Kevin Rose: His $100M/Year Watch Blog, Money From Digg.com, & Web3 Business (#382)

when I saw you went and did the watch site, uh, Hodinkee, uh, first of all, Sean, have you ever read that? Like, when I, when I heard, I was like, a blog? I, I like watches, I have Rolexes. I was like, a blog for luxury watches? What the hell is this guy thinking?

Did you, did you just say that it went from like a million or two in revenue and now it's— Sam said it's over $100 million.

Yeah, yeah, we're over $100 million in revenue now, man.

That is wild.

That's insane. What's up? All right, in this episode we are sitting down with Kevin Rose. A lot of you know Kevin because he's an internet OG. He created Digg back in the day. He was a seed investor in Twitter and a bunch of other cool companies. He was been a— he's been a VC, he's been a founder. He launched it recently, launched an NFT project that's done hundreds of millions of dollars worth of NFT sales. And so, um, Kevin's just been around for a while. And the cool part of the interview, if you, if you, you know, listen to it, you're gonna see very chill guy, very down to earth, very humble, and not a kind of like, oh my God, I'm gonna go take over the world, you know, bubbling over with ambition and a big chip on his shoulder. Seemed like a happy dude who was enjoying himself and had a ton of success in the process. And I like that. I like seeing different people who play the game with different— in different ways. And he's definitely somebody who's interesting. We talked about a bunch of his projects that you may not know about. So for example, is creating Watchville, this niche project for watches that grew from $1 million in revenue to now over $100 million after it got acquired and merged with Hodinkee. Um, then also we talked about how he hires writers. We talked about, um, you know, how he got into Twitter as an early investor and what does he do with his money? So he's got a bunch of money, uh, how does he invest it? Where does he put it? And, uh, it's, the answer's not, not what you may have expected. Um, the last thing we did at the end is we did the crypto debate. So Sam is sort of a crypto skeptic. Kevin is obviously a crypto believer and one of the kind of most well-known guys in the crypto scene. And we had a little debate where we talked about, is it all bullshit or are there some use cases? So I hope you enjoy this episode with Kevin Rose. I liked it. I think you will too.

We should give like a brief overview, overview, but like your resume, we don't really talk too much about like resumes and stuff, but your resume is like crazy long. So I've been following you forever, so I've known about your work. So you started Digg, which was— when did you start that? '04?

2004. That's right. Yeah.

And so you were— it was like one of the original, like, site, like, link aggregators, and it was like a cultural phenomenon. And that was crazy. And you were like— was it Time magazine that you were on the COVID of?

Like, you know, Businessweek.

Businessweek. It was like, here's this young kid taking over Silicon Valley. What's the internet? And who's this kid controlling it type of thing. And like it had all this hype, but like DIG didn't turn out maybe as wonderful as like we, we all thought maybe it could have done. But then you like had your finger on the pulse of all these other things you've done at DIG. You done— is it— I read it all the time, but is it pronounced Hodinkee?

Hodinkee? Yeah.

Hodinkee. A watch blog that also like sells watches. You are a partner at Google Ventures. You have this app called Zero Fasting that I use.

I love.

Partner at True Ventures, which I still think you're at now. You've got the, you got the The Oak, uh, uh, meditation app. And then I have a feeling there's like 5 or 10 other things that you just have brewing that like, I don't even know, like most people probably don't even know about, but you're basically, my point is, is like you're kind of an internet OG and you are incredibly prolific. I mean, does that kind of summarize it?

Yeah.

I mean, the, the most recent thing I started was Proof, which is our, our venture into the world of NFTs. And so that's, that's the only thing, uh, missing from, from that. And that, that's about, um, 10 months old now. So that's on the newer side.

So from the outside, if I look at this kind of like collection of, or like the career path, it looks very random. It's like, you know, from, uh, you know, from venture-backed to angel investing to venture investing to kind of like niche communities, uh, you know, these like kind of apps that are like simple, like, uh, like meditation or fasting. Um, you did a podcast, you did a show, you know, you've done a bunch of content, you did a bunch of different things. Was there a method to the madness? Is this— do you just describe it as random, or is there kind of like some underlying theme to this whole thing?

Yeah, there's— I would say that I've always been one, ever since I was a little kid, to just tinker and just to play. And if there's any method to the madness, it is this common thread of exploration and just wanting to, if I see something that doesn't exist that should exist, I want to go build it. And I've done that a handful of times, um, you know, probably at least 10 to 15 businesses of which, you know, 90% of them go to zero. And then there's a few that pop and become, you know, pretty big. So, um, it's just this idea that, uh, I don't want to sit on the sidelines if there's something that's exciting that needs to be built. I'd rather just spin up a team and go after it.

Of all those projects, I'm, and I'm actually gonna exclude Proof from that because, uh, I want to talk all about that in a little while, but of all those projects that I mentioned, which one has been the most financially successful for you personally?

Hmm, that's a good question. Um, certainly I would say when I was in the middle of Web 2.0, which was the, the when Digg was at its peak, which was about early 2006, we hit around 38 million people a month using the site. Of the Web2 properties, it was one of the largest. It led me to sitting down and dinners and conversations and hangouts with the Jack Dorsey's and Evan Williams and Zuckerbergs and all of the household names that became these big products. And they were just friends. And so because of that, it was more like, hey, well, do you want to invest in my new thing? And so I would say the investment side has definitely been the best financial returns. I did start a media company that— well, I would say there's two things that— well, three that are— two are unrealized in Hodinkee. Um, which is, is, is going to be crazy. It'll, you know, it's over $100 million revenue a year now, which is nuts.

Whoa, really?

Um, and then we have, um, you know, uh, the stuff I'm doing at Proof right now, which has just been another crazy rocket ship. But in terms of like true exits of businesses that I've started, um, Revision3, uh, where I was the co-founder, was a media company that became, um, Discovery Channel's digital arm. And we sold that for $35 million back in, uh, 2008 or something like that. So that was probably the biggest company sale that I've had. Um, but you know, they're much larger on the more angel investment side.

And maybe that sale gave you the, the ammo to do the angel, to do angel investing, or would you have been able to do it without it?

A bit, but I was already starting to do small investments prior to that. So I didn't have any money. I didn't come from money. But when DIG really took off and we were a couple years into DIG, investors, and this is a very common practice, it doesn't get talked about a lot, but investors come around and they're like, "Hey, you're doing this round of financing. Can we take a little pressure off of you as an entrepreneur and buy some of your stock personally?" And so I sold a little bit of my DIG stock enough to give me the ammo to go and do small seed checks, you know, and put, you know, $25K into, you know, Twitter's seed round and, and put, you know, $25K in, or it was more into Facebook, but, um, they were a little bit later stage. And, and so it was, it was those little tiny checks that, you know, when they turn into multi-billion dollar businesses, uh, were pretty meaningful.

How much does $25K into Twitter and Facebook early on actually turn into?

Millions of dollars.

I mean, that math is even hard to comprehend. In Twitter's seed round, what was the valuation then?

Well, it was difficult because they were a podcast company doing podcast software, and then they did a new round. They pivoted into Twitter. And so, oh gosh, I'm drawing a blank on the name of the podcast.

Audio.

Audio. That's right. They were Audio. So, um, Yeah, I didn't invest in Odeo. They had become Twitter. And I asked Ev, who I was the tightest with at the time, because I didn't really know Jack that well yet. And I asked Ev, he was CEO, and I was like, can I invest? And there was no round available at that point. But he's like, I've got this engineer, Blake, that was leaving and had some stock and was like, do you just want to buy some of the stock? And I was like, yeah, that sounds great. I'll just buy some of the stock.

I think Gary Vaynerchuk said the same story and he bought it from him.

Yeah.

Yeah. So here's the funny thing. So I bought in from Blake and then I told Gary that Blake was selling some and then Twitter ended up actually, they had a preemptive round come along that really like 5 or 10x their valuation. And then Blake was like, oh, whoa, whoa, no, there's a new valuation now. And he charged Gary the new price. So Gary's still pissed at me because I got this really cheap price for Twitter stock. You know, and then, uh, and then Gary had to pay the more expensive price. But that was a funny little—

what do you think Blake's saying right now? I mean, Blake probably just— he did fine.

He held on to like half or more. And so, you know, he probably— I don't know, he— if I had to guess, he made $50+ to $75+ million or something on it. He— I'm sure he's okay.

Did, uh, at the time, because Twitter kind of had like a— well, there's like Odeo kind of failing, Twitter, who knows, um, and then there was like this like small community of people in Silicon Valley that were like using it back when it was like texting the, the, your updates out. Um, like when you're, when you were writing that check, did you feel like this is the, you know, the next big thing or was this kind of like, I don't know, my friends are smart, let's see, or where was it?

I felt like it was the next big thing because there was, I, I loved, so as someone that was building a social graph of sorts at, at Dig, you know, there was always this idea. Back prior to, um, excuse me, prior to Twitter, that was, um, bidirectional friendships. So, you know, on MySpace and Friendster and all the others that had come prior to Twitter, you had to actually know the person to see their content. So it was like, I, would you like to send a friend request? Yes. Do you accept this friend request? Yes. Right. And it was like same thing with Facebook. And when Twitter came out with that model of just this idea of following, And, and, and it allowed, like, there was no celebrities on the platform. It was like me and Leah LaPorte and a couple others that were the top followed people on the platform at the time. Um, but I, I thought to myself, like, wow, if this catches on with the celebrity crowd, it's just going to be insane. It's going to be because everyone will just want to see. And also the barrier to entry, a lot of back then it was, it was, um it was impossible to get, uh, you know, celebrities to sit down and kind of, um, do technical things because they— we didn't really have smartphones. But the fact that you could text to that number, that shortcode, just what you were up to— anybody can do that. It doesn't require any special software, doesn't require you sitting in front of a computer. And so it was just so dead simple to use. It felt as though, as I saw the tech crowd you know, um, kind of catching on, uh, it, it, I knew eventually it would spill outside of that, that small vertical of users into the mainstream. And if that, when that would happen, that was the bet. And when that would happen, uh, if and when that would happen, that would, it would, it would blow up. And, and it did. So that was, that was awesome.

And I remember I've also seen, uh, you did a video back in the day when Square was like a prototype. It was like a YouTube video. I remember you, you were like, hey, yeah, check this out. Like, you know, here's this little Square and you could plug it into your phone, you could take credit card payments. You're like, and it was not even released yet. And you were like, you know, promote. I think you did. You invest in that too, because that would have been like, yeah.

So that's a great story because I hit Jack up and I was like, hey, I heard you're doing this new credit card thing. I'd like to be an angel investor. And he's like, oh dude, it's oversubscribed. I'm sorry. Like, we've closed the round, like blah blah. And I was like, damn it. I'm like, well, let me see if I can help you in some way. And so he gave me a prototype and I just went and recorded a video and it got a lot of traction and it got a lot of people excited about this new product. And it was like an early glimpse of what was to come. And it started getting, you know, tens of thousands of views on YouTube. And he calls me back and he's like, I had an investor drop out. I've got some room. Do you want to put a check in? And so that's what got me into their seed round, which was awesome.

What was it like? You know, I lived in San Francisco from 2012 up until somewhat recently. Sean's still there. It's definitely a bit different now because like startups are quite popular and, and Jack's— and Jack Dorsey is like basically a celebrity. Mark Zuckerberg is obviously a celebrity. What was it when back then in the, the, you know, '04, '05, '06, you know, 2010, when these things were just getting going, did you actually think that a guy like Jack Dorsey was going to be like this kind of like titan of industry like he kind of is? Like, what was it like being around some of these folks early on when they were just, you know, you guys were just messing around?

Well, it was— you met a lot of entrepreneurs back then, and there was— it was clear there was a few people that stood out as just being wildly creative and just deep thinkers. And I was really drawn to those folks. I wanted to just like pick their brain more and get to know them better. And so, you know, one of the things that struck me is just how mature Mark Zuckerberg was when he was younger. Like, it was, you know, I'm quite a bit older— excuse me— than he is. And How old is he now?

He's still only like 38.

He's younger than that. Oh my God. Yeah. So how old is Mark? That's— oh yeah, you're right, he is 38.

Yeah, that's still— I mean, he's in his 30s. That's pretty wild.

Yeah, it's, it's, it's crazy. Um, he was, he was really young. Um, so yeah, so when I met him was 2005, I want to say. So he was 21. Wow. So he was 21 years old and I remember just thinking about how put together he was and how well-spoken and just what a deep thinker he was about the space. And he wasn't winging it. He was taking it very seriously. And that was a big shock to me. I remember just those conversations being like, I was like, wow, for 21, I was definitely not as put together as he was at 21.

What's something he said that made you think that?

Well, one of the things that I was always frightened by as an entrepreneur in my youth was just this idea of would people take me seriously and could I admit when I didn't know something? And was it okay to— I tried to hide my vulnerabilities as an entrepreneur and he just came in and was asking so many pointed questions. You know, I asked him about some of his hiring and firing practices and how he would edit his team, how he ensured that he made the right hires on the engineering side, because it was, it was, that was a very challenging thing to do back then to scale websites. You were like racking your own servers and, you know, there wasn't the AWSs of the world. And we were talking a lot about that. And it was just, it was one of those things where, He just told me that he just— It's the obvious stuff. You surround yourself with people smarter than you, and then you ask a lot of questions and you're not afraid to ask those questions. So back then, I had some great investors and board members, but at times I was a little hesitant to be like, "Hey, I don't quite understand how this works. Can you help educate me?" And I think it was due to my lack of For some reason, I thought because I was a college dropout that I had to hide that. And they would be like, if I asked a question that I should have learned in college, that it would've looked— had egg on my face. And so there was a lot of nervousness around that. And just to see Mark just be so open and just curious. And there was no— it was clear that if he didn't know something, he was going to get to the bottom of it right away. Um, it was, it was inspiring.

I had a, I had an experience just like that when we were selling our last company. Um, I met with all the big companies, Facebook, Google, Amazon, whatever. We also met with Discord and I go in, I meet Jason, who's the CEO of Discord. And I'm like pitching him on like, you know, basically if you bought our thing, like it would add this dimension to Discord, it would be awesome. And what I was so used to was most founders. If you, if you're just kind of saying how awesome they are and how they can take over all these different, how there's so much more they can do, how this is just the beginning and how there's all these different ways that they can expand. Normally they're like, yes, yes. Yeah, yeah, totally. We can do that too. We can do that too. It all sounds good. And he was just sort of like, you know, I would acquire you guys cuz I like you and I like that you came in and you had this like whiteboard and you just like painted a picture for me. Um, but we won't do any of that. And he's like, um, no, that's not what Discord should do. What we should do. And he said no. And he was like, we should just be this one horizontal utility that does this one thing. And, um, that's our, that's, that's the right strategy for us. And he was the first guy that said no when I was like kind of giving him some ice cream of like, you can have this too.

Right, right, right.

And, and I just thought, oh, that's what, like, this is, this is probably what Zuck was like, you know, this is probably what somebody who was focused was like, cuz back when Zuck was building Facebook, it was like MySpace was adding music and then TV shows and doing these like brand deals. And like, he was just like, nope, real names, simple profiles. We're just gonna let you like, you know, communicate and add photos and do this stuff. And like he said no to a bunch of different things, which is why Facebook was so much such a cleaner site than MySpace and all the other competitors that were out there.

Yeah. I would argue they've lost a lot of that cuz they say yes to a lot of the cloning of features of other, other competitors. But yeah, you're right that relentless focus is so essential. And oftentimes it's, it's more what you say no to than what you say yes to on the product side. You know, I, that totally agrees and vibes with me for sure.

Do you sort of, when you're doing all these projects, back to the projects, do you have like a set of rules? Like, for example, I know a guy who is incredibly successful. I talked to him one time, his name's Kevin, or a couple of times, his name's Kevin Ryan. He started like MongoDB, Business Insider, Gilt Group, all these like amazing companies. And he was like, well, I just do back of the envelope math and then I give each project 6 months and me and my partner typically fund it with $300,000 and we kind of like feel it out. It's a little mathematical, but it's also like, well, let's just see what happens in 6 months and see if this is promising and we'll decide. Uh, and so he is like 6 months, $300K, can we make something cool? And I talked to Atomic Labs the other day, you know, Atomic Labs, they're like that incubator that's, They're not really an incubator. They like start companies.

Hmm.

And they said something like, they're like, yeah, well like sometimes we'll only spend 50 grand and like 2 months or something like that. Do you have, uh, like something like that when you're starting a bunch of your projects, like the fasting app or the meditation app where you're like, I think you did another one, Milk, or is that the name of the production company?

Yeah, that was the name of the, the kind of incubator studio. Yeah.

Like, yeah. Do you like have like rules for what you're looking for?

Yeah. I mean, I guess the question really comes to when you decide to kill something or sell it off or get rid of it or move on to the next thing. And oftentimes it's because your original kind of thesis around either the market size or just the concept behind it just didn't take hold. And so I don't have any hard set number of months. Sometimes you're early. So, you know, uh, the fasting app, for example, um, you know, when, when I launched Zero, it, it sat at, you know, tens of thousands of users for the first 8 months. And then fasting hit and it became more of a household thing. And people were talking about intermittent fasting. It was all over TV and different, you know, places were picking it up. And so people were just naturally searching for fasting in the app store, cuz that's just what they do. And then that's when it exploded to, you know, hundreds of thousands and, you know, a million plus monthly active. People doing fasts. But it was— had I shut that down after the first 6 months, you know, it had been too soon. So something like that, if you just believe the market is not quite mature enough, I typically put it into a little bit more of a maintenance mode. You know, I got it to that first version where I felt like this is a useful utility for people that are looking to learn more and get into fasting. Now let's just let it kind of organically build from here. And we were seeing, you know, nice, slow, consistent kind of week over week, month over month growth, but nothing explosive like you're used to seeing in a high-growth startup. So that one in particular was just like, let's just wait around. And then other times, you know, you create something and you've just clearly missed the mark. It's like we created this app called Tiny, which was a fun little photo sharing app that was— Yeah, I used it.

I liked it.

Oh, you did? Awesome. Yeah, it was these little, little small postage size, uh, looping videos with no audio, and we thought it would just be like a little bit more quick, a little intimate way to show kind of how you're traversing throughout your days and weeks rather than having to take the time to set up to look all perfect in front of your perfect Instagram.

There was less pressure literally because it was small, right? Exactly. That part was actually kind of true.

Yeah.

And, and That was a crazy one because, you know, we launched and it just, it caught fire immediately and we had, you know, hundreds of thousands of downloads in the first week and then it just died off completely and everyone was like, ah, that was a fad. That was a, that was a fun little fad. And that one we shut down pretty quickly after that because it was clear that it was a fun little thing, but, but there was no depth to it. It was a, it was a feature, uh, not, not a real product. So, um, yeah, it varies from product to product, I guess, is the best answer I can give you.

Cool. Um, okay. So, uh, you talked a little bit about like, you know, which one was the most lucrative. Okay. Yeah. Obviously angel, you know, sort of angel investing in Twitter and then getting into, you know, Facebook and others is, is it works out well. Which one was the most fun? So which chapter, uh, was the most fun? And kind of with that is I'm on this mission. I just, you know, like after selling companies, like I got time and some, I was like, all right, well, what's the priority now? I was like, I wanna find out who's having the most fun in their career. And like, Cause that's what I wanna do now. I just wanna have the most, most fun type of crew who's having the most fun with their life right now. So I wanna know for you, which of your projects was the most fun and then who do you see, who could, who's a blueprint I could look at where you're like, this per— I've met this person, they're having a blast with what they do.

Yeah. Well, I would say that the, you know, there's the, the nice thing about starting your own businesses is you're, you're doing it because there's a personal drive behind it. Like I've never created anything because I thought, here's an opportunity to make money. It's never been that. It's— we were talking about this as we were just, you know, prior to hitting record or whatever about the little podcast Case Holder on Amazon, right? And like, there's, there's, there's sometimes there's these little businesses where you see a broken piece of an industry and you're like, well, gosh, if I went out and created this, I could sell X number of units per year and it'd be a great little profitable business. And like, that's never really interested me. It's more about the just the creativity of it all and just the exploration of an idea that I'm drawn to. And so no startup is fun. They're all roller coasters, loop-de-loops. Like there's the chaos of all of those things, right? Especially as you grow your team and there's HR issues and people getting sick and products not getting shipped on time and customers being upset. And you know, it's never going to be just like this perfect dream. But that said, as long as it's something that you're just naturally drawn to, I'm always having a good time. And I'd say though, that said, that's kind of a little bit of a dodging the question, but more recently when I've kind of gotten into the art and NFT side of things, that world and the world of cryptocurrency is probably the most fun because it is so blue ocean and there's just so much to be built there. It's not building yet another app and competing on, on CAC in the App Store. It's like, it's, it's really, um, there's, there's so many different directions you can go. Um, and, and very few, well, there, there, there is, there is a decent amount of, of high quality entrepreneurs in the space, but not as, as much as say, you know, building something for the App Store. So. I enjoy kind of more the blue ocean aspect of that world, man.

I remember when— so basically I started this company called The Hustle. It was like a daily email and we sold it for— we bootstrapped and sold it for tens of millions of dollars. It kind of— it kind of sounds a little bit similar to what you were saying about your story. I lived in San Francisco and I started a media company because I was like, I'm not capable of starting a tech company, but I wish I were. And also I'm good at writing. When I saw you went and did the watch site, Hodinkee. First of all, Sean, have you ever read that? Like when I, when I heard, I was like, a blog? I like watches. I have Rolexes. I was like, a blog for luxury watches? What the hell is this guy thinking? Like he just like, he, he, he like—

It started as something else, right? You started it as like Watchville or it was like a, it was something else. You got acquired or merged and you became like the CEO of this. I remember looking at that, just being like, I have no idea what the hell he's doing. I don't wear watches, so I had no— I was completely out of touch with it. And it just seemed like, you know, a hobby project at the time. And then I started looking into it and I was like, oh wow, there's like a huge passionate base around this. And this company makes a lot of money and has been around for a long time.

I don't think it did make a lot of money, did it? Like, I remember I read that and I was like, I like this business because I'm into it. But like, this guy is frankly way above this. What is he thinking? Like, this is— he's like, this is needlessly hard.

Well, Watchville was— so I, again, like, just kind of like personal passion stuff. So I was into watches mainly because when my father passed away, he left me with a single watch, and it's something that I wear every once in a while. And it was— for him, it was like, to afford a single Rolex in a middle-class household is a big deal. Like, that's like back in the '80s, you know, when my dad bought that, he was just like I've made it, you know, I have it. And I'm not talking about one of the crazy Rolexes. I'm talking about just the standard Day-Date, kind of like, you know, simple Rolex. And like, that was like the one thing he was really proud of, you know, that and his like GMC pickup truck. Right. And so, um, those, that was something I was left with. And then I started reading, uh, some of the content. So Ben Clymer created Hodinkee, the actual blog, and I created Watch Phil, which was an aggregator and an app. That brought together all these different sources so that people can read this stuff on the mobile, uh, on their mobile phone. Because a lot of, as silly as it sounds back then, most of the, excuse me, most of the watch sites didn't have, um, mobile versions of their site. So they were on just like old, old software, publishing software that was, that was just horrible. So I, I, I made it all very readable. Um, push notifications, like all this stuff, just like kind of a wrapper for like all of this great content. And it just started growing and growing and growing. And I had a lot of eyeballs, like some of the biggest collectors were now using the product. And, um, you know, I, Hodinkee was the most kind of best prominent, um, source of this content that took it very seriously. So it was, um, you know, they had a couple full-time writers. And so I talked to Ben and said, hey, you don't have the tech team here. Let's merge and combine forces. So We, we merged the two companies together. He was 3 or 4 people and I was 3 or 4 people. I moved to New York, became CEO. At the time he was doing maybe $1.5 million to $2 million a year in revenue. So just enough to kind of do payroll. And we grew it from there and then turned on e-commerce and then started selling and creating partnerships with the big watch brands. And now you know, as authorized dealers represent, you know, several dozen of the big watch brands that are out there. And that just became a massive, um, it was still a relatively unknown back then whether or not people would actually spend large sums of money over Apple Pay, right? And so, um, I remember we had someone from Apple that was, um, you know, helping us on when you get to a certain size, they kind of give you a little bit more concierge help on the apps stuff. And They said that they had seen their, uh, $250,000, um, transaction come through Apple Pay, um, on an American Express. And that was like the largest known transaction at that time that had been done over Apple Pay for a sight unseen, uh, vintage Rolex, which was, uh, which was kind of crazy. But anyway, yeah. So that, I mean, new, new, new luxury watches are double-digit billions of dollars a year. Um, in terms of market size. So it's a big industry that many people— it's not as apparent in the States. When you go overseas, you'll see how in Europe there, you know, watches are so much more kind of a type of thing that is worn versus smartwatches are more of the norm or no watch at all here in the States.

Did you just say that it went from like a million or two in revenue, and now it's— Sam said it's over $100 million.

Yeah, yeah, we're over $100 million in revenue now, man.

That is wild. That's insane. And a lot of it's commerce. I mean, you guys, like, when people talk about content and commerce, I think most of the time it's nonsense. Like, BuzzFeed talks about it, and I'm like, I don't know, man, I don't think people are going to be buying a lot of branded BuzzFeed pillows and shit like that. Or like, they had that Tasty thing. I was like, I don't think people are going to buy a BuzzFeed oven. I just don't think that's going to happen. And you guys did it. And I was like, I don't know, is this like going to be a thing? It seems so challenging. But you guys are a perfect example of that. You know, the other good example, I bet you go to Bring a Trailer. You go to bringatrailer.com.

I've been to Bring a Trailer many times.

Yeah, it's awesome.

Hodinkee, it's one of his favorite sites, actually.

They are awesome. And so they've done the same thing but with cars where basically it's like this perfect tie of like, I just, I bought one car from actually those websites and but I read it every single day. I'm like, let's just see like what they're going to write about, what cool cars out there. And then you guys did it with watches and I loved your videos with John Mayer where he talks about his watch collection and all that shit. It's awesome. But what, what other verticals or what other like industries have you thought, man, maybe I could actually do this model? I've always thought software, but like, that's not nearly as sexy and cool as watches and vintage cars. But has there any— it's like when you were like thinking about this model, I bet you're at night, you're like, I'm not gonna do it, but I bet you I could apply this here, here, and here.

Yeah. I mean, in, in some sense, that's kind of what we're doing right now in the world of NFTs where they're— everyone that's armed with Photoshop can create a digital, um, piece of art on the blockchain. And there's this mad rush into the world of NFTs, but there is just a ton of clutter. Right. And, and just. A ton of, of, of, of projects to sort through. So what we created with Proof was this, this idea of, you know, it's the same thing with Hodinkee. It's the same playbook. It's this curation with a point of view where you can have a strong editorial team come in, um, that isn't talking about the flipping side of the industry, that isn't talking about how to make a quick buck in NFTs, um, that is really talking about what would you buy and hold for the next decade plus, right? And the playbook that, that Hodinkee nailed so well was that we took editorials so seriously and really hired out just an absolute stellar team of writers that had a deep understanding of the world of watches. And not just an announcement, this is a new watch that was dropped, but an understanding of the, the mechanics of the internals of the watches. So they could tell you about the different movements and escapements and why certain complications were harder to pull off technically than others. And so it was a real geek's blog. And with that technical, hardcore writing developed trust. And so you, and once you have the trust of your readers, um, then you're able to extend commerce in a meaningful way. And it's not asking them to buy, you know, uh, a microwave or some like inexpensive or a throw pillow. It's, it's, it's saying, we have your trust. This is, uh, what we believe to be a very important watch or collectible. And because of that, you know, you're willing to pull the trigger on a, on a $20,000, $30,000, $50,000 purchase. So, um, it's— trust is so essential.

Do you think that— well, I, at The Hustle, we were trying to— we hired a bunch of writers. Sean hired some writers as well for his thing, is a crypto thing. And I, I've always debated this in my brain. I'm like, do I hire good writers and teach them about business, or do I hire smart business people and teach them how to write. What did you find was the best way to do that for watches?

Yeah, I mean, the best way to do that was to find people that had the natural, organic, built-in love for horology, like just this desire for all things mechanical watches. So, you know, we would have writers that— if you take, for example, like the Speedmaster, the watch that made it to the moon from Omega, Um, you know, they could tell you every single variant and movement change and the reasons why, and they were just super geeky on this stuff. And they may have been just like B+ writers where you get them, but they had the technical knowledge in their brain. And that's a lot easier to fix because you get them to put that, that technical information out, uh, in draft form. And then you just apply an editorial layer over the top of it where you have copy editors that come in and help, you know, stitch together a better, more cohesive story before you actually publish it out to the world.

Yeah, I love that.

This data is wrong every freaking time.

Have you heard of HubSpot? HubSpot is a CRM platform where everything is fully integrated. Whoa, I can see the client's whole history—

calls, support tickets, emails— and here's a task from 3 days ago I totally missed.

You're a pretty chill guy. When do you get like really fired up? Like what, what gets you excited? And, or in a good or bad way, like, um, you know, I get really enthusiastic about the most random shit, like the most, uh, it'll be like a creative project and I'm like, I bet I could pull this off. And I just go like, I just get too excited about it. Sam has that same thing, but he also has it where if he feels he's wronged, Sam's like, you know, willing to fight to the death about it. And so he gets really pumped up. What gets you really pumped up?

Raid, raid Rage is my fuel. I love fighting.

Yeah. So for me, new ideas and working with creative people is the most kind of like strongest source of fuel for me. So when I get together with an artist or a fellow entrepreneur, and I actually, it doesn't have to be someone that has created something big. It has, it's rather someone that just has wild ideas that that are potentially, um, uh, just new, new ways of looking at the world. And so you meet a lot of entrepreneurs that are opportunistic, iterative entrepreneurs where they'll see something, they'll say, oh, there's some rough edges on that particular product. I'm gonna go sand 'em down, make it easier for consumers and go launch a business. And they have great success. I like the ones that are just like really thinking about, um, entire new verticals or just flipping something completely on its head. In new and creative ways. So that is what I'm really drawn to from just a straight idea point of view. And so entrepreneur-wise, and when I invest in some of these startups, those are my favorites, are those crazy, more world-changing entrepreneurs.

In terms of the rage side of things, Dude, you've had a, you've had a bunch of rage-inducing moments. I've, I've followed your career. I've seen, I've seen you with the fucking raccoon.

Yeah, I saw you with the raccoon. We saw that one.

I've seen people protest outside your house. I've seen you get in trouble for like, I don't know, wanting to demolish like a historical building. I don't know like the whole story, but like you, you've had, you've kind of been a target.

Yeah. I mean, those, those all have their own unique story that the historical building thing was definitely not true. That was a, that was a pretty funny one in that, um, but, but that was, uh, that was just people wanting to keep an old house up in the neighborhood and they called it historical even though it really wasn't. Um, uh, we wanted to take it down because it was filled with asbestos, which we didn't want to live in a house that had asbestos in it. But that's a whole nother story. Uh, the rage stuff, you know, the, the, the, the last 4 to 5 years of, of my life has been spent trying to kind of master my own mind. And I think that if you can't come to grips with your own personal peace of mind, it's a horrible place to be. And so, you know, I remember as a young entrepreneur just kind of being on this 24/7 hustle to go build, build, build. I got to win. I have to win. I have to win. And it created a level of anxiety that was not good for me. And so I think that's probably why you saw me kind of do things like the meditation app and other, other things because I— it was just a natural forcing function for my, my own self to like take some of that stuff more seriously. And so, you know, um, I just want to be able to, to be able to sit and not have to have my mind be always on. And that, that's kind of been my goal, and it's something I'm still, I'm still working on so that it's not like— I remember there was this interview with Elon Musk, and I'm not comparing myself to Elon Musk, but there's one thing that I, I can certainly relate to where he talks about how his mind sometimes just never shuts off and he's always thinking about things, problems, new ideas, like all of these things. And, and it's, it's, for me, it's always been that, that has been not a blessing, but something that has just been, has weighed on me. And I've always tried to, I guess the big push in the last few years have been to try and wrangle that.

What kind of gets you all hot and bothered now where you're thinking about like the new industries or the things that excite you? What, what ideas would you pursue?

One caveat, that you're, that you're not currently pursuing. So, uh, because it's easy to say, oh, I'm excited about this project I'm doing. I think, uh, like for example, Palmer Luckey was on the last episode and he was talking about, all right, we're like, you're doing Anduril, you did Oculus, what are the ideas that are on your kind of like, oh, that's interesting, but like I only got one me, so I can't go do it. Cause I think that's, that's the most interesting to the audience. Um, and to, and to ourselves. And that's actually the origin of the podcast. Me and Sam have more ideas than we have time to do them. And so we're like, well, if we just say them out loud here, maybe people will take 'em and run with them or, or find something interesting in it.

By the way, have you ever talked to Palmer, Kevin? That guy is wild.

No, I've never, I've never chatted with him. I, I, I have to go back and listen to that episode though. I'm, I'm really curious to know. I've, I've, I've seen some written interviews, but never, never anything on video form.

It went live yesterday. It's on like our YouTube and most of our listenership's on like podcast feeds. He is— he's something, man. That dude, that guy's eclectic. He's just like enthusiastic about everything. He like knows a lot about a lot. He's like biology, but more—

but almost—

he's as smart but is more common. Do you know what I mean? Like, he's— for some reason I can relate to him even though I know that he's just like so much more smarter than I am.

Yeah, I had read some stuff and I don't know how much of it is true, but some of his company stuff that he was creating around drones for tracking people and some of this stuff—

controversial.

Yeah, I just— it doesn't fit well with my ethos, so I haven't really followed his career as closely. But I'd be curious to listen to the interview for sure.

I think it was probably, it was probably our best guest episode. Oh, that's awesome. And like, we've done a bunch of 'em. And the reason why is he's like, you know, he's like, A, he's like pretty genu— like he's pretty, A, he's high energy, but he's like direct. So it's like, you know, why do you do this? Or how'd you think about this? And he's like, for example, he's like, I thought about, you know, I'm kind of overweight. Could I like solve obesity? And he's like, you know, but here's what doesn't work, telling me to, eat less of foods that I don't like the taste of and blah, blah, blah. And so he's like, he's like, my solution was, and I started prototyping this in my house, was to just instead of Beyond Meat and stuff where they try to make like a burger outta chickpeas, he's like, I wanted to just make fake food out of oil. Zero calorie food that tastes amazing because oil tastes amazing and we can manipulate oil into anything. We could turn oil into candles, we could turn it into waxes, we could turn it into into this, into that. He's like, "I created a grilled cheese sandwich that was zero calorie that tasted delicious using Volvo." And we're like, "Dude, that sounds kind of insane." And like, he's like, we're like, "Why didn't you do this crazy idea? You sounded pretty passionate. You went pretty far." He's like, "Well, there just simply wasn't gonna be enough oil supply to do it." And he's like, "We would've had to take the oil out of the sewage system and centrifuge it to recycle it." He's like, "And I realized, you know, even I couldn't do that." And I was like, wow, this guy's like, you know, half genius, uh, half crazy. And I, you know, I don't even know where the line is, but I find it fascinating that he, A, thinks like this, and B, doesn't just think about it, you know, literally is like, yeah, in my house we converted the dining room into like this lab in order to like do these, you know, these sorts of projects. And like, you know, out of one of them came Anduril, the $8 billion company, and the other one was going to be this crazy like, you know, oil-based fake food.

That's crazy. That is awesome.

I love—

yeah, see, that's the type of entrepreneurship that I'm, I'm really drawn to, is just like people that are hacking on stuff, um, at night. You know, for me, uh, a lot of the stuff that, that I think about in that, that vein, I tend to outsource and get other people to, to work on it. Um, a lot of the stuff around, um, longevity I've been interested in, specifically, uh, a drug, uh, called rapamycin, where it's been proven now to extend life in, in various animals and now applied to dogs. So myself and, um, Jack Dorsey and Brian from Coinbase and a few others all have been putting money into funding studies out of the University of Washington, um, to, to really prove this out in dogs and canines and then eventually move it into human trials. So, you know, some of that stuff and the biohacking stuff, I, I still put a lot of effort and time and attention in, and I, I try this stuff out on myself as well. You know, I'm I'm trying some of these experimental things. Not because I'm not one of these people that wants to put, you know, young people's blood in them and live forever. I want to die. I just, you know, I do like the idea of—

Not yet.

Since I am an older dad, I didn't have my first kid until I was 40. I would like to be around a little bit longer for them.

That's all. I've heard of people doing this. I know Tim's doing this with the, what's it called? Psilocybin mushrooms. Psilocybin. Yeah. And, uh, how much does it cost to fund a study and what do you get out of it other than like the altruistic of like, well, we're just contributing to like the grand thing, but is there, is there like a direct outcome that you can get from it? Like we can use this to fund a company?

No, no, not, not in this particular case. Yeah. Tim was also, uh, put some money into this one as well. And there, there was, there's nothing you get out of it other than just trying to help further science. You know, a lot of these, um, in this particular case, the study was funded But be, depending on the sample size and how many canines you have involved, you can only detect certain levels of output. You need a larger sample base. It is called like a properly powered study in order to detect smaller little nuances in the data. And so we wanted to make sure it was powered enough to detect, I believe, up to 10% lifespan increase. And so to power it was to add another million dollars or so into the study to make sure that they could bring on the additional canines required to make that happen. And, you know, I put my dog on it as well, and he's 12 now and he still runs around like a pup. And I attribute some of that to a cycle of this that he did. But yeah, it's nothing other than just like you, You're figuring out ways in which you can, like, there's, there's all these different avenues on the philanthropic side where you're like, what, what is meaningful to me personally? And, um, uh, this, this, this particular study, you know, I think even if it just worked for dogs would be fantastic. Like, forget humans. If, if I could have my dog live for an additional 5 years, like, what a win, you know? So that it was kind of a win-win study, dude.

I, I talked to this guy that was like building, I think it was called Is it called AgelessRx? I forget his, the name of his company, but he was, he's trying to like, you know, do longevity stuff, uh, supplements and shit like that. And, uh, things are going well for him, but I would, he was kind of explaining his reasoning. He was like, you know, a lot of people are afraid to take these medicines, but we've been thinking if we told them it's good for their dog, they actually will give it to their dog. And he was, he was kind of like hypothesizing to me and like brainstorming with me in real time. He was like, maybe we should just like do this for dogs and just give it to dogs. And if once people see that it makes their dog live longer, then they'll be like, yeah, yeah, you know, fuck it, give me that pill, I'll take that thing. Uh, because there's, there's so much easier to convince to give it to their dog.

I'm with Kevin.

Oh, for sure. Dogs live forever.

Well, genome-wise, there's so much more overlap and, and, and, and connection there between canines and humans than there is a lot of other animals out there. So Um, but you know, the, back to your question though about, um, you know, outta curiosity, what, what would I go pursue right now in terms of startups that I'm not doing? Um, I believe, and it's very, very clear now that AI in the next 5 years is gonna change everything. Um, we're seeing OpenAI and a lot of the projects they put out there recently, um, whether it be creative writing or I believe Fiverr as a company, it will just be nonexistent. It's gonna destroy the low end of the creative market initially and then work its way up the chain. And you know, just the outputs that you're getting now from prompt-based art, you know, the future versions of Photoshop are not gonna be about moving mouse and pixels around. It's just gonna be telling the computer what to do on your behalf. You know, you'll highlight an area and say, you know, change this aspect and it'll all be done via prompt and meaning you type in what you wanna see change and the AI will just make it happen. And we're seeing that today. And I'm seeing, you know, advancements on the AI side in medicine, obviously all the creative side. There's probably a half dozen or so tools now that will complete, you know, write complete paragraphs for you. If you're writing sci-fi, you give it some initial kind of prompts of where you want the story to go. And the writing is quite good. I have no doubt in the next 5 years we'll see a New York Times bestseller that was 90% written by AI. So it's, it's, I, I, there's just so much interest and with the interest and excitement flows the engineering talent. So I've seen a lot of, um, friends that are these, you know, a lot of people I worked with at Google and, and other places where, you know, they're, they're very insanely amazing engineers, you know, previously working on distributed systems and some of these hard problems that they were trying to solve. And now said, hey, I'm actually going to pivot into this new world of AI. And anytime you watch that kind of flow of high-quality engineering talent and go move into something, you pay attention. So I'm looking at a lot of investments in that particular sector and I'm very bullish on it and something I don't have time to work on, but I believe some great businesses are going to be built there.

What would be an application you would want to do in that space? So all those kind of like threads where it's like, creative work, medicine, you know, writing an AI book. Is there an application that you can think of that you're like, I feel like AI could solve this? Because I think that's— it's a hammer in search of nails at this point. That's when I talk to you—

you made a joke. You made a joke. I always tease Sean about Web3 because I'm not the biggest fan of it. And he was— and we were joking about how he was like coming up with ideas with AI. He's like, finally, a use case. We found it. And like with AI, it seems like there's actually way more obvious use cases, right? But, uh, yeah, what, what application excites you?

Oh, I'd love to have that Web3 debate at some point too. But, um, on, on the AI side, you know, it, we're already seeing this, right? So, so Figma was purchased by Adobe. You probably all saw that. It was crazy acquisition. Um, you know, probably the, the, the, the, the standard these days for prototyping and, and creating, um, interfaces for everything from mobile apps to websites to, to you name it. Um, we're seeing, uh, already built-in plugins to Figma, um, that allow you to prompt-based build, uh, anything in, in just a matter of seconds. So you can say, hey, give me an interface for a mobile app that has these 5 options, uh, in this color with this futuristic type style. And you know, you get something back in real time in, in, in, in 25 seconds. And it's, it's rough, but it's giving my design team and other designers out there just a great starting point and it saves them a ton of time and effort. But this is like inning 1, like 2, 3 years from now it'll be doing 90% of the work versus, you know, the first right now was probably 20% of the work. So, um, that is, is, is super exciting. And the assistance and, and time to market for new ideas, new projects, I think is gonna be compressed even further. It's, it's the same thing that we, what happened with the kind of like late Web2 when we went from racking our own servers to fully deployed and automated and managed, you know, AWS instances that, and some of these databases that just auto-scaled as you threw traffic at it, it really compressed the time to the go-to-market time, you know, by quite a bit. And I think we'll see the same thing on the design side. So the speed at which we can develop and deploy new ideas is just gonna be, you know, probably an order of, order of magnitude better than it is today. Um, so I'm excited for that.

Where do you, uh, a question that we started asking people and it's actually, uh, I've always learned so much from this, but what message boards or Facebook groups or websites, uh, what corners of the web are you lurking in right now? Like for me, I love Facebook groups. There's always like a weird Facebook group, like a tiny example is overlanding. You guys know what overlanding is? It's like, no, It's like, um, I don't know the exact definition, but it's like, you know how you see like Toyota 4Runners or F-150s that have like campers on it and it looks like they can go in the desert for like 2 weeks. So I started like joining overlanding groups like 3 years ago, cuz I was like, oh, this is kind of an interesting trend that's picking up. Or another one that we got really into a couple years ago was mobility. So like all these grown men not caring about yoga, but they called it mobility and it was all about like stretching. And it's like, what's going on with— there's like all these weird Instagram guys like doing all this stretching shit. It's kind of intriguing.

And like a lot of times it's like instead of, instead of therapy, executive coaching, you know? Yeah, that's what happened from, from yoga to mobility.

Yeah, they just changed like mayo and aioli and it totally worked. It's awesome. Like, I love mobility now. And like, for, for the body stuff, Tim Ferriss was always pretty good at that. Like, he'd be talking about all this weird stuff like fasting. It's like, dude, what the hell is this fasting thing. What are you talking about? Uh, and, uh, that was like a really cool corner of the web to like look in on and like see like how are the geeks behaving now so I can learn like how the rest of the normal, like average Joe is going to care about in the next 5 or 10 years.

Yeah. Where there's that Chris Dixon quote. Are you familiar with it? Yeah.

What does he say?

It says what the geeks who are playing with on the weekends will become like what we're all using like several years later. It's something, some version of that.

Yeah. So like what geeky places are you hanging out right now for, for, for Sean and I, it's like a lot of Twitter people. So we'll find like specific people quirky and we're like, what the hell is this guy talking? He's talking crazy. I mean, it's really cool.

Yeah. I mean, I follow a ton of people in crypto Twitter, so I pay attention to all the, you know, the what's happening on Web3 via, via, um, Twitter. And then also, you know, mostly Discord. It's just a lot of private Discords. It's a lot of private Telegrams, small groups and gatherings of peers that get together, discuss new ideas, new projects. Um, these DAOs, uh, these decentralized autonomous organizations where people get together to discuss and collect and purchase things. Um, so it's a lot of— I've never spent so much time in Discord. It's like, it's crazy that the conversation has shifted there and Twitter largely.

Um, dude, I hate that, by the way. I love the fact that like a DIG or Reddit or something exists where you can just like, if you Googled it and found it, like you could participate. Now I'm like, oh, what the fuck, man? Kevin's probably got this crazy ass Telegram group that like there's, I don't even. I can't get in cuz I don't even know exists.

No, you can join Proof. It's $50,000 and you're in, bro. It's easy.

No, it's, I, I think it's more like it's people realize that, um, they wanted a little bit more intimate conversation. So I, I have a feeling that like there was a, there was a lot of, of this move to do smaller private Discords and smaller Telegram groups because it would lead to just not the masses flooding in and the chaos that you would see on Reddit. And so I, that's kind of been the move that I've seen and the reason behind a lot of that. But it's not hard to get into there. You just have to actually show them that you, you know what you're doing. Like you have to, you know, get in there and embrace Web3, which it sounds like, Sam, you may not be the biggest fan of, but you have to, you have to get in there and, and, and, and talk the talk and know where to go and people will tell you like, this is the place to be hanging out, or I'm enjoying this Discord over here. And you'll learn about this and this is where the AI Discords are or whatever it may be. And, um, that's just kind of the new, it's the new Facebook. Facebook's, uh, it's, it's, it's, I'm sure it's good for some things, but it's, it's, it's dead when it comes to Web3.

You want me to tell you my, why I'm not a fan of this?

And yes, please.

I'm going to get you, I'm going to try and get you fired up here and then we'll talk about, let's try to talk about Proof. I do. It sounds like I'm making an easy out, which I kind of am, but basically, like, I am— I'm decently educated just by hanging out with Sean. And so I have to admit that, like, some of my beliefs are a little bit loosely held and I'm not the most educated on the topic, but my opinion on Web3 is basically it's a bunch of like— it's just this kind of circular economy of a bunch of people making, making products to serve an industry that has yet to, like, truly figure out— or I don't know what you call an industry, a movement. That has yet to truly figure out like what the, what the thing is that they're doing. And there's so many examples where people I think are fairly like egotistical and elitist about it, saying like Web 2.0 is old and like the way that this has to be decentralized or this has to be this way. It's like, man, just because you're putting Web3 in front of something, that doesn't mean that there's actually a problem here. And I think you're just wasting so much time and energy working on something that is just like a circle jerk that doesn't actually solve a problem better than the Web 2.0 version. Also, I thought it's pretty dogmatic where it's like, decentralize everything. It's like, dude, I want some stuff centralized. Like, can you imagine like calling customer service on a decentralized— like, it's like, no, I like— there are some things that I want like to have a— to be centralized. And I thought that they were a little bit too dogmatic. And I thought that they were oftentimes— I'm saying like they, like you people, uh, like you guys like didn't always have wonderful solutions. You were just making shit up in order to like get in the game. And I just thought that it, it kind of bothered me.

Yeah. I mean, I feel your frustration there in that I too am someone that, um, when I look at what's being built in Web3, if it's, it's just for the sake of calling something decentralized and there's nothing behind it or no structural advantage for that being the case. Um, I think it's, it's, it's, it's silly, you know, it's like, I'll give you a great example. Um, we're, we're working on, um, there's a lot of things that you want to do in Web3. Some of them are high value and some of them are low value when you were talking about working with the community. So we have a community of people that come together to do all different types of things. And some of it is what we call token-gated content. So it's like a membership model where you have to be a member of something or hold a certain NFT in order to unlock. Certain access to videos or content or whatever it may be. Some of those things can be high-value items where you receive an NFT or something that is actually has some financial, like, you know, something behind it. That is a case where you want to actually have that hardware wallet and pull it out and, and do it in a way that is secure and that is protected. And, but the rest of the time you don't need that. You can use a Google login. It's okay to use a Web2 login. It's okay to use your email. Password with two-factor authentication. Like, we don't have to throw away a lot of the fantastic technology that's been built in Web2. There's other things like, for example, some decentralized maximalists, and I think maximalists is really what we're talking about here because anyone that is a maximalist, uh, on—

Maximalist means what? You just like extreme?

It just means that you are so into something that you can't see any other way. And it's like, it's your way or there, there's no possible— there are people out there that say there is no other cryptocurrency than Bitcoin. That's the only one.

Isn't it? Pomp, our, our buddy, isn't Pomp like, don't they call him online? Like a Bitcoin maxi?

He, I don't think he, I think he is a maxi on Bitcoin. And, and you know, Dorsey's in that camp too, where he's like trying to extend Bitcoin and says that's, that's kind of the only currency. And I, I think this applies to so many different things. Like, I don't want to get into political talk, but anytime you get to the fringes of anything where it's like, this is the only thing that matters, you get into crazy town in my point of view. And so, you know, I think that is a danger of Web3 where there's a lot of that kind of idea that if, if it's not pure Web3, it's not right. And I'm with you. I 100% agree. But that said, like, I've seen this idea and a lot of the DeFi tooling, when I say DeFi, I mean decentralized finance. A lot of the DeFi tooling that's being built on the blockchain, uh, in a performant way, in a cost-effective way, in a way that when you think about Wells Fargo as an organization with, you know, 150,000 employees, I'm just making that up by maybe it's 50,000 or 75,000, somewhere in between that, that range where that is just a lot of bloat. And it, and because of that bloat and because of that insane monthly nut that that company has to cover. Um, you know, th— those dollars are, are not, not flowing to the right people. And so there are examples of more efficient ways of doing finance on the blockchain that, that can be done in a trustless way, written into smart contract code that will mean for better outcomes for the consumer. Now those can be paired with centralized solutions, right? Like Coinbase is a centralized organization. You have an email address that you can send it if something goes wrong with your crypto account, but they hold and keep decentralized currency, right? And they, and they do things like decentralized staking where you earn 4% on your Ethereum, but they're a centralized company that gives you that customer support. So I'm not, I'm, I'm a fa— I think that the, the ones that really win here, yes, there are going to be the people that say self-custody is the only way. They, there's this famous saying that. If it's not your keys, it's not your crypto. Like, like you have to hold your own private keys. I'm not in that camp. I do that personally and use safety deposit box and a whole slew of things to safeguard that for some things. But there's other solutions where, where a hybrid approach makes more sense. So know that your argument is completely valid and that a lot of entrepreneurs that are building a Web3 completely agree with you and that let's not throw away the baby with the bathwater here. There's a lot of great things. But there are also some great advantages that come with being, uh, decentralized or a whole slew of other technologies that's being built on Web3, um, that, that I could point to that you'd say like, oh, that, yeah, that actually, that, that does make more sense than the old way of doing things.

So, so let's, let's do this real quick. So you've probably seen just like anybody else, these like, um, there's like these permanent, uh, like just like there's perma bulls for crypto, there's perma bears and they're mission in life is to basically find every stupid use case of crypto and highlight it, or every bad investment, or every clip of a, a pro— you know, some dude at A16Z who goes on a podcast and says something dumb about crypto when asked about a use case.

Um, are you talking about me? Because I was just on their podcast 2 weeks ago. No, no, they—

I haven't seen it.

But Dixon—

but like, you know, there's, there's people that sort of are, are focused on, on poking holes. And I think there's some value in poking holes, but there's also, you know, it's a little embarrassing to spend your whole day poking holes in something, you know. But let's put it this way. I'm on this podcast, I'm the crypto believer. I'm the one who puts a significant portion of my net worth. I have a crypto media company. I have a bunch of belief in crypto. But for this use case, for this exercise here, I'm going to point out two things that I think would be, would be, you know, strong and valid points against crypto to somebody like you who is also a crypto believer. So I want you to kind of argue against these. And I hope that this doesn't get clipped as, like, you know, Famous Investor X Fumbles the Ball, uh, when trying to explain, you know, crypto things. So let's try to do better than that.

Yeah, let's do it.

Okay. So the first would be around, uh, NFTs, right? So you're a big NFT guy and there's NFT art, which I think pretty hard to argue against at this point, like digital art, cool. Their ability to own digital art. That's one use case for NFTs. But a lot of people who believe in NFTs will also say, but that's just the beginning. NFTs is a, is a file format. It's a protocol. There's all these different use cases. For NFTs. And, um, I saw the founder of OpenSea, I think, uh, talking about this yesterday on a podcast where he's like, they're like, why? He's, you know, he's like, oh, another use case is NFT tickets. And they're like, so why would there— why would you want to have an NFT ticket? He's like, well, because then you— it's, you know, you could plug it into DeFi and you could take a loan against your ticket. And then people were like, why the fuck would I want to take a loan against my $60, like, concert ticket, like, is that really what the hype is about? And it's sort of a silly use case. So I would like you to give me the non-silly NFT use cases that you're excited about.

So like, yeah.

And the, well, let's, let's take an example.

Let's take the ticket example. And the art one is easy. It's a new canvas. Let's actually, let's cover that first. The art one is easy. It's a new canvas. You can do things and pull from, uh, real-time data to display art in very unique, fun, creative ways. Right?

Like it's really not that much different than your, than Rolex. I mean, like, there's no reason why a Rolex is $150,000 other than like a lot of people think it's cool.

Yeah. Well, I would say there's a difference there because something you may not know about Rolex is they make over a million Rolexes per year. And so Rolex hides that number. And the reason they hide that number is because if they didn't have a sense of scarcity around it, and they, they do this specifically when you go in their stores, there'll always be a— next time you walk by an actual true Rolex boutique, Notice how there's like some missing spots and when you go inside and that's all play. It's play because they're like, oh, they're sold out. They're not available, but we can put you on this list. And in 3 to 4 months, we might, you might get a phone call. Guess what? You always get the phone call and the watch is coming because there's, they're making a million a year. The nice thing about, you know, the, one of the things that I was always so confused by is I was a comic book collector way back in the day. And I bought Wolverine #1 because I love Wolverine. It was like my childhood, like I always wanted to own one, right? And so I bought Wolverine #1 and it always hovered around $50. And I was like, why is this not going up? It's the very first Wolverine launched in the '80s, right? It wasn't the first appearance of Wolverine, but it was the first Wolverine comic. And I finally got a hold of a really well-known collector and he goes, oh, he goes, you don't know. They knew by that point that Wolverine was a hot character. And so they printed over 300,000 copies of that first edition. I was like, oh shit. Like that's why there's just a flood of these in the market. So, you know, NFTs, the beautiful thing about this, when you have an artist produce a piece, it has proven provenance. So, you know, where it's come from, it has proven scarcity. So you can't like create, you know, additional add-ons or duplicates because it's all recorded on the blockchain. And then you have the unique ability to do very creative things like animation, uh, oracles where the art can change based on the stock market price or time of day. Or phase of the moon, and there's just so much more extension. It's a new vertical for art. Fine. That's great. Awesome. Like digital frames are going to be getting better. It is going to be a thing. Like there's no, in my mind, there is no argument to be had there that this won't be— I don't bet against the future or the inevitable, and art is the easy use case for NFTs. The ticket thing is different, right? So the ticket thing, I, I'm with you. Like I understand that people are, in, in Web3 are trying to like create these fancy financial instruments to like leverage you on anything that you own. They're like, hey, you have a ticket to that upcoming concert that's sold out, you know, spin it into this DeFi unit and take a loan against it. And then you can buy it back and use the money in the short term. And it's like, that's all bullshit, man. That nobody's going to do that. Right. It's, it's, it's don't get me wrong. There's, there's, there's, there are specific use cases where that does make sense. Like loan against NFTs is going to be the same thing. That happens when Christie's gives you a loan against your Picasso, right? Like these, these happen, this happens all the time. It's just a parallel for the digital world. There are certain types of, of assets, digital assets that getting loans against them, if it's something you want, will make sense. The tickets thing for me is very confusing, but what I will tell you is interesting. And I've talked to actual rock stars about this. Like I had Mike Shinoda from Linkin Park on my show and he's a huge NFT fan and he creates them.

Um, you know, awesome flex, by the way. You know, I've talked to some rock stars about this. I'm going to—

that's cool.

I'm not making fun of you. I'm saying that's cool. I think it's cool.

I think it's important because like, you, you want to get the artist to buy in on this totally too, because they're saying it's cool.

Yeah.

Yeah. He's a, he's an awesome guy. Very approachable. Very approachable in the terms of rock star guys. But Shinoda will tell you that like, well, what we talked about, which is an obvious one, is like, Okay. Imagine the tickets. Well, let me step back. One thing I believe to be true, 90+% of people that interact with NFTs over the long term, I believe won't even know it as they're doing it as an NFT. It'll just be something where they have a digital wallet, an app or something like that. And they have a ticket there, right? They're not going to know that behind the scenes that is powered by the blockchain and recorded by the blockchain. Right. So. I think what's going to happen is the nice thing about the blockchain is because it is a ledger, an immutable ledger, that is a way to say and prove that you have done something, that you either attended an event or you've actually physically done something. There's a ton of possibilities that I can unlock, right? If I go and I see Mike Shinoda play 5 shows or 10 shows, maybe he says, okay, now according to the blockchain in our app, and again, the consumer doesn't need to know about this. Anyone that's attended 10 of my shows gets a VIP meet and greet before the show. Right. And there's a thousand different things that you can do that you want to have that security of the blockchain behind the scenes. So it's not being forged. So there's not being copies of it being made. So there's not like a way to fake it. And that's the nice thing about the blockchain is it provides you a way to have the security and knowledge that something is not being faked. And you can imagine that's broadly applicable to a whole slew of different industries. Um, I don't think we'll be calling them quote unquote NFTs, you know, it's just going to be a great piece of tech. It's just another database. That's all it is. It's, it's a distributed, um, immutable database that is decentralized. It's, that's all this is, which unlocks a bunch of fun new use cases.

Let's caveat it. All right. So let's say, cause I think I get it when I get what you're saying, but I also get the, uh, the eye rolls that people get when it's like, like, cool, tell me like how this is gonna make my life better. And it's like, well, the cool thing about a blockchain is that it's provable scarce. It's like, it's like, wait, you're telling me about the under the hood part? Whereas for example, if my mom is like, if I'm like, mom, you should set up an email address. And she's like, what the heck is email? I don't need that. And it's like, well, no, check this out. Like, you know, you send letters or you, you know, you send letters to your sister who lives across the country. Like, watch this. If you do it this way, it's free and it'll be instant. And like, oh wow, that's cool. And hey, you know what's even better? Because it's all digital, you can just type the word and it'll find that file. You don't have to keep it organized somewhere in a folder in your house.

Yeah.

Uh, right.

So I can, I don't have to tell her how it works at all. I can literally just say it made your life better by being, by giving you, you know, more time, more money, more whatever. And so I think the question is, what does NFTs give? What, what does, what will an NFT give a person that makes their life better without explaining how, how the tech works at all?

Sure. Oh, I'll give you, I'll give you a great example of one that hasn't launched yet, but something that, that I'm personally working on. So I'm working with, um, a well-known, like, very culty kind of wine producer out there. And, um, you know, wine at the highest level, at the high end, it's a tricky, it's a tricky business because there's, you know, forgeries, there's fake labels, there's, they're putting holograms on the side of them, they're putting, um, uh, chips inside of the labels so that they can be scanned to prove that they're authentic. Right. That's one piece. So the first question is, if I'm buying off the secondary market and not directly from the producer, am I getting something that's legit? Excuse me. The second piece of that is once I receive that bottle, how do I store it to ensure that if I'm going to keep something and I want this asset to appreciate over time and I want to drink it a decade from now or two, then how do I ensure that it is being stored the right way? So one thing that is happening in the next 4 months will be the issuance of NFTs to people. That is going to be from a major well-known winery where it will represent one physical bottle of wine. There's a couple advantages here. One, you don't have to take possession of it right away. You can let it sit in its proven perfect storage conditions and age for decades to come. You can let it appreciate in that, in those storage conditions, and you can hold onto the proven ownership of it as an NFT. Let's say that bottle of wine. 4 or 5 Xs over the next decade. You don't ever have to then pull the wine in out of the cellar, take ownership of it, find a third party to sell it, and then resell it where that person is questioning the authenticity of that wine. Instead, you can just transfer that NFT to a buddy. You can gift it to them for a special occasion or an anniversary. And then when they decided, hey, I want to drink this, they press two buttons and that bottle of wine that has been stored perfectly for a decade shows up at their door. That is efficiency. That eliminates fraud. There is just so much to love in that equation. And that'll be applied to the watch industry, to the luxury world, to all these different verticals. And it just makes sense. Like, what about that? I'm just curious if, as you hear me explain it, doesn't sound like a better world, like in, in terms of fixing a bunch of problems.

I think, uh, if I was gonna, if I was gonna argue against that, like, just to steelman the argument against it. I think it would be cool, uh, like, maybe it's gonna— maybe these are certificates for collectibles. Most, you know, it's not gonna— that doesn't impact most people's lives because most people are not collecting high-end bags or wines or this— where there's huge problems of forgery like that. Uh, that may be one thing, which is it's not going to impact that many people, um, in that sense. Oh, you're telling me NFTs are this game-changing, world-changing technology, but that's a really niche specific, you know, 1%er type problem. And then the other is like, you know, um, sounds like an NFT is like a digital certificate. Um, you know, you could have done that with another type of certificate, but, um, or another type of database maybe. And, but maybe this is better. Uh, like, I do agree it's better, but like, it was possible before. It didn't take the impossible and make it possible. It made the, uh, the possible— made it maybe made it more efficient or a little bit more convenient for the consumer. And so I think that would be maybe one argument against it, but I don't want to go too far in the weeds.

Yeah. I, I, the other thing that I think that to add onto that though, is that because you have, well, I'll give you an example, like back in, in, and you know, the back to the Rockstar example of, of a, an artist. Um, you're reliant upon, if you did want to do some type of rewards program or something for, well, actually let me step up one more point. The point you made about the 1% problem and is this applicable to those people? You're absolutely right. Like, there's only a certain number of people that are going to collect art at the highest level and wine at the highest level and all of that. I mean, granted, these are double-digit billions of dollars a year, like, big markets to go after. But you're right, these specific use cases that I'm giving are, are very niche, right? Um, I think on the more broadly, uh, on, on the, on the idea of just membership and access and prove where you've been, what you've done to unlock loyalty and rewards over the long term. And think about, you know, replacing the Amex points or, you know, other point type systems or reward systems with blockchain, the beautiful thing about it being decentralized, and this is one argument for decentralization, is that it's forever on the chain and you're not dependent upon a company being around for that, for that to exist. So if an artist is engaged with a startup that is working on a loyalty rewards program for them and they run out of capital and die 3 years later, As long as they stored their information on the blockchain, that artist can then just pick up where they left off and it just, it continues forward. And we've already seen this happen where there's been several startups that have stored their information on the blockchain where they go out of business because they just, their, their idea didn't hit. And then someone fills the void and comes and says, I have a better take on this. And now let me tap into that public data and use it going forward so that not all is lost, which is kind of a new concept in rather than just a database going away. It's always gonna be there and can be reused, which I think is pretty, pretty compelling.

The really simple 2-second example of this is you play a game, you go, you, you get really into Fortnite, you go buy a bunch of skins, you, you dress up your character, you got the cool, you know, like glider and you, you bought all that stuff. And you know, a year and a half goes by, your friends have moved on, they're all playing Call of Duty now. Um, you've sank $350 into Fortnite. You don't own those items. You can't resell those items. Right. You can't recoup any of that value, nor could you take those items into any other game. So in a Web3 world, either another game could come out that says, hey, we accept item— we, we plugged into this protocol, so you can bring your cool sword from game 1 to game 2. That makes the sword more valuable because now it can be used in multiple games.

So maybe we're seeing this already, the interoperability between multiple Web3 platforms saying that this is a defined standard, and now these can digitally move between platforms. It makes a ton of sense.

Now those items are more valuable because they can be used in more places. And the other one is that if I'm just done with the game, I could just dump it on to the next person who's really interested in Fortnite, and I can recoup some of my investment, which will make more people want to spend in games because it's not just a money pit, it's an asset that they can resell. All right, so that's like the quicker example.

Maybe I love that you joined my side.

You were, you were definitely on your side, but I have to argue the other way, uh, in order for this to be interesting. Let me, let me give you a second. At the end, at the end, you're like, I get it.

I'm in.

The other crypto nerd argument would be, okay, for years people have been saying that Bitcoin is this, this inflation hedge or this currency that, that's, that's, um, that doesn't inflate. And oh my God, you know, how lucky for you guys. The US government starts printing trillions of dollars. Inflation is at record highs. It's in the news every day. Wait, what happened to that awesome inflation hedge asset? Why is it down 50% when inflation is Is, is the bigger problem than ever. Shouldn't this be, shouldn't this be your time to shine Bitcoin? So what say you to that?

Yeah. I mean, it's, it's a real shame that, that Bitcoin has been so spiky because if it had, it been this linear growth to $20,000 to where it is today, we'd all be like, this is the most amazing thing ever. Like, like if you just take the spikes out and make it look linear, it's, it still looks like an incredible asset. Like, you know, just go back 5 years, look where it is now versus 5 years ago. So. It's the spiky nature of it that hurts it in the end. I would say that I'm a fan. I think Bitcoin is a tough one because I don't like that it's not a green currency and I don't see a clear path that ever being the case. And I know everyone's trying to extend it in new and exciting ways and try to make it more Ethereum-like and so that it can do more than just be this type of digital gold. For me, when I think about those types of assets, I'm responsible in that I'm not betting the farm on this, but is it a small percentage of my portfolio? Absolutely. And I just consider it another asset class that provides me a little bit of diversification across the board. So the majority of my personal holdings is still standard, you know, index funds, uh, that, that are pretty vanilla, low-cost index funds, you know, the Vanguard way, right?

Yeah. I was actually going to ask that. What, what is your liquid portfolio look like? Like where I was, I was been waiting to ask you that.

Sam is like, uh, ETF, low-cost ETFs and bonds.

Dude, I'm 80% Vanguard index funds, 20% bonds. That's all. And then I build private businesses.

Yeah.

Sean, like has put everything into I'm like angel investing, crypto, and then like, you know, 5 companies I believe in and, you know, a little bit of index funds. Like it's like, yeah, zero, like it's like 5% or something like that. I keep 10% in cash or something. And so what would your, what would your pie chart look like? And obviously it changes over time.

Yeah. So, so my pie chart would be essentially this, um, you know, 80%. Well, I think there's an important thing to caveat here is that as a venture capital, uh, partner over True Ventures, I have a lot of risk on the table there in venture early-stage investments.

Did you have to put your own money into that or is that just your carry?

I do. Yeah. I had to put my own money into it as an investing partner. You also invest alongside the fund. So, um, that is my bucket of risk, right? So just setting that aside and saying, okay, you know, I have carry in the fund. That's my bucket of high risk.

Too much capital, right? You put like, I don't know what, like quarter million dollars or a million dollars, something like that into that.

It depends on the size of the fund. It's, it's a, it's a, it's a percentage of the fund. We just closed our latest fund, which is $750 million. And so the partners put in a percent of, of that, um, in back into the fund. Uh, I'd have to look at what the exact numbers are, but it's substantial. They want you to have skin in the game when you're investing. Um, so, you know, I consider that to be like, those are, those are the big high-risk buckets. So everything else I do, I want to be just super vanilla. And it's, it's that, it's that Vanguard index fund. Um, keep it, you know, keep it really simple. I don't do bond funds. I'd rather rely on people to buy bonds on my behalf. Um, you know, I am laddering into, uh, uh, bills right now because you're getting 4+ percent in the short term. And so, you know, just, just ladder into, to, to those makes a ton of sense right now. Um, Anyone out there that has $10,000 that's sitting around that doesn't go buy an IBILL right now that's earning over 9% is just insane. That's the most no-brainer scenario for someone that's listening to this podcast. By the way, there's like one week left of that, right? Yeah, that's right. Obviously not investment advice, but you are getting the full faith of the US government as the backer and it's over 9% and you can do $10,000 for yourself and $10,000 for your spouse, which is amazing. So, um, anyway, it's, I keep it really simple and then, and then the rest is, is, is the crypto, the crypto side of things is like, you know, let's call it, uh, 50% NFTs and 50%, uh, digital assets. And that's, you know, probably 10% of my overall. Okay.

So, so 90% of non-venture stuff is in just An index fund.

Yeah, yeah. And multiple index funds that cover a variety of markets. But yeah, low cost.

Do you touch real estate at all or no?

Not really, other than just, you know, my own stuff.

Do you own or rent?

I own.

Uh, we're— we've always had this debate, and I know you got to go in a minute. I hear your alarm's going off, but we always have this debate. Well, we both agree. I, I own. I wish I would have rented, dude. I just want to rent everything. I don't want to own a lot of stuff. Do you regret owning or do you like being an owner?

The thing is, when interest rates were low, you can just take a bunch of capital back out of your house and pour it back into the market, assuming that you're going to beat that. If you could own a house, take a loan out against that house and get a couple of points and earn 5 to 7 in the market, I'll take that delta all day long. So, um, that's kind of the way I play it.

Cool. Well, dude, you're, uh, I'm really happy we got to talk. I, um, I used to work out of the Reddit building at, uh, Third and Bryant, and I remember seeing you walk by and I was like, oh shit, that's Kevin. I wish I would've said hey. That was in 2012, so it's only been 11 years later, 10 years later. But, uh, I'm happy that we are able to talk. Um, I've been a big fan of yours. I know Sean has as well. So it's really, uh, exciting to, to be able to meet you.

I, well, I love that you guys are doing this show. I mean, it reminds me a lot of like the, the kind of fun little hash out debates that Tim Ferriss and I have when we do our random shows. Like they're just fun, right? You get a couple of friends together and shoot the shit and some, some crazy discussions come out of it. So that's, that's great, dude.

Those were— I can't believe how big those were back then. I remember the Kevin and Tim shows, I think they call that. He like had a funny name for you, like Tim Tim Top Top.

Yeah. Oh, I call him Tim Tim still. And he calls me Kev Kev. But yeah, we just shot one here in person maybe 2 weeks ago, which was fun. It was good to see Tim again. I hadn't seen him in a minute.

But there's so many little things. Like, I remember you talked about Wim Hof back then, and I was like, you know, next day I'm on my floor, like, breathing, breathing hyperventilating on purpose.

I even remember your wife, Dr. Dara. Is that her name?

Darya?

Yeah, Darya. Like, it's funny. It's like that stuff was so— I mean, it still is, but it was like particularly when I was 22 and just getting into Silicon Valley, like, I really looked up to you guys as like just Show me how to Silicon Valley, you know what I mean? And it was really cool.

Yeah, that was, that was a fun, I was, I, I miss not living in the same city as, as Tim cuz we, we, we always have get into some trouble when we're together.

So yeah, you guys provide a blueprint for us in, in terms of like, hey, if you could find somebody you got chemistry with and you shoot the shit and like, what's your content? Your content is just, yo, I'm super curious and interested in a bunch of things and this becomes my outlet to summarize, you know, my set of experiments and rabbit holes I've been going down. And like, you know, we would have never done a podcast off like, oh, the ad revenue will be enough. It's like, no, it's not really like— fuck that, it's not really relevant. Um, and seeing, you know, Tim and you and how, oh, actually it's these relationships and these investments and there's these little side projects you kick up and actually you can make this whole thing work without having to go, you know, do this like, you know, traditional kind of venture path of, uh, yeah, of raising money to go do this thing. So that was pretty inspiring. So, you know, thank you for that. I think, you know, just seeing a blueprint is like that Roger Bannister 4-minute mile where you're like, oh, I can have the lifestyle I want, but on my terms. And if these guys can do it, then we can do it.

Oh, I mean, it's, it's congrats to you both. It seems like from, from what I heard here at the beginning of this episode, you guys have done quite well. And, and, uh, congrats on your success. It's awesome.

Congrats to you too. And thanks for kind of paving the way. We appreciate it. And thanks for coming.

Thanks for having me.