]

Brian Halligan: But I thought it was interesting that they all got married very early to peers. And how about through history?

David Senra: In history, they’re just like—they’re terrible husbands, like divorce, like just not …

Brian Halligan: I see.

David Senra: I would not consider them—in many cases bad fathers, too.

Brian Halligan: I see.

David Senra: Is this a very difficult thing to do? I remember I just finished reading Phil Knight’s autobiography, Shoe Dog, for the third time.

Brian Halligan: I love that book.

David Senra: And think about what he says at the very end. You know, like, he had two sons, one of them died tragically in a drowning accident. And he was trying to reconcile this as a grown 75-year-old man at the time. He’s having a hard time understanding this, that, like, this push and pull, like, I wanted to spend more time with my sons, but if I’m being honest, my biggest regret is that I can’t go back and do it all again. And in Sam Walton’s autobiography, you know, he sacrificed a lot of time away from his family to build Walmart. And he knows he’s dying. He’s writing the book when he’s riddled with cancer.

Brian Halligan: Did he regret that?

David Senra: No, that’s what I was getting to. And he’s like, “If I did it all again, I would do the exact same thing I did.” I’m very skeptical of these people that later in life, it’s like, “Oh, I have this regret,” because I think it’s personality type. It’s almost like a compulsion. If they played out life again, they’d want to do it the same way. I talked to Jeffrey Katzenberg about this, who’s very interesting. He swears he has no talent. He just throws hours at everything. It’s like, Jeffrey, you’re obviously fucking talented. But he was telling me about this. He’s like, “Listen, the biggest thing with your kids is, like, quality of time, not quantity.” He’s just like, “Don’t do it where you’re on the phone or you’re distracted. Like, if you only have 10 hours a week with them, make those the best 10 hours ever. Do a ton of planning with it, make it so that it’s so memorable with them.” I thought that was an interesting idea and recommendation.

But look at the people—like the AI race right now. This is the game of kings. I met Demis Hassabis. He just did an interview on Fortune where he’s just like, his schedule is he has his thinking time from like 11:00 pm to four in the morning, right? And he goes to sleep. Then he works a full day at the office the next day, then has dinner with his wife and kids and then does his thinking time again. You think he’s balanced? He’s got two workdays.

Brian Halligan: Yeah. Okay, you studied all these people. I spend all my time with Sequoia founders now. Advice to them, how to become iconic, someone that you would read their book and do an episode on them.

David Senra: I think the best founders don’t need advice. I’m very skeptical of this narrative that we back and discover the greatest talent. The way I would put this is like, Michael Jordan said something very interesting. He was at the end of his career and Kobe Bryant’s coming in. They’re like, we discovered the next Michael Jordan in Kobe Bryant. And he’s like, “This will happen again. There will be another me.” And he goes, “First of all, you didn’t discover me. I just happened to come around.”

And I think the best founders are like that. Like, they’re not discovered. They make themselves known. And I’m highly skeptical. Like, these are forces of nature. Again, go back to Mike Moritz, the foreword that he wrote in The Return to the Little Kingdom. In a paragraph, he can describe what a founder is. He’s like, these are irrepressible. This is the line he says about Jobs and the best founders. “They’re irrepressible forces of nature.” They don’t need your advice. They will find the information. And if they want it from you, they will seek you out. They will find you. But going around like, oh, I would paint that a little different or I would do it a different way. It’s like, they’ve got it.

Brian Halligan: Yeah, I think you’re mostly right about that. I don’t proactively give advice. If they ask me, I give it to them, and I think they’re good about sort of ranking it in their head and like, “I’ll take that, I’m going to throw that away.”

David Senra: And to the degree like I am somewhat helpful in this domain—and I’m trying to be—all I’m trying to do is like, hey, I’m going to go and read these obscure books. There’s a goldmine here of all this past entrepreneurial knowledge. No one’s fucking doing anything with it. I’m going to like a goddamn demon go and mine this for you. I’m going to make it into a podcast that you can listen to in 45 minutes or an hour while your eyes are busy doing something else, and hopefully push this information down to the next generation of entrepreneurs. I think that active service is a life well lived. But I’ll get to the end of my life and it’s like, they’ll figure it out. They’ll know what to do with it. Like, I don’t overexplain shit. You listen to Founders. Like, I don’t overexplain shit. It’s like, this guy did that. And even when they do ask me, I’m like, I don’t know, man. Ford did this way. This is the way this guy did this. It’s like, you pick what’s right for you.

Brian Halligan: One of the things that I think is interesting about you is there’s actually not that many patterns. Like, the whole episode I kind of push you on patterns.

David Senra: I would say it’s not formulaic. There’s patterns. There’s no formula.

Brian Halligan: Any other patterns we haven’t hit?

David Senra: I think just a deep caring and love of what you’re doing and the problem you’re solving. In some cases, it’s like—let me give you an example. Ed Catmull talks about the very first time he met Steve Jobs, before Steve got kicked out of Apple the first time. You know what Steve would talk about for an hour? He would just use the words “insanely great products” over and over again. It was important to him when he was 19, when he was 25. It was still important to him right when he was dying. He just was obsessed with insanely great products.

Brian Halligan: No founders ever talk about, I want to make a lot of money. How much do you think people being motivated by money matters? Or do you think they whitewash that out with, we want an insanely great product?

David Senra: I don’t think small egos build big companies. And therefore, this is what I actually think.

Brian Halligan: I don’t think small egos build big companies.

David Senra: I think all of these people have giant egos. I think some of them are just better at hiding it. And I think that what motivates most founders is not money, it’s control. And if you maintain control and you build a business or a product that makes somebody else’s life better, that’s all business is. A business is just an idea that makes somebody else’s life better. So if you maintain control and you build a product that makes somebody else’s life better, you wind up with the money anyways.

Brian Halligan: Yeah, it’s a side effect.

David Senra: Yeah. They know that they’re going to get the money.

Brian Halligan: Yeah.

David Senra: I can’t think of—I mean, Rockefeller …

Brian Halligan: You don’t think they’re born very motivated by money?

David Senra: Sure. Especially if you’re poor.

Brian Halligan: They have large egos. By the way, I looked through those 10 CEOs, the founders of the American companies. In general, there’s this narrative that they all grew up poor. In general, they were upper middle class suburban families. That surprised me.

David Senra: Especially in the tech industry.

Brian Halligan: Yeah.

David Senra: But Bezos was the son of a single mom, like—and his dad dipped out.

Brian Halligan: But mostly they were suburban, upper middle class families. Yeah. Like, Gates, Zuckerberg. Yeah, mostly. All right, any life advice for me? I’m on my second act.

David Senra: I think Dana White—there’s like a simple genius to how Dana White runs his company that I really admire. He told me something funny. He’s like, “I never read a single book on business. I’ve never listened to a single podcast,” which is hilarious. He said this because we talked a bunch after and his thing was just like, deeply know who you are. Like, you’ve got to know for a fact. And he’s like, “I’ve known exactly who I am for a long time.” This is what Dana was telling me. He’s like, “Understand deeply who you are, understand deeply what you want to do in this world. And then once you figure out those two things, you just wake up every day and get after it.” And I think there’s like this simple genius to that. Do you think when he started UFC, when they bought it for $2 million—$2 million with an M—that they were going to do—that there was such a thing—streaming didn’t even exist, right? It didn’t even exist. You stay in the game long enough to get lucky. That’s a maxim that repeats over and over again. And you think he could have predicted back then he was going to sign an $8 billion deal?

Brian Halligan: I like that maxim.

David Senra: Yeah, stay in the game long enough to get lucky. You guys are jumping around too much. This is what kills me about these founders. They have a million different ideas. I’m going to start, scale, sell. Okay, then what? Everybody’s like—I go, “What’s the best company that you can think of right now?” They’re like, “Oh, SpaceX.” Elon founded it when he was 30, 25 years ago. He didn’t jump around. Like, he did other shit, but he didn’t let go of that thing. All the value’s in the future. This is, I think, really important. But I think back to Dana’s point, it’s just like spend a lot of time understanding who you are as a person and what you want to do in the world. And then from there, you just wake up every day and opportunity handled well leads to more opportunity. And so Dana handled that opportunity well. Couldn’t have predicted he did an $8 billion streaming deal, right? And he goes, “What do you think my next deal is going to look like?” Obviously a lot bigger.

Brian Halligan: Yeah.

David Senra: I think that’s hugely important.

Brian Halligan: Okay. I want to thank you not just for coming on the pod, but I’ve been listening to your content for a long time, and as a CEO, it’s super helpful. It’s super helpful to, I’m sure, tons of CEOs out there. So you’re the man. I appreciate you. Thanks for coming on the pod.

David Senra: Thanks for the invite.

Brian Halligan: Thank you for being David Senra.

David Senra: Appreciate it.

Outro

Brian Halligan: I hope you like that episode with David. He’s a very interesting cat, very knowledgeable. I had three takeaways from it. First is he talks a lot about focus. I think it’s beyond that. I think it’s obsession. And this may be me, but I think in general at Sequoia, we look for founders that are obsessed with the problem. We look for people who have gone very deep down a rabbit hole and been obsessed with it earlier in their careers. And then today when they’re building the company to be very deep down that rabbit hole, have very deep founder market fit. Like, that’s a common trait of the best founders that he’s interviewed and the best founders that I’ve had on the show and the best founders that I coach is just a deep, deep obsession, the ability to mute the world and build your own. I really like that quote.

The second a-ha, this is kind of depressing. It is very, very difficult to have good work-life balance as a founder. He went very deep on 400 founders. Only three had what he thought was a very well-balanced life. This isn’t great news for me. I didn’t have a great balanced life. I didn’t have a lot of free time when I was a founder, and I don’t know a lot of successful founders that did. So if you’re thinking about starting a company or becoming a CEO, be careful. It’s a lot of work if you really want to do it well.

The last piece that I was curious about was this idea of imposter mode. I have imposter mode. I did when I was a CEO, big time. I was always a little bit nervous. I liked what David had to say about it. I liked even more what Brian Chesky has to say about it. When he was early in Airbnb, he kind of led from a position of fear. He had deep, deep imposter syndrome. And Brian has done a lot of work on himself, and now he leads from a position of love.

I’m trying to be more like Brian. Like, what I love is helping CEOs and founders like yourself go on that journey from early-stage startup founder to big behemoth legendary scale-up CEO. And I’m trying to lead from a position of love versus a position of fear. I recommend you do the same. Hope you like the episode. You can follow me @bhalligan on X, and we can chat about it more.