ACQ Sessions: Jason Calacanis

We kick off ACQ Sessions with the-behind-the-scenes story of All-in, from the world’s greatest moderator himself Jason Calacanis. ACQ Sessions is our new, occasional “MTV Unplugged” version of Acquired: a great IRL guest, a bottle (or two) of wine, and no script. We talk about everything you’d imagine we would over wine with JCal — All-In, bestie relationships, money & politics in Silicon Valley, who his influences and mentors have been (one surprise — the great Fred Wilson of USV!), what motivates him to keep grinding and why, at age 50+ when he could easily be winding down he’s instead speeding up into the most productive phase of his entire career. Pour a beverage yourself, pull up a comfy seat and join us! *More Acquired:* - Get email updates https://www.acquired.fm/email and vote on future episodes! - Join the Slack http://acquired.fm/slack - Check out the latest swag in the ACQ Merch Store https://www.acquired.fm/store! _Note: 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.

• 0:08David Rosenthal?

  It was a magazine.

• 0:10Speaker 01

  Magazine, yeah. That's how it started, yeah. Magazines was like the original platform for... Wait, have we started?

• 0:16Ben Gilbert?

  Silicon Alley.

• 0:17Speaker 01

  I guess we've started.

• 0:17David Rosenthal?

  This is the trick. We've just been recording the whole time.

• 0:20Ben Gilbert?

  Yeah.

• 0:21David Rosenthal?

  Welcome to Acquired Sessions.

• 0:22Ben Gilbert?

  All that stuff that you said beforehand, that was really juicy, I don't think we should put that in.

• 0:26Speaker 01

  No, definitely not. Definitely not. We don't want to tell people where the bodies are buried. Well, cheers, boys. Here we go. Is this the first one?

• 0:33David Rosenthal?

  This is the first in real life. What, I think this is our ninth, 10th together, something like that?

• 0:39Speaker 01

  A lot between the two pods, yeah, for sure. Great to know you, boys.

• 0:42Ben Gilbert?

  So this is the first Acquired Sessions.

• 0:44Speaker 01

  Acquired Sessions. I feel like I should get out a guitar here and just play some Dylan.

• 0:49Ben Gilbert?

  This is your baby. What is Acquired Sessions?

• 0:52David Rosenthal?

  Acquired Sessions is, normally on the show, we are like so scripted.

• 0:56Speaker 01

  Yeah, you are.

• 0:57David Rosenthal?

  And we have a great time. We do four hour episodes. It's awesome. But really, for folks like you, who we know really well, what happens if we throw out the script?

• 1:07Speaker 01

  And just chop it up?

• 1:07David Rosenthal?

  And we just chop it up.

• 1:08Ben Gilbert?

  David Rosenthal unplugged.

• 1:10Speaker 01

  Wow, I love it. This is the literally MTV Unplugged.

• 1:13David Rosenthal?

  Literally.

• 1:14Ben Gilbert?

  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.

• 1:33David 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.

• 1:54Ben 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.

• 2:16David 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.

• 2:34Ben 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.

• 3:02David Rosenthal?

  So in the juicy stuff earlier, you mentioned Mahalo.

• 3:05Speaker 01

  Yeah.

• 3:05David Rosenthal?

  I don't know. Is that why you started?

• 3:07Ben Gilbert?

  Can we just keep referring to the juicy stuff?

• 3:09David Rosenthal?

  Yeah.

• 3:13David Rosenthal?

  Is Mahalo why you started, you went from print to print to?

• 3:17Speaker 01

  Well, in the 90s, you know, I grew up in Brooklyn. My dad had his bar seized by the feds because he didn't pay his taxes during the 1987 crash. He became like, he got behind and the fed showed up one day and this was the maybe six weeks before I was set to go to college. And he said, Hey, son, I can't help you with college. Good luck. And I might be going to jail, so take care of your mom. So he was like really behind on his taxes and you know, state liquor authority, they kind of take it serious. So feds come, shotguns, the whole thing. They seize the place, they seize everything in it. And I

• 4:00Speaker 01

  was like, well, I guess I'm going to school at night and I'm going to work during the day. And I worked fixing laser printers and that was like a really good racket. The HP had just come out and.

• 4:12David Rosenthal?

  Were you set to go to college somewhere else?

• 4:14Speaker 01

  Well, that's another story, but I was set to go to Brooklyn College. I got into that. I had also taken the police exam to be a police officer. So my brother went into the force. And then I said, you know what? I'm gonna see if I can go to college and make that work. So I'm gonna go to Brooklyn College. So I decided to work during the day and then I went to school four nights a week, six to nine PM. Carried full credits, 16 credits a semester. And I would work fixing laser printers all day. I was a bad student. I was always that student who underperformed. I didn't find great meaning in academics, but I had a computer when I was in high school and I was more interested in playing with my 300 broad modem, which then became a 1200 broad modem in my PC junior. So

• 4:55Speaker 01

  it kinda, you know, like many people of that era, we were sort of set on a path because we were the first generation to have a computer at home. I actually had an Atari 2600 and it could play Tank, was the game that came with it, and Pong. And so my dad bought this for us when I was six or seven years old, 1976, 1977. And he had one of the first Pongs in Brooklyn in his bar.

• 5:14David Rosenthal?

  Oh, he must have cleaned up on that.

• 5:17Speaker 01

  Oh, my God, it was crazy. And so we, I just got exposure to video games and computers and I was like, wow, this is incredible. Like, computers are gonna change everything. And then I happened to hack some software. We used to I ran a lot of scams, but

• 5:32David Rosenthal?

  You told us about the VHS.

• 5:34Speaker 01

  So VHS, Jason's Hot Tapes was technically my first business, but there was a side job I had, which was cracking software. So we were we would make copies of like Chessmaster and stuff like that and then sell them for 10 bucks. And then we started like hacking and doing what was called phone freakings.

• 5:48Ben Gilbert?

  When you were doing this stuff, like, you'd be reasonably technical to do it. Not like the, you know, not like Wozniak technical, but like

• 5:56Speaker 01

  We soldered chips sometimes. We changed, you know, we put, to put memory in at that time, you had to like take the memory chips and put them in and then bend them over and stick them in.

• 6:06Ben Gilbert?

  Did you ever think about, like, did you consciously ever make a fork? Where you were like, not tech media, and of course, media about tech, but you're like, I'm not gonna be the guy doing the boards. I'm gonna be the guy writing about the people doing the boards.

• 6:19Speaker 01

  It's a very good question. I used to go to Bleecker Street and I used to hang out in the West Village or the East Village. It was like the cool places to hang out. And like a thing to do would be to go to Tower Records and look at the zine section. So there was a concept of a zine, which was short for magazine. But a zine was something you wrote with your friends. You printed it yourself at a photocopy store.

• 6:43Ben Gilbert?

  It's like blogs before blogs.

• 6:44Speaker 01

  Blogs before blogs. And I created a zine. I was like, I'm going to be a magazine publisher. So the first one I did was Cyber Surfer, which was about dial-up magazine, dial-up services and CD-ROMs. And I did it with my friend Brian Alvey, whom you might have heard of in my career. We went to high school together.

• 7:00David Rosenthal?

  Weblogs?

• 7:01Speaker 01

  We did weblogs together. Yeah, so, but in the early 90s, I did.

• 7:04Ben Gilbert?

  Which is Engadget, Twad.

• 7:06Speaker 01

  All of that stuff, yeah.

• 7:07Ben Gilbert?

  Everything you sold AOL.

• 7:08Speaker 01

  Thing I sold AOL. But anyway, before that, I did this mag, I did that magazine. And then I had met Fred, I met Jerry Colonna at Internet World, the first one. And he, there was a booth.

• 7:19Ben Gilbert?

  That's right, when Jerry was a VC, before he was like the whisperer of startups.

• 7:24Speaker 01

  He was consulting for Lycos and I think CMG. And so there was a Lycos booth. And I had met this young lady at it and we hit it off and we're talking. And then she introduced me to Jerry Colonna. And then I met Jerry Colonna in an office no bigger than this room in Union Square. And he said, listen, I'm leaving Lycos, but I'm going to start this Hackney Ventures with my friend Fred. I want you to come read business plans for us. And so I met Fred Wilson and I would go up to them and they were doing, JP Morgan was going to back them for their venture firms. This was 1994, 95.

• 7:51David Rosenthal?

  This became Flatiron.

• 7:52Speaker 01

  It became Flatiron.

• 7:53Ben Gilbert?

  JP Morgan was the first big anchor of Flatiron.

• 7:55Speaker 01

  They were half of it and Masayoshi Son, SoftBank was the other half.

• 7:58Ben Gilbert?

  No way!

• 7:59David Rosenthal?

  So they wanted you to come like be a VC associate.

• 8:01Speaker 01

  Not a VC, just to read business plans. So the deal was they would take me for sushi and pay me a thousand bucks.

• 8:07Ben Gilbert?

  Wait, what do VC associates do besides just read business plans?

• 8:09Speaker 01

  Exactly. Well, anyway, it was a thing. And so I had the magazine store at Silicon Eye Reporter and they were paying me. And so I read about this. Beverly Hills Internet Company, which got rebranded as GeoCities. And I wrote a little coverage of it and I said, you should invest. I'm 24 years old. I don't even know what VC is.

• 8:26David Rosenthal?

  That's where Flatiron made all their money.

• 8:28Speaker 01

  Yeah, they were going to invest anyway. The Flatiron became USV, right? Yeah, Flatiron went with Jerry Colonna then when Jerry decided he wanted to move to Colorado and just chill. He had made enough money, I think. Coach founders. Coach founders, I think. And yeah, maybe he had like, I think he's been pretty public about it. Like, I don't want to say a nervous breakdown, but a kind of like, maybe a fork in the road? Like, making a decision about what you want in your life kind of situation.

• 8:51David Rosenthal?

  You know that great book about it.

• 8:52Speaker 01

  Yeah, yeah, yeah. And so Jerry was a good mentor, but Fred actually became ultimately my deep mentor at that time. And Fred said to me, listen, you're doing Silicon Valley Reporter, you're writing about us, and the companies we're investing in, and you're doing stuff, which would you rather do? And I was like, I think I'll do the magazine.

• 9:11David Rosenthal?

  This was before now, it's like.

• 9:13Speaker 01

  And now it's like, I do both. Why choose?

• 9:15David Rosenthal?

  But just to back up to GeoCities, that sold to Yahoo for like three.

• 9:18Speaker 01

  Five billion.

• 9:19David Rosenthal?

  And.

• 9:19Speaker 01

  I think four or five.

• 9:20David Rosenthal?

  Flatiron was the main investor.

• 9:21Speaker 01

  Yeah, Flatiron maybe owned five or 10% of it at the time. It was like a huge win for them. I mean, Fred was on fire for New York VC and Jerry, they did pretty well.

• 9:28David Rosenthal?

  How did that happen, right? Like, I mean Silicon Valley was here, but they were in New York. Like, what was going on?

• 9:33Speaker 01

  Yeah, we just, there was a lot of good companies brewing in New York. And my concept with Silicon Valley Reporter was, well, they have red herring. Outside in the Bay, but I own New York and I had Silicon Valley Reporter. And then I started one called Digital Coast Reporter in LA. So I had two magazines, two conferences, two email newsletters. I was kind of king of New York, right? I grew that business to $10 million in revenue off my credit cards. And had 75 to 100 people working for me when I was 27 years old. And I didn't know anything about how to run a magazine, how to run ad sales. I taught myself everything.

• 10:06David Rosenthal?

  What did your family think of this? Like?

• 10:08Speaker 01

  It was pretty heady stuff because I wound up being on the cover of the New York Times, on Charlie Rose, and they wrote a feature story about me for 8,000 words in The New Yorker. So anyway, it's a really cool time in New York because at that time, you were either in media or finance or art, publishing. It was like a finite set and I was in publishing, but I was also in this new thing, technology. And so everybody wanted in on that. It would be like, the equivalent of crypto is today, like at its peak where like, and you were. The equivalent of like Satoshi or something like it was crazy to be

• 10:40Ben Gilbert?

  Yeah.

• 10:41Speaker 01

  The New York internet guy.

• 10:43Ben Gilbert?

  Can I? So we talked about a lot of this when we did our like big Jason Cali- Empire of Jason Calacanis episode with you. So I want to like put this on pause.

• 10:52Speaker 01

  Yeah, sure.

• 10:52Ben Gilbert?

  People can go listen to that. You should. It's great. We get like the detailed story of like Weblogs Inc. And all that great stuff. And you mentioned, I want to like, take us from you're only as good as the, you know, your greatest, your newest thing.

• 11:05Speaker 01

  Sure.

• 11:06Ben Gilbert?

  Because the last time we talked to you, you were just starting All In.

• 11:09Speaker 01

  It's hilarious.

• 11:10Ben Gilbert?

  And like, can we talk podcasting?

• 11:11Speaker 01

  Of course. I love it. Podcasting is like, I think perhaps my greatest medium.

• 11:16Ben Gilbert?

  What happened with All In? How did? I mean, it's weird. Has it surpassed your wildest expectations?

• 11:25Speaker 01

  Um, I thought it would be something Chamath and I would do 10 times.

• 11:29Ben Gilbert?

  Yeah.

• 11:29Speaker 01

  So the, the origin story is pretty simple. Chamath, I knew because he was running ICQ.

• 11:37Ben Gilbert?

  Chamath was running ICQ?

• 11:39Speaker 01

  At AOL. And I had sold my company AOL and like the revolving door of AOL. It was like Ted Leonsis had this March to a Billion. My Greek brother, a mentor, had this like March to a mil- a billion offsite. And so I went to this and I had just sold Weblogs Inc.

• 11:56Ben Gilbert?

  Like a million AOL users?

• 11:57Speaker 01

  Hot shit.

• 11:58Ben Gilbert?

  That's the, the

• 11:59Speaker 01

  That was the idea with that. Well, with Weblogs Inc. And with AOL and other assets they wanted to buy, they were going to March to a billion users.

• 12:07Ben Gilbert?

  Yeah.

• 12:07Speaker 01

  It was like this crazy rallying cry. And we had these t-shirts, March to a Billion. So I go to that and I teach Chamath and I was like, hey, and he's like, hey. And we introduced each other and we had known of each other. And I said, what are you doing here? He's like, I'm running ICQ into the ground, you know, I'm just writing it down every month that loses a million members. It's hilarious. And he's like, yeah, but I'm leaving. I'm going to go. I'm gonna go to the west coast, I'm gonna go work at this VC or whatever. So, all right, nice seeing you. And so then when he was there, I was in LA. What VC did he go work? Cause he was at Facebook.

• 12:35David Rosenthal?

  Mayfield.

• 12:35Speaker 01

  Mayfield for a year. And then Sean Parker introduced him to

• 12:41Speaker 01

  Zuck. And Zuck needed, you know, like a Chamath. He needed like somebody who would just Chamath built the growth. He built the growth team. And he was like, I don't, there is no equivalent of growth. That was, the idea of growth hacking didn't exist as a term until Chamath did what he did. He said, just find me the smartest people. I'm hiring based on IQ. And I'm hiring based on desire to make a lot of money and be a beast. And he just went, he went into beast mode. Cause you know, he too was very hungry.

• 13:10David Rosenthal?

  You guys must have been like brothers from another mother.

• 13:12Speaker 01

  Yeah, for sure, for sure. We're, we're definitely, you know, both outsiders in Silicon Valley. And, um, you know, I had Chamath come on the pod. This is being startups, that is.

• 13:22David Rosenthal?

  We listened to it. It was, it's fun to go back to that moment.

• 13:25Speaker 01

  The first one. And you can see how he's not, you know, polished. He's not Chamath, you know, as Greg Arias or whatever. He's a little more reserved.

• 13:33David Rosenthal?

  He doesn't have the Loro on.

• 13:34Speaker 01

  No Loro Pian. He was. Was he in great shape or? No, not what I'm too sure. He was like, he was like a dork, you know, like he, but he was.

• 13:42David Rosenthal?

  This is Bezos pre.

• 13:43Speaker 01

  No, yeah, it was like Bezos pre, yeah, whatever. You know, he, he always was a poker player. He was playing Atlantic City. So he was, you know, like myself, an outsider who wanted to take risk and wanted to win. And, um, you know, confident, you know, even maybe more confident than both of us should be, but, um, and so I kind of introduced Chamath to the world by convincing him to come on the pod, which he was like reluctant to do when he was at Facebook, but he did it after Facebook. So I kept asking him to come. He finally was in LA. He came on the pod. And then people, I was like, he's really good on stage. Like he's, he's funny, whatever. And so. Which at this point you had an eye for.

• 14:22Speaker 01

  Sure, of course. I mean, one of the things when I was a podcaster in those early days, you know, I'm talking about 12 years ago, whatever, is, you know, I introduced a lot of people to the world.

• 14:29Speaker 01

  I think like 14, right? 14, yeah. I introduced people to the world. Yeah. Uh, yeah, it was like 2008, I guess, whatever. So I introduced a lot of people who were in tech to the, you know, and it was only a couple thousand people.

• 14:40David Rosenthal?

  And then as now too, like. You could be a great founder, you could be a great, you know, person in tech, but like, that doesn't automatically make you a compelling podcast.

• 14:49Speaker 01

  As we know. No, of course not. No, I mean, there, I have my own theories about what makes for a great guest. We'll put that on the side for now. But anyway, we started a friendship, we started playing cards together. We start hanging out, you know, trading notes kind of thing. And he's gonna start his venture firm. I'm a scout at Sequoia, all that stuff. We start playing and trading notes. And we just become great friends. But then he was coming out of CNBC one day and he's like, oh, my God, you know, just like, we have such a good rapport when you interview me. Because he had done a bunch of interviews with me on stage and stuff like that on my events. He's like, I want to do a podcast with you. I was like, yeah, you can come on this week and start up anytime. It's twice a week now.

• 15:24Ben Gilbert?

  And Which it's now five times a week.

• 15:26Speaker 01

  Six, six.

• 15:27David Rosenthal?

  Sunday. Plus I'll see.

• 15:28Speaker 01

  I'm gonna go, I may go back down to five next year. It's a little much right now.

• 15:31David Rosenthal?

  Yeah, dude, you, I mean, we'll come back to this, but you're killing yourself right now and you're on act three.

• 15:36Speaker 01

  Yeah. I have more energy now than, I may, I may have, I just this like, coming out of the pandemic, might have as much energy as I did when I was in my twenties. But for different reasons, different type of energy. Anyway, Chamath calls me, you know, coming out of the studio, I don't know if he was in New York or he was in the one market, one in San Francisco here. But he said, I want to do this part with you. I said, okay. And he said, I want to do a new pod with you. Just me and you, we talk. I was like, sure. He's like, what should we call it? We're texting microphone. I was like, we should call it all in.

• 16:07Ben Gilbert?

  And this is 2020?

• 16:08Speaker 01

  Yeah. It's like two years ago, whatever. And I said, yeah, we should call it all in. Like, we should come with a poker name. He's like, yeah, great. Like, a raise or something like all in.

• 16:15Ben Gilbert?

  Because you had, you'd been referring to this poker game on air on

• 16:18Speaker 01

  Yeah, I would talk about it once in a while, the poker game that doesn't exist. And Sky Dayton and I had a poker game with Brooke Hammerling, the famous PR person, at the Code Conference, which was the All Things D conference before that for 20 years. Then Chamath had had a poker game, Sacks, I had hosted it floating and putting all that together. Yeah, I'd refer to it many times on the pod, but tried to, you know, keep it from becoming public. But it was me, Bill Gurley, it's all public now.

• 16:44Ben Gilbert?

  Mark Pincus, right?

• 16:45Speaker 01

  Or maybe Pincus used to come to the Code one.

• 16:48Ben Gilbert?

  Yeah.

• 16:48Speaker 01

  Um, there's another funny story. And lots of funny stories in my life. But anyway, so then the pandemic happens and we're like, well,

• 16:58David Rosenthal?

  We're letting you go and just dropping these little breadcrumbs.

• 17:00Ben Gilbert?

  We gotta pick them up on the

• 17:01David Rosenthal?

  Yeah, we gotta pick these up.

• 17:03Speaker 01

  Anyway, at some point, I'll write a biography. Anyway, nine years, third book. Anyway, the

• 17:11Speaker 01

  Then we were, the pandemic starts to happen, like, well, Sacks has some ideas about masks, and then Friedberg.

• 17:18David Rosenthal?

  Sacks and Friedberg weren't, there was no besties originally, right?

• 17:22Speaker 01

  No, no. And I mean, in truth, like, Friedberg and I weren't besties before All In. I mean, we knew each other, we were friends, but not besties. I was besties with Sacks and Chamath, and now Friedberg is a bestie. And, but he played in the game, obviously, and we had just started to have a developer friendship. But anyway, that foursome kind of clicked, right? Pretty quickly. And I think, you know, I was a really good interviewer. I'd studied interviewer techniques and really, you know, after doing whatever, I'd done at least a thousand episodes of Twist at that point. And I had had Sacks on many times and Chamath. So I was very comfortable with them. And at the poker game, we break chops and I make jokes. And Chamath's a great host and just very comfortable with each other.

• 18:07Speaker 01

  And Friedberg kind of joined that group and it clicked. And I think during the pande, and I thought maybe this last 10, 20 episodes, but during the pandemic, I think people wanted information. And I realized like, oh.

• 18:22Ben Gilbert?

  In perspective, I mean, I think that's a thing. I'll, I'll tell you, I never expected to be listening to David Sacks talk, coming from where he comes from politically and where I come from politically and going, hmm, that is a good point. And that perspective is like so helpful in our polarized world today.

• 18:41Speaker 01

  Yeah. It's very unique. And, you know, around the poker table, we all listen to each other and we're friends, but the world does not want us to be friends in some ways. The world wants us to be enemies and I kind of think about it like, you know, best of enemies kind of situation. Like, we debate specific things like Gore Vidal and.

• 19:01Speaker 01

  Who is this adversary? Anyway, it's a great documentary about Gore Vidal and

• 19:06David Rosenthal?

  Who's Gore?

• 19:06Speaker 01

  William F. Buckley. They're just two public intellectuals. One was on the left, one was on the right. And there's this documentary, Best of Enemies, in the 60s. They started debating like different political conventions and it was like the most compelling thing on TV.

• 19:19David Rosenthal?

  But they were like friends.

• 19:21Speaker 01

  Best of Enemies. They weren't besties like Saxon and I are, but you know Gore Vidal was just, he was gay.

• 19:29Speaker 01

  Kind of closeted or quietly gay and on the left and Buckley was like a serious conservative and they went to blows sometimes on the show like at one point Buckley, I think he called him like a sissy or something like really like derogatory as a gay man and the world didn't understand he was exactly gay. It was like sort of time period in the 60s where like maybe some adults understood like, yeah, that's a gay man, but we don't say that's a gay man.

• 19:55David Rosenthal?

  Ben yesterday, we were driving the Castro's right nearby and we saw a naked guy in the Castro and I was like, oh, naked guy in the Castro. Ben was like, what is going on? Like dude, you gotta understand in the Castro.

• 20:04Ben Gilbert?

  Like huge jacked dude walking around and and super sunny. So he's like just all like slicked down.

• 20:11Speaker 01

  But did he have his shoes on? Was he wearing combat boots? They usually wear boots.

• 20:15David Rosenthal?

  Yeah.

• 20:15Speaker 01

  And then they usually carry a sarong. There was a big debate when I first moved up here because there was a number of folks who used to like to get a Starbucks and they had to like negotiate. And they were like, how about a sarong in Starbucks? Cause you're gonna sit.

• 20:28David Rosenthal?

  Right, right.

• 20:29Speaker 01

  Bare ass.

• 20:29David Rosenthal?

  And for for context, for you know, I've explained this to Ben, but like this is a thing in the Castro in San Francisco. It's a cult. It's like a now it's like you see it and it's like, ah, this is like a relic of the 60s, 70s.

• 20:41Ben Gilbert?

  It actually was pretty awesome because David, we're like driving up and David goes, oh, a naked guy. It was the most like warm, hearty.

• 20:47Speaker 01

  Yeah, I had to, um, yeah, adjust as well as a New Yorker because as a New Yorker, if somebody's naked, that's a sign that if there's about to be some crazy person in a fight and police and chaos. And here it means like high fives and write ons. But you know, growing up in New York, like if somebody takes their clothes off on a public transportation or in a cafe, like people are getting a baseball bat and calling the police and like this shit's about to go down.

• 21:14David Rosenthal?

  Oh my gosh.

• 21:15Speaker 01

  You know, and then here it's like, you know, high five and live your life. That's one of the things I love about San Francisco. But anyway, the pod's gotten very big.

• 21:21Ben Gilbert?

  So you get the gang together and like, why do you think it works?

• 21:25Speaker 01

  Like, is it, it's like the number one ish? Well, in our business it's number one, of course, but it's number, it was number 28 last week.

• 21:34Ben Gilbert?

  Like in the world.

• 21:36David Rosenthal?

  You guys have transcended. Like this is more than just.

• 21:38Speaker 01

  Tech anymore. It has nothing to do with finance or tech anymore.

• 21:40Ben Gilbert?

  I think it works.

• 21:41Speaker 01

  Tipped over into colleges. I was at, I was, you know, skiing in Tahoe and I, you know, I was with my kids and it's hard to get a table type situation. I was like, hey, I hate to be a pest, but I see you're wrapping up and no pressure, but are you going to be leaving soon? Cause I'd love to camp out here and get your table.

• 21:58Ben Gilbert?

  And they're like, stop busting my balls, Jason.

• 21:59Speaker 01

  Looked at me and she goes, J Cal? And I was like, have we met? And she's like, no, I listen to your pod twice a week. I'm like, it's only on once. She's like, I listened to it twice. And I was like, oh my God, that's so nice. She's like, I was like, are you in the industry? She's like, I'm a dentist.

• 22:12Ben Gilbert?

  Wow.

• 22:13Speaker 01

  Reno. And I'm like, you're a dentist in Reno's. Can I ask how you found out about? She's like, I don't know. Like.

• 22:18Ben Gilbert?

  She's like, I deeply care about San Francisco politics.

• 22:20Speaker 01

  No, somehow she had found it. And this is, you know, during the pandemic situation. Then that's when I realized it had crossed over.

• 22:25David Rosenthal?

  Was there a moment for you, either you four or you where you were like, whoa, this is?

• 22:32Speaker 01

  You know, I've been, um, micro famous, you know, micro celebrity multiple times in my career.

• 22:38David Rosenthal?

  But this is different.

• 22:40Speaker 01

  Yeah, not for me, you know, and I got a lot of famous friends. Uh, you know, I, I'm used to getting recognized. I'm used to people taking pictures. What I'll say is like, where it used to be, you know, if I go to Austin or New York, people would say, I would have three people stop me on the street a day if I was walking around in New York. Now it's 20, you know, or 10 and they want to take a selfie and it's, you know, it's just, you know how podcasting is, you guys get recognized and it creates a level of intimacy with people.

• 23:09Ben Gilbert?

  For sure.

• 23:09Speaker 01

  If they're in the habit.

• 23:11Ben Gilbert?

  Yes.

• 23:11Speaker 01

  Because you're hearing people every week and then people become characters. And I tried to make everybody, I was, you know, in, in.

• 23:18Ben Gilbert?

  Be people on the show or?

• 23:20Speaker 01

  In all honesty, I did craft with All In, I was very premeditated in creating some character. I've never really talked about this.

• 23:27Ben Gilbert?

  Yeah, yeah, yeah, this is.

• 23:28Speaker 01

  But I crafted some character kind of arcs. I, the fights are all real, trust me, there's nothing scripted about that. But I did say like, I think I can as the point guard here, kind of shape the conversation. And I literally created the character of the Sultan of Science.

• 23:47Ben Gilbert?

  Right, that's what I was gonna say.

• 23:48Speaker 01

  And, you know, Freeberg didn't even have a Twitter handle. Zero followers.

• 23:52Ben Gilbert?

  There's even a character of J Cal on All In, like there's.

• 23:55Speaker 01

  J Cal, the world's greatest moderator, sure, yeah.

• 23:58Ben Gilbert?

  I think more like J Cal, the guy who lets himself be the punching bag because it plays for the show.

• 24:03Speaker 01

  A little bit. Uh, I would rather not, if I'm being honest, I'd rather not be the punching bag. Like, they're like, you're the poorest guy on the show. I'm like, do we need to point that out so often, guys?

• 24:12Ben Gilbert?

  You're like, not by, not by much.

• 24:14Speaker 01

  Like, I, I'm feeling really good about myself. You don't have to point out that you all have more money than me and you, two of you have planes and I don't. And it's, it's okay with me, I, I could have a plane, I guess, I could get one, but.

• 24:26Ben Gilbert?

  You care about the environment.

• 24:28Speaker 01

  Well, no, it's also like, I don't want to waste a ton of money and, you know, whatever reason.

• 24:33Ben Gilbert?

  But you do, you do let yourself play that role of like, like you have been enormously successful and you sort of let the role of J Cal on the show be like, that guy who one day wants to be like us, maybe he'll, maybe he'll make it.

• 24:46Speaker 01

  I actually never wanted to play that, actually. No, that was not, that was just the boys breaking my chops, maybe. So maybe it's a little bit of like them wanting to, uh, you know, maybe, uh, take the piss out of me a little bit, which is fine, because, you know, I give it as good as I can get it. But I think that's probably for them, and you can ask them when they're on the pod. I think for them, that's kind of the diss, that's the one they can easily go to. It is, I'm the poorest guy on the show, but like. I've done OK.

• 25:15David Rosenthal?

  What I, maybe let's flip it like for them before All In, I mean, maybe Tomoth had a little bit of a public

• 25:21Speaker 01

  No, they were not famous.

• 25:21David Rosenthal?

  No, right.

• 25:22Speaker 01

  They had no go to market. They're all, this is a new thing for each of them to hit this level of notoriety. It's not for me.

• 25:28David Rosenthal?

  What do you think for, I mean, we should ask them this, but like if you were to speculate, caveat that it's speculation, what do you think for them All In has like done like?

• 25:40Speaker 01

  Well, I mean, for Friedberg, nobody knew who he was, except if you worked at Google or you were in VC. Like he's very connected in those circles. What's that? Or Monsanto. Or Monsanto, like he's very connected in those circles, but he was kind of under the radar guy. I think really by design, he didn't have any desire to. So I think it's probably the biggest adjustment for him. The, the increase in profile has certainly been the highest for him and he's loved. There was a moment when I like jokingly said to people during the Q and A session at All In Summit, you know, just say who your favorite bestie is and then direct question. And it was like five in a row Sultan of Science. And it was like, oh my God, what have I done? Now I've created this monster, you know, and he at the time like would barely show up for like, you know, he would show up for two out of three episodes. He'd be busy.

• 26:25Speaker 01

  It wasn't a priority for him. Right. So I'd be like, all right, I'll put Brad Kersner in. If you can't make it, I'll try to get Bill Gurley to show up or whoever, Draymond to fill in for him. You know, and it was always like, I wonder if Friedberg will show up, but he's actually really committed to the show now. For Sacks, he was high profile, but nobody really knew him as a Republican. So he kind of uncloaked as a Republican on the show.

• 26:44David Rosenthal?

  Well, I feel like he was also like, he was almost even more so than any, you know, well, not you, but he was high profile if you knew about the PayPal mafia. But he was like the least kind of public of the PayPal mafia.

• 26:58Speaker 01

  Of the PayPal mafia, you would say Elon, Reid Hoffman, Peter Thiel.

• 27:04Speaker 01

  Max Levchin, Jeremy Sopelman, Chad Hurley, Ruloff.

• 27:10Ben Gilbert?

  Yeah.

• 27:11Speaker 01

  And I guess Sax would be somewhere in that strata of like being known.

• 27:14Ben Gilbert?

  But I feel like.

• 27:15Speaker 01

  Being known.

• 27:15Ben Gilbert?

  Being known, yeah.

• 27:16Speaker 01

  Being known, but yeah, you know, and I, I think part of the reason this works is Sax, I think Sax has probably taken the brunt of the head of the pod.

• 27:23Ben Gilbert?

  Yeah.

• 27:23Speaker 01

  Because he is so passionate about, you know, a lot of topics that maybe are unpopular in the tech circles. So I do think like it's cost them deal flow on the margins, probably. I think there's probably.

• 27:36Ben Gilbert?

  I don't really margin.

• 27:38Speaker 01

  I wonder.

• 27:39Ben Gilbert?

  On balance.

• 27:40Speaker 01

  He said that jokingly on the show. I don't know. I'm just thinking like, maybe there's somebody.

• 27:43Ben Gilbert?

  Craft has ascended because he's done all in.

• 27:46Speaker 01

  I guess, yeah, sure. I'm trying to think if like would, is there a founder, I wonder, I don't know this, but is there a founder who's a young founder who would say, I would never take money from Peter Thiel's venture firm. Cause I'm so liberal.

• 27:59Ben Gilbert?

  For sure there are. And those people feel that way about craft now, but for every one of those, there's 10 more.

• 28:05Speaker 01

  I kind of agree with you. Yeah, I would agree with that. So anyway, I do think like he's joked that it's cost him deal flow. I don't know if it has. Um, I think truly the benefits.

• 28:12David Rosenthal?

  The pod too, I think for people, for people in America and people in tech has moved, I think a lot of people towards the center.

• 28:21Speaker 01

  I think a lot of people were moving towards the center and we codified it for people. We maybe made it okay to admit you're a moderate.

• 28:27Ben Gilbert?

  Yeah.

• 28:28Speaker 01

  You know, I, I, I've been telling folks from the beginning, I'm an independent and a moderate. I voted probably Democratic three out of five times, four out of five times. But mostly that's a function of the fact that I've lived only in New York and California in my life, where you don't really get many Republicans or moderates, but I voted for Bloomberg, Giuliani, when Korea was crazy and Pataki, who are all Republicans.

• 28:52David Rosenthal?

  Were you here during the Schwarzenegger or were you still in New York?

• 28:55Speaker 01

  I wasn't, but I would have voted for him. Um, I, I like competent people and I supported Bloomberg for president, which got me a lot of flack.

• 29:03Ben Gilbert?

  Really?

• 29:04Speaker 01

  I don't understand why. People were very upset that I was for him instead of whoever.

• 29:09David Rosenthal?

  I think you guys talked about this on the pod that like, oh, what was the two by two quadrant of like, whatever it was, we all think we are here in Silicon Valley, which is like social, liberal, fiscal conservative. Yeah. We were like, everybody should be that, but we're the smallest of the four groups.

• 29:25Speaker 01

  Yes, it is a small group. I, I, um. I think I believe in competence and staying out of people's lives. So I, you know, it's very hard to know because and then even David, I mean, this is, I think, when David and I fight on the pod, which some people love, and I think some people probably turn the pod off when that happens and they don't like it. And certainly, I, the MAGA group is, has no love lost for J. Gal, I can tell you that. Like, my replies have been really crazy. I would get like brigaded the last couple of weeks. Nuts. It's funny, but it's also like, on the margins, like, they can get a little scary, like, they'll dox me sometimes, and I, you know, that's not fun. A handful of times it's happened. But, you know, I had

• 30:06Speaker 01

  to tell David, like, David, I am not like, I don't actually listen to MSNBC and Rachel Maddow to get my information. And by the way, you're pro-choice, pro-gay marriage, anti-war.

• 30:22David Rosenthal?

  Yeah, he's the Dove.

• 30:24Speaker 01

  And I, I was like, well, okay, if you, if we want to play this game, I'm gonna go, it's W. David the Dove. And now you're making me into Jason the Hawk? Like, what are we talking about here? Like, but anyway, you know?

• 30:35Ben Gilbert?

  Well, it just goes to show how silly the coalition building is. Like,

• 30:38Speaker 01

  It's totally silly, exactly.

• 30:39Ben Gilbert?

  The, the two-party system requires that if you feel very strongly about something, then you're not allowed to think independently about anything else.

• 30:47Speaker 01

  It's so crazy, you know? And I think what messes people up is the fact that I actually just think Donald Trump is a horrible human, who you should do no business with, has no business being in any political office, and, you know, is just horrible on any number of levels. But I believe that, independent of his party, he's a Democrat, obviously.

• 31:06David Rosenthal?

  Obviously, yeah.

• 31:06Speaker 01

  Yeah. And so, like, I would hate him as a Democrat or a Republican. So it's not personal, and I would, I would love to-

• 31:12David Rosenthal?

  Or it is personal with him, but it's not-

• 31:14Speaker 01

  It's very personal with him, yeah. I mean, I just think this is a, just horrible human being on, you know, in every way. Now, I understand for some people- He represents change. For some people, it's like the way the Republicans secured office and that's all they care about is winning. I get it, whatever.

• 31:30Ben Gilbert?

  And I think so much of the human condition is like being a part of a community. And he, for so many people, is a symbol that means, hey, all my friends and neighbors, we're, we get to agree on something so that we all can find togetherness in something. And for some people, that's the flat earth. And for other people, that's startups. And for some people, it's

• 31:52Speaker 01

  The tribe. Yeah, we don't, you know, a lot of people don't practice religion anymore. And so he's their religion. And Hillary Clinton, or Elizabeth Warren, or Bernie Sanders might be other religions.

• 32:02Ben Gilbert?

  Or the new iPhone. Like, I found myself ordering this phone, and I love it. And it's the iPhone 14 Pro, and it's magic and whatever. But like, it's not that different than my old phone. But I got to participate in all the fun, watching of the keynote, and the tweeting, and the nerding out. And like, let me look at the image quality versus the old one.

• 32:17David Rosenthal?

  I gotta say, it really is pretty.

• 32:19Ben Gilbert?

  It is pretty. But like, I got to be part of a tribe. And like, that is a thing that no matter what your tribe is, that is so fun to be there on Tribe Day and Tribe Week.

• 32:28Speaker 01

  I will say, the thing I'm proud about the show, I think, is that it has, you know, through a lot of the trials and tribulations, shown that you can be friends, disagree, learn from each other, and have a vibrant debate, which is how we all grew up, I think. When I say we, including you guys, but also specifically the besties, I want to be friends with people who I disagree with. I want to debate stuff, right? And then people are, like this guy, Dean Preston, and he's like, one of these supervisors here, he's a super idiot, like, guy in San Francisco, who like, you know, like, won't let them build housing and all that stuff. And he's like, you're just a conservative, blah, blah, blah. And I was like, you don't actually understand who I am. He's like, you're a conservative billionaire. I'm like, wrong, on both accounts. But thank you for the latter.

• 33:13David Rosenthal?

  My besties remind me on the latter.

• 33:15Speaker 01

  Yeah, I'm looking on it.

• 33:18Ben Gilbert?

  Not trying to be a billionaire. Thank you. 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.

• 33:34David 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.

• 33:48Ben 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.

• 33:58David 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.

• 34:16Ben 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.

• 34:32David 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.

• 34:49Ben 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?

• 34:58David 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. Another thing that's really fascinating to me about All In and you guys is...

• 35:15David Rosenthal?

  Before All In, and maybe it's still to a large extent, I feel like Silicon Valley has this weird relationship with money, like super weird relationship with money. Like, you know, remember there's a whole thing about like Zuck drove like an Acura SUV.

• 35:30Speaker 01

  Oh my God, that all came from David Filo and um David Filo and Jerry Yang were driving their old cars to work.

• 35:37David Rosenthal?

  Right, like the cool thing, like you, you could like make money, build a company, but like you never want it, like you never, and

• 35:42Speaker 01

  Be understated, yeah.

• 35:42David Rosenthal?

  You guys, I think are the first like, like you guys like, fuck, like we got a private jet, like that's fine, like, you know.

• 35:49Speaker 01

  I mean, listen, I, I, uh, uh, you know, yeah, I believe in capitalism. I think it's great if people create jobs and if they get rewards for doing so, like, fine. I, literally the book I'm writing, my second book right now I'm writing is about wealth and money. And like, but not like in my regard, but in a sort of like big picture societal regard. So I'm like literally been thinking about this topic a ton. And I think we worry a little bit too much about wealth creation with a small like outlier wealth creation. And we, we don't think enough about inspiring people to create companies and learn. And like,

• 36:29Speaker 01

  the time I create the most controversy is when I'm like, I believe anybody can do it. And people are like, you're so wrong. And I'm like, am I? Because I go on YouTube and you could type in any topic that you want to learn and you can learn it. And all the stuff that was at MIT where I never got to go and Stanford and Brown is online for free. And I listen to macroeconomic classes and AI classes. When I'm like, it's 10 o'clock at night and I'm doing my email, I'll just put one of those playlists on from MIT Open Courseware. And I'm like, I can't believe I can take a course at MIT for free anytime I want.

• 37:08David Rosenthal?

  And then you, you know, flip it, you can build a business there, like David Sandler over the Founders Podcast, like Mr. Beast, MKBHD, like, nobody gave these guys permission.

• 37:19Speaker 01

  Equitable.

• 37:19David Rosenthal?

  Yeah.

• 37:20Speaker 01

  But people want to spread a narrative that the world is unfair. And like I watched.

• 37:27Ben Gilbert?

  Well, I think the world.

• 37:28Speaker 01

  Become so fair and so just and so much information and opportunity become available that I'm like, wait a second, I could never figure out how a term sheet worked and nobody would share their term sheet. And now there are a thousand videos and blog posts on how to negotiate your term sheet.

• 37:44Ben Gilbert?

  The world is still unfair. I think, very. I think the key insight is like, recognize that the world is unfair and actually what that is, is a game on the field and figure out how to play the game on the field.

• 37:56Speaker 01

  But I mean, it's never been more fair. So the world is unfair. True statement. And in America, it's never been more fair. You can learn, Google has like five courses online. I think it's called Grow with Google or something where they're teaching how to be a UX designer, how to do this, how to do that. And it's free so that they can get more people to apply for jobs and the average job entry salary for these things is like 80K. So I, I find it's very weird in the world. I think there's like a group of people who want the world to be more unfair than it actually is because it makes them feel more virtue signaling goodness.

• 38:35Ben Gilbert?

  That's their community. That's how they find that there are other people who love that they tweet that the world is unfair. So they.

• 38:41Speaker 01

  And they have to, and it typically like is a certain type of person. I'll just leave it at that.

• 38:45Ben Gilbert?

  Okay. Can I, so I.

• 38:47Speaker 01

  I'm gonna leave it at that. But I teach Founder University now. I have a course where I teach people for 12 weeks. Um, or I should say I have a team that teaches it and I'm going to actually teach it myself, uh, this next cohort where I just teach people how to start companies.

• 38:59Ben Gilbert?

  All right. Let's plug it. How can they find out?

• 39:01Speaker 01

  Founder. University. That's it.

• 39:02Ben Gilbert?

  There you go.

• 39:03Speaker 01

  Yeah. I mean, it's basically, it's free. You, the way I did it was you apply. If you want to build a company, you pay 700 bucks. If you go and you get to week 12, we charge your stripe back, the card back, the 700 bucks. If you don't come, or if you don't have an excuse to absence, if people miss something because of their kids or whatever, fine. But we just try to get people to complete it. Over 90% of people complete it.

• 39:23Ben Gilbert?

  That's cool.

• 39:24Speaker 01

  So, and then we're investing 25K in some of those folks to help them start their companies. Like people don't know all the work I'm doing like quietly, but like 200 people go to this course now. Well, maybe I'll have 400 in the next cohort, the fourth cohort, we'll see. But you know, like people can learn how to create companies and they're like, no, they can't. And I'm like, yes, they can. You have to have gone to Stanford. I'm like, no, I've invested in 350 companies like. Maybe 5% of the founders went to Stanford. Like, no, that's just not, it's patently false. Like, you know, you have some confirmation bias. You're dealing with a data set from 10, 20 years ago. I get it. But I'm telling you, like, on the streets, ground level truth. We all meet with founders all day. It's never been more diverse. It's never been more open.

• 40:08Speaker 01

  Nobody cares where you went to school.

• 40:10David Rosenthal?

  Nobody cares where you live anymore.

• 40:11Speaker 01

  Nobody cares where you live. They care about what you've built and your traction. Like, it is post pandemic. All people care about is like, show me your metrics. Show me the product. Show me your team. What are your skills? Great, let's go. What's your growth rate? It's basically become like as beautiful of a meritocracy as I've ever seen. And man, you say the M word, it freaks people the fuck out. I'm like, why is this so scary for you that Silicon Valley is a meritocracy? And they're like, because it's not. And I'm like, it kinda is.

• 40:41Ben Gilbert?

  Can I, can I answer your question earlier of what, why I think All In works?

• 40:44Speaker 01

  Yes.

• 40:45Ben Gilbert?

  All right.

• 40:45Speaker 01

  Go ahead.

• 40:46Ben Gilbert?

  So I think you're the, you've got the perfect storm of three things. The first thing is

• 40:51Speaker 01

  A lot of theories on this out there, by the way.

• 40:52Ben Gilbert?

  Billionaire porn. Most people, you're counter positioned. Most people who attain that level of wealth crawl into a quiet hole and make sure no one knows

• 41:03David Rosenthal?

  You're doing shows from boats and jets.

• 41:05Ben Gilbert?

  Yeah, so there's like

• 41:06Speaker 01

  I don't think we've done one from a jet, but yeah, there was definitely two boats in the last two years. That's true. Not my boat.

• 41:13Ben Gilbert?

  In some peak moments of All In, it's like watching billions in real life. It's like you hear, you hear Chamath talk about this spread trade and you're like, this guy's got a lot of money on that spread trade. And like, does he actually have a key insight here? Or is he, and like, there's, there's this interesting intrigue there. So bucket one is like billionaire porn. Bucket two is, uh, by the research you guys do and, and the folks that you each work with, because there's definitely researchers that seem to be involved. You bring things to the table that are like, brand new insights that aren't widely available yet. So I feel like I was learning things about COVID-19 on All In that I wasn't getting through any other source. I'm like, somehow this is not making it to me.

• 41:55Ben Gilbert?

  And this feels very, like, a lot of it proved out to be like, this was good information before it was mass

• 42:01Speaker 01

  All four of us are information junkies with a lot of research and teams that could inform us.

• 42:06David Rosenthal?

  How many people, All In, how many people touch an episode of All In?

• 42:11Speaker 01

  One. Producer Nick, that's it?

• 42:13David Rosenthal?

  No, I mean, but like the research.

• 42:15Speaker 01

  I don't know. I'm pretty sure.

• 42:17Ben Gilbert?

  There are text files open on people's computers when they're talking.

• 42:21Speaker 01

  We have a docket with the notes, but that's mainly for me to queue it up. Like, I just read the four or five bullet points so people know it. So I do that with my team, the docket. But the docket is built from, you know, the five or six stories that people submit to our group chat and say, "Hey, put this on the docket."

• 42:34Ben Gilbert?

  Right.

• 42:35Speaker 01

  And I think Saks has some research help. I'm sure Friedberg and Chamoff read the stories or they're well-read. And all of us read constantly and we're in the information business of talking to people about the world. So you guys are investors. You know how it is. Like, you do 20 meetings a week with founders. They're going to tell you everything about the world.

• 42:58Ben Gilbert?

  You're in the fold.

• 42:58Speaker 01

  And you guys are young still, but, you know, imagine you do that for 20 years. Like, you're going to get smart or you're a journalist for 20 years. You're going to get pretty... I wouldn't necessarily say smart, but you'll be informed.

• 43:07Ben Gilbert?

  And if you're hearing the right pitches, you actually are getting, like, cutting-edge information before it's widely available.

• 43:12Speaker 01

  Definitely. So, okay, that's number two. Yeah, we probably have a slight information edge.

• 43:16Ben Gilbert?

  Yeah.

• 43:17Speaker 01

  Certainly a huge... I will say, the information edge compared to journalists having been... This is not a dig to my journalist friends. I was a journalist. I had 75 people at the magazine. We were always trying to figure out from the principles what was going on and tell that story. But we were only as good as our access to information. And we probably... Now, looking back on it, I think we had between 5 and 35% of a story. And I know that's, like, probably triggering to a lot of journalists that they have that little information.

• 43:47David Rosenthal?

  Well, you weren't on the inside.

• 43:48Speaker 01

  But you weren't on the inside. So when you're on the inside, you have 100%, or even on the inside, you might only have 50%, depending.

• 43:53Ben Gilbert?

  You get enough to run with and you feel like, okay, now there's enough story here. Let's do it. And like, that's clearly not the whole story, but it's enough to put the piece together.

• 44:01Speaker 01

  You're trying... And then, over time, process journalism, as some people have dubbed it, you know, maybe the six or seven stories will tell the full story.

• 44:08Ben Gilbert?

  Yep.

• 44:10Speaker 01

  Which the third component, you think makes it successful?

• 44:13Ben Gilbert?

  It's the thing that David and I took forever to realize works about acquired, which is relationship and charisma.

• 44:18Speaker 01

  Yes.

• 44:18Ben Gilbert?

  Like, people like having fun by listening to stuff.

• 44:21Speaker 01

  Sure.

• 44:21Ben Gilbert?

  And so, like, if we can make history fun, then

• 44:27Speaker 01

  A little bit of joy goes a long way.

• 44:28Ben Gilbert?

  Four hours of us diving into stuff you would never read in a book. And you guys do that in spades. Like, it is just so fun to, like, temporarily join your world.

• 44:38Speaker 01

  I mean, the fact that you, as a podcaster who makes elite content, like, top 1% content, find it compelling is just, yeah, that's very...

• 44:47David Rosenthal?

  Listen every week. Don't miss it.

• 44:49Speaker 01

  I can't believe it.

• 44:50David Rosenthal?

  Literally walking the baby up and down the hills, listening to...

• 44:52Speaker 01

  I mean, I have people tell me they listen to it twice. They take notes. I'm like, wow, that's great. You know, I...

• 44:57David Rosenthal?

  Maybe I should take notes.

• 44:58Speaker 01

  Well, anyway, I was very intentional with my role in it to step back and be like the point guard. But, you know, I'm a shooting guard too, so sometimes I will want to shoot the ball, and I can do both. I'm a combo guard.

• 45:13David Rosenthal?

  How did the Free Bird Host episode come about? So, one week, you've switched roles.

• 45:20Speaker 01

  Well, he was like, "I think this could be done better. This could be better." And I was like, "Go ahead." And I just said, "Sure, I'll just shoot."

• 45:28Speaker 01

  And...

• 45:28David Rosenthal?

  You pass the rock, and I'll...

• 45:30Speaker 01

  I was like, "Yeah, you want to be a point guard? Go ahead, sure." And he did a solid job. But let's be honest, like...

• 45:34Ben Gilbert?

  It's not a point guard.

• 45:36Speaker 01

  It's not Showtime, that's for sure. Like, I don't think people are gonna go to watch him play point guard. I mean, he did a serviceable job.

• 45:46Ben Gilbert?

  Put that on his tombstone.

• 45:47Speaker 01

  No. But he shines when I created Science Quarter for him to shine. I said, "Bring me a sign." He's like, "Oh, you know, I don't know if I want to talk about politics." I was like, "Listen, Sacks wants to talk about current events, politics. I'm giving him his red meat. Here's your quinoa." Come to me with a science story, you know, and we'll do this quinoa corner kind of thing. And I've made him the Sultan of Science. So good. You know, it was, it was a distinct effort. I really wanted to make him shine, you know, and it worked. You know, it worked because you see how engaged he is. And what used to happen was, and fans know this, I'm not speaking out of school here, you see it every episode. Sacks would disengage during science and quinoa. Disengage during? During politics. And what I've been trying to do is keep both of them involved.

• 46:31Speaker 01

  When the other is doing stuff and Chamath and I are involved.

• 46:34Ben Gilbert?

  That's a hard job.

• 46:35Speaker 01

  Yeah, I studied, I studied the McLaughlin Group. People don't know this, but I went back to look at McLaughlin and I watched him moderate. So people, there's a big debate. Do I interrupt too much or not enough? Do my interruptions, I call them interjections, uh, do they help? And I actually looked at the interjections and if you look at McLaughlin, you guys did not grow up on McLaughlin.

• 46:59Ben Gilbert?

  Super unfamiliar.

• 47:00Speaker 01

  So the McLaughlin Group was like the best Sunday morning show. And like, it was so good, like SNL would parody McLaughlin. It probably had a million people watching it, but this guy McLaughlin was like, pretty cantankerous. And if he didn't like what people would say, he'd be like, wrong. This is the answer, you know, like, and it became so competitive that you wanted to watch it. Yeah. Now, what I didn't realize by adopting that would be that Sacks is the ultimate debater. And will fight like a dog until he wins any debate. And so I may have pushed Sacks into more of a debate situation where I'm trying to not have it be a debate. I'm trying to have it be a conversation. So what I've been working on is trying to keep it be a conversation.

• 47:43Speaker 01

  And then the, some people in the audience are like, you have to be the fact checker for Sacks. And I'm like, no, that's not my role. I'm not real time fact checking Sacks. And so that is a delicate balance of like, and then sometimes I'll ask questions. Specifically because I know the audience doesn't know what, you know, fair market value when they hear an acronym means. So I'm like, explain that.

• 48:04Ben Gilbert?

  Right.

• 48:05Speaker 01

  And I'll stop somebody now.

• 48:06Ben Gilbert?

  I mean, you're, you're expanding the tam to dentists, like that's.

• 48:09Speaker 01

  Correct. Thank you. So people are like, oh, J. Kyle's an idiot. He doesn't know that term. Or I say to somebody, can you unpack that? Can you explain that?

• 48:17David Rosenthal?

  Obviously, you know that term.

• 48:18Speaker 01

  Doing that for myself.

• 48:19David Rosenthal?

  You were what, the third or fourth investor in Uber?

• 48:21Speaker 01

  Yeah, like, exactly. Well played.

• 48:24Ben Gilbert?

  I think he's been in Robin Hood, too.

• 48:25David Rosenthal?

  Oh, gone, too?

• 48:26Speaker 01

  Wow, who knows? And I'm like, dude, like, I'm asking that question on behalf of the audience. So when I'm moderating.

• 48:33Ben Gilbert?

  Yeah.

• 48:33Speaker 01

  As opposed to being an interviewer, or as opposed when I'm working with Molly, and we're chopping up the news, when I'm the shooter there, right? And she's maybe playing point guard a little bit, and I'm shooting, and then sometimes I'll pass it to her and she shoots. Like, I can travel between those roles. And, you know, in that role, I'm acting on behalf of the audience. And I get the sense, like, he's going, Chamat's going too fast. They don't know what the spread trade is. Let me pause. Can you explain one more time? Or let me reflect back to you. Is this what a spread trade is? And he's like, almost, this. And that's what I think has brought in, to your point, a lot of the dentist crowd.

• 49:07Ben Gilbert?

  And having an intimate sense of where your audience's edges are is, is a really important role there. Like, when we have guests on, I'm always trying to catch.

• 49:16Speaker 01

  Yes.

• 49:17Ben Gilbert?

  Where, where do they just go slightly too deep? And I need to pull them up, so that we...

• 49:21Speaker 01

  Yeah, and, and, you know, podcasting is about going deep. So it is really an art. Like, do you want to stop somebody when they're going down this, like, crazy rabbit hole?

• 49:29David Rosenthal?

  There's no clock in this room.

• 49:30Speaker 01

  Well, they're going down some rabbit hole that has never existed in media before.

• 49:34Ben Gilbert?

  Right.

• 49:35Speaker 01

  So...

• 49:35Ben Gilbert?

  And you want to let them go, but you need to make sure they're taking the stairs. Because like, if they just jump in, you're like, oh, God, no one has any context. They can't learn anything new, because you're like, you're not connecting it to something they understand.

• 49:45Speaker 01

  They just jumped into brain surgery. And you're like, let's just explain to us what's going on here. How are we going to chop up this brain?

• 49:50Ben Gilbert?

  Right.

• 49:51Speaker 01

  Like, yeah. Yeah, it's a, it's a bit of an art. But, you know, I have to say, like, it's, it's been a different muscle for me to flex. And it's been great fun for me.

• 49:59Ben Gilbert?

  The other thing, like, I don't know if you think about it on this axis at all, but like, I kind of think of there's, I used to think it was very binary. Like, there's two categories of podcasts. There's candy and there's vegetables. And like, I listen to the audio version of Stratechery, and that's my vegetables. And it's not like, deeply, it's enjoyable intellectually, but it's not like fun. And, um... I I can't, I certainly can't be doing anything else with the language center in my brain while I'm listening to that. I have to be like on a run and like sometimes even at home so I can take some notes or look something up. I can be cleaning.

• 50:33Speaker 01

  It's a pause type podcast. You have pauses sometimes. Sometimes you hit and rewind.

• 50:37Ben Gilbert?

  Right.

• 50:37Speaker 01

  Let me make sure I get what he's saying here.

• 50:39Ben Gilbert?

  Or I can listen to the talk show with John Gruber and it's just like if I missed out on 20 minutes because I was like brushing my teeth and then I left the room and I came back and I'm like, oh, I didn't actually miss anything because this has just been like, it's comforting.

• 50:52Speaker 01

  Yeah.

• 50:52Ben Gilbert?

  It's like, I love all the stuff he's talking about, but like, it's not must-listen every time, every minute, every second concept. And I'm not using hard parts of my brain to understand.

• 51:02David Rosenthal?

  But all in has become candid vegetables.

• 51:04Ben Gilbert?

  It's both.

• 51:05Speaker 01

  It's both, yeah, for sure. Yeah, I try to do with this week in startups and all in is try to have it be both. A little bit of personality, a little bit of entertainment, some fun hot takes. Yeah.

• 51:14David Rosenthal?

  Right.

• 51:14Speaker 01

  I mean.

• 51:15David Rosenthal?

  Related, but separate topic. Silicon Valley.

• 51:20Speaker 01

  Yeah.

• 51:20David Rosenthal?

  I feel like, especially there's a lot of, part of the, even the origins of all in, there's a lot of like bashing on San Francisco politics and Calvin. Like, there's a lot of crap wrong here.

• 51:29Speaker 01

  Yeah.

• 51:29David Rosenthal?

  But you guys are all still here. How are you guys feeling about that?

• 51:33Speaker 01

  For now.

• 51:33David Rosenthal?

  Yeah. How do you, how do you feel about that? Like, what do you think of the Bay Area?

• 51:36Speaker 01

  Um, you know, I lived in New York, Brooklyn, then Manhattan, and then I lived in LA, and then I lived here. And so I think my, I'm moving to places I enjoy less and less each time. I enjoy Brooklyn and Manhattan much more than LA. I enjoy LA much more than San Francisco. So I don't know where to go next, but I'm gonna go somewhere.

• 51:57David Rosenthal?

  Which, so why are you still here then?

• 51:59Speaker 01

  Uh, well, I can't.

• 52:00David Rosenthal?

  There's no reason for you to be, is there?

• 52:01Speaker 01

  I came up here because I had a lot of friends up here. And I had done LA. And I was like, I wonder how far, you know, I'd been a Sequoia scout. And then I was like, my friends are telling me I could start a venture fund. You kind of need to be up there. I wonder how I would do if I was up there in the industry. And I was kind of this like-

• 52:18Ben Gilbert?

  Because if you wouldn't, you'd always wonder.

• 52:19Speaker 01

  Well, Michael Maress used to call me the mouth from the south. Because they had like two investments in LA. He's like, "Oh, the mouth from the south is it." What have you had in your day, Cal?

• 52:29David Rosenthal?

  Sir Michael saying that.

• 52:30Speaker 01

  But I moved up here and I love it up here. It's quite bucolic. My kids are loving it. It's quite nice. I would love to live in another city in my life or two. I could see myself in Austin or Miami. I like both of those cities. I think Austin's kind of the future. I think California is going to be damaged for a decade or two. So I think for the rest of our adult lives, this town-

• 52:53David Rosenthal?

  Because of the pandemic, or?

• 52:55Speaker 01

  I think the politics and not appreciating, the politics, the regulation and not appreciating

• 53:03Speaker 01

  the tech industry is really the problem. And then you look at this guy Dean Preston, like he is dunking on the founder of Away and Stuart Butterfield from Slack. They're a couple. And he's like, "We got a million, two out of them when they sold their homes." And I'm like, "And you also lost two incredible founders who've created billions of, tens of billions of dollars of wealth for San Francisco, you idiot." And like, at the same time, Francis Suarez in Miami is listing all of the venture capital and doing a tweet storm about all the companies that raised venture capital. So you have one guy, Dean Preston, dunking on people saying, "We have this 1%. So when they sold their $30 million house, we were able to extract a million, two. That's why tech doesn't like me." And I was like, "Hey, dummy."

• 53:46David Rosenthal?

  Yeah, now that all the future earnings are gone. Now, what's, uh, California marginal tax rate is 13.3%.

• 53:54Speaker 01

  I mean, but just, they have an exit tax now for homes in San Francisco. So if your home costs over 10 million, when you sell it, I mean, I think it's just a sales tax.

• 54:02David Rosenthal?

  1.2 million from them selling their home versus 13% of their future earnings stream is like-

• 54:08Speaker 01

  Literally, the chef at Slack made a billion, two, paid a billion, two in taxes from their RSUs. Like, are you such a, where do you think you got this certain- Probably, yeah. Like, the million, two-

• 54:20Ben Gilbert?

  Yeah, but that order, I think, too.

• 54:21Speaker 01

  Probably paid in taxes on their RSUs at Slack.

• 54:25David Rosenthal?

  Yeah.

• 54:26Speaker 01

  You absolute moron. Like, you're literally so upset about their mansion and dunking, and you're dunking on an individual's name. But anyway, the fact that we hate entrepreneurs who create jobs and wealth, or certain people do, is just insane. It's just insane. Like, I mean, you could go change the tax code. It's fine. Like, you know, raise the minimum wage. Like Bernie Sanders and Elizabeth Warren attacking Bezos endlessly, and then Amazon starts paying 22 an hour, gives you benefits, and pays for your college. And it's like, okay, hold on a second. I know what Bezos just did. He took the platform that you could never actually enact, and

• 55:10Speaker 01

  he enacted it inside of Amazon. If it's not perfectly clear what just happened, literally, he's dunking on you. You wanted free college and couldn't get it done. He gave it to Amazon employees. You wanted a $15 minimum wage. He made it 22. And you wanted everybody to have universal healthcare, and he gave universal healthcare. Like, that is literally what Bezos did to them. How embarrassing for them.

• 55:32David Rosenthal?

  Maybe you could argue that, like, them pushing and pushing it, but...

• 55:34Speaker 01

  No, no. Definitely, it is literally him showing, like, as the Amazon crew showing, like, let the free markets work. Like, the DoorDash, Uber, Amazon, Starbucks, absolute race and battle to just hire entry-level employees and make it delightful for them is what has driven, and a lack of immigration, is what has driven these salaries up, right? And the benefits up. It's extraordinary what's happened with the free market.

• 56:08David Rosenthal?

  There's competition.

• 56:09Speaker 01

  The minimum wage is still $7. Federal minimum wage is $7 and change still, right? And 15 here in the city. In New York, it's 15. Like, yeah, it's weird.

• 56:19Ben Gilbert?

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

• 56:32David 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. Legora took that insight and asked the question, what if you really built something with that power from the ground up for the legal industry?

• 56:49Ben 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.

• 57:04David 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.

• 57:28Ben 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.

• 57:47David 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.

• 58:17Ben 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.

• 58:42David Rosenthal?

  We referenced this at the start of our conversation. You're working as hard or harder than you ever have. You said you've got a

• 58:48Speaker 01

  Smarter.

• 58:49David Rosenthal?

  A new well of energy.

• 58:51Speaker 01

  Yes.

• 58:52David Rosenthal?

  Tell us about it.

• 58:54Speaker 01

  Well, I find great purpose in what I do. And when my friend Tony Hsieh died, I really thought deeply about like what I wanted to get out of the rest of my life. And I realized like, these are the things I really love doing. And these are things maybe not so much. And I just realigned my life over the last two years.

• 59:14Ben Gilbert?

  So what are the

• 59:15David Rosenthal?

  We're one of the two buckets.

• 59:16Speaker 01

  Yeah, exactly. So I can tell you the things that just to me, I'm just not going to get any pleasure about in life. Working like, no offense to my incredible lawyers, but negotiating term sheets and legal and HR issues and accounting and operations and tax and you know, that entire stack of things. Not fun to me. Not fun at all.

• 59:35Ben Gilbert?

  And I'm sure you never viewed that as fun, but at least before you were like, I'm willing to put up with it because it may, maybe it's a thing that creates value enough for me to do it.

• 59:43Speaker 01

  Doing my podcast every day. Absolute joy. Entertaining an audience, you know, thinking, thinking about the world and having these conversations. I had Toby from Shopify on today. Like I leave the Toby interview. It's like his third or fourth time on the pod.

• 59:57Ben Gilbert?

  That's awesome.

• 59:58Speaker 01

  And it's just like, instead of us having dinner or lunch, we just record a pod. The end.

• 1:00:03Ben Gilbert?

  Did you do it in person or did he?

• 1:00:04Speaker 01

  No, just popped on Zoom. You know, I had to start it because he did that tweet about his compensation tool where, you know, here's your total comp.

• 1:00:11David Rosenthal?

  You can use the slider.

• 1:00:12Speaker 01

  I was like, that's brilliant. Come on the show. Want to come on the show and talk about it? I was like, yeah, of course. And so like those conversations, I just looked at them and I'm like, my energy coming out of the show is on 11. Why am I not doing this every day? And I watched Howard Stern when I was a kid or Charlie Rose do it day in and day out. And I was like, I could be like those guys. They every day get on there.

• 1:00:39Speaker 01

  And they seem to love it. And I do. And so I just committed to doing it every day. And I love it.

• 1:00:44Ben Gilbert?

  Isn't it weird when there's something that takes a ton of work, but somehow doesn't drain you?

• 1:00:50Speaker 01

  Not at all. To me, it's like going to the gym. It's like working out or having dinner. It's just something I do every day. That gives me great joy. And then that's I recruited Molly. I was like, I need somebody to do this with me every day.

• 1:00:59Ben Gilbert?

  Oh, yeah.

• 1:01:00Speaker 01

  Who I respect and who's awesome and bring something to the table that I don't have.

• 1:01:03Ben Gilbert?

  And having She's so great. Having someone to play off of.

• 1:01:05Speaker 01

  Sure.

• 1:01:05Ben Gilbert?

  I feel like that's the thing that's kept acquired going.

• 1:01:08Speaker 01

  Yeah.

• 1:01:08Ben Gilbert?

  Is that like you and I can like I don't know how you did it alone for I don't know. A decade.

• 1:01:13Speaker 01

  Uh, well, I, you know, I'd have guests on. It was largely a guest driven show. And then I would do the news roundtable once a week because it was once a week, then twice a week, then three times a week. And then I was like, well, however many I just allow, I'll do it five, six days a week, whatever. Um, and, um, I enjoy meeting with founders, uh, when they fit a certain profile. Uh, but it's very hard to meet with a large number of founders, given how many are coming in. And it's hard to work with them when they're just talkers.

• 1:01:41Ben Gilbert?

  Yeah.

• 1:01:42Speaker 01

  To me, that's a very hard part of the job because it becomes very repetitive.

• 1:01:46Ben Gilbert?

  So how have you exercised that?

• 1:01:47Speaker 01

  Well, I created a platform, Founder University, where if you want to build something, I will talk myself to 200 people. You can build and then whatever arises as the performance and the product, you know, and they, as people move from talkers to the walkers to from, you know, when they actually start building stuff, that's when I get great joy. And so I'm like, bring me the people who have product velocity. So I told my team, listen, you're doing, my team does six, people don't understand the scale of the business I have. Nobody's

• 1:02:19Ben Gilbert?

  Yeah, I don't.

• 1:02:19Speaker 01

  Really understands what I'm doing and I, I kind of like it that way, but the angel syndicate is now the largest syndicate in the world. I've deployed like a hundred eighty five million dollars in my career as an angel investor, doing 50 million a year now.

• 1:02:31Ben Gilbert?

  That's awesome.

• 1:02:32Speaker 01

  I'm raising the fourth fund in public, like 11,000 angels in the syndicate. Like this is going at a really significant velocity. If you were to look at the slope. It's not quite a hockey stick, but it's hockey stick-esque in terms of the total capital I've deployed. And it's in really high-quality companies I'm getting better at. There's 11, I have 22 people, and 10 on the media side, 12 on the investment side. And of the investment team, like, people don't understand, they're like, "Oh, you're a solo GP." I'm like, "Yeah, but 12 people." Those people are doing 60 introductory meetings per week, 6-0. And then we're doing maybe 15, 20 second meetings. So there's, it'll be 100 meetings a week shortly, probably. Okay, fine.

• 1:03:10Ben Gilbert?

  Plus 10 people, or 12 people.

• 1:03:12David Rosenthal?

  But you're not doing the...

• 1:03:13Speaker 01

  I'm not doing them. And what happens is...

• 1:03:15David Rosenthal?

  You had this line, was it on, it was on Twist, I think?

• 1:03:18Speaker 01

  Not for me.

• 1:03:18David Rosenthal?

  You know, like, people say, "That's a lot of work," but you're like, "Yeah, but not for me."

• 1:03:21Speaker 01

  That is the new philosophy. This is why my energy is really high.

• 1:03:25David Rosenthal?

  This is your unlock.

• 1:03:26Speaker 01

  I have told everybody who comes to work for me, "I work 60, 70 hours a week. Keep up.

• 1:03:32Speaker 01

  If you can't keep up, don't be here." I'm looking for, you know, a fixed 50, a solid 60 hours a week. If you want, you don't have to match me 67, but 60 or 70 hours a week, but keep up.

• 1:03:42Ben Gilbert?

  And are you looking, in that team, are you looking for, like, the next Jason Calacanis to be a part of that team? Or is it like, someone who likes doing that part, like, that's, well, let me ask it more directly. Is it someone who's content with doing this, or are you looking for people that are, like, hungry enough to be the next Jason?

• 1:03:59Speaker 01

  I'm open to all of it. I'm open to all of it. I don't, they don't need to want to have my, you know, absurd, unhealthy desire in my youth to be successful. And if they did, they probably wouldn't come work for me, but maybe they would. Actually, I would. So, yeah, they probably would.

• 1:04:16David Rosenthal?

  Not for very long.

• 1:04:17Speaker 01

  Yeah, mine might be like, three years.

• 1:04:19Ben Gilbert?

  You'd come, you'd learn, you'd extract.

• 1:04:19Speaker 01

  It's down five with two. If people come and they work for two, three, four years, and they go start their own venture fund, or whatever, muscle talk, it's great. But what I told them was, you know, "Just find the great companies." And I looked at investment team meetings, usually they're Monday. People do it for an hour or two, and then they go to lunch. I said, "I want to do it twice a week, Tuesday and Thursday, it's 2 to 4 p.m." Hit me with companies. So that was another innovation I did. And I also brought Mike Savino, who was my first boss when I was in my 20s, doing IT, and I brought him on as president. So this is like, one of my lifelong best friends. And I said, "Run the company. Here's what I want to do. The podcast, meet with founders, do the LP fundraising, that's it."

• 1:05:01Ben Gilbert?

  Ooh, are you enjoying the LP fundraising?

• 1:05:03Speaker 01

  I am now, yeah. I'm, I'm kind of like... Uh, remember in X, I don't know if you watch Billions? Oh, yeah. Every episode. Great. So you know, like at some point, um, uh, he was like, I'm gonna go raise money. Yeah, it's cap raise time. It's cap raise time. And like Wags is like, so I got my Wags, Mike Savino's my Wags. Yeah. And I got my Wags who just fixes everything. And I'm like, I'm gonna go raise money. And so I literally was like, we're doing 506C. And they're like, don't do that.

• 1:05:31David Rosenthal?

  You're now, you were in kind of this one bucket with your capital. And now you're going simultaneously in two directions of you want the public and you want the big institutions, right?

• 1:05:42Speaker 01

  We'll see. Um, I've had select institutions make small bets. The first fund was 10, the next fund was 11. And then the last fund was 44 million. The first fund I deployed in five years, second fund, two years, the third fund, two and a half.

• 1:05:55David Rosenthal?

  Five years?

• 1:05:56Speaker 01

  I was just, that was my first fund. It was, you know, me, Bill Gurley, Dave Goldberg, rest in peace, Tony Shay, rest in peace, David Sacks, Chamath. Just a bunch of my friends put money in and it was to see if I wanted to be a venture capitalist and do this as a career. And I was like, yeah, I just did it over five years. And the second one, I raised 11. Took me six months to a year to raise the first. It took me, the second one took three to six months. The, no, it took six months. The third one took me three months to six months. And in this one, I, I think I'll wind up raising in the first 10 days what I raised in the first, yeah, a couple of funds.

• 1:06:36David Rosenthal?

  Wow.

• 1:06:37Speaker 01

  I literally did two webinars, a couple of hundred people came to each. So for people who are listening, 506C is you can raise in public. Which means you just can tell people, I'm raising a fund. And I was like, well, I'm doing all in. It doesn't make any money. I have this week in startups and I watched a bunch of these young, um, aspiring VCs raise publicly.

• 1:06:56David Rosenthal?

  Right.

• 1:06:57Speaker 01

  You didn't raise publicly.

• 1:06:58David Rosenthal?

  No.

• 1:06:59Speaker 01

  You did private.

• 1:07:00David Rosenthal?

  Thought about it, but for a whole bunch of reasons.

• 1:07:02Speaker 01

  Well, it's kind of scary because people don't do it. But if you have no track record and you want to raise, so like this guy, Mac the VC.

• 1:07:11David Rosenthal?

  Yeah, you did a great episode with him.

• 1:07:12Speaker 01

  Yeah, it was great. I had him on, like, you know, first time founders for a season of Angel. It's like a subsection of the This Week in Service podcast. And I became an LP in this fund and he just saw me like I just did like hundreds of meetings. I did like five meetings a day for a year and I raised my whatever 10 million dollars. And he's African American and he's like, it's just a matter of how hard do you want to work? And I'm like, careful saying that publicly because there's a group of people who do not want you saying that. He's like, no, it's just all you have to do is like you go to Angelish, you set it up and then you just start talking to other VCs. You talk to them and you just have to be willing to take 50 meetings a week. I'm like, dude, do not say that it's easy to raise a venture fund as a black man in Silicon Valley. But that's the position is it's not that it's easy, but that it's possible.

• 1:07:55David Rosenthal?

  You find your people who believe that with you and then they believe in you and then they back you.

• 1:07:58Speaker 01

  Correct, correct, correct. And so the whole thing, but what I noted when I was taking my notes, watching him was so many times people like, oh, you're, when's your next fund? I'm like, three years. They're like, oh, let me know. And I'm like, okay.

• 1:08:12Ben Gilbert?

  Right. Oh, I'll put that right there in the place where I keep everyone who tells me.

• 1:08:16Speaker 01

  Yeah, three years from now, what to do. Yeah. And so, you know, I mentioned it on All In, I tweeted it and all of a sudden, you know, I had a thousand people sign up.

• 1:08:25David Rosenthal?

  Is there a limit to the number of LPs you can have?

• 1:08:27Speaker 01

  Of course, yeah. It's 250 accredited, up to 10 million and then 2,000 QPs. And so it's, it's, it's a lot more work.

• 1:08:34Ben Gilbert?

  And, and QPs.

• 1:08:35David Rosenthal?

  Not for you.

• 1:08:36Speaker 01

  But not for me. Qualified purchasers, people who have.

• 1:08:39David Rosenthal?

  Look at you playing Jason. I know you know what a QP is.

• 1:08:42Ben Gilbert?

  I just wanted to dish the ball.

• 1:08:43Speaker 01

  I think it's five million in investable assets, like, and then accredited now is 200 if you're an individual for the last two years, each of the last two years and 300 if you're a couple, each of the last two years in income or a million dollars.

• 1:08:55Ben Gilbert?

  In net worth.

• 1:08:56Speaker 01

  In net worth outside of your primary residence. So there's a whole, and these things are going to change over time. But I believe that we're going to have a test for accreditation and you'll be able to be sophisticated if you take a course. So I think that's coming in the coming years. So just like I democratized Angel Investing, wrote the book Angel, was the first syndicate on Angel List, the most successful syndicate on Angel List, created my own, got the domain name, the syndicate, created the largest one, have done 265 syndicate deals by far like the largest amount of anybody, I think. I don't know.

• 1:09:25David Rosenthal?

  Which these, I mean, now as a participant of the Fund on Angel List, like, these are like, those are big numbers, like.

• 1:09:31Speaker 01

  You do something consistently.

• 1:09:32David Rosenthal?

  Four SPVs on Angel List, and we have the fund too, but like, you know, yeah, like, that's a lot.

• 1:09:37Speaker 01

  You're herding cats. You need to have a lot of people. But anyway, putting all that together, I think now's the time to democratize venture capital. So that's what I'm attempting to do here, is I want more people who are accredited and qualified purchasers who've never been in a venture fund to look at the asset class and just consider it. It's high risk, it's high reward. I'm in 20 venture funds myself, including yours.

• 1:09:58David Rosenthal?

  Thank you.

• 1:09:59Speaker 01

  And I'm sure.

• 1:10:00Ben Gilbert?

  But don't, but don't pitch Jason.

• 1:10:01Speaker 01

  I'm sure I will do yours. No, I mean, I'm just gonna pick them based on people I know, or people I know online, or put on a pod, and, you know, I'll do one or two new ones a year, and.

• 1:10:12David Rosenthal?

  Well, this is kind of to the conversation earlier, like, on the internet, this is the democratizing thing. Nobody's gonna just give you, if you just, you know, nobody's gonna just invest in your fund, but if you go do stuff.

• 1:10:21Speaker 01

  Yes.

• 1:10:22David Rosenthal?

  And then people are like, oh, Jason does stuff. Great, I'm gonna back Jason. Ben does stuff, like.

• 1:10:26Speaker 01

  Be of action, yeah. And it doesn't mean you have to start a pockets. You could be a blog, you could do events, you could create Founder University, whatever it is. You can do any of those things. You can have a track where you can be an advisor to startups, whatever it is.

• 1:10:38Ben Gilbert?

  Do you like the idea, I'm curious, as someone that's always raised from sort of individuals, do you, do you like the idea of having some institution be like, can we invest $15 million?

• 1:10:48Speaker 01

  Oh, yeah, of course. I mean, I've had five, you know, million dollar checks, $10 million checks in the fund, from institute, from, you know, fund to funds and institutions you know. But I would very much at some point, I don't need it, but it would be meaningful for me, both my parents are cancer survivors, to have Memorial Sloan-Kettering's endowment, or an endowment.

• 1:11:08David Rosenthal?

  UCF or something like that.

• 1:11:09Speaker 01

  Yeah, somebody like that, you know, if they wanted, I would work, you know, really hard to try to get them a great return. I would find more, I would find even more meaning in what I do.

• 1:11:19David Rosenthal?

  Yep.

• 1:11:20Speaker 01

  And, you know, I got that from Sequoia, like, you know, they would have this Sequoia Dinner every year for the founders, and they would say, here are what the foundations, who are LPs, are doing with the money you made for them with your companies.

• 1:11:32Ben Gilbert?

  Yeah.

• 1:11:32Speaker 01

  Click, click, here's what four foundations are doing, here's what this foundation's doing, and you're just like.

• 1:11:36David Rosenthal?

  Their conference rooms are named after their LPs.

• 1:11:38Speaker 01

  And the conferences are famously named after them, it's like.

• 1:11:40Ben Gilbert?

  And this is real.

• 1:11:40Speaker 01

  Powerful.

• 1:11:41Ben Gilbert?

  Like, I find we have, like, state pension funds and stuff like that.

• 1:11:44Speaker 01

  And that'll make you get.

• 1:11:45Ben Gilbert?

  In PSL Ventures, and like. You take it much more seriously. You're like, I am, it's because it's not just about the reward. It's not like, oh, I'm so excited about what we're going to do for them. It's like,

• 1:11:58Ben Gilbert?

  this is really important to preserve and not grow, but like preserve this capital.

• 1:12:03Speaker 01

  Yeah, yeah.

• 1:12:04Ben Gilbert?

  Which the psychology of doing that while you're taking big swings with asymmetric upside, that's that I find to be a fascinating dance.

• 1:12:12Speaker 01

  That was like one of the seasons of that of Billions was he's like, I'm going to be a family office. No, I'm going to raise my own fund, right? And so there's this natural tension for acts like, which should it be? And he decided, yeah, I like when I have other people's money because he he seemed to perceive like.

• 1:12:31Ben Gilbert?

  I think he felt that he wasn't a somebody in his ecosystem, in his community without managing outside capital.

• 1:12:37Speaker 01

  I think it's like playing, you know, in the bubble with nobody in the stands versus

• 1:12:41Ben Gilbert?

  Right.

• 1:12:42Speaker 01

  getting on the court at Madison Square Garden and there's people in the stands.

• 1:12:45Ben Gilbert?

  Your returns, your numbers don't mean anything unless you're putting them up for.

• 1:12:48Speaker 01

  Dude, I'm doing this public, or I should say quasi-public, people still have to sign up to, you know, come to a webinar. But I'm sharing with them like, here's my, the totality of my investments and here's what I've done. And here's what I plan on doing with my team. So, you know, I'm kind of enjoying it. And if, you know, I've met with all the top endowments in the world over the years and they're very kind to me, but it's always been like solo GP is a blocker, no track.

• 1:13:16David Rosenthal?

  Your fund is so small. We're a $50 billion endowment.

• 1:13:20Speaker 01

  Yeah. And you know, like, you know, at some point, like one of the ones who's the most rigorous, I wouldn't say exactly which one was like, we have a lot of respect for you. We know who you are. People would like you to sign a book and take a selfie with you when you're here. But I just want to be straight with you. We don't add many funds. And if you go through our process, it's going to take a lot of your time. And it's going to result in you not getting our money this time. I don't want to put you through that, but I respect you. And if you want to do it. We'll do it, but maybe just put one more fund on the board and let's talk in the next one. And I was like, let's do that. I don't need the money. Let's wait. And I think what a lot of these funds are doing.

• 1:14:05David Rosenthal?

  Was that in the last fund cycle?

• 1:14:06Speaker 01

  That was in the third fund cycle.

• 1:14:07David Rosenthal?

  Yeah, so now.

• 1:14:08Speaker 01

  So I will contact them. What I decided to do was, let's see what my syndicate members and the public want to do. Let's see which QPs come out of the woodwork.

• 1:14:17Ben Gilbert?

  Yep.

• 1:14:17Speaker 01

  And literally, I did the second call this week, the first one last week. I'm doing the third one next week and it's been so productive. I added two more, so I'm gonna do five webinars this fall and then I'm gonna go on the road and start meeting with folks.

• 1:14:28Ben Gilbert?

  Are there any downsides to doing the, the raising in public thing other than?

• 1:14:34Speaker 01

  Not that I can see. I mean, I guess you could fail in public to fail to raise the fund.

• 1:14:39David Rosenthal?

  That doesn't seem like something you're scared of.

• 1:14:41Speaker 01

  No. I could also, you know, the, the freeing thing, you know, is I looked at the model and I said, you know what I could do? I could just invest my own money in each company. And then syndicate them and never have another LP.

• 1:14:59Ben Gilbert?

  Right, but then you're raising capital every single time you're making an investment.

• 1:15:02Speaker 01

  Yeah, and I'm getting deal by deal carry and I have a hundred percent of my investment, not 25% carry on it. And I don't ever have to talk to anybody. I could just say, I'm placing this bet. Would anybody like to join me?

• 1:15:15Ben Gilbert?

  Yep.

• 1:15:16Speaker 01

  And I don't have to have a fund. I don't have to do audits. I don't have to do any work.

• 1:15:21David Rosenthal?

  Literally, this, you know, it's so funny hearing you say this. Myself, lots of our other friends in the ecosystem that are in similar positions, they're having this same question. Like, on the one hand, I could do what you just said and do very little work, but, but have it all be pure. On the other.

• 1:15:37Speaker 01

  Yeah.

• 1:15:38David Rosenthal?

  I could go do what you are actually doing and like raise, have LPs via Academy. Yeah, how did you weigh these two?

• 1:15:44Speaker 01

  Um, I, I'm going into my second era, my second decade of investing. And I, again, last two years, a lot of like sort of post pandemic and Tony's death thinking, huh, like what's possible here? Because I've won so much in my life. And I mean to be obnoxious about this. I know it probably sounds that way, but for a kid who's, you know, gonna be a cop to be where I am.

• 1:16:13Speaker 01

  And this is why, like when the guys break my chops on the pod, I'm like, guys, I don't aspire. To be a billionaire, it's not important to me. If it was, I would do a late-stage fund. I aspire to be happy and do what I love doing every day, which is the podcast. Maybe get in 40 days of skiing, hang out with my kids, take them on the mountain, and then meet with like, you know, early founders and be able to say, I helped that company at the earliest stages. That, to me, is the rush. I found them first, I backed them first, I sat there with them and figured it out with them.

• 1:16:48David Rosenthal?

  We were talking about the legendary twist, episode 180, with you and Travis.

• 1:16:53Speaker 01

  Yes.

• 1:16:54David Rosenthal?

  Like, man.

• 1:16:55Ben Gilbert?

  That's the secret before the show stuff, David.

• 1:16:57David Rosenthal?

  Yeah, that is. But, but.

• 1:16:58Speaker 01

  I can talk about Travis, yeah.

• 1:17:01David Rosenthal?

  Yeah, but that was like, you know, Urbo was such a baby company back then and like.

• 1:17:05Speaker 01

  Crazy. One city. I invested and I had an open angel forum where Cyan Banisher and Chris Faralek from First Run, you know, invested in the company. I think they both met them there. Saka was there too, but he already, he had a relationship with Travis, so I can't take any credit for that. And Kevin Systrom was watching, and I was gonna kick him out because he was at this coworking space called Dog Patch Labs.

• 1:17:27Ben Gilbert?

  I worked there too. I worked at CoTwee.

• 1:17:30Speaker 01

  Yeah, so he was, oh, CoTwee, I know that. So he's sitting over there building Bourbon.

• 1:17:33Ben Gilbert?

  Yep.

• 1:17:34Speaker 01

  And Sok is like, can Bourbon come in? I'm like, fuck no, this is like private shit. And he's like, but, and I'm like, just tell him to sit at his desk and I won't kick him out.

• 1:17:42Ben Gilbert?

  Wait, this open angel forum was at Dog Patch Labs?

• 1:17:45Speaker 01

  Here, on the pier.

• 1:17:46Ben Gilbert?

  No way.

• 1:17:46Speaker 01

  You think that pier, then they shut down because it was gonna collapse?

• 1:17:49Ben Gilbert?

  Condemned, yeah.

• 1:17:50Speaker 01

  Yeah, condemned. So that was there and.

• 1:17:52Ben Gilbert?

  Naval also did a bunch of like, events there for Angel Hacks.

• 1:17:55Speaker 01

  At the time, Naval and I were very friendly.

• 1:17:59Speaker 01

  Not, not friendly now, but not, we don't hang out, or we, but we used to hang. Kind of bummed about that, if I'm being honest. I really respect him and he was doing something called Venture Hacks at the time. So he would just send an email with, here are the five companies. And I was doing it in person. And he's like, I'm gonna do this thing, Angel List. I'm like, well, I'm just in-person thing. And he's like, great, let's just, you know, trade notes or whatever. And then he sent me the syndicate thing. He's like, do you know about SPVs? I was like, I don't, explain it to me. And he taught me what SPVs were. He introduced me to a sure fund management, which I wound up investing in.

• 1:18:32Ben Gilbert?

  Did you buy that?

• 1:18:33Speaker 01

  I didn't buy it. I mean, I bought 5% of the company, I invested in it, but they back everybody and they've done more SPVs, like, look, like, I don't know if they're up to $10,000 or $5,000. I mean, they've done a ton of it. Seriously great group over there. And so he taught me how to do syndicates. And the first one I did was Calm at four or five million dollars.

• 1:18:52Ben Gilbert?

  That's nuts. It's funny. I was, I was looking for your-

• 1:18:54Speaker 01

  Like literally like winning a championship. The first time you step on the court.

• 1:18:57Ben Gilbert?

  I was looking at your track record, getting ready for this. And I was telling David, like, I think the word that I used, because like, obviously Uber is some ridiculous multiple on a return. But then there's these other ones that are like promising, but early. And then there's other ones where it's been a less than Uber multiple, still good Uber multiple. But you look at Calm, you just, I looked at David, I was like, he sharpshootered that one.

• 1:19:16Speaker 01

  That one I could be even more proud of because, I'll tell you why.

• 1:19:20Ben Gilbert?

  It was like ridiculously early and like a super low basis.

• 1:19:23Speaker 01

  They had, it was $4 million. We put 378K in on 6%. And they didn't raise any money until it was a 250 million dollar valuation. So no dilution.

• 1:19:31Ben Gilbert?

  Wow.

• 1:19:32Speaker 01

  And-

• 1:19:33Ben Gilbert?

  Sharpshooter.

• 1:19:34Speaker 01

  Sharpshooter. And it's really like, I might even- Vanta was the same story. I couldn't even cry, like, telling the story. But Alex, too, and I became very good friends. And Michael Acton, you know, afterwards, because he wasn't actively running Calm while Alex was. Alex, at some conference, I was interviewing him and doing a little victory lap for him, giving him his flowers. And he said, I just want to stop and tell you, you don't actually know this story, but we were going to shut the company down. And we had, Mike and I had a conversation.

• 1:20:03Ben Gilbert?

  What?

• 1:20:04Speaker 01

  Do we take your money? But we're not sure about this. But you believed in us so much, and you insisted on us taking the money. But we had just pitched 40 investors, and they all said no. And we were trying to debate if we could in good conscience, burn your money to do this. And we probably, Calm would not be here.

• 1:20:24Ben Gilbert?

  And they found product market fit while burning through your money?

• 1:20:27Speaker 01

  Yes, I think so. I think so. Because- You're like, take more of my money. No, no. But if you think about that as like, a, that is not the case with Uber or Robinhood. I was along for the ride. Let's be honest. I did not change the trajectory of the company.

• 1:20:40Ben Gilbert?

  But like, but for Jason Calacanis, Calm would not-

• 1:20:42Speaker 01

  That's what they said. Well, he said, it's, they were going to shut it down possibly. I don't believe that they would, but I do think it was on the table.

• 1:20:49Ben Gilbert?

  That's like real angel investing. Like, there's, there's, there's a lot of like individuals participating in venture rounds. And like-

• 1:20:56Speaker 01

  Yeah.

• 1:20:57Ben Gilbert?

  No offense.

• 1:20:58Speaker 01

  Oh, hey. I don't take any offense.

• 1:21:00Ben Gilbert?

  So like all that angel investing, but like coming in when the company could die needs a hundred K, 200 K, 300 K to get it to the stage where they-

• 1:21:09Speaker 01

  Revenue to date, I think, when I invested.

• 1:21:10Ben Gilbert?

  Like ever?

• 1:21:11Speaker 01

  Yeah, because they were selling the app for $10. Because remember at the early stages, there was no subscription model. Right, in the App Store. You just sold an app for $10. The person had it for life. So the business model of apps was make a lighter for a dollar, then make lighter two.

• 1:21:26Ben Gilbert?

  Yeah.

• 1:21:26Speaker 01

  And charge $3 and then lighter four would come out. And you'd be like, well, this doesn't make any sense. It's like making Microsoft Word 1.0. You buy it, throw it away. It's like, but we could just update it. And it's like, yeah, but we need to make more money. So shut the old one down. So you'd buy Angry Birds and you buy Angry Birds 2, Angry Birds 3. You know, it was a really weird time. And then they're like, yeah, we're doing something. They told me like, you know, um, cause you know, I was under NDA as well. You know, hey, subscriptions are coming. That's going to change everything. And they were going to do $10 a year. And I said to Alex and Michael, how much does it cost to go to a meditation class? It's donation based and there's only like 10 places you can go. I'm like, well, what's the suggested donation? It's like $20 in LA. I said, you want to charge $10 a year. It's $20 a month. How often do you have to do this to-

• 1:22:11Speaker 01

  $20 a visit. Yeah, $20 a visit. I said, how often do you have to do this to get value? Which should be a daily practice. We're like, how often do you have to go and learn? I said, if you go weekly, that's good. I was like, so it's $80 a month to go and we're charging $10 a year. So that's like a thousand dollars a year versus $10. What if it was $10 a month? They're like, we've been thinking about that. I was like, okay. And they're like, okay, yeah, I think we're going to do that. And it was, then they went to $10 a month or whatever. And they didn't wind up at $60 a year, whatever it was. But we got money printing machine pretty quickly.

• 1:22:42Ben Gilbert?

  So I've never made an investment at like pre-product market fit. That's like now worth over, you know, a billion dollars. Like that's a, that's a, that's a very early to very successful. And I'm curious, like, did it feel any different when you were making that investment? Were you like, there's something more special here-

• 1:22:59Speaker 01

  Of course.

• 1:22:59Ben Gilbert?

  Than my normal investment.

• 1:23:01Speaker 01

  Absolutely.

• 1:23:02Ben Gilbert?

  Really?

• 1:23:02Speaker 01

  Absolutely. And that's what I've basically turned into a playbook at launch and that I'm teaching these 12 people how to do is how to do that.

• 1:23:10Ben Gilbert?

  What do you think it was? Like what was, when you look back and you're like-

• 1:23:13Speaker 01

  Nine factors. Nine factors. Okay, all right. Well, Angel, Angel dot University.

• 1:23:19Ben Gilbert?

  Angel dot University.

• 1:23:19Speaker 01

  No, I'm not even teaching at Angel dot University, but I, I'm training my team when they're meeting with those sixty companies. And every time they pitch me one, they say this has three of the nine, this has four of the nine. And then I'm creating the anti-list, these are the things that kill companies. So how many of the fifteen things, we have a long list of things that kill companies. How many of the red flags does it have, reasons to not invest, how many reasons to invest does it have? And you know, like, one of them for me, and everybody's got their different ones, I won't give all of them, but one of them is world-class design. And so I'm trying to teach people what world-class design is. And world-class design to me is if you were to look at all the companies in the space, this one would have the best design. Or this would be one of the top ten percent. So if you were to look at something like Calm or Robinhood, okay, they're the best-looking app with the best UX of all of, of anybody in the category.

• 1:24:04Ben Gilbert?

  Right.

• 1:24:04Speaker 01

  So Calm was better than Headspace, Robinhood was better than E-Trade, I mean, it's just, it doesn't take a rocket scientist to look at them. But when I first explained this to my team, they would bring me companies and they'd say world-class design. And I was like, I'm like, they're like, I really like the design, I'm like, pull it up. And they pull it up and I'm like, that's a template from, you know, like a website builder and it's a stock photo, but where's the actual design of the product? And they're like, oh, that's on this product page, on the product page. And I was like, okay, yeah, again, that's just like the, I mean, if this was a bank's website, maybe, but that's not world-class. That's serviceable design, that's utilitarian design, that's okay design, that's good design, it's not world-class.

• 1:24:46Speaker 01

  So let's, if we're gonna say world-class, like a world-class performance is different than a serviceable performance. World-class cinematography, world-class script, world-class dialogue, that's different. And that's, and then product philosophy is the other one I like, so. Okay, we met with this company in June, it's now July, what's changed about the product? And they're like, we don't know, I'm like, okay, well, let's find out. Where's their changelog, where's their roadmap? So in the earliest stages, you might have revenue traction or user traction, but you might be able to ask them for their product roadmap and. Somebody like Travis would be like, yeah, here, get on the phone with this guy and we'll walk you through it. Here's what we're debating about on Sunday. We prioritize.

• 1:25:23David Rosenthal?

  And then a month later, they're like.

• 1:25:24Speaker 01

  And then they're like, check, check, check, check. And then you go like if we're with Raul with Superhuman, and I was investing in his company before that report of Raul, like the change log at Superhuman.

• 1:25:32Ben Gilbert?

  Dude, Superhuman, that people don't realize, like.

• 1:25:35Speaker 01

  They're like, bink, bink, new feature, bink, new feature. Oh, boom, we fixed Grammarly. Oh, bink, we have calendar, boop. Oh, we got a new calendar feature, boop, we got this feature. And you're like, hmm.

• 1:25:44Ben Gilbert?

  So here's an interesting question. We should ask Raul this. We've had him on the show three times now.

• 1:25:47Speaker 01

  Product genius.

• 1:25:48Ben Gilbert?

  Like, the, the parallels between Superhuman and Figma are uncanny, like design-led founder, like revolutionary design in the software, rewriting the entire browser stack in order to get the performance. And I remember it being breakthrough when it came out. And then the only thing that I can recall being different between then and now is adding a calendar thing that I don't use and a mobile app and iPad support. And, and why?

• 1:26:15Speaker 01

  Outlook support, you just don't, you know, when you hit Command K.

• 1:26:18Ben Gilbert?

  Yeah.

• 1:26:19Speaker 01

  You probably know 50% of the features.

• 1:26:21Ben Gilbert?

  Right.

• 1:26:22Speaker 01

  Like, do you use Remind Me Of This?

• 1:26:23Ben Gilbert?

  I do.

• 1:26:24Speaker 01

  Okay, great. Do you use Labels? Do you do Snippets?

• 1:26:27Ben Gilbert?

  I do.

• 1:26:27Speaker 01

  Okay. Yeah.

• 1:26:29Ben Gilbert?

  Which was all there when I started using it, three, four years ago.

• 1:26:32Speaker 01

  I think a lot of those things have gotten better and better.

• 1:26:36Ben Gilbert?

  Yeah. So it's just that, like, polish, polish, polish, polish.

• 1:26:39Speaker 01

  Um, I really like want them to make snippets multiplayer. I want to share my snippets.

• 1:26:44Ben Gilbert?

  Oh, yeah.

• 1:26:45David Rosenthal?

  Oh, with your team.

• 1:26:46Speaker 01

  I love.

• 1:26:46Ben Gilbert?

  Yeah. So like. I want all of David's past emails. They're so nice.

• 1:26:50David Rosenthal?

  I don't do email anymore.

• 1:26:52Speaker 01

  You do it on the phone?

• 1:26:53David Rosenthal?

  No, no, I just don't do email. I don't email anybody.

• 1:26:56Speaker 01

  You know, we pass on a company.

• 1:26:57Ben Gilbert?

  I actually do have all the past emails from.

• 1:26:59Speaker 01

  I've been, I've been literally creating a collection of how to pass with my team and I'm standardizing that.

• 1:27:04David Rosenthal?

  I'm trying to. I don't know that I'll be successful. And this may be a mistake, but I'm trying to just not have, I don't end up having a conversation with a company if I'm not going to invest.

• 1:27:16Speaker 01

  No, but you must say, hey, we are not going to invest. You've took a pitch.

• 1:27:20David Rosenthal?

  Oh, no, I get it. I don't, I don't.

• 1:27:23Ben Gilbert?

  You basically don't take a pitch unless you're going to invest. It's the weirdest thing.

• 1:27:27Speaker 01

  Oh, that's very weird. So you do all your work upfront? You front load it, the DAF, everything?

• 1:27:32David Rosenthal?

  We're in this unique position, as you are too, but with acquired, where like, you know, we have every six months, we have six companies that we work with on the show as our sponsors and our partners, and we get to know them really well.

• 1:27:45Ben Gilbert?

  It's modern treasury and it's.

• 1:27:47David Rosenthal?

  And I'm now an investor in just about all of those companies. So it's not like they're pitching me.

• 1:27:52Ben Gilbert?

  It's growth stage investing.

• 1:27:53David Rosenthal?

  Yes.

• 1:27:56Ben Gilbert?

  They're not yet priced as if they're the winner most of the time, but they're gonna just keep compounding.

• 1:28:01Speaker 01

  Yeah, good luck. Yeah, pricing's gonna be hard. Well, it's depending on entry price.

• 1:28:06David Rosenthal?

  We'll see.

• 1:28:06Speaker 01

  Yeah, I don't know what's gonna happen to these companies after, you know, like, flat is the new up, but I think, you know, 50% haircut is the new flat.

• 1:28:15David Rosenthal?

  Well, public comps got hit 50 plus percent.

• 1:28:18Ben Gilbert?

  Yeah, I mean, this week they got hit harder again.

• 1:28:20Speaker 01

  Yeah, I mean, I'm buying equities right now. I've been doing it at jtrading.com and I am gonna buy more.

• 1:28:26Ben Gilbert?

  Sorry about all my picks a couple of weeks ago.

• 1:28:28Speaker 01

  Which one?

• 1:28:29Ben Gilbert?

  Whatever I thought you said.

• 1:28:30Speaker 01

  Oh, yeah, yeah. No, no, I actually love Taiwan Semiconductor.

• 1:28:34David Rosenthal?

  Stitch Fix was the other one.

• 1:28:37Speaker 01

  Twilio was yours and I love that one too. And I like Shopify as a pick. I'm actually really enjoying it. It's really balancing out. Not investment advice, but it's balancing out my

• 1:28:49Speaker 01

  understanding of what public success is compared to private. And so for me, it's just a way, like, am I going to fight with the blaster? No, I'm a Jedi. I use a lightsaber. But, you know, I'll learn if you use a blaster. It's not as elegant.

• 1:29:04Ben Gilbert?

  It's helpful. It's really helpful.

• 1:29:06David Rosenthal?

  If you look at the very best people, the best GPs in venture over the past two decades, they all trade public stocks.

• 1:29:13Ben Gilbert?

  Yes.

• 1:29:14David Rosenthal?

  And they do it for this same reason. They're gonna fight with the saber, but like, they wanna know.

• 1:29:19Speaker 01

  How to use a blaster. Yeah, or how to fight an X-wing or something. Like, it's not what a Jedi does, but Jedi will do it.

• 1:29:26Ben Gilbert?

  It also keeps you really sensitive to the public cycles so that like, it's not that you have to.

• 1:29:34Ben Gilbert?

  Think about the public comps when you're investing, but you have to be aware of how much those will change.

• 1:29:39Speaker 01

  Yeah.

• 1:29:40Ben Gilbert?

  And early-stage investing, it's almost silly to compare to, like, my opinion is it's very silly to compare to public comps because the only thing you know for sure is we're going to be at a different place in the cycle by the time this company gets liquid. So it's ridiculous, but it's helpful to drive into you like how much variability there is. When was the last time it was this different?

• 1:29:58Speaker 01

  Yeah, I'm really enjoying understanding what the founders of those companies go through versus the founders of the private companies that go through, what the boards, the decisions the board has to make of a public company versus the board of a private company.

• 1:30:10Ben Gilbert?

  Yeah.

• 1:30:10Speaker 01

  So it, you know, I'd like to join a public board at some point, probably not a good idea for me to have said that because I might get an invite for one and that might be too much work, but yeah, especially given the market right now. I'm very careful.

• 1:30:24Ben Gilbert?

  But you could, you could also be.

• 1:30:25Speaker 01

  To do that, but it's just, it's been great.

• 1:30:27David Rosenthal?

  Especially through the show now, you have relationships with public company founders.

• 1:30:30Speaker 01

  Sure, of course. Yeah, I mean, if I really wanted to, I'm sure I could lobby.

• 1:30:33David Rosenthal?

  Oh, you don't have to be on the board, though. You can have a very relationship with.

• 1:30:37Speaker 01

  Doing the analysis and I'm doing it anyway with Molly every day. Okay, you know, Twilio's or Adobe's come out. I just bought Adobe this week when they bought Figma.

• 1:30:43Ben Gilbert?

  So funny, so did I. Not investment advice.

• 1:30:45Speaker 01

  Not investment advice, but I was like.

• 1:30:47Ben Gilbert?

  They bought Figma, tanked. Okay, so here's my theory on this. They bought Figma and tanked and I was like, why did, why do people hate this? And they're like, oh no, Adobe's admitting defeat and that like they can't invade a house or, and to me, I, I look at it like Adobe has customer channel and it was foretold five plus years ago that they were not going to build the next Figma. Like that would be a full rewrite of their entire software stack.

• 1:31:14Speaker 01

  Yep.

• 1:31:14Ben Gilbert?

  So buying the thing, even though they paid a tremendous premium because 50x revenue multiple because of the network effects that Figma has, and obviously all the product stuff, but if they can get that through Adobe's channel. Like, I think that is an absolute win-win acquisition. And all these people that are like, "Oh, they're gonna ruin it. They're gonna kill Figma." No, they're not. That's why they paid $20 billion for it and have a gigantic bonus for Dylan to stay on board.

• 1:31:40Speaker 01

  Yes. They're taking a YouTube approach. I think everybody in M&A knows now.

• 1:31:45Ben Gilbert?

  Yeah.

• 1:31:45Speaker 01

  Like, let it be.

• 1:31:46Ben Gilbert?

  Or WhatsApp.

• 1:31:47Speaker 01

  WhatsApp. Just leave it alone. Don't screw it up. And then, so I like your analysis. I added to that analysis is, if you're not going to win the war, and you can build an alliance and then fight another war? Like, they've just removed the downside

• 1:32:06Ben Gilbert?

  Yep.

• 1:32:06Speaker 01

  of Figma creating Photoshop.

• 1:32:08Ben Gilbert?

  I'd be concerned for Adobe if they didn't buy Figma.

• 1:32:12Speaker 01

  Correct. So, the fact that you're giving us a discount on the shares for them doing the right thing is like Christmas. Like, thank you.

• 1:32:20Ben Gilbert?

  Yeah.

• 1:32:20Speaker 01

  You just discounted the right move? Fantastic. It would be like, people are like, "Oh, you know, the Warriors signed Kevin Durant."

• 1:32:29Speaker 01

  And you know what? We're gonna lower the... Their Vegas odds are going down. We're lowering the cost.

• 1:32:32Ben Gilbert?

  But they paid a lot to get him on the team, so...

• 1:32:34Speaker 01

  Yeah. And, oh, you know what? We're gonna lower the cost of the tickets.

• 1:32:38Speaker 01

  Okay, I'll buy courtside seats, or, you know, or they're lowering the odds in Vegas. It's like, wait, why are you lowering the odds? Their odds increased. I'll place that bet. So it's just an obvious bet. And then there's all that's left is Canva, and Melanie's awesome.

• 1:32:51Ben Gilbert?

  Totally different thing.

• 1:32:52Speaker 01

  But, yeah, and they have a free Canva already, and, you know, what if? There's always the internal people who are penciling out that spreadsheet.

• 1:33:02Ben Gilbert?

  Yep.

• 1:33:03Speaker 01

  There's a group of MBAs who penciled out that spreadsheet with Figma, no offense to MBAs who are listening. And they said, "Hey, boss, if X, Y, if X, Y, Z..." And they said, you know, "Here's like five potential paths. If we make Figma free..." For 10 users and whatever, or if we, you know, take whatever Figma costs and then we blend it with the Adobe suite, okay, we would get this many more Figma users, but we know when we get Figma users, then we get non-designers to pay for it. So right now Adobe has a bunch of designers paying for it.

• 1:33:39David Rosenthal?

  Right, right.

• 1:33:40Speaker 01

  But they may not have all the non-designers in there.

• 1:33:42David Rosenthal?

  Right, only designers pay Adobe.

• 1:33:43Speaker 01

  Right.

• 1:33:44Ben Gilbert?

  Well, no, they have Marketing Cloud, but that's a totally different set of...

• 1:33:48David Rosenthal?

  Yeah, only...

• 1:33:49Speaker 01

  But when you look at Figma, like, I got a Figma account, like, people who are doing, giving feedback on designs, the business side, the sales side can get into Figma.

• 1:33:59David Rosenthal?

  Plus, they got the whole creator class.

• 1:34:01Speaker 01

  Exactly. So I think you're opening up the aperture of who design software is for with Figma. It's for BD. It's for the CEO. Sure, the CFO can come in and take a look at the product. Oh, legal should come in and take a look at the product. Yeah, buy them a seat. So it's like Slack is for the dev team. And it's like, yeah, and the sales team, and ops, and anybody else might as well be on there, because that's where everybody is. So that's what I think is gonna happen with Figma. It's like, everybody's gonna have a Figma account in the future, just to watch the product team build the product and put a comment in. And who cares if it's 100 bucks a year? It's cost of doing business.

• 1:34:32Ben Gilbert?

  Any company that has like that kind of strong network effects inside an organization deserves a meaningful revenue multiple, because they just, their differentiator is literally the company's moat. So like, I tweeted this, but like, if I have a castle and it has a moat around it that is much wider or deeper than your identical castle, shouldn't you pay more for my castle that's more defendable?

• 1:34:56Speaker 01

  100%. Like, the virality of it. I think Sacks made this point on All In two weeks ago, which was like, if they're paying 50x now and the company's growing, okay, they're paying 20x next year, 25x, who cares? This thing's such a high-growth company. And then I was just thinking, well, somebody's got a theory there. And when I sold Weblogs to AOL, people were like, oh, my God, these people are idiots. They gave $30 million to, you know, for Weblogs, Inc. They won 200K in revenue. What they didn't realize was AOL Autos, AOL Tech, AOL Lifestyle, those were sold out at like a $90 RPM, revenue per 1,000 pages. The ads, different CPMs. So then they would put an Engadget or an Autoblog Story, or Blogging Baby, or whatever other blog we had, on the homepage of AOL.

• 1:35:41Speaker 01

  And a half million people would flow through. And then they would put those ads on our sites.

• 1:35:46Speaker 01

  And then they would blow out fifty or a hundred thousand dollars in ads a day on a blog. And those people were like, great, because it was costing AOL to make content like five hundred dollars per piece of content, three thousand dollars per piece of content on AOL.com slash autos, whatever. And we were doing it for, at the time, five bucks a blog, five dollars a blog post. Because we said, well, people can write for an hour, so it's twenty bucks an hour, and it's six dollar minimum wage.

• 1:36:11David Rosenthal?

  Yeah, god, the internet media game has changed so much.

• 1:36:14Speaker 01

  And then I was like, okay.

• 1:36:15David Rosenthal?

  You guys were doing two hundred K annual revenue.

• 1:36:17Speaker 01

  We had done two hundred K to date.

• 1:36:19David Rosenthal?

  Holy.

• 1:36:20Speaker 01

  Over the eighteen months.

• 1:36:21David Rosenthal?

  What is, I mean, now, like, the world we're in today, like.

• 1:36:24Speaker 01

  And they were like, J Cal just robbed AOL. And I was like, okay, no. Thirty million dollars. And then I look like an idiot.

• 1:36:34David Rosenthal?

  What do you think, like, here's a.

• 1:36:35Speaker 01

  I look like an idiot five years later, and that's the best, the best M and A. Yeah. Is when you look like you robbed the bank.

• 1:36:43David Rosenthal?

  Yeah.

• 1:36:43Speaker 01

  And then five years later, it looks like you robbed the founder.

• 1:36:46David Rosenthal?

  YouTube.

• 1:36:47Speaker 01

  Instagram. Figma will be in this category, like, yeah, when they bought Instagram, they're like, thirty people work at this company, and they gave them a billion dollars. You guys are morons, and now it's a hundred, fifty billion dollar company.

• 1:36:56David Rosenthal?

  Here's a thought exercise question, obviously irrelevant, because you don't monetize it.

• 1:36:59Speaker 01

  Yeah.

• 1:37:01David Rosenthal?

  What do you think the enterprise value of All in is?

• 1:37:04Speaker 01

  Well, it would do ten million dollars in, I, I, I, when I was at the code conference, you know, a lot of people have been trying to buy it, or, you know, put it as part of their network, obviously. Which would kill it. Yeah, you know, my partners are right, like, let's not make money from it. Part of, part of the delightfulness of it is that we're not trying to monetize it.

• 1:37:21David Rosenthal?

  Well, but, but you do get huge economic value out of it, even without monetizing.

• 1:37:25Speaker 01

  Chamak pulled me aside at some point, and was like, hey, schmuck, like, just, we're friends, like, you're all, your next fund will be bigger than that.

• 1:37:31David Rosenthal?

  Hey dumbass.

• 1:37:32Speaker 01

  And I was like, you know, when you have a friend who can be like, hey dumbass.

• 1:37:34David Rosenthal?

  Yeah.

• 1:37:35Speaker 01

  Like, that's a good friend, so I appreciate Chamak saying that, and he's right, and it's playing out. And we had a rule, no, no talking our books on the pod, but we kind of talked about it, and we're like, the pod is great when we talk about our bets, so explaining our bets, not talking our book is the new philosophy, so like,

• 1:37:52David Rosenthal?

  You guys just started doing that.

• 1:37:53Speaker 01

  About his SPAC, you know, I embrace call. Yeah, he did, he just found a target for it.

• 1:38:00David Rosenthal?

  Yeah, Chamak talked about the healthcare company.

• 1:38:03Speaker 01

  The healthcare company, which is, I mean, we wanted to talk about that, because Chamak and I both agree, like, maybe we're, I mean, maybe. Like, we're definitely over prescribing these drugs to kids, like for ADHD and attention drugs, and adults are taking too many. I think that that's not disputable. I think all the science is showing that. So, you know, to make software that could help kids with ADHD is like noble. But I think people want to hear us explain our bets. So, you know, explaining our bets, I think, is kind of a cool aspect of the show. Talking your book is lame, but explaining your bets is cool. So, anyway, in the event, did a couple million dollars, had a small profit. But it was the number one tech event of the year by far.

• 1:38:44David Rosenthal?

  Right.

• 1:38:44Speaker 01

  So, you know, I'm kind of bummed that, you know, Freeberg's a little bit of a blocker for it, but I might turn him around and we'll have a vote, maybe in the fall.

• 1:38:53David Rosenthal?

  Doing another one, oh.

• 1:38:54Speaker 01

  Well, I'm going to do another one. The question is, am I doing it under the All-In brand, or do I have to create a new brand for it? And so I told the guys, I said, I'm going to do it again.

• 1:39:03David Rosenthal?

  Well, Code Conference is done, so like, there's a vacuum.

• 1:39:04Speaker 01

  Code Conference is done, yeah. They need a new host.

• 1:39:08Speaker 01

  That's crazy that that can be done. Like, it's such a valuable... No, I talked to Bankoff about it, and he's been very public. You know, Kara Swisher, I think, is going to do the Pivot stuff and wants to do other stuff. And, you know, she's, I really respect what Kara has done, you know, in terms of like, she does stuff and then she moves on to the next thing and tries. Like, you know, it's kind of my approach as well, which is like, Bob Dylan, you know, said like, "Don't look back" kind of thing. And he always tried to make the next album and forget about the past one. And much to the chagrin of people who loved him as a folk artist and didn't like, you know, like a Rolling Stone. And when he went electric, they booed him. You know, I was like, really? You're booing Bob Dylan because he's using an electric guitar? Are you guys dumb? Like, did you hear "All Along the Watchtower"? Like, this is incredible. And so I think, you know, Kara Swisher, like, is moving on. But Jim said he's going to keep doing it.

• 1:39:52Speaker 01

  And, you know, it's probably a small list of people who could actually host that credibly, you know, a very small list. And so...

• 1:39:59David Rosenthal?

  Which you're definitely on.

• 1:40:00Speaker 01

  I am? You think?

• 1:40:03Speaker 01

  How could you not be on it?

• 1:40:04David Rosenthal?

  I mean, I'm not even saying that to make you feel like...

• 1:40:06Speaker 01

  No.

• 1:40:06David Rosenthal?

  Okay, okay. You're joking about being humble.

• 1:40:10Ben Gilbert?

  But if it had...

• 1:40:11Speaker 01

  I'm proud to joke about being humble.

• 1:40:12Ben Gilbert?

  If it had that kind of prestige, it seems like Friedberg would want to do it. It seemed more like the thing he was averse to is the like...

• 1:40:17Speaker 01

  Yeah, I mean, whatever the issue is, like, we've had our issues. We all have issues. But I think there's basically two possibilities for All In Summit. I'm going to present it to the boys and say, like, here's the plan. Yes or no? And we agree, we'll put it to a vote. So we put it to a vote. If three of us want to do it, we'll do it. And if two of us want to do it, then we can't. And if I already, Friedberg already said, if you do it on your own with a different name, I'll come and support you and I'll show up to do a talk or do an interview or whatever. And I was like, great. So I'll do it with a different name if they don't want to do it. And the fans can decide if they want to come or not.

• 1:40:57Ben Gilbert?

  Partially in.

• 1:40:58Speaker 01

  Partially in, exactly. So, you know, it's up to the boys. They want to do it, but it was like a pretty great success.

• 1:41:04David Rosenthal?

  You already have call-ins.

• 1:41:06Speaker 01

  Yeah, well, yeah, and I started doing, I started doing a call-in show called After All In for the last two episodes where I took calls about the last episode of All In, just to support David because I don't think people remember how great that app is. It really made great progress, so I want to be supportive of him. And I have a small investment in it.

• 1:41:23David Rosenthal?

  Do you...

• 1:41:24Speaker 01

  Very meaningful, but...

• 1:41:25David Rosenthal?

  On the one hand, this is ridiculously, on the other hand, it might be ridiculously low.

• 1:41:29Speaker 01

  It's worth 50 million, to answer your question. 50 to 100 million. I mean, as a top, as a top 40 podcast, it's worth at least 50 million.

• 1:41:36David Rosenthal?

  On its own, though, but I mean, like, economic value that the four of you...

• 1:41:39Speaker 01

  Oh, who knows? I mean, if Chamath...

• 1:41:42David Rosenthal?

  Like...

• 1:41:43Speaker 01

  If Chamath or Sax or I or Friedberg were to get but one more deal out of it, and it's an Uber, the economic value is nine figures.

• 1:41:52David Rosenthal?

  Right.

• 1:41:53Speaker 01

  Possibly 10, you know, like, so, yes, of course.

• 1:41:54David Rosenthal?

  But that's the thing, like, I think, like, man, Weblogs, like, you were doing 200K of revenue, you sold it for 30 million.

• 1:41:59Speaker 01

  Pretty great takeaway, yeah.

• 1:42:01David Rosenthal?

  And now, look at this, like, you know?

• 1:42:03Speaker 01

  Yeah, I mean, listen, I hope it keeps going. I hope we can keep it on track and, you know, I love doing pods. This Week in Startups is a juggernaut as well, you know?

• 1:42:11David Rosenthal?

  Yeah, that would...

• 1:42:12Speaker 01

  It's been sold out for 10 years and All In is...

• 1:42:14Ben Gilbert?

  What is that, like, a quarter million listeners or something?

• 1:42:16Speaker 01

  Yeah, something in that range, yeah. I mean, it's hundreds of thousands per episode and, yeah, it's very niche podcast, you know? I'm not trying to make it all in. I'm trying to make it for founders. And so, you know, if in order to make it bigger, it'd have to be worse for founders.

• 1:42:32David Rosenthal?

  Right.

• 1:42:32Speaker 01

  And That's what we talk about. I want founders.

• 1:42:34David Rosenthal?

  It's like what we think about with our show.

• 1:42:35Speaker 01

  Well, I want founders and capital allocators to listen to it. And I'm not trying to move up the rankings. I don't mind, you know, hanging with, you know, all in being number one in tech and then hanging out with you guys at, you know, slumming it at six to 15.

• 1:42:48David Rosenthal?

  Right.

• 1:42:48Speaker 01

  With you guys in the rankings. It's like, that's where we belong.

• 1:42:51David Rosenthal?

  Look, I got number one unlocked.

• 1:42:52Speaker 01

  Four to six, but who's counting? Whatever, you know, that's where we belong with these things, right? Like, it's like, it's a niche podcast by definition, right? Like, it's not supposed to appeal to everybody. And you try, if you want to appeal to everybody, like, read the Bible, like, that's

• 1:43:04David Rosenthal?

  Right.

• 1:43:04Speaker 01

  If you go to the This is the beauty of the internet. Literally, this guy who reads Bible passages and he That's huge. It's like, if you can literally

• 1:43:11David Rosenthal?

  True crime.

• 1:43:11Speaker 01

  True crime.

• 1:43:12David Rosenthal?

  Religion.

• 1:43:13Speaker 01

  Read the Bible, or Ben Shapiro dunking on libs. The end.

• 1:43:19Speaker 01

  That's like, that's how you get this.

• 1:43:20David Rosenthal?

  Rogan, Rogan.

• 1:43:21Speaker 01

  Or do it daily. But Joe Rogan's out, right? He's on Spotify.

• 1:43:23David Rosenthal?

  Right, right.

• 1:43:24Speaker 01

  You know, he's not in the other rankings. So, I mean, or do a daily news program for 20 minutes. Like, but that's not what I want to do. I want to talk for an hour or three about deep topics in founders and capital allocators.

• 1:43:35David Rosenthal?

  You know what would be a fun, acquired episode is Howard Stern. I feel like it's underappreciated how much Howard Stern

• 1:43:39Speaker 01

  I copied my, that's the playbook. That should be the next Taylor Swift

• 1:43:43David Rosenthal?

  Yeah.

• 1:43:43Speaker 01

  type episode that we do. Yeah, no, for sure.

• 1:43:45David Rosenthal?

  He wrote the playbook.

• 1:43:46Speaker 01

  I literally took notes for it. King of all media. Do you know him? I have never met him. Would love to at some point. I have a lot of respect for him. I mean, obviously, he did crazy stuff when he was young and that shock jock stuff. But he, in his later years, became a great interviewer.

• 1:43:59David Rosenthal?

  Great interviewer.

• 1:44:00Speaker 01

  Great interviewer. He really refined his technique. I really appreciate that about him. And he created characters. Sound familiar?

• 1:44:06David Rosenthal?

  Yep.

• 1:44:07Speaker 01

  He branded them.

• 1:44:08David Rosenthal?

  Yep.

• 1:44:09Speaker 01

  He showcased them, the whack pack, you know, all this stuff.

• 1:44:12David Rosenthal?

  Did he ever do an event?

• 1:44:14Speaker 01

  He used to do live events. He did the US Open Soars, where, and then he would do Howard Stern's, like, New Year's Eve celebration. So, yes, he did the equivalent of those in New York. But it was a very New York thing. So, he, like, he played tennis against Baba Booey. And, but I mean, he got 10,000 people to show up and buy tickets

• 1:44:31David Rosenthal?

  Right.

• 1:44:32Speaker 01

  to a tennis match that they pumped up, you know, Like for whatever number of months. I remember this from my childhood and then he did his books. Uh, which were phenomenal.

• 1:44:40David Rosenthal?

  He did a movie.

• 1:44:41Speaker 01

  He did a movie. He did TV shows. So he's done a lot of stuff and I I'm just starting uh the process of doing a reality show right now.

• 1:44:48David Rosenthal?

  Oh.

• 1:44:49Speaker 01

  Literally gonna do. Are you really? Yeah, I mean.

• 1:44:51David Rosenthal?

  Just you or the besties or?

• 1:44:52Speaker 01

  No, just me. Um, besties don't want to do it. They don't have time for it. I mean, there was, there was talk of like maybe all in. You know, kind of going on to one of those services like people had reached out like, hey, would this work? You know, in.

• 1:45:04David Rosenthal?

  It's a lot more work though.

• 1:45:05Speaker 01

  Well, you know, we would have to show up in a location. We'd have to do it weekly. You know, there'd be some formats, some shiny floor, whatever. It's a, it's a different beast. I don't think they have the time for it, if I'm being honest. Uh, but for me, I would like to do a reality show in the Gordon Ramsay kind of vein, um, you know, where I'm helping founders. I think it'd be great for reach. Uh, so I'm I had done a reality TV show with NBC, uh, and the Weinstein Corporation.

• 1:45:32David Rosenthal?

  Oh, wow.

• 1:45:33Speaker 01

  Uh, yeah, and it didn't make it on air, but I have the. You should be a Shark Tank judge. I had been, they had reached out before. Mark Burnett had reached out early on when it was Dragons Den.

• 1:45:43David Rosenthal?

  Right.

• 1:45:43Speaker 01

  Before when they were going to bring it here. So when it was Dragons Den, they, they had reached out early, but I wasn't very successful back then. Um, I wish, but you know, I think now I think I would have the credibility and the advice to give that I could do a Gordon Ramsay style show. That would be very entertaining and educational and be completely different than you know, the fundraising aspect and the pitch aspect of Shark Tank. So I'm not going to do that, but I'm, you know, I've got you know, the, I won't say which one, but a very major the major, you know, uh, reality TV folks reached out, I think in part.

• 1:46:18David Rosenthal?

  Could you though have, would founders and companies feel comfortable? Like, I feel like a, a really amazing window and insight would be the type of conversations that you have with a founder as they're building the company.

• 1:46:29Speaker 01

  Yeah, so they.

• 1:46:30David Rosenthal?

  Would founders and companies be open to that?

• 1:46:31Speaker 01

  Yeah. So the NBC show I had done the pilot for, uh, which never made it on air. What was really good was really about, you know, me incubating companies and they spent like four or $500,000 doing the pilot. It was really good and it would have been a big hit.

• 1:46:47Ben Gilbert?

  Did it get canceled because of the?

• 1:46:49Speaker 01

  Yeah.

• 1:46:49Ben Gilbert?

  Weinstein stuff. Wow. So they were just like anything that was in his company?

• 1:46:52Speaker 01

  And all the IP is dead because he's a monster. And so anything associated with it, but you gotta remember, he did Project Runway. So he had done some of these giant shows. People don't know that about that. And so.

• 1:47:03David Rosenthal?

  That's right. I forgot. Yeah, that had the TWC at the beginning.

• 1:47:06Speaker 01

  Exactly. So, you know, NBC, you know, NBC bought the show in the room, loved it and did the pilot and came close. And Chamath was on that episode, actually. He did the pilot with.

• 1:47:16Ben Gilbert?

  Oh, my God.

• 1:47:17Speaker 01

  He was like my VC friend who came in and it was hilarious. It's no, it's hilarious. But I'm excited to do it. If it works out, it works out. If it doesn't, you know, no skin off my back. But I like the media space. And then, you know, I, this is the thing, I'm choosing to do media because I get joy out of it. I'm 51 now. I'll be gone soon. Like, I want to enjoy.

• 1:47:41Ben Gilbert?

  I'll be gone soon.

• 1:47:42Speaker 01

  Well, you know, you never know. And, you know, I've had two.

• 1:47:45David Rosenthal?

  Well, you've met some of your friends. Yeah.

• 1:47:46Speaker 01

  I have two friends who died young and I'm just like, I, you know, talked to my wife. I was like, I don't know. Like, what if I make it another year or make it 25 years, but I want to make it count. I'm not going for max dollars. Like, and so when the guys break my chops about that, I'm like, guys, it's not my priority. Like, literally maximizing money is like.

• 1:48:03David Rosenthal?

  Well, also, like, you're probably at a point now where like.

• 1:48:05Speaker 01

  It's not, it's not, literally not in the top 10.

• 1:48:06David Rosenthal?

  What is more money gonna do like?

• 1:48:07Speaker 01

  It seems unlikely.

• 1:48:08David Rosenthal?

  You know, you get a plane, like, you wanna, you wanna play.

• 1:48:11Speaker 01

  You guys understand my life. Like, it is ridiculous and charmed. Like, I can do whatever I want. I have enough money to do whatever. My kids are fine. I can have whatever I want. I don't care about like a third home. Like, I have a ski house. I have my regular house. It's good. I'm, I'm good. My kids have their college paid for. Do you actually feel that way? I'm good. 100%. I literally do not care about more money.

• 1:48:31Ben Gilbert?

  Do you feel like that's a demon that you fight is like?

• 1:48:33Speaker 01

  No.

• 1:48:33Ben Gilbert?

  Any allure toward?

• 1:48:35Speaker 01

  No, I had it when I was younger. I wanted to be powerful. I wanted to be important. I wanted to have money. I wanted to be seen. I wanted people to recognize my greatness. Like, any person recognized me for what I do. I got all that. It literally does not even come up my radar. To have more money is the last thing I'm thinking about. I do want to have, I do want to, you know, be the greatest investor of all time. Yeah. Like, to me, that's meaningful, or be one of the, I want to be, like, I know I'm Mount Rushmore for angels. Yeah. I want to be Mount Rushmore for all investors. So when you guys do your thing in 10, 20 years, it's like, okay, you know, here's Doug Leone and Moritz and, you know, uh, here's, Gurley. John Doerr, here's Gurley. Like, if we are making Mount Rushmore. You want to be on that with them.

• 1:49:18Speaker 01

  I would like to make it there, or at least be in the conversations.

• 1:49:22David Rosenthal?

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

• 1:49:28Ben Gilbert?

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• 1:49:39David 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.

• 1:49:59Ben 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.

• 1:50:12David 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.

• 1:50:23Speaker 01

  When you guys are having the conversation in 20 years and I'm gone, or I'm retired, and you're saying Mount Rushmore.

• 1:50:29David Rosenthal?

  It's hard to imagine you retiring.

• 1:50:30Speaker 01

  Yeah, I think it's possible. Um, I met Don Valentine when they were like, you know, he was not active investor, but when I pitched Mahalo, he was in the room, he came up, I talked to him. He was, oh, he was still hanging out there all the time. Yeah, like, why retire? Um, he was just awesome.

• 1:50:43David Rosenthal?

  Oh.

• 1:50:44Speaker 01

  But, you know, if you had that conversation right now about Mount Rushmore. Like you gotta, okay, so.

• 1:50:50David Rosenthal?

  Who's on your Mount Rushmore?

• 1:50:51Speaker 01

  Well, I mean, you gotta have Don Valentine.

• 1:50:53Ben Gilbert?

  Yeah.

• 1:50:53Speaker 01

  Right? That's just not possible.

• 1:50:55Ben Gilbert?

  And how are you scoping it? Because you probably need Paul Graham, too.

• 1:50:58Speaker 01

  Well, yeah, I mean, you got Paul Graham is in the running for sure. But that's like a number of startups, but there's a lot of big ones in there. You have big impacts. So Paul Graham's definitely running, but okay, so do you go with? John Doerr is in there along with, so if you're doing firms, it's a lot easier because you get Kosla, Doerr, and

• 1:51:18Speaker 01

  Perkins, Tom Perkins, you get the three of them at once.

• 1:51:20David Rosenthal?

  Yeah.

• 1:51:20Speaker 01

  You do Sequoia.

• 1:51:21David Rosenthal?

  Which people forget, Vinnie Kosla spent a decade at Kleiner Perkins with John Doerr.

• 1:51:27Speaker 01

  Yeah, and you, and you had, yeah, so I mean, you look at that firm, it's like, that's like the OKC with like James Harden, you know, whatever. But then you have Doug Leoni, Mike Moritz and Valentine.

• 1:51:41David Rosenthal?

  Rudolph.

• 1:51:42Speaker 01

  Well, Rudolph's next generation.

• 1:51:43David Rosenthal?

  Yeah, but you had all of them there active all at the same time.

• 1:51:45Speaker 01

  For those 30 years. And it's like, well, that's Mount Rushmore, right? So if it's a Mount Rushmore of Mount Rushmore's, is kind of how you might look at it. You know, you definitely have to have the Sequoia and Kleiner.

• 1:51:56David Rosenthal?

  You got it.

• 1:51:56Speaker 01

  You gotta have, you gotta have Bill Gurley.

• 1:51:57Ben Gilbert?

  The Fab Four era of.

• 1:51:59David Rosenthal?

  The Fab Four era of Benchmark was truly something special.

• 1:52:01Speaker 01

  Yeah, so I mean, it's kind of like, it kind of builds itself, the Mount Rushmore right now, right? It's going to be Sequoia, Kleiner, Benchmark. And then we're like, we're going to have a big debate on the fourth arm, right?

• 1:52:13David Rosenthal?

  Yeah.

• 1:52:13Speaker 01

  Like, is it?

• 1:52:14Ben Gilbert?

  Well, it just depends how wide we're willing to scope it. Is it like traditional Series A type venture firms?

• 1:52:18Speaker 01

  I mean, is it Angelus, Naval? You know, that's had a huge impact.

• 1:52:21David Rosenthal?

  Do you put YC in there? Do you put?

• 1:52:22Speaker 01

  YC or Techstars, both have a huge impact. Do you put, you know, who else could be in there? That's just.

• 1:52:30David Rosenthal?

  You can argue for a founder's fund.

• 1:52:31Ben Gilbert?

  You can say YC and Techstars.

• 1:52:33Speaker 01

  Not yet.

• 1:52:33Ben Gilbert?

  It's totally different.

• 1:52:34Speaker 01

  It's on the way.

• 1:52:35Ben Gilbert?

  YC is like.

• 1:52:36Speaker 01

  Yeah, for sure. I mean.

• 1:52:38Ben Gilbert?

  Three orders of magnitude more significant.

• 1:52:40Speaker 01

  They've done the same number of companies, I think, but just in terms of returns, yes. But Techstars, I think, was a little before Y Combinator, but anyway, you definitely Y Combinator's, you know, in the running for that fourth spot, I guess. And then who else would you put in there? Masa? Well, no, I mean, but that maybe on the industry.

• 1:52:58Ben Gilbert?

  Maybe I mean, I don't know, depending on.

• 1:53:01Speaker 01

  Excel would be in the running for sure. Ron Conway.

• 1:53:04Ben Gilbert?

  I think the way you kind of have to define it, which is unfortunate because it means that it's going to be a long ass time before your firm hits Mount Rushmore is three successful generational transitions where each of the generations would have been on Mount Rushmore.

• 1:53:16Speaker 01

  All right. So then let's just do this. Instead of Mount Rushmore, because you're, we're talking firms. So for firms, you do Mount Rushmore. Right. So I think if you were just going to say the Hall of Fame.

• 1:53:25Ben Gilbert?

  Yeah. Oh, yeah.

• 1:53:26Speaker 01

  Just the Hall of Fame.

• 1:53:27Ben Gilbert?

  Yeah.

• 1:53:28Speaker 01

  And the Hall of Fame has, let's just say.

• 1:53:30Ben Gilbert?

  Oh dude, we should open the venture capital Hall of Fame.

• 1:53:34Speaker 01

  Capital allocator Hall of Fame, top 25.

• 1:53:36David Rosenthal?

  I was trying to figure out when we were doing the benchmark episode research, which will be out by the time this comes out.

• 1:53:42Ben Gilbert?

  Yeah.

• 1:53:42David Rosenthal?

  Uh, 2480 Sand Hill Road is a very special building. It was the forethought PowerPoint.

• 1:53:49Ben Gilbert?

  The quadrants complex.

• 1:53:50David Rosenthal?

  Quadrants complex.

• 1:53:51Ben Gilbert?

  Yeah.

• 1:53:52David Rosenthal?

  Office. Then it was Microsoft.

• 1:53:53Speaker 01

  We're the only three people who give a shit about this.

• 1:53:55David Rosenthal?

  Oh, no.

• 1:53:56Speaker 01

  This is the internet.

• 1:53:57Ben Gilbert?

  This is the internet.

• 1:53:59Speaker 01

  It's like, wow.

• 1:54:00Ben Gilbert?

  We have aggregated all the other people.

• 1:54:02David Rosenthal?

  Everybody else who cares about this is listening right now.

• 1:54:04Speaker 01

  Yeah. And like Sebastian, who wrote the parallels.

• 1:54:07David Rosenthal?

  Yeah, yeah, yeah.

• 1:54:08Speaker 01

  You guys are taking this way too seriously. It's not that important.

• 1:54:10Ben Gilbert?

  But then we're like alone yelling in David's house about a fictional Hall of Fame.

• 1:54:14David Rosenthal?

  TVI Merrill Pickard.

• 1:54:16Ben Gilbert?

  TVI. That's a good.

• 1:54:18David Rosenthal?

  August Capital, Benchmark Capital, Shasta Capital, all in the same building. And I think there's some space for rent in there. I don't want to go live down there, but like, I think we got to take out a lease just to put the museum, the Hall of Fame.

• 1:54:31Speaker 01

  A venture capital Hall of Fame is something we could collaborate on. We should just do it. Fuck it. We'll just do it like.

• 1:54:35David Rosenthal?

  Yeah. Yeah.

• 1:54:36Speaker 01

  We'll just, we'll do it like every year. We induct somebody. We'll get up there, the three of us and be like, this year we're inducting.

• 1:54:42Ben Gilbert?

  There should totally be a Hall of Fame. We should totally do this.

• 1:54:44David Rosenthal?

  Kid Ohio exists.

• 1:54:46Speaker 01

  Hilarious.

• 1:54:46David Rosenthal?

  You know, Cooperstown.

• 1:54:47Speaker 01

  Well, there is a, what do you call it? There, it'd be our Cooperstown.

• 1:54:50David Rosenthal?

  Yeah.

• 1:54:51Speaker 01

  There is the computer history museum, but that's for the PC, which is totally valid, but it's not for capital allocator.

• 1:54:58David Rosenthal?

  It's not for people. Like, yeah, there should be a Hall of Fame.

• 1:55:00Ben Gilbert?

  And do we, like, do we Midas list style, ask people for the real hard truth numbers?

• 1:55:04Speaker 01

  No, no, it's about impact. You have to think.

• 1:55:06David Rosenthal?

  We decide, the three of us. We decide.

• 1:55:08Speaker 01

  It has to be impact on the game.

• 1:55:09Ben Gilbert?

  Does the N D C A have like a lifetime achievement award? Is that the closest thing?

• 1:55:13David Rosenthal?

  It doesn't really exist anymore.

• 1:55:14Speaker 01

  Yeah, no, it's, it's about impact. Legacy, like the intent of the person.

• 1:55:20Ben Gilbert?

  Right.

• 1:55:20Speaker 01

  This is why like Paul Graham would be like, you know, first ballot. This is why.

• 1:55:25David Rosenthal?

  Yeah. Okay, who are the first ballot entrants?

• 1:55:28Speaker 01

  So obvious.

• 1:55:29Ben Gilbert?

  We've already talked about it.

• 1:55:30Speaker 01

  We already talked about it. Those are all first ballot.

• 1:55:32David Rosenthal?

  Do we have anybody who we haven't talked about or who is not obvious, but would be a first ballot?

• 1:55:35Speaker 01

  Peter Thiel. This is what I'd say. If you're under 20 years, you're not like, just like, let's wait till you're 25 years in.

• 1:55:41David Rosenthal?

  Yeah, just like the sports Hall of Fame's, you gotta have a.

• 1:55:43Speaker 01

  Yeah, you gotta be, you're not playing in the league anymore. So Paul Graham's still playing in the league.

• 1:55:47Ben Gilbert?

  Does Jeff Bezos count?

• 1:55:49Speaker 01

  Well, I mean, how many investments has he made? That Google investment is crazy.

• 1:55:52Ben Gilbert?

  So there's that, but there's also like, I think Amazon is the best venture firm of all time. And just in terms of like, it's internal.

• 1:56:00Speaker 01

  Oh, yeah, yeah, no, no, no. But so, yes, capital allocating lowercase c, lowercase a. They've been great at placing bets.

• 1:56:05Ben Gilbert?

  But you're right. Jeff Bezos is probably the most successful angel of all time.

• 1:56:08Speaker 01

  Yeah, I mean, if you just did it on.

• 1:56:10Ben Gilbert?

  And LP.

• 1:56:11David Rosenthal?

  Yeah.

• 1:56:11Speaker 01

  You gotta do it on, you know, when you're, when you're looking at it, I think you gotta look at impact. Like, impact on a game, legacy. Like, so is Carmelo Anthony, Hall of Fame? Of course he is, but he didn't win a ring. But, you know, it's just, he's Carmelo Anthony, right? Like, or Charles Barkley, didn't win a ring, but.

• 1:56:26Ben Gilbert?

  Okay, so then we got like Arthur Rock. Like, you gotta look at like the founding father type.

• 1:56:30Speaker 01

  Of course, of course. Yeah, there's no doubt. I mean, that's like going back to Bob Cousy or whatever, going back to like some really like, you know, people who built the league kind of situation before it became the league, right? So you got the league and you have the people before the league, you have people in the league. You've got generational shit right here, you know, Patrick Ewing.

• 1:56:46Ben Gilbert?

  Yep.

• 1:56:46Speaker 01

  You know, because I think like, you look at Gurley, like he's part of that Patrick Ewing generation, right? Like that Hakeem Olajuwon, Charles Barkley generation. You start talking about founders fund or Y C or Angel List, like, okay, now you're talking about more modern era.

• 1:56:58Ben Gilbert?

  Yep.

• 1:56:59Speaker 01

  Still going, modern era, after 2000. But if you started before 2000, it's a different group.

• 1:57:04Ben Gilbert?

  Do you notice we haven't talked about Andreessen Horowitz in this conversation?

• 1:57:06Speaker 01

  Oh, God, who cares?

• 1:57:09David Rosenthal?

  No, impact on the game, they're in, they're in.

• 1:57:11Speaker 01

  I mean.

• 1:57:11David Rosenthal?

  Both of them are in, for sure, no doubt.

• 1:57:13Ben Gilbert?

  No, they totally are.

• 1:57:14Speaker 01

  I guess.

• 1:57:15David Rosenthal?

  Impact on the game?

• 1:57:16Ben Gilbert?

  They totally changed the game.

• 1:57:17Speaker 01

  I mean, I just feel like it's gratuitous, it's just like raising $10 billion, three funds a year. I want to see what happens with the crypto stuff. I think they're just an index of venture. I find it quite soulless, if I'm being honest. Like, I feel like it's a giant index on venture, and I don't think that their hearts are super into it.

• 1:57:34David Rosenthal?

  Well, I do think they have interesting ambitions, though. I think this, like.

• 1:57:37Speaker 01

  That's the problem. More ambition, it's more ambition than soulful.

• 1:57:40David Rosenthal?

  But there should be a JP Morgan or Goldman Sachs of Silicon Valley.

• 1:57:43Speaker 01

  And they are that, for sure.

• 1:57:44David Rosenthal?

  Yeah. Why is it, why does Goldman Sachs manage the money of entrepreneurs?

• 1:57:48Speaker 01

  I just feel it's too, okay, fine, but I just feel like it's, it's too, it's, it's like too premeditated and less soulful. I, I feel like it's a soulful business where like your intentionality and your relationship with the founders really matters.

• 1:58:03Ben Gilbert?

  It's not the craft. It's, I mean, it's like the literal antithesis of it.

• 1:58:06David Rosenthal?

  It's industrialization.

• 1:58:08Speaker 01

  It's the, yes, it's the industrialization of it, it's the, it's the factorization of it. And listen, I'm sure it'll be very successful. At the end of the day, all the returns will be great, except for the crypto stuff.

• 1:58:16Ben Gilbert?

  Well, I mean, there'll be mean reversion, because like, when you get the law of large numbers, you have mean reversion.

• 1:58:21Speaker 01

  Exactly. It will be mean reversion, for sure. I mean, that was, at some point, they leaked a lot of their returns, and they were like.

• 1:58:27Ben Gilbert?

  Eh, not fair, that was the 2015 thing.

• 1:58:28Speaker 01

  Well, they did, actually, it was early, so yeah, that was stupid that the journalists didn't understand it. But there were some older ones, but it was like during that time, like, you start comparing it to Sequoia or Benchmark. I think, I don't think it's gonna, I think in the R, it will not be comparable to Benchmark or Sequoia.

• 1:58:41Ben Gilbert?

  And we, I mean, made a lot of hay of the fact that they had, that they made $11 billion in profit on Coinbase, and like.

• 1:58:47David Rosenthal?

  Right, which is.

• 1:58:48Ben Gilbert?

  I do not think they sold out of that.

• 1:58:50Speaker 01

  No, they didn't.

• 1:58:50Ben Gilbert?

  So they did not make $11 billion in profit as of today.

• 1:58:53Speaker 01

  Well, I mean, it's timing is everything, we'll see, I mean.

• 1:58:56David Rosenthal?

  It's interesting, too, I mean, having just done this Benchmark episode, like, the Benchmark Fund VII, one of, if not the best institutional-sized fund of all time, just like unreal.

• 1:59:05Ben Gilbert?

  20 to 25x on.

• 1:59:06David Rosenthal?

  Even that, like, the, the fluctuation in the marks on that fund, and it'll probably, probably end up between 15 and 25x. Maybe, but like, but it fluctuates up, up and down so much.

• 1:59:17Speaker 01

  Of course. I mean, it's, we live in a very vol- volatile time right now. So, yeah, I like the Hall of Fame idea. It's kind of interesting.

• 1:59:23Ben Gilbert?

  I think we, that actually would be a fun thing.

• 1:59:25David Rosenthal?

  We should get some space on Sand Hill and put up.

• 1:59:27Speaker 01

  No, I just, we could just do it as like a dinner. We just literally have.

• 1:59:31David Rosenthal?

  We don't need a space.

• 1:59:32Speaker 01

  We get a, we get our, we could just start in a restaurant, but you could get like a little hall.

• 1:59:36David Rosenthal?

  Yeah.

• 1:59:37Speaker 01

  And say, we're going to induct into the Venture Capital Hall of Fame, the following people. And here they are. And we just have three pictures. Boom, boom, boom. And you just drop it and it's like, here's our three people. And then people come up and say something about the person.

• 1:59:48Ben Gilbert?

  And I think like you, you, we, we could do like the three who we would hope would be there. And then we'll have like.

• 1:59:55David Rosenthal?

  We do it like the sports where you have, the person who's being inducted chooses who inducts them.

• 2:00:01Ben Gilbert?

  Sure. Oh, that's fun.

• 2:00:02Speaker 01

  Yeah. So Ruloff does Doug or whoever does Maritz.

• 2:00:06David Rosenthal?

  Yep, yep.

• 2:00:07Speaker 01

  Sean Parker does Maritz.

• 2:00:11David Rosenthal?

  Mike chooses who, you know.

• 2:00:12Speaker 01

  Yeah, go, we can have Larry and Sergey come up.

• 2:00:14David Rosenthal?

  Jason Calacanis come up and be like.

• 2:00:15Speaker 01

  Larry and Sergey come up, obviously.

• 2:00:17David Rosenthal?

  Totally.

• 2:00:17Ben Gilbert?

  Yeah.

• 2:00:18Speaker 01

  Uh, John Doerr would, uh, ask Bezos. I mean, it's killer. It's a killer idea. I mean, we just do Bezos.

• 2:00:24David Rosenthal?

  Yep.

• 2:00:24Speaker 01

  Doug and Mike.

• 2:00:26David Rosenthal?

  Yep.

• 2:00:26Speaker 01

  And then.

• 2:00:28David Rosenthal?

  Who inducts Phil?

• 2:00:30Speaker 01

  In memoriam.

• 2:00:30Ben Gilbert?

  It, yes.

• 2:00:31Speaker 01

  You would do one in memoriam. So you do, you know, whatever.

• 2:00:34Ben Gilbert?

  Yes. Cause it would be anticlimactic if the only person, because we will induct Don first. And if the only person that we inducted that year wasn't a living person, who could attend?

• 2:00:42Speaker 01

  Yeah, you do a combo. You do a combo. Maybe it's four people a year, you know?

• 2:00:45David Rosenthal?

  Yeah.

• 2:00:45Speaker 01

  You have to think, how do you, you want to get to 25? So maybe it's, you want to get to 25 to 50 over 10, 20 years. So yeah, maybe it's three a year.

• 2:00:54Ben Gilbert?

  In order for this to like, feel good, I think you're right that it has to be about impact, not about returns.

• 2:00:59Speaker 01

  No, returns is like, so, that would be like saying it's like albums sold for the Rock and Roll Hall of Fame.

• 2:01:05Ben Gilbert?

  Right.

• 2:01:05Speaker 01

  There are people.

• 2:01:07Ben Gilbert?

  That'd be a very Andreessen Horowitz way to do it.

• 2:01:08Speaker 01

  That would, yeah, Andreessen, but oh, what's the total assets under management? You know, and it's like, okay, dude, we get it. Yeah.

• 2:01:13David Rosenthal?

  Nickelback sold a lot of albums.

• 2:01:15Speaker 01

  Yeah, they're the Nickelback of venture.

• 2:01:17David Rosenthal?

  No, I didn't mean that.

• 2:01:18Speaker 01

  You said that. You said it.

• 2:01:19David Rosenthal?

  I wasn't talking about Andreessen.

• 2:01:21Speaker 01

  Oh, God. Oh, God. Oh, God. Like a million, they sold tons of albums. I'm not saying that they're a million, but no, but there was like.

• 2:01:28David Rosenthal?

  Oh, boy.

• 2:01:29Speaker 01

  There, there's, you know, if you were to look at Ron Conway, does Ron Con- did Ron Conway, who had a bigger impact, Ron Conway or Andreessen? Like, I think it's a conversation. You know, and if you, because Ron Conway, when I came into the industry, like there was at one point, I was at a, um, the Crunchies. And Ron Conway, at one point, like somebody said, like, hey, can everybody stand up who said Ron Conway invest in their company? And 100 people stood up. And my mind was like, oh, whoa, angel investing is cool. I mean, I wasn't an angel investor at the time. It was, you know, long before I became a scout, but that I always remember that moment when like 100 people stood up.

• 2:02:03Ben Gilbert?

  That like inspired, partially inspired.

• 2:02:05David Rosenthal?

  Scout program, is that what gave you the, is that what like put you in business as an angel investor?

• 2:02:10Speaker 01

  The scout is what put me in business. What happened was I had.

• 2:02:12Ben Gilbert?

  Was your Uber investment you personally, or was that Sequoia's money?

• 2:02:15Speaker 01

  That was Sequoia's money, yeah. And we were like, Ruloff and I were trying to figure out like, do we let people know we're doing this or not? It was like a big controversy at the time. Like, we want to keep this stealthy, but I mean Travis knew, but you know, it was, it was a pretty great deal, you know, it was like, um.

• 2:02:30Ben Gilbert?

  You know, at the time. They carried 50/50.

• 2:02:31Speaker 01

  50/50 at the time. They dropped it down after that. Doug Meone was like, every time I'd see Doug Meone, he's like 50% carry.

• 2:02:36Ben Gilbert?

  And they had 30% carry at Sequoia at that point, I think.

• 2:02:40David Rosenthal?

  Whereas you, I mean, if I were you, I'd be like 50% carry to them. I can't believe it.

• 2:02:45Speaker 01

  Doug always, they're so classy. Doug always made a joke, would always make a joke. He was like, 50% carry. Oh God, we get 30, you get 50. It was just funny.

• 2:02:53Ben Gilbert?

  We get 30.

• 2:02:54David Rosenthal?

  We get a lot of it.

• 2:02:55Ben Gilbert?

  Pretty funny, pretty funny shit.

• 2:02:58Speaker 01

  No, listen, we are very lucky. I think if you look at what we do as capital allocators, I think it's a very special part of the, it's a very special function in the world. I take it very seriously, as you do for the retirees you're investing about half of, but also just think about humanity, and I don't mean to make it heady. But these companies do move the human species forward as.

• 2:03:18David Rosenthal?

  Look at Elon.

• 2:03:19Speaker 01

  Yeah, exactly. So the human species getting moved forward by, as Steve Jobs would say in those commercials, like this is the crazy ones. They do need fuel. They, you know, maybe don't have an idea of, you know, um, you know, if they should even build this company. And I think the capital allocators really come in and say, here's some fuel, you know, here, go fight that war, you know?

• 2:03:41David Rosenthal?

  It's fuel and it's belief too. I mean, like what you, your story about com.

• 2:03:44Speaker 01

  Yeah.

• 2:03:45David Rosenthal?

  Is not uncommon, I think amongst founders.

• 2:03:47Speaker 01

  Oh my God. I mean, look at, I mean, the stories about Don Valentine and Atari and other places where he was at Cisco, it's like, so we gotta get this thing back on the rails. This thing's going to zero.

• 2:03:56David Rosenthal?

  Yeah.

• 2:03:56Speaker 01

  You know, like, there's a lot of existential moments where things go to zero and like.

• 2:04:00Ben Gilbert?

  So can I ask you, as we start to like drift, drift toward the end of the episode here?

• 2:04:05David Rosenthal?

  That's your line. That's your favorite line.

• 2:04:06Speaker 01

  Drift.

• 2:04:07David Rosenthal?

  That's the Ben signature line. As a call us here to the end of the.

• 2:04:12Speaker 01

  As our time together.

• 2:04:13Ben Gilbert?

  Like, is this different enough from our normal show? Should we do this?

• 2:04:17Speaker 01

  Yeah, I think so.

• 2:04:18David Rosenthal?

  Yeah, do you like this?

• 2:04:19Speaker 01

  I think a casual glass of wine and just, you know, if you have friends of the pod and you want to go deep and talk about them and of a more casual way, sure. Yeah. I mean, I think it's a great way to just have somebody on again, you know? So if you profile somebody like, I forgot that I had, you had done like the first episode with me and that was more about my career and more details. And so I'm starting to tell stories over again. It's like, well, let's talk about some other stuff, right?

• 2:04:45David Rosenthal?

  Yeah.

• 2:04:45Speaker 01

  So I think it's like.

• 2:04:46David Rosenthal?

  This is a different context.

• 2:04:47Ben Gilbert?

  Our audience was one tenth the size at that point.

• 2:04:49David Rosenthal?

  Well, part of what we, you know, like Lex has done so great with his show.

• 2:04:53Speaker 01

  Yeah.

• 2:04:54David Rosenthal?

  But, but those type of conversations, but I feel like that's more, what's the right word? Our shows are about the business of tech.

• 2:05:02Speaker 01

  Yeah, no, his is intellectual dark. I don't know why he's in the tech vertical.

• 2:05:06David Rosenthal?

  But I like the format and like Kevin Rose used to do with the foundation series and like.

• 2:05:11Speaker 01

  Yeah, I mean, long form interviews like Howard. I mean, I think Joe Rogan stole it from Howard.

• 2:05:16David Rosenthal?

  Yeah.

• 2:05:16Speaker 01

  And I think it's now Lex stole it from Joe or I don't want to even say stole. I think, you know, inspired by.

• 2:05:22David Rosenthal?

  Yeah.

• 2:05:23Speaker 01

  So Lex is clearly inspired by Joe and Joe was, Joe was in the running to replace Jackie Martling on the Howard Stern Show. People don't know this. So he was very enamored with Stern.

• 2:05:38Speaker 01

  And he wanted to be Stern, I think. And he eventually has supplanted Stern in a way.

• 2:05:43David Rosenthal?

  He did, he did become Stern.

• 2:05:44Speaker 01

  Yeah, it did become Stern. And so, good on him. Yeah.

• 2:05:47David Rosenthal?

  Right down to the, you know, Sirius, Spotify, like right down to it. He became Stern.

• 2:05:51Speaker 01

  Doing a platform.

• 2:05:52David Rosenthal?

  Yeah, doing a platform.

• 2:05:53Speaker 01

  Which is what Stern did. Stern had multiple platform deals. He did syndication first, then he did the Sirius XM one, because it was a new platform and he built the platform. He used his number one show to build their platform, right? Which is, I think, what, yeah.

• 2:06:06David Rosenthal?

  Which this, but actually to bring it all the way full circle back to Charlie Rose, like, yeah, he was like a, you know, business, I mean, he did more than business, but like he would have.

• 2:06:13Speaker 01

  He did culture, business, anybody in New York, because New York, everybody in New York was pretty fucking interesting. So.

• 2:06:17David Rosenthal?

  Yeah.

• 2:06:17Speaker 01

  Yeah. You know, he could have somebody from Wall Street, a publisher, an author of, somebody who does films, you know? He would have like Spike Lee on it, you know? He'd have Woody Allen on. He would have. You know, any actress on who was doing something interesting, any novelist, Margaret Atwood, anybody, which is coming through New York on a press tour, you know, you, you would do your press tour and then you would just go chill with Charlie and you would get to do something long for him.

• 2:06:41David Rosenthal?

  Yeah.

• 2:06:41Speaker 01

  You know, it was like a little like sort of more jazzy, you know, a little bit more like acoustic. So I, I like this format for you guys.

• 2:06:48Ben Gilbert?

  Do you listen to Smart List at all? Do you know about that show?

• 2:06:51Speaker 01

  I, I have listened to one or two episodes. It's Bateman, Will.

• 2:06:54Ben Gilbert?

  Arnett.

• 2:06:55Speaker 01

  Arnett and then somebody else.

• 2:06:56Ben Gilbert?

  Yeah. The guy from Will and Grace, Sean.

• 2:06:58Speaker 01

  I don't know who that person is, but they bring on a surprise guest each time.

• 2:07:03Ben Gilbert?

  And, and they.

• 2:07:04Speaker 01

  The other people don't know.

• 2:07:05Ben Gilbert?

  Yes.

• 2:07:05Speaker 01

  So they're not prepared.

• 2:07:06Ben Gilbert?

  Yes. And it's like, it's like Katy Perry. It's like Chris Pratt.

• 2:07:10Speaker 01

  Yes. Become a big deal.

• 2:07:11Ben Gilbert?

  I kinda wanna do that of tech, but like.

• 2:07:14David Rosenthal?

  Wait, you and I don't know who the, one of us is bringing somebody down.

• 2:07:17Speaker 01

  You guys are not good. You can't make, you gotta know the person's background much better.

• 2:07:21Ben Gilbert?

  But they all seem to know.

• 2:07:23Speaker 01

  A certain charisma with them that our industry doesn't have.

• 2:07:25David Rosenthal?

  Yeah.

• 2:07:26Ben Gilbert?

  But maybe it doesn't have to be a surprise as much as like.

• 2:07:29Speaker 01

  That's true.

• 2:07:29Ben Gilbert?

  Well, the, the other thing is that it, even though they have guests, the show is actually about them. The guest is a prop.

• 2:07:36Speaker 01

  In a way, yeah, I guess. I've only listened to one or two, you know, I see it in the rankings. Like it does incredibly well. Like it's a top 10 or top 25 podcast. Is it part of a network? Is it part of Spotify or something? I don't think so. Cause I see it on iTunes.

• 2:07:49Ben Gilbert?

  I don't think so.

• 2:07:50Speaker 01

  It's really weird that like Spotify doesn't allow Joe Rogan and Call Her Daddy on iTunes because the advertising would be huge.

• 2:08:02David Rosenthal?

  Right.

• 2:08:03Speaker 01

  So why not bake the ads in and put them over there?

• 2:08:05Ben Gilbert?

  There's some MBA that's run the numbers that says it's more valuable if it's driving new subscribers to Spotify.

• 2:08:10Speaker 01

  I guess that's it. I guess that's it. Yeah. Oh, guess you know what? They wanna be able to have those new subscribers when they go renegotiate with the.

• 2:08:16Ben Gilbert?

  Yeah.

• 2:08:16Speaker 01

  Music. I saw they're doing audiobooks too now. That's the next piece.

• 2:08:19David Rosenthal?

  Yeah, that is the next piece.

• 2:08:20Speaker 01

  Yeah. They're doing audiobooks, one-off purchases. Smart. I mean, audio is great.

• 2:08:24David Rosenthal?

  All right. It's getting really hot in here.

• 2:08:26Ben Gilbert?

  It's getting super hot.

• 2:08:27Speaker 01

  For those of you who don't know, we're in like.

• 2:08:30Ben Gilbert?

  A sauna.

• 2:08:30Speaker 01

  A new, yeah, David's new house.

• 2:08:33Ben Gilbert?

  David just moved.

• 2:08:34Speaker 01

  David's got a new empty house.

• 2:08:35Ben Gilbert?

  We.

• 2:08:36David Rosenthal?

  There's no air conditioning.

• 2:08:37Speaker 01

  It's sort of like The Shining.

• 2:08:39Ben Gilbert?

  There's no furniture. We just furnished this room.

• 2:08:41David Rosenthal?

  Literally, this is all from Craigslist, all of it, literally, in the last like two days.

• 2:08:46Ben Gilbert?

  That explains the smell.

• 2:08:46David Rosenthal?

  That, alright.

• 2:08:47Speaker 01

  You could, I mean, listen, you're rich, dude. Just go on and buy some crate and barrel.

• 2:08:51Ben Gilbert?

  We can't all be Jason Calacanis.

• 2:08:53Speaker 01

  No, come on, man. I know those fees. Oh, my God.

• 2:08:55David Rosenthal?

  Craigslist, I love Craigslist. I love it.

• 2:08:59Ben Gilbert?

  You buy used furniture on Craigslist?

• 2:09:00David Rosenthal?

  All the time. I do not buy new furniture.

• 2:09:02Speaker 01

  Alright, let's kind of stop.

• 2:09:03Ben Gilbert?

  I bought a temporary couch on Craigslist.

• 2:09:05Speaker 01

  It's the thrill of the, of the.

• 2:09:07Ben Gilbert?

  No.

• 2:09:07Speaker 01

  You're gonna get robbed. Don't do it. It's too crazy. Craig Newmark, I love you, but.

• 2:09:11Ben Gilbert?

  Alright, with that.

• 2:09:12Speaker 01

  With that.

• 2:09:13Ben Gilbert?

  Our thank you to Vanta.

• 2:09:15Speaker 01

  Oh, vanta.com slash acquired. Vanta.com slash acquired.

• 2:09:22Ben Gilbert?

  Our thank you also, you don't know who the other sponsors are because we haven't, we didn't record them live with you because we like, we felt very strongly that it was, you know, we wanted to make better use of your time.

• 2:09:31Speaker 01

  I love reading that. Are you kidding me?

• 2:09:32Ben Gilbert?

  Do you want to read our Brex ad?

• 2:09:35Speaker 01

  They don't sponsor my pod, so no. Brex, maybe they have. I don't know.

• 2:09:38Ben Gilbert?

  There's also a lot of ad living in it.

• 2:09:39Speaker 01

  It's about Brex.

• 2:09:40David Rosenthal?

  Brex, yeah.

• 2:09:41Speaker 01

  I know a lot of people who use Brex. I think we use Brex. At one of my companies.

• 2:09:45Ben Gilbert?

  If you're enterprise, if you're global, by far the best corporate spend management.

• 2:09:49David Rosenthal?

  It's much more than a card now.

• 2:09:50Speaker 01

  Yeah, for expenses and everything like that, right? And then they've kind of expanded behind that. So you can give cards to each of your employees and then if they screw up, you can turn it off or something.

• 2:10:00Ben Gilbert?

  Yes, exactly.

• 2:10:00Speaker 01

  They jump free, approve some budgets. Yeah, you don't want people jumping the fence and going crazy.

• 2:10:04Ben Gilbert?

  Well, all the listeners know because they, they heard it like an hour ago. They're very familiar.

• 2:10:08Speaker 01

  Oh, because it's in here. Yeah. So anyway, thanks. Shout out Brex.

• 2:10:10Ben Gilbert?

  So that's Brex.

• 2:10:10Speaker 01

  Shout out Brex.

• 2:10:11Ben Gilbert?

  And then.

• 2:10:12Speaker 01

  Use the promo code twist.

• 2:10:12Ben Gilbert?

  We share, we share this last sponsor.

• 2:10:16David Rosenthal?

  These are, these are great folks.

• 2:10:17Ben Gilbert?

  These are, these are like dear friends and, and geniuses and rack contours.

• 2:10:23Speaker 01

  Masterworks?

• 2:10:24David Rosenthal?

  No, no, no. Good guess, though.

• 2:10:26Ben Gilbert?

  Think smaller but bigger.

• 2:10:29David Rosenthal?

  Literally small.

• 2:10:31Speaker 01

  Gosh, I can't.

• 2:10:32Ben Gilbert?

  But secretly huge.

• 2:10:33David Rosenthal?

  Tiny.

• 2:10:34Speaker 01

  Oh, tiny, of course. Yes, they're buying companies.

• 2:10:37Ben Gilbert?

  They're buying companies.

• 2:10:38Speaker 01

  They're doing a good job. Yes, they're creating like the Berkshire of.

• 2:10:42David Rosenthal?

  Of.

• 2:10:42Ben Gilbert?

  The internet.

• 2:10:43Speaker 01

  The internet.

• 2:10:43Ben Gilbert?

  And can you imagine a better time to get the monkey off your back of venture capital?

• 2:10:48Speaker 01

  Yes, sell your company. Secure the bag.

• 2:10:51David Rosenthal?

  Secure the bag. That's my favorite takeout line.

• 2:10:54Speaker 01

  Secure the bag. Let's go, man. Trust me. If you haven't secured the bag yet, it's a wonderful experience, man. There's nothing like getting home with the bag. You get that tiny bag.

• 2:11:02David Rosenthal?

  You get that AOL weblogs exit.

• 2:11:03Speaker 01

  Oh, man. Let me tell you something. I'll tell you the story.

• 2:11:06David Rosenthal?

  What did you do when you secured the bag?

• 2:11:08Speaker 01

  I'll tell you what happened. I got, it's a funny story. I'm in my office and I got Bank of America and I got like low thousands of dollars in my bank account. I got an American Express card with 10, negative 10 on it and a Visa with negative five or 10 on it. And I'm sitting there and they're like, oh, wires are good. You know, the BD people are AOL. And so I'm like hitting refresh.

• 2:11:29Ben Gilbert?

  Yeah.

• 2:11:30Speaker 01

  On the thing.

• 2:11:31Ben Gilbert?

  This is 2006, 7?

• 2:11:33Speaker 01

  Five or six. Yeah. I'm hitting refresh. I'm hitting refresh. And then bing, bing, bing, bing, bing. You know, all the numbers come in for the whole, you know, amount.

• 2:11:43Ben Gilbert?

  And you own most of weblogs, eh?

• 2:11:44Speaker 01

  Uh, Brian and I were equal partners. Then we had Peter Rohoff had some ownership and then Mark Cuban was our big investor. Uh, and by big investor, he put 300K in for 5%. So that was a great outcome for him.

• 2:11:55Ben Gilbert?

  Oh, wow.

• 2:11:56Speaker 01

  Yeah. Uh, or more, maybe on 10%. I think on 10%. Anyway, long story short, uh, my wife comes in. She said, you okay? And I said, what? She said, are you crying? And I reached up and I had a tear in my eye.

• 2:12:11David Rosenthal?

  You're like, this is a new experience. I've never had this before.

• 2:12:13Speaker 01

  And she said, I said, she said, why are you crying? And I said, I'll never, my family will never have to worry about money again. Cause I spent my whole life worrying about money.

• 2:12:21Ben Gilbert?

  Yeah.

• 2:12:22Speaker 01

  You know, my dad had lost the business. It was a very cathartic thing for me. And I think people, you know, who are already rich, uh, you know, or maybe who come from means just they don't understand the concept of living with the fear of being broke and in debt all the time. And then when you have the bag, you secure that tiny bag. It's a tiny bag, but it's filled with diamonds and cash. You just open it up and say, thank you, Tiny. Thank you Tiny for securing the bag.

• 2:12:51David Rosenthal?

  Acquired dot FM slash Tiny.

• 2:12:54Ben Gilbert?

  No, it's literally, they only give us a thing.

• 2:12:55David Rosenthal?

  Oh, they don't, they don't.

• 2:12:56Speaker 01

  No, they just want you to know Tiny will help you secure the bag.

• 2:12:59David Rosenthal?

  Is it Hyatt Tiny?

• 2:12:59Ben Gilbert?

  Uh, and tell them that David sent you.

• 2:13:01Speaker 01

  Whatever it is, like, just know that Tiny will.

• 2:13:02David Rosenthal?

  Tell them that Ben, David and Jason sent you.

• 2:13:05Ben Gilbert?

  You can mention Jason, yeah.

• 2:13:06Speaker 01

  But I did buy a One Touch Espresso machine. I bought a Jura One Touch Espresso machine, which at the time was like two grand. And I was like, this is unbelievable.

• 2:13:14David Rosenthal?

  That's the.

• 2:13:15Speaker 01

  Then I tried to buy a Ferrari. And they wouldn't sell it to me in Beverly Hills.

• 2:13:21Ben Gilbert?

  You were the riffraff? No new money or something? What's the?

• 2:13:24Speaker 01

  Yeah, basically. I went in there and they're like, oh, yeah, what do you, I like to buy a Ferrari, uh, today, the 430. And they're like, oh, we don't have any available. And I was like, okay, can I put myself on the waitlist? We're not taking names on the waitlist. So I said to this guy, can I ask, what do you do here? He's like, we sell Ferraris. I'm like, to who?

• 2:13:40David Rosenthal?

  This actually, no, this is part of their strategy though.

• 2:13:42Speaker 01

  It's part of the strategy.

• 2:13:43David Rosenthal?

  It's part of the strategy, was they have the Ferraris, but they don't sell the Ferraris to build the steam.

• 2:13:47Speaker 01

  We're not putting anybody on your list. So I was like, well, how long is the waitlist? He's like.

• 2:13:52David Rosenthal?

  Don't even bother getting on it.

• 2:13:53Speaker 01

  I was like, okay. I was like, I'm a cash buyer. He's like, everybody's a cash buyer. I'm like, okay.

• 2:14:01Speaker 01

  Can I ask you a question then? And he's like, sure, come into my office, we'll have espresso, you want some Pellegrino? I was like, I'm good. Like, literally offer me Pellegrino espresso. And I was like, I was like, I have the same One Touch, Jura. And like, this like Italian guy's like, um, I was like, I don't mean to be rude, but what do you do here all day? He's like, well, we deliver the cars and we service them and we sell used cars, pre-owned, certified.

• 2:14:21Ben Gilbert?

  For more.

• 2:14:21Speaker 01

  And I was like, oh, I was like, well, I would take a pre-owned one. He's like, oh, well, the one you're looking at is pre-owned. I was like, no, no, no. The one I'm looking at, the 430, the red one out there, that's the one I want. That's got a sticker in the window. He's like, yeah, yeah. We certify them. We put the sticker on the window. I was like, oh, well, that goes for $230,000 or whatever. And so, uh, yeah, what do you want for it? He's like, 300.

• 2:14:44David Rosenthal?

  You're like, the sticker says 300.

• 2:14:46Speaker 01

  This is the protected leak table. I was like, the used one I was looking at. He's like, you can't get these cars. And I was like, ah. So you pay over seventy thousand. He's like, it only has two thousand miles on it. And I was like, two thousand miles, it's seventy thousand more than new. I said, why wouldn't I buy a new? He's like, because you can't get them. And I just, I'm such an idiot from Brooklyn who doesn't understand the concept that people would pay over for the car. And I'm just perplexed. That would bother me too. I was like, all right, well, let me think about it. And I left and then I was with my friend and I was like, um, and I had the rob report and it said like, number one car was the Ferrari F thirty. And I turn the page, it was Corvette C six was the number two car. And the starting line was make Ferrari, buy two for half the price of a Ferrari and beat them off the line.

• 2:15:31Speaker 01

  Or something like that. And I was like, let's go to the Corvette, let's go to the Chevy store. Let's go to the Chevy store. I walk in, there's Corvettes everywhere. The guy looks at me, he goes, you want to buy a Corvette? I said, yeah. He said, if you buy a Corvette today, I'll give you five thousand dollars off. I was like, yeah. So we go out in the four oh five and we're driving the Corvette and he's like, this is a Corvette, son. I'm like, you're going seventy miles an hour. I'm not selling, I said, I'm not, he says, I'm not selling this car to you unless you hit that gas much harder. And I said, okay. And I punch it to a hundred miles per hour. The guy's like, yeah, how does that feel? I'm like, great. That guy's good at this job. I come home with a Corvette. I come home with a yellow convertible Corvette. My wife's like, what happened to the Ferrari? I was like, this thing only costs sixty five grand. It's like seventy and I got five grand off. And it's American, baby.

• 2:16:16Speaker 01

  And it's American. And that was the car that I famously, uh, was, according to Gawker, Robert Scob, myself and Elon, when Elon got the first P one of the Roadster. Right. He was like, I got it. I was like, oh, let's meet in Brentwood. And we were driving them at a. You were racing. You were racing. We were driving them along Sunset Boulevard. A spirited drive. A spirited drive along Sunset Boulevard and we did it like five times. And five out of five times, the Tesla just destroyed the Corvette. And I was like, I'm doing something wrong. And you know, then we switched cars. I mean, and I was like, nope, electric's just going to beat everything. And this was the first one. That, you know, first, yeah.

• 2:16:57David Rosenthal?

  It's amazing.

• 2:16:58Speaker 01

  The prototype. That's in space right now. It's the cherry red one that's in space.

• 2:17:01David Rosenthal?

  That's the one that's in.

• 2:17:02Speaker 01

  And there's a famous photo of me and Elon in front of the Corvette. Uh, that one's it, but there's a famous photo of the two of us, uh, you know, in front of my Corvette and his P1. Uh, and I remember that night like it was yesterday because we were, this is before the iPhone, you realize like Robert Scob was recording this on his Nokia, you know,

• 2:17:20Ben Gilbert?

  Dude, these are the memories, right? Like this is the journey that you've been on.

• 2:17:24Speaker 01

  Yeah, it's pretty crazy.

• 2:17:25Ben Gilbert?

  This is the stuff you just will cherish forever.

• 2:17:27Speaker 01

  My life is unbelievable. I am so grateful for it and uh, thanks for having me on the pod, guys.

• 2:17:33Ben Gilbert?

  Listeners, thank you so much. Acquired.fm/Slack. Come join us. We'd love your feedback.

• 2:17:37Speaker 01

  Oh, Slack's cool. I gotta pop over there.

• 2:17:39Ben Gilbert?

  New shtick. Acquired.fm/Store. You can buy cool shirts.

• 2:17:44Speaker 01

  Shag.

• 2:17:44Ben Gilbert?

  Uh, slash jobs. Find your next career experience.

• 2:17:47David Rosenthal?

  Craigslist. You can get a couch.

• 2:17:49Ben Gilbert?

  That's right. Acquired.fm/David buys you some smelly furniture. My God, it is hot in here.

• 2:17:53Speaker 01

  All right, we gotta, we gotta eat some food. Let's have some sushi here in Mexico. I don't know what we're going for here.

• 2:17:59David Rosenthal?

  Oh, so fun. Thank you so much.

• 2:18:00Speaker 01

  Of course.

• 2:18:02Ben Gilbert?

  All right, listeners. We hope you enjoyed that, uh, very first Acquired Sessions with Jason Calacanis. It's a new format we're playing with. We would love your thoughts. [email protected] or tweet at us at AcquiredFM. And, uh, with that, listeners, we'll see you next time.

• 2:18:17David Rosenthal?

  We'll see you next time.