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My First MillionKevin Rose: His $100M/Year Watch Blog, Money From Digg.com, & Web3 Business (#382)
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EVERY SPOKEN WORD
95 min read · 19,154 words- 0:00 – 2:15
Intro
- SPSam Parr
When I saw you went and did the watch site, uh, uh, Hodinkee, uh, first of all, Shaan, have you ever read that? Like, when I, when I s- 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?"
- SPShaan Puri
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?
- KRKevin Rose
Yeah, yeah, we're over 100 million in revenue now.
- SPSam Parr
Man, that is wild.
- SPShaan Puri
That's insane. [upbeat music] What's up? All right, in this episode we are sitting down with Kevin Rose. Uh, 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 a, 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 listen to it, you're gonna see very chill guy, very, um, down to earth, very humble, and, um, 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 dif- people who play the game with different, in different ways, and he's definitely somebody who's interesting. We talked about, um, a bunch of his projects that you may not know about. So for example, he's creating Watchville, this niche project for watches that grew from one 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, h- how he got into Twitter as a 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, uh, a crypto skeptic. Kevin is obviously a crypto believer and one of the kind of m- most well-known guys in the crypto scene. And, uh, we had a little debate where we talked about is it all bullshit, or are there some use cases? So, uh, hope you enjoy this episode with Kevin Rose. I liked it. I think you will
- 2:15 – 14:06
Kevin's background
- SPShaan Puri
too.
- SPSam Parr
We should give, like, a brief over you- overview, but, like, your resume, we don't really talk too much about, like, resumes and stuff, but your resume's, like, crazy long. So, uh, I've been following you forever, uh, so I've known about your work. So you started Digg, which was... When did you start that in, '04?
- KRKevin Rose
2004, that's right.
- SPSam Parr
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 cover of? Like, you know-
- KRKevin Rose
Uh, Businessweek
- SPSam Parr
... 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. Um, and like, the, it had all this hype, but, like, Digg 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 Digg. You done... Is it, I read it all the time, but is it pr- pronounced Hodinkee? Hodinkee?
- KRKevin Rose
Yeah, Hodinkee. Yeah. That's right.
- SPSam Parr
Hodinkee, uh, a watch blog that also, like, sells watches. You're 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-
- KRKevin Rose
Mm-hmm
- SPSam Parr
... uh, you got the, um, the Oak, uh, uh, meditation app. And then I have a feeling there's, like, five 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. Uh, I mean, does that kinda summarize it?
- KRKevin Rose
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, uh, on the newer side.
- SPShaan Puri
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-
- KRKevin Rose
Mm
- SPShaan Puri
... you know, from, uh, you know, from venture-backed to angel investing to venture investing to-
- KRKevin Rose
Mm
- SPShaan Puri
... kinda like a 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, 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?
- KRKevin Rose
Yeah, there's... I would say that I've always been one, e- ever since I was a little kid, to just tinker and just to, to play. And, and if there's any method to the madness, it is this common thread of e- exploration and just wanting to, if I see something that doesn't exist that should exist, I wanna 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 wanna sit on the sidelines. If there's something that's exciting that needs to be built, I, I'd, I'd rather just spin up a team and, and go after it.
- SPSam Parr
Of all those projects, um, and I'm actually gonna exclude Proof from that because, uh, uh, I wanna 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?
- KRKevin Rose
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, its peak, which was, um, about a 2000- early 2006, um, you know, we were, hit around 38 million people a month using the site. It was, you know, of the Web 2 properties, it was one of the largest. Um, it, it led me to sitting down and, you know, dinners and conversations and hangouts with the You know, Jack Dorsey's and Evan Williams and Zuckerberg's and all of the household names that became these big products, and they were just friends. And so because of that, um, it was more like, "Hey, well, you know, do you wanna invest in my new thing?" And, and so w- I would say the investment side has definitely been the, the best, um, financial returns. I did start a media company, um, that, uh... Well, I would say there's, there's two things that, that... Well, three that are... Two are un- unrealized in Hodinkee, um, which is, is, is gonna be crazy. It'll, you know, it's over 100 million revenue a year now, which is nuts.
- SPSam Parr
Whoa, really?
- KRKevin Rose
Um, and then we have, um, you know, uh, the stuff I'm doing at Proof right now, which has just be- 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, is 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, the, they're much larger on the more angel investment side.
- SPShaan Puri
And maybe that sale gave you the, the ammo to do the angel inve- to do angel investing, or would you have been-
- KRKevin Rose
A bit
- SPShaan Puri
... able to do it without it?
- KRKevin Rose
A bit, but, uh, uh, I was already starting to do small investments, uh, prior to that. So I, I didn't have any money. I didn't come from money. Um, but when Digg really took off, the, the... and we were a couple years in to Digg, 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 know, 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, right?" And so I sold a little bit of my Digg 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're a little bit later stage. And, and so it was, it was those little tiny checks that, you know, d- when they turn into multi-billion dollar businesses, uh, were, were pretty meaningful.
- SPSam Parr
How much does 25K into Twitter and Facebook early on actually turn into? Uh, that, that math-
- KRKevin Rose
Millions of dollars.
- SPSam Parr
Uh, I mean, that, that math is even hard to comprehend. A- and Twitter seed round, what was the valuation then?
- KRKevin Rose
Well, it was difficult because they were a podcast company, uh, doing podcast software, and then they, they did a new round. They, they pivoted into Twitter. And so, oh, gosh, I'm drawing a blank on the name of the podcast. Uh, what was-
- SPSam Parr
Odeo.
- 14:06 – 27:27
Meeting Mark Zuckerberg early in his career
- KRKevin Rose
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, um, wildly creative and, 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, um, y- 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, I'm quite a bit older, [coughs] excuse me, than he is. And, um, just-
- SPSam Parr
How old is he now? He's still only, like, 38?
- KRKevin Rose
He's younger than that.
- SPSam Parr
Oh, my God. [laughs]
- KRKevin Rose
Yeah, so how old is Mark? Let's... Oh, yeah, you're right, he is 38. Yeah, he is 38.
- SPSam Parr
Man, still. That's still... I mean, he's in his 30s. That's pretty wild.
- KRKevin Rose
Yeah. It- 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 wanna say, so he was 21.
- SPSam Parr
Wow.
- KRKevin Rose
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, um, that was, that was a big, big shock to me. Um, I remember just those conversations being like... I was like, "Wow, for 21..." I was definitely not as put together [laughs] as, as he was at 21.
- SPShaan Puri
Wh- what's something he said that made you, made you think that?
- KRKevin Rose
Well, you know, one of the things that I was always, uh, frightened by, uh, as an entrepreneur, uh, in my, in my youth was just this idea of would people take me seriously, um, and could I admit when I didn't know something? And i- was it, was it okay to... I- I tried to hide my vulnerabilities as an entrepreneur. And he just came in and was asking so many pointed questions. And, um, you know, I asked him about some of his hiring and firing practices and, um, how he would edit his team, um, how he ensured that he made the right hires, uh, 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 w- wasn't the AWS's of the world, and we were talking a lot about that. And, um, it was just, it was one of those things where he just told me that, um, he just, you know, s- it's the obvious stuff. You surround yourself with, with people smarter than you and then you ask a lot of questions and you're not afraid to ask those questions. So, um, you know, back then I had some great investors and, and board members, but at times I was a little hesitant to be like, "Hey, I, I don't quite understand how this works. Can you help educate me?" And I think it was due to my lack of... Like, for some reason I thought because I was a college dropout that I, I, I had to hide that and, and they would be like, if I asked a question that I should've learned in college, that-
- SPShaan Puri
[laughs]
- KRKevin Rose
... it woulda looked, uh, I'd have egg on my face. And so there was a lot of, um, of, of nervousness around that. A- and just to see Mark just be so open a- and just curious, um, and there was no... It was clear that if he, if he didn't know something, he was gonna get to the bottom of it right away. Um, it was, it was inspiring.
- SPShaan Puri
I had a, I, I had an experience just like that when we were selling our, our last company. Um, I met with all the big companies, Facebook, Google, uh, Amazon, whatever. We also mes- met with Discord, and I go in, I meet Jason, who's the CEO of Discord, and I'm, like, k- 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 I... W- 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 sorta like You know, I would acquire you guys 'cause 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. [laughs] 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-
- KRKevin Rose
Mm-hmm
- SPShaan Puri
... 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 kinda giving him some ice cream of like, "You can have this, too."
- KRKevin Rose
Right, right, right.
- SPShaan Puri
And, a- and I just thought, "Oh, that's what like, uh, this is, this is probably what Zuck was like. You know, this is probably what somebody who was focused was like 'cause back when Zuck was building Facebook, it was like MySpace was adding music and then TV shows-
- KRKevin Rose
Right
- SPShaan Puri
... 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-
- KRKevin Rose
That's right
- SPShaan Puri
... Facebook was so mu- such a cleaner site than MySpace and all the other competitors that were out there.
- KRKevin Rose
Yeah, I would argue they've lost a lot of that 'cause they say yes to a lot of the cloning of features of other, other competitors.
- SPShaan Puri
[laughs]
- KRKevin Rose
But yeah, you're right. That relentless, um, focus is, is so essential, and oftentimes it's, it's more what you say no to than what you say yes to on, on the product side. You know, I- I, that totally agrees and vibes with me, for sure.
- SPSam Parr
Do, do you sort of, uh, when you're doing all these projects, uh, back to the projects, do, do, do you have like a set of rules? Like, for example, I know a guy who, uh, is incredibly successful. Um, I talked to him one time. His name's Kevin. Or a c- couple times. His name's Kevin Ryan. He started like MongoDB, Business Insider, Gilt Groupe, all these like amazing companies. And he was like, "Well, I just do back of the envelope math and then I give each project six months, and me and my partner typically fund it with $300,000. And we kinda like feel it out. It's a little mathematical, but it's also like, well, let's just see what happens in six months and see if this is promising and we'll decide." Uh, and so he's like, "Six 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.
- KRKevin Rose
Hmm.
- SPSam Parr
And they said something like, they're like, "Yeah, well, like sometimes we'll only spend 50 grand and like two 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?
- KRKevin Rose
Yeah, that was the name of the, the kinda incubator studio. Yeah, we created-
- SPSam Parr
Like do, do... Yeah. Do you like have like rules for what you're looking for?
- 27:27 – 36:35
Beginnings of Hodinkee
- KRKevin Rose
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, in a middle-class household is a big deal. Like, that's, like, back in the '80s, uh, you know, when my dad bought that, he was just like, "I've made it." You know, I have a... 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, th- 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 Watchville, which was an aggregator and an app that brought together all of these different sources so that people can read this stuff on the mobile, uh, on their mobile phone. Because a l- a lot of, as, as silly as it sounds, back then, most of the, [coughs] 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 wa- that was just horrible. So I, I, I, I made it all very readable, um, push notifications, like, all this stuff, just a, kind of a wrapper for, like, all of this great content, and it, it just started growing and growing and growing, and I had a lot of eyeballs. Like, some of the, the, the biggest collectors were, were now using the product. And, um, you know, I, 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, had a couple full-time writers. And so w- I talked to Ben and said, "Hey, you don't have the tech team here. Let- let's, let's merge and, and combine forces." So we, um, we merged the two companies together. Um, he was three or four people, and I was three or four people. Um, I moved to New York, became CEO. At the time he was doing, uh, maybe a million and a half to $2 million a year in revenue, um, so just enough to kinda do payroll. And, um, we grew it from there, and then turned on e-commerce, and then started selling, uh, and, 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 v- 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 kinda give you a little bit more concierge help on the apps stuff. And they said that they had seen their, uh, a $250,000, um, transaction come through Apple Pay, um, on an American Express, and that was, like- The largest known transaction at that time-
- SPSam Parr
No shit
- KRKevin Rose
... had, had been over Apple Pay for a sight unseen, a vintage Rolex, which was, uh, which was kinda crazy. But anyway, yeah, so that, I mean, i- i- new, new, new luxury watches are double digit billions of dollars in a year, um, i- i- in, in terms of market size. So it's, it's a big industry that, that many people, uh ... I- it's not as apparent in the States. Um, when you go overseas, uh, uh, you'll see how i- in, in, in Europe there, you know, watches are so much more, uh, kind of a, a, a, a, a type of thing that is, is worn versus smart watches are more of the norm, or no, no watch at all, uh, here in the States.
- SPSam Parr
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?
- KRKevin Rose
Yeah, yeah. We're over 100 million in revenue now.
- SPSam Parr
Man, that is wild.
- KRKevin Rose
That's insane. [laughs]
- SPSam Parr
And, and, 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 gonna 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 gonna buy a Buzzfeed oven. I just don't think that's gonna happen." And you guys did it, and I was like, "I don't know. Is this like gonna be a thing? It seems so challenging." But you guys are a perfect example of that. You know what the other good example? Do- I bet you go to Bring a Trailer. Do you go to bringatrailer.com?
- KRKevin Rose
I've been to Bring a Trailer many times, yeah. Uh-
- SPSam Parr
It is awesome
- KRKevin Rose
... the founder, Hodinkee, it's one of his favorite sites actually.
- SPSam Parr
They are awesome. And so they've done the same thing but with cars-
- KRKevin Rose
Mm-hmm
- SPSam Parr
... where basically it's like this perfect tie of like I just ... I, I bought one car from actually, uh, those websites, and, um, but I read it every single day. I'm like-
- KRKevin Rose
Mm-hmm
- SPSam Parr
... "Let's just see like what they're gonna write about, what cool car is 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.
- KRKevin Rose
Yeah, those are great.
- SPSam Parr
It's awesome. But what, um, what other verticals or what other like industries have you thought, "Man, maybe I could actually do this model"? Uh, 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, I bet you're at, at night, you're like, "I'm not gonna do it, but I bet you I could apply this here, here, and here."
- KRKevin Rose
Yeah. I mean, i- in some sense it's kinda what we're doing right now in the world of NFTs, where there, 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, 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 editorial so seriously and really hired out just a, a absolute stellar team of writers that had a deep understanding of the world of watches, and not just a announcement this is a new watch that was dropped, but a 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, um, a, a microwave or some like inexpensive [laughs] 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, you know, w- w- watch or collectable," and because of that, um, you know, you're willing to pull the trigger on a, on a 20, 30, $50,000 purchase. So, um, it's, trust is so essential.
- SPSam Parr
Do you think that ... Well, I, at The Hustle we are trying to h- we hired a bunch of writers. Shaan hired some writers as well for his thing. It was 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, uh, watches?
- KRKevin Rose
Yeah. I mean, the best way to do that was to find people that had the natural, organic, built-in a love for, uh, horology, like just this desi- for, for all things mechanical watches. So you know, we would have writers that, um, if you t- take for example like the Speedmaster, the, the, the, 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 pl- uh, apply an editorial layer over the top of it, where you have copy editors that come in and help, you know, stitch together a, a better, more, more cohesive story before you actually publish it out to the world.
- SPSam Parr
Yeah, I love that.
- SPSpeaker
[upbeat music] This data is wrong every freaking time.
- SPSam Parr
Have you heard of HubSpot? HubSpot is a CRM platform where everything is fully integrated.
- SPSpeaker
Whoa, I can see the client's whole history, calls, support tickets, emails, and here's a task from three days ago I totally missed.
- SPSam Parr
HubSpot. Grow better. 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 a 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
- 36:35 – 44:12
What gets you excited?
- SPSam Parr
gets really pumped up. What gets you really pumped up?
- KRKevin Rose
Ra- rage is my fuel
- SPSam Parr
I, I love, I love fighting
- KRKevin Rose
Yeah, the, so, uh, for me, new ideas and working with creative people is the, the, the most kind of like, um, strongest source of fuel for me. So when I get together with an artist or an, a fellow entrepreneur and I actually, it doesn't have to be someone that has created something big. It ha- it has- it's rather someone that just has wild ideas that, that are potentially, um, uh, j- just new, new ways of looking at the world. And so the, you meet a lot of ent- entrepreneurs that are opportunistic, iterative entrepreneurs, where they'll see something, they'll say, "Oh, there's some s- there's rough edges on that particular product. I'm gonna go sand them 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. Um, so that is what I'm really drawn to from just a, a straight idea, uh, point of view. And so entrepreneur-wise, and when I, I invest in some of these startups, those are my favorites, are, are, are those, th- those crazy, uh, um, more world-changing entrepreneurs. Um, in terms of the [coughs] the rage side of things, um-
- SPSam Parr
[laughs]
- KRKevin Rose
Y- yeah, there's-
- SPSam Parr
Dude, you've had a, you've had a bunch of rage-inducing moments. I've, I've followed your career.
- SPShaan Puri
Dude.
- SPSam Parr
I've seen, I've seen you throw the fucking raccoon.
- SPShaan Puri
I saw you with the raccoon.
- SPSam Parr
Yeah. I've seen you-
- SPShaan Puri
I saw you with the raccoon. We saw that one. [laughs]
- KRKevin Rose
[laughs]
- SPSam Parr
I've seen people pro-
- SPShaan Puri
And the raccoon dog
- SPSam Parr
... 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, I don't know like the whole story, but, like, you, you've had, you've kind of been a target.
- KRKevin Rose
Yeah. I mean, those, th- th- those all have their own unique story, that the historical building thing was definitely not true. [laughs]
- SPSam Parr
[laughs]
- KRKevin Rose
That, that, that was a f- that was a pretty funny one in that, um, but w- 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 wanna 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 four to five years of, of my life has been spent, um, trying to, to, to kind of master my own mind. And, and it, I, I think that if you can't, um, come to grips with your own and pers- like, personal peace of mind, uh, it, it's, it's a horrible place to be. And so, you know, I, I remember as a young entrepreneur just kind of, uh, being on this 24/7 hustle to go build, build, build. I gotta win. I have to win. I have to win. And it created a level of anxiety that was not good for me. And, and so I think that's prob- probably why you saw me kind of do things like the meditation app and other, other things, 'cause I, it was just a, a natural forcing function for my, my own self to like take some of that stuff more seriously. And so, you know, um, I, 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 I, there is 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 um, and it's, it's, it, uh, for me, it, it's always been, um... That, that has been not a blessing, but something that I, it's just been, has weighed on me. And, and I've always tried to, um, I guess the, the big push in the last few years have been to try and wrangle that.
- SPSam Parr
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, Kevin?
- SPShaan Puri
Well, let's do 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-
- KRKevin Rose
Right
- SPShaan Puri
... 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 them and run with them or, or find something interesting in it."
- SPSam Parr
By the way, have you ever talked to Palmer, Kevin? That guy is wild.
- KRKevin Rose
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 s- I've seen some written interviews, but never, never anything on video form.
- SPSam Parr
It, it went live yesterday. It's on like you- our YouTube and, um, most of our listenership's on, like, podcast, uh, 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 Balaji, but more, um... 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.
- KRKevin Rose
Yeah. I, I had read some stuff and, and I, I don't know how much of it is true, but some of his, his company stuff that he was creating around drones for tracking people and, and some of the stuff-
- SPSam Parr
It's controversial.
- KRKevin Rose
Yeah. I just, it doesn't, it doesn't fit well with my ethos, so I, I, I haven't really followed his career as, as closely. But, um, I'd be curious to listen to the interview for sure.
- SPShaan Puri
I think it was probably w- uh, it was probably our best guest episode. Uh-
- 44:12 – 57:04
What ideas/projects are you interested in?
- KRKevin Rose
that I'm, I'm really drawn to, is just, like, people that are hacking on stuff, um, at night. You know, for me, a, a lot of the stuff that, that I think about in that, that vein I tend to outsource and get other people to, to, to work on it. Um, a lot of the stuff around, um, longevity I've been interested in, uh, specifically, uh, uh, a drug, uh, called rapamycin wh- where it's been proven now to extend life in, 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 s- I still put a lot of effort and time and, and attention in, and I, I try this stuff out on myself as well. You know, I'm, I'm, I'm trying some of these experimental things. Um, not because I, I'm not one of these people that wants to put, you know, young people's blood in them and live forever. I, I, I, I wanna die. I just, you know, I, I do like the idea of-
- SPShaan Puri
Not yet
- KRKevin Rose
... uh, since I am an ol-
- SPShaan Puri
[laughs]
- KRKevin Rose
Well, I am an older dad. I, I didn't have my first kid un- until my four- until I was 40. I, I, I would like to be around a little bit longer for them. That's, that's all.
- SPSam Parr
Well, I've heard of people doing this. I know Tim's doing this with, uh, what's it called? Psilocybin, uh, like, mushrooms. Um-
- KRKevin Rose
Yeah
- SPSam Parr
... psyl- psyl- psyl-
- KRKevin Rose
Psilocybin.
- SPSam Parr
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? W-
- KRKevin Rose
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 de- detect, um, certain levels of, of, um, uh, of output. Uh, you need a larger sample base, uh, in this 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, um, I believe up to 10% lifespan increase. And so to power it, um, was to add another million dollars or so into the study, um, to, to make sure that they could bring on the additional canines required to make that happen. And, um, you know, I put my dog on it as well and, and I, and he's, um, 12 now, and he still runs around like a pup. And, and-
- SPSam Parr
[laughs]
- KRKevin Rose
... um, I attribute some of that to, to a, a cycle of this that he did. Um, but yeah, it's, it's nothing other than just, like, you, 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, you're like, what, what is meaningful to me personally. And, um, uh, th- 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-
- SPSam Parr
Yeah
- KRKevin Rose
... live for an additional five years, like, what a win, you know? So that, it was-
- SPSam Parr
Yeah
- KRKevin Rose
... kind of a, a win-win study.
- SPSam Parr
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, so things are going well for him. But I w- he was kinda 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 kinda 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-
- KRKevin Rose
Yeah
- SPSam Parr
... yeah, you know, fuck it. Give me that pill. I'll take that thing." Uh-
- KRKevin Rose
Yeah
- SPSam Parr
... because they're s- they're so much easier to convince to f- to give it to their dog.
- SPShaan Puri
I'm with Kevin.
- KRKevin Rose
Oh, for sure. And, and there's, there's so much-
- SPShaan Puri
Let the humans die, but dogs live forever.
- KRKevin Rose
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, y- out of 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 i- in the next five years is gonna change everything. Um, we're seeing open, 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 will just be non-existent. Um, 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, the outputs that you're getting now from prompt-based art, um, you know, the future versions of Photoshop are, are not gonna be about moving a 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, and it'll all be done via prompt and, and meaning that 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, in, in medicine, uh, obviously all the creative side. There's a, a probably a half dozen or so tools now that will complete, uh, you know, write complete paragraphs for you if you're writing sci-fi. You give it some initial kinda prompts of where you want the story to go, and the writing is quite good. Uh, I, I have no doubt in the next five 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, uh, 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 i- 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, I'm actually gonna pivot into this, this new world of AI." And anytime you watch that kind of flow of high-quality engineering talent go move into something, you, you, you pay attention. So I'm looking for at a lot of investments in that particular sector, um, and I'm, I'm very bullish on it. And it's something I don't have time to work on, but I, I believe some great businesses are gonna be built there.
- SPShaan Puri
What would be an application you would wanna do in that space? So of all those kind of like threads where it's like creative work-
- KRKevin Rose
Yeah
- SPShaan Puri
... medicine, um, you know, writing a, an AI book, is there an application that you can think of that you're like, "I feel like AI could solve this." W- 'Cause I think that's the, that's the... It's a hammer in search of nails at this point. Uh, that's the... When I talk to engineers-
- SPSam Parr
Well, Shaan, you made a joke. You made a joke. I, I, I always tease Shaan about Web3, 'cause I'm not the biggest fan of it, and he was... And we were joking about how, uh, he was, like, coming up with ideas with, with AI, and he's like, "Finally, a use case. We found it." [laughs] And like with AI it seems like there's actually way more obvious use cases, right? But, uh, yeah, what, what application excites you?
- 57:04 – 1:00:29
Web3 debate
- KRKevin Rose
it comes to Web3.
- SPSam Parr
You want me to tell you my, why I'm not a fan of this and you can-
- KRKevin Rose
Yes, please
- SPSam Parr
... you could... I'm gonna get you, I'm gonna try and get you fired up here, and then-
- KRKevin Rose
Yeah
- SPSam Parr
... we can talk about-
- KRKevin Rose
Let's, let's try
- SPSam Parr
... we can talk about Proof. I do. It sounds like I'm making an easy out, which I kinda am. But basically, like I am, I'm, I'm, I'm decently educated just by hanging out with Shaan, and so I have to admit that like some of my beliefs are a little bit loosely held, uh, and, 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 kinda 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 it, 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, "W- Web 2.0 is old," and like the way the, "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-
- KRKevin Rose
Mm
- SPSam Parr
... 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 point, 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 decentral- Like, it's like, no, I... Like, there are some things that I want like to have a, to, 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-
- KRKevin Rose
[laughs]
- SPSam Parr
... 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 kinda bothered me.
- KRKevin Rose
Yeah. I mean, I, I, I feel your frustration there in that I too am, 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, I'll give you a great example. Um, we're, we're working on, um, th- there's a lot of things that you wanna do in Web3. Some of them are high value and some of them are, are low value. W- when you were talking about working with the community, so we have a community of people that come together to do all, 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, uh, items, where you receive an NFT or something that is, um, actually has some financial, like, you know, something behind it. That is a case where you wanna actually have that hardware wallet and pull it out and, and do it in a way that is secure and that is protected and, um... 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 and, and 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, uh, maximalists, and I think maximalists is really what we're talking about here. Because anyone that is a maximalist, uh, on-
- SPSam Parr
A maximalist means what? Just like extreme, an extremist?
- KRKevin Rose
It just means that you are so into something that you can't see any other way,
- 1:00:29 – 1:21:08
Crypto
- KRKevin Rose
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.
- SPSam Parr
Isn't Pomp-
- KRKevin Rose
And if, if-
- SPSam Parr
Pomp's our, our, our buddy. Isn't Pomp... Like, don't they call him-
- KRKevin Rose
Pomp, Pomp's a little-
- SPSam Parr
... online like a Bitcoin maxi?
- KRKevin Rose
He- I don't think he... I think he is a maxi on Bitcoin.
- SPSam Parr
[laughs] Yeah.
- KRKevin Rose
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 wanna get into, to political talk, but any time you get to the fringes of anything-
- SPSam Parr
Sure
- KRKevin Rose
... 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 th- I'm with you. I 100% agree. But that said Like I've seen this idea in 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. Uh, maybe it's 50,000 or 75,000. It's 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 ins- insane monthly nut that that company has to cover, um, you know, th- those dollars are, are not, are 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 a e- email address that you can send it if something is 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... I think that the, the ones that really win here, yes, there are gonna be the people that say, "Self-custody is the only way." They... There's this famous saying that if it's not your k- keys, it's not your crypto. Like, like you have to hold your own private keys. I, 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 Web3 completely agree with you, and that let's not throw away the baby with the bath water here. There's a lot-
- SPShaan Puri
S-
- KRKevin Rose
... 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, actually, that, that does make more sense than the old way of doing things."
- SPShaan Puri
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 their mission in life is to basically find every stupid use case of crypto-
- KRKevin Rose
Mm
- SPShaan Puri
... and highlight it, or every bad investment or every-
- KRKevin Rose
Sure
- SPShaan Puri
... clip of a, 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, and there's some-
- KRKevin Rose
Are you talking about me? 'Cause I was just on their podcast two weeks ago, so. [laughs]
- SPShaan Puri
No, no, they, uh, I haven't seen it yet.
- KRKevin Rose
Who, who, who, who interviewed you?
- SPShaan Puri
You're, you're safe so far. Uh, Dixon.
- KRKevin Rose
Nice.
- SPShaan Puri
But like, you know, there's, there's people that sort of are, 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 em- embarrassing to spend your whole day poking holes in, in something, you know. Uh, but let, let's put it this way. I'm a, on this podcast, I'm the, the crypto believer. I'm the one who puts-
- KRKevin Rose
Mm-hmm
- SPShaan Puri
... a significant portion of my net worth. I have a crypto c- media company. I have a bunch of belief in crypto.
- KRKevin Rose
Mm-hmm.
- SPShaan Puri
But for this use ca- for this exercise here, I'm gonna, uh, point out two things that I think, uh, or would be s- would be, you know, strong and valid points against crypto to somebody like you, who is also a, a crypto believer. So I want you to kinda argue against these, and I hope that, uh, this doesn't get clipped as like-
- KRKevin Rose
Sure
- SPShaan Puri
... 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.
- 1:21:08 – 1:28:06
Portfolio
- SPSam Parr
that. What, what is your liquid portfolio look like? Like where, I-
- SPShaan Puri
Like
- SPSam Parr
... I, I was a- I was, been waiting to ask you that. Like-
- SPShaan Puri
Sam is like a ETF, low-cost ETFs and bonds guy.
- KRKevin Rose
Dude, I'm-
- SPShaan Puri
I'm-
- KRKevin Rose
... I'm 80% indi- Vanguard index funds, 20% bonds. That, that's all. And then I build-
- SPShaan Puri
Yeah
- KRKevin Rose
... private businesses.
- SPShaan Puri
Yeah, so, so-
- KRKevin Rose
Whereas Shaan, like, has put everything into-
- SPShaan Puri
I'm like-
- KRKevin Rose
... well, angel investing
- SPShaan Puri
... I'm like investing in crypto and then, like, you know, five companies I believe in and, you know, a little bit of index funds. Like, it's like-
- KRKevin Rose
Yeah
- SPShaan Puri
... 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.
- KRKevin Rose
Yeah, so, so my, my pie chart would be essentially this. Um, you know, 80%... Well, the, I think that is an important thing to caveat here is that as a, a venture capital, uh, partner over at True Ventures, I have a lot of, um, risk on the table there in, in venture early stage investments. So-
- SPSam Parr
Did you have to put your own money into that, or is that just your carry?
- KRKevin Rose
I do, yeah. I have to put my own money into it. As, 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-
- SPShaan Puri
But you don't-
- KRKevin Rose
... of high, high risk
- SPShaan Puri
... you don't have to put too much capital in, right? You put like, I don't know, what, like quarter of a million dollars or a million dollars, something like that in- into that? Does it-
- KRKevin Rose
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, a percent of, uh, of that, um, in, back into the fund. Uh, I'd have to look at what the exact numbers are, but it's, 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, 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 r- rely on people to buy bonds on my behalf. Um, you know, I am laddering into, um, uh, bills right now because you're getting 4+% in the short term. And so, you know, just, just ladder into, to, to those makes a ton of sense right now. Um, you know, anyone out there that has 10 grand that's sitting around that doesn't go buy an I bill right now that's e- earning over 9% is just insane. Like, that's the most no-brainer scenario for, for someone that's listening to this podcast. Um-
- SPShaan Puri
By the way, there's like one week left of that, right? There's like-
- KRKevin Rose
Yeah, that's right
- SPShaan Puri
... or, or less maybe.
- KRKevin Rose
Obviously not investment advice-
- SPShaan Puri
[laughs]
- KRKevin Rose
... 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, uh, amazing. So, um, anyway, it, 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%-
- SPSam Parr
What, what, what-
Episode duration: 1:28:06
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