Kevin Rose from Web 2.0 to Web3

We sit down with the one and only Kevin Rose to talk about his journey from pioneering Web 2.0 with Digg to leading the charge on Web3 and NFT + DeFi investing as a partner at True Ventures and his new show Modern Finance. We cover it all -- TechTV, Digg's true origin story, Milk, Hodinkee, interviewing Beeple and where MoFi goes from here. This was an episode we’ve been wanting to do forever, and Kevin was truly a blast to hang out with. Tune in and then go check out everything he’s building now over at Modern Finance! Sponsors: Vanta: https://bit.ly/acquiredvantaServiceNow: https://bit.ly/acquiredservicenow26Legora: https://bit.ly/acquiredlegoraStatsig: https://bit.ly/acquiredstatsig26 More Acquired! Get email updates https://www.acquired.fm/email with hints on next episode and follow-ups from recent episodesJoin the Slack http://acquired.fm/slackSubscribe to ACQ2 https://pod.link/acquiredlpMerch Store https://www.acquired.fm/store! © Copyright 2015-2026 ACQ, LLC Links: Modern Finance: https://modern.finance https://modern.finance/Especially the Beeple episode: https://modern.finance/episode/beeple-his-story-the-future-of-nfts-his-favorite-digital-artist-and-more/Proof: https://www.proof.xyz https://www.proof.xyz/Kevin on Twitter: https://twitter.com/kevinrose‍Note: Acquired hosts and guests may hold assets discussed in this episode. This podcast is not investment advice, and is intended for informational and entertainment purposes only. You should do your own research and make your own independent decisions when considering any financial transactions.

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

• 0:01David Rosenthal?

  Welcome to Acquired. Today, we're sitting down with Kevin Rose. Kevin was one of the pioneers of Web 2.0 as the founder of Digg and then became one of the Valley's first super angels, investing early in companies like Twitter, Facebook, and Square. Today, he's a partner at True Ventures and host of the Modern Finance Podcast. Let's chat with him.

• 0:23Ben Gilbert?

  All right. Did you like that? Should we put that in?

• 0:25David Rosenthal?

  I've always wanted to do that.

• 0:44Ben Gilbert?

  Welcome to this special episode of Acquired, the podcast about great technology companies and the stories and playbooks behind them. I'm Ben Gilbert, and I am the co-founder and managing director of Seattle-based Pioneer Square Labs and our venture fund, PSL Ventures.

• 0:58David Rosenthal?

  And I'm David Rosenthal, and I am an angel investor based in San Francisco.

• 1:03Ben Gilbert?

  And we are your hosts. This was so effing cool.

• 1:10David Rosenthal?

  Kevin is so great. We had such a blast. Of course, we went deep. Covered the screensavers, the real origin story of Digg, the Digg Nation parties at South by the Ben you were at back in the day.

• 1:21Ben Gilbert?

  Totally. I wasn't expecting him to, he like corrected the record. All the previous Digg founding stories are wrong.

• 1:27David Rosenthal?

  No, Wikipedia is wrong, apparently.

• 1:29Ben Gilbert?

  Well, listeners, this episode basically has two chapters. We start in Web 2 and we end in Web 3. And obviously Kevin is super deep on all things crypto, blockchain, NFTs. And he's doing a really cool thing on the Modern Finance Podcast. And he even ends the show with announcing a new thing that he's doing. So stay tuned for that. But I had so much fun this episode, pattern matching everything Kevin learned from Web 2 to the Web 3 world. All right, listeners. Now is a great time to tell you about a longtime friend of the show, Vanta. AI has scrambled the whole security picture. It used to be that you proved that you were secure once a year on audit or a static PDF, then everyone would nod and you're done. But in an AI-first world, that doesn't hold up anymore.

• 2:14David Rosenthal?

  Yep. Your risk surface changes every week now. A vendor turns on an AI feature, or someone writes in a new model without telling IT, and your posture is different than it was last week, let alone at your last audit. Vanta's own research found that around 70% of companies have this quote-unquote "shadow AI" running with no security review at all.

• 2:35Ben Gilbert?

  Right. And that's where Vanta comes in. They're the leading agentic trust platform, meaning they've built the thing that closes the gap. And the way that they close that gap is Vanta Agent. Think of it as a GRC engineer, that's Governance, Risk and Compliance, except that it's software and it doesn't sleep. It finds the issues, drafts the fixes, and cuts the time that you'd spend on vendor assessments in half.

• 2:57David Rosenthal?

  In half! Which is exactly why more than 16,000 companies today run on Vanta. Companies like Ramp, Cursor, and Snowflake all stay audit-ready and catch the risks that crop up between audits across every vendor, every AI tool, the whole environment.

• 3:15Ben Gilbert?

  And that's the real value. Trust has to be continuous now, which is why Vanta automates your security, your compliance, and the work to earn and prove trust. We're huge fans of Vanta over here, and literally hundreds of Acquired listeners have become Vanta customers at their companies over the years. So you can get $1,000 off Vanta at vanta.com/acquired. That's V-A-N-T-A dot com slash acquired for $1,000 off, and just tell them that Ben and David sent you. All right, two last things. One, as usual, this is not investment advice from either us or Kevin. Do your own research. Come to your own conclusions on making your own investments. This is for entertainment and informational purposes only, as usual. Two, join us in

• 3:58Ben Gilbert?

  the Acquired Slack, acquired.fm/slash-slash. We are nearing the 10,000-person mark. It is a great group, and we'd love to have you. Now, onto our conversation with the one and only Kevin Rose. Kevin Rose, so great to be talking with you.

• 4:15Speaker 02

  Yeah, thanks for having me on the show. This is gonna be fun.

• 4:18Ben Gilbert?

  I think many, many episodes of my teenage years watching Dignation later, I feel probably the same way a lot of our listeners do when they run into David Nyer and they're like, "Oh, my God, you're like a real human." I feel very, very similarly talking to you today. So, thank you for all the just massive indulgence of nerdery over the years.

• 4:37Speaker 02

  Yeah, there is a bunch of nerd stuff there, a little comedy. Hopefully, I didn't convince you to start drinking at a young age because we were of legal age, but we did consume beers on each episode.

• 4:48Ben Gilbert?

  No, no.

• 4:49David Rosenthal?

  I was lucky. I actually started watching you on Screensavers when there was no alcohol involved. So, back when I was-

• 4:55Speaker 02

  Tech TV days.

• 4:56David Rosenthal?

  A middle school take. Yeah, Tech TV. Oh, we're gonna get into it.

• 4:59Ben Gilbert?

  Let's start because this is acquired way back. So, Kevin, I think we have it right. You grew up in Vegas, but your family's from Wisconsin, which is a state we've talked about recently with Marc Andreessen growing up there and Beeple on your show. What was that like?

• 5:16Speaker 02

  Yeah, you know, my earliest memories, I was born in Redding, California, but I don't remember it. And then I remember living in Oregon for a bit, which is where I am now in Portland. But we were living in a little town called Salem. And then when I was in second grade, we moved out to Las Vegas because there was just work there. That was like a place where my dad could find a job. And so, we moved out there. I kind of grew up thinking it was normal for, you know, 7-Elevens to have slot machines in them. Like, there was just a lot of things that Vegas does to you. And, you know, it was one of those things where I got geeky and got into computers and then quickly realized that the action, you know, really wasn't in Las Vegas.

• 6:00Speaker 02

  If you wanted to be in the hotel industry or work in gaming in some capacity, that was the place to be. But when I was around 18 or so, I kind of realized, "Well, I should probably think about moving someplace else, like Silicon Valley or, you know, someplace that had a bigger tech scene."

• 6:15David Rosenthal?

  I'm super curious, how did you figure that out? I felt the same way. I grew up in Pennsylvania, but I had no idea that Silicon Valley existed. Like, what was the process by which you like, learned that this was a thing? Cause like, there was no, you know, there's the internet, right? But like, it wasn't obvious in the way it is now.

• 6:32Speaker 02

  Yeah, so basically, when you started to get into computers back then, you're right. There wasn't like the internet where you could just go and figure all this stuff out. So I was on bulletin board systems and kind of dial up. And I remember going into computer stores and buying computer magazines, because that's what we did. Stay up with all the latest trends, you would just buy a magazine that was about computers, take it home and read about motherboards, right? So I just basically would hear about these conferences. And there was one called COMDEX, which was the world's largest computer convention. And it was held in Las Vegas. And so I was like, oh, I gotta go to this COMDEX thing, right?

• 7:09David Rosenthal?

  You're in high school at this point?

• 7:11Speaker 02

  Yeah, I was in early high school and I filled out a COMDEX application to go, because it was free, the passes were free, but you had to have a business. So I just made up a fake business name. I called it Foliage Software. And then I would apply and I received a badge in the mail. And I was like, okay, I'm going. And I talked my parents into driving me down to the convention center. This was before CES, or CES was very, much, much smaller back then. And I would go and just walk the aisles and look at all the different processors and motherboards and video cards and all the crazy, every big manufacturer had a kind of a block, a display there that you could go and walk up and try out all the new products. And it was like the coolest thing ever.

• 7:53David Rosenthal?

  And this was stuff that hadn't hit the market yet, right?

• 7:55Speaker 02

  Hadn't hit the market yet. It was brand new. And that's how I realized that all these companies were not based here. They were based, you know, most of them were kind of California, Silicon Valley based. But I was the youngest kid on the floor. Like, I had to kind of dress up. I put like a collared shirt on. And then it was funny because they noticed a couple of kids started coming and they banned, you had to be at least 16 to get in. And so the next year, I think I was 15 and I was like, oh, how am I going to prove that I'm 16? I think if someone asked me, I just told them I was 16. I had to have my birth date memorized for a year earlier. And then the next year, they made it so you had to be 18 to get in. And I was like, crap. And so they just kept moving the gold line. Yeah, exactly. A fake ID to get into a computer convention. So anyway, that was the early days.

• 8:38David Rosenthal?

  Oh my gosh. All these silicon companies that were like, all the companies were exhibiting at Comdex.

• 8:45Speaker 02

  Oh, yeah.

• 8:45David Rosenthal?

  Yeah, they're all based out in Silicon Valley. It was really Silicon Valley, but they weren't building fabs anymore. And so they could just move at such a faster pace. I remember this and it was like all this new product, all these chips, all these, you know, PCI plugins for motherboards. They were all hitting the market so fast. Oh, that was awesome.

• 9:02Speaker 02

  It was so exciting when you hear about a new clock speed come out, right? Like Intel would announce something and you're like, wow, a 66 megahertz processor. Or, you know, AMD would have out their new chip. And then, you know, you have the weird folks that were all like the deck alphas, like a completely different RISC versus CISC based processors. And that weren't compatible with Windows and they weren't compatible with, you're like, whoa, wait a second. What's this Unix thing? And it was just, it was a crazy time.

• 9:28David Rosenthal?

  Okay. So before we move on from Vegas, obviously you were dyed in the wool computer geek, sneaking into Comdex. That's amazing. Was there anything like sort of presaging your soon to be future career on, in front of the camera? Like, did you do like drama in high school? Like what?

• 9:46Speaker 02

  No, I think I was like the most shy kind of kid growing up and just didn't have a ton of friends in high school. And back then, I don't even know if this holds true today, but back then it was not cool to be into computers. And so you got made fun of a lot and didn't have a lot of friends. We were definitely not the popular kids in school and got picked on. And so it was not in my DNA to be, I didn't apply to work at Tech TV to be in front of the camera. I just wanted to be behind the scenes. And so I was like, kind of like setting up all the technical demos. And if they need a certain, you know, version of Linux installed, I would install that. And just like, you know, making sure that things were moving smoothly in that regard. So it was just by chance that, that I ended up on camera.

• 10:28Ben Gilbert?

  Yeah. Do you remember your sort of like break, like the moment where someone was like, hey, Kevin, you should be on air talent?

• 10:35Speaker 02

  Yeah, I mean, I had discovered a vulnerability in Windows that was a way to spam people using this kind of internal messaging tool. And so you could basically just send a message to any IP address and Windows would display it on the screen. And while it wasn't necessarily kind of a vulnerability in the sense of the person wasn't getting hacked, it was definitely a way to spam people. You could just write a little utility that would just go through IP addresses and deliver, you know, little notifications to their desktop. And so I told the host about it and they're like, well, you figured this out. You should come on and talk about it. And so they invited me on.

• 11:10David Rosenthal?

  Were Leo Laporte and Patrick Norton hosting at this point?

• 11:12Speaker 02

  Exactly. So Leo Laporte had me next to him and I was so nervous. I was just sweating and just like, and I went on and I kind of delivered it and explained it. And the executive producer, Paul Block, was like, hey, I like what you did there. Like, can you find more weird things to talk about that are not really known? And I was thinking like, well, I know a lot of these like hacking tools and stuff that I mess around with at night. Like, we could talk more about those types of things. And he was like, yeah, do more of that. And let's see how you do. And let's have you come on once a week and talk about a certain tool. So, you know, I look back and kind of cringe at some of that stuff because it was, you could just hear in my voice and the way I presented, especially in the earlier episodes, I just didn't, it wasn't in my DNA to be on camera.

• 11:55Speaker 02

  And actually, they sent me to a talent coach that would come in and record you and playback footage with you and make you watch yourself and talk about how you hold your hands. And like, there's these dedicated coaches that will teach you everything.

• 12:09Ben Gilbert?

  I did that once. I was at Microsoft and I was going to go speak on behalf of the company to a newspaper and they had me speak with a coach first and she videotaped, and I think it was like 5K for like two hours. Like, it was this exorbitant corporate markup. And she videotaped me for some of my talking points and then like made me watch it back while we were sitting there at the table. And it was the most painful experience.

• 12:33Speaker 02

  It helps a ton, though. I mean, it's a good, it's a good strategy, for sure.

• 12:37Ben Gilbert?

  Totally.

• 12:37David Rosenthal?

  You were the dark tipper on the show, right?

• 12:40Speaker 02

  That was the horrible nickname they gave me on the show. Yeah.

• 12:43David Rosenthal?

  Was that from that first episode? Did Leo just like riff that? Like, where did that come from?

• 12:47Speaker 02

  Well, we used to have these things called like Windows Tips and like, it was like a quick check-in. You're like, okay, when you're doing a segment, so everything in TV is broken into blocks. And so they'll have like the A block, which is the very beginning of the show, and they break it down into individual segments. There's a person keeping. Kind of a timer on, making sure when you're doing live TV, making sure the blocks don't go too long because it impacts other people's segments. And there's, it's very tight, well-oiled machine that has to run perfectly to pull off a live show. And so they had these little kickers that they would do, like when you finish a block, you bump out to a windows tip or a little, you know, 30 second, 45 second, one minute long max little tip. And so they're like, okay, well, we're gonna do, Kevin's gonna do tips that are about the dark side of the internet. Let's call

• 13:32Speaker 02

  them dark tips. And then they call me the dark tipper as a joke. And then it just kind of like was a funny little thing on the, on the show.

• 13:38David Rosenthal?

  That's so great. Skript Savers was live in front of a studio audience, right?

• 13:42Speaker 02

  Yeah.

• 13:43David Rosenthal?

  Were they like changing over the set while you were doing this on the, on the main segment?

• 13:47Speaker 02

  Well, the cool thing is that they could have basically, because the number of cameras they had and the locations on the set, you didn't have to do a lot of changing because there's always two locations to shoot. And so you would have like one off to the side and one primary like front location. And then even one of, all were in the nook where we took live calls. So there wasn't a lot of quick set change unless it was like a guest interview. And that was typically done between commercial breaks. We would go off to a commercial, you know, you have three minutes and change. And then they'd swap out, roll away the main center console and then, you know, put in a couple of chairs, get the guests seated, all the mics checked, all that good stuff. So it's a crazy thing because weird stuff breaks, you know, like a guest microphone goes out and

• 14:28Speaker 02

  somebody's running in 30 seconds before you come back on TV swapping out mics and like just demos break, computers reboot randomly, like weird stuff would happen and you just have to kind of roll with it. So that's the fun dynamic of live television.

• 14:41Ben Gilbert?

  David, we're so spoiled with acquired, like infinite retakes, just audio.

• 14:46David Rosenthal?

  I was literally thinking, I'm kind of jealous. Like that must've been such good trail. Like this explains like why you're so good because you had to just like roll with it. Whereas, yeah, we just, we've been doing this for six years, but like, we have so many luxuries, you know?

• 15:01Speaker 02

  Well, there's something nice about just being able to say, okay, screw it. Like if I mess up, like so be it. And we're done. Then you're done. You know what I mean? Like with my podcasts and stuff that I do now, it's like, I'm always going back and, you know, I'll listen to an episode that I think is really important. I want to make sure the editor got it right. And you're like, listening to it again. You're like, okay, we can trim a little bit here. And you know, it's like, you just walked out of the studio and you're like, okay, we're done for the day, on to the next day. So there was nothing you could do when it goes out.

• 15:26Ben Gilbert?

  You really can obsess for like a week, like until it is out there. And even after, Like you get any feedback that it was actually good. You're like, I just released something awful. Like this is just, I have this pit in the feeling of my stomach. I wish I had spent more time editing, even though I'm sure I just spent way too much cognitive load on this.

• 15:45Speaker 02

  Yeah. And you'll, you never know with your guests, right? Like you'll have a guest and you're like, okay, this is a very important person to have on the show for X, Y, or Z. And then you get them on and you're like, so tell me about your background. And they're like, it was great. And then they just like, stop talking and you're like, oh, come on. Like I gotta pull more out of you. This has to be entertaining, you know? So it can be challenging, you know, as someone doing the interviews to kind of get people to actually open up.

• 16:09Ben Gilbert?

  Totally. Well, because we're having that enormous problem here, I'm going to pry even deeper.

• 16:13Speaker 02

  Yeah.

• 16:14Ben Gilbert?

  So you did not move to the Bay area to work at Tech TV. You were, was your first job digital marketing for like an online furniture retailer?

• 16:23Speaker 02

  That's right. Yeah. So basically there was a company called Next Office that had hired me to come out and just really track all of their ad campaigns and ad spend. And so they had a marketing team that was going out and buying banner advertisements. And people would click on those and eventually lead all the way down to a checkout. And they wanted to know what the conversion rate was like and where they should be spending their money. And it wasn't ideal for me, but I knew at that point, I'm like, I'll take any job that gets me to the Bay area. Like, what can I do to get me out there? Cause it was the dot com boom, you know? I was reading about it in magazines and it was a crazy web 1.0 and just like insane valuations and parties. And like, just all the madness that you saw IPOs.

• 17:08Speaker 02

  And I was like, I gotta get out there. I gotta get out there, you know? So I just, I went online and I posted something on, I think like it was monster.com, like the jobs board. And, you know, Mike Mazer, who later became really good friends, reached out to me and was like, hey, I think you'd be great for this role. We had a phone interview and then they flew me out and gave me a job offer and I took it.

• 17:30David Rosenthal?

  Super cool. Do you recall how many years you were on Screensavers before the whole G4 seemingly debacle from the outside?

• 17:40Speaker 02

  Yeah, it wasn't that long, actually, because I think it was two and a half years that I was at Tech TV, which at that time, you know, it was the longest job I'd ever had and it was just, oh, it was so awesome.

• 17:53David Rosenthal?

  It seemed like it was a special place.

• 17:56Speaker 02

  A really special place. The majority of people were in their twenties that kind of like were around the set and hanging out. And we would all just party with each other afterwards and go out and we were all really close. We were just like a family and it's still even today, when I see those people, it felt like a very special time in our lives. And we just had no, kind of no idea what we were doing, but also we knew what we wanted to create. And it was a very creative group of people and the content was good. And Leo was like a great anchor host. He was a little bit older than us, but kind of brought everything together and had a great executive producer that was hilarious and fun to work for. And yeah, it was, it was awesome. And, but the problem with Tech TV is that we weren't as a network, really making that much money.

• 18:40David Rosenthal?

  It was indie, right? It was owned by Paul Allen?

• 18:43Speaker 02

  That's right. So Paul Allen owned it and he was pouring a lot of money into it to keep it alive. And it was an expensive network to operate. I mean, we had hundreds of people. And eventually they said, okay, I can't keep spending more money here. We need to actually do something and be acquired. And so G4, based out of LA, came along and said, we're a video game network. We think this is the future. We're going to acquire Tech TV more or less for the subs. So they, they bought Tech TV and they also thought it was a very similar audience and they didn't want to lose that because we had some shows, a couple of shows, Screensavers being one of them, that were getting decent ratings. So they're like, okay, how can we kind of bring that audience along?

• 19:23Speaker 02

  Merge it with our video game content. And so that's what happened. They bought us and they said, okay, by the way, we're going to shut down San Francisco. We're moving folks to LA. And so, you know, they gave me an offer to come down and continue to host the show down in Los Angeles. And so that's what I did.

• 19:38David Rosenthal?

  In retrospect, it seems so obviously silly because especially, I mean, even now, but at that point, the Bay Area was the center of everything that you guys were doing with Screensavers. To move it down to LA like, because G4 was owned by Comcast, right?

• 19:55Speaker 02

  That's right.

• 19:55David Rosenthal?

  Yeah, not to mention just the culture clash. That must have been rough.

• 19:59Speaker 02

  They knew it was really rough and they knew long term that they wanted to morph the screensavers into another show. And they weren't going to tell us that, but they knew that was the plan. So when I saw that was happening, that's not what I wanted to be long term. I didn't want to be an on air TV person. So for me, I, the kind of writing was on the wall that I needed to go do something else. And, you know, hopefully get back to the Bay area. And so it led me to right around when we created DIG. And then also I created a podcasting network called Revision 3. That was about creating that more of that type of content, like more geeky style content in podcast format.

• 20:37Ben Gilbert?

  Does Revision 3 predate the term podcast?

• 20:41Speaker 02

  Yes, yes, because we were doing video only and there was no way to do a feed of that. And so Steve Jobs had announced that there was something called podcasts that they were going to support. And build that into iTunes. And that's when Alex and I said, okay, let's get together and do a show called Dignation. Because now we have a place to distribute it.

• 21:04Ben Gilbert?

  At the risk of like being way too far down the rabbit hole of internet nostalgia. I seem to remember an opening jingle from Leo's shows that was like netcasts you love from people you trust.

• 21:17Speaker 02

  That's right.

• 21:18Ben Gilbert?

  Funny thinking that like netcasts almost became the thing.

• 21:21Speaker 02

  Yeah, he didn't want to use the word podcast and I'm not sure why that was. I think that he wanted to brand it his own thing. And yeah, that I don't think he had quite the momentum. It was, who was Adam Curry that coined the term podcasts? And I think that Leo was thinking at the time. And I believe this is accurate, that he was thinking that it shouldn't be just about Apple and about the iPod, because that's what podcasts kind of like, you know, referenced. Because Leo was always a big open source advocate and things like that. Yeah, that's so Leo. So Leo, like, how can we make this more broadly applicable? Which, yeah, that makes sense, but once the kind of snowball of the term podcasts grabbed hold, there was no going back.

• 22:07Ben Gilbert?

  Yeah, it's like, here I own zero iPods and listen to my podcasts on Spotify, who's actively suing Apple.

• 22:14Speaker 02

  Right.

• 22:15Ben Gilbert?

  Like, it stuck pretty hard.

• 22:17Speaker 02

  Yeah, totally. I always thought a lot of those terms were just hilarious. Like, the iPod, like, I, when you used to put I in front of things, it meant like internet.

• 22:26Ben Gilbert?

  Yeah.

• 22:27Speaker 02

  And so I always used to like to say these things out loud, just to hear how ridiculous they were. Like, sometimes I still tell people to send me electronic mail, because like, that's what E stood for in anything, you know? It's like, it's so funny when you like, actually pronounce them out loud.

• 22:41Ben Gilbert?

  It's amazing how long these things stick.

• 22:43Speaker 02

  Yeah.

• 22:44Ben Gilbert?

  All right, so thesis with revision three, though, like, there's a very clear, loud part of Twitter today talking about the creator economy and like, beating the drum that this is the next emergent thing. David and I feel like we've sort of experienced it firsthand. You've been experiencing it through multiple generations of the web. Did you have a thesis in starting that about the web and the internet is this new direct way to reach consumers?

• 23:12Speaker 02

  Yeah, absolutely. When we started revision three, the thinking there was that video was working online, like it was starting to take off and people could consume and watch video content. It was easy to produce on our side. Like, we could have some kind of mid-range cameras and gear and editor that we would just, you know, pay part-time. We could churn that out. And if we got enough people interested and excited, there would be brands that wanted to sponsor it. And that ended up being true. And so we had, you know, an ad sales team and... We had a network of shows and you know, revision three grew pretty quickly because people were starting to tune in and they, we found that niche audiences were quite large. And when they

• 23:56Speaker 02

  would talk to each other and use the internet to kind of share that this type of content was out there, we didn't have to rely upon these distribution agreements of these big old school television networks to get viewership. And we could actually measure it in a much more accurate way. And so that's what kind of started revision three. And yeah, that went on for many years and actually had a great outcome. It was sold to Discovery Networks for 35 million. And even though that sounds small these days, at the time, it was a big deal.

• 24:24Ben Gilbert?

  Yeah.

• 24:25Speaker 02

  And it became Discovery Networks kind of digital arm. Basically, they were all about, you know, traditional media. And so for them to get into digital is gave them a handful of folks that could come and lead that effort on the digital side. So it was pretty cool.

• 24:38Ben Gilbert?

  That's great. And so at what point did you realize the like flywheel effect of having a media stream with Dignation and other ways that you're reaching people and being the founder of DIG, like having this web 2.0 property?

• 24:54Speaker 02

  Yeah, it's a good question. When we started Dignation, we thought of it as a way to, because we had a base of people that really loved the dynamic that Alex and I had back when we were hosting the television show together. So when we started this, we were like, okay, here's a great way for us to talk about the stuff we would normally be talking about, which is like the geeky news, our favorite stories. I also happen to have the website DIG. And so it's a great way to surface the best stuff for us to be chatting about. And it became this kind of like way to engage the community and highlight their names. I had a top leaderboard back then on DIG. And as silly as it sounds like, it was, it was really, people loved seeing their name in lights,

• 25:36Speaker 02

  like, like, oh, Kevin and Alex mentioned me on the show. Like, that's, they mentioned one of the stories that I submitted. So it just led to more usage of the website. And yeah, they're right, there was this little kind of like flywheel that happened. And then eventually, at some point, DIG became much bigger than Dignation. Like, it was like, clear that there were so many people listening or watching and reading and consuming DIG. And Dignation still had a pretty niche following of the hardcore, original people. But that was totally fine with us. We were just having fun doing the show.

• 26:06Ben Gilbert?

  DIG was reaching, I think, what did it cap out at, like 38 million monthly uniques?

• 26:11Speaker 02

  That's right. Yeah.

• 26:13Ben Gilbert?

  Wild. I mean, at that point, that was an enormous audience to be reaching on the web.

• 26:18Speaker 02

  Yeah, it was pretty big. It was like top 10 web property and it's still pretty big. I would love to have another site that does 38 million.

• 26:28Ben Gilbert?

  Well, I guess like when I say at that time, like because Facebook now reaches, what, 3 billion monthly active users? I think if I have it right, you were out ahead of Facebook and Facebook hadn't really started becoming the juggernaut that it is until the sort of late 2000s. Uh, I think that was started in 2004. But at one point, didn't Mark come visit you when you rolled out the dig button that was like letting you upvote articles on their websites when they were thinking about the like button that is now sort of famous in everywhere?

• 26:58Speaker 02

  Yeah, that's right. Yeah. So we had a common investor, Greylock, and David Z, who was at Greylock, who's on our board and also on the board of Facebook, was like, hey, you guys should get together and did an email introduction and he's like, this is company Facebook. It's like really taking off. You guys should chat. And Dick had already kind of, it had taken off and gotten a ton of press. And so, yeah, Mark hit me up and he's like, hey, let's, you know, I'll come to the city because he was down in Palo Alto and he's like, I'll come to SF and love to see your offices and let's go grab some food. And so he came to the office and we chatted about kind of just what voting meant, you know, for us, it was voting on content was helping us service the best stuff and it was feeding back into our

• 27:41Speaker 02

  algorithm that would eventually recommend similar content to people that we had this like suggested stories portions where we had a couple, it was early kind of AI, machine learning type stuff that we were applying to articles. So if you like this, you might also enjoy these articles. And so, you know, Mark was really interested in that. And this is before they had the like button.

• 28:03Ben Gilbert?

  Pre news feed, I think even pre mini feed.

• 28:06Speaker 02

  Yeah, I don't remember what was going on at Facebook. It was locked down to just colleges and then they started opening it up and that's when I got an account. But yeah, he was very curious and yeah, it was nice. It was like Mark was a nice guy. Like, we ended up hanging out a handful of times and doing a handful of dinners and he was always just like a very thoughtful and, and even once, um, Facebook took off to the, it was clear that they were going to be much larger than Dig. You know, he was always really helpful. He was, he just said, if you ever, you know, need anything like shoot me a text, like happy to collaborate in different things. And, you know, he invited us into the early Facebook platform stuff.

• 28:45Speaker 02

  So we were like an early partner there when they first launched their platform. And yeah, I mean, I have nothing but good things to say about how we got to know each other.

• 28:54David Rosenthal?

  Okay. There's one question I gotta ask. We've seen it. It's been reported, but I don't think I've ever heard you talk about it. So supposedly the story goes, according to the media, you were inspired to start Dig to like make the leap and actually start this after you had lunch with somebody. Is that true?

• 29:13Speaker 02

  Are you talking about Commander Taco?

• 29:15David Rosenthal?

  Oh, no. The story I heard was you had lunch with Waz.

• 29:19Speaker 02

  Oh, no, it was not Waz.

• 29:20David Rosenthal?

  No. Oh, interesting. Okay. So this is from the Business Week story. Like we went, we read the story that was the, you know, the famous cover. And they reported there that you were inspired to start Dig because you had lunch with Waz and you were like, ah, I'm going to go be an entrepreneur.

• 29:34Speaker 02

  That's so funny. There's so many different, that's Sarah Lacy that wrote that story. That's funny.

• 29:40David Rosenthal?

  Yeah.

• 29:40Speaker 02

  This is the problem. Like, and this is so true with so many of my friends startups, like success has a thousand founders, like they say, or they used to say a very like a thousand fathers or whatever it was, but that's like not PC. So there is so many different lore stories, or there was even Wikipedia is completely wrong. So when I look at Wikipedia and the founding stuff there, it's completely wrong. It's just.

• 30:04David Rosenthal?

  Amazing.

• 30:05Speaker 02

  Yeah. So do you want me to just like cover the?

• 30:07Ben Gilbert?

  Actually, yeah, let's do it.

• 30:08David Rosenthal?

  Let's do it.

• 30:09Ben Gilbert?

  What is the like non-apocryphal, as you remember it, even if it's like a bland, the real, what happened?

• 30:16Speaker 02

  Well, this is the truth. This is exactly how it went down. And I don't know if I've ever told the full thing, but I'll just do the quick version of it. So basically what happened is there was a site out there called Delicious that was created by Joshua Schacter that was all about social bookmarking.

• 30:34Speaker 02

  And he would bookmark things and he would count the number of bookmarks on things. And this was one of the very first web two properties and it would surface interesting bookmarks. But it wasn't news because people didn't typically bookmark news. They would bookmark things that they wanted to return to later. And I would see that I was like, wow, it's servicing cool stuff here. I wonder what would this would look like if you applied it to everything. Okay. So that was one piece of it. The other piece of it was that I did have lunch, but it was with Commander Taco, who is the founder of Slashdot.

• 31:10David Rosenthal?

  Slashdot, yeah.

• 31:12Speaker 02

  And so he came and he was a guest on the show. And when I had lunch with him.

• 31:15Ben Gilbert?

  And this was on the screensavers?

• 31:17Speaker 02

  Uh, yes, but it was down in LA.

• 31:19Ben Gilbert?

  Okay.

• 31:19Speaker 02

  And so I had lunch with them. This is 2004, early, mid 2004. I asked him where all those user submissions went because Slashdot is great in that it promotes like their favorite stories to the front page. And they're all user submitted content, but you can't see any of it. So I was like, gosh, there has to be just so many good submitted stories here that they're just not surfacing. And I was like, why don't you make it? I literally told him, I was like, why don't you make it so we can see all the submissions? And then we can like vote up the best ones. And he's like, no, I don't want to do that, blah, blah, it's not the way it works. And so I was like, okay, well, I'm going to go build this.

• 31:51Ben Gilbert?

  Ah, this is like when Vitalik proposed the idea for a distributed world computer to David, who would?

• 31:57David Rosenthal?

  Oh, it was the colored coins and master coin, uh, the Israel Bitcoin two dot O projects. He was like, yo, guys, we should just do this all as one like master thing.

• 32:04Ben Gilbert?

  And they're like, no, we're not going to do that. And he's like, okay, cool. I'm going to go start something new.

• 32:09Speaker 02

  Yeah. I mean, that was basically what had happened here with Slashdot. As I said, well, I'm just going to go start something new then. And then I went out and I kind of basically just sketched it out. Like I sketched out what it would look like, what a dig button would feel like, what an upcoming section would be. Um, where submissions would go, like the whole thing. I found a freelance developer. I hired that freelance developer to create the first prototype. His name was Owen. It says on the website, he was a co-founder. That's not true. He was a freelance developer and, but you know, he's the closest thing I had to a co-founder because. We were in this together and he built it. It also says that Jay Adelson was a co-founder. That is not true. I hired Jay to be the CEO like four or five months later.

• 32:54Speaker 02

  It also says that Ron is a co-founder. Ron was my first technical kind of backend hire a few months later. So it's like, and I'm not claiming that these guys claim that. I'm just saying this is the way it was written. So I don't have any like ill will against any of these people. But like when people see who the first few people are, they call them all co-founders and all this thing gets written about who did this and that. And I'm just like, whatever. Like it's fine with me. I don't care that Wikipedia never gets corrected, but that is the origin story.

• 33:20David Rosenthal?

  Oh my God, that's so great. Well, and it gets so twisted because uh, so in the lore out there, like the having a guest on the show on the screensavers and then that leading to part of dig is out there, but it says that you had Jay on the show and then you brought him in, but it sounds like no, there was Commander Taco.

• 33:37Speaker 02

  No, Jay was on the screensavers and I met Jay through going out. He um, was one of the co-founders of a company called Equinix, which was a big data center company. And so, yeah, huge. And so I went out and met him through that. And then he, you know, about six months into, well, he really wanted to do revision three and he was the first check into revision three to create that content. And so that was awesome that Jay supported us back in that day. But he told me to get rid of dig. He thought it was a distraction to revision three. And he was like, oh, you should sell it. Like dude, just focus on revision three. This is our thing. I put money into this. Like we need to focus on this.

• 34:18Speaker 02

  And I was like, Jay, you don't understand. Dig is going to be big. It's growing. We can do both. And so eventually about three or four months later, Jay was like, oh, I see. Yeah, it is growing quite a bit. And I was like, hey, how about I give you some equity? Would you come on and run this? I don't know anything about raising from venture capitalists. I've never done it before. You've clearly been down this path. You've taken a company public. You can help out here. And so we agreed to, I gave him some equity, a few percentage points to the company. He then built out the right legal folks to work with, brought them on board. You know, I had formed the company using like one of these, like it was, there was no rocket lawyer at the time,

• 34:59Speaker 02

  but it was like a rocket lawyer-esque type, like thing. So the docs were all done wrong. I didn't have any like board meetings or meeting notes and like, it was all jacked up. So we had to have the docs all redone. And so Jay was very good at helping kind of correct a lot of my mistakes that I had made early on. But yeah, he didn't actually come on until like six or seven months later, after there was some real momentum there.

• 35:22Ben Gilbert?

  There's a thing that I've referenced and you've referenced here, which is web 2.0. What did that mean to you at the time?

• 35:29Speaker 02

  I didn't know. I didn't even know what it was called. Like I literally, Jason Calacanis came up to me, who had run Weblogs Inc., which was Engadget and a bunch of the other sites. He tried to buy Dig very early on. He saw that it was driving traffic to his sites. And he sat down with me at Sushi in LA. And this was after Dig started, it was very small. And he's like, I'll give you a million dollars for this. And then I was like, okay.

• 35:52Ben Gilbert?

  Classic lowball.

• 35:54David Rosenthal?

  So J Cal.

• 35:55Speaker 02

  Yeah. Well, honestly, I was like, okay. You know, I came from nothing, man. Like my parents had $0, as did I. And so I was like, yes, let's do that. And he sent me.

• 36:05David Rosenthal?

  And you've just been making a salary at Tech TV, right?

• 36:07Speaker 02

  Yeah, exactly.

• 36:07David Rosenthal?

  You didn't have equity in that.

• 36:08Speaker 02

  No, I had like $10,000 in savings and I'd spent a lot of it on building the prototype of Dig. And my girlfriend was pissed at me for that. And so basically, you know, he came in, but then there was like, he sent me a term sheet and it was like, you get 200K upfront. And then if you hit these milestones, you get like another 100K here. And it was like this really complicated. I was like, eh, I don't like this. Like we're growing a lot. And so ended up saying no and actually raising money instead. But he said to me during that lunch, he was like, you're like one of the biggest web 2.0 companies. And like literally, I thought, is there a software I need to upgrade on my servers that makes me web 2.0? I was like, there's something I'm not aware of. I need to upgrade because I'm not web 2.0.

• 36:51Speaker 02

  I did not do that upgrade. Like I had never heard that term before.

• 36:54Ben Gilbert?

  Which is so fascinating because to me, and maybe it was a couple of years later, Dig was the embodiment of web 2.0. It was dynamic content. It was Ajax. It was user submitted content. It was what became social media.

• 37:07Speaker 02

  Oh dude, after I found out what it was, I was like, of course I'm web 2.0.

• 37:11Ben Gilbert?

  Yes.

• 37:11Speaker 02

  Yes, of course we are.

• 37:12David Rosenthal?

  I invented this stuff.

• 37:13Speaker 02

  I had no idea what it was.

• 37:15Ben Gilbert?

  Well, it's this amazing thing that like, I think the people who are the deepest in a thing that's becoming a thing in the world, aren't the people who get to name it, which is the most fascinating thing. Like when we were interviewing Vlad from Webflow, he was like, oh, I found out like two years ago that we were a no-code company, but like, our company is 11 years old, so good to know about this no-code thing. And now, of course, they like have embraced it and have the no-code conference and all this stuff.

• 37:41David Rosenthal?

  It's so cool. I mean, on your show, like you're having all these awesome NFT artists on, and I feel like that's their story, right? Like that, like people, like everybody, they're like, yeah, I don't know. Like I'm just making my art.

• 37:53Speaker 02

  Yeah, it is one of those things that almost everyone, a lot of entrepreneurs that I meet, it's a dirty secret. It's like you go back and you look at these different covers of magazines and then this great success and like, no one really has a clue that they're ever going to be as big as they become. When you talk to the top companies that are out there, it's always like, this should exist. I'm going to go build it, but it's 99% of the time, it's quite shocking that it gets as big as, you don't really plan that. It was kind of like, I remember when Uber first came out, it's like, oh, how many people are going to get into other people's strangers' cars? Oh, okay. I guess it'll work for black cars. It'll work for black cars. That's what it'll be. And that, and that was the launch. The plan was like black car service, like with an app.

• 38:33Speaker 02

  Like never did the founders ever dream it was going to be applied to a random Toyota Corolla. You know, like it just, that was never imagined that you would feel comfortable.

• 38:43David Rosenthal?

  Well, you, you must have known Garrett from this whole

• 38:46Speaker 02

  Oh, yeah.

• 38:46David Rosenthal?

  Era, right?

• 38:47Speaker 02

  Garrett and I were really good friends and he had created StumbleUpon and we didn't see each other as competitive really. So we had always go, Garrett and I just like, we're really close in the, in the web 2.0 days and we would just go have beers all the time and talk about features and, and building out some of this stuff. But then, uh, yeah, I later ended up dating his ex-girlfriend and, and then we kind of added a little, that didn't go over so well, but we're, we're, we're cool now.

• 39:13David Rosenthal?

  That's why J Cal invested in Uber and Angel invested in Uber and you didn't?

• 39:16Speaker 02

  That would be a big reason why I didn't invest in Uber.

• 39:21Speaker 02

  But we're, we're good now. It's like the dumb, dumb shit you do in your twenties, you know? It's like, it was, it was such a small thing though. Like you gotta remember that web 2.0 and you know, this whole world, it really isn't as big as startup scene as it is today. And so when we would go meet up at a bar, we'd say, okay, okay, Flybar and Dividadero and, and SF, let's go hang out, let's grab some beers. It was easy to grab Garrett from StumbleUpon and, you know, get Josh Hechter from Delicious to show up to something or, you know, Ev from Twitter, whatever. Like we would just all hang, you know? So it wasn't like, we never knew that these projects were going to be that big. We were just having fun building software.

• 40:02Ben Gilbert?

  Meanwhile, let me just insert a midpoint. So today, tech is like the five biggest companies in the world. And Kevin, you're describing this era where like, basically all the people that run a lot of those big companies or started them or were involved in the founding or were angel investors are like hanging out, getting beers. There's this interesting midpoint that I remember viscerally where I went to South by Southwest and I want to say 2011 and you and Alex were doing a live dignation at Stubbs BBQ, huge sort of like outdoor, like great barbecue, but like concert venue and

• 40:37Speaker 02

  4,000 people.

• 40:38Ben Gilbert?

  It was huge. And I'm pretty sure after you did the show, the Foo Fighters played.

• 40:44Speaker 02

  Was it the Foo Fighters? Yeah, I think you, no, it was a big band, though. I was it the Foo Fighters? I don't, I wasn't a fan of the Foo Fighters, so maybe it was, but I remember there was a big band we had play one year that I was just kind of like, I don't know. I wasn't a huge fan and everyone was, thought it was a big deal. And then we had the Walkman play another year, which I was a huge fan of. And so that was awesome. I stuck around for that one. I was like, oh, this is really cool. But yeah, that, well, that was the cool thing about South by, right? Is you had these big bands coming in because they would play music the next week. And they'd come into town early and it was easy to book someone. Like I remember Snoop Dogg was going and doing different South by things because he was going to be out there anyway for the following music week or whatever.

• 41:26Speaker 02

  So it was easy to get a big name to come play your little gathering.

• 41:30Ben Gilbert?

  That makes sense.

• 41:31Speaker 02

  Podcast live show. Yeah.

• 41:33Ben Gilbert?

  It's still definitely accomplished this feeling, though, of me feeling like as someone who was totally following this all from the outside, because I was in high school and early college in like oh, five to oh, nine and feeling like there's a bunch of insiders and I'm not part of the insiders, but like they're like spitting distance away where like when I grow up, I want to be like one of them. That dignation moment where I was looking around at South by, I was like, oh, this is like pretty mainstream. This has become a part of culture.

• 42:04Speaker 02

  Dude, it shocked us all. Literally, we booked that venue and I'm like, I hope it looks like there's enough people here. Otherwise this is going to be a little awkward. We had no idea that that many people would show up and it was crazy because I brought my dad out to that show. And my dad had really no clue. I mean, he'd seen that we did these live dignations and, and I kind of hid it from him because he didn't like me swearing a lot, even though he swore. So it was just like, what, like, you know, I think he'd be cool with it today if he was still around. But anyway, he saw that show and saw all those people. And then when we left the venue, you know, all these people were back in the day, trying to come up and get my autograph and all that stuff. And like they kind of followed me out to the car that we were getting into,

• 42:50Speaker 02

  which was just crazy because I was like a geek and to have that kind of treatment was odd. But my dad saw all that and he, my dad was just blown away. And he ended up passing away two years later. I remember just being like, you know, it was a special moment for me because we didn't have a whole lot growing up. And my dad was really proud. I'm just really glad I had that. Cause I didn't, I didn't,

• 43:12Ben Gilbert?

  I bet.

• 43:13Speaker 02

  I decided to fly him out. I didn't know whether I should or not. And I, and I was like, okay, I should fly my dad out because he should be part of this. And, and it was just like, it was the right call. Those are very special moments for me, for sure.

• 43:24Ben Gilbert?

  I bet. There's an interesting like, looking backwards moment there where that probably applies universally. It's almost always the right call. If you're like, should I do something that overextends myself financially? Or is, you know, an inconvenience or something to have a family member come see something that could be special? It's almost always the right thing to say yes.

• 43:47Speaker 02

  Yeah. And experiences I would say are definitely like the number one thing to invest in, like they're the best money spent.

• 43:53Ben Gilbert?

  All right, listeners. Now is a great time to thank our longtime friend of the show, ServiceNow. If you are running a large enterprise, AI agents are likely spread across every team and deploying them is no longer the hard part.

• 44:07David Rosenthal?

  Yeah. The hard part is knowing what permissions they have, what employees are using them for, or what decisions AI is making. AI security for an enterprise at scale is not a small concern. Like the risks are real.

• 44:21Ben Gilbert?

  Exactly. And the challenge with AI is governing it, securing it, measuring it, and making sure that it actually delivers value. That is why ServiceNow built the AI Control Tower.

• 44:31David Rosenthal?

  Yep. AI Control Tower gives enterprises a single place to see, manage, govern, and optimize AI across the entire business. And it works with any AI, not just theirs. Every device on your network, every permission across every system, every AI agent visible and secure in one place.

• 44:49Ben Gilbert?

  And ServiceNow can do this because they've spent more than 20 years building the operational backbone of the enterprise. The workflows, governance, approvals, security controls, and institutional knowledge that power how work actually gets done across IT, HR, customer service, finance, and security.

• 45:05David Rosenthal?

  ServiceNow already runs more than 100 billion workflows annually and trillions of transactions for more than 85% of the Fortune 500. So when companies need a place to govern AI at enterprise scale, they're building on a platform at the center of how their business already operates.

• 45:21Ben Gilbert?

  And in a future that isn't going to be one AI, it's going to be thousands of AI agents working across every function of the company. But the question is, who's managing them all?

• 45:31David Rosenthal?

  So if you're trying to turn AI ambition into real business outcomes and make it work safely, securely at scale, go check out servicenow.com/acquired and tell them that Ben and David sent you.

• 45:42Ben Gilbert?

  Well, gosh, I could do this absolutely forever. I do want to talk about some Web 3 stuff. And I want to make the point, and I think we have a little interlude in the middle where I want to talk about before you became MoFi Kevin, but after DIG, there's some interesting chapters in there. A lot of the things that you're observing about that era feel similar to what's going on in crypto right now. Like, it's kind of the true believers. It's kind of everybody knows each other. There seems to be a lot of like real, genuine information sharing and just like belief in a common purpose, even though everyone kind of interprets the purpose differently. Does it feel like that to you, too?

• 46:24Speaker 02

  It does, yeah. I would say this is the first time since Web 2 where I've felt that type of connection and camaraderie around a new technology that the mainstream has yet to embrace, is starting to embrace, but has yet to embrace. And we're all early and we all see it and we all believe in it and it's just a matter of time.

• 46:46Ben Gilbert?

  Yeah.

• 46:47Speaker 02

  Time creates confidence.

• 46:49Ben Gilbert?

  It's interesting you feel like it's the first time since then because you look at like all these theoretical waves since then that like the media and VCs were sort of calling the next big thing, some of which sort of have been, you know, machine learning is, you know, a reasonable one. And like, obviously, there was the mobile wave after the sort of social wave.

• 47:09Speaker 02

  But the mobile wave felt like a kind of land grab. It was very obvious, you know, the mobile wave was something where when the iPhone came out, everyone's like, oh, of course this is going to be huge. There was no doubt, you know, and it hit consumers' hands immediately, right? And so there was none of this, you have to believe. It just, it was a given.

• 47:29David Rosenthal?

  Well, it was also just, it was an expansion of the existing web 2.0 market, really, right? Like Instagram was Flickr, right? Like WhatsApp was, you know, AIM. Like it's not a, the analogies were one to one.

• 47:42Speaker 02

  Right. And then, and then the big players were like, okay, we'll just make apps. Like Facebook made a mobile app and like Twitter made a mobile app. And like, that was just an easy kind of transition for them. And, and web three is very much like web two. When web two first came out, people were like, I don't know if this is going to be big. What are these social network things about? Am I really going to show people what I'm into by voting on things? Like, there was a lot of like, just, I don't know that I believe this to be true. And that's the same thing that's happening in web three now. Like, does this crypto thing real? Is it really going to scale? Are these NFTs really collectible? Is it just people, you know, making up stuff? And, you know, there's a lot of doubt there. So I, that's, that's the kind of excitement. Cause I love, there's an excitement that you get when you see something early that you believe to be true. But everyone else disagrees with you.

• 48:27Speaker 02

  That's always kind of fun.

• 48:28David Rosenthal?

  And there's so many more entrepreneurs, like we said, like, you know, NFT artists, entrepreneurs, DeFi projects where like, they're building stuff because they're like, oh, I'm in this community. This needs to exist.

• 48:38Speaker 02

  Right.

• 48:38David Rosenthal?

  Not like, hey, I've got this business plan and there's this obvious, you know, seem I'm going to go attack.

• 48:44Speaker 02

  It's true, where I'm a partner over there. We don't invest in business plans. We sit down with an entrepreneur, we listen to their idea. We want it to be new, novel, exciting. And if it works, it should be massive. And that's what we get excited about. We want to back incredible people building very ambitious things.

• 49:00David Rosenthal?

  Okay. So let's talk about, kind of during this transitionary period. What was your journey like in crypto? Like, when did you first hear about it? When did you buy your first Bitcoin? Like, how did we go from the end of DIG to MoFi?

• 49:15Speaker 02

  It's a great question. I'd have to go back and search Twitter. I think I first tweeted about Bitcoin in 2012.

• 49:23Ben Gilbert?

  Have you ever searched your Gmail to try and figure out? You can use like the before search operator. This is kind of a fun thing to do. It's like, open your personal Gmail, search Bitcoin or crypto, and figure out what the very first mention of it is in an email exchange.

• 49:39Speaker 02

  Oh, that's interesting. The question is, yeah, I guess I would have had that in, I had never even thought to do that. I mean, can we stop down for a second? Why do that real quick?

• 49:47David Rosenthal?

  Yeah, let's do it.

• 49:48Speaker 02

  Let's see here. So the first email I have about Bitcoin is June 12th of 2011. And it's an angel investor business plan. Andre from Canada says he likes Dignation and Foundation and wanted to tell me about this idea around Bitcoin.

• 50:08Speaker 02

  That is the first time that I actually see it mentioned in my inbox. And then the first Coinbase transaction I have is from, okay, yeah. So I apparently I tweeted out my Coinbase link to get referrals and they were sending me on Tuesday, August 14th of 2012, I started receiving a 10th of a Bitcoin, 0.1 Bitcoin.

• 50:39David Rosenthal?

  Oh my God.

• 50:40Speaker 02

  Which is, this is what it says, "Hi Kevin Rose, Coinbase has sent you 0.10 BTC worth $1.13 USD using Coinbase."

• 50:49David Rosenthal?

  Hell yeah.

• 50:50Speaker 02

  "Congratulations, your friend," and then there's the email address, "has verified their account on Coinbase. We've credited you 0.1 BTC to your account." And so I started getting a quarter of a Bitcoin and then I have just like dozens and dozens of those emails worth a dollar 16 if it was a quarter. So yeah, Bitcoin was pretty cheap back then. And that, so that means that I had a Coinbase account back in mid 2012.

• 51:15David Rosenthal?

  Okay, awesome. We're going to get back to Coinbase in one sec, but we gotta have one little digression. You mentioned Foundation. It's Trent Reznor, right? Is the music in the beginning.

• 51:25Speaker 02

  Yeah, yeah, the starting music on Foundation. Yeah, that's another, another little show I did where I interviewed entrepreneurs.

• 51:31David Rosenthal?

  Okay, how did you get Trent Reznor music?

• 51:33Speaker 02

  Well, he released that as a complete open source and he got rid of all the rights.

• 51:38Ben Gilbert?

  All the stems, right?

• 51:39Speaker 02

  Even the tracks. So he had one album where he just released the entire thing to be used for any purpose. And we were doing, I don't know if he had commercial, I don't think he would have said commercial rights in there, but we were non-commercial, we weren't putting any ads in or anything. So we used that. I had a chance to go and visit Trent at his house because we had him on for, we used to do- Do these before they were ask me any things. We did these things called dig dialogues where people could vote up their favorite questions for people they ask. And so we have the community vote up their top questions for Trent Reznor. And then I went and interviewed Trent and, and that was, that was a ton of fun.

• 52:13David Rosenthal?

  Oh, that's so awesome.

• 52:14Ben Gilbert?

  I like love searching old tweets and old emails. As you can tell, in preparing for this episode, I, I think the first time I tweeted about dig was a link to the dig dialogue with you and, and Trent.

• 52:26Speaker 02

  Oh, that's awesome. Yeah, that was, that was so much fun to do that show with him. His house is crazy. He's like the most rock star coolest house ever. Like it's all dark and like leathery and cool looking dogs. Everything about his house is cool.

• 52:40Ben Gilbert?

  He's such a pure artist.

• 52:42Speaker 02

  Yeah. Yeah. Well, it's crazy. I was like, we were chatting and we're talking about like all this different stuff and we were walking out and he's like, do you want to see my recording studio? Like, cause he's got one in his house.

• 52:52David Rosenthal?

  You're like, no, I gotta go.

• 52:54Speaker 02

  Yeah, yeah, exactly. Like in my mind, I'm like, you don't understand. Like my high school years were all about nine inch nails and like some, that was my favorite music. And, and so I was like, that kind of nonchalantly, I was like, it's like, yeah, you've got time. I'll check out your recording studio. And so we like just walked down there and it's exactly what you'd expect. It's like you walk into this room. It's all soundproofed and it's like racks of old analog equipment with like wires going between them, like a mad scientist like room. To be a fly on the wall in this room. It's just so cool.

• 53:28Ben Gilbert?

  Like he's creating all this music with real analog electric signals running through. Yeah.

• 53:34David Rosenthal?

  Yeah. Which is how all those guys used to do it. Like Fat Boy Slim and like, there are a bunch of great documentaries out there about that era now where like it wasn't, it was digital, but it wasn't like, like the source was analog.

• 53:46Speaker 02

  Right. Exactly. I love it.

• 53:49Ben Gilbert?

  All right, Kevin, bringing us back. I found your first three tweets with Bitcoin in it. In June 2011, you tweeted, testing out Bitcoin. Can someone send a couple cents to this address? Thanks. And then you have a wallet address.

• 54:02Speaker 02

  Yeah, that address I lost the keys for. So you can look up that wallet address and I think there's over a Bitcoin in there or something like that. So there's like, whatever the prices are, lost 50 grand or something.

• 54:12Ben Gilbert?

  You and everyone else, man.

• 54:14Speaker 02

  Yeah, I'll never recover that. If you pull up that tweet, please do not send any more Bitcoin transgression.

• 54:21Ben Gilbert?

  Second one, for those asking about Bitcoin, this is also in June. More info here. We use coins.com. Still haven't got any coins. Must be doing something wrong.

• 54:30Speaker 02

  I was started mining, I think, back then.

• 54:32Ben Gilbert?

  Oh, and then here it is, the big one, 2012. Playing around with Coinbase, a new startup that hosts your Bitcoin wallet. Check it.

• 54:41Speaker 02

  Yeah, so that I was, Brian, I had him on foundation, Armstrong, the founder, and he, I saw him at demo day at YC and I told him I wanted to invest and I was investing at Google Ventures at the time. And so I was a partner over Google Ventures. I brought that to the Google Ventures team. I won't call it any partner in particular, but let's just say one partner who I absolutely adore, and I'm not going to call them out, but if you hear this, I adore you, called it tulips and basically said that, you know, we can't, the fear, and this is a valid fear back then. And so I'm not slamming this person. You

• 55:22Speaker 02

  have Google corporates money. What if you invest Google corporates money into something that becomes or is called a scam later down the road? That does not look good for Google.

• 55:32Ben Gilbert?

  Ooh, this is like a great argument against corporate venture because like that is basically what venture capital needs to do in consumer.

• 55:38Speaker 02

  Right. So it's okay. I ended up investing in Coinbase a little bit later personally. That's, it all worked out, but Brian's an awesome human. We got him some great early exposure through that foundation and I just am delighted that we helped get that company off the ground because I know that foundation episode, he told me later, really recently, like maybe like three or four months ago, he told me that people still refer to that foundation episode where he was on as like the first time they actually got into crypto. So we got a lot of people on board into cryptocurrency with that. And at the end of the day. That is the thing that gets me excited about doing the foundation podcasts, about doing podcasts around finance. The reason I don't take sponsors and I don't try to monetize this stuff is like, that's not what it's about for me at this point in the stage of my career.

• 56:23Speaker 02

  It's about getting more people on board and excited about these new and upcoming technologies and hopefully helping them avoid a lot of the crap that's out there. Cause with, where anytime there's money involved, there's people that are trying to scam and take advantage of others. And I want to put out content because there's a lot of that other content out there. You know, there's a lot of people on crypto Twitter, not the groups that I run in, but if you just go a layer or two deeper, you'll see so much shilling and flipping and trying to like pump and dump. And like, that's the stuff we need to get rid of.

• 56:54Ben Gilbert?

  Do you have any hot takes on something that has a large user base, but you feel is pretty scammy?

• 57:03Speaker 02

  Well, I would say that it depends on what the goal of the project is. Like there's a lot of knockoff projects that happen, like Dogecoin, for example, when it first got started, I had Jackson Palmer, the founder on my podcast as well on foundation. And it was meant to be a cryptocurrency that could be used as a way to more or less give away for good deeds. So people were using it to kind of tip. There was all these Dogecoin tipping bots and Reddit.

• 57:34David Rosenthal?

  Vitalik got a ton of Doge.

• 57:36Speaker 02

  Yeah. I mean, if people were like, back in the Reddit days of when Doge first launched, people were using the tip bots and they would send, you know, a thousand Doge here, like 2,000 here. Oh, that was a great comment. Here's 50 Doge. And so that's why the supply was so large is they, he wanted to create this enormous supply. So it wouldn't be hoarded and it would just be thought of this fun thing to kind of like create this little tipping economy. And I thought that was a really cool idea and one that was worth playing around with. Now, there is a lot of knockoffs and clones of that with not the intention of pushing technology forward in any meaningful way,

• 58:15Speaker 02

  but with just the intention of price appreciation, because they want to jump on, ride it, sell it, make money and rinse and repeat. And you see that happening over and over. So those are the projects that I think are to be avoided. You know, I certainly believe that Doge did not have that intent. I know that they didn't have that intention when they launched. It was not a pump and dump scheme. It was just like, let's have fun with this and see where it takes us. And that was the thinking there.

• 58:42Ben Gilbert?

  It makes total sense. I mean, anytime there's a new paradigm or a new opportunity, let's just phrase it as new paradigm. Everyone's mindset has to shift to become a believer in the new thing. Look at Web 2. The easiest thing to do would be to say like, no, why would I submit stories that other people could see?

• 59:04Speaker 02

  Or even worse, I mean, I remember my parents, Ben, I'm sure you remember this being like, don't put your personal information on the internet. Like, don't join Facebook.

• 59:12Ben Gilbert?

  Which it turns out may actually be pretty good advice. I should be more succinct. Anytime there's a paradigm shift, it requires a leap of faith to become a true believer in the new thing. And the earliest people that have to do that, there's the most upside for them because they get to be early to that thing which could accrue them reputation or actual, you know, shares in whatever the new thing is. But it requires that leap. And so it's really easy when you are someone who's looking around and seeing other people become awakened to this new thing to have some shyster convince you that, oh, you should just become awakened to my new thing too. That looks a lot like the legit awakening that's going on with other people that's paying big dividends for them.

• 59:54Speaker 02

  Right. And I get that. I think that you have to ask your question, and this is happening in the NFT spaces as well. You have to ask the question, like, what are the real motivations of this project? And so I will certainly miss some things that start off as a joke and eventually have real legs to them and evolve into a place where they are innovating in some interesting capacity that means multi-billion dollar kind of ideas out of a joke, right? Like, that will happen. Communities will form and they will evolve and make something that is more than just that initial kind of hype cycle that happens, we see a lot of. But for me, when I evaluate new cryptocurrency projects, I always look through

• 1:00:40Speaker 02

  The lens of one, is there a use case here that needs to be solved that this company is going out and solving? Is it a credible team behind it? And is there a discussion of price appreciation? Is that the main topic? Because the easiest way to see through a scam is to look, what are people talking about? Are people talking about the mooning of the coin, the price going up? Or are they talking about why the underlying technology and what is being built is so important for the future of the world? And if the conversation is around making money, there's a good chance you're in something that is going to be some type of pump and dump, or eventually just has the bottom fall out from underneath it. So, you know, that's how I try to evaluate things.

• 1:01:22Speaker 02

  And it's a part of why I want to start focusing and having more NFT related content is because there's a lot of that happening in the NFT spaces as well now. It's like anyone armed with Photoshop can instantly churn out 10,000 characters with different glasses and hats and goggles and all that other stuff, right? And people, they call it aping into something where you just kind of go all in. People see this and they ape into something and, you know, a community can be built around that and you can have some serious growth there. But I worry about the long-term durability of these projects. Like, is there going to be so many of them that they just seem all like kind of copycats and clones?

• 1:02:03Speaker 02

  And so for me, that means I'm very selective about which investments I place there. And I do consider them investments.

• 1:02:11Ben Gilbert?

  You're talking about when you personally buy an NFT?

• 1:02:13Speaker 02

  Right, exactly. An NFT or a cryptocurrency. But when I personally buy an NFT, I'll say first and foremost, well, what's the price point? The price point is hundreds of dollars and it's something that, you know, you could afford to lose if you had to. Then I want to love the art. You know, I bought some cool cats like a few weeks ago. It wasn't because I thought cool cats were going to be the next CryptoPunks. I just thought they were cute little characters and I liked to swap out my avatar from time to time, right? And they had a great community that was following them and they had plans to launch other little cool cats related things. And I'm like, this is a fun little community. And so that is why I went in and bought a few of them at lower. Prices and I'm okay with losing that money because there's no money to be lost. I'll always consider them fun little things that I can put in a digital frame

• 1:02:57Speaker 02

  or have them up around my house and it kind of marks a moment in time when I thought that was cool. Right. So that's fine. Now, when it comes to spending like real dollars and like actually making an investment, then I'm looking for more blue chip related stuff. And so that is in my mind, projects that are not clones, but that were actually the first at something. Like, you know, the first fully on-chain generative artwork or, you know, CryptoPunks defining the ERC 721 standard and being the first to kind of put that out. Those are the projects I look at and saying, those will always historically look back and say, those were important for this space, if you believe in the NFT space.

• 1:03:39Speaker 02

  And I think they will have long-term collectability and durability from a price standpoint. So that's how I, I look at it when I'm buying those things.

• 1:03:47Ben Gilbert?

  It's funny, implicit in what you're saying is the very same reason why the founders of some new groundbreaking consumer thing always have way more upside than any investors or anyone who comes later. It's because they were true believers in the thing for the value of the thing, even before it had any notion of being an investment.

• 1:04:08Speaker 02

  That's right.

• 1:04:08Ben Gilbert?

  And that's why oftentimes anybody who's seeing a trend and saying, oh, I gotta get in on that. And they develop their business plan, just to use the same parlance that we used earlier. That's why there's always less opportunity there than for that, like initial core sort of like community where there's a lot of heat.

• 1:04:27Speaker 02

  Right.

• 1:04:28David Rosenthal?

  It also strikes me like, man, the parallels to modern art, right? Like, you know, anybody can make a knockoff painting of a Campbell's soup can or Marilyn Monroe, right? But nobody was doing that before Andy Warhol. It's just like such an obvious analogy here.

• 1:04:43Speaker 02

  Yeah, I mean, there's things on the NFT side that are first, you know, there's certainly some of the programmability that you can do on NFTs and what's coming there is really interesting. There are going to be new genres of art that are created, which is a very exciting thing. I mean, this idea of generative art, like what's happening with art blocks and that the user doesn't know what they're going to receive when they make a purchase for the first time and that, you know, that transaction hash is used as part of and fed into the algorithm that actually generates the art. I mean, that has never really been done before in a way that we could capture it and hold on to it. I mean, it could have been prototyped and done in a way that could be displayed, you know, a decade ago, but there was no way to like prove ownership.

• 1:05:25Speaker 02

  And so, yeah, there's some really cool things that I'm just seeing and I'm excited for the depth that is going to be coming to NFTs rather than it just being about a place to mint a JPG or a GIF. It's going to be, or I guess it's called GIF. I always get corrected when I say that. Oh, no, it's GIF. It's GIF. It's GIF. It's actually GIF. We had a whole debate on this. I know technically, but like. The developers that created it say it's GIF, like the peanut butter. So. The community has wrested control of this. Yeah, it's crazy. But anyway, yeah, so there's some really cool, you know, new thinking there that I'm excited to hopefully invest in. Were you into art before NFTs? Yeah, I have been for quite some time, not, not in a deep way, but it's something

• 1:06:09Speaker 02

  that as someone that has built a bunch of projects, I've always kind of been a usability, a feature and a branding kind of person. So, you know, everything that I've created is always been the names that I've come up with, logos, things like that, always worked very closely with designers on iterating and kind of refining. And so I'm someone that can appreciate it and, you know, I've, I've always been a big fan of certain artists, but yeah, this is just like a whole, whole new level, like these new digital first NFT artists like X Copy and some of the people that are just doing really bold, fun things. I just get really excited about.

• 1:06:46Ben Gilbert?

  I didn't realize it until now, but you're kind of the perfect person to really understand a lot of the value with NFTs because in a lot of ways, you're an artist yourself. You look at a lot of the products you've built that have always had really strong design sensibility or literally been, you know, in things like watches or, I mean, even the, the more recent apps you've built with fasting and it's called Oak, right?

• 1:07:09Speaker 02

  Yes, the meditation app.

• 1:07:11Ben Gilbert?

  Yeah, it's very clear that you have a strong point of view on how something should look and feel and be as an object to use. And also, you have this great investing lens at True and formerly at Google Ventures and doing all these incredible angel investments, having been a founder. And so it really is this fascinating sort of convergence of art and investing and the internet that is kind of like this, like Kevin Rose stew.

• 1:07:38Speaker 02

  I like that stew. It's a good stew. That's a great way to describe it. Yeah, those are all the things that I care about. And for me, that's what makes doing these types of podcasts like just a lot of fun. That's why I want to produce more of this type of content is I love chatting with these artists and these founders and these creatives that are doing new and exciting things and bringing that awareness to other people.

• 1:07:58Ben Gilbert?

  So how, I'm curious about that. How'd you get hooked up with True? Did you know Om from the?

• 1:08:02Speaker 02

  I knew Om from back in the day. Yeah. And he used to cover Dig a Lot when he was a writer. But True had actually backed and invested in my company Milk that I sold to Google Ventures. Then they went on to back Hodinkee and Zero. And so they've backed several of my companies. And so I just met them and just fell in love with the people there. I mean, they have a fantastic team of very low ego folks.

• 1:08:28Ben Gilbert?

  I love everyone at True. Anyone that I've worked with, I'm always, I always walk away feeling like, oh, that person has the longest view in the room, to use a Sam Hinky parlance of caring deeply about relationships above all else.

• 1:08:41Speaker 02

  I mean, that's it exactly. They're such long-term, long view kind of investors. We pride ourselves in trying to take all the pressure off the entrepreneur. You know, like we backed Matt Mullenweg from WordPress 15 years ago and we still have a board seat and we still have stock and we're not saying, hey, you have to go IPO or you have to sell. Like, that's not in our DNA. We want entrepreneurs to, it's their baby, it's their company. We're just, they invite us in for the ride. So it's like, who are we to go and try and force outcomes and do all the mean nasty things you read that other VCs can and have done in the past? And so I realized that working with True early on, you know, when I was going to sell to Google, it was going to make a tiny bit of money for the investors, but not world-changing money.

• 1:09:25Speaker 02

  And the partner I was working with was like, Kevin, this is your company. Do whatever you want, man. If you want to go sell it, then sell it. If you think the time is right, like, make it happen. And so it was just that kind of like. It just makes me, as an entrepreneur, you have so many things that you're trying to juggle on your head and wrestle with. And just knowing that your investors is not one of them is, is one of the reasons why I was attracted. I said, I have to work with this group. And so, yeah, that's how we got hooked up.

• 1:09:50Ben Gilbert?

  And you initially became a venture partner, right? And then transitioned into a full-time partner role?

• 1:09:56Speaker 02

  Yeah, I was a venture partner. So I was still building stuff. You know, I had built Zero and then we decided to bring that and Mike Mazur took that over as CEO and then we funded it true.

• 1:10:05Ben Gilbert?

  Wait, Mike Mazur, your first boss?

• 1:10:07Speaker 02

  Mike Mazur, the dude who hired you? Yeah.

• 1:10:10Ben Gilbert?

  That's awesome.

• 1:10:11Speaker 02

  Yeah, Mike and I just remained friends for a long time. So I hired him to work for me at DIG. He, he first hired me, then he left the office company, went and started working in Electronic Arts, was a VP over there, left EA, was a VP at AOL for a while, left there. And then I hired him to run marketing and BD at DIG.

• 1:10:34Ben Gilbert?

  Wow.

• 1:10:35Speaker 02

  And then, yeah, eventually, he's the one that got me into fasting because he had a bout with a really serious stage four cancer that he beat back and went into remission. And in conjunction with chemotherapy, he also implemented fasting. So he's a big believer. And so he took it over as CEO.

• 1:10:53Ben Gilbert?

  It's so cool.

• 1:10:54Speaker 02

  Oh, that's awesome.

• 1:10:55Ben Gilbert?

  Okay. So how did you make that call of, you know, sitting in that emotionally of, I'm a venture partner, so I'm helping to bring great entrepreneurs to the firm. It gives me lots of flexibility where I'm not, were you sitting on boards at that point?

• 1:11:08Speaker 02

  No.

• 1:11:09Ben Gilbert?

  So you're, you have time to sort of tinker and explore and start things and build and do media and transitioning into that, you know, full-time partner role to have investing be your day job. How did you make that call? And how was that felt?

• 1:11:22Speaker 02

  Yeah. Well, I will say I was sitting on boards, just not related to true. So I was on the board of Houdinki and Harlan Estate and the Tony Hawk Foundation and a few other things. But like, I was just, it was one of these things where building is a lot of work and it just, it is one of those things that you have to kind of go all in and give it your all. And so for me, We had just had our first kid and I was just at this point in my life where I realized that I didn't want to go and do another startup. So that's kind of the venture role thing is like you're trying to figure it out. Like, should I do another startup? Should we, should they fund me again? Should I go into this? And, and I thought, you know, I want, I want to optimize quality of life a little bit more. And so I was like, you

• 1:12:07Speaker 02

  know what? I think I'm going to come on and, and if they'd had me, I'd be an investor there. And they were like, yes, hell yeah, let's make it happen. And so I joined full time a couple of years ago and have been doing deals ever since.

• 1:12:19Ben Gilbert?

  That's really cool. Are you looking at crypto stuff in particular?

• 1:12:24Speaker 02

  Yeah, I would say that 95% of my day job is evaluating cryptocurrency or blockchain related companies, along with NFT related stuff. So, you know, we've probably deployed, if I had to guess, probably 75 million this year into blockchain related startups.

• 1:12:42Ben Gilbert?

  Wow.

• 1:12:43Speaker 02

  And so it's, it's a decent chunk. We have a 750 ish million dollar fund. So it's a big chunk of our fund.

• 1:12:49Ben Gilbert?

  Yeah, 10% of a fund in a particular industry is pretty heavy.

• 1:12:53Speaker 02

  Yeah, I mean, it's pretty well diversified in that that spreads across a whole slew of different protocols and coins and DeFi and scaling solutions and, you know, NFT projects and like a bunch of different things there. So, but yeah, we're, we're firm believers in the future of blockchain. There's no doubt that this technology is going to change everything, especially the financial and collectibles world and gaming as well.

• 1:13:16Ben Gilbert?

  All right, listeners. Now is a great time to talk about a new partner of ours here on Acquired, Lagora, the agentic operating system that is redefining how the world's best legal teams work.

• 1:13:29David Rosenthal?

  Yep. It's sort of obvious that AI is going to completely change the legal industry. I bet most of you listening have dropped a contract into some sort of AI chatbot out there. Lagora took that insight and asked the question, what if you really built something with that power from the ground up for the legal industry?

• 1:13:46Ben Gilbert?

  So the founders did exactly what great founders do, operate with obsessive customer focus. They embedded inside a massive law firm for months. They sat with the lawyers just watching how the work really gets done.

• 1:14:01David Rosenthal?

  And that's how you get features that customers love like tabular review, where you drop in a folder of hundreds of contracts and it pulls every key term into a grid a lawyer can actually work with. Legora's bet here is interesting. Since it lets each lawyer handle more complexity, any given person can increase the quality of their work and do higher value work. And this means that the pie can grow even as each individual task takes less time.

• 1:14:25Ben Gilbert?

  And they recently launched Legora Agent, offering greater intelligence and performance. The agent lets lawyers set an objective. Then it can handle the planning and the execution and delivery of the final product. Legal teams get to maintain full control and transparency since they're still involved where judgment is required.

• 1:14:44David Rosenthal?

  And Legora works where you already work. You can use it within Microsoft Word while redlining or drafting. The early Legora numbers essentially speak for themselves. When they have a head-to-head pilot with their top competitor, they win 70% of the time. Legora now has over 100,000 lawyers on the platform from 1,200 legal teams in 50 countries. And crazily, they went from 1 million to 100 million in ARR in about 18 months.

• 1:15:14Ben Gilbert?

  Truly insane numbers. And that is the real test. Plenty of things demo well, but the question is whether a busy associate actually reaches for it during crunch time, or whether a partner trusts it before going into a conversation with a major client. If your legal team wants to check it out, whether you're a law firm or you're in-house at a company, you can learn more at legora.com/acquired and just tell them that Ben and David sent you.

• 1:15:39David Rosenthal?

  Okay, so this brings us to, I think the perfect place to start to wrap here is, you know, MoFi. Obviously, I mean, I think you've explained throughout the whole thing why you're doing it, this whole conversation. Where does it go from here? You know, you could just keep doing what you're doing and it would be great. It's got magic. It's wonderful. But it's also like, it's all about crypto and web three. And it feels like there's also so much more that what used to be social media can become in, you know, web three world. Like, how are you thinking about it? Like, you could have a DAO, you could be doing all sorts of stuff.

• 1:16:12Speaker 02

  Yeah, it's a good question. And I think that- I'm starting to see kind of two individual worlds starting to separate a bit. So in some sense, you have traditional cryptocurrency scaling solutions and DeFi in one bucket. And then you have all the craziness that's happening with NFTs in another bucket. So I'm actually going to be launching a new podcast, if I don't already have enough podcasts, that is dedicated to all things NFTs.

• 1:16:42David Rosenthal?

  How cool.

• 1:16:43Speaker 02

  Just NFT content.

• 1:16:45David Rosenthal?

  Awesome.

• 1:16:45Speaker 02

  Yeah, it's going to be called Proof. So it's proof.xyz is the domain name.

• 1:16:50David Rosenthal?

  It's a great domain. Oh, that's awesome.

• 1:16:52Speaker 02

  Thank you. Um, yeah. So I'm excited. Proof is going to be just going really deep on all things NFTs. And that will cover, you know, everything from the art and programmable side of things to the generative side, to, you know, tokens that cover DAOs and what DAOs are doing to the gaming world and how NFTs unlock different assets and how people are buying virtual land as NFTs. We'll just cover it all there.

• 1:17:17David Rosenthal?

  Yeah.

• 1:17:17Speaker 02

  And then Modern Finance, the podcast, we'll still do on occasion, a little really important piece on NFTs. So like the, you won't miss it. The people that listen to that won't miss out on the, the big, deeper, like peoples of the world. Or when you have someone really big on that you want to get out there. But that will focus more on, on everything that's happening on DeFi and scaling and new coins and, and that, that world. So I just was getting a lot of, there was two camps. There's people saying, give me more NFT content. And then there's the other camp being like, hey, get back to some of that crypto stuff that we missed. And I'm like, I can't please everybody. So I got, I gotta break it.

• 1:17:52David Rosenthal?

  It's funny. We're getting that unacquired a little bit of like, hey, give me more of that, uh, you know, uh, Atari, like the classic tech history, or even just, you know, non crypto stuff. And people are like, give me more crypto stuff.

• 1:18:03Speaker 02

  Yeah. So it's, you, you know what I'm talking about. It's like, you can't, you can't please everybody. So for me, it's just easy to carve out a separate feed and, and say, listen, the best of the best from proof, like the big names will always make it to the main Modern Finance podcast. But if you want to hear about the new and upcoming artists that hasn't broken out yet, but I think is really cool because they're doing something unique and novel, you're going to find it on the Proof podcast. So it should be fun.

• 1:18:25David Rosenthal?

  Okay. So like nerd out a little bit. What's your strategy for launching? Are you going to have like, do the first couple of episodes of proof in the mofi feed and then spin it out?

• 1:18:33Speaker 02

  Yeah, most likely what I'm going to do is make an announcement. I have the CEO of SuperRare, which is one of the big NFT platforms that I just recorded. I'll announce it at the beginning of that episode when we drop it on mofi and then people can go subscribe. I'll probably backdate and put all of the NFT content that we have in mofi into the new feed. So if you come into that feed, people can always jump back in time and say, oh, I want to listen to that interview with Snow Fro, the founder of Art Blocks and they'll be able to jump back and hear that or hear when I interviewed the founder of CryptoPunks or whatever it may be. So it'll be pre-populated with probably five or six episodes. And then I'll start releasing a new NFT episode, hopefully every week to week and a half.

• 1:19:17Speaker 02

  And I would say probably one a month or so of those will make it to the main Modern Finance feed. And if you subscribe to both, you'll know you're like, oh, I already listened to that one. I don't need to click it on mofi. But then mofi will be more just like big name people in the crypto industry, both in terms of creators and then people that are analyzing it and where it's going. And so I want, you know, talking through where DeFi is, how it's evolving and some of the new and interesting projects and and more of that. So yeah, it's going to be a lot of work, but this is the stuff I love to do because I feel like both of these industries are filled with confusion, confusion and a lot of hype and a lot of, you know, back in the, remember the ICO world a few years ago, there were so many scammy projects there. And it's like,

• 1:19:59Speaker 02

  I hope that people can come in and know to trust me that I would not want to promote something that that is a scammer that is just there for the hype. But actually, you know, I will always call out why, why they're on the show and why I think it's worth covering, you know? So it won't be everything. It'll be a subset of what's out there.

• 1:20:17Ben Gilbert?

  I'm so glad you're doing this because I would say I've been a latecomer in almost everything in crypto. But I guess in some ways, all of us who are currently participating in the ecosystem are early adopters because there's going to be 10 to 100x more people after us. But I would say it took me listening to the Beeple episode and

• 1:20:36David Rosenthal?

  Which is so good, by the way. If you haven't listened to, oh my God, Beeple, what a character. I love that guy.

• 1:20:42Ben Gilbert?

  I just want his accent. Like I want his like manner of speech. It's so fun.

• 1:20:47Speaker 02

  Oh my God, he's the best. He's hilarious. I mean, you couldn't, it couldn't have happened to a nicer, crazier dude.

• 1:20:53Ben Gilbert?

  Truly. But it took me listening to that and several other of your NFT episodes for it to kind of click. When NFTs first started becoming buzzy, I was definitely one of those people that was like, the whole point of digital art is that it's infinitely reproducible. And like, why would I pay for something? I could view on Insta. I was definitely one of those people. And I think it took me till hearing people, first of all, learning about the artists behind the art is actually the value. Feeling close to those artists and why they're doing what they're doing, that is the reason to buy it, at least in my opinion. And sure, it's cool and it's fun to look at, but it was also the realization that he brought up of like,

• 1:21:33Ben Gilbert?

  people aren't buying NFTs. People finally have a vehicle to value digital artwork. And like, digital art has been a thing for like 10, 15, 20 years, kind of in this format, but there's been no incentive to make it since it's just infinitely replicable and easy to rip off. And finally, now there's like an incentive for artists to make incredibly cool stuff and rare stuff in a way that is totally driving the level of creativity and innovation here because there is actually now an incentive for it.

• 1:22:05Speaker 02

  Yeah, there's so many pieces that unpack. That is a major one. You nailed it. But then there's also just imagine we're sadly, you know, you say, I'm a little older than you guys. You guys are old too.

• 1:22:19Speaker 02

  There is a younger generation that grew up skinning their characters in games and are so used to purchasing and holding virtual objects and virtual goods. And there was a survey that was done that there is a very large subset of gamers that consider, it was like more than 50%, it was something really scary. They consider their online identity in their games to be more important than their offline, like in-person identity.

• 1:22:46Ben Gilbert?

  Wow.

• 1:22:46Speaker 02

  And so you have this world- Which actually makes total sense, like when you think about it. It makes total sense. And you have this world of people that have grown up digitally native that say, I want to be able to show my friends something cool on my phone that I own. And when they get older, they're gonna say, or flip it up on my wall and have it as something I can chill my wall. And guess what? If the house burns down, I don't lose my, my painting or I don't have to worry. For me, I think about when my kids walk by something, I don't have to worry about them taking a marker to it. You know, it's like, there's just so many beautiful aspects to the portability and how you can showcase your favorite pieces of art. And also just how you can unlock the potential, like when they're programmable.

• 1:23:30Speaker 02

  What if my art changes over time and the artist bakes in certain things that unlock it the longer I own it? Like some of that is just so cool. So there's so many aspects to this ecosystem that what NFTs brings to the table that you can't have with traditional art, that I think are going to take another decade or so for people to really wrap their head around. Do you know that back in the day, so when people moved from when Canvas was created, do you know that there was a huge blowback on it?

• 1:23:58David Rosenthal?

  No.

• 1:23:59Speaker 02

  So yeah, there's a huge blowback on Canvas because everything was painted on walls or on these like wooden.

• 1:24:04David Rosenthal?

  Yeah, frescoes.

• 1:24:05Speaker 02

  Yeah. So to move to Canvas, many people thought during that time, it's portable. Why wouldn't you want something permanent? It's like it can be taken and copied. Like there was all these like worries around moving. So a lot of Canvas art was actually worth less than things that were actually in a more permanent, you know, on the wood or on the, on the wall. So it was just like this transition that happened and it took a while for people to finally adopt Canvas.

• 1:24:32David Rosenthal?

  Amazing.

• 1:24:32Speaker 02

  I just thought that was a hilarious story and like the same thing's happening here, you know?

• 1:24:37David Rosenthal?

  Oh man, that's so cool.

• 1:24:38Speaker 02

  I just love that, like there's something really cool about being able to walk into a gallery or a bar or wherever you are, see something on the wall and being like, wow, that artist really connects with me. Oh, it's $700 worth of ETH? Scan a code, it transfers to your wallet, it disappears from the wall, something else appears there and now you own it. Like that's freaking cool. Like that is gonna happen, you know?

• 1:25:05Ben Gilbert?

  Well, okay, thinking here about the future of mofi, Kevin, you're too much of a tinkerer to just let it be that the final form of mofi is like, I record an MP3 and then I toss it into some podcast players. So like, is there an on-chain version of content, media, something that could make sense for mofi?

• 1:25:27Speaker 02

  That's a good question. That's a very, very sharp and pointed, smart question that, of course, I think about that type of stuff. That's it. I don't think of it as much for mofi as I do for something like proof, where I think, what can we do that is unique? And, well, you just have to wait and see.

• 1:25:47Ben Gilbert?

  I can wait and see.

• 1:25:48Speaker 02

  I went and built, you know, Hodinkee for a few years. And Hodinkee was a kind of a proxy for what proof might eventually become. And like, you know, we did really in-depth editorial around mechanical timekeeping in watches. And that attracted millions of people per month, still does. I mean, there's 150 people that work at Hodinkee right now. It's a massive enterprise.

• 1:26:10Ben Gilbert?

  Hodinkee has this unbelievable characteristic. I think you guys do or did this best in the entire world of using content to enrich the value of purchasable goods. It is half a content business, half a commerce business, and they are so wonderfully intertwined. More people should take a look at that.

• 1:26:30Speaker 02

  Yeah, I mean, Hodinkee, they got that blend. And honestly, one of the things that we were really good at, Ben, the founder, and myself, when we sat down and we started planning out e-commerce, we wanted to make sure there was kind of a church and state line between editorial and e-commerce, because it's very important to be able to have independent, critical pieces written about watches that you may sell. And so we had to make sure and draw that line in the sand and say, and let the brands know that like, we can be critical about your watches still and talk about them. Like, if we don't like the way that something is manufactured, or you cut corners on some, one of your movements. And, I mean, it gets really geeky for people that aren't into the watch world.

• 1:27:10Speaker 02

  Think about like the mechanical insides of the watch and then think about the most hardcore vintage Porsche collector. They care about every little tiny detail inside of that machine. That is the engine inside of this watch. And so the geeks, and that's why partially why I'm attracted to it, like some of my favorite watches are not expensive showing off watches. They're watches that would never get any attention at a party in New York, but they're meaningful because of what's inside of them. You know, when you go and you pick up an Omega that has a 321 movement, that was the exact internal engine, the exact movement that was taken to the moon. Like that is awesome. And so like, that's the kind of geekiness that

• 1:27:55Speaker 02

  got me excited about watches. And that's what I want to bring to the NFT world. I want to talk and go deep with these artists and talk about what drives them and how they created some of the first, especially when we're on the programmability of the stuff. Like it's going to be really fascinating. Eventually, when I have Dimitri on that created one of the most popular projects out there called Ringers, I want to see code snippets of the Ringers project and put that into the article and show, I mean, that's the geeky level I want to get to. So that's where I'm hoping to take proof.

• 1:28:23David Rosenthal?

  And what's so cool, but well, I don't know if this is how you're thinking about things, but like with watches, it's like this little preview of what it could be. But the thing about watches is, you know, the super rare stuff, you know, it's hard to get, my dad's really into watches. Hi dad, if you're listening, but you can also kind of buy it anywhere, right? Like you don't have to buy it at Houdini. You're like, you can buy it at Houdini, you can buy it elsewhere. That may or may not be true, depending on where you go with proof. Like it's not like a retail environment.

• 1:28:51Speaker 02

  Right. Yeah. I mean, the thing is for us with proof, what I think about is, and this is what Houdini did as well. I don't think of these businesses being built in the next six months to a year. We need to spend the first three years gaining trust, right? Like that's the main thing is like in-depth editorial and content that is, is worth reading and a brand that you can trust to bring the best artists to you and explain why they're the best. And that means above and beyond me. I'm going to be looking to hire editorial folks that are both traditionally and classically trained art critics that are also embracing the NFT world and give us both perspectives, you know, like we need to know why something might be historically important when it comes to the new stuff that's being created on the NFT front. So it's going to be a fun little venture.

• 1:29:36Ben Gilbert?

  All right. Well, I've found a whole new thing that I'm imagining I'm gonna be very geeky about. So I'm excited to listen and tune in, Kevin.

• 1:29:44Speaker 02

  Awesome. Well, that's you're the first listener. Thank you so much.

• 1:29:47Ben Gilbert?

  Sweet.

• 1:29:48Speaker 02

  It hasn't been it's not out yet. So it might be by the time this podcast is out, but there's certainly be a way to

• 1:29:54David Rosenthal?

  Proofed out XYZ.

• 1:29:54Speaker 02

  Yeah, proofed out XYZ. There'll be a link up there to subscribe to the podcast, even if there isn't an episode out yet. There will be the historic ones that we've done so far. So that'll be the best way to join. And then of course, modern finance is for all things crypto. And that's where we go deep on all of the crypto stuff and, and that that's a whole nother can of worms. It's a lot of fun.

• 1:30:14Ben Gilbert?

  It's awesome.

• 1:30:15David Rosenthal?

  Probably our biggest segment of the acquired audience is entrepreneurs or aspiring entrepreneurs. Where can folks get in touch with you for that or?

• 1:30:23Speaker 02

  Yeah, it's kind of hard on the true side in that we typically, I would say 90% of our deals come from referrals from entrepreneurs that we've already backed. So we have a little over 300 entrepreneurs that are kind of referring in new companies to us. So we you kind of use that as a filter because if you just had an open submit form, you would just be overwhelmed and it'd be impossible to get through. So if you know a true company, that's the easiest way to get ahold of us. I would say outside of that, you know, my DMs are always open on Twitter. I try to go through them like once a week, but sometimes it gets a little crazy. For me specifically, I'm looking at all the new cryptocurrency blockchain related and NFT related deals. So if it's something outside of that realm, unless it's like health and

• 1:31:07Speaker 02

  fitness, which I also am very passionate about, or some consumer internet stuff as well, I'm probably not the right partner for you all to pitch. But yeah, that's those are probably the best ways, definitely through the network of founders who've backed.

• 1:31:20David Rosenthal?

  Love it. Okay. One last little tidbit before we go. He said Twitter. How'd you get on the?

• 1:31:26Ben Gilbert?

  Who to follow list?

• 1:31:27David Rosenthal?

  Suggested follow list. That happened at the bar in San Francisco?

• 1:31:30Speaker 02

  That happened at Ted. So at Ted in, we were down in Ted conference. This was when I was down in SoCal and it was me, Evan Williams and Chris Saka at a bar having some drinks. And this is when Twitter first started taking off. We were just talking to Ev. We're like, dude, this is crazy, man. There's like thousands of people signing up per day. Like it's nuts. You know, like at that point, I think it was like, you know, he's probably hitting 10,000 plus new users a day. It was like, it was clearly working, you know? And Sokka's like, hey, do you think you, you know, you think you could add Kevin and I to the suggested user list? And it, cause it was like, um, it was a manual list. And so it was one of those things where you, it was just hardcoded. It was no like algorithm like doing it.

• 1:32:11David Rosenthal?

  Yeah.

• 1:32:12Speaker 02

  And so Ev's like, he like, looks at us and he's like, all right. And so he pulls out his phone and he literally does it right there on his phone. And he's like, okay, done. And we're like, thanks dude. And like, I had turned on notifications for anytime someone follows me, because that's how small it was. And instantly my phone was like boom, boom, boom, boom, boom. I'm like, holy crap, dude. This is taken off. And I like went and turned off that, the notifications. And I was just like, getting so many followers. And then I was, it was just like, you know, it kept growing and growing and growing. And they kept that suggested users kind of the same for a very long time. And then I got this retweet from this woman. This was like a month or two later.

• 1:32:57Speaker 02

  And I like looked at the icons, like that girl's kind of cute. And I like click on her. And it was like a foodie, lives in San Francisco, into wine, into health and fitness.

• 1:33:06Ben Gilbert?

  No way.

• 1:33:07Speaker 02

  Working on her neuroscience PhD. And I was like, oh, who is this? And it was my, my now wife, Daria. And it was all because Ev added me to the suggested user list. And actually at my wedding, I told Ev that, like I especially called him out and said, thank you for, and Sokka for, for making that happen. Cause how, how I met, met my wife.

• 1:33:28David Rosenthal?

  I hope he did something like really nice. Can you get him like a Beeble or something? Or like a CryptoPunk?

• 1:33:33Speaker 02

  I'll have to see if he's into NFTs. I haven't asked him about that. I haven't seen him as much now that, that we've had COVID, but, uh, there should be a gift. I know I've sent him some nice bottles of wine in the past. So.

• 1:33:44Ben Gilbert?

  That is so cool.

• 1:33:46David Rosenthal?

  I feel like you gotta do more than wine.

• 1:33:47Speaker 02

  No, it's a good point. It's a good point.

• 1:33:49Ben Gilbert?

  You have like one of the best stories at a party behind the statement like, oh, my wife and I met online.

• 1:33:58Speaker 02

  Definitely. This was before I, you know, I'm kind of jealous, though, of these people that have it. It seems like it's easier these days. Like, I didn't have any of the swiping stuff that was like, you know, to date. Like, mine was all, back in my day, it was a 24 by 24 icon on Twitter that we used for dating.

• 1:34:14Ben Gilbert?

  You had to upvote your future wife.

• 1:34:15Speaker 02

  Yeah, exactly.

• 1:34:19David Rosenthal?

  Now the CryptoPunks make more sense.

• 1:34:21Speaker 02

  Yeah.

• 1:34:21Ben Gilbert?

  That's true.

• 1:34:22David Rosenthal?

  Love it.

• 1:34:23Ben Gilbert?

  All right, Kevin Rose, thank you so much.

• 1:34:25Speaker 02

  Thank you, guys. Thanks for having me. This has been a blast. It's always fun to walk through the history of all this stuff and talk about the future. So, so thank you.

• 1:34:34Ben Gilbert?

  All right.

• 1:34:35David Rosenthal?

  Likewise. All right, listeners. Now is a great time to talk about one of our favorite companies, Statsig.

• 1:34:43Ben Gilbert?

  Yes, there is a reason why the best product teams rely on Statsig, whether they are iterating on their core product features or shipping AI-powered experiences at scale.

• 1:34:53David Rosenthal?

  Yep. In the crazy speed of today's AI world, shipping fast is just table stakes now. It's basically trivial to build and deploy your app constantly. The real advantage is how quickly you learn what changes actually created value for customers, and how fast you can use that signal to guide what you ship next.

• 1:35:14Ben Gilbert?

  This is where Statsig comes in. It brings experimentation, feature flags, and product analytics into one unified system, so teams can ship safely, test rigorously, and directly link what they changed to how users actually behaved.

• 1:35:26David Rosenthal?

  So if you want to make learning your competitive advantage, whether you're building new AI experiences or just evolving your existing core product, go to statsig.com/acquired to get started.

• 1:35:37Ben Gilbert?

  Well, listeners, thank you for joining us on that journey. That was so awesome to get to do this with Kevin. As you could tell, so much of David and my, I don't know, adolescence, young adulthood, was involved in things that Kevin has built. So, super cool to get to do that with him.

• 1:35:52David Rosenthal?

  Super, super cool.

• 1:35:54Ben Gilbert?

  I have one special carve out for the end of this episode. It is a company that we at PSL Ventures just invested in. We led a $5 million round in a company called TrovaTrip out of, speaking of Portland, out of Portland. And I am so pumped about this company. And I just wanted to share a little bit because I think A, people should think about going on trips, but B, I think it's an incredibly cool company to work for. If anybody's thinking about their next thing, whether you're a software engineer or designer or marketer, whatever. So what TrovaTrip does is they enable creators to create custom trips to over 100 places around

• 1:36:33Ben Gilbert?

  the world and take eight to 16 people from their audience on a group trip together. So you're traveling with like-minded people to cool places with a person that you sort of identify with, be it a yoga instructor or your favorite disc golfer or someone else that you follow on Instagram or Tik Tok or anything like that. And it's just a really cool upending of the sort of group travel industry. And especially now when travel is actually starting to happen again. So it seems like it's just great timing and great team.

• 1:37:05David Rosenthal?

  Oh man, this is so cool. We totally need to get an acquired trip going. We go do all the, all the Silicon Valley hots. Well, now after this episode, we gotta go find that bar on, on to visit Arrow in San Francisco, where apparently everything went down in the web 2.0 days. But oh man, we can go to Stanford, we can go to the old pro in Palo Alto, go to Bucks in Woodside. Oh man.

• 1:37:29Ben Gilbert?

  Actually, David, you and I, we almost went to Bucks one time, right? We went to that

• 1:37:33David Rosenthal?

  We did, right? Didn't we?

• 1:37:33Ben Gilbert?

  Spot next door. No, we looked in, it was full and we ended up going to that other lunch place next door.

• 1:37:37David Rosenthal?

  To the like, the bakery.

• 1:37:39Ben Gilbert?

  Yeah.

• 1:37:39David Rosenthal?

  The Woodside Bakery, whatever it is. Yeah. Oh man, okay, we gotta do it. We gotta take you to Bucks.

• 1:37:43Ben Gilbert?

  Well, we gotta do it just so you and I can go to Bucks.

• 1:37:45David Rosenthal?

  Bucks is a crazy experience. This like diner in Woodside, which is right, right next to Palo Alto that has like all these crazy like airplanes on the ceilings and stuff and like all the old school, like the Don Valentine era venture guy, and even a little later too, like all the entrepreneurs and VCs would meet up there for breakfast.

• 1:38:04Ben Gilbert?

  It sounds like David's gonna be our tour guide. This is great.

• 1:38:06David Rosenthal?

  I am gonna love this.

• 1:38:10Ben Gilbert?

  Awesome. Well, listeners, if you are curious to learn more, it's trovatrip.com. Click the link in the show notes, or feel free to reach out to me in the Slack or at [email protected] if you're interested in the company in any way. Well, with that, join the Slack, acquired.fm/slash, become an LP. We just dropped probably our nerdiest LP episode ever, where we had Matt McBride on, who has worked in presidential administrations for hedge funds, advising on monetary policy, to basically walk us through like, the history of the Fed, and the Fed's role in our economy, and the difference between fiscal and monetary policy, and what the heck is quantitative easing. And for such a hot-button topic right

• 1:38:55Ben Gilbert?

  now, it was great to get like, an expert two-hour chunk of information on what are all these concepts, and how do they interrelate?

• 1:39:02David Rosenthal?

  Why does everybody like, try and interpret Jerome Powell's every last word? And why doesn't JP just say what he means? Like, there are reasons for this. Oh, it's so cool.

• 1:39:12Ben Gilbert?

  Glad it was.

• 1:39:13David Rosenthal?

  And also, check out Modern Finance. It's seriously really good. I've listened to almost every episode.

• 1:39:17Ben Gilbert?

  Yep.

• 1:39:17David Rosenthal?

  Like, we talked about the Beeple episode is so great. We'll link to that in the show notes. Man, what a cool dude. And not what you would like, just think on the surface. Like, you gotta listen to it. Like, he's awesome.

• 1:39:29Ben Gilbert?

  Careful, you'll become an NFT believer after you do.

• 1:39:34David Rosenthal?

  Which is a good thing.

• 1:39:35Ben Gilbert?

  All right, listeners, we will see you next time.

• 1:39:37David Rosenthal?

  We'll see you next time.