The Exchanges

Q Especially earlier on, right? Maybe in year 27, the answer is different than in year three or two.

A Yeah. So I can only tell you what we've done, which is again, a little bit unusual. We pull out everything at the end of the year. Now, first of all, we're an LLC. So we're taxed on everything at a personal level. So if I leave money in the business, I'm still paying personal income tax on that money. It doesn't really make sense to do that. So we have a recurring, you know, recurring revenue model. We have very predictable revenue. So we basically have a little bit of overlap. You know, we take some money out in quarterly distributions and there's some money left over in January and we kind of wait till April to take it all out. So there's some overlap and there's enough operating cash, right? When we were, when I first started the business in 1999, we were, uh, an agency and we, our first client, it was, uh, four of us, three partners, one sort of employee. We each put 10 grand in, so we had 30 grand, uh, to start the business. Um, and then our first customer was, was HP. HP was like giving everyone business way back then. HP was like the hot company to get a gig with because they paid a lot. And I think the gig was a few hundred grand to do some website design for them. This is 99 where people are paying numbers like that. And, um, from that point on, we were profitable because we only had a few people. We didn't take big salaries, and that was that. We were able to pull out…

AI assessment note: “We were able to pull out all the money every year because, actually, we started”

Q And then you were with Mint, and then you were famously with Facebook. Um, were you cash poor for a long time?

A No, I, I've never been broke. I had a million dollars at 30 from day jobs. I think that's kind of, like, not recognized by most people. Meaning, one, I was super cheap. Right? So I lived on floors for a year. That's a good way to save money. Lived at my mom's house. Lived at my aunt's house. So just as, as cheap as possible. I did get two paydays. One payday was from the Gambit payments company. So I think I made around 350,000. That was payments for Farmville and all those annoying games. Uh, and then the conferences. So those Plus just being really conservative with the cash. Like it was about a million dollar liquid around 30.

AI assessment note: “No, I, I've never been broke. I had a million dollars at 30”

Q the spider and that's, you know, that's where he got his powers from. I think your origin story is amazing and not, not a lot of people know the full story. Can you take me back? You're 17 years old. I think you're a part-time janitor and you'd never been to a seminar in your life. How did you, what was your spider bite? How did you stumble into this?

A Well, it's an interesting question. I was already interested in personal development because I had a kind of a rough background. I have four different fathers. We had no money for food. I had to work two jobs, work as a janitor. And my mom had a friend and dad had a friend that had been my, my dad, my dad's description was he used to be such a loser and now he's really successful. And so he called and said, listen, I hear your son's gotten big. I was, I was five one in high school and I was six two by my senior year. I grew 10 inches in a year. I tell people the difference is personal growth, by the way. But the bottom line is he said, you know, I, I gotta move some furniture and things. I heard he's big, you know, could he come work for the weekend for some extra money? So. I did. I worked really hard and the guy really was impressed by my work ethic. So he said, I'm gonna take you to lunch. And we'll go to this lunch and you know, and he's saying, you know, I, I really think you go places. You got a lot of drive. And I said, well, I'd like to ask you some questions. And he said, okay. And I said, my dad used to say you used to be such a loser and now you're so successful. How'd you do that? You know, only a kid can say this, right? I wasn't trying to be cute. I just literally repeated it. He goes, you never said what? And then he's like, well, it's kind of true. And he said, …

AI assessment note: “he said, well, I went to this seminar and I said, what is this seminar?”

Q Going to a salad bar. You're 24 years old. You're broke. And you had a giving moment that sort of shifted you. Would you please just tell that one? Because I think giving is not something you got to wait till you're rich to do, which is I think the common misconception.

A I tell people, if you won't give a dime out of a dollar, you're not going to give ten million out of a hundred million or a hundred million out of a billion. Don't kid yourself. Right. And also the value of giving Transforms you out of scarcity, but the background on it is I was working for Jim Rohn, this personal development speaker, and I really did well, and then I did poorly for a while, and I was really frustrated. I was working hard. I wasn't getting the return. I was totally broke. You know, you're in business. You make some mistakes, and I found myself totally broke again, and I'm in this 400 square foot bachelor apartment in Venice, California, feeling sorry for myself, and watching Luke and Laura on General Hospital. It was just terrible. And, um, I'm down to my final, you know, 1920, 21, 22 dollars. I know it wasn't some change. I haven't paid my rent, and I gotta figure out what to do and what to eat, so my focus was, okay, I'm gonna go to this all-you-can-eat salad bar, taco bar, and I'm gonna load up for the winter, um, and, you know, spend five bucks, and then, you know, and then I didn't drive there because it was only about three miles, but I couldn't pay three bucks for parking, too. It was just, I couldn't do that, so Anyway, long story short, I get to the place. It's on the water in Marina del Rey. It's why I went there. There's boats going by, and I, I can'…

AI assessment note: “the background on it is I was working for Jim Rohn”

Q That's amazing. And so, um, so you do that. What is the, like, uh, you know, what's the product or what are you guys actually building?

A We are building, uh, several companies under this whole code. So the first company we created, um, is called Seljabu, and it's essentially a company that will help overcome drug resistance. And, um, how do I make this more concrete? If you're taking, uh, drugs for your leukemia, or you're taking chemo drugs, It might be effective in work for wealth. You have lots of drugs that are effective in work, but then one day they stop working, and when they stop working, um, unfortunately, there are sometimes no other viable options for the patient, which means they're gonna then die, but a month late, a month earlier, the drugs were working, and they were fine, right? So that's one company, there's another company that's developing, um, It's programmable human biobots, and in fact, this got, you know, there's an article about this in Nature as of today, and that company is called Anthrobots.

AI assessment note: “We are building, uh, several companies under this whole code.”

Q do an analogy? Uh, you know, Pomp going from Bitcoin laser eyes to Real estate and all kinds of other shit that he's doing now. Is it, uh, is this Justin Timberlake from NSYNC now going solo Justin Timberlake? You know, what, what's the, what's the right analogy here? Who, who has made such a transition, such a life pivot like this? Is there anyone that's done this in Hollywood?

A Well, here's the thing is, uh, it's not really a pivot if you kind of expand out off of the internet, right? So if you think about, I started my career building companies, then I went and I worked at Facebook, uh, then I started investing. And then once I was investing, that's really where, uh, kind of the Bitcoin stuff happened. Um, but even the stuff on the internet, I worked directly with, you know, Mark Zuckerberg and Sheryl Sandberg for a short period of time at Facebook when they were trying to figure out how do they grow their audiences on Facebook? I remember early on when Fuck Jerry, the Instagram account, they were trying to go from Instagram and figure out what's their Facebook strategy. And so the reason why I say that is like, I don't know, think of like a Kim Kardashian. She goes from like sex tape to reality TV star to like entrepreneur, billionaire to now like criminal justice reform to I think she's going to be president of the United States one day. Uh, and you look at that and you're like, actually the same thing that makes the sex tape go viral gets you elected to be president today. So like in some ways it's actually the exact same skillset, just, you know, packaged up in a different way and, uh, with different ambitions or, or aspirations.

AI assessment note: “think of like a Kim Kardashian. She goes from like sex tape to reality TV”

Q I'd rather be honest. Okay. Pump, you brought some ideas for us. You know that this is the idea podcast. Um, you brought some ideas. Let's rattle them off. So, uh, start with number one. What ideas and trends or opportunities do you see right now in the market?

A Yeah. So this, uh, this first one is one that we're actually doing. Um, so I've thought a lot about it. Housing affordability is the worst it's been in, uh, this century. Um, we continue to see people are worried like, Hey, I want to buy a house. Should I rent? Should I buy? What are interest rates going to do? All these different things, but there's no dominant voice in terms of news commentary and data. Um, and so we started a company called Resi Club. Uh, the idea really in the beginning is just go educate people about What is happening? And so, uh, I'm not an expert on residential real estate. Uh, I don't know that many other experts on residential real estate. Um, so we were able to partner up with a gentleman named Lance Lampert. Uh, Lance was the real estate editor at fortune magazine. So he's like quote unquote legit, right? He's got 75,000 followers on Twitter. A lot of people in the industry all follow him. And we basically just said to him like, look, man, we want to go build the dominant platform in residential real estate coverage. Why don't we do it together? We know how to scale things. We know how to grow this stuff and monetize. You know, the content, you are the expert. Um, and so let's partner up. And so we've gone ahead. We got started. It's about two months old. Um, and you know, I love these types of businesses because they kind of look stupid almost in th…

AI assessment note: “there's no dominant voice in terms of news commentary and data. Um, and so we started”

Q You bought them all at once or like one at a time? Like you bought a chain?

A All in one pot. So essentially there was, there was a kind of a patriarch of a family who had built up a portfolio about a 120. He passed away. And then, um, basically I think it was the trust or the estate, I don't know which, which, but he was, they were selling them off in blocks. Right. And they don't want to sell off like one at a time because it's a 120 because the kids, they had a tax bill coming up because the inheritance, yada, yada, yada. So, um, this actually is, is this started with Nick Huber and Mitchell, um, Ballbridge, um, of the cost seg world, because they started talking to me about, Oh, there's, there's some tax implications where if, if your partner, your wife or your husband is a real estate professional, your passive losses on like real estate become active losses and they offset active gains. So got a big pile of, you know, kind of gains from the sale of the company. And then all of a sudden I can offset those with depreciation of the gas stations. And I can do that with bonus depreciation in one year. So just to use some round numbers, like if I buy ten million dollars of gas stations, I basically can take eight million of depreciation essentially, and that can offset some of those particular gains. And so in October, September, um, Nick starts telling me about this. I start talking to Mitchell trying to figure it out. I start talking to tax lawyers. Al…

AI assessment note: “All in one pot. So essentially there was, there was a kind of a patriarch”

Q If you had to summarize your learnings with pricing, is there like two or three bullet points where you'd be like, just do these three things and you're 90% there?

A Sort of, um, but with, like, giving you a little bit more bulleting, um, you should be changing something about your price every three months. That does not mean raise your price every three months, but it means, like, changing up your packaging, going up market, down market, changing up an add-on, changing up your discounting strategy. It's this forgotten growth lever in most businesses. You acquire customers, you monetize them, retain them. We focus probably 60% of most budgets, more so in D to C, less so in B to B, on, like, basically acquiring customers. We spend a little bit of time on retention. We spend like no time on pricing. So change something every three months. Um, one of the biggest hacks that's easy to talk about on a podcast, add-ons, um, they're the most underrated, underutilized aspect of all pricing, consumer B to B enterprise. Um, they boost lifetime value by about 20 to 50%. So just to make sure this is clear, like, hey, they bought your core product, which is a fitness shirt. Well, add a white t-shirt for 10 dollars, like stuff like that. Those are like add-ons. Hey, they bought, Your SaaS app, add priority support for whatever, 10% of your list price is for the, the software. Um, most companies, like the most high growth companies, at least in the subscription space, they have 12 or more add-ons typically. Customer never sees them, all, all 12 of them, bu…

AI assessment note: “you should be changing something about your price every three months”

Q And why do you, uh, what do you think, what do they say to you? Where, where, how are they finding you, and what do they say to you?

A Some people beg me to talk to them for 15 minutes. They'll offer, someone specifically offered me 500 dollars for five minutes of my time, and it's crazy because I'm so irrelevant most days. I'm out in Sutton, Massachusetts, so there's not much happening here. I'm kind of under the radar, and so all of a sudden, I've now gotten a ton of inquiries from people, and a lot of people want specific information. A lot of people are emailing to say, hey, I'm doing this exact thing. How do you get financing? Or, can I get your opinion on this business deal? Or, I'm about to close. How did you get a bank to actually do your deal without putting much or any money down?

AI assessment note: “A lot of people are emailing to say, hey, I'm doing this exact thing.”

Q a, um, A behavioral observation. So just a behavioral phenomenon. You notice people doing something, or you notice the pendulum swinging, or people used to feel one way, or the popular sentiment is one thing, but you notice people starting to gravitate towards the other end of that, uh, of that spectrum. That's usually where there's like a real, real opportunity. So what's, what's an observation here that you have?

A Yeah, so, so if people don't know the Trad Wife movement, I find it fascinating, and basically how I came across it, as one does, As I was on Instagram, scrolling my life away, and I saw this, like, beautiful woman, flowy dress, no shoes, running through, like, what I could only describe as a field that was her house. And, um, and overlaid on top of it, she had, like, her little child in front of her, and it was like, girl boss, question mark, I want to be a hobbit mama. And I was just, like, giggling kind of ridiculously at this, and then I thought, ah, I kind of, I kind of feel that. Like, I feel like, We, we know from COVID everybody like wanted to go be a gentleman farmer, right? I think you guys talked about that, but this is like the two point O version. And so what happened from this one video I saw is that Instagram realized I watched it longer than I guess I do other things. So I got served up all this stuff. And boy, before you fucking know it, uh, Sean, I buy some white pumpkins, some flowers to press onto them. And I'm fucking gluing pansies on a pumpkin. Now you actually know me. They're like, I don't have hobbies. Like all I do is work. We run a bunch of businesses. I'm like, not that fun. And I'm, I'm sitting in front of the TV gluing pumpkins, and that's when I realized, I think this is gonna be huge. So I looked up the TikTok views for this search of Trad Wife,…

AI assessment note: “if people don't know the Trad Wife movement, I find it fascinating”

Q brand more than being Scott Galloway, the founder of like, are you enjoying it more than being an operator of companies or are you enjoying, uh, I mean, you have some cool blog posts where you're like, when people say hi to me in the streets, I love it. It makes me feel great. Which one are you enjoying more? Scott Galloway, the brand or Scott Galloway, the business person?

A Oh, on the whole, this is really wonderful. I mean, people come up to me. And are super nice, and you know, I'm at that age, I have 13 and 16 year old boys, so everything I do is just like tragically uncool in their eyes, and they don't really seem to like me a great deal. So when someone comes up to me, it happened yesterday, and like wants a picture with me, and they're excited to meet me in front of my boys, to be honest, it just feels really nice. And people, generally speaking, are just so nice, and they come up, and I get to meet new people. Yeah, it's awesome, and it feels very gratifying. I'm also, We talked about addictions. I'm addicted to affirmation from strangers. It's sort of pathetic, but I at least know it so I can modulate it. And it's really wonderful. People are really friendly and really nice. Uh, you know, I went to the Arsenal game with my boys and a bunch of people came up to me and said hi. And I was at the Taylor Swift conference, uh, concert and the six year old girl had made me a bracelet and came up and gave me a break. I mean, it's just like, I have all these wonderful moments with strangers. So. It's wonderful. I do think there is an algorithm for happiness, though, a pretty good one, and that is to be rich but anonymous, because at some point I'm going to become the villain. And some of the things you talked about before, there's an entire industr…

AI assessment note: “Oh, on the whole, this is really wonderful. I mean, people come up to me.”

Q for 50 years, but they're so big and the founders are dead. And so I like, I'll go and like read the biographies, but I'm like, I don't know even know how you started this damn thing because like it's been lost in 50 years of history. How is, how does your, what's your research business providing the user and how, how do you operate it? How does it work?

A Basically in crypto there are these things called protocols like Uniswap and Aave and Compound and then there's like these layer ones like Ethereum you've probably heard of, Solana, all these other things. The industry's moving from treating these protocols like they're these like weird esoteric things To treating them what, like what they are, which is just businesses. So MakerDAO, for example. They'll do a hundred million of revenue this year. That is a business. They have like people they pay, like employees and contractors, profits, costs. That is, nobody talks about them like that. So what Blockworks Research does is it's a platform for investors who allocate to crypto assets to basically look at, uh, these crypto protocols and look at their user metrics, financials, get research on them. We're very early to trends. With what's happening with the protocols, you can look at the governance. So like, if you want to look at, uh, who's voting on different proposals, if you want to look at like how people are, how people like, who are the big stakeholders inside the protocol, you can look at all of that inside the platform. So it's probably not useful to you. It's incredibly useful if you're a crypto fund who alloc, who has like two percent of their portfolio in, in crypto. So.

AI assessment note: “what Blockworks Research does is it's a platform for investors who allocate to crypto assets”

Q No. Is it, wait, is he a, does he, does he spell his name funny? Does it actually start with a T?

A It does. It does. So, all right. So Peter Turchin is this historian and mathematician. He developed this field called, uh, Clio dynamics, and he kind of studies the, you would like him. He's a history guy studies, like the cycles of cooperation and conflict amongst elites and societies throughout history. And his argument is that. Periods of internal peace and cooperation are disrupted when the population of elites grows too large, and then competition emerges among them for what is actually these limited elite positions, which then, because there's too many elites and too little positions, that leads to infighting in the elites as they try to maintain their wealth and status, and it causes social instability and a breakdown in cooperation, and it doesn't, historically, that Breakdown, cooperation, social instability does not stop until there's a crisis like something big, right? State collapse, revolution, whatever it may be. And then a new, new cycle of cooperation resumes. So I don't know if you tend, like, if you look at history, you can cut, you can see history through the lens of whatever lens you want to see it. There's like the The fourth turning, which is like these four big periods, and you can explain it like that. There's like this Peter Turchin, Clio Dynamics view, but one thing I believe is like, crypto is a better way out of this whole system.

AI assessment note: “It does. It does. So, all right. So Peter Turchin is this historian”

Q like a product that you could eat, you could drink, um, that wasn't software based and, but still was innovative. And so it was like kind of in this mix. And I remember Andreessen Horowitz got behind it and some others. And so it was very interesting thing. And I think it started out of like a hacker house, right? Like you guys had a crazy house. Is that right?

A Yeah. Uh, I mean, a bunch of funny stories from that. This was the, yeah, Warby Parker was like the first e-commerce company to kind of think about it from like a tech first angle. Uh, we were a couple of years after them, um, right around the same era as like Dollar Shave Club, if you remember that company. Um, but yeah, we met in a hacker house. Uh, my, my co-founder and I, we went to preschool, middle school, high school together, went to college in the same city. And so we move out to Silicon Valley. We're looking for a place. We find something on, uh, like Craigslist. It's like an Airbnb listing. And they're like, this place is incredible. It's got a pool. It's got five bedrooms. It's exactly like the social network. You're going to love it. We show up. The pool is filled with algae. The bathrooms don't work. It's just absolute squalor. So we grind for like six months there. Eventually we moved to the tenderloin, which is an even nicer community. And And, uh, we're living in technically a one bedroom with three guys. So I was living in the living room. Another guy, uh, Rob, the guy who actually came up with the idea for storyline, he was living in what was technically a closet. Cause it didn't have a window. And we were just, we were just hacking.

AI assessment note: “we met in a hacker house... We show up. The pool is filled with algae.”

Q John, you, uh, you're cool because you, um, I think you're like us, uh, but maybe even more extreme in the tech world and that you have your foot in the startup world and you're hanging out with these big wigs, but you're also can just joke around and shoot the shit and like you're pretty self-aware. Who, uh, what do you align with? Who do you align with politically?

A Oh, uh, yeah, I, I really like this guy, Mark Hurd, who's a Republican from Texas. Uh, he was, uh, he's a smaller candidate, so he's not polling super well, but he worked for the CIA, and he also was on the board of Palantir, and he would be the first computer scientist president, and I think that that would just be very, very interesting to see someone with a CS background. Obviously, I love programmers, and I, I think that they think about the world in very interesting ways, and we've had this very long, long arc of, you know, lawyer, lawyer, businessman, lawyer, lawyer, lawyer, right? Like, that's the story, and he's like a younger guy, so, uh, I'm, I'm proud to endorse him.

AI assessment note: “I really like this guy, Mark Hurd, who's a Republican from Texas.”

Q Wasn't it basically just like Gilbert comics or was it?

A Exactly. Yeah. Dilbert comics. And, and we had other comics. We own peanuts and a lot of other ones, but on a relative basis, it became very successful as a website. We sold, uh, advertising, uh, e-commerce. Uh, so things that were not that easy to do because we didn't have the vendors at the time. So I went to the parent company and said, look, we should build up an internet division. And they said, no. I thought, you know, I actually believe that the internet's going to be a huge, which is obvious now, but you know, a huge part of the next 25 years. I want to go do this full time. So I was going to go start a company. I ran across DoubleClick that was already in the ad tech space. They committed me to join them instead of starting my own company. I became the CFO, the president, and then the CEO.

AI assessment note: “Exactly. Yeah. Dilbert comics. And, and we had other comics.”

Q choices people make when, um, when it comes to a funeral. And this is like, that's a one chart business. You can look at nothing else and say, all right, I know there's, I know there's opportunity when I look at a chart like this. Um, is, is that, does that jive with your way of thinking or do you have anything you could add to our understanding of that?

A No, no, absolutely. I mean, I'll give you another one. The cost of labor is going to just keep going up. And so, you know, waiters were paid 15 dollars an hour. Now it's 20 to 25 dollars an hour in New York. Unless we change immigration or something fundamentally changes, that could be 30 dollars an hour. So you know what? Over time, that changes the calculus of automation. Whether it's making french fries, whether it's through this, we're all going to have to find ways to use less labor. And so when cost of tech goes down and the cost of labor goes up, what does that tell you? More automation is going to happen. Uh, so I'll bet on that trend all day long. You know, we're an investor in a company that gives robotic massages. There's 17,000 open positions for massage therapists in this country. And so, you know, there's hotels that just can't offer massages because they don't have the people. So, you know, we hope they're gonna offer a massage. So that is just one example, but I have 10 others.

AI assessment note: “No, no, absolutely. I mean, I'll give you another one.”

Q And what's the, what's the stick? It's like at a chicken shop.

A It's a date. Yeah. It's a date at a fried chicken place in London. And the chicken shop in London is like the last place you would go to have a date. So there's comedy in it. She's a comedian. Um, and through, yeah, through this, it's just had like, this has now spun her into essentially creating her own production company where Brands come to her and say, we love your shtick. We love your comedy. We love the way you've created this show. Um, like this show has no advertising in it, no advertisers, and we'll never have advertisers. And this thing does, you know, the Jack Harlow episode has fifteen million views. Um, this regularly does, you know, one to five million views in the first week, um, but no advertisers. And what it operates as is like, it's a production company. And Nike just came to her.

AI assessment note: “It's a date at a fried chicken place in London.”

Q Um, so like when you look back on that phase, is it just like, um, Cringe, and I don't want to ever think about, like, I hope my, I forget about that. Is it like, no, that was actually really useful for me in these ways? Is it just funny now? Like, what's your reaction now?

A It's a really good question. I w I would say it's probably like one third cringe, one third. I think it was actually really important and informative in a lot of ways. And then one third just kind of funny and just like, can you believe that happened? Uh, I actually, when I moved out here to LA, um, I met up with Neil for the first time and we spent a day together and we spent like half the day just kind of being like, can you believe that happened? Right. Can you believe we actually did that? I, I look back though, especially now that a little bit more time has gone by, I really do think there, there was kind of an underrated factor. And I think this is very relevant because this is starting to happen again with Gen Z with I think the pickup artist industry is underrated as a cultural or social phenomenon, particularly for young men trying to find identity or find themselves in like a very confusing world with a lot of information. Uh, because it's, when I look back at that time, like, yeah, like we, In the industry are the coaches. We used to joke with each other. It was like, yeah, we all came for the women, but we stayed for the, for the other dudes. It's most of the guys who really got into that. It wasn't about the girls. It was, they needed to feel accepted and, and, and validated by other men. And, and just, I guess, I don't know their masculinity, right? There was like…

AI assessment note: “I would say it's probably like one third cringe, one third. I think it was”

Q That's so true. So you're doing this, this, uh, series. What's like the craziest or most interesting challenge? I guess you can't give it away too much, but like what, what concepts are like, Ooh, I can't wait to see how that's going to turn out. Or like, I really want to try something like this.

A A lot of the, the social stuff is like the most Interesting. Cause it's, you can do a lot of fear based stuff. I mean, you can take somebody up in a plane and throw them out, you know, make them skydive or whatever. And that's exciting. But like, I don't know, it, it doesn't feel like there's as much depth as like the social stuff. So, uh, we have a challenge in another video where I printed out flat earth flyers saying like, you know, do you, do you know the truth about the planet? You know, it's a picture of a flat earth. And I made her Go into a public place and hand them out to people.

AI assessment note: “we have a challenge in another video where I printed out flat earth flyers”

Q I'm in the mood to buy like a, a fast car. Like let's go, let's sort by speed in the category of, um, weekend. Yeah. And, but I gotta like go to Excel and I've gotta like do like a, like a, like a, like a row freeze. It's so complicated. Why don't you make this more like robust? It's a really, this database could be a business in itself.

A I know. I agree. I should do more with it. To be fair, the Doug score came out in like mid-seventeen. And for the first two years, it wasn't really all that valuable because it didn't really have that many cars in it. And so like late 19, it starts to become pretty valuable. And now there's gotta be like a thousand data points in there. But what happened was I launched cars and bids. I just priorities had to kind of take shape and yeah, I probably should do more with that because I think it's valuable also. And I think the really valuable thing would be able to be to sort by like type of car. Like if you want a fast wagon, put up all the fast wagons and then you can just have that. But that's something that you could do at home. I've decided, I've decided I'm going to just do the videos and spec. I'm a big fan of specialization. And so I decided I'm going to do the videos and we're going to let other people. And sometimes people email me. They're like, I just did this great data project with all the Doug score data and here it is. And I look at it and it's really cool. And it's like, I should be doing that, but I'm not.

AI assessment note: “what happened was I launched cars and bids. I just priorities had to kind of take shape”

Q if people have seen it, it's a whoop band you've, uh, you have to have seen it on people's wrists, but you said something like we started with high end athletes. I think I read something like this, that is this right? That LeBron and Michael Phelps were two of the first hundred customers or users of whoop. Is that, is that real? And how did, how did that happen?

A That is real, and this would have been around 2014, 2015, so, you know, we spent about two to three years, really, on the initial V-one of Whoop, and, you know, I wanted to start with the best athletes in the world, and really for two reasons. The first was that we were bringing sleep and recovery technology to market for the first time, and I felt like professional athletes who Uh, you know, have to perform on a daily basis should really understand how they're recovering. That was one of the insights to starting the business. And, uh, and then second of all, if we could get the world's best athletes to wear, uh, whoop and organically like it, then we could build a whole brand around, uh, performance that ultimately could, could scale to, to consumers. And, and I grew up very inspired by, um, brands like Nike and, and the Jordan brand and, and just how, Like a swoosh on something could make, make the whole product feel completely different, independent from anything else about the product, uh, just because of the, the storytelling behind it or the brand behind it. So I was interested in how health monitoring could have a brand to it. And, uh, and so that, that was really the thesis for targeting professional athletes. And, uh, and so in the case of getting to LeBron and Phelps, the, I think the key insight was, Finding people in their lives who had a big influence on them, who …

AI assessment note: “That is real, and this would have been around 2014, 2015”

Q What, uh, we'll take on those athletes. Do you think it's a sort of like intentional thing? Like you think that they, you know, like is LeBron or Alex, are they doing something that's making their sleep that much better? Or do you think because they happen to be great sleepers that that is what allowed them to become such great athletes or such great performers?

A I mean, there's certainly, there's certainly genetic things that make people better or worse at sleeping, but, uh, there's also so many things that you, the individual can do to enhance your sleep, uh, sleeping at a very consistent time. So going to bed and waking up at a very similar time, we'll just, um, we'll just unusually elevate the quality of, of your sleep. Often sleeping in a very cold room, a very dark room, a very quiet room, a room of high air quality, Athletes who are serious about this stuff will, you know, measure all of that and dial it in. I still think athletes aren't sophisticated enough about sleep and recovery, given how important it is to their overall performance, but those are a variety of things you can do. We talked about blue light. There's certain supplements that work better or worse for people, magnesium, melatonin. Interestingly, hard, harder, harder sleep drugs, like the ambience of the world, Uh, they, they knock you out, so your sleep latency is short, but the quality of the sleep, uh, is never that high. So again, back to that percentage of time that you're in REM and slow wave, it, it is rarely, you know, maybe if you're someone who would normally be at 30%, you're going to be at 20%.

AI assessment note: “there's certainly genetic things... but, uh, there's also so many things that you, the individual can do”

Q but before that you did it with poker. Before that you did it with other stuff. And like, we'll go into some of those funny, funny stories in a second. Um, but that's your guys' secret sauce to which I was like, why do they need a newsletter? The newsletter doesn't do that. That's not, that's not the answer. But there is some, I don't know, synergy there for you.

A Yeah, so it's, you know, just this brand component of, like, Google has really moved towards rewarding brands that users are actually going to Google and searching for. Like, Milk Road is being searched hundreds of times a day, and that's such an indicator to Google of, like, humans are interested in this brand. Same with JM. JM's getting thousands of searches a day for JM Bullion. So, like, when we were building our sites, like, defirate.com was the one that we merged into Milk Road. No one's out there really looking for this site. You know, we're just trying to figure out how to get it up in Google, so eventually it Will become a brand. So for us, it was like, Hey, we're, we get to jump forward, you know, a year in this journey. If we buy this newsletter by the website, roll it in and then, you know, reap these benefits forevermore. You're going to continue to get really amazing backlinks because you do all these awesome interviews. Um, it was, you know, that was my, my piece.

AI assessment note: “Google has really moved towards rewarding brands that users are actually going to Google and searching”

Q Uber credits and all that. So how did you even figure out this was a thing? Uh, I want to hear that for both of you guys. Cause this is, this is y'all's game and it's a game I didn't know about till much later in life, but you guys discovered it kind of early. I want to hear the origin story. How did you guys even get into that?

A Yeah. So this was like during like the moneymaker, you know, world series of poker was a big thing and you know, All of my friends and I were playing poker just around the house. And then online, you know, there was a bunch of poker sites and I saw one of the poker sites had like a poker chip set and they would give it to you for free. And I was like, well, how does that work? Nothing in life is free. And I figured, oh, they're giving it for free because they're getting like 250 dollars per person they end up sending. So at that point I was like, perfect. I've got a lot of friends. And I'm just going to kind of make the difference. I'll give them 50 bucks to deposit and I'll make, you know, the 200 dollars that I get paid from the, uh, you know, casinos and sports books and poker at that point.

AI assessment note: “I saw one of the poker sites had like a poker chip set”

Q there was like this like small community of people in Silicon Valley that were like using it back when it was like texting The, the, your updates out. Um, like when you're, when you were writing that check, did you feel like this is the, you know, the next big thing or was this kind of like, I don't know, my friends are smart. Let's see. Or where was it?

A I felt like it was the next big thing because there was, I loved. So as someone that was building a social graph of sorts at dig, you know, there was always this idea back prior to, um, excuse me, prior to Twitter that was, um, Bi-directional friendships. So, you know, on MySpace and Friendster and all the others that had come prior to Twitter, you had to actually know the person to see their content. So it was like, I, would you like to send a friend request? Yes. Do you accept this friend request? Yes. Right. And it was like, same thing with Facebook. And when Twitter came out with that model of just this idea of following and, and, and it allowed, um, Like, there was no celebrities on the platform. It was like me and Lila Port and a couple others that were the top followed people on the platform at the time. Um, but I, I, I thought to myself, like, wow, if this catches on with the celebrity crowd, it's just going to be insane. It's going to be because everyone will just want to see. And also the barrier to entry. A lot of back then it was, it was, um, it was impossible to get, uh, you know, celebrities to sit down and kind of, Um, do technical things because we didn't really have smartphones, but the fact that you could text to that number, that short code, just what you were up to, anybody can do that. It doesn't require any special software. It doesn't require you sitting …

AI assessment note: “I felt like it was the next big thing because there was, I loved.”

Q Yeah. Do you like have like rules for what you're looking for?

A Yeah. I mean, it's, there is, um, I guess the, the question really comes to when you decide to kill something or sell it off or get rid of it or move on to the next thing. And, and oftentimes it's, um, because your original kind of thesis around either the market size or just the concept behind it just didn't take hold. And so I don't have any like hard set number of months. Sometimes you're early. So, you know, uh, the fasting app, for example, Um, you know, when, when I launched Xero, it, it sat at, you know, tens of thousands of users for the first eight months, and then fasting hit, and it became more of a household thing, and people were talking about intermittent fasting, it was all over TV, and different, you know, places were picking it up, and so people were just naturally searching for fasting in the app store, because that's just what they do, and then that's when it exploded to, you know, hundreds of thousands, and, you know, a million plus monthly active people doing fast, um, And, but it was, had I shut that down after the first six months, um, you know, it had been too soon. So something like that, if you, if you just believe the market is not quite mature enough, I typically put it into a little bit more of a maintenance mode. You know, I got it to that first version where I felt like this is a useful utility for people that are looking to learn more and get int…

AI assessment note: “I don't have any like hard set number of months. Sometimes you're early.”

Q like this boat marina thing. I'm like, that's a whole conversation. Like how on earth do you discovered that? And then I'm sure you have strong opinion. You just have Uh, very, and then now obviously you're doing government stuff and you've done, uh, and you have no bunch about politics, whatever. How are you becoming so well versed and also so opinionated on such a broad set of topics?

A Because you have to most of the time, like the best things that I've done that I have done in my career have not been going super, super deep on one vertical and then finding the really, really hard gains that are at the end of a long fight that everyone's made. Like an example here would be, uh, with just like optics technology. Most people are fighting way at the end of the spectrum where they're trying to like, oh, we're using new cutting edge materials that increase The ability to control light more precisely by two percent. And we're trying to figure out the physics of how we can manufacture these polymers. Most of my best ideas have not come from that. They've been from knowing things in totally different fields that have nothing to do with the field, or at least people don't think they do. And then pulling ideas from those fields and applying them in a new way. Like the, the, the really key thing that made the Oculus Rift work is just one example, rather than focusing on trying to make these Optical stacks that cost thousands of dollars and weighed a bunch. And that was really what was making these headsets, uh, weigh many pounds and cost tens of thousands of dollars. It was the high end optical stack that was able to project images on your retina with minimal distortion, but you needed, you know, a bunch of lenses. They're all very, very expensive, very high precision. …

AI assessment note: “knowing things in totally different fields that have nothing to do with the field”

Q some art here that you got going on, Sean. I love it. Um, okay, cool. Let's rapid fire through one more each. Um, let's see. So Sean, we have your clubhouse one, but I feel like it's pretty close to the metaverse one as to why that work. Um, do you want to talk about, uh, this Elon one, or do you want to talk about, uh, this learning one?

A Uh, yeah, I'll do both real quick. The Elon one is actually like Sagar was saying. I, uh, I, I, one of the threads that went viral was not, no original insight. Uh, Elon was on clubhouse. Elon like popped onto clubhouse when clubhouse was hot. And, you know, just a guest appearance by Elon Musk is not something you get very often. And also clubhouse was like overload. It was like invite only and it was overloaded. So I just go for those who are locked out of the Elon thing. Um, here's what he's saying. And I just live typed and transcribed everything interesting he was saying in a thread In real time. And I was the only guy doing it. And like, you know, on one hand, I felt a little silly. I was like, oh man, I've become like a professional note taker on a fucking beta app of clubhouse. Like, geez, what does my career come to? And then also I was like, oh wow, that's just like 7000 likes already. Okay. Nevermind. Let's shut up. Like go. And so, uh, you know, I just like just did it, but it was like, it talks about that same thing, which is like, some people think they need to have this like Really great insight or amazing, you know, perspective or whatever. And sometimes you're just providing a service better than others. You're just clipping good content and you're posting it and you're doing that consistently and people will follow you for that. You can build a huge audience a…

AI assessment note: “Uh, yeah, I'll do both real quick. The Elon one is actually”