This guy made $80M in profit. Here's his next 3 stock picks

0:00 The world is still unsure about how this is gonna play out. I'm not unsure. I'm willing to bet it all. I feel like I can rule the world and no way Be what I want to I put my law in it like my day's all. On the roadless travel, never look back. Chris, good to see you again.

0:18 Hey Sean, how you doing, man? I'm good. So we should start with a little bit more. A little intro. Sam, you weren't here last time Chris was on. Christine you do like the

0:27 the the simplest explanation of Who you are, number one, and then number two is your kind of unique philosophy and unique strategy that you've used to buy you know buy and sell stocks to invest. Yeah, I mean I'm a re I'm a regular person for most of my career. I've had a regular job. Uh, I'm not a financial analyst. I'm not a technical trader. I hate all that stuff. I hate technicals, I hate fundamentals.

0:52 I'm like most regular people, right? Like a normal guy with the normal job that was trying to break out. You know, try to find a future for myself because I realized that my job was capped, like 99.9% of people in this world. And You know, I started investing something I call observational investing or social orb investing, which is uh really all it is is trying to detect change in the world, whether it's change in technological development or change in culture, change in consumer behavior. You're trying to detect change. And you're trying to connect that change.

1:27 uh connect the dots to companies that would either benefit or be harmed by that change. So you're And then you're investing in those companies. It's it's that simple. one of many of ways that you personally observe is through social media comments. Yeah, I mean like think about it like

1:43 How do you observe change in the world the quickest? What do people do before they change their life. They talk about it, right? Before you can see the evidence of it. They talk about it. If you're a developer. And and and you're changing the way that you develop software and you're you're adopt AI in your company. You're probably in Reddit forums with other developers speaking about it.

2:06 And it's not always tech. A lot of it is just consumer behavior, right? Because uh I remember you had one that was around the sphere. Which most people don't even realize. That's the the big the big dome in Vegas, the sphere. It's a publicly traded stock and I think you noticed what was it, the Wizard of Oz? You were like Dude, this Wizard of Oz show Yeah, game game. Game changer, right?

2:28 They didn't quite nail product market fit the sphere until that Wizard of Oz came out and they're like Oh, take an old movie. Use AI to make it more interesting in terms of visuals to put it on this insane projection screen and then add some 4D effects like a tornado and the winds blowing and all this stuff. And all of a sudden you created a unique human experience that would go viral on TikTok, which is exactly what happened. And now people from around the world from Europe are like we're going to Vegas to go to the sphere place to see this

3:01 The wizard of Oz that we saw w went viral on TikTok, right? And so man, what a game changer. Did you buy it? Dude, yeah. So I I heard him talking about it. So I started tracking it. It's up two hundred twenty percent. I mean from the time we got in, which is like at twenty something bucks, it's up like six X or something. Chris, uh y I gotta give you a little credit, because anytime somebody comes on the pod and talks about investing, the goal is first to get context on Okay, before we listen and and really drink the Kool Aid on all the your philosophy or your strategy, we like to understand

3:32 Does it work? What what are the s what are the results? And so you could talk a little bit about that, but I'll give one A little point which was last time you were on the pod. I asked you to make three Sort of.

3:42 Picks. Three predictions, three three stocks to look at. You said Palantir, Bloom Energy. It was at ninety two dollars. It's now at two hundred forty. So it's up a hundred sixty five percent since the last podcast. And then NVIDIA, which is up. A a smaller amount, but those are your three picks. So I gotta give you give you a little bit of credit. So here's the thing, like I d actually aggressively disagree with that type of performance.

4:04 analyses because the world's changing every minute of every day. So like the day after the show, I could have found new information that would have put me on the opposite side of all three of those trades, right? And so the only way you could ever analyze Any investor. Ever.

4:22 is through long term audits. over a long period of time total portfolio. I don't care if an investor comes on, gives you five stocks and all of them rocket. It could have been based on beta, could have been based on the m like it Completely luck, right? Uh, so don't give me any credit for anything from the last show. If you don't want I mean you feel free if you want. But all that actually matters

4:45 is what's like the 10, 15, 20 year total portfolio track record in and out through multiple markets. Great. W so what is it? What are the audited, what is it, fifteen year results? It's like sixty eight percent over s over sixteen, fifteen or sixteen years. What does that mean in terms of dollars? What'd you start with?

5:04 I generated about eighty million off of an initial twenty thousand dollar portfolio that I kicked off in two thousand seven. Wow. And then do you reinvest new capital into that? The truth is

5:17 That I took massive amounts of capital out every year, almost all my profits. And so theoretically if I kept it all in and maintain the same returns Which would have been harder because the account would have been larger, obviously. It'd be like at seven hundred million or something like that. Um, but you know, the truth is it's meaningfully easier to manage an account that is seven to eight figures than an account that's nine figures for obvious reasons, right? So you can never really compare Apples to Apples. You can't really compare me to a guy managing five billion. It's unfair to the guy that's managing five billion because he has

5:57 restrictions, he's having to move large amounts of money. I'm able to be hyper flexible with what I do. But I would say that the sizing of my account is still meaningfully larger than just about any other retail investor in the world. What's been the worst downswing? W uh what year did you do the worst or what's what's been the biggest dip you had? I think I ha I'm it wasn't crazy. It was like thirty percent down, twenty or thirty percent down in a year.

6:23 I think the biggest up years might have been like three hundred percent in a year. So but it's been Relatively. Relatively consistent. So Chris, I want to ask you a question. After you came on and you talked about this observational investing and I have to say I I I

6:38 obviously was I'm a bit skeptical about most financial influencers on YouTube. I would just say like that's just a general stance I have. You should be more than skeptical. Yeah. So so uh but but you know, when you what you talked about is didn't It's not like it was some uh insane idea. Like you look for changes of where where you see the world going, where you think demand is going, where there might be supply constraints, and those obviously might be interesting companies. Now, the question I have for you, because one one example is uh my kids went crazy about these things called Nitos. Explain what these things are. They're basically just the Pile of it's just like a goop ball. I don't even know. What do you mean explain it? It's just it's just a squishy toy. It it it's a squishy toy that is slightly firmer, slightly higher, uh the squishies have been around for fifteen years. Uh, but they were able to go viral this last year. It became a thing in kind of elementary and middle schools of like finding rare nidos. They you couldn't find them. So they had that sort of like

7:33 That Pokemon card. This happens a lot of times with crazes, right? But is Nito a public company? Yeah. So so Nito is a very tiny private company. That's actually held by another private company that owns I think twenty seven private companies and Nito, the company that owns Nito is one of those 27 companies. What's interesting is that this is a holding company. that generally doesn't move because they generate their earnings.

8:02 From interest payments. And dividends paid by these small operating companies. To my knowledge, and the ticker is G A I N. To my knowledge, they've never owned a company that has had a hyperviral product like NETO before. Can you imagine that uh Wolf of Wall Street call to Sean like Lass ihn schon. This is a small company in Andover, Massachusetts that is sitting on breakthrough technology that is extra squishy yet firm at the same time. That's exactly what it is, man. That's literally exactly what it is. And by the way, whenever you invest in a tiny company like this There's all types of unknown risk involved. Uh so it's a really dangerous game to play, but I did make the investment.

8:46 It's a bit of a novelty investment and a novelty product. So I m the thesis is that if the c if Nito can remain on trend through the holiday season, and if the parent company is able to fully scale out supply. this is actually going to be a needle mover for the parent company. to the and and you should see about a thirty to forty percent increase in valuation at the parent company.

9:14 trade even further. There's always cool books on like uh you know Warren Buffett's first like fifty deals or whatever. Let's do uh Chris's uh investment in the Nitos. Could you say how much did you put into it? When did you put into it? And like when you're saying there should be a thirty or forty percent, what numbers did you look at to make this estimation of what how much juice is on here or how mu how much profit it can could be had. Y you're basically looking at

9:38 Hey, let's take a quick break because the team at HubSpot has put together something pretty cool. You know, in this episode Chris is talking about the way he knows how to make money. Identifying these trends, scouting the TikTok comments, making these big Leverage bet. That's great for him. It is amazing. Some people will like that. I personally don't know how to make money that way. I wouldn't do it. But I've talked before about the way that I know how to make money, about how build a money making skill, about how to leverage your time and energy. And the team at HubSpot actually went through the video where I explained all that.

10:04 And turn it into a free downloadable cheat sheet on my four rules of how to make money. Now. This is not, you know, give rich quick advice. It's just core principles, foundational principles about building wealth. Things that I wish I knew when I was, you know, just getting started. And so if you want to download it, it's in the description below. It's totally free. You can go get it. Thanks to the folks at HubSpot for doing the research, making this document, and making it available to all you guys. All right, back to this episode. You're basically looking at how many Nitos you think the company can sell. through the holiday season.

10:35 based on demand and how many they're currently selling. By the way, this is like a little bit of a science and a little bit of an art. And and you kind of assess what that will do to that company's bottom line. how that will increase dividends and what that increased dividend payment to the parent company will account for relative to the total valuation of the parent company. It it it's it's it's kind of a difficult exercise. And this is where AI comes in really great because AI can help you do that exercise. So we're you know we're not financial analysts and

11:09 A I doesn't excellent job going deep into the financials of a company like this. And then like, okay, if they sell this many at this much of a profit margin, it could have this big of an impact on the parent company and of earnings come the holiday season. So again, lot lot of estimates that you're making. It was enough for me to invest. I put like It was somewhere between half a million and a half and a million dollars into the trade. It wasn't crazy.

11:36 I did it more because I love the product and I love the trade and I felt the trade's going to work. And I wanna be part of it. So like for me On an equity trade, that's not a huge trade for me.

11:50 But I like it. And and by the way, if you look at the past Seventeen years. I've made about Maybe. to eighty five high conviction trades over seventeen years. So

12:01 The entirety of my performance is based on those eighty trades. And Nito was a high conviction. I wouldn't call Nito a high conviction. I call probably a medium conviction because the company's so tiny. That there are a lot of variables. that could impact a a minuscule company like that.

12:21 But Um, all eighty of those trades were publicly discussed. more or less as they were happening. So I'm really public. with my ideas because I I want my community to kind of provide feedback and poke holes in my thesis.

12:38 You know, there aren't that many of us social arb traders, observational traders. So I've always said that the community at large when we work together on ideas. Sometimes I surface ideas. Sometimes members of my community surface ideas. We cross research them. Advocate with each other.

12:58 We poke holes in the thesis and I always say as a as as a group We're more powerful than the biggest hedge fund because we have you know, tens to hundreds of thousands of people now that are social orb traders. And we come from every walk of life. So we have people from every industry sector, every profession, every demographic. So we have tons of people that have kids. When we do channel checks, when we do store checks

13:23 I'll throw it out in my community. And they will pe they will do store checks in every state. So we'll have people aggregating, hey, I went to this shop in Missouri, I went to this shop in Florida. Here's what the clerk told me, right? It it's really, really fun, guys. Now let me ask you a question about this. The specific question I have is observing the trend. Especially if you're a a parent with with young kids. W was actually not that hard. It was pretty easy to see Holy shit, every kid in the school wants it and there's none on the shelves. Uh they can't f the you know, stores can't keep'em in stock. People are banging out the door. So the buy side of that kinda makes some sense to me. But all these things seem like Fads they seem like trans.

13:58 I would never know when to exit. A trade like this. I would never know when to sell because I don't I don't think twenty years from now My kids are gonna care about Nitos or the kids aren't necessarily gonna care about Nitos. So can you explain how you think about the The exit or the sell when it's come when it's something like this where it's like a trend or a a wave that may not be enduring. Well well let let's back up. It all it all is dependent upon the conviction level and the underlying thesis.

14:23 that you observed, right? So you you have a thesis that you come up with that there is some new information that is likely to positively or impact this company or this sector that the market is not aware of yet or that the market underappreciates. Now you have to ask yourself To what extent is this a needle mover for this company?

14:49 Right. Is this going to meanfully move the revenue needle, the profit needle, their cost structure, or the perception of this company. Is it meaningful? And are there other things that are happening to this company that are more meaningful than this one piece of information that I feel is a needle mover. Okay, and then you have to ask yourself to what extent. Do other investors institutional or retail already know about this. Because it's not a binary thing, right? Some people might know, but does the market at large

15:20 Fully Appreciate that piece of information, or do they only partially appreciate it? So it's additive. And you have to determine

15:32 Am I highly convicted in this trade because this thing that's about to happen or that already happened is going to be massively impactful to this company, and there's nothing else. that's going to impact this company over the course of the next few weeks or the next couple of months. And There are virtually no other investors in s institutional or retail. That

15:55 Understand this yet. And to answer your question, Sean. The exit window is when other people come to terms with this information, right? When other people start to appreciate this information that you found.

16:11 that you traded on. As soon as that information becomes public. Like in the case of the sphere. When other retail traders When financial press

16:22 When the company itself and analysts started coming out w reports saying, Hey They're selling out the arena. due to Wizard of Oz. This is going to be a game changer. We're starting to revise our earnings estimates based on this new template that they found with the Wizard of Oz. And by the way, they can replicate this model now with other old movies. And it's a high profitable model and we now feel That they've kind of cracked product market fit at sphere, which is a game changing moment. When you start to hear about that in the press, when you see other investors talking about it on X, when the company itself talks about it, that's the point of information parity.

17:06 And that's when we exit the trade. So you basically initiate an observational social orb trade. at the point of information imbalance, when you find some information that is impactful that the world doesn't know about yet. And you exit that investment.

17:24 As the world starts to appreciate that information. And that's not always a binary event either. Sometimes you exit it over time as more and more investors start to appreciate the information. Now You try to ignore stock price. The assumption is That if that piece of information is meaningfully positive to that company.

17:45 As other people start to to to to surface that information that it will possibly impact the stock. But that's out of your control. The bottom line is you're trading a thesis. Your thesis

17:57 revolves around one piece of information. And when that information gets widely disseminated to other investors then you no longer have an information advantage. Therefore, you should be exiting that trade, whether you made money in the trade or whether you lost money in the trade for some other unknown reason, maybe the market, maybe something else happened, is kind of irrelevant. So that's the entire methodology.

18:24 That's everything I've been doing for seventeen years. There's a lot more to it. Because like when you find this narrative Right. You then need to like check every other piece of information that you can or data source.

18:37 To validate it, talking to store clerks, right? Maybe you're pulling web traffic stats, maybe you're looking at Google search trends. Depending on the trade, there's a million different ways to validate The narrative thesis that you originated Using alternative data or other information sources. It's just it's a case by case basis.

19:00 But this is everything I've been doing for seventeen years. And it's very different from being a fundamental trader. Or being a technical trader. Has there been a time over the last fifteen or eighteen years that you've been doing this where you've said, I'm quitting and I'm uh I'm not doing this anymore, I'm going back to like Just index investing or something like has what what was the low point? No, I love this so much, guys. This is literally part of my soul. This is what I do.

19:25 I I have so much fun doing this. Like you gotta realize like My methodology entails reading comment on TikTok videos. I get to watch the world unfold. I get to learn about culture and consumer behavior and trends and what people are buying, what they're doing. It is the funnest research any investor could. ever do. I'm not studying fundamentals or charts.

19:48 What I do is fun as hell. I then every five years I have this thesis that I go all in on. So five years ago it was Pokemon and Nerd Culture. And I started this company called Collecticon and we became The largest Pokemon trade show in the world.

20:06 And we sold it to Ari Emanuel a few months ago for an insane amount of money, but uh we grew that from the ground up. And I kinda take on one of those projects. The next project I'm taking on Wait, can we t tell me about this. Tell the tell the full story before you tell new project. Oh you wanna know the story? I i i this is actually amazing. I always tell everyone Don't do things

20:32 For yourself. Just go out there and do things for other people and it always comes back. in your favor. Don't ask how or why. It just generally always does. So I'm really big into philanthropy. I have a five O One Foundation. I support

20:47 pediatric charity, animal welfare and elder care. And back during the pandemic. I know nothing about Pokemon, okay? But Logan Paul bought like a three hundred and fifty thousand dollar Pokemon box, which is the set the world record. And

21:02 I was like, man, that looks really fun. And I was kind of bored. I'm gonna go do the same thing. But then I'm gonna break it into like the twenty four packs and auction it off. for charity. And then just donate it.

21:16 all to the foundation. And I'm gonna also throw the world's biggest Pokemon party in Vegas because I ended up meeting all these Pokemon people and they were the coolest, nicest people in the world. I'm telling you, I never met people so fun. And so I met Steve Aoki, who's a big Pokemon guy. I met this guy, Gary King Pokemon, who's the number one Pokemon guy. collector in the world and he was the guy that I think sold Logan. One of his biggest Pokemon cards. And I said, I wanna do this party, guys. And they helped me put on this party in Vegas and we agreed

21:47 That a third of the proceeds would go to S Steve Aokee's brain charity. charities, like whatever. A third would go to Gary King Pokemon's autism charities, and a third would go to the charities I care about. So I bought this box for three hundred and seventy five thousand dollars. We broke it up through the world's biggest Pokemon party. Donated hundreds and hundreds of thousands of dollars to charity. The party itself.

22:14 Cost me Almost a hundred and fifty thousand dollars to put on. I made zero. All this was a massive loss and donation to a bunch of charities. But what came out of it?

22:28 I met all these really interesting people. And about a month later, Gary King Pokemon calls me. He goes, Hey Chris, I know you believe in Pokemon now. I know you believe that this is gonna be really big and get bigger every year. One of the guys at the party wants to start a Pokemon convention. And he doesn't have any money.

22:49 Can I introduce you? Maybe you would invest in it. Yeah, sure, let's do it. I had lunch with this guy. He lived in Texas. I said, let's just do it. This guy's been working in in like conventions for twenty years. He had the perfect skill set to do it. Him and his two cousins were Deeply passionate. collectors and Pokemon collectors.

23:09 I said you guys are the perfect People. To run this conference, лес до Гер. I invested Uh I want to say six hundred thousand dollars.

23:20 Into the company. I took a minority but massive stake in the company. And I help build this conference starting with one show. In a small hotel Convention room in Frisco, Texas.

23:35 And Four years later. We were throwing twenty shows Seven hundred thousand attendees.

23:44 Biggest Pokemon trade show in the world. Massive success. And by the way We all worked all the shows. Like I would travel around the country And be the guy who was ticketing people online at seven in the morning when we'd have three thousand people in line because We were trying to operate the show so efficiently because we didn't have much money. Massive business, guys. Massive. You wouldn't believe I I'm under NDA. I can't tell you the specifics of the sale.

24:17 But massive exit. Can can can you say generally speaking, these businesses, what do they sell for? Uh not Yeah, like uh like on EBITDA like what what's the EBITDA multiple. They don't sell for big multiples because it's a it's a physical business. It's not like a software business. But the amount of money we were generating from these shows was enormous. It was really profitable. Very profitable because we care deeply about the shows and we ran great shows. We actually

24:51 back of the envelope math, seven hundred thousand times let's say sixty bucks, that's you're getting close to fifty million dollars in revenue, let alone vendors. I can't disclose exact numbers, but I'm gonna tell you the numbers were huge. And we started from nothing and we built this all up over four years, but it wasn't easy, guys. Like we we were so frugal. That we had our own rig because you know the most expensive part of throwing a convention is buying renting pipe and drape at all the conventions. So we bought our own pipe and drape.

25:20 Put it in a eighteen wheel. And The founder operator of this business, Matthew. would drive the truck himself from city to city. It was crazy. Okay? And

25:32 And then we would unload the truck with some local help, right? And we would set up the shows or I mean there were points Because I have a bad back. Where after the first day I was almost I couldn't walk. And I s there were some shows I'd have to go home on day two'cause I I I hurt my back so bad from just like

25:52 leaning over ticketing thousands of people at the at the show. Cause we would hire contract workers to help us, but we needed every hand possible. That's pretty cool. And so we ran it like a family business. We were deeply passionate about the attendees. We would throw a concert every Saturday, midday. We had like Vanilla Ice would perform or like It was so fun. And and meanwhile, to this day I've never bought a Pokemon card.

26:18 So like I was an observer of this sector. But the long story short, like I had deep conviction. In nerd culture. And Pokemon specifically.

26:31 And I think Wall Street doesn't and just business the business community generally doesn't appreciate the fact that there are millions of people That like collecting these cards. And no one had provided

26:46 A fun place for them to physically go to once a year to connect with other people like them and trade these cards. Like we have sports card shows. We've had them forever, right? With baseball cards and whatnot. But no one had ever really established a big show. for T you know TCG for like these table card games, right? Like no one had ever done it before. So it just intuitively made sense to me. 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?

27:18 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.

27:38 So I'm curious. If this is something that others have been doing or the people you look up to. So for example Somebody who you wouldn't think is an observational trader wouldn't call that is Warren Buffett. But there's some great stories of where he did exactly what you're talking about. There's a

27:54 a story of the salad oil crisis with A American. I don't know if you guys know that story, but it's basically Yeah, at a at a given time they're lending money. And they were lending money to this guy who's supposed to have salad oil dressing. And then they went and they checked the barrels and the barrels were just full of water. Salt water. Like seawater. And there was no salad oil at all, and the stock is plummeting.

28:15 And Buffett he figured out what the central question was, which is is this a temporary setback or is this actually gonna be damaging to the trust of the brand long term? And he uh believed in brands, right? That's why he has been on Coca Cola and Gaico and these other companies that he feels like have uh brands that have power. It's the exact opposite of what Chris is. It's of like what won't change. Yeah, so he well, he was but still the the the market research part of this is kind of shared, right? So he the the story is he goes into a store.

28:43 And he just watches the clerk and he watches customers with their credit card and he's basically trying to figure out Are people gonna stop taking American Express because they no longer have faith in the good standing of American Express? Or is of the American Express brand gonna withdo endure this? And really the asymmetry was The market believed that The that

29:03 This would damage the future of American Express, uh, and this the quality of the brand. And what he observed in watching people was that The stores and the customers had no problem using American Express and that there was no there's no issue. And he did the same thing. He did this very similar thing with Apple, where he had l stayed away from technology companies for a long time and then he realized like oh When you talk to Apple customers, he's like not only Would they not? trade their current device for a cheaper

29:30 equivalent of device by somebody else. You can't pay these people to switch off Apple. And it it was the it was a more of a social psychological observation, not a technical or fundamental analysis of the business that led him to to to invest in those companies. So Chris, but it's a long winded way of asking, who else has been great at this? What are the great stories that inspire you on this, or do you feel like you're kind of The first one to popularize this. No the concept of information asymmetry is not new. to investing methodologies, the most famous person to adopt it widely would have been Peter Lynch.

30:04 With the Magellan fund in the eighties. The difference is Being a pure observational social orb investor Is this concept that

30:16 It shouldn't be part. of an investing methodology, but it should be the only thing that you take into consideration, right? So Peter Lynch kind of blended. This

30:28 Famously walk the malls. and kinda look at what stores had the longest lines at the cash register. Seem seems pretty simple, right? And he would

30:41 Combine that With massive amounts of fundamental research. You have to ask yourself though. If the market is relatively efficient, and we know the market's never

30:53 Perfectly efficient. But it's if it's relatively efficient. In terms of taking into account all the fundamentals and all the technicals, and you have all these investors that are trying to price a company based on all the known things. Then if you're able to surface something that's unknown.

31:15 That is meaningful. You don't need To worry about all the other stuff. You don't need to have this robust fundamental technical approach that also happens to apply information asymmetry when you come across it. You can focus all of your energy.

31:33 And all of your research. On just finding New information that the market hasn't discovered yet. And making an assumption. That

31:44 the particular company that you're trading is relatively efficient with all the known information. And investors haven't fully priced in this new piece of information. So All you care about. Is that one piece of information asymmetry? It simplifies the way.

32:01 Yeah. investors can approach this game. Because most of us are never going to be technically proficient investors and never going to be able to compete with the absolute best, most pedigree. Wharton graduated like fundamental investors, right? That are doing t deep, deep fundamental analysis and they've come to terms with the fact that this company should trade at a twenty nine PE as opposed to the twenty four PE it's trading at today. I mean

32:33 I don't want to play that game. The easiest game to play because you can invest a million different ways. So the question is What is the Best approach. to investing.

32:43 that the largest chunk of ordinary people can actually apply efficiently to markets and regularly do that in a fruitful way. And I've strongly believe it's pure observational social arbusting. Sean, I actually just Googled this and it's funny I'm quoted as the source of Google. uh for the story. So it could be a little bit err. But in nineteen sixty six a young Warren Buffett visited a movie theater on Forty Fifth and Broadway in New York to watch Mary Poppins.

33:11 He went with the briefcase in the middle of the afternoon, later joking that it almost felt like he needed to rent a kid to fit in. This trip was his way of researching Disney. To see if they had lasting brand appeal. And later that day he bought percent of the company at four million dollars and it was a fifty percent gain over the next year and he says selling it, which he did after one year, was one of his biggest mistakes that he's ever made. And by the way, so

33:32 Yeah. If he really believed that that lasting durable brand appeal was there for Disney, right? Did he also believe that the the rest of the world came to that acknowledgement after a year.

33:45 And if he did. Then he didn't have any alpha after a year and he was probably right to sell Disney. Um and Disney thirty five when he did that, by the way. So may I mean you could also say maybe just Made a mistake. But you have to understand something. Whether a stock goes up or down after you sell. might have nothing to do with you making a mistake because that's not your thesis.

34:08 That's not why you invested. You don't have any alpha. So it could have gone up for a completely different reason. So y y you gotta get out of the head space. Of saying because a stock continued to go up after you exited, you made the mistake. Mm. That could be c completely coincidental. It went up for something that you had no knowledge into, that you had no take on.

34:29 How do you quantify that though? Because Like, for example, Sean and I or or the average show might have like uh an opinion on one company. Their sales we think are going up. But that doesn't necessarily mean the stock will change. Okay, well let's take a step back.

34:44 If you are correct. That A company is being impacted by something meaningfully. And their revenue is going to go up. And the rest of the investor class.

34:57 is not aware of that yet. If there's nothing else impacting that company during that trade window. It is highly likely. Again, there are a lot of factors. There's the macro market. The market could come down, right? There but but In a vacuum.

35:14 That piece of information W almost always in a vacuum will almost always result in the stock going up because when a company makes more money than the market anticipates. The stock will go up. If you're able to surface something that will impact a company sales that the rest of the market is not aware of,

35:34 When the rest of the world comes to terms. That will positively impact the stock price. Assuming that there's nothing else going on with that company or the market at large. But I I wouldn't overthink it.

35:48 Too many investors overthink this. It's not that complicated, guys. Can you give a sense of volume? Uh so I think you said something like eighty Eighty investment decisions, seventeen years, that does that mean you're making four ish Buy sell trade decisions per year or did I hear that wrong? Because I my my h my hunch was that you're a little more active than that, seems like in a given year. How much how many decisions are you how many investment decisions are you making? So I I'm referring to high conviction trades.

36:15 You know, trades where I have a lot of conviction. And I'm generally Allocating Five to four. Thirty percent.

36:24 of my total portfolio to buying that stock. And I'm allocating call it two to fifteen percent of my portfolio to buying options. And that stock.

36:35 By the way, when you say portfolio, is this like I have my trading my fun my fun slush fund and then I have my boring safe nest egg over here or portfolio. Entire portfolio, yes. I think what Sean was getting at was like, Do you have like a safety net? No. I mean on my pup my public equity portfolio is my public equity portfolio. It's just one portfolio. So when I have high conviction in a trade

37:02 I will allocate between Yeah, like I said, I don't know. Up to a third. of my portfolio might be in that single Stock.

37:11 for that period of time that I'm in that trade. And Sean to answer your question. uh in the early years I would average one to two high conviction trades a year. Uh

37:23 Now As we had more social media today than we had back thirteen years ago, and the world is more digitally connected today. And there's it's actually easier than it's ever been to read into the world's conversations as they're happening. Like as you guys know, I spend hours a night reading comments on TikTok videos because that's

37:45 Where most of the world organically shares what they're doing, what they're buying. You know where they're going, like on a daily basis. I I've increased the velocity of my high conviction trade. So

37:58 There have been years now where I've had Six or seven high conviction trades in a year where it used to be one or two. Right. And by the way. The the more change that's happening in the world.

38:11 The more opportunity to surface a high conviction trade. So probably the biggest year I ever had was during the pandemic because the year of the pandemic, there was a tremendous amount of change happening in the world. We all started living at home, you know, working from home. Right. We we we stopped going out. We started buying things that we would n ordinarily never buy Uh we stopped spending money on those things and started spending money on these things because we're living

38:39 Inside of our house for a year straight. You know, we're buying bicycles and cameras for our computers and printers'cause the kids are doing home schooling and all of these things too. We're buying Peloton'cause we're not going to the gym and we're working out at our house now. So, you know, we're shopping more on Amazon and Spotify. So like The more change, the more opportunity for an observational investor. To surface that change and connect the dots to investable opportunities. When there's not a lot of change in the world, then there's less opportunity for us. So

39:14 Well I what I've been telling people is in the age of AI, we've never experienced this type of global change before other than the pandemic. Because AI is radically changing the way That we think about work. That we think about intelligence.

39:30 Every company in the world is going to get hit. Positively or negatively. A I and and unlimited intelligence is going to impact their sector over the next few years. So

39:45 This is an amazing time to be an observational social arbester. Because the world is changing so quickly. There's going to be so many winners and losers. So the game here Is To figure out what's changing.

40:01 And the degree to which that change is good. or bad for any given company at any given period of time. Does this influence you, Sean? Uh this is your second time talking to him. Are you uh has your actions changed since December? Uh not necessarily,'cause the main thing I do isn't

40:20 Like active investing s uh in in public equities. You know, if I did, maybe uh it would be a little more, but I don't know. I find it fascinating and like you said, we talked to on one end of the spectrum, you know, uh uh sort of the Charlie Monger Buffett Uh disciples. We've had those value investors on. We've had Um you know, Howard Marks, he he's dealing in in uh you know debt and bonds and and you know you have Redalio, you have all these different people. So I'm more of a

40:47 Right now in a kind of curiety mode, not a Oh, great. Let me switch up my style every time I talk to a really successful, really interesting investor, which for us on this podcast is like every month. You but let me ask you a question. Your audience What what do you think the average follower of this show.

41:06 Looks like. Do you think the average follower of the show is capable of being a top one percent Fundamental investor competing against

41:21 Literally hundreds of the eyes. The average listener of the show couldn't be a top one percent in any type of investing. That's not completely untrue. That's ridiculous. I think for the average person can't be that that is that is patently false. Tatly false.

41:39 Where do you think where do you think I graduated in my high school class? Just just guess. For centralise. Either one percent or the first percent. I'm not sure where to guess. But no no no g no genuinely like genuinely I turn I generated eighty million off a twenty thousand dollar portfolio, like Like I I I I am who I am. You c you know, look at the last fifteen years of stuff and articles like genuinely like Objectively

42:05 Like where do you think I would have graduated in my high school class of the public schools? Back up. We the question was The average person of our show, are they a one percent investor? I don't think they are. Nor do I think they are. No, no, no, no, no. I'm sorry. I didn't mean that. I meant do they have the capacity Okay. Well I I'm a I'm asking. So like let's talk about if we talk about IQ, like what do you think my IQ I had an IQ test, what do you think my IQ was or what where do you think I graduated in my high school class? Just just objectively, just throw it out there.

42:35 Middle. Sean? Well, you're asking the question, which tells me it's gotta be in the bottom half of your class. It's lower than that. It's uh bottom twenty five percent of my high school class. I barely graduated. And uh I'll just tell you this. I'm not g I don't

42:52 But I will tell you this, when I was in kindergarten Okay, I was the only kid in the class that didn't know what my last name was. And they sent me to Manhattan to get an IQ test. And I I still have that piece of paper. It was slightly below average.

43:09 In terms of IQ? Nothing crazy. They kept me in the class. I don't know why I didn't know my last name. I'm just saying I didn't I was the only kid that didn't know my last name. I went on to do not a lot better through my senior year of high school, obviously. I was bottom twenty five percent of my class. What about temperament? Because like Yeah.

43:33 again, we've talked to all these amazing people. A huge takeaway that I've had talking to a bunch of the investors in particular is that temperament probably matters more than IQ. And I think the your temperament, the way you were born, is likely just the way it is. You probably can't change it. I think uh Sean talked to Manish P uh Prabhup and he said something I think it was him, Sean. He said something like I probably can't take anyone and make them great, but we could probably improve you a little bit. You know, I think he didn't say this, but it was like the analogy of you're born seven feet tall. And

44:03 You can Be better at basketball at six foot tall, but like You know, freaks are freaks. And so Um Temperament I actually think is probably more important than IQ when it comes to this game.

44:14 Okay, I would say that being a top one percent observational investor just a top One percent investor generally. Is

44:26 Easily doable. If you're willing to aggressively adopt being an observational purist investor. And the reason I say that Is because what

44:39 I actually do is so simple. And so straightforward. And I've seen over the past seven or eight years since I've been public about this on YouTube and I have, you know, hundreds of thousands of followers. I have people around the world writing me near daily.

44:59 They are Dentist. They are janitors, they drive trucks for UPS. They work in a parking lot checking out cars, okay. And they will

45:11 DM me, hey Chris, I've been watching you for five years. I started doing this, I was early to this company. Or to this company based on what I observed in the world. It's that one investment. has changed my entire life. And and I tell people if you have one or two home runs over twenty years

45:32 One or two home runs. over twenty years meaning you find something early And you put a meaningful amount of money in it. that could put you into the one or two percent range of all investors over over that two decade period. And that's all it takes. And a perfect example of that is Tesla. Okay, I actually wasn't early into Tesla. But do you know how many terrible investors otherwise I mean, these are people that hadn't done anything in their entire life in the investing world and probably haven't done much since.

46:02 Are one percent investors because they were behind the wheel of the Tesla. In early days, and they realize this. is a game changer and they put some meaningful, not even that meaningful, just some reasonable amount of money into Tesla stock. And that one investment made them a w top one percent global investor for like a 10 or 15 year period or twenty year period and changed the trajectory of their entire life.

46:28 they're not hyper intelligent. They're probably like any regular person. They're probably like most of the people that watch this show or any other show. And It's all about just understanding that that's all it takes. Because most people never even try this, because I think I can't compete with pedigree of investors from Wall Street. I can't spend six hours a day doing technical trading, they don't realize you don't need to.

46:50 You can just go on with your life. Live your life. Just keep your mind open to potentially Early discovering the next big thing. That's it. That's literally it.

47:00 Like that's all you have to do. Today's podcast is brought to you by my friends at Mercury. Uh they make the world's best banking product. I think you know this already. I use Mercury for all of my businesses. So I think I have like maybe seven or eight businesses. We use Mercury as our business banking across all of them. And now they actually just launched a personal banking account. So I have my personal account there. I moved off of Wells Fargo and Chase. I'm just all in on Mercury. Why uh I like products that are easy to use.

47:25 I like products that get me and the problems that I have. So like very easy to make a joint account with my wife, very easy to spin up virtual cards. Uh, one click and I get savings yield. It just has all the stuff that I need in one place. So If you're looking for the best banking product on the market, it's definitely Mercury. I will fist fight anybody who disagrees with me on that. Go to Mercury.com/slash personal and learn more. Mercury is a FinTech, not an FDIC insured bank. Banking services are provided through Choice Financial Group and column NA, members FDIC.

47:54 W what are the things you have most high conviction in right now? Um My highest conviction trade, I'm like a broken record on this. It sounds so weird because it's not a small company. It's Amazon, guys. Like I I have more money in Amazon, this the most concentrated position I've had. In a really long time. I always say the most concentrated position I've ever taken was Nintendo.

48:17 when they came out with the Wii, because I was at the E three conference and actually saw this like a Buffett story, right? I actually saw the line of people interacting with the Nintendo Wii for the first time. I don't know if you remember that. game changing platform and nobody on Wall Street believed it. Everyone on Wall Street was so hyper focused on the Xbox coming out and the PlayStation coming out. Nobody thought the Wii was gonna be a big deal. I was there, I saw it in real life. I had a hundred percent of my portfolio invested

48:47 in a Nintendo ADR, which is a tracking stock that tracks the Japanese ticker of Nintendo. And I had a hundred percent of my portfolio, I think, for a full year. Nintendo. Until Wall Street finally Realize how big of a deal that was. Uh but Amazon

49:05 Uh I I just think it's the company that is best positioned in the world. to benefit from the upcoming AI efficiency wave, which is Once we actually start to see meaningful productivity. jumps from the AI age.

49:21 uh there's no company in the world that's gonna benefit more from that than Amazon. I also think they are the nucleus of AI infrastructure. So so so sorry, w what's the observation you made here? I I like what w the I is this not from the TikTok comments in this situation? Is this from No th this is this is this is a Kind of a

49:43 global cultural shift. And it's it's a big observation I've had for three years. Which is Based in part I don't know if you guys ever read Nassim Taleb's book, Black Swan. Uh but black swan theory essentially says that our minds are not capable Of fully recognizing

50:05 and appreciating anomalies in the market or the world that haven't happened before. I had this thesis in early days AI. That AI wouldn't just be The next internet. It's not just gonna be the next mobile phone or smartphone.

50:24 But that it would be meaningfully larger than anything we've experienced in our lifetime. And as a result of that We would see the biggest trades of our life happen. Um As a direct result at AI. And even when the information was right in front of us, the market would not believe it until it actually shows up in the numbers because there's no precedent.

50:50 For what we're seeing in AI. There's nothing that has ever happened in our lifetime before AI that we can compare to AI. No. I might regret saying this. In ten years. But I don't think so.

51:05 I think the concept of Intelligence becoming infinite and free to the world. Is going to be the biggest change we've ever seen in humanity. So the reason why Amazon

51:19 went down and has not really gone up as a company meaningfully over you know recently, right? Is because the Have made such an aggressive investment. In AI. Two hundred billion dollar now it's like two hundred and it's more than two hundred billion this last year, uh CapEx investment in AI in a sector that nobody knows if it's going to pay off for them or not.

51:43 Does that mean like um like for example the s did your Siri or what's it called? Uh Alexa, did your Alexa just change Where like now she like talks to like my Alexa just changed. So now it like talks like chat GPT, like I can ask real questions. I would say the biggest example is this, it's it's this simple. Amazon. is betting the entire company

52:03 On AI. End of story. As is some of the other big tech companies, right? They are leveraging all of their profits. They're leveraging their balance sheet. They are building out. massive instrument infrastructure unlike they ever had in the history of the company. They were making the Biggest.

52:19 CapEx investment of any company in the world by a big margin. In AI. And the world is still unsure about how this is gonna play out. I'm not unsure. I'm willing to bet it all. The they think that the infrastructure layer of AI, which is Amazon

52:39 Okay, because Amazon understand this. They are a chip company. Right? They're training them. Their chips alone, their training AI chips are we generating like fifty billion dollars of revenue this next year. They are the one of the largest infrastructure data center companies in the entire world, and their AWS platform and everything that they've constructed in cloud computing over the past fifteen plus years.

53:04 Sits at the center of this. Architecture. uh infrastructure For AI. Okay. On top of that.

53:12 Amazon is the third largest digital advertising company in the world. Okay. So as AI makes advertising meaningfully more efficient and targeted and effective and personal. And rich. For consumers. Amazon is at the center of that wave.

53:32 Additionally, Amazon has spent twenty years building out the world's largest logistical infrastructure for the delivery of physical product humans. An investment that no other company has even come close to making. That investment even moving the margin needle a few points.

53:55 Is a game changer for Amazon. So as we enter this new world of intelligence and automation and robotics. Okay. Amazon already has the infrastructure. as the world's largest e commerce company, the largest logistics company. to benefit massively from the increases in productivity and efficiencies that infinite free intelligence

54:19 And eventually what we're gonna see i i is embodied intelligence, right, with the robotics, right? This is going to result in productivity and efficiency gains unlike we've ever experienced as humans. And Amazon. is the number one company to benefit from all of that.

54:38 Sound like you're giving a sermon. You're bought in. And by the way, they own like fifteen percent of Anthropic, too. They just and that's what's so funny here. Now, if anthropic IPOs between one and two trillion, which who knows, I think there's a reasonable chance they will next year. Amazon will make more money off that IPO than the two hundred billion they spent on CapEx that everybody's so worried about. Right.

55:01 And so again, we are living in an age When the market has more noise. than it's ever had. The stories are changing every day. Like it it's impossible as an investor to cut through the noise. So that's what's so difficult is is I think most new investors, they just give up because they're like, I can't keep up with all this stuff. You don't have to keep up with any of it. Just find

55:26 One company That kind of sits in a place where they stand to benefit meaningfully from something that you're seeing in the world. It could be AI with Amazon.

55:37 It could be The fact, you know, one of my big trades recent, one of my big trade theses recently is flip flops are trending this summer, right? Because last summer there were seven hundred and fifty dollar flip flops made by a company called Roe, and now every person in the world wants to wear flip flops because they're they're on trend. You can go out at night to a club wearing flip flops. And so there's a Brazilian company. Uh that is one of the largest You know, makers of flip flops.

56:04 There's so many wees. Um To to kind of like orb change in the world. When you said you you said Amazon was your most concentrated bet in a long time. What does that mean percentage wise for you? Amazon

56:21 Right now. Is a Well Fifty percent of my portfolio. Value.

56:30 On top of that Did you say five zero or one five? Five zero. On top of that I have options in Amazon. That account.

56:43 Sure. You know. Another fifty percent. So theoretically, I mean Yeah. If you count the the

56:51 the amount that those options represent. It could be like seventy percent of my portfolio is Amazon right now. That's how confident I am in the trade. So after you make a bet like that, you know, um Well, uh Ed Thorpe has this cool book, you know, the famous uh investor, one of the early hedge fund guys, where he mm kind of like uh funny stories. He's like I make my trade and then I just go and hang out for like six months and I just see what happens. And then he there's like stories of him like playing tennis throughout the day and they're like, Shouldn't you be at work? He's like, I made the trade, let's see what's gonna happen. So are you

57:21 making that bet and then kind of stepping away for a little while, or are you gonna be are you active every single day then? I love that concept, by the way. Um I've been saying for months. This is the summer.

57:35 to deep research. Your trade. Make it. And then just walk away because Ninety nine percent of the noise hitting this market on a day to day basis, week to week basis.

57:47 doesn't matter at all. And there is not that much happening and changing Where you need to be that concerned. About the market on a day in and day a Day day out basis.

58:01 No, I'm not completely just going off and playing tennis for the rest of the summer. I I'm heaping Up with what's happening in the market. But I don't think there's going to be anything that's going to happen over the course of the next few weeks to couple months that would meaningfully change my thesis on Amazon. Something might. Uh, but my thesis on Amazon is fairly large and it's it it it's based on something that I believe is going to

58:28 Unravel over the next few years. as opposed to unravel over the next few months. So it it it's a massive concentration risk. Then I'm putting on this trade. But this this is what I do, right? Like you you can't generate outsize returns Without taking outside risk.

58:45 You just can't do it. By the way, guys, I don't think that most people should be doing this across their entire portfolio. I always tell people like I'm not a financial advisor, obviously. But you gotta bucket. Y y y your assets for different risk categories, right? So

59:01 I think everybody should have a big money account. I don't care if you start with fifty dollars in that account, but everyone should have an account. where they're willing to take Big risk for big games. And you don't have to take your kids

59:16 You know college savings to put in that account or your retirement money in that account. You could just start making trade offs in your life. Like, I don't know, mow your own lawn or Make your own coffee, but every dollar that you save Put it in this big money account.

59:32 And then use it. To actually Take a big risk every once in a while in something that you believe in. So that You have a чаance.

59:43 of becoming a top one percent investor. But do it with trade offs. Do it with other people's money, right? Like get your hair cut every five weeks instead of every four weeks. I don't know. Like delay that big purchase six months So the big screen TV is two hundred dollars less than it was six months earlier. Take the two hundred dollars you saved. Put it in your big money investment account. If that's how you fund that account, then you're not afraid to take a concentrated risk. If you're co mingling your money all together, It could be really hard to take a big risk on something because it's

1:00:16 psychologically difficult. For you to throw that much money. Into a risky investment. So you have to bucket your money. This is like one of the most important lessons for investors. I'm willing to do it, right? Like I'm if if Amazon is the stock that takes me down as an investor and ruins my reputation, then let it be. Well, it's definitely not gonna take you d it won't take you down.

1:00:39 Uh well I don't know well, I don't know how leveraged you are, but I mean it's not like it's like a it's not like it's it's not gonna it ain't going away. No it Well it you never know. It it could be But here's the thing, guys. I have been so transparent about everything I've ever done in the market. I talk about everything. I talk about the good, the bad, the risk factors.

1:00:57 Um And when I lose I talk about how much money I lost. I I I Do not advise anyone to try to mirror my trades. I just want people to see how I think. I want them to see how I think about risk, how I think about

1:01:12 Uh concentration, how I think about you know, observational investing I just share everything with the world and by the way, you guys I think know this. I'm one of the only I don't know. I'm sure there's at least a couple others. financial content creators, I've never sold anything. I don't have courses

1:01:31 I don't sell a What's is your community free? F dude. I don't even take sponsorships.

1:01:38 Do you know that I haven't taken one sponsorship my entire life? I won't take one dollar from an advertiser. I won't take one dollar from a community member. Not what the only thing that's ever been sold is we sell some T shirts and hoodies at cost. You know, I take that back. You know the value I get out of my community.

1:01:57 is collaboration. I I get so many great ideas from our community and they help vet my own ideas. That's probably made me more money than I could have ever have made from courses and selling sponsorships and all that stuff. By the way, I have a lot a lot of respect for that. I think uh

1:02:19 Yeah, A, I trust that. Uh my trust goes up. Like I said, I was very skeptical of finance and stock. Yeah, influencers and traders on on YouTube. But you know, the fact that you're not selling courses, not charging for community, not taking sponsors and all that, that that is, I think, extremely commendable and extremely rare. So I I gotta give you props for that. I mean, here's the deal. Like we always say it, like if you're so great at something Which come on, I mean been I've been great the last seventeen years. I make an insane amount of money from my portfolio. Like I don't need to do any of that. Like like I the amount of money I make is public, right? So

1:02:55 I don't I'm very fortunate to not have to do that. And I just don't need to do that, so I don't want to do that, but I do have an overriding goal here. My goal, my mission in life is to bring every human on earth into the investor class. And that's why I'm on YouTube. That's why I'm on X. That's why I talk. That's why I do shows like this. I and I truly believe that this style of investing It's something that you could do for fun. You could do it on the side. You don't have to quit your job. You just retrain your brain.

1:03:25 to start thinking about this stuff. And you might only get one great investment the next 10 years, but that one investment If you have a big money account and if and when you find it, whether it's the next Tesla or the next whatever You're willing to throw a lot of money behind it. That could be the thing that changes your entire life. Um and my next big thesis

1:03:48 Is Podcasters, which sounds insane because there's so many podcasters, right? Like you gotta be kidding, Chris. Don't we have too many podcasters? Yeah. Let me just say this. In the age of AI

1:04:02 That we're about to enter into. We are going to deeply appreciate Humans. I think that's my thesis. And while we will embrace technology and AI and efficiencies and all the wonderful things it's gonna bring to us.

1:04:17 I think We will equally appreciate the most human of human voices. And human personalities. And We are going to need that.

1:04:27 for connectivity to remind us of what's real. So what's the b uh like what would the product be? The bet is that we are just getting started with podcasting and I believe the entirety of the future of media. is new media. And podcasters

1:04:44 will continue to get bigger and bigger. I think the most Human of human voices. will become infinitely valuable. The next ten years.

1:04:56 I think within the podcasting sector. I think women are slow to become podcasters because we have so many brilliant solo creators that are women on TikTok. But women tend to be really intimidated by friction. by bridging into podcasting when you need to have camera equipment and editors and clippers. And you need to have staff, right?

1:05:20 It's and you need to invest money and capital. So I believe the most talented women voices in the world. Are not yet podcasting. So I'm opening up a podcast incub studio in Austin, Texas. Where we are going to attempt to develop A very boutique studio, but we're going to attempt to identify the most talented women voices in the world that are currently doing content.

1:05:48 As solo creators. And help them bridge into the world of durable, repeatable Podcasting. Which we believe is just getting started. I think if you move forward five to eight years. There will be hundreds of podcasts.

1:06:04 that are worth a hundred million dollars or more. I'm not doing this for the money. I'm doing this. because I I just I know that this could be really big And I have so much fun working with other creative people.

1:06:18 I love podcasters generally I it's all I do is watch podcasts, right? And and and and sit in on podcasts. But when I look at like Women's podcasting, you know, seventy percent of podcasters are men. So I think there's this huge opportunity the next few years as podcasting becomes more programmatic. Uh to help develop

1:06:38 podcast into what they will be'cause I don't think the future of podcasting is like Two people in a studio talking on mics, no offense. I mean my my my show's three guys in a studio talking to mics. I I I think it will become Uh, I think it will be that probably for financial podcasters and and and and business podcasts, but I think for Like general audience podcast.

1:07:02 Especially for women. It will become more programmatic. When you when you say programmatic, what does that mean? Okay, so Are you familiar with

1:07:12 Uh financial audit. Caleb Hammer Show. Yeah. He's he's the third biggest podcast in the world on YouTube.

1:07:21 Okay. His show Із програма і газ на акчупрограм. That expresses itself through a podcast format. Okay.

1:07:31 So he has guest on the show, but he has a very formal program of entertainment. Right. And so that Is the future of podcasting.

1:07:42 So we have to get more creative with podcasting. We have to take risk. Caleb took a big risk with what he did. Have you seen Friends Keep Secrets? No. What is that? You gotta check this. You're gonna love this. Uh so this is Lil Dickey, the rapper, Benny Blanco, the producer. Yeah, I'm sorry, I have seen it. It's been the greatest show ever. Yes. To me, that's an example of what you're talking about. When I saw that

1:08:08 I was like a little bit mind blown and uh you know I'm doing podcasting twice a week for six years and what they came in and did I I I really feel like the real creatives have arrived. Into podcasting because now you see Conan O'Brien's got a podcast and husband's got a podcast like the real comedians at podcast, the real creatives at podcast, and now what they're doing to the format because they come from a different background. Is there approaching it?

1:08:32 differently. Like they got a house and they staged the cameras and The guest shows up almost like a sitcom, you know, a at the door and then they open the door and then Yeah. And then they move from the kitchen to the living room and they have these bits that they do. And the the way they do their ad reads, you're like, Oh God, their ad read is more entertaining than my my actual content. Jesus. I need to I need to up my game. Sean, you Sean, you you got it. You just you just nailed it. Now fortunately

1:08:56 Again, like the type of podcasting that we do is kinda like You know. like education and business and finance I think we can afford to be very slow to change because it's just different for us. Like a lot of the people that watch your show.

1:09:13 that watch my sho. They primarily are looking to I think the personality entertainment piece is like ten to twenty percent of the show. If i if we tried to make it fifty percent, we might lose our audience, right? But um

1:09:32 For the future of podcasting, I think it looks very different. Broader based. I think it's gonna be exciting and like Here's the thing, guys. Like I've been talking about stocks for ten years. Like I love it, but I kinda like I'm bored by it. So like I like diving into these different areas where I get to be a bit more creative with other

1:09:52 Yeah. Uh, and not just talk about stuff. And that's why I enjoyed the Pokemon thing. Like I didn't collect Pokemon, but it was kind of fun being around other people that were passionate. about something and I like in my mind like how do I make money off this guys like how do I make money off a Pokemon? That's how I did it. I I did it from starting the convention that the Pokemon enthusiasts would come to And enjoy. Right.

1:10:17 And you got to be the uncle and not the father, right? Somebody else ran it. And you got to pitch in where it was helpful and fun, but not necessarily the day to day. Is that is that right? I didn't get I didn't have to do the full day to day. I got to kinda do the day to day when we would have shows, but behind the scenes I wasn't working full time. Yeah. For sure. Um but man, was it a lucrative journey and Damn was it fun. So fun.

1:10:41 Thanks for doing this. You're uh now I'm like I have all these notes, like all these rabbit holes I'm gonna go down. This this uh the podcast thing, the Yeah. Collecticon, that's crazy. You uh You got layers. Well, you know what guys like

1:10:54 D here's the thing. I'm really fortunate that I have this insane network of people that I'm constantly meeting with. A lot of them are hyper successful, you know, billionaires in the back half of their career or life. And I'm gonna point like, okay, if you've had success and you can kinda do anything you want Like what would it actually be? And and I feel that for so many people on my network.

1:11:16 It always comes down to having a bigger number. And I'm like, are you sure that you're making decisions driven by the right motivations? Because is that bigger number actually going to give you fulfillment in the way that you think it is? And over the last couple of years I've come to the conclusion That a bigger number for me is going to make no difference in my level of contentment or fulfillment in life. And

1:11:42 I like the concept of grinding and creating and building and taking risk. But Not if it's to like get a bigger number. So like if I'm gonna Do something the next Three to five years, wherever my next thing is. Like

1:11:56 I want the journey. To be as fun as the outcome. So okay. My outcome that I want is to land the top twenty global podcasts by developing two or three shows over the next few years with people I believe are unbelievably talented. I want to build a great team around them. I wanna like I wanna it's the game shift of like, can I do this? There's tens of millions of podcasts.

1:12:20 How can if I landed a top 20, how wild would that be? How But I want the journey. Been trying to figure out. How to win. How to get there.

1:12:30 To be fun. And I know I love working with creative people. I kinda'cause I've been stuck in podcast worlds for the last seven years, I kinda get it. Right. So like

1:12:40 I and I love it. So like Whether I end up winning or losing and by the way, if I win I'm looking at f I'm looking at adding to my charitable foundation. That's like my number is not for me, it's for it's for the foundation. But the journey and how we get there.

1:12:55 will be fun regardless. Like'cause I'm gonna be around creative people. I'm gonna be in a sector that I love. I mean when in history Could you take a few million dollars and start a media company, which is exactly what I'm doing. Right now. Like Could you imagine like

1:13:09 Twenty years ago. You couldn't do that. You just couldn't do that, right? Now You can s you can land a top five show globally if you if you execute. In three years.

1:13:20 Two years. Isn't that wild? That like you could do that out of one studio with like 10 people, 10 or 15 people. Like, how exciting is that that you could play in this game and you could have a top five global g global media show. In a couple years.

1:13:37 If you can find the right person And the right team. And the right format. To me? That

1:13:45 That journey of just attempting to accomplish that. is maybe the funnest thing I will ever do in my life. So I'm really looking forward to this next Hopefully we win, but even if we don't win, it damn guys I'm at a point I'm gonna have fun.

1:14:01 I'm gonna have fun d trying. Okay. And but and by the way, like I tell this story to a guy, I had I had I had lunch with a guy, massive exit. This I don't know how much he's worth, but it's a lot. And I and and I I talked to him about this story and he said, You know what, Chris? I'm going to buy this bonsai shop that me and my daughter go to.

1:14:23 He goes,'cause this is my favorite thing in the world. Me and her go there and we just hang out there. And I'm gonna buy it. And like This guy's gonna end up spending more time with his daughter. He's gonna have fun because he's gonna take this little bonsai shop. It's been around for thirty five years.

1:14:37 And try to grow it with her. They think which is kind of cool. He's gonna actually he he's an AI guy, right? So like he's gonna actually like apply artificial intelligence into the growth strategy for the bonsai shop. He's gonna maybe get some content creators and influencers to try to like take it global through e com. Like there's all kinds of fun stuff you can do here, starting with a little bonsai store that you and your daughter love. I'm like Now That's a great way to spend the next five years of your life.

1:15:06 There's a lot of people that have made it that have enough money that they could kinda can do what they want. Like we're so set on just like bigger number, more happy, bigger number. No, no, no, no, no. I actually believe That there is a point. When the bigger number Have the opposite effect.

1:15:23 It definitely one hundred percent. Make sure. Less fulfilled and less happy. Well y you know why? M mo most people think that's like a mo money mo problems thing, but it's it I th I think underneath

1:15:36 That is You have no excuse left. You know, for basically for f when you don't have a lot. You can always tell yourself, Well, it's on the other side of this. And then once you get to the once you get there.

1:15:48 There's nothing left to blame for any lack any h any internal holes. Any internal anxieties or um Feeling of lack. Um or just dissatisfaction. And so you can't You can't blame that anymore. You've lost the excuse. And I think that is a very like tough moment. for for people when you don't you no longer

1:16:09 Can say, Well, it's because I don't have that, that's why I feel this way. It's like no no, I feel that way because that's how I am and that I think that's a pretty brutal realization. At least that's what I've felt and what I've seen. part of it, I think a big part of it is that you become disconnected with other humans. and you can't relate anymore and people treat you differently and it gets harder to maintain And develop authentic real relationships. You can't do anything about this.

1:16:38 Excessively wealthy. to the point where nothing matters anymore. You just don't relate. T. daily things the same way as the rest of your family and friends and colleagues do, and they sense that.

1:16:54 And then also when you meet new people and like you like Listen. you start going to certain types of vacations and certain types of dinners and you hang out. Maybe you have a yacht and maybe you fly private. And then it's like, well, this is what I want to do with my time, but I just want to spend time with my friends. So maybe your friends are now on your yacht and doing five thousand dollar dinners and your friends or maybe you have to bring them on your private jet.

1:17:19 And like you're paying for them and it makes things really weird because then it's like, Wait a second. Or these people They don't even rip on me anymore. They don't even treat me the same anymore, maybe'cause they're worried that like They're not gonna be part of this lifestyle that I'm

1:17:36 paying for only because they can't be here unless I pay for it. And I don't want to I want to live the lifestyle and I want my friends to be with me. There's just so many problems that organically surface when you enter that stratosphere, which used to be like this many people, but in 2026, guys. There are a lot of people with excessive wealth. Let's be honest, like the number of people that have excessive wealth in 2026.

1:18:04 For a variety of reasons, okay. are are enormous. The number of people that fly private, the number of people that spend three thousand dollars, two thousand dollars a night on hotel rooms and resorts, The number of people that are going out to dinners at these places where they're spending

1:18:21 Just wild amount of money on a regular basis. The wealth class is huge, and I think that ultra high net worth wealth class. is probably Miserable. Because of all these factors.

1:18:35 And It's really hard to stay grounded. It it's exceptionally difficult. To like stay connected. And you guys know there's nothing more important in life than being deeply connected.

1:18:49 with other humans. Nothing. And this thing makes it very hard. To stay deeply connected. So It's almost like a hack. Not letting yourself

1:18:59 Get to that point. I know it sounds crazy. There is There is a sweet spot. I think there is a sweet spot. for wealth and it's different for every person. And you can kinda sense when you kinda get out of the range. Of that sweet spot'cause you can kind of sense these things starting to happen.

1:19:18 And there are a lot of ways to knock yourself back down. One of them is starting a foundation and just giving money into the foundation, right? Like it's not yours anymore. It's in the it's not yours. You give the foundation it belongs to the easy. the foundation. And you get to do good things with it. Also, you can take that money and like you can invest it in other things that puts it at risk, but again, it's not yours when it's invested and illiquid and put at risk. So now your access to like liquidity and your access to money that you know is bankable becomes more reasonable.

1:19:48 And like You don't push yourself. T into that stratosphere of overspending. on a regular basis. I agree with every word you just said. Every word you just said, I I totally agree with. So I but I think it's a topic that quite honestly not only people don't talk about, but I think most people don't even think about because like your brain doesn't my brain for some reason. Well, I could if you don't do it appropriately, it sounds kinda douchey if you talk about this stuff publicly.

1:20:14 I mean that's like the easy like that doesn't mean it shouldn't it's not an important I mean like it's super helpful. It's just helpful to like maybe a small group of people. Th there was a great bl blog post on this by um Julie, I think Zhao was her name. She wrote a thing uh to all the folks who were about to get rich. It was right before the SpaceX IPO and sh She was at Facebook right before Facebook had its IPO and she talked about what she observed and saw of the people who, you know, had been working really hard for a long time and suddenly the sort of shackles of liquidity were were off them and and now they had the money. And what what did you do? And she talked about how people play that game and Chris, your your point on disconnection is one that she made a I'll read you a little part of it. She's

1:20:51 She's like um Once money can buy you anything, you become a bit a bit of a character. You can eat at fancy restaurants all the time. You bring a full zoo and carnival and a chocolate train to your kids' three year old birthday party. You know, you become so cloaked by these fancy things, shiny things that you can you can buy. And that sparkling cloak can become so distracting that people can no longer see you. You become harder to connect with. And she talks about like the it's

1:21:15 the the disconnection can lead to is is a great source of unhappiness. You know, I saw this with a f I have a friend who Got very, very wealthy through real estate, bought a Mega Mansion. eighteen thousand square feet. He's literally not only did he move away from his friends and family because

1:21:32 We don't afford to live in that place. That that neighborhood. That neighborhood has acres in between houses. Um, but then even in his own house, he was disconnected from his own kids where they were, you know, on the in the West Wing and he's on the east wing, ten thousand feet apart. The money literally, I watched it make him less happy. Um, because it would create an immense amount of social disconnection on on many, many levels. And I I remember When I first moved to San Francisco I worked for this guy, he's a billionaire and We went out to lunch. Um

1:21:58 W as a group of us, five of us. And uh At the end he was like you know, he tossed his card in, but he was he basically was like, Oh, should we all just put our cards in? And I was like, man, this guy what a cheap billionaire. This guy didn't even pick up the tab. And I realized like actually it wasn't because he's cheap at all. He's not a cheap guy at all. He's very generous. But He didn't want to change the social dynamic between us, where it became this weird power dynamic or this weird like subservient

1:22:22 And he was actually doing us all a quite a big favor by not doing that. So you start to see these little moments of d possible disconnection versus connection. Facts. I I always wondered like why am I seeing this and none of the other people or very few that are in the same place? seem to see it. I think it's because I've like retrained my mind to be an observational investor. So I'm constantly observing life and culture and rel like everything I'm just being hyper observant about.

1:22:50 And it kind of translated to this, and I was hyper observant about this, the part, the birthday, like all the stuff, right? And I was like, damn, I cannot fall into that trap. I do not want to be miserable. Like a lot of the people that I see, and you know, you've seen this, right? Like it you they fall into the traps, and then it's like it never leads to a good place. But I will say this also, because a lot of people will see shows like this and like, Oh, it's so easy for you guys. to talk about, you know This when you have it, I will

1:23:21 Admittedly. The sweet spot is pretty sweet. Okay, so like so I'm just gonna say the sweet spot of wealth is pretty sweet. So d don don't mischaracterize what we're talking about. Gain financial independence is one of the most amazing things one could ever experience in life.

1:23:41 What that buys you is actually insane. B. Being in full control over your time. how you spend it, who you're with. Where you go and never having to work.

1:23:54 for someone else again. That is magical. That actually is as good as you think it is. It really is. It's actually better. It's it's better. Okay. It's I I remind myself I talk to some of my friends, I'm like Hey. Um Dude, I just don't like a reminder, dude, we hadn't worked a real job in like fifteen years. This is pretty freaking nuts. And my buddies are like, Yeah, do we forget how good we have it? I'm like

1:24:18 I'm like, do you know like how many of our friends and colleagues are still getting up every day and going to the job we had fifteen years ago? And because we became independent investors and became part of the investor class and aggressively investe money in equity markets and now we're independently financially free. We're podcasters and we're investing and we're working really hard. We're starting businesses and backing other businesses. We're probably working harder than we've ever worked in life. But it's optional.

1:24:50 It's optional and we're doing it because we enjoy it. And we're financially free. To be at every kid's soccer game. We're financially free to be with our family and our friends whenever we want, however we want. Like I used to have the cubicle job for many, many years, guys. many, many, many years I had the job in the cubicle, uh doing sales calls.

1:25:14 Right, and so I try to never forget how awesome it is. To like not be in that position. So yeah, I I don't mean to rip on getting wealthy'cause it's pretty damn awesome. It's just Keep it manageable. Because there is a point of diminishing returns, and then there's a point of deeply

1:25:33 deeply negative returns on every dollar you spend. Not every dollar you make, but every dollar you spend. After after that point. You're cool, man. Chris, this was fun. I like having uh we like having you on. We like talking to you. You got to do a part three now. Dude, you guys are the you guys are the best. I would I'm always up for it. I I love it. Well we appreciate you so much. That's it. That's the I feel like I can rule the world, I know I can be what I want to

1:25:59 I'll put my all in it like my day song. On the roadless travel, never looking back. All right, let's take a quick break to talk about a podcast. Cause if you're listening to this, you like podcasts. And what's better than one podcast? Another podcast. And let me tell you, another podcast you should check out. It's called Success Story. If you like hearing about different success stories and hearing QA sessions with successful business leaders or hearing keynote presentations or just checking out conversations about sales and business and marketing tactics, is a great podcast for you. So check it out wherever you get your podcasts.

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