What David Senra Learned Studying 400+ Founders

The best founders kind of um they don't really rest on their laurels and they don't like sleep on wins. They

essentially do something great, they celebrate for like a day, and then back to it. So, like I just did Tony Xu of

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

investors in. He's like, "We got so much more to do." He's like, "Okay, we had a something good happen. Like, let's go out to dinner." And by the time of the dinner, before dinner's over, I'm thinking of the 17 things that are not going right. That's why he's great.

going right. That's why he's great.

[music] [music] Okay. Today, we have David Sacks on the

Okay. Today, we have David Sacks on the show. I've been a huge fan of his pod

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

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

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.

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.

What's the one thing they have in common?

If I had to distill every single thing down to one word, it'd just be like focus. They're just unbelievably focused

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 like today's founders. They are just much

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, is like mute the world and then build your own.

Yeah.

And so, like let me give an example of this. This This isn't out on my new show

this. This This isn't out on my new show yet, but I just spent a several hours with Dana White. I call him the founder of the UFC, even though it's like, "Oh, they bought company."

Yeah.

And Dana, first of all, is one of my favorite conversations I've 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 he self-described loser. He's just like,

self-described loser. He's just like, "I'm just a loser. I have nothing going on. But, I'm obsessed with fighting." At

on. But, I'm obsessed with fighting." At

that time, it's boxing. He's a huge boxing fan. And he has this idea, he's

boxing fan. And he has this idea, he's like, "I should just move to Vegas, the 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 like going back and forth, he's like, "This is stupid." He goes, "I'm a bellman. I could be a bellman at 35. This doesn't work out. I could be a

35. This doesn't work out. I could be a bellman at 35. I could be a bellman at 50. So, I have nothing. I have no wife,

50. So, I have nothing. I have no wife, no kids." And he just goes,

no kids." And he just goes, starts working in the industry, taking any job he can get, starts promoting, uh 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

nothing. They're in front of tiny crowds, there's no money. And so, he's on the phone cuz he's a repping two fighters, and one of the fighters is owed money by the UFC.

And he's like, "Dude, like you need to pay him." Like, and the guy screams at

pay him." Like, and the guy screams at him, the owner. He's like, "There's no [ __ ] money. There's no money." So,

Dana hangs up, calls the Fertitta brothers, whose their father built a casino. He's like, "I think we could buy

casino. He's like, "I think we could buy this whole thing."

What you realize is he's a missionary founder. I think the best founders are

founder. I think the best founders are missionary. Like, if you go back and

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 for Q million.

this thing." They buy for Q million.

Takes them like six years. He's making

no money. They're just they're losing money. They have to dump another 40

money. They have to dump another 40 million into it until it's profitable.

And he tells this whole story. So, I'll

get to the end cuz he's still been running it for 26 years. And now, they just did a, you know, almost an 8 billion-dollar deal for their TV rights.

At a time where, you know, he's making no money for the first 6 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 going to make a million dollars." He thought he was

million dollars." He thought he was rich. I can't even tell you what he told

rich. I can't even tell you what he told me he makes now. What he told me off camera it's just it would blow your mind. And the reason I bring this up is

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 really listened to a single podcast about business. All I did was like I'm the fan. So like when we bought the company I never sold tickets, didn't have any 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

your own. His entire world is his business and then anything doing outside he doesn't care about. He's just

unbelievably focused.

I thought you were going to say the word obsession. Is it the same thing?

obsession. Is it the same thing?

I think they're they're like closely related. I think if you were

closely related. I think if you were intensely focused on something I don't know anybody that's intensely focused on something that's not that you wouldn't call obsessed. Yeah. And but I think

call obsessed. Yeah. And but I think focus the difference between focus and obsession is your focus is what did Steve Jobs say? Focus is saying no.

Yeah. Like Jony Ive has this great interview that he did with Vanity Fair a few years ago.

And you know he's like one of the things he's like Steve was the most remarkably focused person I've ever come across.

And one time you know he were talking about this and he's like well how many things have you said no to? And he's

like well and Jony he's like I said no to this and I said no to that. He's like

Steve's like no no you didn't want to do that. Focus is saying no to a good idea

that. Focus is saying no to a good idea that you really want to do and because it distracts you from a great idea.

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 focus thing originate?

So there's a great line the answer is it's not one thing. I came across it in this book I read in back in 2022 it was actually the the biography of Francis Ford Coppola. Because I'm also obsessed

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.

Okay.

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 I had a two and a half hour conversation with Ed Catmull founder of Pixar yesterday.

Yep.

He's just the [snorts] same kind of artists that these animators and these storytellers and these directors is the same kind of spirit that like Steve Jobs had and Ed worked with Steve Jobs longer, I think 26 consecutive years.

Long longer consecutively with Steve Jobs than anybody else. But I would say cuz most of them are men, especially when you're going back in history. If

you're building a company 150 years ago, Totally. Most likely a dude.

Totally. Most likely a dude.

The line I read in Francis Ford Coppola's biography that put into words of a recurring pattern that I'd noticed over and over again. It 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 have 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

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

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 out his son like a [ __ ] coward, right? He's opposite. I

know you have a son, I do too. It's like

I 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 a Hollywood, there was no such thing as young directors at the time.

Yeah.

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 the guy would work 24/7, fall asleep editing the movie, like unbelievable

work ethic. Few years later, a decade

work ethic. Few years later, a decade later, he wins an Academy Award Mhm.

and he let his dad do the soundtrack or the score of the movie and his dad wins an Oscar Mhm.

for the score of the movie that his son made. It's almost like for full circle.

made. It's almost like for full circle.

It's like who's the genius now? You

wouldn't have even had this opportunity if it wasn't for me.

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?

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

I wouldn't can just consider myself normal at all. Exactly.

I don't either. I'm relatively

well-adjusted.

What does well-adjusted mean to you?

I can function in society relatively well. I can have a conversation with

well. I can have a conversation with you.

Yeah, but we're like the same kind of personality type.

I'm not so focused that I can't like pick my head up and look around.

Can you do you have the patience, like let's say if your kid 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?

I think I'm better at that than the average entrepreneur.

Okay.

[laughter] I can't I can't My co-founder could not.

Okay, exactly. So you know this personality type. No, they're obviously

personality type. No, they're obviously they're they're not normal. They're I

would not consider them well-adjusted.

It doesn't mean you have to be a prick.

This is a very important point.

Okay, I wanted to ask you that cuz a lot of the best founders of my generation were described as [ __ ] So you have to be an [ __ ] to be a good CEO?

Um no. No, definitely not. Okay.

No, absolutely not. I'm actually working on something. Daniel Ek, founder of

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.

archetypes. And for this exact reason.

Because when he started Spotify 20 years ago, everybody tried to imitate Steve Jobs.

Of course.

Founders today, who they going to imitate? Elon or Jensen?

imitate? Elon or Jensen?

Yep.

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 he's like a team player. He's a very different kind of

player. He's a very different kind of archetype. And he would try to like

archetype. And he would try to like almost like wear somebody else's clothes or wear somebody else's personality.

He's like, "This isn't working."

Yep.

And what he realizes now, you know, he he knows himself way better. Now he's in his 40s. He has two decades of

his 40s. He has two decades of experience. He knows a ton about the

experience. He knows a ton about the founders. He's like, "Oh, there are all

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 I love this.

Yeah. And if you want to help, let me know cuz I think some feedback and some insights into it. Every founder I talk about, they're like, "This we need this." Because

this." Because Daniel's point is like more important than like product market fit or even like founder industry fit. He believes

the most important is founder problem fit.

Yep.

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

fit. Steve Jobs, founder problem fit with what he was doing, perfect example.

And so hopefully what we're trying to do is like 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 as trying to to map all these different out. And then have a way for you to to

out. And then have a way for you to to identify, "Oh, this is my archetype."

And then here's maybe 10 examples of historical people that also founders that also have the same archetype. So

maybe you should go read about them and how they ran their company and how they did. And then what other archetypes

did. And then what other archetypes other founders work well together. It's

going to take a long time, but yeah, this idea I rejected completely that you have to come from a broken home or you have to be an [ __ ] or you have to be, you know, X Y and Z. I went up to Canon and and recorded a podcast with Toby

Lutke, who's very fascinating. And he

said the best way. He's like, "There's not one right way to do what you're trying to do. There's probably a hundred. You've got to figure out what's

hundred. You've got to figure out what's right for you."

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 some it's it's a superpower.

And like I 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?

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 because he has this line he says, I think it's a 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.

Yes.

Where it's like you're missing the imitation socialization gene. Now, this

is I think Peter's take on this is really good. We need to ask what it 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.

Yes.

Think about trying to talk Elon out of building SpaceX. Good luck with that.

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.

Yes. So, it's pretty common today, even the current founders.

Definitely in tech.

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?

No. No.

I don't think so. That That's the interesting thing. Maybe there's

interesting thing. Maybe there's something particular about technology.

We're in San Francisco today.

You know, people are like, you should move here. I think it's very beautiful,

move here. I think it's 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.

Mhm.

And I think a lot of this is people pretending to have autism or pretending Yeah, 100%. We naturally imitate.

Yeah, 100%. We naturally imitate.

Yes.

And even though Peter Thiel spread obviously, you know, the the issue with being memetic and that then I think increased people being memetic.

Okay. Do 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 studied the best.

have wrong? Like you studied the best.

I don't actually spend any time with VCs.

Chip on your shoulder.

Yeah.

Carnegie for Jesus.

Rockefeller.

Rockefeller. Did they all have a chip on their shoulder?

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 of the father has on the son, right? I

mean, Rockefeller's father was a bigamist. He had multiple families. He

bigamist. He had multiple families. He

was a scam artist. He would try to cheat his sons. This is in all biographies.

his sons. This is in all biographies.

And I collect obscure Rockefeller biographies. I probably have like 15 of

biographies. I probably have like 15 of them. I made my own biography. I have a

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 Rockefeller archives. I printed it and [ __ ] bound

archives. I printed it and [ __ ] bound it. That's how obsessed I am with

it. That's how obsessed I am with Rockefeller. And it's clearly that like

Rockefeller. And it's clearly that like Was he on the spectrum?

No.

Okay.

I don't think so.

But he was obsessed.

Focused.

Okay.

And and part of this Do you have a chip on your shoulder?

Yeah, for sure.

Did they all?

Trying to think of counter examples that did not. I can't think of one right now.

did not. I can't think of one right now.

I'm sure So generally, yes.

Yeah, generally, yes. I think talking absolutes, we're obviously going to find some kind of example, but yeah, generally yes.

Okay. Does

Does sort of the immigrant advantage VCs like immigrants, people who landed in this country I interviewed Khaz from OpenDoor.

Yes, who I love, by the way. It 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? Sort of a common trope amongst

on that? Sort of a common trope amongst VCs, they like the immigrant advantage.

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. They

risked their lives literally on a [ __ ] 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-mi journey to South Florida.

Yep.

What does that tell you? That had a profound impact on me. And I This is where I'm like this most most pro-American, pro-capitalist person that I know.

It's just cuz it's like, no, I know what like we have. Like I'm unabashedly pro-American, pro-capitalist. And I

pro-American, pro-capitalist. And 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

opportunity. Now I come to this country and it's unlimited opportunity." And

it's weird that the people that their families have been here for multiple generations think, "Oh, there's no opportunity. Everything's gone. This

opportunity. Everything's gone. This

This sucks." It's like, Yeah.

Okay, what did this surprise me when I looked at kind of the modern tech CEOs?

Only three of the 10 were immigrants.

Jensen was an immigrant. Elon was an immigrant from South Africa. Sergey was

an immigrant from Russia. All the more born here. That actually

born here. That actually but those three were responsible for what? Like

what? Like Oh, yeah. In in in terms of market cap.

Oh, yeah. In in in terms of market cap.

There's some other winners on the list, though.

I was surprised. I thought it was going to be eight out of the 10.

Bezos's dad was a Cuban immigrant.

Yep.

A bunch of them had Bezos is a Cuban So, three out of the 10 were immigrants.

Three out of the 10 dads were immigrants. But it certainly wasn't the

immigrants. But it certainly wasn't the the the common factor.

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 like I'm going to run this through a rubric."

It's for me like I don't even I barely invest. And my whole thing

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 to you to tell me what the company name is or what it does. I just like bet on you. Like I knew for a fact that

on you. Like I knew for a fact that there was no way I wasn't going to succeed. So, I will [ __ ] kill myself

succeed. So, I will [ __ ] kill myself before I fail.

Um and that's what I would look for. I

wouldn't look for like chip on shoulder, immigrant, anything. Like this person's

immigrant, anything. Like this person's going to figure like Ed Catmull yesterday, one of my favorite things he ever said. And keep in mind, Steve Jobs

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.

Cuz he'd he'd give these talks and he'd be like he'd ask like what's more important, ideas or people? And he's

like no one realizes the false false economy. He's like ideas come from

economy. He's like ideas come from people, therefore people are more important than ideas. And his whole thing was it's all the talented people.

So he's like if you give a great idea to a mediocre team, they'll [ __ ] it up.

Yeah.

If you give a mediocre idea to a great team, they'll either fix it or throw it out and create something new.

Yes.

So that's what I would look for. It's

like Travis Kalanick like just look into his history. That dude was going to make

his history. That dude was going to make Uber work.

Yep.

Or he was going to die trying.

Yep. Okay. You studied all these folks.

Some founders who walk through the door at Sequoia and they're solo founders, some are co-founders, some have big teams. For the most part when I look back at it, some had founders at the beginning, but generally it was the one person that drove the company. It's

always one. And that other founder sort of there could be some examples, but this is also Doesn't I I again, I don't pay attention too much to the startup scene. Doesn't Y

Combinator like heavily recommend co-founders?

I think in general the the conventional wisdom is co-founders is a very good idea. In fact, MIT did a big study and

idea. In fact, MIT did a big study and they said the optimal number of co-founders is three. I'm not sure I buy that. Anyway, you spent some time in

that. Anyway, you spent some time in Charlie Munger who was not the co-founder of Berkshire Hathaway, but sort of was.

Yeah, I What have you What have you learned about that co-founder situation? What

What about partnerships that We've studied all these folks.

So So we're at Sequoia. I think

people should read the forward to the updated version of Michael Moritz's book Return to the Little Kingdom. So it's

book he wrote before I think he even was at Sequoia.

Yeah.

From the first like six years of Apple.

Then he did this updated version like 2009 2010 called the Return to the Little Kingdom. Read the forward of that

Little Kingdom. Read the forward of that book.

Okay.

First of all, Moritz's writing [ __ ] incredible.

Great writer.

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.

Believe it or not, I never read it.

Oh my god, you need to read it today.

Read it this weekend. It's phenomenal.

Got it.

He was talking about, you know, Steve is singular. It's like when had anybody

singular. It's like when had anybody essentially refounded the way he frames it in the four, he's like, "Steve refounded Apple.

He didn't found Apple once, he founded it twice, and the second time he was alone."

alone." And then he pulled off the craziest turnaround in technology history. And so this is when I think of

history. And so this is when I think of like even they're like, "Oh, Buffett's not the founder of Berkshire Hathaway cuz he's Shut up.

And just like Munger. Munger's just

Munger's just co-founder, dude.

Carnegie, Ford, all these folks.

There wasn't many partnerships.

No, that's not true. So, Carnegie didn't even run his company. This guy named Henry Clay Frick Okay.

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.

Okay.

Frick was the operator. Carnegie was

often like sailing around the world when Frick was the one building Carnegie Steel, and he kind of forced the sale to J.P. Morgan. It's a fascinating story.

J.P. Morgan. It's a fascinating story.

Anytime there's like this new technological change and disruption, there is physical violence, and we're seeing this with the attacks for against the data centers and the founders of these AI companies.

Yes.

That is unbelievably predictable. It

reoccurs throughout history. Frick, let

me tell you about Frick.

They're going through this. It's

Industrial Revolution. There's all this change. You know, when you have strikes,

change. You know, when you have strikes, people are just go read the history.

They died about this. Frick got shot in the neck. An assassin went into his

the neck. An assassin went into his office, shot him in the neck, grazed him, right? Then they they they arrested

him, right? Then they they they arrested the guy.

Frick had it sewed up and insisted on finishing his day's work, and then went home.

[laughter] Okay.

So, Frick is a a very badass dude.

Is this an exception though? Like is the co-founders that or the partners that last an exception rather than sort of I would take him one-on-one. So, like if you want to go through the robber barons Yeah, but 400 for crying out loud.

Yeah, I know. No, but like but like okay, so like Carnegie was like made all the money. He was the largest

the money. He was the largest shareholder, but Frick was running the company. He He was smart enough to

company. He He was smart enough to acquire Frick's company and realized But like Ford?

No, Ford was an autocrat.

Okay.

And like wouldn't listen to anybody else. He would remember by 1919, he went

else. He would remember by 1919, he went to he bought out all his [ __ ] shareholders. He owned 100%

shareholders. He owned 100% Rockefeller?

of Ford Motor Company.

Rockefeller built a team of founders.

Okay.

If you look at his board, it's it's not a board, but it's like his they called them partners. All the people taking

them partners. All the people taking dividends from Standard, almost every single one was a previous founder. And

he made essentially a board or like 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 was a lot of them.

I talked to Munger about this. Like

he he was just like Buffett is a once-in-a-century talent. And he's like,

once-in-a-century talent. And he's like, "You are so arrogant."

Cuz Munger had a big ego. Like when I met him, he's he told me the funniest thing.

I'm actually surprised to hear that. I

thought he subjugated his ego His ego a lot.

He talks about this. So, he used that word subjugate. That's exactly what he

word subjugate. That's exactly what he said. But he goes, "If I could do life

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'd do a better job of hiding it."

[laughter] Okay.

But at this point he goes, "I thought, you know, 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 like

singularly focused. He wanted to like fish and boat and design architecture and do real estate and do all this other stuff. So, he's like, "What How arrogant

stuff. So, he's like, "What How arrogant would I have to be to not sub- jugate myself to a once-in-a-century talent?"

Got it.

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

One of my ah-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 in Silicon Valley.

Yeah.

There's kind of one dominant person.

Yeah, and then they go away.

That second person you yell at. Wozniak

went away. All the people that co-founded of Facebook went away.

It's pretty common.

Yeah. I This is This is my argument about this. It's like Now, maybe that

about this. It's like Now, maybe that one guy needed these other people in the beginning, but there's always just one There's a singular drive Usually a singular driving force behind the company.

Let's talk about these individuals. You

can get inside their heads. And some

people have positive self-talk. I have

negative self-talk.

Still?

Yes.

I just changed this about myself.

It It's the best ever.

Okay. I've tried. And what about these people you're interviewing? Do they have imposter syndrome? Do they have negative

imposter syndrome? Do they have negative self-talk? Do they overcome?

self-talk? Do they overcome?

The imposter syndrome is an interesting idea. Interesting question.

idea. Interesting question.

I can't think of anybody I think that has imposter syndrome right now.

You still do?

Yeah, I feel like kind of nervous right now.

Why are you nervous?

Just damn.

[laughter] So, I don't know about the imposter syndrome.

I was just in a board meeting for the last 3 hours. Little It's like, "What am I doing here?"

Oh, interesting.

Yeah.

One of the greatest piece of advice that Steve Jobs ever got he got from Nolan Bushnell. So, Nolan Bushnell was like 9

Bushnell. So, Nolan Bushnell was like 9 or 10 years older than him. He was his mentor and founder of Atari. And he told Steve, he's like, "If you pretend to be in control, everybody else will assume that you are."

[laughter] Okay.

Steve took that advice and ran with it.

So, I don't know about imposter syndrome. What was the other part of

syndrome. What was the other part of your question?

Just the negative self-talk.

Yeah. Yeah, I mean Jensen, dude.

Yeah.

Like Like he wakes up every day and he says he looks in the mirror and says, "Why do you suck so much?"

Yeah. He

It Do you think that's common?

I mean, then you think about Elon. He

says his mind is a storm. He doesn't see He seems to like embrace chaos and need like some kind of foil or some kind of problem. He seems to be like freaked out

problem. He seems to be like freaked out when things are going well.

Yes.

Uh so, I I definitely think he's got a dark mind.

I'm kind of negative inside, but that's a founder trying to project positive outside.

I think it's way more common. The best

founders, they don't like sleep on wins.

They essentially do something great.

They 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. Yeah. And his whole thing

investors in. Yeah. And his whole thing is like he's like, "We got so much more to do."

He's like, "Okay, we had a something good happen. Like, let's go out to

good happen. Like, let's go out to dinner." And by the time of the dinner,

dinner." And by the time of the dinner, before dinner's over, I'm thinking of the 17 things that are not going right.

That's why he's great. That's also

different than like being super critical and negative. And I

think for me Brad Jacobs Yeah.

who started eight separate billion-dollar companies uh he's the one built Reading his book and the building relationship with him. I don't know what happened. This has never happened in my

happened. This has never happened in my life. But just something about being

life. But just something about being around him cuz he has 45 years of experience as an entrepreneur, longer than I've been alive.

And he's a be [ __ ] ruthless with himself.

Mhm.

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 Like, that's He's like, your your source of drive, that's what 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

life's work. Your inner drive should be generative. It should be like, 'Hey, I'm

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.'"

Mhm.

And I 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."

clicked. I'm like, "I'm done with that."

And now it's just like I wake up every day, 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?"

But then that that negative self-talk is what got you to where you are today.

But but then your fuel source has to change.

Yeah.

Because it could also destroy you.

Right.

Yeah, and so it's like I Again, I know I don't want to do something for 5 years, for 10 years, for 15 years, for 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

just I'm obsessed with people that People say if 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.

Yes.

Those are the people I love.

Yes. Okay, you brought up something interesting about platform changes. The

Industrial Revolution, obviously huge platform change. Even like Henry Ford

platform change. Even like Henry Ford and the assembly line, kind of a big platform change.

Massive.

When those things happened, did the profile of the founder CEO change and did the way they ran their companies change? Cuz we're going

companies change? Cuz we're going through something and maybe bigger, maybe not, but probably bigger now.

What do you mean by the profile change?

I'll give you an example. You know, Paul Graham talked about this thing as founder mode and manager mode. Manager

mode being kind of Jack Welch military star style organizational structure, very top-down.

Founder mode being Brian Chesky, who pretty distrustful of conventional wisdom, thinner layers of management, gets right down to the coal face as much as possible. And so those are sort of the

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

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 are just giving more context to that AI system in the middle, circular shaped. They're

feeding contests, they have judgment on the outside. Over time, the AI system

the outside. Over time, the AI system makes very few of the decisions today, but maybe 5%, 10%, 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 have needed in the previous generation. Did

something like that happen to the profile or the way they built companies back in the previous It's a great question. I just asked Michael Dell this.

Mhm.

Because if you think about Dell, like he started company when he was 19 with $1,000. He's like, "Hey, I'm going to my

$1,000. He's like, "Hey, I'm going to my University of Texas dorm room and I'm going to take on the biggest company in the world, which is IBM, which is absolute batshit crazy idea, right?

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 a hundred billion dollar market cap.

It had 80% market share of the entire technology industry. I think Mark said

technology industry. I think Mark said on the podcast that's like having 10 Googles. It's just like we haven't seen

Googles. It's just like we haven't seen that level of domination ever since then. It's just a crazy thing and he

then. It's just a crazy thing and he went up succeeding and Dell was actually profitable every single quarter for the first like 20 years of its existence.

It's like it's a crazy feat. And cuz I'm always skeptical of 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

technological revolutions. I asked him that because I can't like to me it feels different. And he's like no this is this

different. And he's like no this is this is not like anything else that I've been through. I actually think the way to run

through. I actually think the way to run a company Toby Lutke believes this too.

I I do think the way to do it and how you could do it and what's available to you is completely different. Like this

time in my opinion is actually different because the amount of leverage that yeah exactly. So that that's what I

yeah exactly. So that that's what I would say.

I think the shape of the organization changes.

I think the number of people you need changes. I think the way you compensate

changes. I think the way you compensate people cuz let's say you have 100 X people now that are really proficient with these tools changes. I think the planning cycles changes cuz it's moving so fast. I actually think

so fast. I actually think it's different. Like compared to like I

it's different. Like compared to like I went through the internet like 1990s when I started my career and Google came along and that SaaS came along and mobile came along. This is a lot different.

There's a great line in the Almanac of Naval that my friend Eric Jorgenson 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 leverage. I

think this is why we talked about I think we started this conversation when me and you've had this conversation before. It's like the premium on focus.

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 who makes you know 1 X and then you can have the most talented people we've already seen some of this. They're

not 100 times more valuable. They're

like 1,000 I don't know. So I'm really close to John and Jordy of TBP and I'm obsessed with podcasters. I've built

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 them about this.

But, Jordy came into podcasting and it wasn't like he was like this 2x as good marketer as the next best podcaster. He

was like a 100x better.

And if I was open AI, I would make him the CMO of open AI. The value is like he, you know, he could produce I'm not saying he will, saying he could produce billions of 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 the show for that was seven only 17 months old. Everybody's talking about oh, all these people trying to clone them. It's like they can't clone their

them. It's like they can't clone their minds. They have no idea what was

minds. They have no idea what was coming.

Yeah.

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.

I think that I don't know about that.

One other thing that's different and 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

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

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 11 Labs, they're not that focused. They're doing

tons of stuff and they're able to do stuff fast. Bezos used to talk about

stuff fast. Bezos used to talk about these one-way doors and two-way doors.

Yeah.

Things that used to be one-way doors like we're going to do this a big initiative. We're going to go

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

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.

I don't know if I have a take on it. I

would say like I'd be very wary. Like

these people that you mentioned have built great products. It they haven't built durable businesses yet. We have to see how this plays out.

Yes, still early.

Yeah, so that's the issue I would have.

It's like yeah, maybe there's a good ideas, but like I'm interested in people that build durable businesses. I again,

I don't want to be acquired. I want to be around running my

acquired. I want to be around running my business forever. I I've spent a bunch

business forever. I I've spent a bunch of time with older founders.

I'm talking 70 A lot of time with older founders. No, but no, but I'm talking

founders. No, but no, but I'm talking about like recently like 70, 75, 80 years old. You know I realized like if

years old. You know 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 like a bunch of [ __ ] I don't know how many people can found, you know, multiple great companies

Rare. And they're like, I'm very rare.

Rare. And they're like, I'm very rare.

Yeah. Elon like

I think it's the second-time founder thing is really overrated cuz most of the successes are first-time.

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 have to wait till they're 75 years old. This happened maybe 25 years

years old. This happened maybe 25 years ago.

Asking for a friend.

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 some kind of like weird sixth sense I had about having these conversations where it's like, man, this is like so far down what you had accomplished in the past and like you're just like, oh,

I have to play the game. It's like I would just if you're out, then just you're done for the rest of your life.

Go [ __ ] on your boat or go do whatever.

not capable of being all out.

and I don't think so either. That's why

you don't sell. And so that's what I mean about be very hesitant of taking knowledge or like ideas and 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 time Give it time.

Let's see how it plays out. I don't

know.

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 [ __ ] I think taste is very real. Now, what's

what's coloring this is like I've been a big fan of Rick Rubin.

Yep.

Taste is very real. The guy's built a wonderful career. Same thing, started at

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 them? Cuz he his taste.

Yeah.

And and I realized he's like scary good at making podcasts, too.

Mhm.

And we were talking before we started recording and I go, "Dude, I've been thinking about you. Why are you so good when most people make podcasts are very, very bad?"

very bad?" And I go, I realized you took a skill very, very bad? Is this your way of telling me No. I wouldn't be here if you were.

No. I wouldn't be here if you were.

I'm kidding.

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

Yes.

Which if you think about what his main thing, I go, "You're professional listener."

listener." Okay.

And he lit up. And I started explaining my theory on why you're so good at podcasting.

Yeah.

And he goes, "Stop." He goes, "We have He stopped. We have to record this. This

He stopped. We have to record this. This

is too good." And so he agreed with that that his his essential skill set is like Not just his taste, but most people when they're talking like 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 like really

or judgment. He's just like really interested in these people. That's why

he's very selective who he works for or works with. And so yeah, he he has very

works with. And so yeah, he he has very real taste.

Is he an exception though?

Oh, of course. Like

Like did Bezos have taste? Jobs

obviously had taste.

Jobs obviously had taste.

Did Nvidia did Jensen have taste? Did

Zuckerberg have taste?

I think So we we mentioned the Broadcom guy. Hock Tan, I think is his name.

guy. Hock Tan, I think is his name.

Yes.

He was just to 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 idea this was going to happen. The opportunity was in front of

happen. The opportunity was in front of me. I made a good decision. Then I was

me. I made a good decision. Then I was like, "Oh, what can I do now that I got to that next rung?" And he like looked around and then he's like, "That was the strategy." He's like, "There's no

strategy." He's like, "There's no [ __ ] way. It's way too many moving parts. Way too complicated. I could have

parts. Way too complicated. I could have predicted it 20 years ago what was going to happen." So I don't know. I I be very

to happen." So I don't know. I I 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

attention to. So, I don't even think about it.

This is exactly what I asked 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

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 themselves or this should they get some help?

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,

communicators. I would not be yourself, buddy.

[laughter] Like I don't want to tell you yourself sucks. So, I would not be yourself.

sucks. So, I would not be yourself.

How much shaping should you take? Like

as the CEO I remember coming up and we're going public and we hired people like 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?

I think it obviously depends on the industry you're working in, who you are as a person. Everything comes down to like who you are as a person. What 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,

reading biographies. It's like, yeah, there's got a good business ideas in there. But essentially [clears throat]

there. But essentially [clears throat] 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

life. We're alive. You're listening to this, 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 [ __ ] podcast

unmanageable. I've run a [ __ ] 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. Like I'm very disagreeable

other people. Like I'm very disagreeable and like micromanaging and and everything else and might now this new podcast like ask my team. Like I am [ __ ] I can be ruthless in a nice way.

I'm not mean but like nope, we've got to redo that.

Most of these great founders are disagreeable. True or false?

disagreeable. True or false?

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

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 like ran his own money. His 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 no permanent capital structure, no fund.

You know, why do you do that? And my

friend said the funny thing, he goes, "Sam was constitutionally unsuited to manage institutional capital." Meaning

Sam was a wild band that was uncontrollable. And he would say [ __ ]

uncontrollable. And he would say [ __ ] he had no filter, and he didn't want, you know, 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 got to be. I don't want to have multiple sides

be. I don't want to have multiple sides of me. I'd rather just be like, "This is

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

interesting." Like if you think about founders, like when I go through the books, everybody's like, "How do you pick out like what you want to talk about?"

about?" Like what are you thinking about when you're reading? And I'm like,

you're reading? And I'm like, "Absolutely nothing." Like I'm reading

"Absolutely nothing." Like I'm reading and like that line sticks out to me for some reason, I underline it. And then I write jot down what comes to mind. And

then when I before I sit down to record, I just go back through 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.

at all. It's all instinct.

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.

I met my hero.

James Dyson.

Okay.

Yeah.

Let's come back to that, but any surprises in meeting these people face-to-face versus books? Is there

whitewashing in the books? Are the

people face-to-face like very different than their whitewash external presence?

I would have to imagine if you're the especially for autobiographies, you write an autobiography of your life, I write an autobiography of my life.

That's whitewashed.

Come on, man. We're going to like 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.

Of course.

And so this is the the I always get this where like, "Well, how do you know the stuff in the books is true?" You don't.

But we're not taking a his- There's no It's not a history test.

If I read an idea in the book, right? It

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. Why

did 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

true. I'm just looking for interesting ideas. It's not a history test. What I'd

ideas. It's not a history test. What I'd

say about all the people I've met is they they've been unbelievably like kind and generous and thoughtful.

Mhm.

But I also don't work for them. So who

knows and I'm not I'm not in their family. I'm not in their house. Like

family. I'm not in their house. Like

it's like a different interaction. I

don't think you think people today, the great founders, are different than the ones of 100 years ago?

No.

No.

Same same same personality type.

Same phenotype.

Yeah. Same

What else is in common?

Like kind of personality traits?

Yeah.

So obsession, high level dis- disagreeableness.

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

little disagreeable. I think it's just very natural to want to do business with the very charming person. Is that a bad instinct?

I've done like 15 episodes on on Steve Jobs and I've 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 um Steve fired two people off the Pixar

board and he fired them because they never disagree with him.

Mhm.

And he's like, if they don't disagree with me, Yeah.

what's the what value are they giving me?

Yeah. Yeah.

He wanted you to fight back and to be was disagreeable himself. Are they all disagreeable?

Rockefeller had very advanced social skills, I would say.

Okay. Did they all have advanced No. No. No. So but Rockefeller's an

No. No. No. So but Rockefeller's an interesting thing because there's people that worked for him for like 40 years that said he never heard 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

them fight. And then he said, "I believe in this. If you guys don't want to do

in this. If you guys don't want to do this, I'll put up the money myself. If

it works, Standard Oil will pay me back.

If it doesn't, I'll eat the 3 million."

And then his partners like, "Well, if you could take the the risk, we can, too." And that that's how they agreed to

too." And that that's how they agreed to do it.

That's not disagreeable. That's

something else.

Yeah. It just depends on the person. But

yeah, there are these traits that that obsession focus cost control, obsessed with having lowest cost. They see that advantage

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

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,

essays. But when that essay went viral, I'm like, "We're bringing this back."

I'm like, "This is a new thing." It's

like, "They're all This is not new at all."

all." Interesting.

At all. Nothing is new in in the world.

What is new?

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 would talk to him um you know, he he he said that he we're

going to look back on 2026 uh we're going to look back on this year in history as like the year that every single business was up for grabs.

Yep.

That you can rebuild almost every single business AI native and have a massive advantage. And

advantage. And uh I think that's an interesting thing.

When you look back at all these folks, how many of them had like great, well-balanced personal lives, great families, had like a really

deep life beyond between the lines?

I think three of them.

Out of all of them, only three?

I think uh Ed Thorp, who is a very fascinating character, created the first quantitative hedge fund, uh invented the way to to count cards for blackjack, phenomenal investor. He was the first

phenomenal investor. He was the first is only three.

Him, Sol Price. Do you know who Sol Price is?

No.

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

anybody else. Jeff Bezos took a lot of ideas for Amazon from Sol Price. Yeah.

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. Other one I

would say is Brunello Cucinelli.

Okay, but it that was his autobiography and I heard that may or may not be true.

Advice to founders. So, I spend all my days with founders trying to build trillion-dollar companies. Advice for

trillion-dollar companies. Advice for them on their lives.

I don't ever give advice.

Why not? I'm asking you for advice right now.

For you?

Let's use me as a proxy.

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 like just trying to identify what's going on in somebody else's life. Like I think it's almost like

relatively useless. I think people

relatively useless. I think people literally do what they want to do. I

talked to a lot of founders. Now, there

is this thing where they find it very useful to have like 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,

[ __ ] Rockefeller ran into that situation. This is what he did or Ford

situation. This is what he did or Ford did this or this guy did that."

to build a trillion-dollar company and have a very well-balanced life like Ed Thorp?

I don't even pay attention to public markets. I don't even understand.

markets. I don't even understand.

There's 10?

There're 12 including like the Middle Eastern oil oil guys.

Okay, so let's just take the American companies. 10.

companies. 10.

Any of those guys well-balanced? 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 Mhm.

and stayed married and most of them married their spouse was kind of an intellectually equal. They met them and

intellectually equal. They met them and they were very accomplished on their own and so they started out with an intellectually formidable [snorts]

partner very early and stuck with them.

I thought that was interesting. Of

course, like Larry Ellison's had four wives. Like

wives. Like six now.

Okay, but Yeah. Um, but he's doing some heavy

Yeah. Um, but he's doing some heavy lifting for these other guys.

But I thought it was interesting that they all got married very early to peers.

And how about through history?

And history, they're just like they're terrible husbands, like divorce, like just not I think good I would I would not consider them in many cases bad fathers too.

I see.

Is this a very difficult thing to do? I

remember I just finished reading Phil Knight's autobiography Shoe Dog for the third time.

I love that book.

And think about what he says at the very end. You know, like he had two sons, one

end. You know, like he had two sons, one of them died tragically in a drowning accident, and he was like 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's he knows he's dying. He's writing the book when he's riddled with cancer.

And he didn't regret that?

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 gets in their lives is like, oh, I have this regret. Because I think it's a

regret. Because I think it's a personality type. It's almost like a

personality type. It's almost like a compulsion. If they played out life

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,

at everything. It's like, Jeffrey, you're obviously [ __ ] 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

saying, don't do it where like you're on the phone or you're like 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. Like make it so they're it's so memorable with them. I

thought that was an interesting idea and like recommendation. But look at the

like recommendation. But look at the people like the AI research right now.

This is the game of kings.

Yeah, I I I met Demis Hassabis. He just

did a an interview on Fortune where he's just like his schedule is he has like his thinking time from like 11:00 p.m.

to 4:00 in the morning, right? Then 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 work days.

Yeah.

Okay, you studied all these people. I

spend all my time with with Sequoia founders now.

Advice to them.

How to become iconic that someone that that you would read their book and do an episode on them?

I think the the best founders like don't need advice. I'm very skeptical of this

need advice. I'm very skeptical of this narrative that like we back and discover the greatest talent. The way I would put this is like

talent. The way I would put this is like Michael Jordan said something very interesting. He was at the end of his

interesting. He was at the end of his career and Kobe Bryant's coming in.

They're like, we we discovered the you know, Michael Jordan, we discovered the next the next Michael Jordan to Kobe Bryant. And he's like, this will happen

Bryant. And he's like, this will happen again. There will be another me.

again. There will be another me.

Yep.

And he goes, first of all, you didn't discover me. I just happened to come

discover me. I just happened to come around.

Yep.

And I think the best founders are like that. Like they're not discovered. They

that. Like they're not discovered. They

make themselves known.

And I'm highly skeptical. Like these are force of nature. Again, go back to Mike Moritz, the forward that he wrote in the return to Little Kingdom. In a

paragraph, he can describe what a founder is. He's like, these are

founder is. He's like, these are irrepressible. This is the line he says

irrepressible. This is the line he says about Jobs and the best founders.

They're irrepressible forces of nature.

Mhm.

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.

Mhm.

But going around like, oh, I would, you know, paint that a little different or I would do it a different way. It's like, they've got it.

way. It's like, they've got it.

Yeah, I think you're mostly right about that. I don't proactively give advice.

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.

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,

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

books. There's a goldmine here of all this past entrepreneur knowledge. No

one's [ __ ] 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's active service is a life well lived. When I

well lived. When I get to the end of my life and he's like, don't figure it out. They

don't know what to do with it. Like I

don't over explain [ __ ] You listen to Founders. Like I don't over explain

Founders. Like I don't over explain [ __ ] It's like this guy did that.

Nope.

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.

the things that I think is interesting about you is there's actually not that many patterns. Like the whole episode

many patterns. Like the whole episode I'm kind of pushing one pattern.

I would I would say it's not formulaic.

Yeah.

There's patterns. There's no formula.

Any other patterns we haven't hit?

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

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. He very first time he met

Steve Jobs. He very first time he met Steve Jobs before Steve got kicked out of Apple the first time.

Mhm.

You know what Steve would talk about for an hour? He would just use the word

an hour? He would just use the word insanely great products over and over again.

Yeah.

It was still it was important to him when he was 19, when he was 25, it was still important to him when he when he was dying. He just was obsessed with

was dying. He just was obsessed with insanely great products.

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

matters? Or do you think they whitewash that out with me wanting an insanely great product? And

great product? And think small egos build big companies.

And therefore, this is what I actually think.

I don't think small egos build big companies.

I think all of these people have giant egos. I think some of them are just

egos. I think some of them are just better at hiding it. And I think that what 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.

Yeah.

It's a side effect.

Yeah.

Um They know that they're going to get the money.

Yeah.

I can't think of I mean, Rockefeller think they're born very motivated by money? They're they're

money? They're they're Sure. Especially if you're poor.

Sure. Especially if you're poor.

They have large egos. By the way, I looked through those 10 CEO the founders of the American companies.

In general, there's this narrative that they all grew up poor. In generally,

they were upper middle class suburban families. They all grew

families. They all grew would that surprise me.

Especially in the tech industry.

Yeah.

But Bezos was the son of a single mom like and his dad dipped out like But mostly, they were suburban upper middle class families.

Yeah. Yeah.

Like Gates Zuckerberg. Zuckerberg, yeah.

Zuckerberg. Zuckerberg, yeah.

Yeah, mostly.

Yeah.

All right, any advice for life advice for me? I'm on my second act.

for me? I'm on my second act.

I think Dana White there's like a simple genius to what Dana White runs his company that I'd really admire. He told me something

really admire. He told me something funny. He's like, I've never read a

funny. He's like, I've never read a single book on business. I've never

listened to a single podcast, which is hilarious. He said this cuz we talked a

hilarious. He said this cuz we talked a bunch after. And his thing was just like

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 who I am for exactly who I am for a long time. This is what Dana was telling me. He's like, understand deeply

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

this world. And then once you figure out those two things, you just wake up every day and and get after it.

Mhm.

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's such a thing Streaming didn't even exist.

Right? 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

over again. And you think he could have predicted back then he was going to sign an $8 billion deal?

I like that maxim.

Yeah, stay in the game long enough to get lucky. You guys are jumping around

get lucky. You guys are jumping around too much. This is what kills me about

too much. This is what kills me about these founders. They have a million

these founders. They have a million different ideas. They're like, I'm going

different ideas. They're like, I'm going to start, scale, sell. Okay, then what?

Everyone's like, well, I go, "What's the best company that that you can think of right now?" They're like, "Oh, SpaceX."

right now?" They're like, "Oh, SpaceX."

Elon founded when he was 30, 25 years ago. He didn't jump around. Like, he did

ago. He didn't jump around. Like, he did other [ __ ] but he didn't let go of that thing. All the values in the future.

thing. All the values in the future.

This is I think really important, but getting back to Dana's point, it's 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, then 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's going to look like?"

Obviously, [laughter] a lot bigger.

Yeah. I think that's hugely important.

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 here. So, you're the man. I

appreciate you. Thanks coming on the pod.

Thanks for the invite.

Thank you for being David Senra.

Appreciate you.

I hope you liked that episode. David,

he's a very interesting cat, very knowledgeable. I had um three takeaways

knowledgeable. I had um 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 it's Sequoia, we look for founders that are obsessed with a 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 a

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 aha, this is kind of depressing. It is very very difficult to have good work-life balance as a founder. Uh 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

life. This isn't great news for me. I

didn't have a great uh balanced life. I

didn't have 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 and becoming a CEO, be careful. It's a lot of work if you

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

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.

[music] 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 [music] 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

liked the episode. Uh you can follow me @bhalligan on X and we can chat about it more.

[music]