#479 Jeff Morris Jr on Investing In Product Companies

Jeff Morris Jr is the founder and Managing Partner of Chapter One. He was previously the VP of Product, Revenue at Tinder In this conversation, we discuss the product thinking that built the highest grossing app in the app store, why Jeff is so product focused as an investor, what makes a good product, and what Jeff has learned as a solo-capitalist. ======================= The Stacks 2.0 mainnet launched on January 14, 2021. Stacks, which you may recognize as Blockstack, is a layer-1 blockchain that uses the Bitcoin blockchain as a secure base-layer and enables developers to harness its power in new ways. Stacks makes Bitcoin more than digital gold, enabling apps and smart contracts on Bitcoin--unlocking innovation, new value, and a new way to earn BTC. Visit http://www.stacks.co for more information. ======================= Coinbase Wallets are adding support for .crypto and .zil domains through their partnership with Unstoppable Domains. Unstoppable Domains provides an all-in-one solution for blockchain domains. You can send money using these new domains instead of long Bitcoin wallet addresses, while also storing your domain in Coinbase's collectibles section. Go to unstoppabledomains.com in the dapp browser to register and manage your domains. ======================= Pomp writes a daily letter to over 120,000 investors about business, technology, and finance. He breaks down complex topics into easy to understand language, while sharing opinions on various aspects of each industry. You can subscribe at https://www.pompletter.com =======================

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:02Anthony Pompliano?

  What's up everyone, this is Anthony Pompliano. Most of you know me as Pomp. You're listening to the Pomp Podcast, simply the best podcast out there. Let's kick this thing off. Jeff Morris Jr. is the founder and managing partner of Chapter One. He was previously the Vice President of Revenue Product at Tinder. In this conversation, we discuss the product thinking that built the highest-grossing app in the App Store, why Jeff is so product-focused as an investor, what makes a good product, and what Jeff has learned as a solo capitalist. I really enjoyed this conversation with Jeff, and I hope you do as well. Before we get into this episode, though, I want to quickly talk about our sponsors. First up is Blockstack.

• 0:44Anthony Pompliano?

  Apps and smart contracts are coming to Bitcoin along with a brand-new way to earn Bitcoin. Stacks 2.0 will give developers powerful new tools, including a smart contract language called Clarity that was made for Bitcoin and jointly developed with Algorand, as well as a new consensus mechanism that rewards the network with both Stacks tokens and Bitcoin. Stacks, which you may recognize as Blockstack, unlocks new use cases and functionality for the world's most secure blockchain, Bitcoin, without modifying Bitcoin itself. The door for developers and entrepreneurs to activate the billions of dollars of capital currently passively held on Bitcoin are now wide open. Proof of Transfer, or POX, is the groundbreaking

• 1:27Anthony Pompliano?

  consensus mechanism that makes this all possible. POX connects the Stacks blockchain to Bitcoin, opening up STX mining on the network and enabling stacking, where STX holders can earn regular Bitcoin rewards for supporting consensus, Stacks, apps, and smart contracts on Bitcoin. You can visit stacks.co for more information. Again, stacks.co for more information. Next up is Unstoppable Domains. Unstoppable Domains has partnered with Coinbase Wallet to add support for .crypto and .zill domains for that Coinbase Wallet. Unstoppable Domains provides an all-in-one solution for your blockchain domains.

• 2:10Anthony Pompliano?

  You can send money using these new domains instead of sending the long Bitcoin wallet addresses while also storing your domain in Coinbase's collectible section. So no longer do you have to send that long string of letters and numbers. You now can just tell people, "Hey, send me the Bitcoin to pomp.crypto." That's right, I have pomp.crypto. Nobody else can get it. So if you've got the name of a domain that you want, go to unstoppabledomains.com and buy it today. If you don't buy it and someone else does, you can't get it. So whether it's your personal name, your company's name, maybe something you think will be valuable in the future, whatever the domain name is, go get it at unstoppabledomains.com today. If somebody gets it before you, then they got it, you don't. So go to unstoppabledomains.com

• 2:55Anthony Pompliano?

  and get and register and manage your domains at unstoppabledomains.com. Lastly, don't forget that I write a daily letter to over 120,000 investors about business technology and finance. I break down complex topics into easy to understand language while sharing my personal opinion on various aspects of each industry. You can subscribe at pompletter.com. Again, pompletter.com. All right, let's get into this episode with Jeff. I hope you guys enjoy this one.

• 3:26Speaker 01

  Anthony Pompliano is a partner at Morgan Creek Digital. All opinions expressed by Pomp or his guests on this podcast are solely their opinions and do not reflect the opinions of Morgan Creek Digital or Morgan Creek Capital Management. You should not treat any opinion expressed by Pomp as a specific inducement to make a particular investment or follow a particular strategy, but only as an expression of his opinion. This podcast is for informational purposes only.

• 3:58Anthony Pompliano?

  All right, guys. Bang, bang. I've got a special treat for you today. I have Jeff Morris here. Thank you so much for doing this, sir.

• 4:05Speaker 02

  Just waking up and this is the best way to start the day. So I'm excited to be here.

• 4:09Anthony Pompliano?

  Most people don't say that to me, so I'll take it. Let's jump into, let's jump into your background. You're investing today, but you spent a good amount of time as an operator. Kind of walk us through where'd you grow up? How'd you get into the technology industry and what'd you do?

• 4:24Speaker 02

  Sure. So I grew up five minutes from Palo Alto and five minutes from San Hill Road. So I was really kind of in the heart of of technology and venture. You know, went to Menlo High School, kind of grew up around around the scene, ended up going to UCLA to study English. Thought I wanted to be something in film. I was screenwriting for a little bit. I worked at UTA, which is an agency. I used to read scripts for 50 bucks in in college for different producers in LA. And I really thought that was my track. And then when I went to the agency world, I just realized how shitty being in being in entertainment is that I literally like, if you'd watch Entourage, I've had like staplers thrown at me like,

• 5:07Speaker 02

  like my life was threatened many times. It just wasn't a healthy environment. And so I left, I was going through a breakup with the girlfriend and just kind of like left LA, you know, in classic kind of road trips. So I packed the car, moved back up to San Francisco and then I was just, this is 2010 and there was so many great companies around. So and I had, I still had good connections, but I wasn't like going to just get a job. I wasn't going to walk through a door and get a job because I knew anybody. And so I just started applying to every, every company I could apply to. And I, it turns out I was really good at applying to unicorns. I applied to Uber to be their 15th employee. I applied to Airbnb to be their 50th employee. And I applied to Twitter to be like their 200th employee and and none of them would hire me. So I ended up

• 5:53Speaker 02

  going to South by Southwest in 2011. I had just, I was sleeping on someone's couch. I had no, no reason to be there, but I met a company called Zarley. And they were based in Kansas City at the time and Seattle, but I ended up just late night on Twitter. I saw the CEO post a job opening and I was the first one to apply. I wrote a really kind of dramatic cover letter and he got on the phone the next day and said he would hire me, but I had to move the next day to Kansas City. And so at that point I was kind of I was kind of being up by trying to apply to all these companies. And so I said, bucket, and I moved to Kansas City. And that was really my entry point into into tech. I had to literally move from LA to San Francisco to the middle of nowhere to get a job.

• 6:36Speaker 02

  And then from there was just kind of became known for building products. Towards the end of Starly, I started releasing a bunch of products online, mostly on product time. And I had three products hit number one within a couple of months. And then suddenly I was like the product person on Twitter and tested out a few ideas. I thought I was going to try and be a CEO. So I tried to start a gas delivery business, which is really a dumb business to start. So don't start it if you're thinking about it. But we were driving, I had a Jeep Wrangler, so we would attach little oil tanks to the back of my car. And we were driving around filling up cars in Menlo Park.

• 7:18Speaker 02

  I also realized people like their gas in the morning and at night, so it's not a great time to be an operator. You have to wake up early and stay late. So I ended up leaving the gas industry. And luckily, at that time, I got a phone call from Tinder and I had used Tinder. I was in online data for several years. At that time, you wouldn't say that out loud because online dating was still kind of a just a weird world and a weird thing to say you did. And so I ended up moving to LA. I was one of their early product members, joined in 2015. The team was about 55 people big, really amazing product market fit, but a very disorganized organization.

• 8:02Speaker 02

  We were just starting to monetize. So we were doing about 20 million dollars in revenue. I think a lot of people misunderstood Tinder and subscription businesses and didn't realize what we'd become. But, you know, kind of like right place, right time, and also just hard work that I ended up. Leading all the revenue products at Tinder, um, kind of from 20 million to 1.4 billion um in in revenue. And it's very much SaaS revenue because it's 97% of our revenue subscriptions.

• 8:34Speaker 02

  And and from there just became kind of like Twitter, Twitter famous, um, which sounds weird to say. You probably understand it, Pop, but um, people were really curious to learn about Tinder and how we were suddenly becoming a a monster business. And so um, I was sharing a lot of those thoughts and and and just became kind of like a person in the in the tech world and and have since gone on to do a lot of things and now kind of focus on investing.

• 9:00Anthony Pompliano?

  Yeah, let's go back to uh, when you put three products to the top of Product Hunt. This is when uh, Product Hunt, like everyone was paying attention and it was the only thing. I think now there's kind of a couple of competitors and maybe some of the attention is a little bit fragmented. But what were the products and kind of why do you think they hit number one?

• 9:18Speaker 02

  Yeah, sure. So um, I mean, I think the the biggest thing was they were really like very quick projects that I built, which enabled them to be a lot more timely. Um, and so one of the products was a good example, Slack was blowing up. Everybody was joining these kind of consumer um, uh, Slack groups. So uh, Slack was really an enterprise tool. They were, they did not want you to discover uh, the fact that they had like AOL chat rooms. Um, and so I released the the kind of the the biggest one that that did really well was called Slack Chats.

• 9:54Speaker 02

  And so they give it as just being a directory of all the best Slack rooms for non-work topics. And it it did really well. It was getting um, a ton of traffic. And then I got a letter from Slack asking me to, uh, cease and desist is what you call it, asking me to take it, to take it down.

• 10:13Speaker 02

  To which I I kind of thought back because I was so happy and you know, to me, I thought I was doing them a service. By giving them more more traffic, but um, eventually took that one down and they sent me the. The funniest part of the story is they sent me a pair of Slack socks after I took it down, which was less than the price of the domain. I was like, all right, great. Now I have to wear your socks on my feet to remind myself of this. This season, this is this letter I got, but that was one of them. And then another one was called Startup Adoption Agency. And so it was just this idea of everybody was launching products on Product Hunt. And a lot of people would have been in the projects and you could adopt other people's startups.

• 10:55Speaker 02

  Which again was like really easy to do, just a little matchmaking product. It wasn't too difficult. And then the other one was called Request for Startups. And so it's taking. Y Combinator every year releases kind of a list of startups they're looking to fund or themes that they're looking to fund. And so we would just go to all the VCs in Silicon Valley and ask them what startups they want to fund and. Created just a kind of a marketplace of ideas where we we try and connect entrepreneurs and. VCs with with projects they actually want to fund. But again, like, these aren't like, there weren't like machine learning teams. They weren't like. Big projects. They were just things I was doing on the weekend. But.

• 11:36Speaker 02

  As you know, if you just release a lot of things, whether it's content or no code projects. And then they do well, people start to to associate you with with being a certain type of person. And for me, it was. Just being someone who can release products at a fast rate.

• 11:53Anthony Pompliano?

  Yeah. What's fascinating to me about this is you basically were practicing, like you were getting reps and you were creating lots and lots of products and you were learning along the way. What works, what doesn't work, you know, how to build, how to iterate. You're getting kind of really tight feedback loops. I'm assuming that you think that a lot of that practice was very helpful when it came to Tinder and some of the stuff you did later.

• 12:18Speaker 02

  Totally, yeah. I was, it was more frustration because keep in mind, I was also trying to launch this gas business on the side, which was just an impossible logistical business to run. And I was like, I can't release this because I have to deal with literally like, like local regulations and governing bodies, but I can release this, this little cheap project on the, on the weekends. And then when I got to Tinder, I didn't have engineers.

• 12:45Speaker 02

  All I had, we ended up giving me access to this platform where you can send push notifications. That was all, literally all I could do for six months was send push notifications. So I started having a lot of fun with that. And I started to kind of run product tests through push notifications. So, and I'll give you a couple of examples. One was, we had this tool where I could draw a map around any, any location. So I would, I would spend my nights like creating little circumference's around, around different venues, being like, if, if Coachella was going on, I would send them what we called a swipe search notification that just said like Tinder's blowing up at Coachella, like open Tinder right now.

• 13:28Speaker 02

  And I would do that for all the large events in, in the country. That, so that was one example that, you know, no engineers. And then we, we ran a similar thing on, in dating, the, the biggest day, kind of like our Black Friday is always the day after New Year's. Because people make their, their resolutions, they're probably hung over, they're sitting on the couch and a lot of them want to meet people. And so we did a swipe search on January 1st. It must have been like 2016 globally, which is pretty scary to do because you're sending 40 million push notifications, which is, you know, if you think about that, just traffic, if you put those people in a football stadium, that'd be like 400 football stadiums.

• 14:10Speaker 02

  But, but that ended up being our, our highest traffic day ever. And then, you know, it got, it got a tech crunch article and then the whole company was like, who's this person on the side like sending these cool push notifications that's, you know, driving our, our highest traffic days. And, and then suddenly like, people started to take me more seriously at Tinder. But I think anytime you Enter a new job or or a product team specifically, you need to like earn the respect of your teammates. And for me, I didn't have engineers, but I had this little tool that I could mess around with. And I think I became like known on the Tinder team as someone who could do good work just because I was

• 14:50Speaker 02

  forcing my way into a kind of into being a person on the team.

• 14:56Anthony Pompliano?

  Yeah, what's fascinating to hear is you're basically talking about various features that maybe people don't think of as part of the product, right? So when people think of product, they think of like the user experience when somebody's in the product or they think of kind of what is this product solve for me? But as a product leader, how do you kind of holistically think both about the user experience you're presenting to somebody? Kind of the backend and what the product can do, but then things like push notifications, you know, all sorts of prediction algorithms. Just how do you think about product and what makes a good product in today's environment?

• 15:32Speaker 02

  Yeah, I think you always have to start with one core product loop that just works like. For Tinder is when we tried to innovate on swiping for five or six years, it was actually really frustrating as a product person because you were trying to like outdo the swipe. But for us, that that core mechanic of just seeing profiles and quickly saying yes or no was so mindless and and core to the product that we had a really great foundation to to build off of.

• 16:01Speaker 02

  So you need you need that like foundation, whatever it is, like that hook or that loop that just keeps people coming back for more. And then, you know, around that, especially for mobile, the the hidden secret amongst product people and most people who are in the industry know this is is push notifications are really your lifeblood. That's your retention tool that keeps people coming back because most people's phones are so crowded with different applications that if you don't have. A good way to pull people back in through push notifications, they just won't think to open your app. And so a lot of messaging, the the kind of highest retention apps are always messaging because you get the most push notifications generally.

• 16:44Speaker 02

  But you know, for for Tinder specifically, we our goal was to get you a match as quickly as possible so we could get you in that messaging loop where you were having a conversation and that became kind of the driver of retention. But I, you know, I really think of it as being, you have to have that core product and then and then it's all about finding ways to keep people coming back. And you know, I think that comes with pros and cons. Because you can have, you can lose trust with the the user if you're if you're spammy or you're not delivering value through those notifications. But for something like Tinder, which is dating, like it, people perceive dating as a very high value activity to their their lives. And if you if you miss a push notification, you're slow to respond to someone, it might be

• 17:30Speaker 02

  that might be your soulmate. And so maybe maybe you just miss like the person you're supposed to spend the next sixty years of your life with, or maybe it's just the person that you want to have a fun weekend with. So you know, it's it's it's a pretty high value activity. So we were we were really lucky to be in dating, which I think is just a fun place to to build in.

• 17:49Anthony Pompliano?

  Yeah. How much of this is like master strokes of genius where you and the rest of the product team sit in a room and you say, oh, we have this amazing idea, like, let's just go implement it and it works versus it's a much more iterative process and you're just testing so many different things and doubling down on the things that work?

• 18:06Speaker 02

  It's a combination of both. I think every team, every product team has to have a few really ambitious projects every year. Where you're you're kind of taking a leap of faith and whether it's through user interviews or data or just like something in your gut tells you this is what you need to build, you need you need those big ambitious projects. And most of those projects actually don't end up working sadly.

• 18:33Speaker 02

  You know, I think it's it's why companies do things like A B testing and you you do try and roll out cheaper versions. So you're not spending. Three or four months of engineering time doing those projects, but you know, around all that is is just a ton of A B A B tests and experimentation. And a big, a big metric of successful product teams is just your, your testing velocity, like how quickly can you release tests? How do you build that muscle internally? How do you get to to significance in your tests, which for Tinder was very easy because we had such a large user base. If you're a startup, it's hard to run a ton of A B tests because you don't have users to run those tests with, but

• 19:17Speaker 02

  you know, it's really a muscle you need to build. And for most startups, you don't actually build that for a couple of years. Like at Tinder, we weren't great at A B testing until probably four or five years into into the company. And I'm sure there's still room to improve.

• 19:31Anthony Pompliano?

  Yeah. What about user research in terms of not a master stroke of genius, not actually like just we're going to throw things out and test, but actually going and talking to the users and getting specific ideas or feedback from them. How did you guys think about that from a product iteration standpoint at Tinder? And then how do you think about it for startups in general?

• 19:49Speaker 02

  Yeah, definitely. I mean, I think, again, like Tinder was such a topical product that you can get your user research in the back of an Uber or at a Sunday brunch. Or people, if you tell people you work at Tinder, they will just start talking for 30 minutes. Like you don't even have a chance to say a word. And they'll tell you all sorts of stories and and they'll give you plenty of product feedback. But we didn't really formalize the user research until again, like probably 2018 or so, in which Tinder was was already four or five years old. And

• 20:28Speaker 02

  you know, I think a lot of the feedback we got at at certain times was done kind of by third parties, which it's hard for someone who works in product and thinks they're they know what they're doing to kind of like trust like third party research and you know, someone does like a big user study and they tell you what to build. So I think the most valuable feedback is

• 20:52Speaker 02

  is one to one feedback that you get yourself. And the job of of a product manager, product team is to really consolidate that feedback and and build the right solutions. But I remember there was a point where towards the end of Tinder, I was actually on, I started a kind of experimentation. Calling it a team is an exaggeration, but I went off and I was like, I want to build an entirely new company within Tinder. And it was the first time, I think, in a couple of years where I literally just, I identified our highest paying subscribers. And I just asked them if they would do a phone call with me and I probably did 20 phone calls and I was like, holy shit, like these people talk to us, so you know, we're a

• 21:36Speaker 02

  a public company and our users will still talk to us, but it was just a good lesson that people are willing to talk to you. And I think the more you can just have one-on-one conversations like we're having right now with with users, as long as you have the right sample set, that to me is the best feedback, way better than anything that a third party could could give you in a 100-page printout of what your users want you to build.

• 22:02Anthony Pompliano?

  Yeah. And what about like gamification in the product? One of the things I think that Tinder really did well was everything from like the super like all the way on down. There were so many features that had monetization kind of woven into them and made it a better experience, but also made revenue for the business. Talk a little bit about just the philosophy behind kind of gamifying some of the Tinder experience that you already knew had product market fit.

• 22:26Speaker 02

  Yeah. So a lot of people referred to Tinder as a game. There was, there were moments internally where we referred to it as a game. I think some people think that's off-putting, but the truth is a lot of people want to use Tinder just to have fun. A lot of people don't even plan to date. They just, they like the game of swiping on people and seeing who likes them. And so we, we definitely leaned into that. I think a lot of the, the products we've built were products that are already been built for dating, which has a ton of people in gaming move over to dating because it's just a really fun place to build, but Super like as an example, or I think Boost is a really fun one. It's you can use a boost to to get more impressions on your profile.

• 23:11Speaker 02

  And it's kind of when you buy it, there's this crazy animation of lightning bolts flying around the screen. And it does feel like, um, if you've ever played NBA Jam and you you kind of your player goes on fire. It's or like Mario Kart, when you when you uh get the, I don't know what the the icon is, but you start racing on the track a lot faster. Um, and we tried to lean into those playful moments and we added crazy video game like animations just to to let the user know like, hey, we know this is kind of um ridiculous that you're buying a boost to to uh to amplify your profile. We don't want this to feel like Google AdWords. Um, let's let's have some fun. And I think the more at Tinder that we just realized that people want to have fun with the product. I think

• 23:56Speaker 02

  a lot of people wanted Tinder to to say it was it was a dating product or to define its use case. And we were just like the the word association is just fun. Um, and we didn't want to be we didn't want to tell users what to use Tinder for. And I think part of that was the gamification and just leaning leaning into the fact that we knew dating is is just kind of a crazy thing. And um, we we didn't want to be a serious product and we never we never. I don't think we ever got there as a product, which is a good thing.

• 24:27Anthony Pompliano?

  Yeah. Before we move on to talk about the investing, uh, talk a little bit just about one or two stories, maybe like, what was the biggest product improvement you made that moved the numbers in a positive way? Uh, and then maybe something you guys tried that you immediately realized that we might be tanking the numbers and probably should shut this experiment off.

• 24:44Speaker 02

  Yeah, totally. So I think um, kind of my defining moment and the big product I built was Tinder Gold, which um, we had Tinder Plus, which was kind of our entry level subscription package and Tinder Gold um, really just moved the business in in a hugely impactful way. And and the core feature in that was being able to see who likes you before you swipe, which actually is a pretty scary thing to build because um, we had these these rules of Tinder. And one of the rules was this kind of like double opt in to to swiping like you don't know who likes you and they don't know who who likes you when when you're both swiping, but um. You know, again, back to video games, like, we have these rules that we come up with as product people.

• 25:28Speaker 02

  And my job on the revenue team was to break the rules a little bit for a subset of users and say, hey, if we, if we let 10% of our users access this feature, that, that kind of breaks the game. Will that, will that, A, is that something that they want to pay for? And then two, will that literally just like, blow up the ecosystem of Tinder? And in the case of Tinder Gold and seeing who likes you before you swipe,

• 25:54Speaker 02

  everything was fine. It not only did increase revenue dramatically, it led to more matches, it created more conversations, it got the, that engagement loop I talked about was, was really sticky. And so, but that was just huge and it was really fun because we were a public company. And so, you know, like, nothing gets a team more excited when you're a public company than seeing your stock price go up. It's just, addicting, especially in like the Robin Hood era where everyone's checking the, the stock price and, you know, we can, we can pretend that doesn't exist, but every day, everybody, when you walk in the office, knows what the stock price is. And everybody gets really excited. So when, when Tinder Gold came out and it kind of like,

• 26:35Speaker 02

  it literally like 2X the enterprise value of Tinder, people were just pumped up, like, like, the mood was always good when we walked in the office. And, and our team was really proud. It was, it was a, again, like, we, your internal, uh, kind of like, like, respect just keeps going up if, if you build products like that. And it was just a really fun product to, to build. I think, you know, some things that, that were hard to do at Tinder. We always want Tinder to be, and, and a lot of people pushed this in this direction. I think we want Tinder to be a social product because,

• 27:12Speaker 02

  you know, obviously, like, like bringing your friends on a Tinder drives growth. It also, I think in the public markets, if you're classified as a social product, it's a, it, it has a higher TAM than, than a dating product. And so, we built this product called Tinder Social, which basically allows you to swipe with friends. And, it just didn't, like, dating at its core is kind of a one-to-one activity. And, we always tried to build like sharing mechanics and, and all these growth, kind of growth hooks, but. In some cases, people view bringing their friends on to Tinder as being competitive. Like, if you go to a bar and you have a bunch of, you bring a bunch of your cool, attractive friends,

• 27:56Speaker 02

  maybe that lowers your odds of finding, finding success or finding your, your soulmate. And so, so social products were just really hard to build on dating and that was something we, we, we saw with Tinder social.

• 28:09Anthony Pompliano?

  All depends on if your friends are attractive or not, I guess, but yes.

• 28:14Anthony Pompliano?

  It makes a lot of sense.

• 28:16Speaker 02

  I lived with, with water polo players when I went to UCLA and they were six foot four and way better looking than me. So I, I had to be like the, the funny intellectual person on the side who would occasionally like meet my soulmate in that way.

• 28:29Anthony Pompliano?

  I love it. Uh, let's talk about investing. Uh, you're investing at a chapter one. Talk a little bit just about your investing philosophy. Why go focus on this full time? And kind of how you think about the companies that you're looking for.

• 28:43Speaker 02

  Yeah, sure. So, um, while I was at Tinder, I was doing a lot of investing and I, I'd, uh, launched a big Angelus Syndicate. I was one of the larger syndicates just by like backers on the platform. Um, I was getting the really cool companies through just being like a person intact. So I'd invested in companies like Lyft, Superhuman, Cameo, um, and the list kind of goes on, but, um, saw myself getting onto, to really great cap tables and, um, you know, Angelus has a product that lets you, uh, launch a, a fund within, within days and they set up all your back office legal compliance. Um, and so I decided just to run an experiment again. I wasn't thinking too deeply about it.

• 29:26Speaker 02

  I just emailed my, my backers on Angelus and said, hey, I'm starting a fund. Who wants to, to invest in me? And I think I had a million dollars of commitments within a day and I was like, holy shit. Now I manage, I'm managing a fund. Uh, and so then I, I made a deck and I got more serious about it and ended up, um, raising uh, about a $10 million fund over the course of, of six months, but, um, was doing this at nights and on the weekends and, and really, there was a, a breaking point where I, I felt like I was doing both.

• 30:01Speaker 02

  Product and investing, I was probably like giving myself, I would give myself like a C plus because I was just so distracted in both directions. And so I needed to make a choice. And for me, at that point, I had so much momentum with, with investing that it just made sense to do it full time. I also got to the point where I, I have a little bit of ADD. I just enjoy working on different problems during the day. And investing is the perfect job if you have any, any ADD. And so, so yeah, and then launching chapter one, I think launching new funds so tough. It's so noisy right now and you need to figure out what your, your hook is again, like it's like a product. You need to, to have something that just like stands out in the marketplace.

• 30:43Speaker 02

  And for me, I knew I loved working on product. I knew I loved collaborating with, with, with founders that way. And I also kept, I kept asking founders in, in kind of those early investments, like why do you? This was after we, we work, we started working. I was like, why did you like let me invest? And they kept saying like, I wanted, I wanted your help on product. And so I was like, okay, like I've heard that again, like user research, I've heard that enough times where I think that's why people want to work with me. And so I branded the entire fund around being like the product person on your cap table.

• 31:15Speaker 02

  And so I tell founders like, I want to be your first phone call if you have any, any product questions, whether it's you're having like some issue with your A B testing platform, or you're having like this big existential question around what you want to build. And you just need like a third party to come in and play tiebreaker a little bit. And, and, and then I thought to myself, where do people really need help with product? It's before they have product market fit. And so it made sense to be an earlier stage investor. And so we do pre-seed and seed investments and typically kind of look for teams that have a really unique lens on, on, on product. And normally it comes from being like a former VP of product or director of product somewhere,

• 31:58Speaker 02

  or just a great engineer who has product sensibilities. So I end up working with like a lot of really like nerdy semi artistic product people who just like love to, to talk about this stuff all day long.

• 32:14Anthony Pompliano?

  Talk a little bit about your thoughts. Like you focus so much on product. I've had people come on the podcast who say, maybe that product doesn't matter, but like distribution is everything. And you know, the truth is probably somewhere in between. Like you need a good product and you need good distribution. How do you kind of think of that at the earliest stages, especially you know, pre-seed and into the seed round for companies, especially the ones that you're working with that are very product focused?

• 32:38Speaker 02

  Yeah, I I've talked with so many people at this topic and I, you know, like the the prideful product person to me says like, product is everything. It's all that matters. But as you mentioned, I think distribution, especially right now, is is probably more important. And and that might go against what kind of the fund thesis is, but the truth is, you know, within your product, like growth and go to market are part of the product strategy. And so it's not, they're not two different competing areas. You know, if you're building a consumer mobile product, you will get the question of how like, how are you going to get people to download your product? There's millions and millions of apps on the App Store and people

• 33:20Speaker 02

  just don't like downloading new apps. So that's, that's a big question on the, on the B to B side. I think there's, there's different unlocks, whether it's, hey, you know, we, we have, you know, we just got through Y C and we have access to 3000 Y C companies. That's a growth, kind of a growth unlock. There's, but I'm always looking for different unfair advantages, or especially right now, like I just did a consumer deal and we're just stacking the cap table with TikTok influencers, which sounds funny. And I tweeted about this yesterday, but I was like, which TikTok influencers are actually investing right now? And so we made the choice to not have

• 34:04Speaker 02

  too many Silicon Valley investors. We, we want people who have audiences. And so.

• 34:10Speaker 02

  Again, and that's all distribution. We know we have a product that works, but we need eyeballs on that product. And so we're trying to figure out how to get those eyeballs.

• 34:19Anthony Pompliano?

  Yeah, it's really interesting. As you think through kind of building in the earliest stages, is it something that precedes a seed company, again, masterstroke of genius? Just because they don't have enough traffic to really kind of run an iterative process and kind of get feedback? Or do you think that many of these product folks can still kind of run that iterative process? And maybe they don't have tons of traffic, but they can do some things to kind of short circuit learnings and really get the product in a place where it's valuable and finds product market fit?

• 34:51Speaker 02

  Yeah. I mean, most in consumer, especially you need a little bit of genius. You just do like you need a core nugget or idea that just blows people's minds and gets people to talk about your app enough, where it becomes like a Sunday brunch conversation. I just believe in consumer that you need that.

• 35:15Speaker 02

  That said, there's ways you can run tests if you don't have traffic. And we see a lot of people do this at different accelerators or studios more when they're incubating ideas, is you can take out fifteen or twenty thousand dollars and run a bunch of smoke tests against different landing pages and product ideas to see what converts and see what people will literally just sign up for.

• 35:41Speaker 02

  Sometimes you can A B test products with medium posts, like all sometimes they'll have an idea and I'll say, hey, I'm building this. I'd launch a medium post and if nobody responds, then maybe nobody thinks that's a good idea. And if they do, then the only problem is then you have to actually build the product. You say you're going to build them, people want it, but you can, you can, you can find ways to get traffic. I think you're just trying to see if people will literally. Sign up for it. And if you have something, you know, hopefully, hopefully you can have enough traffic to measure retention over a period of 28 days or so. But yeah, I do think it's harder to be tested sort of it. Don't be creative and figure out ways to get that traffic because you

• 36:26Speaker 02

  can you can do it if you have a little budget.

• 36:28Anthony Pompliano?

  Yeah, you're investing as a solo capitalist. Talk through kind of the thought process of why invest as a solo capitalist? What are the advantages? Maybe what some of the disadvantages are as you've been doing it for a while now?

• 36:41Speaker 02

  Yeah, I we were talking about this before the show, but I've always invested on my on my own. And I've just developed a lot of confidence in my picking ability. And so I went through the process this year of like, asking myself, do do I need to bring on other investors, other GPs? And just in the past year, LPs, limited partners have become so accepting of solo capitalists, where to me, it's an advantage right now, because you it's so competitive. And if you can move with with a slightly faster speed by being solo, you can win deals. And I let a seed deal this

• 37:25Speaker 02

  week where I was literally, I got to them first, and I said, yes, before they could talk to other investors. And if I had a team, I would need to pull in someone else, and it would be this whole process. I think the key is is is building a support system around you, either through platforms like Angelus, or by setting up your own back office, where you don't have to worry about the other parts of your job. And so you can just focus entirely on investing. I also think a lot of people, as you have a big kind of online presence, if you have a big online presence, and you can raise money, bring on a partner, in most cases, just doesn't really make sense if you can if you can, you know, raise a funding and get going up, unless you find the perfect

• 38:10Speaker 02

  complement to you. And I've gone through the process of talking to a few folks about partnering. And it just hasn't, you know, back to like dating and like I haven't found my perfect match, but maybe, maybe one day somebody will come into my life and I'm, I just need to work with them. But until that happens, I'm so happy doing what I'm doing now.

• 38:29Anthony Pompliano?

  Yeah. How do you think about the balance between like, speed of decision making and quality of decision making? This is something I constantly go back and forth on, right? Cause when you're a solo capitalist, you definitely have speed, but you don't have those investment committee meetings. You don't have partners that you can kind of bounce ideas off of. How do you, you know, are there things that you maybe you do to get feedback or have sounding boards? And then also, how do you just think about the trade off between speed and quality of decisions?

• 38:57Speaker 02

  Yeah, sure. So I think there's two parts to this. One is just this idea of a prepared mind. And so it's doing the work before you have that meeting, or knowing what you're looking for and having seen enough kind of like, like different versions of my, of an idea. You've gone through the idea maze. And when you see it, you just know, like you, you're like, I've seen 10 of these companies and, and there's this slightly different twist where this is actually the, the company at the back. So having a prepared mind is a big part of it. The second part is building, kind of building your, your support system in terms of, of peers and people you invest with. So I invest really often with, with

• 39:41Speaker 02

  the same people. I know we're on cap tables together, but I invest with guys like Ryan Hoover, great investors like Lee Jin, Harry Stebbins, Tadim Ruhul from Superhuman. So we're always doing deals together. Josh Buckley is another one. And, and, and so I'll, I'll send deals to those people. Maybe I'll kind of like be around the hoop and, and thinking about committing. And I just get their reaction. So it's like having an investment committee, but we all have different balance sheets and different funds. And so you get, you get that peer feedback. But I think, I think being a, being an investor can be a really lonely job as, as you probably know. And so you need to figure out who your peers are

• 40:25Speaker 02

  going to be in. A lot of people build peer groups within investing. They try and go really wide, like they have. A hundred people who they catch up with every, every couple of months and it's, it's not very, it's not a very intimate relationship, but I've, I've kind of just like picked, and it's happened naturally, like 10 people who we just love to bullshit all day long about investing in.

• 40:51Speaker 02

  And we challenge each other and it's, it's probably what it feels like to have an investment committee.

• 40:55Anthony Pompliano?

  Yeah. How do you think about follow-on investments in terms of you're investing at the pre-seed and seed? Do you try to save a bunch of capital and kind of invest it to stack? Do you just say, hey, look, I'm going to make a good decision pre-seed and seed, and then I'll just take the dilution later on? What's the strategy or thought process?

• 41:13Speaker 02

  Yeah, for me, I, I have reserves baked into my, my fund. A lot of people view these smaller funds as being first check funds. And then you kind of spin up SPVs for your winners.

• 41:27Speaker 02

  I talked to a lot of people who are smarter than me, Mike Maples from Pluggate, Chris Dixon from Andrew and Horwitz, and they all insisted, and they, they showed me data that, that suggested having reserves would increase my, my performance. As long as I could pick the right companies to double down on, which is an entirely different ability. So I have 50% reserves. I'll occasionally do, I'll, I'll see a great series A occasionally. I didn't invest in the seed and if I do those, I call my, my reserves like flexible reserves. So I'll take money out of my reserve bucket and do the deal, even though I didn't invest in the pre-seed or seed.

• 42:07Speaker 02

  But out of my fund, I think we've invested in 45 companies. I'm looking to, to deploy reserves into like eight, my top eight companies. And I don't know, the, the hard part about investing is I know I'm a pretty good first check picker, but TBD on if I'm the right, if I'm good at reserves and reserves management. And so I'll, I'll be curious to see how that plays out.

• 42:29Anthony Pompliano?

  Are, are there anything other than just pure returns that you're looking at to see how you'll measure whether you're a good kind of reserve picker or not?

• 42:37Speaker 02

  Uh, for me, again, I worked on revenue teams like I'm very dollar driven. And so there's no, there's no kind of like, like I'm going for, for, for, for returns and, and there's, I don't get kudos for anything else. So I want to, to five X my fund or, you know, there's some scenario where my fund does really well and becomes kind of a legendary fund. And I want to be those stories where people say, you know, Chris Saka's first fund was like this because he had Uber. Like, everybody wants to have that legendary fund. So that's all I care about. And, and that's how you stay in the business.

• 43:19Speaker 02

  If you can't return capital to investors, I'll be out of this game. I'll be back on product teams after fun too. So, um, so I'm really, you know, I'm really kind of returns driven. It's hard because you meet great entrepreneurs and maybe your check size isn't big enough that they give you, or maybe you love them, but you just don't see the, the kind of market potential, what they're doing. And you have to say no all day long, um, which is the hardest part about this job. And so, yeah, that's, that's kind of how I think about the world.

• 43:47Anthony Pompliano?

  Makes sense. Uh, what are the, some of the downsides to the solo capitalist model? We talked a little bit, maybe it just got kind of being out on an island. Is there anything else that you've noticed as a downside?

• 43:57Speaker 02

  Yeah, I think, um, I think sometimes you can be viewed in the market or as entrepreneurs is as being kind of like an angel sized check. So if you, if you start raising a larger fund, maybe you raise, you know, a $40 million fund or even I've seen solo capitalists raise a hundred million dollar funds. And you're asking for a $1 million check. Um, and then they have this other fund that has a platform and they have a, like a platform team. And they have, you know, 10 partners and it's just, it's like, you can imagine how that model, um, to some entrepreneurs, it appears to be a better place to go. And It's just different people view, view solo couples as being, your other viewed as a fund

• 44:40Speaker 02

  or you're viewed as an angel. And so those are hard conversations because I think the, right now, again, like, if there's a great company, there's going to be dozens of investors trying to get on the captive one. Why are you the person who deserves a, you know, a 500K check or a 250K check, which, once you start going above 250K, it starts to become hard at the precedency. You have to convince them that you're either the second or third largest check. And so, and then maybe you make some, some compromises on quality at that point. And so it's this, it's this kind of, kind of mouse game of knowing how big your fund should be based on how much power you think you have in the market and how you're viewed as entrepreneurs, or viewed by entrepreneurs.

• 45:26Anthony Pompliano?

  How has your process changed with the pandemic and kind of the lockdowns? Were you already doing most, everything remote and it's not a big change? Were you taking a lot of in-person meetings and you had to kind of adjust?

• 45:38Speaker 02

  Yeah, it's been all, all Zoom. I've, I've invested in, I think 40 plus companies this year. And I've met one of the entrepreneurs in person and it was after I'd invested in them. And so, and that's shocking to some people. Like I, I was pitching a really well-known institutional LP and they asked me the same question. I said, I haven't met any of these founders in person. And I, I could kind of tell like, based on their reaction, I was like, that wasn't the right answer. But this is the new world we live in. And especially at the precedency, it's so fast. People are building products all around the world now. And so, and we're in a pandemic. So there's really no other option. You have to figure

• 46:23Speaker 02

  out how.

• 46:26Speaker 02

  To evaluate people on video and a lot of it's social cues, a lot of it's reference checks, but I've just become so comfortable interacting on video and to me, I don't need to like shake someone's hand and have coffee with them anymore. Of course, I'd love to. I love, I love meeting people in person, but if you do that, you'll probably miss the deal.

• 46:49Anthony Pompliano?

  Yeah, I tend to agree. You recently posted on Twitter, a photo. It was very beautifully taken. I don't know who took it, but it was you with the Golden Gate Bridge behind you and the waves of San Francisco. And you, I'm gonna paraphrase, but basically said, look, there's a lot of debate right now on, you know, every other city in the world, but like, San Francisco is still beautiful. I took that to be, you will still spend a lot of time in San Francisco. What's your general kind of take on Austin, Miami, LA, San Francisco, New York, and, you know, wherever else internationally people are considering?

• 47:27Speaker 02

  Yes, I posted that photo yesterday and my wife sent me and I looked at it. I was like, you know, we had a lot of good times in San Francisco. I started my career there. I was born in the Bay Area. I met my wife in San Francisco. And so the Twitter narrative is so bearish on San Francisco and it's, you know, it's gotten really aggressively anti San Francisco. And at times I've been a part of that in different ways. Not aggressively, but I've been, you know, very open about the fact that I think San Francisco needs to change in different ways. I got a text actually from my mom two weeks ago. Kind of, it was like a mom to son moment, which you still have when you're, when you're adult, when you're an adult. And she said, like, why, you know, it's kind of like, why are

• 48:11Speaker 02

  you speaking so negatively about San Francisco? Which I didn't think it was that negative, but she was like, this is the place where you grew up and it afforded you so many great opportunities. And it was just a good reminder that the city itself and the barriers given me so much. And I was just trying to like, Create some positivity around San Francisco because a lot of my friends still live there. A lot of my family lives there and to wake up and see people cheating on your city all day long probably doesn't feel good. And candidly, we might move back to San Francisco at some point. Because again, I grew up there and I still think there's so much value in being in the center of it all.

• 48:52Speaker 02

  I have a couple of brothers, I have a brother, one of them just moved to Austin in August. Another one's moving to Miami in March. And so I'm like the brother who's trying to figure out where I belong. And for the moment, I'm in LA, but I think as you've seen, you can build a company anywhere. I think the question is just can you raise capital in these places? And I more and more think that investors don't care where you are, as long as you're building a great company. And so it's very, the one great thing about the pandemic is I think people have finally just,

• 49:28Speaker 02

  they're like chasing their innate desires. You're, it's kind of like this fantasy world where it's like, where would you live if you could actually live anywhere? Again, this is for people who are lucky enough to be able to do that. But and you're seeing people live in Hawaii, you're seeing people live all over the place. And you know, it's a very privileged thing to be able to do, but but I'm seeing people who are, you know, they're happier because they're not bound to one city and it's the quality of life for them has increased in many ways.

• 49:59Speaker 02

  So it'll be interesting to see how things shake out. I still think there will be some pullback on the San Francisco narrative. People will come back to San Francisco. I just don't know if it's going to be quite the center of gravity that it used to be. And so I think there will be, especially if the city doesn't change in terms of, you know, I'm sure you've seen the debates about Chesa and the district attorney and all the crime. It's not a safe place to live right now. And so until it becomes a safe place, I don't think it will ever return to being the San Francisco we know and love.

• 50:35Anthony Pompliano?

  Absolutely. Before we move on to anything else, where can people find you or send you deals if they're working on a company that they think could be a good fit?

• 50:44Speaker 02

  Yeah, definitely. So I'm JMJ on Twitter, which is a great place to find me. And then, you know, my DMs are open. All the Twitter's DM product sucks, but my DMs are open. And then, you know, there's a chapter1.com is my website. So you can visit chapter1.com.

• 51:01Anthony Pompliano?

  Got it. The Twitter DM search works like 20% of the time, 80% of the time it doesn't, but at least they have it now. So like, I guess that's like somewhat of an improvement.

• 51:11Speaker 02

  I know. If you want to go viral on Twitter, just complain about Twitter DMs because everybody will like your post and reshare it. It's like, it's like the one thing we can all agree on is just not a functional product.

• 51:25Anthony Pompliano?

  Before we get into the rapid fire questions that I always ask everybody, I pulled some questions from Twitter and we'll kind of go through these. Drew Morris, who I'm assuming has zero relationship to you, wants to know, who is your favorite brother?

• 51:41Speaker 02

  Oh, man. He's my Miami, my Miami brother. But I grew up in a house with eight kids. My parents split, but they remarried. And so there's kids everywhere. And Drew, Drew's a lawyer. He likes to ask really pointed questions. So honestly, I, this is going to be like the most PC answer, but I love each brother for different things. Like Drew and I have completely different conversations. We talk about all sorts of stuff. And then my brother in Austin loves investing, Matt. And so I'll call him and we'll just like, talk about the craziest investing ideas. I know, Pomp, you have brothers, but I have such different relationships with all my siblings. And yeah, I can't, I can't pick one for you. You know that.

• 52:26Anthony Pompliano?

  He knows, but he's gonna ask anyways. Liz Keating asked for you to explain your college bedroom slash sunroom and explain the impact that it had on your life.

• 52:40Speaker 02

  Yeah, sure. So I lived, as I mentioned, with a bunch of water polo players. And then Liz, Liz was a swimmer at UCLA and is a great friend of mine. She was also in the house, but we moved in together and there was a sunroom in the back and everybody was picking their bedrooms. And I ran in, I was like, this is my room. I get the sunroom, which I don't think anybody wanted, but I was trying to be, at that time, I thought I was going to become an author. And so I was like, this is very like poetic place where I had a typewriter in there and I was just like, totally just like in this like fantasy world. I didn't, I was, I was an English major. And so the sunroom just became like a part of my personality. It's like Jeff, Jeff's the one in the sunroom is kind of just like a weird first choice.

• 53:23Speaker 02

  But at the time, I was always just trying to do like, the most hipster emo thing I could do. And it's felt like living in the sunroom was like, a place to be an author.

• 53:33Anthony Pompliano?

  That's, that's a great answer. It makes a lot of sense.

• 53:37Anthony Pompliano?

  Dallas Cohen asked, if you could have lunch with anyone who is living, who would you choose?

• 53:44Speaker 02

  Yeah, definitely. So my grandpa's 100 years old. His name's Murph Morris. He started Mervyn's Department Stores, which ended up becoming a, a large public company. And I love talking to my grandpa. It's just like, we can talk about business. I can talk to him about how he was, you know, started his first story, didn't have any money. He took out a bunch of, of debt and how he grew that to becoming just a public company. It's so fun. And then just on a personal level, it's pretty amazing to have a grandparent that's seen that much. Who's, you know, been through multiple wars. He's, he was born on the 4th

• 54:24Speaker 02

  of July. So he's very, he's, he's, he's very patriotic. He's, and he's just somebody who I'd love to spend time with. And so he, he definitely wins that, that question.

• 54:36Anthony Pompliano?

  That's a fantastic answer. Jonathan Badine, I think is how you pronounce it.

• 54:42Anthony Pompliano?

  Yeah, he wants to know what your morning routine is, which tells me he knows something I don't know. So what, what, uh, what's he asking for?

• 54:48Speaker 02

  So Badin is the inventor of the right swipe, which is his, his great claim to fame. Well deserved. But so when I joined Tinder, I was asked to, there's this website called mymorningroutine.com and they asked me to write an article. And if you read the newsletters, it's people who have these really like prescriptive morning routines. And so I thought I had, at the time I was pretty regimented in my mornings, but I wrote this ridiculous summary of what I do in the mornings or what I did. And it was like, you know, six o'clock, I wake up for yoga, like seven o'clock, I walk home, I, I like, you know, listen to my record player for 10 minutes

• 55:29Speaker 02

  or it was just, it was ridiculous. And looking back on it, I'm, I laugh at myself, but it was trying to like summarize my morning routine. And the truth is now my morning routine is completely bonkers. Like during, during quarantine, I'm just like, you can get an extra hour of sleep if you need it. So I've just decided that I'm not going to pretend to be like the Tim Ferriss of morning routines. And I'm, I wake up when, when, when I'm ready and I, I work a long day, but I'm not going to try and be like the most productive human in the world. And I don't, I don't think that's my personality at this point in, in, in life.

• 56:05Anthony Pompliano?

  I love that. And I love that he knows that you've got a great answer to this. That's why he's asking. The last one comes from a pseudonymous account, Stock Market Hats.

• 56:16Anthony Pompliano?

  But it was a, but it was a good question. What is your best and worst investment that you've made?

• 56:22Speaker 02

  Yeah, honestly, a lot of my best investments, and I know you're deep in crypto than crypto bets. So, Compound Finance was, was a really great one. Of course Bitcoin's been a great one for so many of our, of your listeners. But I love, I love the, the, the quick returns on, on crypto and how you get liquidity really quickly. It's, it's a really attractive thing. I think a lot of my best investments will still play out on the private side because I really started investing five years ago. And so I invested in a company called Rome Research in March that I'm really excited about.

• 56:59Speaker 02

  And so we'll, we'll see what happens. But in terms of bad bets, I think I've made a ton of them. And it's mostly things that you didn't invest in. But rather than calling out one company, I think it's, it's, it's been when I just invest in things outside of my strike zone. I've talked with, with Mike Maples a lot about this. It's just like, as an investor, you have to know what you're good at. I think it's, this is true for a lot of parts of life, but self-awareness is a big part of investing. And whenever I've made mistakes, it's just things that I don't know enough about. And so part of becoming a good investor is refining your idea of what your strike zone is and then sticking to it.

• 57:42Anthony Pompliano?

  Yeah, I couldn't agree more with that. I asked the same three questions to everyone before we wrap up and you'll get to ask me one to finish. The first question is a little bit more serious. What's the most important book that you've ever read?

• 57:55Speaker 02

  Yeah, for me, it's, it's always Catching the Rise is my favorite book. I love Holden Cottrell. This is outsider. He has his own mind. It's also a book where in high school I read it and I was, I wanted to write like that. I was like, I want this like stream of consciousness, first person narrative. And I started to write a lot after that book and I became, one of my teachers in high school pulled me aside and he's like, I think you could be a professional writer. And so, and I tried to be a professional writer. I, I spent two years trying to be a screenwriter. And so, so that, that book really like led me down this path of trying to communicate better through, through writing.

• 58:37Anthony Pompliano?

  Yeah, it's awesome that you get inspiration from the things you consume, right? So yeah, that's fantastic. Next question is from our friends over at Eight Sleep. They got me asking everyone, what is your sleep routine? And the context here is I did not sleep at all. Like I literally would operate on like four or five hours. I was flying all over the place and just beating on my body. And in 2020, I told myself, I'm not going to fly anywhere. Like I'm going to chill. And then the world conspired to make sure that that came true because literally I was locked in my apartment. And, and I eventually got a, an eight sleep mattress and it's like thermo regulation. Now I sleep like a baby. So are you somebody who sleeps a lot? Who didn't sleep at all? How's that evolved over time?

• 59:21Speaker 02

  Yeah, so I actually developed sleep apnea in high school. When I was 15, I was I could not fall asleep for the life of me. And I started taking Tomo PM. Eventually, I started taking Ambien. Like, it was, it was, it was not good. And then I started to work out a lot more and just that helped a lot. So I was working out. I'd fall asleep better. And then, you know, all the way up to now, I do have an aid sleep mattress. So Mateo will be happy that I got the aid, the foam pad or the pad that goes on top of your mattress. And that's been just so cool. So my wife has her side of the bed, which she can regulate the temperature. And then I have my side. And then there's no,

• 1:00:06Speaker 02

  I sound like an advertisement, there's no alarm clock. Because you, it vibrates your side of the bed. And so my wife doesn't have to wake up and be mad at me when, when the alarm goes off in the morning. But that's, that's helped a ton. And then, you know, I tried, again, like, I try to not look at devices before bed. And I'm not, I'm not a saint. Like, I do, I do check my email before bed and I'm, I'm addicted to work. So, but similar to you, I've sort of valued my sleep a lot more. And I used to sleep four or five hours a week. I was like cranking, you know, trying to stay up till 2 AM. And I've just gone to the point where

• 1:00:46Speaker 02

  I've thought, thought more and more of like entrepreneurs and, and just investors as being more like athletes. Like, you have to take care of your mind and your body to make good decisions. And so I try and get seven or eight hours of sleep. I still have like really shitty sleep nights. But, but I think, I think socially, the value of sleep has just become such a topic. And it's something I'm paying attention to.

• 1:01:11Anthony Pompliano?

  Yeah, I told Mateo that this was gonna happen. I said, if I start asking people this, like, half the guests are gonna be your customers. So it's gonna just be, I was tired by eight sleep. The last question I have is more fun. And then you get to ask me one, aliens, are you a believer or a non-believer?

• 1:01:28Speaker 02

  I'm a believer. I, I, when it comes to space, I trust Israel. And if they say there's aliens, I'll, I'll just go ahead and say that there's aliens.

• 1:01:38Anthony Pompliano?

  So you're a, what do they say, Galactic Federation was the guy who said, we're all part of a Galactic Federation? And, and they just don't want to tell us yet?

• 1:01:47Speaker 02

  I did think so. There was one part of like someone was trying to make Trump unlock all the all the documentation about aliens before he left left the White House. And of course, today, we have a new president and we didn't see those documents. So I'm curious if Biden will unlock the documents.

• 1:02:06Anthony Pompliano?

  Yeah, my favorite moment over the last four years was I remember when everyone was going to storm area 51 and like six people showed up or something like there's this whole thing. We're just going to go find it. And if you're like, I don't think that's where they're keeping the information. Like, I'm pretty sure the information is somewhere else.

• 1:02:22Speaker 02

  Yeah, I think Elon Musk should just own this topic and like, he should be the one that tells the world if there are aliens or not. I think he it would just be like the most viral topic with the most viral person. It would just light the world on fire.

• 1:02:36Anthony Pompliano?

  That's a great suggestion. Don't let him hear that because he will he will definitely try to try to do it. All right, you could ask me one question to finish up. What do you got for me?

• 1:02:44Speaker 02

  Yeah, pump. I'm curious. Obviously, we met, I think, in 2014 or 2015. And you were exploring crypto and you just made this decision to just go all in, which for me, I think is there's a deeper part of that, which is really applicable to many people, which is just like owning something and not giving a shit. If people judge you, I'm sure there were people in your life who told you you were insane. I'm sure there were other investors who told you you were an idiot. And I'm sure there are a lot of people in Silicon Valley who who wrote you off. But what like freed you to just jump in and

• 1:03:26Speaker 02

  how did you not give a shit, I guess, is the question?

• 1:03:31Anthony Pompliano?

  Yeah. So I don't think it necessarily was around like investing as much, you know, like, hey, caring what other people thought or not. I had this really unique experience when I was 20, 21 years old, where I was in the military, went to Iraq. And I was there with a bunch of guys that were a little bit older than me. So kind of late 20s, early 30s, I was frankly, just a dumb naive, like very Impressionable kid. And when I got there, I had basically had pulled out of college to go. And so I'd been worried about like, what was like the party on Friday night, right? I mean, the same things that everyone's worried about, you know, like, do I have enough money to get some beer and have a good time?

• 1:04:15Anthony Pompliano?

  And so these guys were worried about like their wives and their kids and their mortgage and is their job gonna take them back when they come home? And like, real life kind of adult things. And so that was like one like this like maturation process that like I had to really accelerate because of it kind of just being around them in the conversation. But the second thing was like, it's war. And so you see both the good and bad sides of that situation. And I think that at that age, like in that moment, what really stuck to me is just like, oh, we're all gonna die. Like, there's an end to this thing. And so when I came back, there was like a short period of time where I probably like, I implemented that learning in like a negative way.

• 1:04:58Anthony Pompliano?

  Like, I had a motorcycle, I'd go like 120 miles an hour down the highway and just like, well, if it happens when I'm 21 or if it happens when I'm 81, like, you know, it's like very quickly, like you kind of get that out of your system. But I think that it really just got me to the point where I really just didn't care, right? It was like, hey, look, like you only have so much time and like, who cares what anybody else thinks? And so like, that's a hard lesson to learn because you have to go through that specific experience to get that. But I really carried that with me for, you know, ever since, really. And so when it came to investing, I think the one thing that I just kept telling myself was like, the thing that seems least likely, but has the most asymmetry is like the area to go focus on.

• 1:05:44Anthony Pompliano?

  And to me, like when I first started looking at it, I was like, this is insane. Like, literally, like, you people are crazy. There is no way that this is gonna work. And I remember I sat down with a couple of people and they were like, but if it does? And I was like, Good point. Yeah, like if it does, like this is, you know, one of the largest probably like disruptions and not, you know, just a Bitcoin thing, but like from an ethos standpoint, from a decentralization, a privacy centered technologies, like all this stuff. And so I just slowly started to do it. So it was never like I sat down and was like, you know, all right, I'm gonna just go focus on this. It was kind of a slow evolution. And then what I started to realize was as I got better educated about, I started meeting more people. It was like, oh, like this is real, right? And I felt like I kind of knew something before other people.

• 1:06:30Anthony Pompliano?

  And other people would warm up and kind of learn it as they spent more and more time as well. So that was like one advantage. And then the second thing was, uh, I was willing to be wrong. And I think that's where it was one thing to like have the opinion like, hey, this is gonna be big and let me like go invest capital. But a lot of investors, like they'll invest a lot of crazy stuff, but they don't talk about it. Right? Or they don't wanna like go bang the drum publicly and like, you know, talk about a lot of their early stage companies until they know it's gonna work. And then it's like, oh yeah, I was early. Right? And so for me, it was just like, if this works, this is going to be really, really disruptive. And I'm willing to like, one, be wrong in public, but also two, I'm willing to learn in public. And so like, I'm gonna change my mind. I'm gonna like do all this.

• 1:07:13Anthony Pompliano?

  And I think it was just the expectation setting of like, I may be wrong, but I'm gonna like go through this entire journey in public. That gave me the like safety net of if it doesn't work, then I'm like, well, we all learned together. It didn't work. So it almost felt lower risk than I think a lot of people thought it was. But, you know, looking back like, yeah, it's pretty crazy, uh, I guess. And so, you know, it's working, I guess, and that's a good thing. But I still worry that, you know, the more and more that, uh, your public reputation becomes tied to something or is like very much intersected. That's great today when it's working, but like, God forbid, something negative happens in the future, like there's still risk to some degree.

• 1:07:56Anthony Pompliano?

  And so you just, I think, gotta be smart about, um, you know, educating people about, hey, here's the risk, do your own research. Like, that's why I talk about that stuff a lot. It's just to clear my conscience of like, hey, you know, I'm doing the work. I'm making my own decisions. You should do the same thing. And if you do that and you decide this is what you wanna do, then, uh, you know, all for it. But, uh, to just make sure you kind of do your own work.

• 1:08:17Speaker 02

  I love that. I love the part about you found something like there's a hidden secret that you found before other people and in investing, I think that's so, that's what you're looking for. You're looking for hidden secrets that whether it's emerging communities or behaviors and you just know before everyone else and you're, you know, for you personally, you, you did put yourself out there as an observer, like, and it was, it was very, I think it's very risky to do that in ways because at that time, maybe, maybe you eliminate yourself from getting a GP job at a big venture firm, but you were okay with, with just going in a different direction with your life. And, um, you know, as an observer, it's, it's, it's been really fascinating to see.

• 1:09:01Anthony Pompliano?

  A- a- as you know, uh, when I really started to learn about it, I thought I missed it, right? I was like, oh my God, like, how did I not see this? Uh, so that was like one weird thing. And then two, uh, I won't say who it is, um, cause I'm still, you know, pretty friendly with them and they've been incredibly gracious with their time. But like, there's two or three people that I always keep in the back of my head. Like I got the messages of like, you're torpedoing your career. Like what are you doing? Um, and for whatever reason, it's just like, I just followed my gut. And like, that's a horrible, uh, kind of theoretical decision-making framework of like, I just followed my gut. But over time, I think people just become more comfortable, especially as you get more mature and kind of more experienced, you, you just become more comfortable doing that

• 1:09:44Anthony Pompliano?

  and can't explain it. Um, but you know, we're that so far, so we'll see.

• 1:09:49Speaker 02

  I love it. Yeah. My best decisions are always when I follow my gut in investing and in life, but, but investing. And then my worst decisions are when you have that feeling and you still say yes. Um, and so that's so powerful. And, and again, like knowing, knowing when to follow your gut is, is something I've learned. It took me 36 years to learn how to do that. And I think I'm still learning it.

• 1:10:13Anthony Pompliano?

  I have a friend, I'll leave you with this one thing. He used to always say, "We're doing irrational things. Why are you trying to be rational?" Like, kind of just, you know, stop trying to explain it, stop trying to defend it. It's just like, if you believe in it, do it. So, all right, Jeff, listen, where can we send people? @JMJ on Twitter?

• 1:10:36Speaker 02

  @JMJ on Twitter. You can follow me. I tweet a bunch of crazy things. Don't take anything I say too seriously, but @JMJ on Twitter.

• 1:10:45Anthony Pompliano?

  And chapter1.com.

• 1:10:47Speaker 02

  Exactly.

• 1:10:49Anthony Pompliano?

  Awesome, man. All right, well, listen, thank you so much for doing this. We'll definitely have to do it again in the future.

• 1:10:52Speaker 02

  Thanks, Bob. Appreciate it.