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We put a multimillionaire’s portfolio into Claude (the results shocked us)

48m 7s

We put a multimillionaire’s portfolio into Claude (the results shocked us)

This episode explores the power of making fewer, better decisions and how top performers manage fear, risk, and motivation. The hosts open with a retail investor they met in Hampton who sold his company for eight figures and then earned roughly a 22% annual return for over a decade, beating the S&P 500 in 11 of 12 years. Strikingly, he averaged only 2.9 stock decisions per year, owned about 15 stocks, and made zero decisions for three years. His approach is to study a handful of understandable businesses deeply, keep detailed notes, and wait patiently for a cheap entry point. The conversation then draws parallels to Warren Buffett's "lethargy bordering on sloth," Kevin Ryan's one-good-idea-per-year rule, and Jack Dorsey's pre-mortem listing 140 reasons Square would fail. The hosts contrast investing, where avoiding mistakes is paramount, with entrepreneurship, where big swings can pay off enormously, citing Mark Zuckerberg and his acquisition of Alexandr Wang's Scale AI. They also discuss the DARE method for panic attacks, exposure therapy, and Georges St-Pierre's fight-day rehearsal routine. A recurring theme is identifying which "game" you are playing in life, and the episode closes with motivational ideas about staying in motion and keeping your sails up during hard times.

Transcription

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English
Speaker 1And I was like, what have you been doing? He's like, well, actually, I'm a public investor. I invest in public stocks. You're like, oh, you
Speaker 2lose money for a living.
Speaker 1Yeah. I was like, I'm pretty nosy. Do you have your laptop on you? Pull up your brokerage account right now. And he did. So check this out. So a few weeks ago, I met this guy in Hampton. And basically, his story is that a while back, he sold his company and he made something like eight figures in money after he sold his business. In money. In monies. We're a business podcast.
Speaker 2We've done a thousand of these episodes. He sold his company, made some revenue, some income, some money.
Speaker 1Some monies. Yeah. And he did. And I was looking through his whole brokerage account. And I want to show you his results. But basically, he's had nearly a 22% annual return for the last decade, which is amazing. But that's not the interesting part. I had this idea where we basically exported his brokerage account. And we put it in Claude. And we asked it, over the last 12 years, how many decisions did you make a year? Decision is defined as how many stocks you bought or sold in a year. And if I remember correctly, he's roughly owned around 15 stocks over the last decade or so, give or take five. But what was interesting is that he only made 2.9 decisions a year. And we put together this cool graph. And there were some years, I believe, three out of the last 10 years, he made zero decisions. And at most, he made six decisions in a year.
Speaker 2So let me just read the kind of because this is a great graphic, by the way. So if you had put $100 in when he started, so this is 2014. So 12, 13 years, he's averaged his annual return is 21.8 versus 13.5% for the S&P 500. For three years, he did nothing. That was the longest stretch of no activity. That was 2022 to 2025. And it looks like he beat the market 11 out of 12 years. It was only one year where he didn't beat the market. And that was 2022.
Speaker 1And basically, if you were to invest around $10 million when he started, I think that math is something like $60 million, depending on what part of the year you started. The reason why it was interesting to me is even though I preach patience, I mean, I preach all this shit. I sound very smart when I preach this. But you and I are very similar. We move a lot. And we oftentimes mistake movement with progress. And I thought it was really interesting to see this guy's numbers every single year. Because when you think about three decisions a year, that's four months of just thinking, planning, plotting, not doing anything, zero action.
Speaker 2By the way, what was he owning? Is it like he basically bought the Fang stocks or was he buying obscure things? What was he doing?
Speaker 1They weren't obscure. One was a very. I don't want to reveal too much of his info, but one was a very large travel stock. So imagine a popular airline or something like that. Another one was a popular clothing stock. It wasn't Lululemon, but imagine like a Lululemon, things like that.
Speaker 2And so he was. When you say he's got four months of thinking, was it actually four months? Was he just sitting every day and doing research, basically? Was that his actual day-to-day task? Or he was more of a passive investor, kind of set it and forget it, and then sometimes would hear something or learn something and decide to make a change?
Speaker 1So I texted him. I go, hey, I want to talk about this. Do I have your permission? He said, yeah. And then I said, how do you actually make decisions? Because I am curious, 2.9 decisions a year, what are you actually doing? He said, I study a few things that I can understand. I study a few things that I can understand. And then I said, I study a few things that I can understand. And I study them very deeply. I keep very detailed notes. And then I just wait for an opportunity. Blank Company, for example, I had studied them extensively for about six months prior to COVID. And I really liked it, but I thought it was expensive. And so I spent a lot of days writing notes about it, documenting my research, saying what I've learned, reading the annual reports, and I keep an eye on it. And then when the market presented itself and the opportunity presented itself and it got cheap
Speaker 2enough, I bought it that day. So he is doing the thing, right? He's basically spending every day learning. And then when there's a moment in time, going ahead and making a position. What surprised you the most? Was it the number of decisions? What else surprised you?
Speaker 1A few things surprised me. The first thing is, we love having investors on here from Howard Marks, Ray Dalio. And we're not investors. Not exactly. Sometimes maybe it's like a side hobby, but I'm interested in those people because I'm very curious because it's such a black and white way of thinking. And I'm very curious because it's such a black and white way to figure out someone's decision framework. Because there's very clearly like, I thought about this, I executed this. Whereas with startups, it's a little bit more iterative, where you can go back in time and fix something because you can build it on the fly a little bit. And so I'm very fascinated by this. And there's this cool quote. It's by Warren Buffett. He says, his investment strategy is lethargy bordering on sloth. That's the cornerstone of his investment thesis, which I thought was interesting. And I was like, that's so fascinating. And we had Kevin Ryan on the podcast. Kevin Ryan is a guy who owns sort of like an incubator, a startup lab. I don't know how you describe it, but they've launched a handful of like 10s of billions of dollars startups. And he was like, I basically get one good idea a year. And I thought that that was interesting that a lot of the people who I admire, they do tend to make very few decisions throughout the year. The second thing is that they don't agonize over very small decisions. I know that this is something that I do often. And I think the way that you fix this is you determine what decision is reversible. And when you do that, you're going to get a lot of good ideas. And I think that's which isn't. And for the ones that are reversible, don't sweat over them. Don't agonize over them. I actually think there's a world where you're quite good at this, where you're good at like categorizing which decisions are important versus which aren't. Would you agree?
Speaker 2Yeah, I do think I do that pretty well. But it's because.
Speaker 1On this show, we have spent hours talking to some of the best investors alive. Well, lucky for you, the team at HubSpot, they have pulled out the principles that matter most and turned it into a very simple, easy to read wealth guide. It's 35 principles from the top investors. We're talking guys who have been on the pod like Howard Marks, Manish Pabrai, Morgan Housel, Cathie Wood, and a ton others. So these are all their frameworks, their mental models, their rules, basically how to play the long game and how to avoid ruin. You can get it in the link below.
Speaker 2My default state is I don't care. So it's pretty easy then. Everything is ruled out unless it has a real reason I need to care. Whereas I think if your natural wiring is the where you really are anxious or you think about everything and you think about everything, it feels like everything matters by default. If that's your default, it's very hard to then pull down 89 different things and convince yourself that they don't matter to find the one that does. So I think it's a lot of just your kind of nature in that sense of my nature is to not really care about most things.
Speaker 1My nature is the opposite, which is I tell myself, well, like the way you do one thing, there's all these cute phrases we talk about. The way you do one thing is the way you do everything. Therefore, if you have a typo in this sentence, you're going to make bad business decisions. You're sloppy. Yeah, you're just a mess. And so that tends to tell my neurotic voice or my neurotic voice is kind of like telling myself like, oh, well, everything matters. But the last two things I noticed that these people are trying to write down like trends I've noticed amongst these people is that they know their circle of competence quite well. And there was a time where I was telling my friend, I was like, hey, have you thought about investing in this company? And I made this all up. And I was like, well, I don't know. I don't know. I don't know. I don't know. I don't know. I don't know. I don't know. I don't know. I don't know. I don't know. I don't I was like, I'm not actually going to do it, but I do like to study it. And he was like, yeah, that all sounds really good. I don't know anything about that industry, though. So no, I would never do that. And I've not ever thought of it. And there's this like weird, like, they say no, not because it's a bad opportunity, just because it's not within their like realm of genius. And then the last thing was they tend to write their ideas down, where they will write it down. Oftentimes, you'll notice people write pre-mortems. Have you heard of a pre-mortem where you write down everything that can go wrong? Like, was I still happy? You don't want to do this thing like this was a bad decision because the result was bad. It should be this was a bad decision because the input or the framework was bad. And so they do things like pre-mortem or they journal or they'll make arguments to themselves on why this is or is not a good idea. So those are some of the trends I've noticed. But I thought this was really cool to see on paper how many decisions a year this guy's making. He's a retail investor who's outperformed the market.
Speaker 2Have you heard of the Jack Dorsey pre-mortem he did before he started Square? No. What did he do? So Jack Dorsey had helped create Twitter. Supposedly, it was his idea for Twitter and he was the CEO of Twitter for a long time. So his next company was going to be Square. And it is very easy when you just were the guy who created Twitter and all of Silicon Valley has purchased real estate on your balls. And it's very easy to get high on your own supply. And so what did Jack Dorsey do? He humbled himself with a pre-mortem. And so before he started Square, I think he created a list called 140 Reasons Why Square Will Fail. And he wrote down 140 Reasons Why and he gave it to
Speaker 1Can we put buying real estate on your balls into the Hall of Fame?
Speaker 2You know, sometimes it's like words just come out of your mouth before you can think about it. That one, I had the idea and I made a decision. And I said, I'm going to let this one fly. Yeah, that would just put its place in the Hall of Fame. We're not meant to be silent, let's put it that way. And I decided to let it go. that one rip okay so so yeah so jack dorsey wrote this thing and he said it was very useful because it's kind of the charlie munger thing where tell me if you know all i want to know is where i'm going to die so i know not to go there and um if you know why the reasons your company might fail in advance you can then and not avoid that not not avoid the elephant in the room well then you can actually design a company that's going to achieve despite those potential failure modes you also so you know while you were talking about this i was thinking about mark zuckerberg while you were talking about it because he recently has been doing a lot of press he's on a bit of a victory lap at the moment again which feels honestly a little premature because like ai changes every the leader changes every you know six months of who seems like they're dead versus who seems like they're ahead and right now muse is doing really well and so he's really excited and he's going out and talking a bunch and
Speaker 1but the stock agrees that it was a good decision so far
Speaker 2right sure um so he's but he's doing all kinds of stuff uh he's dropping f-bombs in interviews now which he did he really yeah that doesn't seem natural what did you say there's two different ones we could play the clips but the the first one he's in the backyard he's he's like barbecuing and so they were it was some he was like facetiming somebody and they were like oh mark you smoking you smoking meats again because remember like many years ago when he was trying to be trying to be cool and casual and he outed himself as a robot and he was like i'm gonna do this i'm gonna basically yeah and he was like i'm just smoking some meat in the smoker and he tried to have like a chill four-hour barbecue stream that didn't go well so this time he was like smoking meat like what type of meat he goes whatever the f- we want oh my god and then the second one he was talking about he did an interview with alexander wang who alexander wang is i think the youngest billionaire in the world right now so alex wang uh was a kind of math olympiad kid who then went on to start scale ai which is a really good thing and he was like i'm gonna do this i'm gonna do this i'm gonna do this which was like the one of the first big data companies for these are ai labs meaning the ai labs need data to train their models where do you get that data it's you know takes a lot of it's a grindy kind of operational business to go collect and have clean data for the labs so scale was doing that ultimately uh meta bought it for i think 15 billion dollars or bought like a huge chunk of it and acquired they basically a big part of it was just getting alex and so they asked zuck they go in the interview they were like why you know why alex and he's like yeah it's kind of weird right like what is this data guy going to do with the social media guy and that's going to be like the leading ai lab how does that work they say like this is why i just kissed him on the mouth and he's like this is my golden child basically verbally verbally kissed him on the mouth so they're sitting there this is on cheeky pint and he's um he says i tried to meet as many of the great founders of his kind of age group his generation as i could and i you know i would try to meet as many of them as i could and he he said i just realized alex is the guy he's the guy and that's it he's the guy and he's complimenting like in this in this like just more absolute not overly intellectual thing but he's the guy and they were you know they were talking about how you know meta was getting trounced for when they were doing vr and he was calling you know talking about the metaverse and then it was just kind of like it wasn't really working uh he said i think he'd put like 60 billion dollars or so you put an absurd amount of money into developing this like 10 times the amount that they they spent developing the iphone was spent on oculus and the vr program and it had produced nothing on par with the iphone so in terms of popularity and users actually wanting it and so he was wrong in that but when ai came around he correctly pivoted to it he said out loud he goes yeah this is a type of game where you're not like it doesn't he goes you don't get judged by your mistakes you're only judged by the things you got right and how right you got them when you got them right and so he kind of has given himself permission to make mistakes but make the type of mistakes where if i'm right i'm going to be right in such a major way that it wipes out the history of all the battles i lost because i won the war and if you know zuck he like loves the roman empire he loves war he loves his favorite game with civilization and um if you see even his shirts are like like latin for you know the it's always like latin phrases for like give me zucker give me nothing you know like stuff like stuff that used to be like about caesar and so i just think it's an interesting idea that's very different than investing of what you were talking about where investing warren buffett's you know famously is like you know rule number one is investing is don't lose money rule number two don't forget rule number one where it's about having not making mistakes whereas entrepreneurship is the opposite you can make tons of mistakes as long as when you do get something right you have enough chips on the table and you actually get them right in a big enough way in baseball the most you can get from a great hit is four runs but in business you can get a thousand runs with one correct swing of the bat and so you just have to focus on getting those correct swings of the bat because when you do it's a thousand x it's a ten thousand x
Speaker 1can i ask you a question about this uh i want to ask about the zucks up but for alex wang uh he's 29 so scale was a 14 billion dollar company so one of the largest private companies uh maybe top 200 or something whenever he was bought or top 100 when i hear what you're describing it's sort of like you're saying zuck was saying this guy is technical and knows what he's talking about and i've interviewed all these people and you almost sounded like you're describing him as an individual contributor are you saying that this guy led a 14 billion dollar company and typically if you're the ceo of a company that big you're not the smartest in the room you're just pretty good at a bunch of the important stuff but when you described him it was like oh he's a great leader he's good at everything and also he knows ai better than all these other people so he was
Speaker 2saying what he said about him specifically was his strategic mind so figuring out what should we be doing his clarity of communication so his ability to communicate that effectively and then his like strong beliefs on execution so for example that for meta to win in ai they needed to have an extremely small team working on it not a big team so talent density how talent density was one of the most important factors in the in the victory in victory in ai meaning what you don't want is 2 000 pretty smart people on this you want 20 or max 200 extremely smart people who can all hold the problem in their head the whole problem project in their head and they all know each other and they're talking to each other and it's tight and there's not too many voices in the room and that it should be extremely flat and then the way it's organized so he had these very strong opinions that zuck believed was the correct answer and that because of that they should go ahead and try to pull it off so that's what he he kind of said about him he kind of described as his his attributes of what what it meant when he said he's the guy so a
Speaker 1leader kind of for sure like leadership ability not not he's not doing all the work another
Speaker 2interesting part of this was um is they were asked i think it was on senra's podcast and senra was asking him like so how did he know that you were good at those how'd you even meet the guy how'd you even meet mark zuckerberg why why'd you mean he said well you know meta was one of our big customers at scale but he goes yeah it's kind of just like does this every once in a while like every few months you know he would uh like he just hits you up and he's like he'll send he's like if i ever sent him a question in whatsapp like hey what do you think we should do about this i would get this extremely thorough extremely crisp whatsapp message that's almost like a blog post length delivered back to me because that's just one of zuck's like superpowers he's an extremely good writer he's extremely clear in his thinking and he's able to the way most people send short quick text messages he's able to send long thorough text messages in the same amount of brain power like in the same like time that it takes a normal person and then the exact opposite was true was he goes he also is quite you know humble for stuff for a guy who basically runs one of the um you know the most valuable companies in the world he would always just text me hey what do you think we should do about x he's like and it wasn't just me he's sending that to you know 20 people that are not on the official board of advisors he's not waiting for the quarterly board meeting to discuss this with these like you know five-star generals he would just anybody who we thought was smart he'll just say hey what do you think we're getting wrong here hey what do you think what do you think we should be doing about this and you know he's not necessarily going to just do what we say but he's constantly seeking from very smart people their take and then he's also using that to assess the talent of those people of who he thinks is consistently giving him back high signal on those
Speaker 1things so i guess there's like two uh sides of the spectrum but basically like there are people where it's a dictatorship and they like for example um cornelius vanderbilt was like basically sort of like the elon musk of uh the 1800s he was the richest man in america and he was known for just like he would make decisions with very little transparency people wouldn't know why he was doing it he was described as shrewd where he would make a decision and people would be like we have no idea why you're doing that and six months later it would reveal itself like oh he was right he predicted this like he was doing all this stuff in secrecy but then there's so many other leaders that tend to make decisions almost in a consensus way which is very different from how leaders are um and i have noticed that when i have when you and i or i have hung out with like people that are a hundred times more successful than i am oftentimes they'll ask my opinion and in my head i'm like i'm way dumber than you why are you asking my opinion like and i could tell that they're gathering information and i have found that to be like a superpower amongst a lot of leaders yeah
Speaker 2there's a what's that thing called dunning-kruger uh the dunning-kruger effect where if you know nothing about a subject you have very little confidence if you know a little bit about the subject you have this false sense of too much confidence on it And then as you actually learn more about it, you realize how little you really knew and your confidence on the subject dips, right? And this is why black belts in jujitsu who've been doing it for 20 years are the ones who talk about how, like, I'm still at the beginner. I'm a beginner at this. I'm still just figuring this stuff out. There's so much more that I don't know than what I do know. And then you have Jonah Hill who becomes a blue belt and is like, I'll murder anybody who fights me. You know, like, it's like you get that blue belt confidence. The blue belts feel like black belts and the black belts feel like blue belts. Like, it's this weird thing that happens with how much you know about a subject. And it does seem like, you know, some of the smartest people are the ones who are the quickest to, A, admit how little they know. B, understand how big of a factor luck is in their success. And C, constantly be searching for insight from people who, on paper, should be, you know, are less accomplished, less intelligent about the subject than they are. Because they know they're kind of always hunting for anything that resonates, anything that has some signal to it. And they know it can come from different places. And they're humble enough to do it.
Speaker 1The shitty part about doing this podcast is I signed up for an executive coach. And I've, like, done three or four sessions with him, plus this, like, assessment. And he was like, you're really self-critical of yourself. I'm like, dude, it really sucks. My job is I hang out with the people who are the best in the world at everything they do. And he was like, you described yourself as lazy. You said that you're not ambitious. He's like, you seem very ambitious. I'm like, I am hanging out with literally the 30th richest person on earth. Would you compare, like, whatever it is I am doing compared to that? It is actually quite challenging because I realize what the levels are and how high they go. And every once in a while, I will definitely, like, shit on myself for feeling that way. Do you feel that way sometimes?
Speaker 2I mean, I try not to, but I definitely. I definitely feel that way. You know, what are the comparison, Thief of Joy bullshit? You know, like, yeah, that's definitely true. The only way to cope with it is to do two things. One, get comfortable in the game you're playing. That I'm not playing the game that those guys are playing. Those guys are trying to change the world or they're trying to be the richest guy in the world or they're trying to have the most power. They want to run for president. I don't want to do any of those things. And, you know, so that's the first thing is I get really comfortable in what game are you actually playing. And I don't think most people even are aware. Of what game they're playing in life. Like, if I ask it, if you ask a normal person or even you ask one of your smart friends, do you think they know what game they play?
Speaker 1No. And, in fact, I've been doing this exercise where I've been asking people, like, before they ask me advice or whatever, if they're wanting to brainstorm with me on their problem, I'm like, well, where are you trying to be in five years? And they'll be like, I don't know. I've never thought about that. Like, there is a. Even amongst really successful people, driven people, there is a lack of, like, the end state looks something like this.
Speaker 2So, I want you to. I want you to imagine. Close your eyes and imagine a friend who is somebody you respect, smart, accomplished. Let's say somebody you think is smarter than you and more successful than you. All right? Yeah. All right. If you ask that person, what game are you playing? What do you think that would be the words that come out of their mouth?
Speaker 1They'd be like, what are you talking about?
Speaker 2Like, it would be, like, shock. Okay. So, first, they're confused. What are you even really asking me? And then you sort of explain. Well, we're all playing some sort of game. And maybe. LeBron James is playing right now. LeBron James, age 42, is playing a game of, I'm trying to defeat Father Time and catch Michael Jordan. That's really what he's doing. So, he's trying to defy the laws of aging to keep playing basketball at age 42. And then he goes and joins Philly because he wants to win a championship and he wants to, you know, really cement himself as the greatest of all time. Right now, it's him and Jordan who are comparing. That's the game LeBron is playing in the NBA. Now, another player on his same team might be playing a different game. Jalen Brown, who just left the Celtics. Or, you know, got traded away from the Celtics. And he was always the number two there. And I think he wants to show what he's really capable of. He wants to show that, you know, I would say this year he's playing a game of proving himself. It's a prove-myself game. I want to prove I'm one of the best players and that they made a mistake trading me away.
Speaker 1And most of the NBA players, probably if you talk to them, I've talked to a couple of these guys, they're like, I'm just trying to have fun and make a good living.
Speaker 2Yeah, exactly. I'm trying to, you know, get this bread while the bread is there for the getting. You know, I'm trying to make my first All-Star team. I'm trying to make my first All-Star team. I'm trying to get that next contract. I'm trying to do something. And so, if you break it down into the Aaron Sorkin way of thinking about things, the hero has something that they want and there's something that stands in their way. That's a story. Intention and obstacle. And so, you know, for example, when we were in our 20s, what was the game we were trying to play? If we're honest, it was trying to make it. And I think make it meant be a successful person, make money. You know, become a multimillionaire was, I think, both of our goals. Hence, you know, part of the spirit of this podcast, why it works. Because we kind of shared that. Chase, that's when we met. And we were both chasing that same thing. We were both playing that same game. Now, we played it different ways, but we were both fundamentally playing that game. And then when we got into our 30s, it was like we started playing a different game. It was this family, I'm going to start a family while still being successful, but not in the sweaty, grindy way I played in my 20s. And I didn't know what that meant, but I knew that's what I was trying to do. And figured out how to do that through some combination of investing and having kids and doing all this good stuff. And, you know, then you might play a different game at a different phase. And so, what do you, that person you were thinking about, what game do you think they're actually playing?
Speaker 1Probably just trying to do the same thing they were before, which is they're already successful, but they want to go a level above and be more successful and more powerful and more prominent.
Speaker 2And what's the why on that? They don't feel like they have enough. They don't feel like they've proved it.
Speaker 1They feel like they won their game and they need to win another game in order to feel whole.
Speaker 2Right. Okay. So, I think it's, you know, but if that person said that out loud, they'd probably feel a little bit silly saying it.
Speaker 1They'd feel stupid. I don't know. I've never thought about it. Dude, I'm just trying to, like, build something great. You know what I mean? That's really, like, the answer.
Speaker 2Right. To get somewhat defensive. There's a great book called The Score. And it talks about how games are this incredibly powerful thing. So, let's take a game. The way he says it is, the game, like, if you decide to play a game, the game decides what you want and who you need to be to get it. So, for example, he's like, let's say you play a game like, let's say, Charades. Well, to play a game like Charades, what do you want? It's like, I want my team to guess what I'm doing. And so, who do I need to be? It's like, I need to be really expressive. I need to be really collaborative. I need to be a great communicator. That's what I need to be to win this game. If that same person goes and plays Mafia, it's like, I need to be a lying, cheating bastard. I need to be a scoundrel in order to win this game. And it's like, it will change your whole personality depending on the game that you play. It'll tell you what matters. You play a certain game and then all of a sudden, mobility and flexibility matters because you're playing Twister versus another game that where you're playing, you know, a bodybuilder and you're trying to be as strong as possible. And who cares about flexibility? It'll completely change the shape of your body depending on what game you play. And so, I think it's pretty wild that most people put zero effort into this.
Speaker 1I just added it to my Goodreads. I'm reading it. Good suggestion. Normally, when you say you read a book, you don't really read the book. So, if you've read this whole thing, then.
Speaker 2I didn't say I read the whole thing. I got like a voting majority. I got over 51%. Hey, let's take a quick break. You know that feeling when strategy is done, the brief is written, everyone's aligned, and you realize someone still has to sit down and actually create all the content? That someone is usually you, and it's due tomorrow. Well, the Breeze Assistant from HubSpot can help. It works right inside HubSpot. You can draft a campaign copy, blog posts, emails, all in your brand voice, all using your actual customer data. So, you don't create just content. You create content that converts. Check out HubSpot.com, the agentic customer platform for growing businesses. I want to give you one more little. Because we are Krispy Kreme right now, and it's just a full glaze of Silicon Valley CEOs, I want to read you one more. One more little story here about Elon Musk. Can I do that? Can we just finish the glaze?
Speaker 1Yeah, I don't think you glazed Zuck, by the way. I think you made fun. Did you see him? There was a meme of him trying to enjoy. So, basically, the thing you're talking about is it was Zuck and Alex Wang, and they were drinking Guinness, in an interview with the Stripe founder. And there was this funny meme of him drinking Guinness beer. And they were like, check out Zuck trying to act like he likes drinking Guinness beer. And you could tell he had a little bit of a scowl when he tasted it. And it was sort of like a 17-year-old going to their first college party.
Speaker 2Okay, here's the thing. Everyone's making fun of him. To me, most relatable thing Zuckerberg has done in decades. Anybody who's had their first sip of Guinness is like, what the hell is that? Remember the first time I drank Guinness? I literally had the same reaction. The face he made while he's like to the side, like. And then he's doing like the. There was no music played, but. No, it's good. It's savory. That's what I wanted.
Speaker 1I like my beer creamy. What did he say? Okay, what about Allah?
Speaker 2There's an Elon story that I don't even know if it's true, but it's kind of like, who cares? It's a good myth. It's a good fable, if nothing else. So, it says, Elon Musk was asked, Elon Musk was asked, asked at a private dinner, what he would do if SpaceX and Tesla both failed. Simultaneously, he lost every dollar he had. I believe this was back in like, according to the story, this is like back in 08, 09, when Tesla was on the brink of failure, and so was SpaceX after three rockets failed. The question was intended as a simple hypothetical. Icebreaker. But his answer lasted eight minutes, and the table went silent. Here's what he said he would do. He said he would move to the cheapest apartment he could find, buy a computer, and start building the next thing within 24 hours. Not a week later, not after processing the loss, within 24 hours. He said the loss of money would not bother him but the loss of the companies would devastate him but he would only let the devastation last one night the building would have to start the next day somebody asked what would the next thing be he said he doesn't know and that not knowing would not slow him down the thing finds you you just have to be building when it arrives i think it's a pretty powerful idea and i wanted to share it here because that advice has really helped me in life my dad told me a very similar thing he goes you know yeah you want to know which direction to go but if you don't you just got to get moving it's it's about motion not direction and once you're in motion it's a lot easier to figure out direction and it's not that hard to change direction once you're in motion but it's pretty hard to do anything from a standstill and so this idea of of you know you just got to get moving and and kind of be in a state of action when you're in a when you're in a world of uncertainty didn't you just
Speaker 1have something like that in your newsletter was that your newsletter that's said something about actually plan and action there
Speaker 2was a napoleon quote that was very yeah that was great that's napoleon sir what is your next plan he replied i act and the plan emerges from my action and i really like this scott galloway had a good one that was on what he said on the podcast and i remember writing down where he goes you got to keep your sails up and we asked him we go what do you mean keep your sails up and he goes um like look when shit's not good it's pretty easy to just get down on yourself and like droop but like if you're a boat just keep your sails up because you're not going to get down on yourself and you're not going to get down on yourself and like droop but like if you're a boat just keep your sails up because you're not going to you want to be ready when that wind comes and it'll give you that boost but it won't it won't work if you if you put your sails down when you're down and i just thought that's just like a great piece of motivation for people is like look all right you might be getting your your shit kicked right now but keep your sails up because that wind will come and when it does you know it'll help your boat so this is like a little bit of you've talked about this like motivation corner yeah motivation is this cheesy thing that you're supposed to be too smart for but i don't know kind of kind of love me a good quote i do too when
Speaker 1we've said basically like motivation is good when you're like not successful but you want to be successful it's not particularly good when you're in the thick of it and then it's also good again when you already become successful and you're like what do i make of all this right what uh when have you applied this to your life you
Speaker 2know i remember when we were doing our first company and things were not going well um we like blab era no this was like in the sushi era i just remember i was living in an apartment we were sleeping on air mattress we had like i just remember we didn't even have like little like we didn't have a trash can we would just take the garbage bag and we had a nail that we nailed into the wall and we would just nail the garbage bag to the wall and i remember like we would go out and like you know if if any friend or a girl came over to our apartment she was just like what is what what are you guys this is terrible and it was like kind of unnecessarily bad meaning we were letting the badness of our company seep into the badness of our life and that was a mistake and i remember one day we lived in boulder you're like i deserve
Speaker 1this i'm filth i don't even deserve a trash can yeah exactly we we
Speaker 2treated ourselves poorly we let kind of like the last play effect affect the next play if you ever play sports it was like a next play mentality we didn't have a next play mentality we had a last play mentality things were bad yesterday probably gonna be pretty bad today we weren't saying that but we were acting that way and our level of productivity was going down and actually to switch it didn't require anything to change in our business it didn't even require a new strategy we just changed our routine and so we we kind of got our sales up a little bit meaning we um i remember we went for a hike we just like one morning we were like forget work we're going for a hike and we lived in boulder and we we hiked the flat irons and we were just on such a high from physically doing something hard and having like a win even though it was a win unrelated to the business it was a win to ourselves and then when we came back in we like had a better attitude therefore had better ideas and we were like oh my god i'm so sorry i'm so sorry i'm so sorry i'm so sorry because and we had better ideas we actually kind of believed in them a little more because we just had a win this morning and this is all sounds very basic to anybody who's like lives a good life and has like healthy routines and whatnot but we were in a bit of a downward spiral and needed to like reverse it and reversing it like what we thought needed to reverse was that our situation needed to change or our outcomes needed to change or like success needed to change in actuality we just needed to like do some basic shit to get our sales back up it's like get the trash can go for the hike clean up the room you know wear your good outfit today like let's go let's go like start stacking some small wife wins and uh and then operate from that place so
Speaker 1a lot of times people at the podcast they'll reach out to me and they're wondering hey sam and sean how do you meet all these amazing entrepreneurs how do you find all these stories well i have a hack you see i actually have a community called hampton it's a community for entrepreneurs doing at least three million in revenue although we do on average just something like 25 million dollars a year in revenue we have the founders of doordash a figure of blue chew all these amazing companies are part of hampton and what's interesting is because of the environment in hampton which frankly is very similar to my first million we have a very unique high trust environment when people apply and go through this vetting process they're put in groups of like eight or nine other entrepreneurs and they get real about everything that's going on in their life and in their business and sort of like when people listen to mfm they get inspired to come up with new solutions for business that's what happens in real life in hampton it's life-changing and so if you're a founder of a business you're going to be a part of that and you're going to be a part of that of a startup that does at least three million in revenue and you just want to go ahead and pull forward five or ten years worth of success then check it out the url is joinhampton.com again the url joinhampton.com i think that these things that you're talking about like we can make fun of them because they're small and it seems silly to like tell your tell your bros like about these small little motivational things but they make huge impacts for example i hate flying every time i've flown for the last 15 years i've been on xanax i take i have been on xanax for the last 15 years i have xanax for flying i hate it i read this book about a month ago it's called dare d-a-r-e and it's the drug program it's the same name but it stands for um it's a book on how to deal with panic attacks and the d stands for dismiss and so what that means is yeah i'm gonna get panicky so what who cares whatever a stands for allow and be like yeah let's go i'm ready i'm ready i'm ready i'm ready i'm ready which is now i want it i want this panic attack to come faster let's go baby and then e stands for engage once the panic attack has reached its climax you think okay it's passed let's engage in a new activity uh let's read let's listen to whatever music i'm listening to let's engage in this conversation and i read that book and i had a flight coming up i had to go to jackson hole the other day and i went sober it was the first time that i've done that in 15 years and it was because of that one like i i read i i read half the book because i i just needed to for it to tell me what dare meant and i was like i'm good i'm gonna try that and so i found myself like putting myself in situations where i would
Speaker 2get anxious walk me through your where did you start the d is it at the airport is way before that walk me through step by step
Speaker 1there was two one was it was the first time that we had left both of our kids for like a four night trip so i was like nervous not because my i was going to miss them but my little girl was showing a little bit signs of separation so i was starting to get nervous and so i found that it was like compounding i was like getting her worked up and i was getting and i was like oh my gosh so i started it the night before but then when i got to the airport i found myself like okay and about 40 minutes i'm getting on that plane the door's gonna shut and i'm gonna get panicky let's go let's see how powerful this thing is i'm so excited to put this into place i'm pumped i'm gonna get panicked i'm gonna freak out for a minute and i'm gonna see how wonderful this new exercise is i'm so excited and there is like some science behind this which is basically like when you want to get panicky it's kind of impossible to get panicky it's like do you know do you know are you actually crazy if you tell yourself that you're crazy and you're aware you're crazy it's like one of these things where it's like hard you know it's like uh some weird logic like that but um and so like 40 minutes before i was like all right i'm gonna feel it and then when i actually sit in the seat i'm like in two minutes they're about to close that door and it's go time there's no getting out i'm trapped in here baby like it was as if like uh instead of like being like i'm trapped in here with you it was like you're trapped in here with me now like yeah i remember like it was as if i'm in the octagon with this is like you hear the door close it's like you're stuck baby uh like and i have and it totally worked this exercise which was totally a woo woo mind thing was it like
Speaker 2night and day meaning it was a totally different experience or it was just a lessened version of what you usually have you know it's messed up i've
Speaker 1flown a little my whole life it landed it's on the tarmac after we landed jackson hole it land land land it takes right off again and my wife my wife touched me she goes why are we taking off again and i'm looking around and it took eight minutes and i was like what is going on i put my shoes on i'm like if there's a attack like we're gonna get ready i was like getting starting to get really nervous you thought there's like an animal on board the israel plane thing had just happened and i'm like we got to get ready i'm like i'm gonna get ready i'm gonna get ready i'm gonna get ready i don't know what's happening and then the guy's like okay so our brakes went out and i had to make the last minute decision to take off again um we have to go to salt lake city now now don't freak out because planes have multiple types of brakes i'm going to do like a reverse thruster and when we land there's going to be a lot of fire trucks there don't worry it's probably going to be fine and that was my next 45 minutes and i still did a drug free but that was literally
Speaker 2ladies and gentlemen we heard sam thinks that he's we're just going to quickly test
Speaker 1this yeah who's locked in with who bitch
Speaker 2dare this bitch dare me to reverse first land. So I freaked out a little bit, but it totally worked. I feel like that method works for many more things than panic attacks, right?
Speaker 1Yeah, I think that I saw this great. I've been really I was I've been trying to work with this panic thing for claustrophobia. It's been a huge issue with me.
Speaker 2But your panic is about being locked in that it's claustrophobic or that it's an airplane that could.
Speaker 1It's claustrophobia. So like for years, I wouldn't take the New York subway. And then I started like doing like exposure therapy where I was like, all right, I use Claude and I found the shortest destination on subway. I'm going to go on it just that day. And like I worked on it and like the idea of going on like a cruise ship and being up in the middle of the ocean. I that is like the worst thing on earth to me when I hear about that. And so I've been working on this. And so I was like studying like fear and panic and how to get used to it. And I saw this really cool video with the coach of did I tell you about this George
Speaker 2St. Pierre? I don't think you told me about this video.
Speaker 1A lot of sort of like investors, a lot of MMA coaches who you'd expect to be these like big meatheads. And many of them are. They're really philosophers. They're like philosophers a little bit. They're like really into this stuff. And the reason they're into this is because getting in your underwear and going to like kind of fight to the death in front of a million people, that's a very traumatic, scary thing. And so how do you prepare yourself to do that? And so they start to study this stuff about fear. And this guy, I forget his name, but he's a hobby or yes. Yes. Is that the Arab guy from Canada? He's cool. He's very thoughtful. He's great. He comes off like a philosophy guy, but he's a coach for MMA. And George St. Pierre, one of the greatest UFC fighters of all time, also a very academic-y sounding person. And he was like, you know, George doesn't like to fight. Like he doesn't like to hurt people, but he loves training and, you know, he got good. And so he kind of came to his career, but he didn't like to fight. And frankly, he was very fearful. He was not this guy that was like Conor McGregor. That's like, I cannot wait to get into combat. That wasn't George. And so what we did to make him less fearful is months leading up to the fight, we would start training the actual day of. So he would eat the meal before training that he was going to eat that morning before the fight. But then we would take it a step further. We got UFC gloves, so not like practice gloves. He would wear the exact ones that we thought he was going to wear. He would dress in his UFC outfit. And then also before he would train, we would have the competitor's walkout music play. And then we also went and got these huge lights that we'd, put around the octagon. So it felt the same heat and the same brightness. And so he could start getting used to these jitters. And I was thinking, I was like, it's kind of interesting that they do this for like the scariest thing on earth. But when I have a hard conversation, like I have to fire someone or something, oftentimes I'm going through that motion unprepared, meaning in my head, I've sort of thought about it. And I was like, next time I'm like going to actually do like a yuppie corporate thing that I'm fearful of a negotiation of firing, having a tough conversation. I'm like, the next day I'm going into that conference room, and I'm literally going to do like the walkthrough of exactly how I feel. And I should do that for everything I feel. And so in preparation for this flight stuff, I found myself like, occasionally I would like actually pack my suitcase or I would like go through the same motions. And I'm like, this feels silly, but like, it does feel nice because this does make me nervous when I'm packing for a flight to get. And so it was really useful to hear his perspective on how they would get down to the very granular details of the fight and replicate it. So your nervous system was used to it.
Speaker 2That's really interesting. There's also probably a, sometimes you really anticipate events. Like let's say here's something you're excited about. You think something's going to happen. And often the anticipation is more than the actual thing. And it kind of leads to disappointment. You see this often with founders who sell their company or, you know, achieving something and the, you know, and then you kind of, almost the anticipation was more, more exciting. And this, and science has studied this, that actually the peak of enjoyment comes in the anticipation lead up to the event, not the event itself or the aftermath of the event.
Speaker 1I feel that way whenever I buy anything, like when I'm the three months that I'm researching, buying a new car or buying like a winter coat, I love it. And then I like get the coat and I'm like, oh, okay. Like, you know what I mean? Like just buying even the smallest things. I anticipate it
Speaker 2so much. What happens is rarely does an on a high anticipation event, rarely does reality match the high. So this leads to disappointment when it's something you're excited about. Now, when it's something you're dreading, but it sounds like you're allowing the anticipation to happen in a big way beforehand. Well, then when the real thing happens, it's kind of dull compared to what you anticipated. And it almost blunts the effect. Just it's kind of like using the thing that disappoints you on something you're excited about. Well, with something you're scared of, you use it to your advantage because the real thing is actually less scary, less, less novel, less has less stimulation because you've spent the time in the anticipatory state. I mean, my guess is that that has something to do with it.
Speaker 1Yeah. Because all the things leading up to anything that you're fearful, love contribute oftentimes just more, you know, as much as the actual nervous thing. So like, uh, when you're laying in bed the night before you have to have a difficult conversation, oftentimes that part is more miserable than when you're actually in the middle of it. I used to run track and field and we run these races and it's not like the UFC and that you get beat up, but it's the same thing where you're like, even if I do good during this race, I'm about to go through pain. All my friends and family are here. I don't want to be nervous. I don't want to embarrass myself. And oftentimes in the middle of the race, you're not fearful at all, but leading up to it, you freak out.
Speaker 2And the weird thing is, uh, if I think about like the scariest thing I ever did is probably, probably the scariest thing I ever kind of signed up to do was skydiving. I wasn't really scared going into it again, mostly because I didn't really, I didn't really care. I didn't really think too much about it. But once you start going up and you realize, Oh, 10,000 feet is we're over the clouds. I literally can't even see the earth. Like, and then, you know, my friend went before me and I just saw him go, he just jumps and just disappears. And I don't know, my friend is gone. So I'm like, actually, you know, I'm feeling it when I was up there. And the weird thing is that the antidote to the fear was not really like bravery or getting over it or convincing myself that it's not scary. Like that was hard to impossible for me. It was just acceptance. I was like, I'm like, you know, when you skydive for the first time, you don't do it by yourself. You're all hooked to an instructor. And I was like, you're not getting out of that plane. He's going out, he's going out and I'm hooked to him. It's happening. And just the acceptance of like, well, it's happening. So that, so that part is like the kind of like, do I, don't I, should I, shouldn't I, I don't want to, I'm going to have to, I don't have to do it. It's going to happen. Once I accepted that it is already going to happen that already like neutralized, I don't know, 50% of the fear. And then it was kind of more of what you were talking about. It was like, well, if it's going to happen, then all right, bring it. Let's feel the rush. Let's see what this is. Let's go. I want to, I want this to go. Let's go for it then. If we're going to do this, I don't, I don't want to go skydiving and have to do this or be scared the whole time while I'm doing this panicked. Let me, let me enjoy this because it's happening anyways. And the acceptance was pretty key to like moving past that first emotion to the next emotion, which was not like, not like still, still had fear in it and that cocktail, but wasn't like
Speaker 1pure fear. Well, maybe dare will change your life too. Uh, it's a dismiss my life once dismiss, allow, run towards, engage. It was a great little, a great little thing.
Speaker 2You should just refilm the commercial with the egg, crack the egg and be like, this is your brain. This is my brain on a plane. All right. That's it.
Speaker 1That's the pod.
Speaker 2All right. Let's take a quick break. I want to tell you about marketing school. It is a podcast that is part of the HubSpot podcast network, and it is run by Neil Patel and Eric Hsu. And these guys are both marketers who are running businesses. And so if you want real world tactics from practitioners who are actually out there in the field doing it, this is the podcast for you. Check it out wherever you get your podcasts.

Podcast Summary

Key Points:

  1. A retail investor who sold his company for eight figures achieved a roughly 22% annual return over about a decade while averaging only 2.9 buy or sell decisions per year.
  2. He owned around 15 stocks, made zero decisions in three of the last 10 years, and beat the S&P 500 in 11 of 12 years, with 2022 as the only losing year.
  3. His method is to study a few businesses he understands deeply, keep detailed notes, and wait for the market to offer a cheap entry point before acting.
  4. Successful investors and founders tend to make very few decisions, avoid agonizing over reversible choices, stay within their circle of competence, and write down ideas and pre-mortems.
  5. Jack Dorsey wrote "140 Reasons Why Square Will Fail" before launching Square, and Mark Zuckerberg seeks candid input from smart people while accepting big, high-conviction risks.
  6. The DARE method (Dismiss, Allow, Engage) helped one host overcome 15 years of flight anxiety by welcoming panic rather than fighting it.
  7. Rehearsing feared events in granular detail, as UFC coach Firas Zahabi did with Georges St-Pierre, desensitizes the nervous system and reduces fear.
  8. People should identify which "game" they are playing, since games shape what you want and who you must become, and most people never consciously choose theirs.

Summary:

This episode explores the power of making fewer, better decisions and how top performers manage fear, risk, and motivation. The hosts open with a retail investor they met in Hampton who sold his company for eight figures and then earned roughly a 22% annual return for over a decade, beating the S&P 500 in 11 of 12 years. Strikingly, he averaged only 2.9 stock decisions per year, owned about 15 stocks, and made zero decisions for three years. His approach is to study a handful of understandable businesses deeply, keep detailed notes, and wait patiently for a cheap entry point.

The conversation then draws parallels to Warren Buffett's "lethargy bordering on sloth," Kevin Ryan's one-good-idea-per-year rule, and Jack Dorsey's pre-mortem listing 140 reasons Square would fail. The hosts contrast investing, where avoiding mistakes is paramount, with entrepreneurship, where big swings can pay off enormously, citing Mark Zuckerberg and his acquisition of Alexandr Wang's Scale AI. They also discuss the DARE method for panic attacks, exposure therapy, and Georges St-Pierre's fight-day rehearsal routine. A recurring theme is identifying which "game" you are playing in life, and the episode closes with motivational ideas about staying in motion and keeping your sails up during hard times.

FAQs

He averaged only about 2.9 decisions per year and made zero decisions for three years in a row (2022–2025).

He studies a few companies he understands deeply, keeps detailed notes, and waits patiently for the right opportunity, often for months.

It means making very few decisions and being extremely patient rather than constantly trading or taking action.

A pre-mortem is writing down everything that could go wrong before starting. Dorsey wrote '140 Reasons Why Square Will Fail' before launching Square.

By rehearsing and mentally experiencing the feared event beforehand, the real event feels less novel and less scary when it happens.

DARE stands for Dismiss, Allow, Run towards, and Engage—acknowledging the panic, letting it happen, and then refocusing on a new activity.

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