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Kevin Rose
Partner at True Ventures, True Ventures

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

📅 Jul 25, 2026 BlackNova Productions 88 MIN 176 SEGMENTS · 4 SPEAKERS
Episode 382: Shaan Puri (@ShaanVP) and Sam Parr (@TheSamParr) talk to Kevin Rose (@kevinrose), entrepreneur, founder, VC and CEO of many projects, about creating an online magazine that garners $100M/year focusing on watches, what projects he's interested in, why he loves crypto, and where he invests his money. ----- Links: Kevin Rose DIGG Proof Hodinkee agelessRx Do you love MFM and want to see Sam and Shaan's smiling faces? Subscribe to our Youtube channel. Want more insights like MFM? Check out Shaan's newsletter. ------ Show Notes: (03:15) - Kevin's background (13:40) - Meeting Mark Zucker...

What Kevin Rose said

Written from the verified transcript and checked against it. Every figure links to the moment it was said.

Kevin Rose discussed his career from Digg to angel investing and his current ventures. He said Hodinkee, the watch blog he merged with, now exceeds $100 million in annual revenue. He detailed his early investments, including $25,000 in Twitter's seed round, which became millions. He explained his approach to starting businesses, noting that most fail but a few succeed, and he shared his criteria for killing or maintaining projects. Rose discussed his NFT project Proof, arguing that NFTs have real use cases beyond speculation, such as provenance for luxury goods and loyalty programs. He also talked about his investment philosophy, stating that most of his non-venture portfolio is in low-cost index funds, with about 10% in crypto. He expressed bullishness on AI, predicting it will transform creative industries and that Fiverr will become non-existent. He also mentioned funding longevity research, including a rapamycin study on dogs.

Key takeaways

  1. Hodinkee now generates over $100 million in annual revenue, up from $1.5-2 million at the time of the merger.
  2. Rose invested $25,000 in Twitter's seed round, which turned into millions of dollars.
  3. Rose's non-venture portfolio is about 90% in low-cost index funds, with about 10% in crypto (50% NFTs, 50% digital assets).
  4. Rose predicts AI will destroy the low end of the creative market and that Fiverr will become non-existent.
  5. Rose is funding a rapamycin study on dogs to extend lifespan, with an additional $1 million to power the study.

Numbers and commitments

FigureWhat it refers toTypeAt
$100 million Hodinkee annual revenue metric 0:23
$25,000 Investment in Twitter's seed round commitment 29:56
$35 million Sale price of Revision 3 price 6:46
38 million Monthly users of Digg at its peak metric 5:30
10% Portion of overall portfolio in crypto metric 1:23:32
50% Crypto portfolio in NFTs metric 1:23:32
50% Crypto portfolio in digital assets metric 1:23:32
4% Interest rate on Ethereum staking via Coinbase metric 1:00:43
9% Interest rate on I-bills metric 1:22:24
$750 million Size of True Ventures' latest fund metric 1:22:24

Chapters

  1. 0:00Digg and early career
  2. 3:38NFTs and Proof
  3. 7:28Angel investing in Twitter and Facebook
  4. 27:27Hodinkee and watch business
  5. 44:09Longevity research and rapamycin
  6. 48:23AI predictions
  7. 58:46Crypto debate and use cases
  8. 1:21:06Investment philosophy and portfolio

Questions asked in this interview

12
  1. 0:00What the hell is this guy thinking?
  2. 2:44At Digg, you've done—is it—I read it all the time, but is it pronounced Hodinkee?
  3. 7:22And maybe that sale gave you the ammo to do angel investing, or would you have been able to do it without it?
  4. 10:12Or where was it in that?
  5. 19:25Do you have 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 was that the name of the production company?
  6. 26:13Like I remember I read that and I was like, I like this business because I'm into it, but this guy's frankly way above this. What is he thinking?
  7. 34:27What did you find was the best way to do that for watches?
  8. 41:13By the way, have you ever talked to Palmer, Kevin?
  9. 50:38But yeah, what application excites you?
  10. 57:05You want me to tell you why I'm not a fan of this?
  11. 1:21:06What does your liquid portfolio look like?
  12. 1:24:24Do you regret owning or do you like being an owner?
Sam Parr 0:00 ↗
When I saw you went and did the watch site, Hodinkee, first of all, Sean, have you ever read that? Like 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?
Sean 0:15 ↗
Did you just say that it went from like a million or two in revenue and now it's—Sam said it's over a hundred million.
Kevin Rose 0:23 ↗
Yeah. Yeah, we're over 100 million in revenue now.
Sam Parr 0:25 ↗
Man, that is wild.
Sean 0:26 ↗
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's been a VC. He's been a founder. He recently launched an NFT project that's done hundreds of millions of dollars worth of NFT sales.
And so, Kevin's been around for a while. And the cool part of the interview, if you listen to it, you're going to see very chill guy, very down to earth, very humble, and not a kind of like, oh my god, I'm going to 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 people who play the game 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, he's creating Watchville, this niche project for watches that grew from 1 million in revenue to now over a hundred million after it got acquired and merged with Hodinkee. Then also we talked about how he hires writers. We talked about 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. How does he invest it? Where does he put it? And the answer is not what you may have expected.
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 hope you enjoy this episode with Kevin Rose. I liked it. I think you will too.
Sam Parr 2:14 ↗
We should give like a brief overview, but like your resume—we don't really talk too much about résumés 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?
Kevin Rose 2:31 ↗
2004.
Sam Parr 2:32 ↗
2004. That's right. Yeah. And so, it was like one of the original 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?
Kevin Rose 2:43 ↗
Business Week.
Sam Parr 2:44 ↗
Business Week. 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 it had all this hype, but Digg didn't turn out maybe as wonderful as we all thought maybe it could have done. But then you had your finger on the pulse of all these other things you've done. At Digg, you've done—is it—I read it all the time, but is it pronounced Hodinkee?
Kevin Rose 3:04 ↗
Hodinkee.
Sam Parr 3:06 ↗
Hodinkee. Yeah. Hodinkee. A watch blog that also 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 Oak 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 basically my point is you're kind of an internet OG and you are incredibly prolific. I mean, does that kind of summarize it?
Kevin Rose 3:38 ↗
Yeah. I mean the most recent thing I started was Proof which is our venture into the world of NFTs and so that's the only thing missing from that and that's about 10 months old now so that's on the newer side.
Sam Parr 3:53 ↗
So from the outside if I look at this kind of collection of—or like the career path—it looks very random. It's like from venture-backed to angel investing to venture investing to kind of like niche communities, these kind of apps that are like simple, like meditation or fasting. You did a podcast, you did a show, you've done a bunch of content, you did a bunch of different things. Was there a method to the madness? Do you just describe it as random or is there kind of like some underlying theme to this whole thing?
Kevin Rose 4:29 ↗
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. You know, probably at least 10 to 15 businesses of which 90% of them go to zero and then there's a few that pop and become pretty big. So it's just this idea that 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.
Sam Parr 5:14 ↗
Of all those projects—and I'm actually going to exclude Proof from that because 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?
Kevin Rose 5:30 ↗
That's a good question. Certainly I would say when I was in the middle of Web 2.0—which was when Digg was at its peak, which was about early 2006—we hit around 38 million people a month using the site. It was, of the Web 2.0 properties, it was one of the largest. It led me to sitting down at dinners and conversations and hangouts with the Jack Dorsey's and Evan Williams and Zuckerbergs and all 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—well, I would say there's two things—well, three—that are—two are unrealized. And Hodinkee is going to be crazy. It's over 100 million revenue a year now, which is nuts.
Sam Parr 6:45 ↗
Whoa. Really?
Kevin Rose 6:46 ↗
And then we have 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, Revision 3, where I was the co-founder, is a media company that became Discovery Channel's digital arm, and we sold that for $35 million back in 2008 or something like that. So, that was probably the biggest company sale that I've had. But you know, they're much larger on the more angel investment side.
Sam Parr 7:22 ↗
And maybe that sale gave you the ammo to do angel investing, or would you have been able to do it without it?
Kevin Rose 7:28 ↗
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 Digg really took off 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? And so I sold a little bit of my Digg stock, enough to give me the ammo to go and do small seed checks, and put 25K into Twitter's seed round and put—25K or it was more into Facebook, but they were a little bit later stage. And so it was those little tiny checks that, when they turned into multi-billion dollar businesses, were pretty meaningful.
Sam Parr 8:22 ↗
How much does 25K into Twitter and Facebook early on actually turn into?
Kevin Rose 8:27 ↗
Millions of dollars. I mean that math is even hard to comprehend.
Sam Parr 8:32 ↗
In Twitter's seed round, what was the valuation then?
Kevin Rose 8:34 ↗
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—
Sam Parr 8:49 ↗
Odeo.
Kevin Rose 8:51 ↗
That's right. They were Odeo. So, 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 the 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 his stock? And I was like, yeah, that sounds great. I'll just buy some stock.
Sam Parr 9:23 ↗
I think Gary Vaynerchuk said the same story and he bought after me.
Kevin Rose 9:27 ↗
Yes. 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 five or ten-xed 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 and then Gary had to pay the more expensive price, but that was a funny little—
Sam Parr 9:59 ↗
What do you think Blake's saying right now? I mean Blake probably just—
Kevin Rose 10:01 ↗
He held on to like half or more. And so you know he probably—I don't know—if I had to guess he made 50 plus, 75 plus million dollars or something on it. He—I'm sure he's okay.
Sam Parr 10:12 ↗
Did—at the time, because Twitter kind of had like—well, there's Odeo kind of failing, Twitter, who knows? And then there was like this small community of people in Silicon Valley that were using it back when it was like texting your updates out. Like when you were writing that check, did you feel like this is 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 in that?
Kevin Rose 10:37 ↗
I felt it was the next big thing because there was—I loved so—as someone that was building a social graph of sorts at Digg, there was always this idea prior to Twitter that was bidirectional friendships. So 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, would you like to send a friend request? Yes. Do you accept this friend request? Yes. And it was the same thing with Facebook. And when Twitter came out with that model of just this idea of following—and it allowed—there was no celebrities on the platform. It was like me and Leo Laporte and a couple others that were the top followed people on the platform at the time. But I thought to myself like, wow, if this catches on with the celebrity crowd, it's just going to be insane. Because everyone will just want to see. And also the barrier to entry—a lot of back then it was impossible to get celebrities to sit down and do technical things because we didn't really have smartphones. But the fact that you could text to that number, that short code, just what you were up to, anybody can do that. It doesn't require any special software. It doesn't require you sitting 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 kind of catching on, I knew eventually it would spill outside of that small vertical of users into the mainstream. And when that would happen, that was the bet. And when that would happen, it would blow up. And it did. So that was awesome.
Sam Parr 12:28 ↗
And I've also seen—you did a video back in the day when Square was like a prototype. It was like a YouTube video. I remember you were like, hey, yeah, check this out. Like, here's this little Square and you could plug it into your phone, you could take credit card payments. And it was not even released yet. And you were like, promote—I think did you invest in that too? Because that would have been like another mega winner.
Kevin Rose 12:51 ↗
That's a funny 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 was like, oh, dude, it's oversubscribed. I'm sorry. Like, we've closed the round. 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 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.
Sam Parr 13:29 ↗
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 startups are quite popular and Jack Dorsey is like basically a celebrity. Mark Zuckerberg is obviously a celebrity. What was it like back then in 2004, 2005, 2006, 2010 when these things were just getting going? Did you actually think that a guy like Jack Dorsey was going to be this titan of industry like he kind of is? Like what was it like being around some of these folks early on when you guys were just messing around?
Kevin Rose 14:05 ↗
Well, it was—you met a lot of entrepreneurs back then and 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 pick their brain more and get to know them better. And so, one of the things that struck me is just how mature Mark Zuckerberg was when he was younger. Like, I'm quite a bit older than he is.
Sam Parr 14:35 ↗
How old is he now? He's still only like 38.
Kevin Rose 14:38 ↗
He's younger than that.
Sam Parr 14:40 ↗
Oh my god.
Kevin Rose 14:41 ↗
Yeah. So, how old is Mark? Oh, yeah. You're right. He is 38.
Sam Parr 14:48 ↗
Yeah.
Kevin Rose 14:48 ↗
That's still—I mean he's in his 30s. That's pretty wild. Yeah. And it's crazy. He was really young. So when I met him was 2005, I want to say. So he was 21.
Sam Parr 15:05 ↗
Wow.
Kevin Rose 15:05 ↗
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—he was at 21.
Sam Parr 15:31 ↗
What's something he said that made you think that?
Kevin Rose 15:35 ↗
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 and 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 that was a very challenging thing to do back then to scale websites. You were racking your own servers and there wasn't the AWS's of the world and we were talking a lot about that.
And it was just one of those things where he just told me that 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—like 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 have 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 it was clear that if he didn't know something, he was going to get to the bottom of it right away. It was inspiring.
Sam Parr 17:25 ↗
I had an experience just like that when we were selling our last company. 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 basically if you bought our thing, it would add this dimension to Discord, it would be awesome. And what I was so used to was most founders, 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, totally. We can do that too. It all sounds good. And he was just sort of like, you know, I would acquire you guys because I like you and I like that you came in and you had this whiteboard and you just painted a picture for me. But we won't do any of that. And he's like, 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 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.
And I just thought, oh, that's what—this is probably what Zuck was like. This is probably what somebody who was focused was like. Because back when Zuck was building Facebook, it was like MySpace was adding music and then TV shows and doing these brand deals and he was just like, nope, real names, simple profiles. We're just going to let you communicate and add photos and do this stuff. And he said no to a bunch of different things, which is why Facebook was such a cleaner site than MySpace and all the other competitors that were out there.
Kevin Rose 19:03 ↗
Yeah, I would argue they've lost a lot of that because they say yes to a lot of the cloning of features of other competitors. But yeah, you're right. That relentless focus is so essential and often times it's more what you say no to than what you say yes to on the product side. You know, that totally agrees and vibes with me for sure.
Sam Parr 19:25 ↗
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 is Kevin Ryan. He started MongoDB, Business Insider, Gilt Group, all these 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 kind of feel it out. It's a little mathematical, but it's also like let's just see what happens in 6 months and see if this is promising and we'll decide. 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—they're not really an incubator. They start companies. And they said something like, yeah, sometimes we'll only spend 50 grand in 2 months or something like that. Do you have 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 was that the name of the production company?
Kevin Rose 20:26 ↗
Yeah, that was the name of the incubator studio. Yeah.
Sam Parr 20:30 ↗
Yeah, do you have like rules for what you're looking for?
Kevin Rose 20:33 ↗
Yeah, I mean—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 often times it's because your original 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 the fasting app, for example—when I launched Zero, it sat at 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 places were picking it up and so people were just naturally searching for fasting in the app store because that's just what they do. And then that's when it exploded to hundreds of thousands and a million plus monthly active people doing fast.
But had I shut that down after the first 6 months, it would have 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. 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 organically build from here. And we were seeing nice slow consistent 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 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—
Sam Parr 22:24 ↗
Yeah, I used it.
Kevin Rose 22:25 ↗
Oh, you did? Awesome.
Sam Parr 22:26 ↗
I liked it.
Kevin Rose 22:28 ↗
Yeah, it was these little small postage-stamp-size looping videos with no audio. And we thought it would just be 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—
Sam Parr 22:45 ↗
Photo pressure. Literally because it was small, right?
Kevin Rose 22:47 ↗
Exactly.
Sam Parr 22:48 ↗
That part was actually kind of true.
Kevin Rose 22:51 ↗
Yeah. And that was a crazy one because we launched and it caught fire immediately and we had 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 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 there was no depth to it. It was a feature, not a real product. So, yeah, it varies from product to product, I guess, is the best answer I can give you.
Sam Parr 23:21 ↗
Cool. Okay. So, you talked a little bit about which one was the most lucrative. Obviously, angel investing in Twitter and then getting into Facebook and others works out well. Which one was the most fun? So, which chapter was the most fun? And kind of with that is I'm on this mission. I just—after selling companies, it's like I got time. And so I was like, all right, well, what's the priority now? I was like, I want to find out who's having the most fun in their career. Because that's what I want to do now. I just want to have the most fun type of career, who's having the most fun with their life right now. So I want to know for you which of your projects are most fun. And then who do you see—who's a blueprint I could look at where you're like, I've met this person, they're having a blast with what they do?
Kevin Rose 24:07 ↗
Yeah. Well, I would say that the nice thing about starting your own businesses is 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. We were talking about this as we were just prior to hitting record about the little podcast case holder on Amazon, right? And there's sometimes 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 that's never really interested me. It's more about 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. There's the chaos of all 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. It's never going to be just 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's kind of 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 CAC in the app store. It's really—there's so many different directions you can go and there's a decent amount of high quality entrepreneurs in the space but not as much as say building something for the app store. So I enjoy the blue ocean aspect of that world.
Sam Parr 26:13 ↗
Man, I remember when—so basically I started this company called The Hustle. It was like a daily email and we bootstrapped and sold it for tens of millions of dollars. 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 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—it started as something else, right? You started it as like Watchville or it was something else. You got acquired or merged and you became 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 was completely out of touch with it and it just seemed like a hobby project at the time. And then I started looking into it and I was like, oh wow, there's 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 this guy's frankly way above this. What is he thinking? Like this thing's needlessly hard.
Kevin Rose 27:27 ↗
Well, Watchville was so—again, just 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. For him, it was like to afford a single Rolex in a middle class household is a big deal. Like back in the 80s, when my dad bought that, he was just like, I've made it. I have a—and I'm not talking about one of the crazy Rolexes. I'm talking about just a standard Day-Date, simple Rolex. And that was like the one thing he was really proud of, that and his GMC pickup truck. So that was something I was left with. And then I started reading 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 these different sources so that people can read this stuff on their mobile phone because a lot of—as silly as it sounds—back then most of the watch sites didn't have mobile versions of their site. So they were on just old publishing software that was just horrible. So I made it all very readable. Push notifications, all this stuff, just a wrapper for all this great content.
And it just started growing and growing and growing. And I had a lot of eyeballs—some of the biggest collectors were now using the product. And Hodinkee was the most prominent source of this content that took it very seriously. So 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 merged the two companies together. He was three or four people and I was three or four people. I moved to New York, became CEO. At the time, he was doing maybe a million and a half to $2 million a year in revenue. So just enough to 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 as authorized dealers we represent several dozen of the big watch brands that are out there. And that just became a massive—it was still a relatively unknown...
Then whether or not people would actually spend large sums of money over Apple Pay, right? And so I remember we had someone from Apple that was helping us. 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 a $250,000 transaction come through Apple Pay on an American Express. And that was like the largest known transaction at that time that had been done over Apple Pay for a site-unseen vintage Rolex, which was kind of crazy. But anyway, yeah. So new luxury watches are double-digit billions of dollars a year 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, watches are so much more of a type of thing that is worn, versus smart watches are more of the normal. No, no watch at all here in the States.
Sean 31:03 ↗
Did you just say that it went from like a million or two in revenue and now it's, Sam said it's over a hundred million?
Kevin Rose 31:12 ↗
Yeah, we're over 100 million in revenue now.
Sean 31:14 ↗
Man, that is wild. Yeah. And a lot of it's commerce. I mean, you guys, 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 [__] 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 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. Do you go to bringatrailer.com?
Kevin Rose 31:46 ↗
I've been to Bring a Trailer many times. Yeah. The founder of Hodinkee, it's one of his favorite sites actually.
Sean 31:52 ↗
They are awesome. And so they've done the same thing but with cars, where basically it's like this perfect tie. I bought one car from those websites actually. But I read it every single day. I'm like, let's just see what they're going to write about, what cool cars are 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 [__]. It's awesome. But what other verticals or what other industries have you thought, man, maybe I could actually do this model? I've always thought software, but that's not nearly as sexy and cool as watches and vintage cars. But when you were thinking about this model, I bet at night you're like, I'm not going to do it, but I bet I could apply this here, here, and here.
Kevin Rose 32:33 ↗
Yeah. I mean, in some sense, that's kind of what we're doing right now in the world of NFTs, where everyone that's armed with Photoshop can create a digital 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 just a ton of projects to sort through. So what we created with Proof was 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 that isn't talking about the flipping side of the industry, that isn't talking about how to make a quick buck in NFTs, that is really talking about what would you buy and hold for the next decade plus, right? And the playbook 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 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, you develop trust. And once you have the trust of your readers, then you're able to extend commerce in a meaningful way. And it's not asking them to buy a microwave or some inexpensive throw pillow. It's saying, we have your trust. This is what we believe to be a very important watch or collectible. And because of that, you're willing to pull the trigger on a $20,000, $30,000, $50,000 purchase. So trust is so essential.
Sam Parr 34:27 ↗
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. It was a crypto thing. And 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?
Kevin Rose 34:45 ↗
Yeah, I mean the best way to do that was to find people that had the natural, organic, built-in love for horology, just 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, 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-plus writers when 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 technical information out 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 stitch together a better, more cohesive story before you actually publish it out to the world.
Sam Parr 35:45 ↗
Yeah, I love that.
Narrator 35:48 ↗
This data is wrong every freaking time. Have you heard of HubSpot? HubSpot is a CRM platform where everything is fully integrated. I can see the client's hold history. Calls, support tickets, emails, and here's a task from 3 days ago I totally missed. HubSpot, grow better.
Sam Parr 36:07 ↗
You're a pretty chill guy. When do you get like really fired up? Like what gets you excited, in a good or bad way?
Kevin Rose 36:17 ↗
I get really enthusiastic about the most random [__]. It'll be like a creative project that I'm like, I bet I could pull this off, and 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 willing to fight to the death about it, and so he gets really pumped up. What gets you really pumped up?
Sam Parr 36:35 ↗
Rage is my fuel. I love fighting.
Kevin Rose 36:41 ↗
Yeah. So for me, new ideas and working with creative people is the strongest source of fuel for me. So when I get together with an artist or a fellow entrepreneur, and it doesn't have to be someone that has created something big, it's rather someone that just has wild ideas that are potentially just 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 going to 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 really thinking about 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, when I invest in some of these startups, those are my favorites, those crazy, more world-changing entrepreneurs.
Sam Parr 37:59 ↗
Dude, you've had a bunch of rage-inducing moments. I've followed your career. I've seen you throw this [__] raccoon.
Sean 38:05 ↗
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 wanting to demolish a historical building. I don't know the whole story, but you've kind of been a target.

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APA

Rose, K. (2026, July 25). Kevin Rose: His $100M/Year Watch Blog, Money From Digg.com, & Web3 Business [Interview transcript]. BlackNova Productions. CEOInterviews.AI. https://ceointerviews.ai/interview/1134557/

MLA

Kevin Rose. "Kevin Rose: His $100M/Year Watch Blog, Money From Digg.com, & Web3 Business." BlackNova Productions, 25 Jul. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/1134557/.

BibTeX
@misc{rose2026_1134557,
  author       = {Kevin Rose},
  title        = {Kevin Rose: His $100M/Year Watch Blog, Money From Digg.com, \& Web3 Business},
  howpublished = {Interview transcript, BlackNova Productions. CEOInterviews.AI},
  year         = {2026},
  month        = {jul},
  url          = {https://ceointerviews.ai/interview/1134557/},
  note         = {Speaker-attributed transcript with timestamps}
}