The Pomp Podcast - #479 Jeff Morris Jr on Investing In Product Companies

Episode Date: January 27, 2021

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 =======================

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Starting point is 00:00:00 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 discussed 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.
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Starting point is 00:02:57 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. 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
Starting point is 00:03:41 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. 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. Just waking up, and this is the best way to start the day, so I'm excited to be here. Most people don't say that to me, so I'll take it. Let's jump into your background. You're investing today, but you spent a good amount of time as an operator.
Starting point is 00:04:20 Kind of walk us through where did you grow up, how did you get into the technology industry, and what did you do? Sure. So I grew up five minutes from Palo Alto and five minutes from Sand Hill Road, So I was really kind of in the heart of, of technology and venture, um, you know, went to Menlo high school, kind of grew up around, around the scene, ended up, uh, going to UCLA to study English, thought I wanted to be, uh, uh, some, something in film. I was screenwriting for a little bit. Uh, I worked at UTA, which is an agency.
Starting point is 00:04:49 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, how shitty, uh, being in, being in entertainment is that I literally like, if you'd watch entourage, I've had like state staplers thrown at me, like, like my life was threatened many times. Uh, it just wasn't a healthy environment. And so I left, uh, I was going through a breakup with the girlfriend and just kind of like left LA and classic kind of road trip style, pack the car, uh, moved back up to San Francisco.
Starting point is 00:05:21 and then I was just, this was 2010 and there was so many great companies around. So, um, 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. Um, 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. Um, and I applied to Twitter to be like their 200th employee and none of them would hire me. So I ended up, um, going to South by Southwest in 2011. I had just, uh, I was sleeping on someone's couch. I had no, no reason to be there, but I met a company called Zarly and they were based in
Starting point is 00:06:03 Kansas city at the time and Seattle. But, um, I ended up just late night on Twitter. I saw the CEO posts a job opening and, uh, I was the first one to apply. I wrote a really kind of dramatic, uh, cover letter and he got on the phone with me 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, uh, I was kind of being an up by, by trying to apply to all these companies. And so I, I said, fuck it. And I moved to Kansas city. And, um, 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. And then, um, from there was just, uh, kind of became known for building products, uh, towards the end of this early, I, I started
Starting point is 00:06:44 releasing a bunch of products online on mostly on product hunt. And I had three products hit number one within a couple of months. And then suddenly, um, I was like the product person on Twitter and, and, uh, tested out a few ideas that I thought it was going to try and be a CEO. So I tried to start a, uh, 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, we would attach, uh, uh, little oil tanks to the back of my car. And we were driving around filling up, uh, uh, cars in Menlo park. Um, I also realized people like their gas in the morning and at night.
Starting point is 00:07:21 So it's not a great time to be an operator. You have to wake up early and stay late. Um, so I ended up leaving the gas industry and luckily at that time, uh, I got a phone call from Tinder and I had used Tinder. I was in online data for, for, for several years. Um, uh, at that time you wouldn't say that out loud because online dating was still kind of a, uh, just a weird world and a weird thing to say you did. Um, and so I ended up moving to LA. I was one of their early product members joined in 2015. The team was about 55
Starting point is 00:07:54 people, big, um, really amazing product market fit, but a very disorganized organized organization. Um, we were just starting to, to monetize. So we were doing, um, about $20 million in revenue. I think a lot of people misunderstood tinder and subscription businesses and didn't realize what we'd become but um you know kind of like right place right time and also um just hard work but 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 sas revenue because it's 97 of our revenue subscriptions um and and from there just became kind of like twitter twitter famous um which sounds weird to say you probably understand it pump but um people were really curious to learn about tinder and how
Starting point is 00:08:44 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 tech world and and have since gone on to do a lot of things and now kind of focus on investing. Yeah. Let's go back to when you put three products to the top of Product Hunt. This is when 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? Yeah, sure. So, I mean, I think the biggest thing was they were really like very quick projects that I built, which enabled them to be a lot more timely.
Starting point is 00:09:27 Um, and so one of the products was a good example of Slack was blowing up. Um, 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. um and so think of it as just being a directory of all the best slack rooms for non-work topics and it did really well it was getting um a ton of traffic and then i got a letter from slack
Starting point is 00:10:07 asking me to uh cease and desist is what you call it asking me to take it to take it down um 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 um 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 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 uh this season this is this letter i got but um that was one of them and then another one was uh 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
Starting point is 00:10:50 been in the projects and you could adopt other people's startups um which again was like really easy to do just a little matchmaking product um and wasn't too too difficult and the other one was called request for startups and so it's taking a y combinator every year releases kind of a list of startups are looking to fund or themes that they're looking to fund um and so we would just go to all the vcs in silicon valley and ask them what startups they want to fund and um created uh 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 um 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
Starting point is 00:11:34 the weekend but um as you know if you just release a lot of things whether it's content or no code projects. Um, and, and they do well, people start to, to associate you with, with being a certain type of person. And for me, it was, um, just being someone who can release products at a, a fast rate. Um, yeah. What's so fascinating to me about this is, uh, 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, uh, what works, what doesn't work, you know, how to build, how to iterate, uh, you were 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
Starting point is 00:12:16 stuff you did later? Totally. Yeah. I was, it was more of frustration because keep in mind, I was also trying to launch this gas business on the Fed, um, which was just an impossible logistical business to run. And I was like, I can't release this because I have to deal with, um, literally like, like local regulations and governing bodies, but I can release this, this little cheap project on the weekends. Um, and then when I got to Tinder, I didn't have engineers. Um, uh, all I had, we ended up giving me access to this platform where you can send push notifications. Um, 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
Starting point is 00:12:59 tests through push notifications. So, um, and I'll give you a couple of examples. One was, we had this tool where i could draw a map around any um any location so i would i would spend my nights like creating little uh uh circumferences around around different venues being like if coachella was going on i would send them um what we called a swipe surge notification that just said like tinder's blowing up at coachella like open tinder right now um and i would do that for all the large events in the country. Uh, so that was one example that, you know, no engineers. And then we, we ran a similar thing on, um, in dating the biggest day, kind of like our black Friday is always the day after new year's, uh, because people make their resolutions. They're
Starting point is 00:13:47 probably hung over this on the couch, uh, and a lot of them want to meet people. And so we did swipe surge 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, if you think about that, just traffic. If you put those people in a football stadium, that'd be like 400 football stadiums. But that ended up being our highest traffic day ever. Then it got a TechCrunch article and then the whole company was like, who's this person on the side sending these cool push notifications that's you know driving our our highest traffic days and and then suddenly like people sort of take me more seriously at tinder but i think anytime you enter a new job or
Starting point is 00:14:34 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 um i think i became like known on the tinder team as someone who could do good work just because i was forcing my way into, uh, kind of into, uh, being a person on the team. Yeah. What's fascinating to hear is you're basically talking about various features, uh, 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 is in the product, uh, or they think of kind of what does this product solve for me? Um, but as a product leader, how do you kind of holistically think both about the user experience
Starting point is 00:15:17 you're presenting to somebody kind of the backend and what the product can do, but then things like push notifications, uh, you know, all sorts of prediction algorithms. Um, just how do you think about product and what makes a good product in today's environment? Yeah, I think, um, you always have to start with one core product loop that just works. Like, um, uh, for Tinder was when we tried to innovate on swiping for, uh, 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 uh 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 build off of um so you need you need that like foundation
Starting point is 00:16:04 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 uh 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 um 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 um and so a lot of messaging the the kind of highest retention apps are always messaging because you get the most push notifications generally um but you know
Starting point is 00:16:45 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 um 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 um you know i think that comes with pros and cons um 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 um and if you if you miss a push notification you're slow to respond to
Starting point is 00:17:29 someone, it might be, that might be your soulmate. Um, and so maybe, maybe you just miss like the person you're supposed to spend the next 60 years of your life with, or maybe it's just a person that you want to have a fun weekend with. So, um, uh, you know, it's, it's, it's a pretty high value activity. So we were, we were really lucky to be in dating, um, which I think is just a fun place to, to build in. Yeah. How much of this is like a master strokes of genius where, uh, 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.
Starting point is 00:18:02 And you're just testing so many different things and doubling down on the things that work. 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.
Starting point is 00:18:26 um and most of those projects actually don't end up working sadly um you know i think it's it's why uh companies do things like ab testing and you do try and roll out cheaper versions so you're not spending three or four months of engineering time doing those projects but um you know around all that is is just a ton of ab ab tests and experimentation um and a big a big metric of successful product teams is just your, your testing velocity. Like how quickly can you release tests? Um, how do you build that muscle internally? Uh, how do you get 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 AB tests because you don't have users to run those tests
Starting point is 00:19:15 with. But, um, um, 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 AB testing until probably four or five years into the company. And I'm sure there's still room to improve. Yeah. What about user research in terms of not a masterstroke 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? Yeah, definitely. I think, again, Tinder was such a topical product that you can get your user research in the back of an Uber or at a Sunday brunch. If you tell people you work at Tinder, they will just start talking for 30 minutes. You don't even have a chance to say a word, and they'll tell you all sorts of stories, and they'll give you plenty of product feedback.
Starting point is 00:20:15 Um, but we didn't really formalize the user research until again, like probably 2018 or so in which, um, Tinder was, was already four or five years old. And, um, you know, I think a lot of the feedback we got, um, 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 um is one-to-one feedback that you get yourself and the job of a product manager product team is to really consolidate that feedback and and build the right solutions but i remember there was a
Starting point is 00:21:04 point where towards the end of tinder i was actually on i started a kind of experimentation client, a team is, is, is an exaggeration, but I went off and I was like, I want to build an entirely new company within Tinder. Um, and it was the first time I think in a couple of years where I literally just, I identified our, our highest paying subscribers. Um, 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 will talk to us.
Starting point is 00:21:33 So, you know, we're, uh, uh, a public company and our users will still talk to us, but it It's 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 a hundred page printout of, of what your users want you to build. Yeah. And what about like gamification in the product?
Starting point is 00:22:05 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, uh, 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. Yeah. So, um, a lot of people refer 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 um a lot of people don't even plan to date they just they like the game of
Starting point is 00:22:43 swiping on people and seeing who likes them um and so we we definitely leaned into that i think um a lot of the the products we built were products that are already been built for dating which um has a ton of people in gaming move over to to dating because it's just a really fun place to build but um 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 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
Starting point is 00:23:29 track a lot faster um and we tried to lean into those playful moments and we added crazy video game like animations just 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 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 um
Starting point is 00:24:16 dating is is just kind of a 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 yeah before we move on to talk about the investing. 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? 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. Yeah, totally. So I think kind of my defining moment and the big product I built was Tinder Gold, which we had Tinder Plus, which was kind of our entry-level subscription package and tinder gold, um, really just moved the business
Starting point is 00:24:59 in a hugely impactful way. And the core feature in that was being able to see who likes you before you swipe, which actually was 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 swiping. Like you don't know who likes you and they don't know 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
Starting point is 00:25:26 as product people, um, in my job on the revenue team was to break the rules a little bit for, for a subset of users and say, Hey, if we, if we let 10% of our users, um, access this feature that, that kind of breaks the game, um, 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 In the case of, of, of Tinder gold and seeing who likes you before you swipe, um, everything was fine. It, it not only did increase revenue dramatically, it led to more matches, it created more conversations that got the, that engagement loop I talked about, um, was, was really sticky.
Starting point is 00:26:05 And so, but that was just huge and it was really fun because we were a public company. And so, um, you know, like nothing gets a team more excited when you're public coming than seeing your stock price go up. It's just addicting, especially in the Robinhood era where everyone's checking the stock price. We can pretend that doesn't exist, but every day, everybody, when you walk in the office, knows what the stock price is. Everybody gets really excited. When Tinder Gold came out, it literally 2x the enterprise value of Tinder. People were just pumped up.
Starting point is 00:26:41 The mood was always good when we walked in the office. Our team was really proud. It was, it was, um, again, like we, your internal, uh, kind of like, like respect just keeps going up if you build products like that. And it was just a really fun product to build. I think, um, you know, some things that, that were hard to do at Tinder. Um, we always want Tinder to be, and, and a lot of people push this in this direction. I think we want Tinder to be a social product because, um, 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
Starting point is 00:27:20 um it's a 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 um it just didn't like dating um at its core is kind of a one-to-one activity and um we always try to build like sharing mechanics and and all these growth kind of growth hooks but in some cases people view bringing their friends onto tinder as being competitive like if you go to a bar and you have a bunch of you bring a bunch of your uh cool attractive friends uh maybe that lowers your odds of finding finding success or finding your your soulmate um and so so social products were just really hard to build on dating and that was something we we we saw with tinder social
Starting point is 00:28:08 It all depends on if your friends are attractive or not, I guess. But yes, that makes a lot of sense. I lived with water polo players when I went to UCLA and they were six foot four and way better looking than me. So I had to be like the funny intellectual person on the side who would occasionally like meet my soulmate in that way. I love it. Let's talk about investing. 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 yeah sure so um while i was at tinder i was doing a lot of investing and i had i had uh launched a big analyst syndicate i was one of the larger syndicates just by like backers on the platform i was getting the really
Starting point is 00:28:56 cool companies through just being like a person in tech 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, AngelList has a product that lets you, uh, launch 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. Um, I just emailed my, my backers on AngelList and said, Hey, I'm starting a fund. Um, 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 managed i'm managing a fund uh and so then i i made a deck and i got more
Starting point is 00:29:43 serious about it and ended up um raising about a 10 million dollar fund over the course of six months but um was doing this at nights and on the weekends and and really there was a breaking point where I felt like I was doing both, um, product and investing. I was probably like giving myself, I would give myself like a C plus because I was just so, uh, 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 had a little bit of ADD. I just enjoy working on different problems during the day and investing's the perfect job if you have any any add um and so so yeah and then launching chapter one i think
Starting point is 00:30:29 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 um you need to to have something that just like stands out in the marketplace and for me i knew i loved working on product i knew i loved uh collaborating with with with founders that way and i also kept i kept asking founders in kind of those early investments like why do you this was after we we were we started working i was like why did you like let me invest and they kept saying like i wanted um 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
Starting point is 00:31:11 like the product person on your cap table um 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 ab 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 a tiebreaker a little bit um and and and then i thought to myself where do people really need help with product it's before they have product market bit and so it made sense to be an earlier stage investor and so we do precedence seed investments um and typically kind of look for teams that have uh a really unique lens on on on product and normally comes from being like a former vp of product or director
Starting point is 00:31:56 of product somewhere um or just a great engineer who has product sensibilities um so i end up working with like a lot of really uh like nerdy semi-artistic uh product people who just like love to to talk about this stuff all day long talk a little bit about your thoughts like you focus so much on product uh i've had people come on the podcast you 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 pre-seed and into the seed round for companies, especially the ones that you're working with that are very product focused. Yeah. I've talked with so many people
Starting point is 00:32:40 on this topic and the prideful product person in me says, product is everything. It's all that matters. But as you mentioned, I think distribution, especially right now, is probably more important and and that might go against what uh kind of the fun thesis is but the truth is um 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 um 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 in the app store and people just don't like downloading new apps um so that's that's a big question on the on the b2b side i think there's
Starting point is 00:33:26 um there's different unlocks whether it's hey you know we we have you know we just got through yc and uh we have access to 3 000 yc companies um that's a growth kind of a growth unlock there's but i'm always looking for different unfair advantages or um especially right now like i just did a consumer deal. And we're just stacking the cap table with, uh, TikTok influencers, which sounds funny. And I tweeted about this yesterday, but, um, I was like, which TikTok influencers are actually investing right now. Um, and so we made the choice to not have too many Silicon Valley investors. We, we want people who have audiences. And so, um, 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
Starting point is 00:34:17 out how to get those eyeballs. Yeah, it's really interesting. As you think through kind of building in the earliest stages, is it something that a pre-seed, a seed company, again, master stroke 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? 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
Starting point is 00:35:05 people to talk about your app enough where it becomes like a Sunday brunch conversation. I just believe in consumer that you need that. 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 15 or $20,000 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 um sometimes you can ab test products with medium posts like i'll sometimes i'll have an idea and i'll say hey i'm building this and i 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
Starting point is 00:35:56 you have to actually build the product if you say you're going to build them if you want it um but you can you can you can find ways to to get traffic i think you're just trying to see if people will literally sign up for it and if you have something um you know hopefully hopefully you can have enough traffic to measure retention over a period of 28 days or so um but yeah i i do think it's harder today because it's sort of don't be creative and figure out ways to to get that traffic because you can you can do it if you have a little budget yeah you're investing as a solo capitalist talk through kind of the thought process of uh 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
Starting point is 00:36:40 while now yeah i uh we were talking about this before the show but um i've always invested on my own and uh i've just developed a lot of confidence in my picking ability um 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 um just in the past year lp's limited partners have become so accepting of solo capitalists where um 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 um by being solo you can win deals and i let a a seed deal this 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
Starting point is 00:37:34 it would be this whole process. Um, I think the key is, is, is building a support system around you, um, 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. Um, I also think a lot of people, as you, as you, 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 fund and get going up, unless you find the perfect compliment to you. And I've gone through the process of talking to a few folks about partnering and it just hasn't, uh, you know, back to like
Starting point is 00:38:17 dating. 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. Um, but until that happens, I'm so happy doing what I'm doing now. 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, uh, but you don't have those investment committee meetings, you don't have partners that you can, uh, kind of bounce ideas off of how do you, you know, are there things that you, maybe you do to, to get feedback or have sounding boards? Uh, and then also how do you just think about the trade-off between speed and quality of decisions?
Starting point is 00:38:57 Yeah, sure. Um, so I think there's two parts of 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 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 there's this slightly different twist where this is actually the company to back. So having a prepared mind is a big part of it. Um, and the second part is building kind of building your, your support, uh, system in terms of, of peers and people you invest with. So, um, I invest really often with, with the same people. Um, I know we're on cap tables together, but
Starting point is 00:39:44 I invest with guys like, uh, Ryan Hoover, um, uh, great investors like Lee Jin, um, Harry Stebbings, uh, Tatum Rahul from superhuman. So we're always doing deals together. Josh Buckley another one um and and and so i'll i'll send deals to those people maybe i'll kind of like be around the hoop and thinking about committing and i just get the reaction so it's like having an investment committee but we all have different balance sheets and different funds um 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 going to be and a lot of people build peer groups within investing. Um, they try and go really wide.
Starting point is 00:40:32 Like they have a hundred people who they catch up with every, every couple of months. And it's, it's not very, uh, it's not a very intimate relationship, but 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. Um, and we challenge each other and it's, it's probably what it feels like to have an investment committee. Yeah. How do you think about follow-on investments in terms of you're investing at the precedence seed? Do you try to save a bunch of capital and invest at the stack? Do you just say, hey, look, I'm going to make a good decision precedence seed, and then I'll just take the dilution later on? What's the strategy or thought process? Yeah. For me,
Starting point is 00:41:14 I have reserves baked into 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. Um, I talked to a lot of people who are smarter than me, um, Mike Maples from floodgate, Chris Dixon from Andreessen Horowitz. Um, and they all insisted and they, they showed me data that, that suggested having reserves, um, would increase my performance as long as I could pick the right, uh, companies to double down on which is an entirely different ability um so i have 50 reserves i'll occasionally do um i'll see a great series a occasionally i didn't invest in the seed and if i do those i call my reserves like flexible reserves so i'll take money out of my reserve bucket and do the
Starting point is 00:42:03 deal even though i didn't invest in the pre-seeder seed um but out of my fund i think we've invested and 45 companies. I'm looking to deploy reserves into my top eight companies. I don't know. 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. I'll be curious to see how that plays out. Are there anything other than just pure returns that you're looking at to see how you'll measure whether you're a good reserve picker or not? uh for me again i worked on revenue teams like i'm very dollar driven and so um there's no there's no uh kind of like like i i'm going for for for returns and and there's uh i don't get
Starting point is 00:42:52 kudos for anything else so um i want to to 5x 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, um, that's all I care about. And that's how you stay in the business. 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
Starting point is 00:43:38 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 makes sense uh what are the some of the downsides to the solo capitalist model we talked a little bit maybe just about kind of being out on an island is there anything else that uh you've noticed is a downside yeah i think um i think sometimes you can be viewed in the market um or as entrepreneurs as as being kind of like an angel size check so if you if you start raising a larger fund maybe you raise you know 40 million dollar fund or even i've seen sell a couple of raise 100 million dollar funds and you're asking for a one million dollar check um and then they have this other fund that has
Starting point is 00:44:22 a platform and they have 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 capitalists as being your other view as a fund or your view 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 cap table and 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 um hard at the precedency you have to convince them that you're either the second or third largest check and so
Starting point is 00:45:08 and then maybe you make some some compromises on quality um 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 um and how you're viewed as entrepreneurs reviewed by entrepreneurs How has your process changed with the pandemic and kind of the lockdowns? Were you already doing most everything remote and not a big change? Were you taking a lot of in-person meetings and you had to kind of adjust? Yeah, it's been all Zoom. I've invested in, I think, 40 plus companies this year.
Starting point is 00:45:45 And I've met one of the entrepreneurs in person. And it was after I'd invested in them. And that's shocking to some people. Like I, 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.
Starting point is 00:46:07 Uh, but this is the new world we live in. And, um, especially at the precedent seed, it's so fast. Um, people are building products all around the world now. And so, and we're in a pandemic, so there's really no other option. And you have to figure out how 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 shake someone's hand and have coffee with them anymore.
Starting point is 00:46:42 Of course, I'd love to. I love meeting people in person. But if you do that, you'll probably miss the deal. 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 I'm going to paraphrase, but basically said, look, there's a lot of debate right now on every other city in the world, but San Francisco is still beautiful. I took that to be, you will
Starting point is 00:47:14 still spend a lot of time in uh in san francisco what's your general kind of take on uh austin miami la san francisco new york and uh you know wherever else internationally people are considering yes i posted that photo yesterday and my wife sent me and i i looked at 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 um not aggressively but i've been you know very open about the fact that i think san francisco needs to to change in different ways
Starting point is 00:47:57 um i got a text actually from my mom two weeks ago kind of uh it was like a mom to son moment which you still have when you're when you're adult uh when you're an adult and she said like why, you know, it was kind of like, why are you speaking so negatively about San Francisco, which I didn't think it was that negative, but, um, 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 barrier has 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 um to wake up and see people shitting on your city all day long
Starting point is 00:48:39 probably doesn't feel good uh and 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 kind of in the center of it all i've i've a couple brothers i have a large family one of them just moved to austin um in august another one's moving to miami in march and so I'm, I'm like the brother who's trying to figure out where I belong. And, um, for the moment I'm in LA, but I think as, 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. Um, and so it's very, the one
Starting point is 00:49:22 great thing about the pandemic is I think people have, have finally just, they're like, they're like chasing their like innate desires you're um it's kind of like this like 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 to do that but um and you're seeing people live in hawaii you're seeing people live all over the place and um 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 as has increased in many ways um so it'll be interesting to see how things shake out i still think there will be some pullback on the on the
Starting point is 00:50:06 san francisco narrative people will come back to san francisco um i just don't know if it's going to be quite the center of gravity that that it used to be um and so i think there will be especially if the city doesn't change in terms of, um, you know, I'm sure you've seen the debates about Chesa and the, and the district attorney and all the crime, it's not a safe place to live right now. And so, um, until it becomes a safe place, I don't think it will ever return to being the San Francisco we know and love. Absolutely. Before we move on to anything else, where can people find you or, uh, or send you deals if they're working on a company that, uh, they think could be a good fit yeah definitely uh so i'm jmj on twitter which is a great place to find me and then
Starting point is 00:50:48 um you know my dms are open although twitter's dm product sucks um but my dms are open and then you know there's a chapter1.com is my website so you can visit chapter1.com got it the twitter uh 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 uh i know if you want to go viral on twitter just complain about twitter dms because everybody will like your post and reshare it because it's like it's like the one thing we can all agree on it's just not uh a functional product i love it uh before we get into the rapid fire questions that i always ask everybody i pulled some questions from twitter uh and we'll kind of go through these uh drew
Starting point is 00:51:34 Morris, who I'm assuming has zero relationship to you, wants to know who is your favorite brother? Oh, man. He's my Miami brother. I grew up in a house with eight kids. My parents split, but they remarried. There's kids everywhere. Drew's a lawyer. He likes to ask really pointed questions. Honestly, this is going to be the most PC answer, but I love each brother for different things like drew and i have completely different conversations we talk about uh 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 pump you you have brothers but i have such different relationships with all my siblings and um uh yeah i i can't i can't take
Starting point is 00:52:24 one for you you know that he knows but he's gonna ask anyways i know uh liz keating asked uh for you to explain your college bedroom slash sunroom and explain the impact that it had on your life. Yeah, sure. So I lived, um, 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, um, uh, there was a sunroom in the back and everybody was picking their bedrooms and I ran and 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 it's just very like poetic place where i had a typewriter in there and i was just like
Starting point is 00:53:09 totally just like in this like fantasy world i didn't i was i was an english major um and so the sunroom just became like a part of my personality it's like jeff jeff's the one in the sunroom it was kind of just like a a weird first choice but um at the time i was always just trying to do like the most hipster emo thing i could do and it felt like living in the sunroom was like a place to be an author that's that's a great answer it makes a lot of sense uh dallas cohen asked uh if you could have lunch with anyone who is living who would you choose yeah definitely um so my grandpa's 100 years old uh his name is merv morris he started mervin's department stores which ended up becoming a a large public company and um i love talking to my grandpa it's just like
Starting point is 00:53:59 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 uh a bunch of of debt and uh 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 um who's you know been through multiple wars he's he was born on the 4th of July. So he's very, uh, 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, uh, he definitely wins that, that question. That's a fantastic answer. Uh, Jonathan Badeen, I think is how you pronounce it. Yeah. He wants to know what your morning routine is, which tells me he knows something I don't
Starting point is 00:54:45 know. So what, what, uh, what's he asking for? So Badeen, uh, is the inventor of the right swipe, which uh is his his great claim to fame well deserved but uh so when i joined tinder i was asked to to there's this website called my morning routine.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 uh 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 or it was just it was ridiculous and looking back on it I'm I laugh
Starting point is 00:55:33 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 morning routines. And I'm, I wake up when, when, uh, 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 think that's my personality at this point in life. I love that. And I love that he knows that you've got a great answer to this. That's why he's asking, uh, the last one comes from a pseudonymous account, uh, stock market hats. Um, but it was a, but it was a good question. Uh, what is your
Starting point is 00:56:19 best and worst investment that you've made? Yeah, honestly, a lot of my best investments, and I know you're deep in crypto, Ben, crypto bets. So compound finance was a really great one. Of course, Bitcoin has been a great one for so many of your listeners. But I love the quick returns on crypto and how you get liquidity really quickly. It's a really attractive thing. Um, 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, um, I invested in a company called Rome research in March that I'm really excited about. Um, and so we'll, we'll see what happens, but, uh, in terms of bad bets, I think I've made a ton of them and it's mostly things that you
Starting point is 00:57:07 didn't invest in, but, um, 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 Mike Maples a lot about this. It's just like, as an investor, you have to know what you're good at. I think 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,
Starting point is 00:57:29 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. 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.
Starting point is 00:57:52 What's the most important book that you've ever read? Yeah, for me, it's, it's always catching the rise is my favorite book. I love holding coffee. 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 pull me aside and he's like i think you could be a professional writer and so um and i tried to be
Starting point is 00:58:24 a professional writer i spent two years trying to be a screenwriter um and so so that that book really like led me down this path of um trying to to communicate better through through writing 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 up my body. And in 2020, I told myself, I'm not gonna fly anywhere, like I'm gonna chill. And then the world conspired to make sure that that came true because literally i was locked in my apartment um and uh and i eventually got a an eight sleep mattress and it's like thermoregulation and 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 yeah so i actually um uh developed sleep apnea and in high school when i was 15 i was i could not fall asleep for the life of me and i started taking tunnel pm um eventually i started taking ambient like it was it was a
Starting point is 00:59:34 it was not good. And then, um, I started to work out a lot more and just that helped a lot. So I was working out, um, I'd fall asleep better. And then, um, you know, all the way up to now I do have an eight sleep mattress. So, uh, Mateo will be happy that, uh, I got the aid, the thumb, uh, pad or the pad that goes on top of your mattress. And that's been just so cool. Uh, 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 uh i sound like an advertisement there's no uh 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 uh when the alarm goes off in the morning but that's that's helped a ton and then you know i try to again like i try
Starting point is 01:00:23 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 um but similar to you i've started to value my sleep a lot more and um i used to sleep four or five hours a week i was like cranking you know trying to stay up till 2 a.m and um i've just gotten to the point where i thought i 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 um but i think i think socially the value of sleep has just become such a topic and um it's something i'm paying attention to yeah i told mateo that
Starting point is 01:01:13 this was going to happen i said if i start asking people this like half the guests are going to be your customers so it's going to just be i was talking about eight sleep um the last question have is more fun and you get to ask me one uh aliens are you a believer or a non-believer i'm a believer i i when it comes to space i trust israel um and if they say there's aliens i'll i'll just go ahead and say that there's aliens so you're a what do they say galactic federation was the guy he said uh we're all part of a galactic federation and uh and they just don't want to tell us yet i did think so there was one part of of like someone was trying to make trump unlock all the all the documentation about uh aliens before he left left the white house and
Starting point is 01:01:59 of course today we have a new president and we didn't see those documents so uh i'm curious if biden will unlock the documents 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 gonna 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's somewhere else 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 um it would just light the world on fire that's a great suggestion don't let him hear that because
Starting point is 01:02:39 he will uh he will definitely try to try to do it uh all right you can ask me one question to finish yourself what do you got for me yeah pump i'm curious um obviously we met i think in 2014 or 2015 and um 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 um is really applicable to 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? Um, I'm sure there were other investors who told you you were an idiot and I'm sure there were a lot of people in Silicon Valley who, who wrote you off, but, um, what like freed you to just jump in and how did you not give a shit, I guess is
Starting point is 01:03:30 the question. Yeah. Um, so I don't think it necessarily was around like investing as much, you know, like, Hey, Karen, what other people thought or not. Um, I had this really unique experience when i was 20 21 years old where uh i was in the military went to iraq and uh 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 um and when i got there i had basically been pulled out of college to go and so i've 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 um and so these guys were worried about like
Starting point is 01:04:16 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 um you know kind of just being around them in the conversation uh 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 going to die. Like there's an end to this thing. Uh, and so when I came back, um, there was like a short period of time where I probably like, I implemented that learning in like a negative way. Like I had a motorcycle, I'd go like 120
Starting point is 01:05:00 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, um, 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. Cause you have to go through that specific experience to get that. Um, 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, um, I just kept telling myself was like the thing that seems least likely, uh, but has the most asymmetry is like the area to go
Starting point is 01:05:43 focus on. Um, 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 going to 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 centric 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 going to 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, um, and other people would warm up and kind of learn it as they spent more and more time
Starting point is 01:06:34 as well. Um, 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 going to be big and let me like go invest capital. But a lot of investors, like they'll invest a lot of crazy stuff. They don't talk about it. Right. Or they don't want to like go bang the drum publicly and like, you know, talk about a lot of their early stage companies until they know it's going to 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 to, I'm willing to learn in public. And so like, I'm
Starting point is 01:07:10 going to change my mind. I'm going to like do all this. And I think it was just the expectation setting of like, I may be wrong, but I'm going to like go through this entire journey in public. uh 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 um but you know looking back like yeah it's pretty crazy uh i guess um 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 uh that's great today when it's working but like god forbid something negative happens in the future like there's still
Starting point is 01:07:54 risk to some degree and so you just i think got to 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 want to do then, uh, uh, you know, all for it, but, uh, to just make sure you kind of do your own work. 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.
Starting point is 01:08:25 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, um, as an observer, as an observer, like, and it was, I think it's very risky to do that in ways because at that time, maybe you eliminate yourself from getting a GP job at a big venture firm, but you were okay with just going in a different direction with your life. And as an observer, it's been really fascinating to see. As you know, when I really started to learn about it, I thought I missed it, right?
Starting point is 01:09:06 I was like, oh my God, how did I not see this? So that was 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 two or three people that I always keep in the back of my head. Like I got the messages of like your torpedoing your career, like what are you doing? Um, and for whatever reason, it was just like, I just followed my gut. And like,
Starting point is 01:09:30 that's a horrible, uh, kind of theoretical decision-making framework of like, Oh, 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 just become more comfortable doing that and can't explain it. Um, but you know, worked out so far. So we'll see. I love it. Yeah.
Starting point is 01:09:49 My best decisions are always when I follow my gut and 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 i i have a friend i'll leave you with this one thing um he used to always say uh we're doing irrational things why are you trying to be rational right like kind of just you know stop trying to explain it stop
Starting point is 01:10:25 trying to defend it it's just like if you if you believe in it do it so um all right jeff listen where uh where can we send people at jmj on twitter at jmj on twitter you can follow me i tweet a bunch of crazy things um don't take anything i say too seriously but uh jmj on twitter and uh chapter1.com exactly awesome man all right well listen thank you so much for doing this we'll definitely have to do it again in the future thanks bob appreciate

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