Anti-Business Billionaires: Lessons from Steve Jobs, James Dyson, and Yvon Chouinard

David Senra

They're like, "Would you be interested in selling your company?" Their response was, "Fuck you. This is a family heirloom."

Sam Parr

Okay, so what we're talking about today is... basically, I don't listen to any business podcasts other than *Founders*. It's the only business podcast I listen to. I listen to *Founders*, and I listen to MMA and true crime — that's pretty much it. I view you as my friend, but I'm also a fan of yours. You tweeted out this amazing thing; it was about the "anti-business person," the "anti-businessman billionaire." The first tenet of these anti-business billionaires is that they have high levels of disagreeableness.

David Senra

This is very important because everybody around you— I just used a reference of **Michael Dell**. Michael Dell could be on this list too. I'm reading his autobiography and I got to the part where he's taking the company private. It's so difficult what he's trying to do, and everybody's like, "Why don't you just give up, Michael? You're already rich. You can start another company." He's like, "I don't want to start another company. I want this. This is my first and last company." In his case, that's very rare: to have your first company be your last company. He then has a line where he goes, "I'm gonna care about this company after I'm dead." I was like, "Oh—that's a different level." So the *disagreeableness*—we use the three people in the clip, which are **Steve Jobs**, **James Dyson**, and **Yvon Chouinard**—is that they are hell-bent on making the world bend to them. They don't bend to the world. They refuse to compromise on product quality even when it seems absurd. And like James Dyson—I've got to tell you a crazy story about James Dyson—because now everybody's like, "Oh, Dyson, the guy with the hand dryer in bathrooms and the cyclonic vacuum cleaner." No—the guy has built one of the most successful companies of all time.

Sam Parr

I think it's one of the largest privately owned companies in the world.

David Senra

You wanna hear something crazy? There are always rumors, right. And, again, he's privately held so he doesn't have to disclose anything. Everybody's like, "Oh yeah, he's probably worth like $10 or $20 billion." I was like, "You're off by a lot." A friend of mine happens to know somebody who works for him, and usually you can find hints if you look at their family office. My friend knows somebody at the family office and they're like, "Man, we have a big problem — we have to deploy like $4 to $5 billion every year." So you look and he's like, **James Dyson** now is the largest producer of green peas in Europe. He owns the most sheep in the entire world. You see all these crazy things. Where's the $4 or $5 billion coming from? The rumor is that he's been taking out, you know, $4, $5, $6, $7 billion a year in dividends, retaining the enterprise value obviously because he never sold the company and still has 100% of it. I was just at this super fancy, private, investor-only conference. There were only a handful of people there. One guy controls a shit-ton of capital and he listens to the podcast. We were talking and he has a problem: the more assets under management you have — Buffett talks about this over and over again — to move the needle the opportunity has to be just so large. They were buying smaller family companies, maybe in the $1 billion to $2 billion range, and now he's like, "I have too many assets under management. I have to swing bigger." So they went to approach **Dyson**. I'm gonna paraphrase the response back from Dyson — this'll answer your question about high levels of disagreeableness. They asked, "Would you be interested in selling your company?" His response was, "Fuck you. This is a family heirloom." He's not doing it for money. He's run out of the money he will ever spend. He's doing it because he loves it. If your kids want to work in the business — you see that a lot — they're doing it because they want to pass it on to the next generation. They want to die still owning this thing. You can't go to him and say, "I'll give you $2 trillion" — it doesn't matter. There's no amount of money that you could give **James Dyson** to stop working on Dyson. It's just like there would have been no amount of money you could have given **Steve Jobs** to stop. Imagine going to Steve Jobs and saying, "Hey, this iPhone you created — the most successful consumer product of all time — how much would I have to pay you to not do this?" There's no number you could spit out that he'd be like, "Okay, yeah, I'll retire." He'd say, "This is what I like to do."

Sam Parr

*"Who's the most disagreeable person you've ever studied?"*

David Senra

Oh, that's a good question. I mean, **James Dyson's** gotta be up there. If you see the bookshelf that's behind me, it's in order by episode number, starting in the upper left-hand, so it goes all the way down. So I'm going to hit, like, 400 biographies, reads of history of [unclear: "gets and spirits"] this year, and my **number one recommendation** is still his first autobiography. He wrote an autobiography when he was 45, and he wrote another autobiography when he was 75. They're both great, but the first one's really great. The reason I recommend that one is because it's all struggle — 90% of the book is just him failing over and over and over again and him refusing to give up.

Sam Parr

"And what's he **obsessed** with? Obsessing over **vacuums** is strange."

David Senra

So, he would describe himself as an **inventor** and an engineer—definitely as an inventor. What I would say is that he's obsessed with making the world bend to what he wants to happen. If you look at his early career, he was inventing a bunch of successful products that were then taken from him because he didn't keep control of the companies. There are all these little things that happened to him that caused a lot of emotional pain, and he then fixes those problems in the new company. For him, it's like he spent 14 years before he had the idea. He's kind of similar to Steve Jobs and Yvon Chouinard—they're offended by the mediocrity of most things around us. They always ask, "Why does every product we use suck?" and they repeat that over and over. His idea came from a simple irritation. He said, "I bought a vacuum cleaner from Hoover; it gets clogged after the first time I use it because it has a bag. This is stupid—why do all vacuum cleaners have bags?" From that thought came 14 years and 5,127 prototypes, until he had the world's first cyclonic vacuum up to his incredibly difficult standards — that he owns a 100% of </FormattedResponse>

Sam Parr

When does having that trait of high *disagreeableness* go too far?

David Senra

Well, that's a good question. I don't know.

Sam Parr

Does his family love him? Do they—does he have a good relationship with his children? Yeah, because, like, Steve Jobs did not [have a good relationship with his children]. And so: can you be *highly disagreeable* and still be loved by your children? Can you be *highly disagreeable* and still be proud of how you treat one another?

David Senra

So, there is a devastating line in Steve Jobs' biography by Walter Isaacson. Walter was collaborating with him as Steve was dying, and Steve told Walter one of the reasons he wanted to do this biography: he wanted his kids to know the kind of person he was and what was important to him. "He sacrificed so much of his time at Apple that he wanted his kids to know the kind of person he was and what was important to him." That's a devastating line. Dyson, from what I understand, has great relationships. He's still married to the same wife and has great relationships with his kids; some of them work inside the company, some don't. As you know, because you listen to the podcast, I spent a lot of time talking about their childhoods and their relationship with their father. Dyson's dad passed away when Dyson was about nine. Dyson said — writing a biography when he's 75 — that he still cries and gets sad that he didn't get to know his dad as an adult. His dad didn't get to see him grow up, see his success, or meet his grandchildren. I think having that experience — wanting to make sure my kids don't have that massive hole that I had in my life — is a powerful motivation. Not that he followed his own father; his dad died of cancer when he was young, so I don't think those things are mutually exclusive. You definitely see a lot of these highly disagreeable people. James Cameron is, to me, probably the best podcast I've ever done in terms of craft, and I'm really proud of that episode. I did it two or three years ago. I start the episode by hinting at the highly disagreeable personality and reading from a GQ article: > "James Cameron has moved to New Zealand with his fifth wife." The fact that someone has a fifth wife — well, that should tell you, between the lines, that he's a difficult person to deal with.

Sam Parr

Alright. A few episodes ago I talked about something and I got thousands of messages asking me to go deeper and to explain — and that's what I'm about to do. I told you guys how I use **ChatGPT** as a "life coach" or a "thought partner." What I did was upload all types of information: my personal finances, my net worth, my goals, different books that I like, and issues going on in my personal life and businesses. I uploaded so much information. The output is that I have this GPT that I can ask questions about issues I'm having in my life, like, "How should I respond to this email?" or "What's the right decision knowing my goals for the future?" Things like that. I worked with **HubSpot** to put together a step-by-step process showing the audience the software that I used to make this. **ChatGPT** asked me all this stuff, so it's super easy for you to use. Like I said, I use this 10 to 20 times a day — it's literally changed my life. If you want that, it's free. There's a link below. Just click it, enter your email, and we will send you everything you need to know to set this up in just about twenty minutes. I'll show you how I use it again 10 to 20 times a day. Alright, so check it out — the link is below in the description. Back to the episode. Alright, number two: they have extreme self-confidence, and they do what works for them. So what's an example of that?

David Senra

So that line — that they *do what works for them*. There's this guy named **Tim Grover**, who was the trainer of both **Michael Jordan** and **Kobe Bryant**, and he wrote a book all about comparing and contrasting them. It was really fascinating. He says what they had in common was that they "do what works for them regardless of what other people [think]" — they were indifferent. There's another great line in that book that I think a lot of people you and I are going to talk about have in common: "Everyone wanted to be like Mike. Mike didn't want to be like anybody else." In situations like that — which is, I would say, common — there's this line in **Dyson's** book where he calls his method of invention and company building the *Edisonian Principle of Design*. He is not a big "I have a master plan" guy. He's like, "I'm going to just do an experiment, get immediate feedback, and do a constant set of iterations." There's this great book that I've read three times. I think every single entrepreneur on the planet should read it. It's called *Creative Selection*. It is written by **Ken Kocienda**. He was a programmer who demoed to **Jobs**, and in that book, in the most detail, he explains how he programmed the initial **Safari** browser and then created the keyboard for the first **iPhone**. What he shows in there is that all the great products that came out of Apple were just a series of iterative demos to Steve, with Steve applying his personal taste. This is why, when you talk to a lot of investors — and to me, when I talk to them — they think about business way too academically, as if you could sit at a whiteboard and plan and master-plan everything out. I don't see that in the books I read. It's a series of small decisions every day, getting a bunch of feedback, and then essentially changing course slightly every single day, and doing that over a long period.

David Senra

Over time, and by *constantly improving*, you get to amazing products and amazing businesses.

Sam Parr

Are the people who have extreme self-confidence self-confident at a young age, or did something happen? I guess: *born versus becoming*?

David Senra

All three of those. So if we're talking about Yvonne Chanard, Steve Jobs, James Tyson — they were excessively self-confident at a young age. I think part of this has to do — and I'm speaking from my own personal experience — that you grow up almost seeking revenge for the circumstances in which you were born. You know, Steve Jobs was adopted; Yvonne Chanard's family didn't have any money; James Tyson doesn't have a dad. Everybody around you is like, "Oh, you're not good enough," and you're like, "No — I'm pretty sure I'm better than you, and I will show you." You're willing to work and make sure to prove what you believe. I always say, *"belief comes before ability."* I see this over and over again. People say, "You shouldn't be confident; you should generate evidence first." No — you have that completely backwards. They believe that they can do great things way before there's any proof in the physical world. Let me give you an example: in the Michael Dell book, he hits the Fortune 500 when he's like 26 years old.

Sam Parr

And basically, for the listener, **Michael Dell**—I believe at the age of 16, 17, 18, in college, in a college dorm—he was selling computer parts to help people assemble computers, right?

David Senra

He started Dell — the prehistory of Dell really happened when he was about 16 or 17. He officially started it as a freshman in his dorm at the *University of Texas.* The *Fortune 500* thing is important because he asks, "Could the kid who grew up reading Fortune magazine possibly predict that I'd start a company that broke into the Fortune 500?" He says, "Yeah, I always thought big." He doesn't try to hide it: "Yeah, I had a lot of confidence. I knew I could do this. I believed I could do this." Now, did he think he'd hit it at 26? Probably not, but he got there even faster. He had the belief first and then he demonstrated the ability.

Sam Parr

"You also say that the **third principle** is they're obsessed with **product quality**. I hear people say this a lot, but because I've never had a job, I've never been able to intern or apprentice at one of these folks who are obsessed with product. I've never been able to see firsthand what they're like on a day-to-day basis. Can you give me an example of what they do each day in order to actually be *product-obsessed*?"

David Senra

You know, I love that you frame that question like that: **"What do they do each day?"** I was thinking about this this morning — about the conversation we're going to have today — and I think what all the entrepreneurs I admire have in common is that how they *want* to spend their time is working on their company. I get invited to a lot of things. I say no to most of them because everything that's not working on the podcast is a giant distraction. Tim Cook said this after Steve Jobs died: > "If you took an inventory of how Steve spent his time, he was at Apple, and then when he was at Apple he was at home with his family. He wasn't going to conferences. He wasn't trying to be on the scene." Yvon Chouinard — what is he doing? He's working on product and he's testing the product. James Dyson, 75 — the guy's probably worth $100 billion, if we're being honest — and where's he at? He's on the front, literally the factory floor, and then he's with the design team. The important thing — and you see this — is this is the problem with modern-day entrepreneurship: people like everything except the actual work their company does. If you can find love *in the activity itself*, you're able to do it for a long time. I have to tell this one: the main thing. I had lunch with Sam Zell — we could talk about him too — and that two-hour lunch changed my life. His main advice to me was: **"Never relinquish the freedom on what you work on."** He explained it like this: > "The more successful you become, people are going to try to constantly dangle opportunities that are distractions in front of you. They're going to do that for two reasons: they're going to try to offer you more money and more status." He said something that was brilliant. He said, **"Go for freedom. If you have freedom, you can control what you work on. If you control what you work on, you can choose to work on what you love. If you love it, you'll do it all the time. If you do it all the time, you'll get good at it, and money will come as a result of that."** All of the people I admire — they're not trying to go out fundraising all the time, they're not trying to party all the time. They're literally obsessed with what they're doing. If you take an inventory of their time, it's just spent on the company. Let me give you my example. You know this because you have a podcast: we can log in to our podcast host [podcast hosting dashboard] right now and change the name of a show. You could change the name of My First Million to Sam's Club, whatever you want. I could change Founders to whatever I want. The thing you cannot change is the RSS — the URL slug that, the first time you set up your RSS feed, you set the URL slug with the first name of your podcast. My podcast went through multiple names. The first one was *autotelic*. The definition of *autotelic* is an activity done for the sake of itself. I was telling you right from the rip: I don't care if no one listens — I'm going to do this. It's inside of me and I have to get it out. I'm going to do this. I'd be reading these books and talking about history and entrepreneurship and founders and crazy, psychotic people because that's what I love to do. I'd be doing it if no one listened.

Sam Parr

**I love hearing you talk about this.** Do you think that you've gotten crazier and more obsessed reading about these people?

David Senra

For sure, for sure. First of all — you know this because we've talked about podcasting a bunch — a lot of people try to part-time it. I think, literally, *podcasting is a miracle*: the idea that anything you want to learn... right? I mean, you grew up similarly. We didn't have money. We didn't — I don't think you went to an Ivy League school. I couldn't go to an Ivy League school at all, right?

Sam Parr

My wife went to an Ivy League school. When I met her, she told me—at first she said she went to Penn. I was like, "Is that where that football rapist coach guy goes?" She said, "No. It's a big school — a big shot. We're part of the Ivy League." I was like, "What the fuck is the Ivy League? Is that Hogwarts? I don't know what that means."

David Senra

Dude, I have a rather embarrassing story. First of all, not only did my parents never graduate college, they never graduated high school. The entire time I was growing up they never mentioned the word *college* to me even once. I remember being in high school and they asked, "What college are you applying to?" I was like, "What— the one I can drive to?" because I had to work full time during the day. I couldn't fathom what they were talking about. I moved into student housing and my roommate was from Colorado. That was the first time I ever realized — and this is really embarrassing — that some people didn’t work while they went to school. He just went to classes. He had nothing else. I couldn't even imagine that. The reason I'm so obsessed with **podcasting** and everything else is: you can learn any subject you want from someone who has usually spent five, ten, or more years studying it, and you can learn from them for free, on demand, anytime you want. How could you not be absolutely obsessed with that? Here’s the story about why I started reading more. I didn't even understand it at first, but a friend of mine told me. He visited me in Miami about two years ago and said, "It's pretty obvious what you're doing." I asked, "What?" He said, "You didn't have any mentors or any good examples, so, since you're—like—kinda psychopathically obsessed, you just started reading and trying to find good examples for yourself." There’s a line in a profile I read about a guy named **Larry Gagosian**, who built a multi‑billion dollar art business that he controls 100%. The profile said he "got so good at selling art to the masters of the universe that he became one." He literally started out selling art in a parking lot and got so successful that he's now a peer. The reason I'm doing this is that I'm trying to build the best product for the best people in the world. I take a lot of the ideas from the podcast and apply them to my own business — which, incidentally, is the podcast where I derive the insights to begin with.

Sam Parr

**The next one is *retention of total control*.** What are the trade-offs of owning everything and being maniacal about the details versus **delegation**? For example, my favorite business author, Felix Dennis, who wrote the book "How to Get Rich," isn't nearly as serious as some other guys. He's kind of like a Mick Jagger–Richard Branson combination: a rock-and-roll partier, but he became a billionaire. He says that delegation is the reason he's anything. He's like, "I'm a master delegator," which I imagine a Richard Branson type of person would also say. Whereas you have Elon Musk, or maybe Coco Chanel, or a couple of other folks who are good examples of being in total control and maniacal about the details. I think Estée Lauder — I believe she was pretty nutty. What are the pros and cons and trade-offs, and which do you prefer?

David Senra

I love that you asked this question, because this is the great thing about **entrepreneurship**: you get to *decide what's best for you*. There is not one way; there's not one right way. I could give you examples of people I covered who delegated everything, and people who delegated nothing. I just did Todd Graves. Have you ever eaten a rice and cain juice? You used to live in Austin. You're a fellow fat boy.

Sam Parr

Well, I was formerly fat.

David Senra

Yeah, yeah.

Sam Parr

But I saw him talk — I think it was Theo Von or something like that — and I was like, "Wow, you're amazing." So I went to Raising Cane's and started eating it just because he was *maniacal*. You don't think of a fast-food restaurant as being focused on the product, but there's a need for that, for sure. He was like, "We only do these types of fries. We only do chicken." It's the simplest thing, and I'm like, "How hard could this possibly be? That you need 30 years to master this? Let's go figure it out."

David Senra

So, I just did an episode on him, which I think is going to be **one of the most popular episodes ever**. When people would ask me, "You study dead entrepreneurs—what about the living ones that you like?" I bring up Todd Graves and say, "the chicken-finger guy." People are like, "No."

Sam Parr

"No, he's got a really relatable demeanor."

David Senra

Yeah—you want to hang out with him, but even if he was a jerk, the way he built his business is incredible. He owns over 90% of a business worth at least $10 billion. It's growing 30% year over year, and he's been doing the same thing for thirty years. I'm obsessed with simplicity. I just love everything about him. The funny thing is, in one interview I found with him, he literally says people told him when he was younger, "You're a micromanager. You have to delegate. You can't possibly do the stuff you're doing now." He has a great line: "Delegate—what kind of word is that? That doesn't even make sense to me." And he says the experts who gave him that advice, "I'm bigger than they are now." He's literally giving this interview when they interrupt it because they had some event, and his social media team was showing him the reel—the video reel that was about to come out. This guy is running a business with 50,000 employees and 800 stores—an unbelievable amount of responsibility—and he's like, "It doesn't go out until I approve it." He's approving every single—Steve Jobs did the exact same thing. He wouldn't let Apple stuff go out without approving it. There's another thing: every single new location—I approve every single new location. You mentioned Elon Musk. In the early days of SpaceX, Elon personally interviewed the first 3,000 employees of SpaceX. Sam Walton, go back even further: he approved—he picked out, I think, the first few thousand Walmarts. So a lot of them, I would consider micromanagers. There are some who delegate widely, too. What's more important than the label is that it depends on your personality type. For me, I am a complete micromanager. I'm one of the only podcasters still editing my own podcast. Every other podcaster tells me, "You're a fucking idiot, why are you doing that?" But I'm completely obsessed with it. I hate it, but I love it at the same time. It's the part about podcasting I like the least, but it's so important for me to completely control the final product. So again, I don't think there's one right way. You have to think about: do you want to run your business?

Sam Parr

Another thing that you said was that they refused to make **me‑too** products. Is there a story that you have where standing out by having a **different product** was key to them winning—or where it nearly ruined them?

David Senra

Let's—I don't know about anybody who ruined them. Let's use the pre-history of **Patagonia**, right, which is worth a couple billion dollars as a privately held company. And, as you know—because it's in the book and the episode—he wasn't really interested in starting a business. He was kind of like a communist; he didn't even want to start a business. He calls himself a *"dirtbag."* He was like, "I was a dirtbag climber. I lived in a van. I traveled around just trying to climb mountains," you know.

Sam Parr

Which, by the way, is a *dichotomy*. If you're a communist, why do you fully own your company instead of giving out equity?

David Senra

Because he's obsessed with control — it's almost like a paradox. The obsession ties back to control. Sometimes you can maintain control even in a public company. Mark Zuckerberg has complete control of Facebook. Steve Jobs had complete control of Apple. Other founders keep companies private: James Dyson, Michael Bloomberg, Patagonia — they retained more control because the companies are private. His whole thing was that his life literally hung on these clips that people use for mountain climbing. He thought, "These clips are plastic; they suck, they break. This is not good." They would optimize for cost because most dirtbag climbers send no money, so the clips cost about $0.75 each. What did he do? When you ask him his profession, he said, "I'm a blacksmith," because that was his trade, his craft. He thought, "I could do a better job than this." He started using higher-end steel and began selling what used to cost $0.75 for about $4 — more than four times what the market was used to paying. He wound up seizing about 80–90% market share because his product was so much better. So, founders aren't starting companies just to start companies. They're starting companies to make products. Therefore, they won't make a product if somebody else is already doing it well. No one made the products that Steve Jobs made. No one made the products that James Dyson made. No one made the products that Yvon Chouinard made. I talk to founders all the time, and even podcasters. I'm like, "Why aren't podcasters thinking more about differentiation?" When I started my podcast in February, I thought it was too late — I was like, "Oh my God, I missed the boat." But then I looked around and saw everyone doing the same thing: two people, one interviewing another. This is why "My First Million" first came on my radar. When I came on your podcast two years ago, I mentioned I listened to over a hundred hours of it because it was truly differentiated. It's two guys with great chemistry; they're funny; they're both entrepreneurs. Sometimes they'll just shoot the shit and talk about ideas and brainstorm. Sometimes they'll bring people in. It was a very unique format. Since then, a bunch of people have tried to copy it, and none of them achieve the same success because they're not the originators. They're copiers — not the ones who actually came up with the format and the idea. One thing I would say is: if the product already exists, only make it if you see a giant hole and a way to make it better. In the case of James Dyson, everyone had vacuum cleaners, but they were all crappy compared to his. Listen: you can go on Amazon right now and buy a vacuum cleaner for $40. I have a Dyson; it was $600. It's literally the best.

Sam Parr

Do you think there's a common theme among—so, most of the people you've named, and maybe most of the people you cover on *Founders*, are creating **higher-end products** where the margins are probably a bit higher? For example, I have a $600 Dyson. Yep. Patagonia now is more mid-tier, maybe, but you've covered a lot of, you know, luxury brands. I think a lot of LVMH-like luxury brands tend to be the biggest and best businesses, it appears. Is there a commonality of *being different* and thus being able to charge more and profit more?

David Senra

I don't like the "one person" idea. If you ask my own personal Mount Rushmore of great entrepreneurs, they actually had different margin profiles. Some of them obviously have big margins—like **Apple**. But then think of **Sam Walton**. Sam Walton had the tiniest margins. Why? Because his idea was, "I'm going to be totally committed to this one simple idea," which is *everyday low price*. So the margins are small. **Raising Cain** is one of my favorite entrepreneurs; his margins were like less than 10%. So yeah, I think these ideas can work for either. It really just depends on the industry and the business. But you see them appear over and over again—whether it's a high-margin business or a low-margin business, whether it's physical goods, luxury goods, or software. It's the same personality type over and over again.

Sam Parr

I'm gonna combine the last two, which is this: the first of the two was "they wouldn't sell at any price," and the second one is "their exit strategy is death," which I love — I absolutely love it. Is this particularly true with **AI**? I don't know if you've seen it. I know you're not into it because you're so focused — I think you've said you don't pay attention to the news or social media too much. There's this thing called *Vibe* or "vibe coding." Have you seen Vibe? "I've seen that." "Yes." So it's like young kids — some of whom we've had on [the show] — who in a matter of six months can go from $0 to $1,000,000 a month in revenue because it's so fast and easy to make apps. Do you think people today are thinking shorter-term than before, or has there always been a gap, with very few people willing to think long-term versus short-term?

David Senra

I think both. Yeah—undoubtedly a larger percentage of humanity is thinking short term, and we've always, as a species, been wired to be short term. Jeff Bezos has a great idea about why he would be constantly willing to have a longer-term view. His point was that if you're planning on a year—if you're investing in a product that may not reap any benefits over a year—you have a lot of competition. Five years: less competition. Ten years: no competition. Just nobody is thinking that long term. If we have a **long-term orientation**, then I want to do that because, by default and by sheer numbers, I have fewer competitors. I need to back up: I am only interested in people who do things for the long term. I'm interested in your **last business**. I am not interested in your startup, your first business. In many cases, what I'm interested in is: what is the thing that is going to be the last? The reason I've become so close with the founders of Ramp is because we have this deep partnership. One of the things I love is I talk to Karim—I'm actually seeing him tonight—who's the co-founder and CTO of Ramp, one of the most brilliant technical minds I know. Way before we became friends and partners, he was like, "Ramp's my last business. This is it." He said he has 98–99% of his net worth in it, he spends all his days on it, and he's not thinking about anything else. That's what I'm very interested in. In many cases, to get to that last business you usually have to start, have already started and sold a company—you usually have to go through a ton. It's very rare for the Mark Zuckerbergs, the Michael Dells, even Steve Jobs—for your first company to also be your last company.

Sam Parr

Which is what I had, I think. I did it because I saw a theme: a lot of the people I had admired had a "hit" in their twenties or thirties that allowed them to think longer-term.

David Senra

That is key, right? One: I think it's a mistake if you ever sell your best idea, whether you have money or not. So, **never sell your best idea**. But in the case you're describing, it's like—if you can relieve financial pressure, meaning you grew up with financial pressure.

Sam Parr

It... and it feels... and it's *real*...

David Senra

It... it destroys you. You can't.

Sam Parr

There are people who can overcome and just go all in at a young age. In general, it seems it's easier when you have a *wealthy parent* or when you have some type of support—when you *don't need to worry about rent for 3 or 4 years*. It is easier that way.

David Senra

So, to get to that point where you’re like, “Hey, I’m not going to have to worry about feeding and taking care of my wife, my kids, feeding myself,” you give yourself room to breathe. Then you’re able to step back and be like: a lot of this is just **self-exploration**. Dude, I know myself so much better now than I did... think about when you’re supposed to be picking your career in high school because then you’ve got to figure out what you’re going to major in. It’s the stupidest thing ever. If you’re the same person you were at 18, that’s very bizarre. Part of picking a successful company or a successful career you can do for a long time is that you have to go through this exploration of who you are as a person and what your true interests are. The problem with humans is we see something like “vibe coding” and think it’s really cool because these kids are making money. But eventually, through all these experiments, they might discover what they actually, truly want to dedicate their lives to. So I think it’s an overall good thing. If you’re an entrepreneur, a podcaster, a writer, an athlete—whatever the case is—you have a massive advantage if you can adopt a **long-term perspective** that other people don’t have. This is important: when I’m able to choose what I work on, I’m not worried about my downloads today or my audience size today. It’s just, as long as I do this forever and keep focusing on adding value to other people’s lives—because money comes naturally when you serve—then I’ll be fine. If I wake up every day, read a biography or the history of the greatest entrepreneurs, and sit down once a week to talk about what I learned, and do that forever, I’ll let the score take care of itself. The chips will fall where they fall.

Sam Parr

Like, I don't want the listener to think **"long-term"** means it's okay if I don't kick ass today. A lot of people will justify this and say, "Well, it's a marathon, not a sprint." To them I say, "Yeah, but have you ever run 100 meters at the world-record marathon pace? It's going to feel like a sprint to you." You have to be able to run fast for a long time. What I mean by that is this doesn't excuse day-to-day lack of urgency. You still need to be **impatient** on a daily level but **patient** on an annual level. Additionally, can you tell me—about the people who thought long-term—were they still (maybe you can give me examples) broke five or ten years into starting their company, or did they lack traction? Or did they have traction? Am I wrong?

David Senra

So, to close the loop on what you just said: I agree completely. If you think about it, there aren't many entrepreneurs with a longer-term perspective than Jeff Bezos. His line about this was: "Have long-term [thinking], but we're going to take it step by step, ferociously." His motto: *step by step, ferociously.* Not *"we're going to lollygag."* It's more like, "No, no, no — I'm fine being the company we want ten to fifteen years from now, but every day for the next ten to fifteen years we're pushing the pace and doing as much as we can." There are people who were broke five or ten years in. James Dyson, for sure. He was literally going to sleep covered in dirt because he was trying to build a vacuum cleaner — going, going, going, crying himself to sleep while his kids were small, and then his kids were completely grown up. He was in massive amounts of debt and couldn't find anyone [to help]. The reason he owns 100% of his company is because no one would actually want the equity, which is hilarious considering how valuable it is now. He even had second loans out on his home — a second mortgage — and he was crying himself to sleep.

Sam Parr

So, he was—he was nearly bankrupt.

David Senra

It sounds like he was—oh yeah. If it's not the full 14 years, it was a good chunk, because then he started licensing it. He had some small wins where he could actually pay his bills, but he was not, like, a wealthy man. **Steve Jobs** was rich from the get-go, you know. He built the first Apple in his garage; four years later he's worth $100 million and the company's public. It was pretty crazy. **Von Chouinard** was broke for an excessively long time. There's not a single pattern—it's case by case. **Jeff Bezos** was already wealthy. He worked for a hedge fund in New York called **D. E. Shaw**, and he quit that and gave up a huge bonus to move to Seattle. But he was already able to live in Manhattan. He was working for a billionaire—**Sam Walton**. Now here's another... and by

Sam Parr

The way I think, Amazon had about $100 million in sales four years in—or something.

David Senra

Super fast, super fast. He was like, "By the time he was 30..." So he starts the company at 30. I think by 35 he's a billionaire. </FormattedResponse>

Sam Parr

I tracked him on this when I had a sheet where I tracked probably 300 people. I had timelines for each of them: when they were born; when they started the thing that allowed them to be a little bit financially free; when that ended; and then when they started the thing that made them huge. He started Amazon at 32. Between the ages of about 24 — whenever he graduated college — and 32, presumably he was making some amount of money, the equivalent of **$250,000 to $500,000 a year** today.

David Senra

For sure. Sam Walton — his first... This is an interesting thing because there is an idea, a principle I've noticed: *"go slow now so you can go faster later."* What I mean by that is, Sam Walton — greatest retailer of all time, undoubtedly — had one store for five years. He was obsessively learning everything he possibly could about retail, doing all these experiments. So then you fast forward — one store for five years — and then you fast forward, let's say, twenty-five years into his career. He has the idea; he's already at Walmart, but he's like... he meets his getting sold price [unclear]. I've done episodes of "how many years"...

Sam Parr

"Did you say 25?"

David Senra

Let's say 25 years into his career. In the first five years it's one store. Twenty-five years in — let's say around there — he has Walmart, but then he has this idea for Sam's Club, which he got from other people. He took it from this guy named **Sol Price**, who came up with the *warehouse-club* idea [founder of Price Club]. The founder of Costco was Sol Price's mentee: **Jim Sinegal** was about 18, working for Sol Price; that's where he got the idea for Costco. **Sam Walton** sees that and thinks, "This is a great idea — I'm going to do it immediately." So 25 years into his career, he didn't have to stick with one store for five years. When he launched Sam's Club, within the first five years he reached about 105 stores and around $7 billion in revenue. When he started out he could only master one tiny store in Arkansas, but your skill set, your resources, and everything compounds. That's what **Todd Graves** talks about. By the time he's ten to twelve years into his career — the Raising Cane's guy — he has 28 stores. That sounds like a lot, right? He opens between 100 and 150 stores a year now. **Go slow at the beginning to go faster later.** He's learning and he's going to apply that. This is the important thing about not jumping from business to business: if you jump from business to business, all you're doing is interrupting compounding.

Sam Parr

Was it clear, for a lot of these — you know, the world's greatest entrepreneurs — that their **TAM** [total addressable market] was big enough to achieve their ambitions?</FormattedResponse>

David Senra

No, *absolutely not*.

Sam Parr

No, like, for example, you'd be like, "Look, this *chicken finger thing* — that's maybe silly. But I guess *McDonald's* is... I guess you could be kind of like McDonald's."

David Senra

I think if he did think of anything, he thought of In-N-Out. In-N-Out was founded in 1948. If you look at In-N-Out's menu, it looks like Todd Graves'. There are other people before him, but to me Todd Graves is just Harry Snyder reincarnated — Snyder was the founder of In-N-Out. Instead of doing burgers, he does chicken fingers. I just went over this because I'm going through the Michael Dell episode right now. There's no way you could have predicted the financial success or how big the market would get — most people hadn't even seen a computer, and Dell was completely obsessed with it. He started Dell with $1,000, no venture capital. His main competitor was Compaq, which started with about $25,000,000 in venture capital. Michael Dell is super competitive but nice. The book is called *Play Nice But Win*. He's constantly contrasting: "I started with $1,000; they started with $25,000,000 — I'm kicking their ass." It's really funny. Dell would tell you that the constraint of limited capital was actually good at the beginning because it forced him to innovate in ways you wouldn't if you had money. I pulled my highlights from Sam Walton. He says the same thing. Kmart existed before Walmart and was dominating the big cities. If you're going to start retail, where are you going to go? Chicago, New York, those other places. He thought, "I can't go there — I don't have any money," so he started going to little towns in rural Arkansas. What he learned was that *constraints are your friend*. If they had been better capitalized, they would never have gone into these tiny communities. What he discovered was that in these small towns there was far more business than they could have predicted. That's a perfect example for your question.

Sam Parr

"You're the man, David. I appreciate you doing this. I could just... I think the listeners will notice this is probably the podcast that I've spoken the least on of all 700. I've listened to hundreds of your episodes — I think you're at, like, 400 — and I think I've listened to half of them now."

David Senra

I appreciate that.

Sam Parr

**I appreciate you.** That's it. That's the pod.