The Simple Way to Create More Luck, Friends, and Opportunity

I could only lose $3 million. I could gain $300 million.

All right, Shil, what's up, dude?

Not much, man.

Doing well, dude. Always good having you on. You are, as always, I give you this title, the most interesting man in tech. You're, you're a great investor. You're a tech investor. How big is the fund or how much total have you, you invested now at this point?

About $450 million total.

Okay. $450 million. So like, you know, I've learned a lot from poker, right? And in poker that you learn all these lessons that actually like cross-apply totally outside the domain of poker. What would you say are the lessons from investing that apply to life?

I think, you know, one is just like upside can be greater than downside. Like, so if I invest in a company, let's say I put $3 million into a company there is a possibility of it being $300 million, but the downside is capped at $3 million. I could only lose $3 million. I could gain $300 million.

Yeah, because if you don't work in, uh, investing or anywhere where you have that sort of asymmetric risk versus return— let's just say you have an hourly wage job, right? Like, you're sort of— your mind gets trained into this linear: I put one in, I get one out, right? Like, I can't put one in and get 50 hours of pay out of this next hour. That doesn't really ever happen in a normal job. But if your job is investing, you're like, oh, of course that happens all the time. I lose 1x my money, but sometimes I gain 100x or 1,000x my money back. And that kind of breaks the brain and you sort of like start to see, you know, other opportunities similarly that have that, as they say, the asymmetry of risk return.

All right.

So that's one. There was something around just portfolio theory, like, you know, out of the $450 million you deploy, Right? Like, what does, what does winning look like? You probably need to return some multiple of that $450 million. So what does winning look like for you? You put in $450, what do you need to get out for this to be a success?

A couple billion dollars.

Couple billion dollars. Let's say $2 billion. Let's just use it as a rough math.

Let's say it's $500 million to make math easy. Right.

So $500 million, 4x it. That would be great over some 10-year period. Yeah. Now, of that $2 billion, how many companies would you go into? And of those, like, how many companies would be responsible for returning all of that money? It's only going to be a few, right? Give me the math there.

Yeah. So almost all of the returns are going to come from like 10 companies out of hundreds that we will have invested in. Correct.

And so there's something like that in life too, right? Whether it's like people you meet or dating or like there's some portfolio theory, some power law where the few will drive like all of the joy, the value, the relationships, the opportunities, whatever. And then you just do the rest because you need a portfolio in order to find the few that are like, yeah, the big outliers.

It's true. And it's also, it's also in a related note, there's like, if you increase the surface area of companies you meet, you have the better odds of finding that one, like what you really know it's going to work. And so in life, I think increasing surface area is good, like saying yes to stuff, right?

There's a great blog post this guy wrote called Building Your Own Yacht. Had Have you ever read this blog post? It's like very obscure. I got this from some random Twitter account, The Real Estate G6. Sorry. Like, normally I'd be like pretty low expectations, but this, this overdelivered. And so basically it argues the following. It says most people in their life, they don't do anything that compounds, right? Like most people are non-compounders in general. Okay. So we, and then we kind of know that, okay, money has this compounding thing, right? You can compound some interest or rate of return. 10% a year in the S&P 500, and over every 10 years that's going to, or every 7 years, that's going to double. Great. So you sort of see compounding financially, but everything compounds, including relationships, skills, knowledge, everything else. And he has this story about building your own yacht. So, um, let me read this out for you. Okay. So he goes, if you aren't familiar, Aristotle Onassis, by the way, this might be a totally fictitious person for all I know, but it doesn't matter. The story works either way. He was one of the wealthiest businessmen of the 20th century. He started off as a tobacco trader and he ends up, you know, being this big shipping magnate, right? So he's like, he makes his bones in the shipping industry. He's dating famous actresses. Okay, so he lives this life, but he has this one sort of hack for relationship building. He called it building your own yacht. So he basically talks about how this guy basically, one of his investments was this yacht, which seems just like a splurge purchase, like a discretionary purchase. But he argues like, think about the power of having a yacht. And he goes, the way that humans are wired is like we are very suspicious of cold introductions, strangers on the street, people emailing you that you don't know. But like a warm introduction or a warm, uh, relationship is so much— you've already bypassed like 10 hurdles that come from taking somebody from cold to warm. And so he argues, he's like, think about it this way. If you think about relationships, you would want to have, uh, if you meet somebody, you want to do business with them, or you just want to socially connect with them. You would want social proof, like, is this person cool? Are they legit? Are they friends with people that I already am friends with or respect? And basically, it's like, from the moment you step foot on a yacht, social proof is done, credibility is done. And he's like, on top of that, you enter their frame, like you are literally on their turf. And from the end, he's like, there's also the law of reciprocity, which is like, if I invite you or give you something, there's a part of you psychologically that will want to reciprocate in return in some way. And often the law of reciprocity, the way it works is like, it's not one for one. So like if I, you know, just do you a quick favor, bring you a drink, and then I ask you for a much bigger ask than the drink, you're more likely to say yes to it. And so he talks about how— and he's like, yeah, okay, that works with the yacht. But he's like, in life, there's actually all these little yachts that you can create that don't cost the same amount as a yacht. So, you know, you host a dinner, right? You create an event, you send out, you know, free materials, a newsletter, content. Those are all— these are all little yachts. You can create, create all this like inbound luck and relationships and things that can compound because you create this like asset that you get to use from there on out. So I thought that was like a very interesting point. I'm curious what that brings up for you.

Totally. And I think like for you guys, the podcast is partially that.

Yeah, exactly.

Thanks to this conversation, I think I'm going to, I'm going to start doing more dinner parties because I think it's just like, so such an easy way. You bring people together. Like, also, oftentimes I meet somebody and I'm like, I want to hang out with them again, but there's no real—

no excuse.

There's no excuse. But if you just invite them over, it's better. And I think actually, I think the best thing to do is invite them over to your house because then there's some feeling that like, it's a much stronger feeling than if you invite them to a restaurant.

Well, even as an investor, Sacca did this, right? Chris Sacca did this with his— he moved out of San Francisco where— yeah, in San Francisco you don't have a yacht. You know, you're just meeting at coffee shops and little, you know, little places like this. You have an office, but everybody has an office. There's nothing special about it. He moves to Tahoe and Truckee, actually, and he basically has like a cabin on the mountains with a hot tub and you can ski. And his dog is there and his kids are there and he's got this guest house. And then he invited, you know, Travis from Uber over and they hung out for 2 or 3 days and invites Kevin Systrom. Hey, dude, come just work out of my place in Tahoe for the week. And then when they're on his turf in his yacht, obviously, like, the connection and the depth of the relationship built way faster. And he basically attributed that move to, you know, some of the best investments of his career is like having that little yacht.

It's great. Makes, makes complete sense.

I've talked before about the way that I know how to make money, about how to build a moneymaking skill, about how to leverage your time and energy. And the team at HubSpot actually went through the video where I explained all that and turned it into a free downloadable cheat sheet on my 4 rules of how to make money. Now, this is not, you know, get-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. Yeah, there's some people who have done a— they've sort of productized this in an interesting way that I've met. They, uh, one person I know, they knew that Nick Gray is amazing at these 2-hour cocktail parties. And so they just like were like, hey Nick, like, can I commission you to do the dinner party part for me? And, uh, and he's like, great, I love doing this. And so they worked out a deal where he would do it for them. Or I know somebody else that did this with, um, if there's a conference in town, they would kind of free Airbnb. Actually, Travis from Uber used to do this in his old, uh, blog post. He talked about what he called the Jam Pad. Which was his house in San Francisco. He's like, hey, if you're in town for this, you could stay at the Jam Pad. And he's like, you know, what does it cost me to have some people on the couch? Nothing. A little inconvenience, a little— I might have to put up with some weirdness, but ultimately, like, I'm creating this magnet, this little mini yacht where I'm just going to have this flow of interesting people coming through that might— who knows? Who knows what's going to happen? But the asymmetric upside was there for him.

I've got a friend, Satya, who does this poker game every week and he'll invite anybody, all sorts of interesting people from like CEOs of like prominent companies to— I was, I just went to this deli, had a sandwich. I loved it. Was talking to the owner and he knows Satya and he was like, yeah, he came in here. He loved the sandwich. And then he invited me to play poker. And I was like, that's so interesting. And he, this, like this guy went to go play poker with these CEOs and You know, all sorts of interesting stuff has happened thanks to that. So I think that's his little—

yeah, it's interesting. You know, these are all so obvious, like, oh, host a dinner party, whatever. But if you kind of look— I know, at least for me, if I look at my life, I'm like, I'm, I'm very underweighted there. It's like, you know, I'm pretty overweighted on, I don't know, social media or, you know, other things that I spend a lot of time on. And these other things that I think if I, if I'm honest with myself, like, would clearly add value and I just don't make the time for them. Like, and then sometimes you need a reminder or in this case, like, just the word of like, oh yeah, I'm just building a yacht here. Suddenly it elevates the importance of the thing I'm doing from like, I'm just hosting some people over, we're going to have a dinner to like, no, no, this is part of my, this is part of my yacht. I'm like this Greek dude, you know, that's me right now. And so sometimes you just need to delude yourself.

Totally. Another one is, so, you know, we're both active on Twitter. There are folks that are like mutuals, folks that you like their stuff, they like your stuff. Recently, I would say like once a month, somebody, I meet somebody for the first time because there's somebody that is a mutual on Twitter. Like we like each other and they reach out to me and say, hey, like, let's grab lunch. And it's usually people in from out of town, like people who are in town, you just expect that you're going to see them. But if somebody's in from out of town, they're coming to San Francisco, they, they go on a mission to meet all their Twitter mutuals. And I think that's great. Like people, people should do that. Like when you're traveling, especially in San Francisco, if you have a lot of mutuals here, just reach out to them.

Right? Yeah, that's so true. It's like tourism, right? Like if you, like, I've never been to Alcatraz. I've lived here for 15 years, but if I came to visit, I would have seen it that weekend.

Absolutely.

You know, I was going to ask you about AI because I feel like you're pretty plugged in and you have, you're a thoughtful dude. So I think you have opinions on kind of like where the world is going. So I want you to paint the picture like Game of Thrones style. You know, the intro of Game of Thrones where they have the big map. It's like, then you have this map first. So like the high-level map for AI is like, what— here's what it appears to me. I'm curious your point of view, that there's this, um, race. And I don't fully understand the idea of a race because it seems like whatever one company does, the other companies have 6 months later. So I'm not sure, like, if you got to the finish line, then what? What is the finish line and how do you win this supposed race? I'm not sure about that. But obviously so much money is being invested that somebody believes that there's like a victory condition of this race. So I'm curious about that part of it first, like the the concept of an AI race. What do people actually mean and how is that going to play out?

So many things in life have been winner-take-all, in tech especially. Yeah. So like there's one major search engine and there's one, you know, Facebook on social media. Of course there are others, there's Twitter out there, but a lot of these businesses have scaling returns or network effects and The same is true in AI, probably. Like, one company is gonna have all of the context they need to be your best assistant. And so I, I feel weird saying this because I use, I right now use Claude, Gemini, and ChatGPT every day. And some queries I'm doing the same query on each. But in the long run, that's not really sustainable. And also not everybody's like me. Most people are probably just gonna have one. Yeah. And the context embedded into it, which is like all of your past conversations, or if it's Gemini, they have all your email, or you know, if it's, if it ends up being Meta somehow, they have all that context. That's gonna be really valuable.

So the first idea is that everybody in the world is gonna want, is gonna have some ultra smart helpful assistant, which is some blend of like Google that just answers your questions for you. But then also like can make things for you, write things for you, create a plan for you, research a thing for you, like do the job for you. And like today, that's— today the leader is ChatGPT. I think they're like close to like a billion MAUs. And, you know, Google's going to quickly try to like, you know, Google's trying their best to do that. It seems like nobody else is close in that race specific, that specific part of the race that every human has an assistant.

OpenAI kind of launched ChatGPT and it was unexpectedly a hit for them. It's, it's crazy to think now, but they didn't think it was going to work that well.

Right.

And OpenAI was an enterprise company. And then through the success of ChatGPT became a consumer company. But Google already has all of this context on you. And they actually started this whole LLM thing. They screwed up along the way with Bard and all sorts of funny stuff that they did. But now Gemini is really, really good. And so in that consumer race, they've done a very good job. Gemini has, and I think has the momentum on consumer right now. Then there's the enterprise piece, which is like a lot of enterprise folks use Claude, and I personally use Claude more than I use ChatGPT, and it just allows me to do more things like for, for the kind of research I do on companies. Claude is just my partner. It's my sparring partner. Like, I'll— it's like having— like, we actually didn't hire somebody this year because we're using Claude more than ever.

Well, you essentially did. You hired a person named Claude, essentially.

Exactly.

Okay, so there's the race to have— everybody gets the sort of all-intelligent, super helpful, always next to you chief of staff. That's, that's the ChatGPT analogy. Then you have, um, you know, like in Game of Thrones, you'd have like the whoever like is like really good at the sea battles, right?

The ocean.

Yeah, that's, let's say, enterprise. And Anthropic's doing pretty well there right now. And then, and they're all going to compete for everything, but like, they're doing pretty well right now. And then you have the king of the north. So you have Elon up there, and he's marching, and he's like, I'm gonna put data centers in space, and I'm gonna catch up with Groq, and we're gonna win. And so what do you, what's your take on how that, where does he go? How does that work?

I would never, ever, ever bet against Elon, but As of right now, I find Groq to not be as useful, but I think, I think like it's possible that everyone has their favorite and, you know, over time people sort of slot into their favorites. Right.

It's like Coke, Pepsi.

If you're, yeah, like Coke, Pepsi. Right now, if you are a co— working in code, you're probably using Anthropic.

Right. Okay, so now, okay, let's keep going through the battle. Then you have all these SaaS companies. You've got, you know, today's sponsor HubSpot. You've got Salesforce. You've got like all Adobe, Figma, all these companies that are like cranking on revenue and growth and earnings. And then their stock is just plummeting because the market believes that like they're going to, they're going to get somehow eaten away by— I believe it must be that that's why the stock is going down. The business fundamentals are strong. But there's this question of 20 years in the future, is this company stronger or has it just been eaten away by AI that can do all these things? What do you think happens there? Is that overblown? Is that a, is it a buying opportunity or are you equally suspicious of the future of these companies?

I'm suspicious of the future of a lot of these companies. And I just think about myself like right now I already am doing a lot of image creation in Gemini. Nanabanana. Um, I, I'm a paid user of Canva, uh, a bunch of Adobe products. Uh, and yet now most of my image generation is already on Nanabanana. It's just so much easier.

Right.

So then like, can those guys build it? Probably yes. Like some of them already have pretty good stuff. Like Adobe's AI stuff is very good. Figma's good, but Will I just, will there just be one model to rule them all? And I'll just do everything in there. It's my assistant. My assistant's doing it for me. So what do you need to be successful as an independent company is a good question. Because if you look at all these like early AI companies, so there was like, there were the ones that just helped you write. Jasper was one. There, there's some others. And like those guys, I don't know how they're doing now, but I imagine not well because I don't need another tool to tell me how to write. Like, ChatGPT can do that for me. And then I think the same is probably going to be true in image generation. And then all these other products too, like even, even law, there are these companies, Harvey and Legora, which are both doing phenomenally well. Um, but Anthropic launched their own legal thing. So like, What are the businesses in which you're, you have less to worry about being cannibalized from an existing AI?

Right. There, there was like a quote from Sam Altman maybe 2 years ago or a year ago where he said, uh, they were kind of asking him this question, hey, developers are trying to build, but we're all worried we're gonna get steamrolled. And he, he was like, yeah, you should think about what we are not gonna build. He goes, here's a simple test. Like, um, there's some companies that when we say there's a new model update, they get really excited 'cause it made their existing things so much more valuable. And then there's other companies that are terrified when we say there's a new model update because we might have just swallowed what they did and you should think really carefully. And their response was sort of like, okay, so, so wait, what are— so what are those things that you're not going to do? Right? That's like, it's like a meme where it's like, wait, so are you going to say what they are or we just need to guess? Right? Because it seems like an ever-expanding scope. That's pretty tough. Seems like the lawyer one would probably be easier because A, lawyers, uh, you know, it's a workflow-specific thing. There's like security compliance. There's like, it's like really like a lot of nuance that you would have to build on top of that. Even if ChatGPT can quickly generate a document and write it or read it, still probably there's enough like domain-specific workflow and risk where somebody specializing in it will solve the 100 small problems that the lawyers care about, uh, that ChatGPT's product managers aren't going to care to do. Totally.

I think that's true. And I, I think in your, in your, the case of HubSpot or Salesforce, like, I don't think those things are gonna change overnight. I think it's gonna be, there's a, people are gonna keep using those like systems of record for a long time. As a fund, we think about this a lot. And my partner Nihar wrote, wrote a piece last week called The Last Mile Problem. And basically we talk about what matters and it's what you just said, domain context. And workflows. So like if you've got the specific terms and norms of a given field, if it's healthcare, legal, accounting, you can produce more trusted outcomes. Um, and integrations. So like integrations into your Salesforce instance are valuable, um, or in health EHRs or whatever the case may be. And then there's also some like compliance and human-in-the-loop element that I think really matters. So I, it's hard to know though. It really does feel like a lot of these businesses could at least be very challenged by the general models.

What are some, like if I just gave you $1 million and I'm like, you got to invest this into any AI companies, public, private, anywhere. What, where do you have like a lot of conviction? What would that, what would that portfolio look like? Where would you put the bets? Let's take, take $1 million. Where are you putting the bets?

Yeah. So I would say like right now with, you know, Anthropic being valued at nearly $400 billion and OpenAI at like $800 billion, I don't— I'm not going to put it there. Like, how, how big could those companies get and what's the risk reward? I think, you know, could they be trillion-dollar companies? Yeah, but they better be trillion-dollar companies, right? Like, if they're not, that's a failure, right? So I'm not putting it there. Um, it's wild to think that like we only had the first trillion-dollar company like not that long ago.

Yeah. Now those are what, 6, 7 years ago?

I feel like it was a really big deal. And now we have basically almost trillion-dollar private companies that didn't even exist 10 years ago.

It's crazy.

Okay. So where would I put that money? So I think it'd go back to this, like where are, where are the vertical opportunities that are very interesting? And I think on the general consumer side, I think it's tough for me to find one because on the consumer side, it feels like I probably am going to be using Gemini or ChatGPT or one of those generalized models. They're gonna end up getting my context for, for the stuff I need. You know, there might be other interesting ones that do stuff like, Suno for music is interesting. They've actually, they've grown like crazy to, to an amount that I would not have predicted. Um, they're like hundreds of millions of revenue, I believe.

Yeah. I'm a power user of Suno.

Yeah. Amazing. It would be a fun project. I mean, a lot of people are obviously doing this, but a fun, a fun project for somebody would be to like build a brand around a musician that you've created on AI and like market it through Spotify and all that stuff. There are obviously a lot of them out there, but if I had more free time, I would probably do that.

That'd be a fun one to do.

Yeah.

Yeah, exactly. Uh, yeah, I've played around with that idea as well. Like, what would it take to get on the charts, right? Can I take this song? Could I create an artist with an avatar? Can I build them up on Instagram? How would I do this? And just see, like, totally just get to play, you know, have, have this sort of like fantasy musician arc, you know, take, take 6 months and just see what you could do. Um, like, I'm pretty sure I could do it if I just dedicated 6 months to, to doing it. Now again, it's like, maybe it's not worth the time, but it's fun. It's on my list. It's on my, my itch list here of like possible projects.

Yeah. On a related note, I just saw this on Twitter, so I don't know if it's fully accurate, but, um, there's an Epstein Files podcast that's entirely AI generated and apparently is now a top 50 podcast on the charts.

I saw when he launched it and he was like, it's getting downloaded like 1,000 times an hour right now. And then it was like, Update 3,000 times an hour, right? It was like, uh, but what is the actual podcast? What is it? It's just reading the emails out loud? Like, what is it trying to do?

I— so after I saw the tweet, I went and I listened to the intro, and it's kind of like NotebookLM. So it's like, it's like there are two hosts talking back and forth about it, and they talk, they talk about a different thing each, each episode.

I wonder how many more things are going to be like this, right? So like, I'm not safe as a podcaster, right? Because you can, um, You can create podcasts about, you know, about anything. And now if you can auto-create it. And so what they did was they basically were like, here's the source material that's very juicy, very dense, and maybe is going to be keep growing, right? So there's some runway here. And then you feed it into NotebookLM and then you create a podcast out of it, like automatically. You could do that, like, you know, about everything. I could do that about sports. I could do that about anything that has like this, this big feed of like your feedstock to put into the, into the model, right? That's, it's pretty wild. I thought about creating a podcast that was interviews with the great dead. So it's basically like, could I do a podcast with Steve Jobs now with AI?

Oh yeah.

Like maybe I could, maybe the tools are now good enough where you could actually figure out like, what would he say? And it actually has enough, it would give like sensible answers. You could copy his voice using ElevenLabs. You could create a digital avatar using one of the video models.

Yeah.

And you could do the whole thing. And so like, that's kind of interesting. Like, what, what if I did that? That'd be cool. Like, you know, just me and Genghis Khan for today's episode.

Totally. Have you seen, um, Delphi?

Uh, the, like, they're making like a clone, right?

Delphi.

What is it?

Delphi Digital? Yes. You can make, it's delphi.ai. Um, you can basically make a digital clone of yourself. And they have them with like Arnold Schwarzenegger and other folks like that. Like you can, you can talk to them, basically do what kind of what you just said.

Are they pretty good? Is it a—

they're pretty good. I haven't, I haven't played around with it that much, but from what I saw, it was pretty good. And apparently the company's doing very well. They raised from Sequoia, other, like off to the races.

Wow. So people are like, I just want to chat with Michael, like Michael Ovitz on here. I want to chat with Michael Ovitz.

Yeah. I think like. I saw Lenny, uh, Lenny has one, Lenny Raditzky. Your guy, Brian Halligan, has one and he does like founder coaching via Delphi.

So I just asked Michael Ovitz, the creator of CAA, the talent agency. I said, hey, after this, I was like, I'm having a meeting about our podcast deal to renegotiate. What should I do? And here we go. I got Michael Ovitz representing me now. This is fantastic.

That's incredible.

He's like, you're negotiating leverage, not just rates. And then he goes into this long strategy.

Okay.

This might be awesome actually. I don't have to give this guy 10% either. This is fantastic.

Exactly. Exactly.

All right. So that's, that's AI. Are you personally using AI in any interesting ways?

I think there's some like simple stuff that's just too annoying for me to do. Like I, my, my wife and I, my wife works at Meta. She has, after, after 5 years there, you get a a 5-week break called Recharge, and we're like figuring out what to do. And there's like a ton of research I'm trying to do. And, and one of the ideas is doing a road trip on a camper, in a camper van in Europe. And, um, there are these things called relocation specials that I've done a bunch of times where like they need to move a camper van from one place to another and they basically give you the camper van for free and you can like move it over a couple of weeks. I've done it multiple times and it's, it's fun because you take the camper van one way. Normally you have to take it and bring it back to the same place, right? This is both cheap and you don't have to bring it back to the same place. And it'll usually be like a new van they have to move from the factory somewhere else.

So it's like, what is it, private jets, empty legs or whatever?

Empty legs. Yeah, kind of like empty legs. But for, for the normal people like us. So I've had AI do a bunch of research and find it for me. Message, message the camper van places and ask and ask them. That's been kind of fun and useful. I, for this event I had, I wanted to save some money and had, had AI do an exam for me to become like a licensed travel person. I saved 16% on this big, big event.

So you needed to become a licensed, what, travel agent or what did you have to become?

Yeah, it was sort of a hack because one of my portfolio companies helped me that is in the travel space. But I had to do, I had to do these exams. It was like, I don't remember how many hours, it was like 10 hours of training and then some exam. And I just, I had AI do it for me.

And so it goes through all the training material. It took the exam as well, or it took the exam. Great. Yeah, that's amazing. All right. You had this tweet a little while back. I want to— I've been wanting to ask you about. So you were— somebody tweeted out, they said the worst mistakes are decisions in human history. And they were, you know, Adam and Eve eating from the forbidden tree, the Mavs trading Luka Dončić. Right. So they were just going through random examples. And then you had a bunch from the business world. I wanted to go through this. I was curious if you have any, you know, tell some of these stories. I think— I don't think all these stories are super well known.

Totally. A lot of them are this like innovator's dilemma. That's kind of a broad theme, which is so Kodak, they invented the digital camera and then they didn't sell it because they were worried it would suppress their film sales. And then all these other companies started selling digital cameras and then Kodak basically went out of business.

It's like kind of the worst way to lose, right? Like, that's my nightmare as a business person. Exactly.

And then the same thing happened with Excite. So Excite, Had an, like, Google wanted to sell to Excite for $750,000 very early on. It was just Larry and Sergey wanted to sell this idea to them. And Excite said, um, we don't want them to get answers. We want them to stay on the page so we can serve up ads. And then so obviously the rest is history there. So those are kind of like a theme is you would cannibalize our business, so we're not going to do it. And that actually, like, back to our early discussion about AI, that's one that I, I was worried that Google would get into. I think a lot of people were worried Google would have that problem. And Google stock was really in the shitter, like, a year and a half ago. And then, as Google, like, Gemini became great, and people realized, okay, like, Sundar's not just sitting back saying, I'm not gonna, I'm not gonna do this, like, he's doing it too. And, and then Google stock has done really well. But I think that, that was a big worry people had because how Google makes money is on ads when you're searching for stuff. And if you're not searching for stuff, like their entire revenue model goes away, right?

Yeah, that's, that's a good one. What about this story of, it seems like another one is like selling early. That's the Ron Wayne story. So what's the, what's the Ron Wayne story?

Yeah, Ron Wayne was a co-founder of Apple with Jobs and Wozniak. And very early on he, uh, he had a 10% stake in the company and he thought it wasn't gonna be worth anything and wanted to focus on other stuff. So he sold his stake back to them for $800, which, oh my God, $800, not even like $800 grand.

Uh, so he owned 10% of Apple. He's like kind of written out of history. If he was, I, I didn't know he was actually like a co-founder. What, what did he do? What was this guy's, uh, role? Wozniak's making the computer, Jobs is Jobs.

He worked at Atari with, um, with Jobs and Wozniak. He was actually one of the early people that brought them together, and he was like, let's figure out a new business opportunity. And I think it was actually like in his home that they created the idea for Apple. And, um, and it was like, it was split between, uh, Wozniak and Jobs like I think they each owned 45%, but Wayne, for like bringing them together, he was like, he was like the adult, the original adult in the room.

Right.

And then I think there was something where like Steve Jobs got a line of credit that they would be personally liable for to start like to purchase materials to, to fulfill an order. And so Ron Wayne was like, listen, I can't be personally liable for this. I'm out. And he sold his shares back for $800.

What happened to this guy? Is he— has he talked about this? Did he end up doing okay? Like, there was the guy who was a partner with Buffett and Munger. I forgot what his name is. Rick something. And he, he got overleveraged. He had to sell his stake back to Buffett and Munger and basically missed out on Berkshire. And, you know, he ended up doing well outside of it. But like, you know, a cautionary tale for like kind of Buffett, I think said it best. He goes, You know, Rick was in a hurry and he's like, me and Charlie, we were not. And that was the difference.

Yeah. I looked it up afterwards. Wayne ran a stamp shop in Milpitas, California.

Yeah, this is going to be like a Netflix original someday. Tell me about this one. So you said SoftBank, they own 5% of NVIDIA.

Yeah.

And they sold it to plow all the money into WeWork. And I'm, I'm, what I'm interested to hear is actually your opinion on, um, Masa. So I don't, I mean, I don't know a lot about the guy. but, um, I can't tell, is this guy a genius or an idiot? Um, like, you know, when they, um, when he released like his, like, I believe in AI, raised the Vision Fund and he releases the deck and it's like a picture of like a unicorn flying and it's like, there's not a two-syllable word in this deck. You know what I mean? Like, it's like, this is made by children, but this is actually the deck and the vision of this, like the biggest venture fund in the world. Did he just get lucky? Is this just a guy who got lucky? And it's kind of like, uh, you know, I've been to casinos where I play against, you know, some random, you know, guy who's some Asian guy who's got a huge chip stack. And then you, you're like, wow, you assume he must be great. Then you realize like, oh no, this guy is like superstitious. And if this is happening, he goes all in and he just happened to win, right? Like, what's the story of Masa? Is he a genius or an idiot?

Yeah, listen, I know people who have pitched him and people who've worked with him who are still wondering the answer to that question. I don't know. I mean, so like the backstory for people who don't know is he had this legendary bet, which was on Alibaba. He invested in them very early on after he met Jack Ma. He put in $20 million and it turned into $100 billion. So like, just like this massive—

and he had the $20 million from what? He created like CES, right?

Is it—

was that the first thing he created? Like these tech conferences or magazines or something?

SoftBank was like a software distributor and publisher, and it was like really big in, in Japan. And he partnered, they partnered with Yahoo to create Yahoo Japan, which Yahoo Japan ended up being way more successful than Yahoo in the US. And so they, because it was a JV, they like, Yahoo only owned a small part of it. I think SoftBank owned more, and they had a bunch of money from Yahoo Japan. And I think that's what he plowed into Alibaba.

Okay. So he was a good entrepreneur, at least, right? A great entrepreneur.

I think he's like— and he's very risky. Like, he's fully risk-on. Like, he lost all of his money, then gained it back, and then, you know, does it again. And he's like, he'll, he'll like go full leverage, like all-out debt. And look, with the Vision Fund, $100 billion fund, what's crazy is $100 billion fund seemed so crazy that it was like, is it even real? Is this April Fool's Day? Like when it launched, whatever, 6, 7 years or no, I guess now 8, 8, 8 or 9 years ago. And they wrote massive checks into a bunch of companies, sometimes competing companies. And I never thought it would work. And my main reasoning for at the time thinking it wouldn't work was the companies that need a lot of money are not necessarily the companies that you want to plow money into. Like it ended up being a lot of like money-losing companies, um, that now eventually like many of them ended up being successful, like Uber and DoorDash. But you know, then there was WeWork, which I think they put the most money into.

Yeah. So what's the verdict on the Vision Fund? It did well? Or we just too early to say?

Or we're just not— I think it ended up being okay. It's an okay fund. It's not great. But like, if you're looking to deploy $1 million, like there are ways you can get 5, $10 million. Like if you invest in a good fund, $100 billion, if you're deploying $100 billion, like you're not expecting to 5x it. If you 1.5, 2x it, maybe that's okay depending on timeline.

Gotcha. What do you think people should be paying attention to? And maybe the better way of asking that is what are things you're paying attention to right now that you don't think a lot of other people are? Or, you know, the masses maybe, or even like general population of smart individuals, right? Right? So not, not like literally the average American, but also not the guys at your VC dinner. So somebody, somebody in between, right? The general smart person. What are they not, what are they underweighting, paying less attention to, um, thinking about the wrong way that you, you, you were paying attention to differently?

I think everyone, and I'm encouraging my parents to do it too, should just be, and this is like an easy answer, should be just using AI more. Um, I think when my parents give me an assignment, like my parents often are like, hey, Shil, can you book this for me? I'm their personal assistant and now I'm trying to teach them to use AI and actually they're doing it and it, it actually kind of surprised me, but they're, but they're, they're able to look stuff up on AI that they, you know, they weren't doing a month ago and they're getting answers. And I'm also encouraging them not to send me like stupid fake forwards and to look everything up and make sure it's, it's legit.

I'm curious if you have any non-consensus or contrarian opinions about something. So for example, you know, most people think that XYZ is, you know, kind of useless, but actually I think that's wrong. I think this is amazing. I'll give you, I'll give you a simple example. So Bryan Johnson was initially, I would say, completely overlooked. The first time we had him on the podcast, he really wasn't like Bryan Johnson, the kind of media personality at the time. He didn't have a big social media. He just had his website, his blog, where he's uploading like his own, like, blood markers too. And we were like, oh, this is cool. This guy's like really tracking everything and he's publishing it on a blog. And then Bryan Johnson became this like kind of like beacon of longevity. And then people were like, wait, is he a vampire? What's going on over here? Like, is this too much? And so he became this like polarized figure and now he's like full-on like YouTuber content creator. And so one of my like opinions that I don't think a lot of people share or even have thought much about is I think Bryan Johnson might be the best content creator on earth right now. You know, like, I just think he's like running circles around everybody in the same way that when people saw what the Kardashians were doing early on or the Paul brothers, it was really easy to dismiss as, you know, sort of silly, stupid, useless, whatever. And then like, you know, fast forward a decade and they've built these really big empires off of that. I think what Bryan Johnson is doing on social media is incredible. And it just literally is just a content creator. Like, I just think what he's done is genius.

I think a lot of folks, especially going into a new area they weren't before, they started on content and became successful that way. And kind of like in our, in my world of venture capital, Andreessen Horowitz, like they are basically all of the storied venture firms are pretty old. They were around in the dot-com bubble. The only new one is Andreessen Horowitz. And the way they did it was by like owning and controlling the media. And they've done a really good job at it. They have a lot of people, they put out a lot of content and it's worked for them.

And that was pretty strategic of them, right? So like they, they enter the VC world, they want to do well. You, to do well in the VC world, you need to have brand that will either bring deals to you or get you access into a deal when you want it to, to be able to go lead that round, right?

Yeah.

And so I guess like, give me the inside baseball there. What did they, how did they approach that problem? How did they, how did they solve that problem?

Yeah. So you need a brand, you want to be recognized. And the way they did it, like, so first of all, it's only like 15 years old, Andreessen Horowitz. And if you, if you look at the other storied firms, Benchmark, Sequoia, et cetera, they're a lot older and they, they really earned their reputation. Sequoia even earlier, but Benchmark in the dot-com era. So these guys basically said like, we, we're going to do it differently and we're going to provide instead of just having one partner to work with. You're gonna work with a whole team of people and we're gonna support it with content. So, um, we're gonna promote our portfolio with content, but also people are gonna listen to that content. They're gonna think about Andreessen Horowitz and think like, those are smart people I wanna raise from. Yeah. And it really, like, before Andreessen Horowitz, there was not a lot of content on venture. Like a couple guys had blogs and Andreessen totally changed the game. And they actually, they learned from Michael Ovitz. I think Ovitz did a lot in building this CAA into this, like you have this whole team of support around you and that's what Andreessen modeled it off of.

Right, right. Yeah. It seems like, you know, you had Fred Wilson have a blog or whatever. Yeah. And I've seen this now in a couple spaces where we all think we're doing the thing. Like I would say at the time there were some VCs who thought we were doing content. What do you mean? Oh yeah, I have my blog. And then they're like, somebody brings the gun to a knife fight where they're like, oh, here's what we're going to do. We're going to invest essentially, you know, like, I would, how much do you think they spend every year on just the media and content side? Uh, like, what do you, what do you think is the expense part of the P&L for them?

It's gotta be easily tens of millions.

Easily tens of millions. Exactly. Tens of millions of dollars on content. And so you're like, we're doing content. And then they were like, well, here's what we're going to do. We're going to build this like a company. and we're going to like— they made acquisitions in that space. They bought Eric's company. They, you know, have huge teams of people. They create multiple shows. They like have studio sets. They go on tour. They're spending a huge portion of their time just going on other shows. And so they go in with just a level of seriousness and scale that just blows other people out of the water. And I've seen this over and over again. The Charlie Munger quote, take a simple idea, but take it seriously, where it's like, we're doing this right. And the MrBeast, like we got to know Jimmy recently.

Yeah.

Like the last few years. And like he did the same thing. Like YouTubers were a thing and YouTubers would do these stunts. Or challenges. And he just took that simple idea way more seriously than everybody else. He's like, well, I'm going to put all the money into it. I'm going to build my own sets. I'm going to be— if you've ever been to his place, like, I mean, it's like giant. Like, he's got the biggest soundstage in North America. Like, you know, he's, he's building the biggest sets. It's like a construction company when you walk through his area. You know, he's got teams of people. Every dollar they make, they invest and more. They lose money on every video.

Right?

Like YouTubers were like, hey, we're doing, we're doing this, right? And then he did it at a different level of scale and seriousness. And so I always find that interesting because whenever you go into a new space, sometimes the right idea is actually there. It just hasn't been like taken to the limit. And if you took it to the limit, which is also what Bryan Johnson did, by the way, like totally biohacking, quantified self, that was an existing community and he just took it to the limit. And when you take it to the limit, like you get a whole new thing, a whole new level of success can emerge.

I think a lot of these folks, like, if you're, if you're starting something new, you have to take it to the limit.

Yeah. Uh, you just, uh, sent me this thing. I've, I've seen this before. So this is, uh, explain what this is. Uh, explain this.

Uh, this week I thought this might be fun. Basically, 2 weeks ago I saw that the Breaking Bad house, you know, the house that, that, uh, Bryan Cranston throws the pizza on top of, was for sale in Albuquerque. Iconic, iconic house. For any of you, anybody who's seen Breaking Bad. And so a friend of mine, a friend of mine told me it was for sale and I was like, we need to buy this.

For a bit, though, was this like very publicized or like kind of a friend just noticed, hey, that's the house? Like, how popular was it?

Like, it got out there and it was listed at $400,000 because that's kind of— it's kind of like a small— it's like a 1,900-square-foot house in the suburbs of Albuquerque, like 25 minutes from downtown. And I immediately was like, we need to buy this house. It was listed for $400,000. And so we like booked a flight to Albuquerque like an hour later and we like built this model around what are we going to do with this house? How much can we spend on it?

So you go to the house. Does it look like the show inside still or it looks totally different?

It looks totally different on the inside.

Okay, so they changed the inside.

Yeah.

Huge mistake. When they did the show, that was just someone's home. Basically, they rented this.

And it's this family that's lived in the house since the '70s. They bought it for almost nothing in the '70s. And then they, they like got a call from the show saying like, hey, your house looks like a normal house in Albuquerque that we might want to use. Wow. They only use the exterior of the house. They didn't use the interior of the house for filming.

Oh, okay. Gotcha. And are they— were they just annoyed people kept taking pictures of the house? Because in San Francisco, there's like the Full House house that was like a couple blocks from me and just people were constantly stopping and taking photos of it.

Yeah, yeah. It's extremely annoying for them. So, so much so that they built a fence around the house so you couldn't actually like throw pizza over. And then the neighbors are pissed. It's not a good situation. So they were like, let's sell this house. And they listed it for like fair market value might be $350,000, like looking at comps. And they listed it at $400,000. And they had tried to do like a museum or something, but they got, they got shut down by the city. And so it's been, you know, the show's been off for what, like 12 years? They could have, they could have turned it into something amazing in the meantime, but they didn't. They just continued to live there. And so they sell for $400,000. They listed for $400,000. We say, okay, like, how much can we make off this thing if we turn it into an Airbnb? And I love experiences that are also the house. Like, I stayed in Brian Chesky's house. I've stayed in this, like, I've stayed in a bunch of architects' homes around the world. Like I love unique architecture. So I thought like, I could turn this into an Airbnb. What do we do? So we like built this model around it. Like assuming— we assumed we could charge $800 a night versus like it's a 4-bedroom place in the area. You might be able to charge $250 a night. But given, given that it's an iconic place, like if I went to Albuquerque with some friends, I would definitely want to stay in the house. It would be worth it for the story. We assumed like 60% occupancy. We made a bunch of assumptions based on information we learned. Like we looked up what the Stranger Things house is going for, all sorts of stuff like that. And then, and then also like what the rules around short-term listings are. We actually spent time with an Airbnb consultant. Like I called up an Airbnb consultant, spoke to her for an hour and got some ideas there. And like I had this other idea of like, I'll build an RV like his RV and just park it out front. That'll be another bedroom because there's not enough space in the house.

Smart.

And so we basically, basically got comfortable that we could spend $900,000 for this thing and it'd be worth it.

Like, I'm sorry. So the math was you thought base, you know, worst case scenario, worst case scenario, ridiculously low. So you didn't even need to worry about that one too much. But you were basically— the expected case was that it would make like $175 grand a year of rental income off the Airbnb and that it would cost $120K to run.

Yeah.

And you'd net something like $55,000, $60,000 a year off this rental property that you own in Albuquerque. And more importantly, an epic story.

An epic story. Absolutely epic story. And it was just like, it was honestly so fun. Like, actually, part of the thing, part of what I love about my job is I get to do this. Like, I get to do due diligence on a space I don't know much about. And over the course of the next day, like, I learned a lot about Airbnbs. I learned about a lot about Breaking Bad, a lot about this house.

Right. And to be clear, does this have anything to do with your job? This is not due diligence.

My job is like doing diligence.

Use the same skills. Gotcha.

Same skills. So we decided we could spend around $900,000 and it would be worthwhile. It would make us a decent return. And then also, to your point, be just an epic story. Be so fun to own it.

Right.

But then the major risk was Albuquerque has these short-term rental laws where neighbors can call, call this hotline and basically shut you down if they're unhappy. And so there was some concern that that happens. And if, if the short-term rental ability goes away, this house becomes worth $350,000, like exactly, you know, what every other house around it is. And so there was some risk there that it's hard to price in. But basically we decided we could spend up to $900,000. And ultimately the house went for over a million. We don't know exactly how much, but it was sold to Adin Ross, who, uh, for those of you who don't know, who's, who's a popular streamer. And you know, for him, he's got a totally different revenue stream, which is like he can make a ton of money streaming to this audience. He can market to this audience. So he came at it with something that we just don't have and can't compete with. But it was really fun doing this.

So, um, so somebody who owns the Stranger Things house, what are they making?

It's like $2,000 a night and it's fully booked, 100% occupancy.

Did they make the inside match the show?

Yeah, they made the inside match the show and put a bunch of other memorabilia in. That was our plan too, was like reconfigure it to make it look more like the original. Like some of the rooms will look like the original parts of the show. And then the other rooms will just have like Breaking Bad memorabilia.

We had talked a long time ago about buying Michael Jordan's house, which was on sale for like a very long time in Chicago. It had like started at like $20-something million and then had dropped all the way down to like $13, $12. And on the— one of the early episodes of this podcast, we're like, should we buy Michael Jordan's house? Um, and like, can we turn it into— whether it's an Airbnb, it's like a, um, and we were like, you know, you could fractionally, like, uh, you could use an NFT basically to fractionally own it.

Yeah.

And so it's not an Airbnb actually. It's a bunch of people who co-own this thing. And ultimately we, we kind of let, took our eye off it. It ended up selling for like, I think like $7 or $8 million. Like it ended up going for like kind of a steal to this guy who was just like a business guy in the area. Um, who was like, dude, I can buy Michael Jordan's house. This is amazing. And he's turned it into like, you know, a short-term rental sort of deal as well.

I have one more thing, which is I had another business idea for people.

Okay.

So, you know, we've, we've talked about parents before. I think my dad is kind of a funny guy and I'm always trying to get him to work out to like, you know, live longer. And, you know, people like us do stuff like Barry's Bootcamp, SoulCycle, like these classes. And the idea is just a Barry's Bootcamp style class for old people. And you could franchise it.

Isn't it Zumba? Is that not what Zumba is?

It's not exactly geared towards old people. I think, I think you can easier make it easier, like sort of lighter contact and emphasize stuff like balance, joint work. And even like maybe even cognitive exercises. And you basically have this like welcoming place for people 55+ who have a lot of free time and want to stay active and healthy. And maybe you, you build like a club around it is the idea.

So that's— I think it's a great idea. I'll tell you why. So I have a trainer who basically was like, you know, kind of like had a bodybuilding era trained a bunch of brides trying to get in shape for, for weddings. All the classic models, right? Then like, you know, me, like tech guy trying to, you know, work out. So he comes to my house. I've been working with him for, I don't know, 5, 6 years now. He— so I was like, I really want my mom to, to work out. Like, I think it'd be great for her. And she's too cheap to like, you know, be like, oh, a personal trainer, like $100 for a session. That's like, you know, 3 months at the gym over here, like at the YMCA. Like, I'm not doing that. And so for Christmas, I got her like, I was like, I paid for it. My trainer will train you for a little bit. She got hooked. So then she started like, I'm definitely going to make this investment. And she loves it. She's been doing it for years now and she's been in great shape. So my trainer basically like suddenly his, his clientele over the last couple of years has totally pivoted where his entire network is basically like aunties and uncles of like the Indian community. And so like my mom was doing it and then my father-in-law started doing it. I posted this video of him running. And my father-in-law, I think he's like 79 years old. And he, I see this video on Instagram of him running and I'm like, what? Like, what is going on here? And he's like, he feels so good. He's moving again. He was having like blood pressure and headaches and things like that. This has really been helping him. He fell at our house. We had this stool that's like kind of like we shouldn't have this stool. Like a little risky. Like, I don't even know why we have it, but he was sitting on it, fell. And literally the first thing he says when he falls is like, good thing I've been training because he like bounced back right away. He didn't like break a hip. So we were like, this is amazing. So then his brother, his— and so like my trainer basically goes from my house to like people who are literally like learning to walk again, stand straight again, like just be able to move, rotate. Because one thing that you lose a lot as you grow old is you're, you're stiffen up. So you lose rotational ability, which if you go to the gym and you sit on one of the machines or elliptical, like the things that people, older people do at the gym, it's all rigid, no rotation type of exercise. And if you do rotation unsupervised, like, you can also really get hurt. So anyways, he's been doing this, and I've been telling him the same idea. I'm like, bro, you should— like, this is a real act of service that you're doing for the world. And there's not other great options for, you know, people who are 50 to 80 years old who want some form of, like, organized, tell-me-what-to-do movement Ideally in a social format where you're with a group of people, you got out of the house. Like there are so many benefits. Like my grandparents used to just go to Costco every day because it was like a third place, right? It's like a place to go. They would walk around, they would see people, they could get like a $2 meal. Like, you know, it was, it was awesome. And so like, that was like a huge deal for them. And it's like, they don't really have third spaces the same way that like, you know, younger people have. So I kind of love this idea.

Yeah. It like makes a lot of sense. I'm surprised it doesn't exist already. I kind of did a little bit of research. I couldn't find anything. So I think there's something here.

Well, there's no like killer brand, even if obviously there's going to be something that exists. There's nobody's built like SoulCycle, who's built Barry's, who's built just like a really fun— and by the way, this playbook has been done 50 times now, right? Like Solidcore and F45 or whatever. There's like so many of these.

So many. Yeah.

You could just literally just copy the blueprint. You just change the demo. I also wonder if you could like get the insurance to cover in some way or like some way. Like, is there some like Medicaid?

Medicare Advantage plans should cover something. So there is, there's something called Silver Sneakers, which is a great name, which is a fitness program for older adults through Medicare Advantage plans. But it's like, it's not like a P90X, like digital or— No, it's actually, um, it gives members access to gyms. And actually my dad does this. I think that's how he pays for his YMCA. But it doesn't— it's not like they don't have this specific thing which I'm thinking about, which is like a boot camp around low-impact and senior-friendly stuff.

Right. This is great. Wait, so SilverSneakers, that's a private company and they're basically saying you get access to them. So they kind of class passed it. They went and did partnerships. Is that how they did this?

That's right. Yeah. And they do have— they do have like Online classes, but I, but it's different. It's like it's videos and then they have partnerships with gyms.

Is this like a venture-backed company or is this, uh, is this like bootstrap? They have 2 million visits a month on their website. It's pretty crazy.

Oh, interesting. They acquired Nutrisystem and South Beach Diet.

Yeah, this is interesting.

Like these guys, the SilverSneakers, like they're not going to do, you know, like the, the modern way of doing things. They're like an old school company. Right.

But this says here, 19 million Americans available to more than 19 million Americans through Medicare Advantage plans, supplement carriers, and group retiree plans. That's cool. Yeah, that's— there's definitely an opportunity here. I like these because I feel like with AI, let's look like, you know, with AI, you kind of want AI-proof businesses. If you're going to— if you're going to start something new, either you need to be a big beneficiary of AI or you need to be AI-proof. You want to be on either end of the spectrum. You don't want to be in the middle. And so AI-proof, like, you know, there's not going to be AI that works your body out for you. Like, even if it's, if it's smarter, it guides you, you're still going to have to do the workout.

Totally.

And so, and so giving people a place to go, especially if AI gives people more free time or more income, like anything like that, it could be a big beneficiary of that. I like this idea.

Yeah, it's a fun one.

Cool. All right, Shil, I appreciate you coming on and sharing ideas, insights, and all that stuff, man. Always good to hang.

Likewise, man.

That was fun.