And I was like, "What have you been doing?" He's like, "Well, I actually I'm a public investor. I'm I'm a um I invest in public stocks."
You're like, "Oh, you lose money for a living."
Yeah. 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, um, 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 in in money after he sold his business. And I was like, "What have you been doing?" He's like, "Well, actually, I'm a public investor. I'm a I'm a um I invest in public stocks."
You're like, "Oh, you lose money for a living."
Yeah. I was like, "I'm pretty nosy. Do you have your laptop on you? Pull up your brokerage account right now." And he did. And we like I was looking through his whole brokerage account and I want to show you his results. But basically he's had a nearly a 22% annual return for the last decade which is amazing. But that's not the interesting part. I uh 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? A 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 uh three out of the last 10 years, he made zero decisions and at most he made six decisions in a year.
So let me let me let me just read the kind of because this is a great this is a great graphic by the way. So if he had put a $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 3 years, he did nothing. That was the longest stretch of of no activity. That was 20 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. Uh, and that was 2022. And basically, if you were to invest around $10 million when he started, I think 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 I sound very smart when I preach this, but you know, you and I are very similar. We we move a lot and we often times 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.
What, by 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?
They weren't obscure. Um, one was a very I don't want to get reveal too much of his info, but um, one was a very large travel stock. So like imagine a popular airline or something like that. Another one was a was a popular clothing stock. It wasn't Lululemon, but imagine like a Lululemon, things like that.
And and so he was do when you say, you know, he's got four months of thinking. Was it actually four months? Like was he just sitting every day and doing research basically? Was he is 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 would hear something or learn something and decide to make a change?
So 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. You know, 2.9 decisions a year. What are you actually doing? He 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'm learning the annual reports and I keep an eye on it and then when the market um presented itself and the opportunity presented itself and it got cheap enough I bought it that day."
So he is he is doing the Buffett thing right he's basically spending every day learning and then when there's a a moment moment in time going ahead making a position were you what what surprised you the most was it the number of decisions what else what else surprised you
a few things surprised me the first thing is you know we love having investors on here from Howard Marks um
and we're not investors uh not exactly you know 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 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 like you can go back in time and like fix something because you can kind of build it on the fly a little bit and so I'm very fascinated by this and there's this cool quote it says um it's by Warren Buffett he says his investment strategy is lethargy bordering on sloth that's like the cornerstone of his investment uh thesis which I thought was interesting and I was like that's so fascinating and we had Kevin Ryan on the podcast. Uh Kevin Ryan is a guy who owns sort of like an incubator uh a startup lab. I don't know how you describe it but they've launched a handful of like tens of billions of dollar 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 which isn't. And for the ones that are reversible, don't sweat over them. Don't agonize over them. I actually think you 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?
Yeah, I do think I I do think I do that pretty well. But it's because on 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 Perbry, Morgan Howell, Kathy 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.
My 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 opposite 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.
My nature is the opposite which is I tell myself well
like the way you do one thing there's all these like cute phrases we tell ourselves 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. Yeah. You're you're just a mess. And so that tends to like tell my like 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 I was 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 argument. 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. Often times you'll notice people write premortems. Have you heard of a premortem where you write down everything that can go wrong? Like was I still happy? I you don't want to do this thing called resulting where you say 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'll do things like premortem 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 who is he's a retail investor who's outperformed the market.
Have you heard of the Jack Dorsey premortem he did before he started Square?
No. What did what did he do?
So Jack Dorsey had helped create Twitter. You know, I supposedly he 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 you know it's very easy to get high on your own supply and so what did Jack Dorsey do? He humbled himself with a premortem. 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 he gave it to U.
Can we put uh buying real estate on your balls into the Hall of Fame?
Thank you.
You 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 it's it's I'm going to let this one fly.
Yeah, let's that that one that one just uh that won its place in the uh Hall of Fame.
Some farts were not meant to be silent. Let's put it that way. And I decided to let 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 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 uh 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
which feels honestly a little premature because like AI changes every the leader changes every you know 6 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 but the stock agrees that it was a good decision so far.
Right. Sure. Um so he's but he's doing all kinds of stuff. Uh, he's dropping fbombs in interviews now, which he, you know,
that doesn't seem natural. What?
There's two different ones. We could play the clips, but the the first one he's in the backyard. He's he's 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?" cuz remember like
many years ago when he was trying to be trying to be cool and casual and he
outed himself as a robot basically
and he was like I'm just smoking some meat in the smoker and he tried to have like a chilled 4-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 we want.
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 was like the one of the first big data companies for these 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 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 this is why just kissed him on the mouth and he's like this is my golden basically verbally verbally kissed him on the mouth. So they're sitting there this 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 him 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 had made a big bet. I think he put like $60 billion or so. They put 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 had produced nothing on par with the iPhone. So in terms of popularity and and users actually wanting it.
And so he was wrong in that. But when AI came around, he correctly pivoted to it and he said out loud, he goes, "Yeah, this is a type of game where you're not like it doesn't m 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 cuz I won the war. And if you know Zuck, he like loves the Roman Empire. He loves war. He loves his favorite game was civilization. And um if you see even his shirts are like like Latin for, you know, it's always like Latin phrases for like give me Zuck or give me nothing, you know, like stuff like stuff that used to be like about Caesar. And so I I just think it's an interesting idea that's very different than investing of what you 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. Bezos talks about this like with in baseball, the 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 1,000x. It's a 10,000x.
Can 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 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 were describing him as an individual contributor. Are you saying that this guy led a $14 billion 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 saying what he said about him specifically was his strategic mind. So figuring out what should we be doing, his clarative 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 vic 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 pro 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 the way it's organized. So he had these very strong opinions that Zucker believed was the correct answer and that because of that they should go ahead and and and try to pull it off. So that's what he he kind of described as his his attributes of what what it meant when he said he's the guy.
So a leader kind of for sure like leadership ability not not he's not doing all the work.
Another interesting part of this was um is they were ask I think it was on Senra's podcast and Sen was asking him like so how did he know that you were good at those? How did you even meet the guy? How did you even meet Mark Zuckerberg? Why why did you meet? He's like, "Well, you know, Meta was one of our big customers at scale, but he goes, "Yeah, Zach kind of just like does this every once in a while, like every few months, you know, he would uh like he just hit you up and he 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. He goes, he goes, "That's just one of Zuck's like superpowers. He's 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 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 advisers. 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 things."
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 6 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 uh decisions almost in a consensus way, which is very different from the popular belief on how leaders are. Um, and I have noticed that when I have when you and I or I've hung out with like people that are 100 times more successful than I am, often times 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, there's a what's that thing called Dunning Krueger uh the Dunning Krueger 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 and your confidence on the subject dips. Right? And this is why black belts in jiu-jitsu who've been doing 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 are so 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. It's like I'll murder anybody who fights me. You know, like it's like you get that blue belt confidence. Uh 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 they know they're kind of always hunting for anything that resonates, anything that has some signal to and they know it can come from different places and they're they're humble enough to do it.
The shitty part about doing this podcast is I um I signed up for an executive coach and I've like done three or four sessions with them 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. When 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 on myself for feeling that way. Do you feel that way sometimes?
I mean, I try not to, but I definitely feel that way. you know, one of the comparison thief of joy you know, like, yeah, that 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, oh, 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 I don't want to do any of those things. And um, you know, so that's the that's the first thing is like 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 if you ask a normal person or even you ask one of your smart friends, do you think they know what game they play?
No. 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 5 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.
So I want you to I want you to imagine close your eyes and imagine uh a friend who is somebody you respect smart accomplished let's say you 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? They'd be like, "What are you talking about?" Like it would be like shock.
Okay. So, first they're confused. What are you even What are you even really asking me? And then you sort of explain, "Well, we're all playing some sort of game." And maybe uh 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, Jaylen 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 this, 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 they made a mistake trading me away.
And most of the NBA players that 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.
Yeah, 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 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 multi-millionaire was, I think, both of our goals. Hence, you know, part of the spirit of this podcast, why it works, cuz 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 game do you think that person you were thinking about is actually playing? Probably 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.
And what's the why on that?
