EPISODE
698

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

Apr 17, 2025·42:00·Sam & Shaan·with David Senra·Listen·AppleSpotify
0:0021:0042:00
12 moments · 73 paragraphs · synced to the second

They're like, would you be interested in selling your company? The response was, fuck you. This is a family heirloom.

CLIP

I feel like I could rule the world. I know I could be what I want to. I put my all in it like no days off. On the road, let's travel, never looking back.

SAM

Okay, so what we're talking about today is, yeah, 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 That's pretty much it. And so, like, I view you as my friend, but I also am a fan of yours. And you tweeted out this amazing thing. It was about the anti-business person, the anti-businessman billionaire. So the first tenet of these anti-business billionaires is they have high levels of disagreeableness.

This is very important because everybody around you— I just use the reference of Michael Dell. Michael Dell could be on this list too. I'm reading his autobiography, like I said earlier, and I got to the point where they're like, he's taking the company private., and they're just, it's so difficult what he's trying to do. And everybody's just like, why don't you just give up, Michael? You're already rich. You could 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, like, that's very rare to have your first company be your last company. This is my last company. But then he has a line. He goes, I'm going to care about this company after I'm dead. And I was like, oh, that's a different level. So the disagreeableness, like if we use the 3 people within the clip, which is like Steve Jobs, James Dyson, and Yvon Chouinard, it's just like, They are hell-bent on making the world— they don't bend to the world, right? They make the world bend to them. And they refuse to compromise on the product quality, even when it seems absurd. And like James Dyson, I gotta tell you a crazy story about James Dyson, because, you know, everybody's like, oh yeah, Dyson, the guy that like, I wash my hands and like dries my— it's the hand dryer in the bathroom everywhere, and it's that cyclonic vacuum cleaner. It's like, no, the guy has built one of the most successful companies of all time.

SAM

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

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

SAM

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

Ooh, that's a good question. Um, I mean, James Dyson's gotta be up there because, uh, if you see the bookshelf that's in back of me, it's in order by episode number, uh, starting in the upper left-hand corner. So it goes all the way down. And so I'm, I'm going to hit like 400, uh, biographies read of history's greatest thinkers 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. The 90% of the book is just him failing over and over and over again and him refusing to give up.

SAM

And what's he obsessed with? Like, because obsessing over vacuums is strange.

So he would describe himself as an inventor and an engineer, definitely as an inventor. And so I think what I would say is what he's obsessed with is, is making the world bend to what he wants to happen. And so in many cases, if you look at his early career, he was inventing a bunch of other successful inventions and they were like taken from him because he didn't, uh, keep control of the company. There's like all these little things that are happening to him that caused him a lot of emotional pain that then he fixes in the new company. And so for him, it's just like he spent 14 years before he had the ideas. Like he's kind of similar to Steve Jobs and Yvon Chouinard. They're offended at the mediocrity of most of everything around us. They always talk about like, why does every product we use suck? They talk about it over and over and again. And so his idea is like, I bought a vacuum cleaner from Hoover. It, 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? And those then from that thought, it's 14 years, 5,127 prototypes till he has a, the world's first cyclonic vacuum up to his incredibly difficult standards that he owns 100% of.

SAM

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

That's a good question. I don't know.

SAM

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

So there is a devastating line in Steve Jobs' biography by Walter Isaacson, because Walter was collaborating with him as he was dying. And he told Walter one of the reasons he wanted to do this biography is because he wanted his kid— 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, uh, has great relationships with— he's still married to same wife, has great relationships with his kids. Some of them work inside the company, some don't. Um, but yeah, again, I spent a lot of the— as you know, because you listen to the podcast, I spent a lot of time talking about their childhood, their relationship with their father. Dyson's dad passed away when Dyson was like 9. And he said, you know, he's writing a biography when he's 75, but he still cries and gets sad that his dad— he didn't get to know his dad as an adult. His dad didn't get to see him grow up, see his success, meet his grandchildren. And so I think having that experience was just like, man, I want to make sure my kids don't have that massive hole that I had in my life. Not any fault of his own. His dad died of cancer from a young age. Um, no, so I don't think they're mutually exclusive, but yeah, you, you definitely see a lot of these highly disagreeable people. Like James Cameron is probably the best podcast I've ever done in terms of like what I like craft. And I'm really proud of that episode. I did it like 2 or 3 years ago. And I start the episode kind of, you know, giving you a hint of the highly disagreeable personality where I'm like reading from this GQ article and it's like, James Cameron has moved to New Zealand with his fifth wife. And it's just like, nobody could have a fifth wife without— that's, that, that should tell you if you're reading between the lines. That's a difficult person to deal with.

SHAAN

All right, everybody. I know when you think to yourself, what is the best video series? You think of us. When you think of who is the best creator, you think of us. And the Webby Awards are happening right now. It's like an online awards thing, and we are nominated for best video series and best creator, but it's stiff competition. Sam, who are we going up against?

SAM

Okay, so we are up against— I shaved my vag for this. Which is sort of interesting. I've listened to a few episodes, but honestly, a few, a few. We're up against Club Shay Shay, which frankly, if you're listening to this, I think you should just, you should just vote for Club Shay Shay.

SHAAN

I agree. So please go vote for the Webby, but don't vote for us. Vote for Club Shay Shay.

SAM

All right. Back to the pod. All right. Number 2, they have extreme self-confidence. And they do what works for them. So what's an example of that?

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. And he says what they had in common was that they do what works for them regardless of what other people do. Like, they were indifferent. There's another great line in that book that I think is a lot of people that you and I are going to talk about have in common, where it's like everyone wanted to be like Mike. Mike didn't want to be like anybody else. And so in situations like that, which like they are, I would say there's this line in, in Dyson's book where he calls his method of invention, his method of company building, he calls it the Edisonian principle of design. He is not a big, hey, I have a master plan. 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, I've rec— I've read 3 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 jobs. And in that book is the most detail. He helped, he was the one that, uh, that programmed the initial, uh, Safari browser. And then he created Safari browser and then the keyboard for the first iPhone. What he shows in there is like, it was just all the great products that came out of Apple were just a series of iterative demos to Steve and Steve applying his personal taste. This is why I think when you talk to a lot of investors, And to me, when I talk to them, I'm like, man, you think about business way too academically, you know, like as if you could sit at a whiteboard and like plan and master plan everything out. It's like, I don't see that in the books I read. It's like these little— a series of just small decisions every day, getting a bunch of feedback and then essentially just changing course slightly every single day and then doing that over a long period of time and constantly improving. You get to amazing products and amazing businesses.

SAM

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

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

SAM

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?

He was, he started Dell in, as a really, the prehistory of Dell really happened when he's like 16, 17. He officially started as a freshman in his freshman dorm at University of Texas. But the, the Fortune 500 thing is important because it's like, yeah, he goes, could the kid that grew up reading Fortune magazine possibly predict that I'd start a company that broke into the Fortune 500? And he goes, yeah, I always thought big. He doesn't try to hide. He's like, yeah, I had a lot of confidence. Like I knew I could do this. I believed I could do this. Now he, did he think he'd hit it at 26? Probably not. But he, he got there even faster. That's the point. He had the belief first and then he demonstrated the ability.

SAM

You also say that the— so the third principle is they're obsessed with product quality. And I hear people say this a lot, but I've— because I've never had a job, I've never been able to like 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?

You know, I love that you frame that question like that. What do they do each day? I was thinking about this morning. I was thinking about the conversation we're going to have today. And I think what all the entrepreneurs I admire have in common is how they want to spend their time is working on their company. So like, I get invited to a lot of things. I say no to most of them because like everything that's not working on the podcast is a giant distraction. And so If you go and actually look, Tim Cook said this after Steve Jobs died. He's like, if you took an inventory of how Steve spent his time, he was at Apple. And then when he wasn't 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, he's on literally the factory floor. And then he's with the design team. The important thing, and you see this, this is the problem with modern day entrepreneurship industry, is they like, like everything except actual what their company actually does. So if you can find love, right, in the activity itself, you're able to do it for a long time. I got to have, this is the main thing. I had lunch with Sam Zell, who we could talk about too. That 2-hour lunch changed my life, right? And his main advice to me was never relinquish the freedom on what you work on. He goes, the, the, the more successful you, you become, people are gonna try to constantly dangle opportunities that are distractions in front of you. And they're gonna do that for two reasons. They're gonna try to offer you more money and more status. He's like, retain your freedom. And he said something that was fucking brilliant. He goes, uh, go for freedom. If you have freedom, you can control with what, uh, 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. And so all of the people that I admire, it's like they don't want to go, you know, they're not trying to go out fundraising. They're not trying to like go party all the time. They're literally like just obsessed with what they're doing. And so everything that, like, if you take the inventory of their time, it's like the time is just spent on the company. Because I like that. Let me give you my example for me, right? You know this because you have a podcast. We can log into our podcast host right now in Chain. You can charge You could change the name of My First Million, right, to, to Sam's Club, right? You can change it whatever you want. I could change Founders whatever I want. The thing you cannot change is the RSS, the URL slug that for the, for your, the first time you set up your RSS feed, right? And that URL slug will have the first name of your podcast. My podcast went through multiple names. The first one was Autotelic. Uh, 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 if no one listens. I'm going to do this. I— it is in inside of me and I have to get it out. I'm going to do this. I would 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

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

For sure. For sure. So first of all, you know this because we've talked about podcasting a bunch and, and a lot of people like try to like part-time it. And I think literally like podcasting is a miracle. The idea that anything you want to learn, right? Me and you grew up similarly. We didn't have access to a lot of money. We didn't— I don't think you went to an Ivy League school. Like, I couldn't go to an Ivy League school at all, right?

SAM

My wife went to an Ivy League school, and when I met her and she told me first, she said she went to Penn, and I was like, is that where that football rapist coach guy goes? And she's like, no, it's like a— she's like, it's like, it's like a, it's like a big school. It's like a big shot. Like, we're like, we're part of the Ivy League. I was like, What the fuck is Ivy League? Is that Hogwarts? I don't know what that means.

Dude, I have a rather embarrassing story. Like, first of all, not only did my parents never graduate college, they never graduated high school. So the entire time I was growing up, they never mentioned the word college to me one time. And so I remember being in high school and they're like, what colleges are you applying to? I'm like, what? The one I can drive to because I got to go to school at night because I got to work full time during the day. Like, what are you talking about? I moved in, I went to student housing and I Uh, my roommate was from like Colorado or somewhere. That was the first time I ever knew, and this is really embarrassing, that people didn't work and go to school. Like, he just went to classes. That's all he did. Like, he had nothing else. I, I couldn't even fathom that. So the reason I'm so obsessed with podcasting and everything else is like, you have all, any subject you want to learn about, you have somebody that is usually spent 5, 10, you know, 10 plus years studying that, and you can learn from them for free on demand anytime you want to. How could you not be absolutely obsessed with that? So here's your question. The reason I started reading this, and I didn't even understand this, a friend of mine is the one that told me this. He visited me in Miami and he's like, it's pretty— this is like 2 years ago. And he's like, it's pretty obvious what you're doing. I go, what? He goes, you didn't have any mentors or any good, good examples. So if you're like how you are, which is kind of like psychopathically obsessed, he's like, so you just started reading and trying to find like good examples for yourself. And so there's a line, there's this guy named Larry Gagosian who built this like multi-billion dollar art business that he controls 100% of. And on the, the profile that I read to make the episode, there's a line about him. It says he got so good at selling art to the Masters of the Universe that he became one. He starts out literally selling art in a parking lot and he got so successful, he's now a peer. So the reason I'm doing this is like, I'm trying to build the best product for the best people in the world. And so, yeah, like it is, you know, I take a lot of the ideas from the podcast and just apply it to my own business, which just happens to be the podcast where I derive the insights from to begin with.

SAM

The next one is retention of total control. What are the tradeoffs of owning everything and being maniacal about the details versus delegation? Because oftentimes, for example, my favorite author, business author, is Felix Dennis. He wrote the book How to Get Rich. He's not nearly as serious as these other guys. He's like, kind of like a Mick Jagger and Richard Branson combined. He's like a rock and roll partier, but he became a billionaire. He says that delegation is the reason why he's anything, is he's like, I'm a master delegator, which I imagine a Richard Branson type of person would say a similar type of thing. Whereas you have Elon Musk or maybe Coco Chanel or a couple other folks where they 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 tradeoffs and which do you prefer?

I love that you asked this question because this is the great thing about entrepreneurship. It's like you get to decide what's best for you. Like, there is not one way. There's not one right way. I could give you examples of people I covered that delegated everything. And people that delegated nothing. I just did Todd Graves. Have you ever ate a Raising Cane's? You used to live in Austin. You're a fellow fat boy.

SAM

Well, I was a former fellow fat boy.

Former, yeah, yeah.

SAM

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

So I just did an episode on him, which I think is going to be one of the most popular episodes ever, just because when people would ask me, like, who's— you study dead entrepreneurs, like, what about the living ones that you like? And I bring up Todd Graves and like, the chicken finger guy?

SAM

I'm like, no, he's got a— he's got a really relatable demeanor.

Yeah, you want to hang out with him. But also, even if I was— even if he was a jerk, the way he built his business, you know, he owns over 90% of a business that's worth at least $10 billion. It's growing 30% year over year. And he's been doing the same thing, you know, for 30 years. And I just love everything. I'm obsessed with simplicity. I just love everything about him. But the funny thing is, in one of the interviews I found with him, he literally says, you know, people told him when he was younger, you're, you're, you're a micromanager. You have to delegate. You can't possibly do the stuff you're doing now. And he has a great line. He goes, delegate? What kind of word is that? Like, he's just like, that, that doesn't even make sense to me. And he goes, and all the people, the experts that gave me that advice, I'm bigger than they are now. And so he's literally giving this interview and they interrupt the interview because they had some event and his social media team was showing them the reel of the video reel that was about to come out. This guy's, you know, running a business. He has, uh, 50,000 employees, 800 stores, you know, 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 Glass go out, uh, without approving it. He— there's a, there's another thing, um, every single location, I approve every single new location. Uh, you mentioned Elon Musk, early days of SpaceX. He personally, 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 are, I would consider micromanagers. There are some that, you know, delegate widely. What's more important than that though is like, it depends on your personality type. Like for me, I am a complete micromanager. I'm one of the only podcasters still like still making podcasts that actually edits his own podcast. Everybody, every other podcaster tells me you're a fucking idiot. Why are you doing that? And it's just like, I'm completely obsessed with it and I hate it, but I love it at the same time. I— 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 here. It's just like really you have to think about like, how do you want to run your business?

SAM

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 also nearly ruined them.

Let's, I don't know about anybody ruined them. Um, let's use the, the, the pre, prehistory of Patagonia, right? Which is worth a couple billion dollars, privately held company, you know. And as you know, because it's in the book, in the episode, it's like he didn't, he was kind of like a communist. He didn't even want to start a business. He was a, 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.

SAM

And, you know, which, by the way, that there's a dichotomy there. If you are— if you're a communist, why do you fully own your company versus giving out equity?

Because he's obsessed with— exactly. There's a— it's almost like a paradox, right? Yeah. The— yeah, because he's obsessed with control. So that all ties back to control. Now, sometimes you can maintain control. Public company. Mark Zuckerberg has complete control of Facebook. Public company. Steve Jobs had complete control of Apple. Public company. Dyson, obviously private. Bloomberg, private. You know, Patagonia, private. But If you start there, it's like his, his whole thing was just like, hey, I'm, my life is literally hangs in the balance of these clips that people use for mountain climbing. He's like, these clips are plastic. They suck. They break. This is not good. And they, they, they would optimize for, for cost because most dirtbag climbers had no money. And so it would be like 75 cents each. And what did he do? You, you ask him what his profession is. He said, I'm a blacksmith because that was his, his trade, his craft. He's like, hey, I could do a better job than this. He starts using higher end steel and now he sells what it used to cost 75 cents because it was differentiated for $4, more than 4x what, what the market is used to paying. And he wound up sealing up like 80 to 90% market share because his was so much better. So they, if they feel that the, they're not starting companies just to start companies, they're starting companies to make products. And so therefore they're not going to make a product if somebody else is already doing that. 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. And I talk to founders all the time and even podcasters, and I'm like, man, why are you— especially in our trade, it's like, why aren't podcasters thinking more about differentiation? When I started my podcast in 2016, one, I thought it was too late, right? It's like, oh my God, I missed the boat. But I looked around, I was like, what is everybody doing? Everybody's doing the same things. Like two people, one person interviewing another. This is why My First Million first came on my radar. When I came on your podcast two years ago, I mentioned that I'd listened over 100 hours of it. Because it was truly differentiated. It's like two guys have great chemistry. They're funny, they're both entrepreneurs, and sometimes they're going to just shoot the shit and talk about ideas and brainstorm. Sometimes they'll bring people in. Like, it was a very unique format. You've seen since then, obviously, because of the success of the show, like what happens, like you have a bunch of people trying to do it and then none of them achieve the same success because they're not— first of all, they're, they're not— they're the copiers. They're not the ones that actually came up with the format and came up with the idea. So one thing I would just say is it's like It, if the product already exists, I would only make it if you see that there's a giant hole and a way to like make it better. In the case of James Dyson, there's, everybody had vacuum cleaner. They were all crappy compared to his. I paid, 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. It's the best.

SAM

Do you think that there's a common theme amongst, so everyone, most, most of the people who you've named and of maybe most of the people you cover on Founders. They're creating higher-end products where the margins are probably a bit higher. So I have a $600 Dyson. Yeah, I have, you know, Patagonia now is more mid-tier maybe. But you've covered a lot of, you know, luxury brands. And I think that a lot of like LVMH, like luxury brands tend to be the biggest and best businesses, it appears.

Yeah.

SAM

Is there a commonality of you being different and thus being able to charge more and profit more?

I don't like the one person, if you ask like my own personal Mount Rushmore of like history's greatest entrepreneurs, is they actually had like, uh, some of them obviously have big margins like Apple, right? But then like, think of Sam Walton. Like Sam Walton had the tiniest margins. Why? Because like his idea was like, hey, I'm going to be totally committed to this one simple idea, which is like everyday low price. And so the margins are small. Raising Cane's, one of my favorite entrepreneurs, his margins like less than 10%. So yeah, I don't— I think these ideas can work for— it really just depends on the industry and the business. But like you see them appear over and over again, whether it's a high margin business, a low margin business, if it's physical goods, if it's luxury goods, if it's software, it's just like kind of the same personality type over and over again.

SAM

I'm going to combine the last two, which is this— the, the first of the two was they wouldn't sell at any price. And this is the second one. Their exit strategy is death, which I love. I absolutely love. Is this particularly with AI? I don't know if you've seen— I know you're not like with it when it comes because you're so focused. Like you, I think you've said you don't pay attention to the news, you don't pay attention to social media too much. There's this thing called vibe coding. Have you seen vibe coding?

It's basically— yes.

SAM

Yeah. So it's like young kids, of which we've had a few of them on, who in a matter of 6 months can go from zero to a million a month in revenue because it's so fast and easy to make apps. Yeah. Do you think that people today are thinking shorter term than before, or has there always been a gap of a very few amount of people are willing to think long term versus short term?

I think both. I think, yeah, undoubtedly more— a larger percentage of humanity is thinking short term, and that we've always as a species been wired to be short term. Jeff Bezos has a great idea of this, is why, why he would be constantly willing to have a longer term view. His point was that like, if you're planning on a year, if you're investing in a product that may not, you know, reap any benefits over a year, you have a lot of competition. 5 years, less competition. 10 years, no competition. Like just nobody is thinking that long term. So if we have a long— I think he calls it long-term orientation. If we have a long-term orientation, then I want to do that because we just have by default, by sheer numbers, I have less amount of competitors. Now I need to back up. I am only interested in people that do things for a long term. And I'm interested in your last business. I am not interested in your, you know, your startup, your first business. In many cases, what I'm interested in is like, what is the thing that is going to— like the reason I become so close with the founders of Ramp, it's because we have this deep partnership. It's like one of the things I love is I talk to Kareem. I'm actually seeing him tonight, who's the co-founder and CTO of Ramp, one of the most brilliant technical minds that I know. And one of the things way before we became friends, way before we became partners, he's just like, Ramp's the last my last business. Like, like this is— I have all, you know, 98, 99% of my net worth into it. I spend all my days. I'm not thinking about anything else. Like, that's what I'm very interested in. And many cases to get to that last business, you usually have to start. Cream had already started, started and sold a company. Like, usually you have to go through a ton. It's very weird for like the Mark Zuckerbergs, the Michael Dells, you know, even Steve Jobs, like just to be for your first company to be your last company.

SAM

Which is what I had, I think. And I did it because I saw a theme that a lot of the people who I had admired had a hit in their 20s or 30s that allowed them to think longer term.

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, you know, financial pressure— me and you grew up with financial pressure.

SAM

It feels— and it's real.

Like it's it, it destroys you. You can't sleep.

SAM

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— you don't need to worry about rent for 3 or 4 years. That, that is— it is easier that way.

So, so to get that, like, hey, I'm not going to have to worry about feeding, taking care of my wife, my kids, feeding myself, and give yourself room to breathe, and then you're able to step back and be like, here's the thing. A lot of this is just self-exploration. Like, dude, I know myself so much better now than I did. Think about when you're like, you're supposed to be picking your career when you're in high school, because then you got to figure out what you're going to major in. It's like the stupidest thing ever. Like, nobody— if you're the same person you were at 18, that's very bizarre. And so like, I just think part of picking a successful company and a successful career you can do for a long period of time is like, you have to go through this exploration of who you are as a person and what your true interests are. The problem is with humans, like, we think, oh, like, vibe coding is really cool. I like these kids are making money. But eventually through all these experiments, they might discover what they actually, you know, truly want to dedicate their lives to. Um, so I think it's like an overall good thing. Um, but yeah, I, I think the advantage that if you as an entrepreneur, as a podcaster, as a writer, as an athlete, whatever the case is, like if you can think a lot, you just have a massive advantage if you could just have a longer term perspective than other people. And this is, The important thing is like when I'm able to choose what I work on, I'm not worried about what like my downloads today or like my audience size today. It's just like, as long as I do this forever, right? And I keep focusing on adding value to other people's lives because money comes naturally as a result of service, then I'll get, as long as I wake up every day, read a biography of history's greatest entrepreneurs and sit down once a week and talk about what I learned and do that forever, I'll let the score take care of itself. The chips will fall where it is. Like I will get everything I actually deserve.

SAM

I don't want the listener to think long-term means it's, it's okay if I don't kick ass today. And a lot of people will justify this and say, well, it's a marathon, not a sprint. And to them I say, yeah, but have you ever ran like 100 meters at the world record marathon pace? It's going to feel like a sprint to you. Like, you have to be able to run fast for a long period of time. And what I, and what, and what I mean by that is that doesn't excuse day-to-day, um, lack of urgency. You still need to be, uh, impatient on a daily level, but patient on an annual level. Additionally, can you tell me the people who thought long-term, they were still, maybe you can gimme examples, but that doesn't mean that they were broke 5 or 10 years into starting their company or that they didn't have traction or did did they? Am I wrong?

So the, the, to like close the loop on what you just said, I agree completely. If you think of like, there's not very many entrepreneurs that had a longer-term perspective than Jeff Bezos. And his line about this was like, yeah, we have long-term, but like, we're going to take step by step ferociously was his motto. Step by step ferociously. Not like, oh, we're going to lollygag. It's like, no, no, no, I'm fine being, you know, you know, we're going to be the company we want 10, 15 years from now. But every day for the next 10 to 15 years, like we're pushing the pace and we're doing as much as we can. People that were broke 5 or 10 years in, James Dyson, for sure. He was literally going to sleep covered in dirt because he's trying to build a vacuum cleaner for the entire time, going inside, crying himself to sleep as his kids are small and then his kids are completely grown up. He was in massive amounts of debt. He couldn't find no one. The reason he owns 100% of his company is because no one would, would actually want the equity, which is hilarious considering how valuable it is now.. But also he was like, he had second loans out on his, his second mortgage on his home. He was crying himself to sleep.

SAM

So he was, he was nearly bankrupt at some point.

He was, oh yeah, yeah. For, for, and if it's not the full 14 years, it was a good chunk because then he started licensing it. He had, he had some small wins where he could actually pay his bills, but he was not like a, a wealthy man. Steve Jobs, rich from the get-go, you know, app, he builds the first Apple in his garage. 4 years later, he's worth $100 million and the company's public. Like, it was pretty crazy. Fontenard broke for an excessively long period of time. Like, there isn't like a, you know, it just, it's a case-by-case basis. Jeff Bezos, already wealthy. He worked for this hedge fund in New York called D.E. Shaw, and he quit that and gave up a huge bonus to move, uh, to Seattle. But he was already, you know, able to live in Manhattan. He was working for a billionaire. Sam Walton. Now here's another—

SAM

and by the way, I think Amazon had like $100 million in sales like 4 years in or something.

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.

SAM

I tracked him on this when I like had my, I had this sheet where I tracked probably 300 people and I had timelines for each of them of when they were born, when they started the thing that allowed them to be a little bit financially free, when that period ended, and then when they started the thing that made them huge. Yeah. And he started Amazon at 32. And between the ages of like 24 or whenever you graduate college to 32, presumably he was making some amount of money, like the equivalent of $250,000 to $500,000 a year today.

For sure. For sure. Sam Walton had his first— this is an interesting thing because there is an idea, a principle I've noticed is like, go slow now so you can go faster later. And what I mean by that is like Sam Walton, greatest retailer of all time, undoubtedly. He had one store for 5 years. And so he was obsessively learning everything he possibly could about retail, doing all these experiments.. And so then you fast forward, you know, one store for 5 years. Then you fast forward, let's say 25 years into his career. He has the idea. He already has Walmart, but he's like, hey, he meets this guy named Sol Price. So I've done episodes.

SAM

How many years did you say? 25?

Well, let's say 25 years into his career, right? So, so, so the first 5 years of his career, it's one store. 25 years in, let's say around there, he, he's got Walmart, but then he, he has this idea for Sam's Club, which he got, he took from other people. He took from this guy named Sol Price who's, uh, he came up with the warehouse club idea. The founder of Costco was Sol Price's mentee when he was like, Jim Sinegal was like 18 working for Sol Price. That's where he got the idea for Costco. Sam Walton sees that, he's like, oh, 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 5 years. So when he launched Sam's Club, within the first 5 years, he gets to like 105 stores and like $7 billion in revenue. Same period when he started out, he could only master one tiny little store in Arkansas. But your skill set and your resources and everything compounds. That's the point. Todd Graves talks about, you know, I think he, by the time he gets like, he's 10, the, the Raising Cane's guy, he, I think he's 10 to 12 years into his career. He's got 28 stores. Sounds like a lot, right? He opens like 150 stores a year right now, or 100, between 100 and 150 stores a year. Go slow at the beginning to go faster later. He's learning and he's gonna apply that. This is the important thing about not jumping from business to business to business. Because if you jump from business to business to business, all you're doing is interrupting compounding.

SAM

Was it clear— a lot of these, you know, the world's greatest entrepreneurs— was it clear that their TAM was big enough to achieve their ambitions?

No, absolutely not. No.

SAM

Like, for example, you'd be like, look, this chicken finger thing, that's maybe silly, but I guess McDonald's is huge. I guess you could be kind of like McDonald's.

I think if he did think of anything, he thought of In-N-Out. Uh, In-N-Out was founded in 1948. If you look at In-N-Out's menu, looks like Todd Graves. There's other people before him, but it's like, to me, Todd Graves is just Harry Snyder reincarnated, who was the founder of In-N-Out. But instead of doing burgers, he does chicken fingers. But no, like, uh, I just went over this because I'm going through the Michael Dell episode right now. Like, there's just like no way. Like, you knew computers were like, most people hadn't even seen a computer and like, he was just completely obsessed with it. So there's no way he could have predicted the financial success he was going to have and that, and how big the market could actually get. You know, he started with Dell with $1,000, no venture capital, $1,000. And his main competitor was Compaq, who started with like $25 million of venture capital. And Michael Dell, super competitive but nice. The book's called Play Nice and Win— Play Nice But Win. But he's like, he's constantly contrasting. He's like, I started with $1,000, they started with $25 million. I'm kicking their ass. It's really funny. And Dell would tell you that having the constraints of limited capital was really good at the beginning because it forced him to innovate into, in a way that you wouldn't if you had money. And I was like, oh wow, that's interesting. So I go and pull my highlights from Sam Walton. Sam Walton said the same thing. Kmart existed before Walmart. Kmart was dominating the big cities because if you're going to start retail, where are you going to go? You're going to go to Chicago, you're going to New York, and go to all those other places. So he's like, well, I can't go there. I don't have any money. So he starts going in these little towns in rural Arkansas. And what he learned, he goes, oh, constraints are your friend. Because if we were, if we were better capitalized, I would have never went out into these tiny little communities And what I discovered is in these tiny little communities, there's far, far more business than we could have ever predicted. Perfect example to your, to your question.

SAM

You're the man, David. I appreciate you doing this. I could just like, I think the listener will notice this is probably the podcast that I've spoken the least amount of, of all 700. I, uh, I've, I've listened to, uh, hundreds of your episodes. I think you're at like, what, 400? I think I've listened to half of them now.

I appreciate that.

SAM

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

CLIP

I feel like I could rule the world. I know I could be what I want to. I put my all in it like no days off. On the road, let's travel, never looking back.