ACQ Sessions: Jason Calacanis

It was a magazine when you started. Magazine, yeah. That's how I started, yeah. Magazines was like the original platform for. Wait, have we started? Silicon Alley. I guess we started. This is the trick. We've just been recording the whole time. We just started, yeah, the whole time. Yeah, but I don't want to. Welcome to Applied Sessions. All that stuff that you said beforehand that, like, is really juicy, I don't think we should put that in. 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? This is the first in real life. But I think this is our ninth, tenth together, something like that. A lot. Between the two pods, yeah, for sure. Great to know you, boys. So this is the first Acquired Sessions. Acquired Sessions. I feel like I should get out a guitar here and just play some Dylan. This is your baby. What is Acquired Sessions? Acquired Sessions is. Normally on the show, we are, like, so scripted. Yeah, you are. And we have a great time. We do four-hour. We do four-hour episodes. You know, it's awesome. But really, for folks like you, who we know really well, what happens if we throw out the script? And just chop it up. And we just chop it up. David Rosenthal unplugged. Wow. I love it. I love it. This is the literally MTV unplugged. Literally. 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. Then you're done. But in an AI-first world, that doesn't hold up anymore. 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. 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. 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. 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 slash 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. So in the juicy stuff earlier, you mentioned Mahalo. Yeah. Is that why you started the podcast? Can we just keep referring to the juicy stuff? Yeah, the juicy stuff. Yeah, no, we weren't talking about that stuff. That stuff. Yeah, yeah, yeah. Is Mahalo why you started, you went from print to print to? 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 feds 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. And I 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. Were you set to go to college somewhere else? 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 going to see if I can go to college and make that work. So I'm going to go to Brooklyn College. So I decided to work during the day. And then I went to school four nights a week, 6 to 9 p.m. 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-baud modem, which then became a 1200-baud modem on my PC Junior. So it kind of, 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. He must have cleaned up on that. Oh, my God. It was crazy. And so I just got exposure to video games and computers. And I was like, wow, this is incredible. Computers are going to change everything. And then I happened to hack some software. We used to run a lot of scams. You told us about the VHS. 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 would make copies of, like, Chess Master and stuff like that and then sell them for $10. And then we started, like, hacking and doing what was called phone freakings. When you were doing this stuff, like, you had to be reasonably technical to do it. Not like, you know, not like Wozniak technical, but like. We soldered chips sometimes. We changed. Yeah. 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. 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 going to be the guy doing the boards. I'm going to be the guy writing about the people doing the boards. It's a very good question. I used to go to Bleeker Street. 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. It's like blogs before blogs. 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 services and CD-ROMs. And I did it with my friend, Brian Alvey, whom you might have heard of. And I did it with my friend, Brian Alvey, who you might have heard of. We went to high school together. We did weblogs. We did weblogs together. Yeah. But in the early 90s, I did Cyber Surfer. Just Engadget, Twad. All that stuff. Everything you sold to AOL. Everything I sold to AOL. But anyway, before that, I did that magazine. And then I met Jerry Colonna at Internet World, the first one. And there was a booth. That's right. When Jerry was a VC, before he was, like, the whisperer of startup coaches. Before he was a VC, he was consulting for Lycos. And I think CMGI. And so, there was a Lycos. There was a Lycos booth. And I had met this young lady at it. And we hit it off. And we were talking. And then she introduced me to Jerry Colonna. And then I met Jerry Colonna in an office no bigger than this room on Union Square. And he said, listen, I'm leaving Lycos. But I'm going to start this Hack Me 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. J.P. Morgan was going to back them for their venture firm. This was 1994, 95. This became Flatiron. It became Flatiron. J.P. Morgan was the first big anchor of Flatiron. They were half of it. And Masayoshi-san, Softbank. Was the other half. No way. So, they wanted you to come be a VC associate. Not a VC. Just to read business plans. So, the deal was they would take me for sushi and pay me $1,000. Wait. What do VC associates do besides just read business plans? Exactly. Well, anyway. It was a thing. And so, I had the magazine started, 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. That's where Flatiron made all their money. Yeah. They were going to invest anyway. And Flatiron became USV, right? Yeah. Square Ventures. Flatiron went with Jerry Colonna then when Jerry decided he wanted to move to Colorado and just chill. Yeah. 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. He wrote that great book about it. 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. This was before. Now, it's like, I do both. And now, it's like, I do both. Why choose? But just to back up to GeoCities, that sold to Yahoo for like $3 billion. $5 billion. And Flatiron was the main investor. Yeah, Flatiron maybe owned 5% or 10% of it at the time. It was like a huge win for them. I mean, Fred was on fire for a New York VC and Jerry. They did pretty well. How did that happen, right? I mean, Silicon Valley was here, but they were in New York. What was going on? There was a lot of good companies brewing in New York. And my concept with Silicon Valley Reporter was, well, they have Red Herring upside in the Bay. But I owned 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. That was kind of king of New York, right? I grew that business to $10 million in revenue off my credit cards. 75 to 100 people working for me, 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. What did your family think of this? 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 at its peak and you were the equivalent of Satoshi or something. It was crazy to be the New York internet guy. Can I? So we talked about a lot of this when we did our big Empire of Jason Calacanis episode with you. So I want to put this on pause so people can go listen to that. You should. It's great. We have a lot of great stuff. And you mentioned, I want to like take us from you're only as good as the, you know, your greatest, your, your newest thing. Sure. Um, cause the last time we talked to you, you were just starting all in and like, can we talk podcasting? Of course. I love it. Podcasting is like, I think perhaps my greatest medium. What happened with all in? How did, I mean, it's weird. Has it surpassed your wildest expectations? Um, I thought it would be something, Chamath and I would do 10 times. Yeah. So the, the origin story is pretty simple. Um, Chamath, uh, I knew because he was running ICQ. Chamath was running ICQ? At AOL. And I had sold my company to AOL and like the revolving door of AOL. I didn't know that was the lineage. It was like Ted Leonsis had this March to a billion. Uh, my Greek brother, a mentor had this like March to a million, a billion, uh, offsite. And so I went to this and I just sold weblogs. That was hot shit. That's the, that was the idea. Well, with weblogs Inc and with, uh, AOL and other assets they wanted to buy, they were going to March to a billion users. It was like this crazy rallying cry. And we had these t-shirts March to a billion. So I go to that and I see 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 was like, 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. I was like, it's hilarious. And he's like, yeah, but I'm leaving. I'm going to go, um, I'm going to go to the West coast. I'm going to go work at this VC or whatever. I was like, all right, nice seeing you. Um, and so then when he was there, I was in LA, uh, and what VC did he go work? Cause he was at Mayfield for a year. And then Sean Parker introduced him to, um, and Zuck needed, you know, like a Chamath. He needed like somebody who would just build 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 because you know, he too was very hungry. Um, and he was like, you guys must've been like brothers from another. Yeah, for sure. For sure. We're, we're, we're definitely, you know, both outsiders in Silicon Valley. And, um, you know, I had Chamath come on the pod this week in startups. That is, we listened to it. It was, it's fun to go back to that moment. And you know, he, you can see how he he's not, you know, polished. He's not Chamath, you know, as gregarious or whatever. It's a little more reserved. He doesn't have the Loro on. No Loro Piano. He was, was he in great shape or? No, no, not one of those. He was like a, he was like a dork, you know, like he, but he was, he was 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, uh, 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 or whatever. And so, which at this point you had an eye for, cause you were like, 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. I was like, I'm like, I'm like, I'm whatever is, you know, I introduced a lot of people to the world. 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 of thousand people. And then as now too, like you could be a great founder, you could be a great person in tech, but like that doesn't automatically make you a compelling podcast. 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, um, anyway, we, we started a friendship. We started playing cards together. Uh, we started hanging out, you know, trading notes kind of thing. And, uh, he's going to start his venture firm. I'm a scout at Sequoia, all that stuff. We started 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. Cause 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. We can start up at any time. It's twice a week now. And, uh, which it's now five times a week, six, five Sunday. I'm going to go, I may go back down to five next year. It's a little much right now. Um, I mean, we'll come back to this, but you're killing yourself right now and you're on act three. 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. Um, anyway, Chamath calls me, you know, coming out of the studio. I don't know if it was in, he was in New York or was he was in the one market one in San Francisco here. But, um, he said, I want to do this pod 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? I'm texting back and forth. I was like, we should call it all in. And this is 2020? Yeah. It's like two years ago or 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. I was like, all in. Cause you would, you'd been referring to this poker game on air on twice. 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. Saks, I had hosted it floating and putting all that together. Um, yeah, I'd referred to it many times in the pod, but tried to, you know, keep it from becoming public. Right. But it was me, Bill Gurley. It's all public now. Mark Pincus, right? Or maybe. Pincus used to come to the code one. Yeah. Um, which is another funny story. Um, and, uh, lots of funny stories in my life. But anyway, um, so then the pandemic came and the pandemic happens and we're like, well, where'd you go? I just dropping these little breadcrumbs. We got to pick them up. We got to pick these up. Anyway, at some point I'll write a biography. Anyway, um, nine years, uh, third book. Anyway, the, um, then we, we were, the pandemic starts to happen. Like, well, Saks has some ideas about masks and then Freedberg. Saks and Freedberg weren't, there was no besties originally, right? It was before all in. I mean, we knew each other. We were friends, but not besties. I was besties with Saks and Chamath and now Freedberg is a bestie. Um, and, but he, 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. Um, and I think, you know, I was a really good interviewer. I'd studied interview techniques and really, you know, after doing whatever, I'd done at least a thousand episodes of twist at that point. And I had, I had Saks on many times and Chamath. So I was very comfortable with them. And at the poker game, we break chops and I make jokes. Um, and Chamath's a great host and just very comfortable with each other. Uh, and, and Freedberg kind of joined that group and, um, it clicked. And I think during the pandemic, and I thought maybe this last 10, 20 episodes, but during the pandemic, I think people wanted information and I realized like perspective. I mean, I think that's a thing. I'll, I'll tell you, I've never expected to be listening to David Saks talk coming from where he comes from politically and where I come from politically and going, yeah, that is a good point. And that perspective is like so helpful in our polarized world today. 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, uh, Gore Vidal and, um, who is this adversary? Uh, anyway, it's a great documentary about Gore Vidal and, um, 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 sixties. They started debating like, uh, different convent political conventions. And it was like the most compelling thing on TV. But they were like friends. Best of enemies. Uh, they weren't besties like Saks and I are, but you know, Gore Vidal was just he was gay, um, kind of closeted or quietly gay. And on the left and Buckley was like a serious conservative. And they went to blow 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 sixties where like maybe some adults understood like, yeah, that's a gay man, but we don't say that. drive the Castro's right nearby and we saw a naked guy in the Castro and I was like oh naked guy in the castro like huge jacked dude walking around and and super sunny so he's like just all like slick down but did he have his shoes on was he wearing combat boots yeah 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 because you're gonna sit right right bare ass 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's like ah this is like a relic of the 60s 70s 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-hearted 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 right 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 uh calling the police and like this shit's about to go down oh my gosh you know and then here it's like you know high five and yeah live your life that's one of the things i love about san francisco but anyway the pod's gotten very big so you get the gang together and like yeah what why do you think it works like is it why do you think it works it's like the one ish tech in our business is number one of course but it's number it was number 28 last week like in the world you guys have transcended like this is more than just anymore yeah it has nothing to do with finance or tech anymore i think it works 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 are you and no pressure but are you going to be leaving soon because i'd love to camp out here and get to know you and i'm and they're like stop busting my balls jason looked at me and she goes j cal and i was like have we met and she's like no i listened to your pod twice a week i'm like it's only on one 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 wow 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 she's like i deeply care about san francisco politics no it's not how she had found it and this is you know during the pandemic situation then that's when i realized it had crossed over was there a moment for you either you for or you where you were like whoa this is you know i've been um micro famous you know micro celebrity multiple times in my career but this is york 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 now it's 20 you know or 10 and they want to take a selfie and it's you know just you know how podcasting is you guys get recognized and it creates a level of intimacy with people for sure if they're in the habit yes because you're hearing people every week and then people become characters and i try to make everybody i was you know in all on the show or in all honesty i did craft with all in i was very premeditated and creating some character i've never really talked about 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 right as i was gonna say and you know freeberg didn't even have a twitter handle well there's zero followers there's even a character of j cal on all in like there's how the world's greatest moderator sure yeah i think more like j cal the guy who lets himself be the punching bag because it plays for the show a little bit uh which is 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 you're like not much 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 you care about the environment well no it's also like i don't want to waste a ton of money and you know whatever reason um 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 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 them and i don't know i don't know i don't know i don't know i don't know 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 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 is i'm the poorest guy on the show but like i've done okay like what uh maybe let's flip it like for them before all in i mean maybe tamath had a little bit of a public no they were not famous they had no go to mark they're all they're all this is a new thing for each of them to hit this level of notoriety it's not for me what do you think for i mean we should ask them this sure like if you were to speculate caveat that it's speculation what do you think for them all in has like done like 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 um i think really by design he didn't 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 a session at all in summit uh 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 it wasn't a priority for him right so i'd be like all right i'll put bragg hersener in if you can't make it i'll try to get bill girley to show up or whoever draymond to fill in for him you know and it was always like i wonder if freebird will show up but he's actually really committed to the show now um for sax he was high profile but nobody really knew him as a republican so he kind of uncloaked as a republican on the show 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 payfail mafia one but he was like the least kind of public of the paypal mafia paypal mafia you would say elon reid hoffman peter tl max levchin jeremy stoppelman chad hurley ruloff yeah and i guess sax would be somewhere in that strata of like being known but i feel like that's being known being known yeah being known but yeah you know and i think part of the reason this works is sax i think sax has probably taken the brunt of the head of the pod yeah 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 him deal float on the margins probably i think there's probably i don't really margin i wonder i wonder he said that jokingly on the show i don't know i'm just thinking like maybe there's somebody has ascended because he's done all in in a way that 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 till's venture firm because i'm so liberal for sure there are and okay so those people feel that way about craft now but for every one of those there's 10 more 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 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 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 yeah you know i've 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 to five times but mostly that's a function of the fact that i've lived only in new york and california my life where you don't really get many republicans or moderates but i voted for bloomberg giuliani when bray was crazy and pataki who are all republicans to me were you here during the sports or were you still no i wasn't but i um i i like competent people and i supported bloomberg for president which got me a lot of flack really i don't understand why people were very upset that i was for him instead of whoever 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 uh liberal fiscal conservative yeah we were like everybody should be that but we're the smallest of the four groups yes it is a small group i i um i 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 pot off when that happens and they don't like it um and certainly i the maga group was has no love lost for jay gal i can tell you that like my replies have been really crazy i would get like brigaded the last couple of weeks nuts um it's funny but it's also like on the margins like they can get a lot of love from people who are get a little scary, like they'll dox me sometimes. times and i you know that's not fun um a handful of times this happened uh but you know i had to tell david like david i am not like i don't actually listen to msnbc and rachel maddow to get my information uh and by the way you're pro-choice pro-gay marriage anti-war yeah he's the dove and i i was like well okay if you if we don't play this game i'm gonna just dub you david the dove and now you're making me into jason the hawk like what are we talking about here like um but anyway you know it just goes to show how silly the coalition building is like it's totally like exactly the the two-party system requires that if you feel very strongly about something yeah then you're not allowed to think independently about anything else it's so crazy you know i 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 in any political office and you know it is just horrible on any number of levels but i believe that independent of his party he's a democrat obviously obviously yeah yeah and so like i would hate him as a democrat or a republican so it's not personal and i i would i would love or it is personal with him but it's very personal with the party yeah i mean i just think this is like 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 secure an office and that's all they care about is winning i get it whatever 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 and something and for some people that's the flat earth and for other people that's startups and for some people it's 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 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 i'm like let me look at the image quality versus the old one because it really is pretty 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 yeah 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 um he's like one of these supervisors here he's a super idiot like guy in san francisco who like um you know like won't let them build housing and stuff and he's like you're just a conservative 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 thank you for the latter my besties remind me on the ladder i'm working on it not trying to be a billionaire thank you all right listeners now is a great time to thank our longtime friend of the show service now if you are running a large enterprise ai agents are likely spread across every team and deploying them is uh no longer the hard part 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 exactly and the challenge with ai is governing it securing it measuring it and making sure that it actually delivers value that is why service now built the ai control tower 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 and service now can do this because they've spent more than 20 years building the operational backbone of the enterprise the workflows governance approval security controls and institutional knowledge that power how work actually works and how it's being done and how it's being done and how it's really gets done across it hr customer service finance and security service now already runs more than 100 billion workflows annually and trillions of transactions for more than 85 percent 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 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 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 slash acquired and tell them that ben and david sent you another thing that's really fascinating to me about all in yeah and you guys is 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 sb that all came from david philo and um david philo and jerry yang were driving their old cars right like the cool thing like you you could like make money build a company but like you never want to like you never and be understated you guys i think are the first like like you're you guys like whatever like we got a private jet like that's fine like you know 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 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 um with a small like outlier wealth creation and we don't think enough about inspiring people to create companies and learn and like the time i create the most controversies 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 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 and then you you know flip it you can build a business there like david senra over the founders podcast like mr beast mkbhd like nobody gave these guys permission equitable yeah but people want to spread a narrative that the world is unfair and like i think the world becomes so fair and so just and so much information 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 the world is still unfair i think i 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 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 that'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 virtuous signaling goodness 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 and they have to and it typically like is a certain type of person i'll just leave it at that okay can i so i'm going to your question founder university now i have a course where i teach people for 12 weeks um or i should say a team that teaches it and i'm going to actually teach it myself this next cohort where i just teach people how to start companies all right let's plug it how can they find out founder.university that's it there you go 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 excused absence if people miss something because of their kids or whatever fine but we just try to get people to complete it over 90 people complete it that's cool so and then we're investing 25k and 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 i'll maybe 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 like you have to have gone to stanford i'm like no i'm invested in 350 companies like maybe five percent of the founders went to stanford like no that's just not it's patently false like you know you have some confirmation dealing with a data set from 10, 20 years ago, I get it, but I'm 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. Nobody cares where you went to school. Nobody cares where you live anymore. Nobody cares where you live. They care about what you've built and your traction. 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. I mean, you say the M word, it freaks people the fuck out. I'm like, why is it so scary for you that Silicon Valley is a meritocracy? And they're like, because it's not. And I'm like, it kind of is. Can I answer your question earlier of why I think all in works? Yes. All right. Go ahead. So I think you've got the perfect storm of three things. The first thing is. A lot of theories on this out there, by the way. Billionaire porn. Most people. Okay. You're counter-positioned. Most people who attain that level of wealth crawl into a quiet hole and make sure no one knows about their private jets. You're doing shows from boats and jets. Yeah. So there's like. 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. In some peak moments of all in, it's like watching billions in real life. It's like 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 this interesting intrigue there. So bucket one is like billionaire porn. Bucket two is by the research you guys do 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. Like, somehow this is not making it to me. And this feels very. Like, a lot of it proved out to be like, this was good information before it was mass communicated. All four of us are information junkies with a lot of research and teams that could inform How many people. All in, how many people touch an episode of All In? One. Producer Nick, that's it. No, I mean, but like the research. I don't know. I'm pretty sure. There are text files open on people's computers when they're talking. 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. And I think Saks has some research help. I'm sure Friedberg and Chamath read the stories or they're well-read. I mean, 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. You do 20 meetings a week with founders. They're going to tell you everything about the world. Yeah. 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. And if you're hearing the right pitches, you actually are getting, like, cutting-edge information before it's widely available. Definitely. So, okay, that's number two. Yeah, we probably have a slight information edge. Yeah. 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. You weren't on the inside. 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. You get enough to run. 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. 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. Yep. Which is the third component you think makes it successful? It's the thing that David and I took forever to realize works about acquired, which is relationship and charisma. Yes. Like, people like having fun by listening to stuff. Sure. And so, like, if we. If we can make history fun, then people are going to listen to four hours of us diving into stuff you would never read in a book. And you guys do that in spades. Like, and it's just so fun to, like, temporarily join your world. I mean, the fact that you, as a podcaster who makes elite content, like top 100% content, find it compelling is just. Yeah, that's very. Listen every week. Don't miss it. I can't wait. Literally walking the baby up and down the hills, listening to. 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 was very. Don't take notes. Maybe I should take notes. 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. How did the Freeberg host episode come about? So one week. Yeah. You switched roles. Well, he was like, I think this could be done better. This could be better. And I was like, go ahead. And I was like, sure. I'll just shoot. And. You pass the rock and I'll. I was like, yeah, you want to be a point guard? Go ahead, show us. And he did a solid job. But let's be honest, like. He's not a point guard. It's not Showtime, that's for sure. Yeah. Like, I don't think people are going to go to watch him play point guard. I mean, he did a serviceable job. And. Put that on his tombstone. No. I mean, but he shines when I created Science Quarter for him to shine. Right. Bring me a sign. He's like, oh, you know, I don't know if I want to. I don't want to talk about politics. I was like, listen, Sax 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 made him the Sultan of Science. So good. You know, 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. Sax would disengage during science and quinoa. Disengage during. Disengage during politics. Yeah. And what I've been trying to do is keep both of them involved when the other is doing stuff. And Chamath and I are involved. That's a hard job. That's a delicate. Yeah, and 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, do they help? And I actually. Looked at the interjections. And if you look at McLaughlin, you guys did not grow up on McLaughlin. I'm not super unfamiliar with what this is. So the McLaughlin group was the best Sunday morning show. And it was so good, like SNL with 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 it became so competitive that you wanted to watch it. Now, what I didn't realize by adopting that would be. Be that Saks is the ultimate debater and will fight like a dog until he wins any debate. And so I may have pushed Saks 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. And then some people in the audience are like, you have to be the fact checker for Saks. And I'm like, no, that's not my role. I'm not real time fact checking Saks. And so that is. Yeah. Yeah. It's 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 in me. So I'm like, explain that. Right. And I'll stop somebody. Now. I mean, you're expanding the TAM to dentists. 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? Obviously, you know that term. Doing that for myself. You were, what, the third or fourth investor in Uber? Yeah. Like, exactly. Well played. I think he's been in Robinhood, too. Oh, calm, too? Wow. Who knows? And I'm like, dude, like, I'm asking that question on behalf of the audience. So when I'm moderating, 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. Right. Like, he'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. And that's what I think has brought in, to your point, a lot of the dentist crowd. And having an intimate sense of where your audience's edges are is a really important role there. It's an art. Like, when we have guests on, I'm always trying to catch where did they just go slightly too deep and I need to pull them up so that we. Yeah. And, you know, podcasting. It's 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? There's no clock in this room. Well, they're going down some rabbit hole that has never existed in media before. Right. So. 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. They just jumped into brain surgery. Yes. Let's just explain to us what's going on here. How are we going to chop up this brain? Right. Like, yeah. Yeah, it's a bit of an art. But, you know, I have to say, like, it's been a different muscle for me to flex. And it's been great fun for me. 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 uh 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 but i can't be yeah pauses sometimes sometimes you hit and rewind right let me make sure i get what he's saying here 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 a show it's comforting yeah it's like i love all the stuff he's talking about but like it's not you must listen every time every minute every second concept and i'm not using hard parts of my brain to understand all then has become candied vegetables it's both it's both yeah for sure yeah i thought i'd 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 right i mean what do you wait related but separate topic um silicon valley yeah i feel like dude especially there's a lot of part of the even the origins of all and there's a lot of like taking on san francisco politics and calvin like there's a lot of crap wrong here yeah but you guys are all still here how are you guys feeling about that yeah how do you how do you feel about that like what what do you think of the bay area um you know i lived in new york brooklyn and 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 like i enjoyed brooklyn and manhattan much more than la i enjoyed la much more than san francisco so i don't know where to go next but i'm gonna go somewhere like we said why are you still here then uh well i can't there's no reason for you to be 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 because if you wouldn't you'd always wonder well michael morris used to call me the mouth from the south they had like two investments in la oh the mouth from the south is here sir michael saying that but i moved up here and yes i love it up here it's quite bucolic my kids are loving it um it's quite nice i would love to live in another city in my life uh 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 gonna be uh damaged for a decade or two so i think for the rest of our adult lives this is going to be a big deal for us because of the pandemic or i think the politics and not appreciating the politics regulation and not appreciating the tech industry is really the problem um and then you look at this guy dean preston like he is dunking on um the founder of away and stewart butterfield from slack they're a couple yep 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 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 raise venture capital so you have one guy dean preston dunking on people saying we have this one percent so when they sold their 30 million dollar house we were able to extract a million two that's why tech doesn't like me i was like hey dummy yeah now that all the future earnings are gone now what's california marginal tax rate is 13.5 million dollars and i'm like i don't know i don't know i don't know i don't know i don't know what they're talking about i don't know i don't know i don't know what they're talking about i don't know i don't know what they're talking about they have an exit tax now for homes in san francisco right so if your home costs over 10 million when you sell it i mean i think it's just a sales tax 1.2 million from them selling their home versus 13 percent of their future earning stream literally the chef at slack made a billion two paid a billion two in taxes yeah from their rsus like are you such a where do you think a million two probably yeah like the bill the million two yeah but that order attitude probably paid in taxes on their rsus at slack yeah you absolute moron like you're literally so upset about their mansion and dunking and you're dunking on an individual's name uh but anyway the fact that we hate entrepreneurs who create jobs and wealth or certain people do it's just insane it's just insane like what 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 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 20 and you wanted everybody to have universal health care and he gave universal health care like that is literally what bezos did to them how embarrassing maybe you could argue that like them pushing him pushed it but no no yeah definitely it is literally him showing like uh as the amazon crew showing like let the free markets work like the doordash uber amazon starbucks absolute um and and battle to just hire entry-level employees and make it delightful for them is what has driven you know and a lack of immigration has is what has driven these uh salaries up right and the benefits up it's extraordinary what's happened with the free market this competition is still seven dollars federal minimum wage is seven and change still right uh and 15 here in the city uh in new york is 15 like yeah it's weird all right listeners now is a great time to talk about one of our favorite companies legora the agentic operating system for legal work yes most of you have dropped a contract into a chatbot by now but as a lawyer how far can that really take you it's never seen your firm's precedence it doesn't respect confidentiality and you can't check where its answer came from so legora's founders approached this the way that great founders do early on the team moved into the office of a big law firm in stockholm and learned for months how the work actually gets done a couple of thousands of enterprise customers and a hundred thousand users later they still work that way they employ a hundred legal engineers on staff these are lawyers sitting inside of firms and legal departments to deploy legora onto live situations like the deal closing this week or the policy review due friday the product has gotten very powerful in a short period of time a year ago the goal was a good answer from a chatbot with the legora agent you hand it the work and it comes back with a plan tasks like running diligence on a data room or reviewing a new vendor contract get completed inside the tool you use every day like microsoft word and against your own precedents and playbooks every finding is sourced the lawyer directs the work and signs off before the system executes any steps every legal team can get access to the same ai models so the models themselves do not give you an edge what you can do with your own data people playbooks that's the whole game today over a hundred thousand legal professionals at more than eighteen hundred law firms and in-house legal teams in over fifty markets use legora and when legora goes head to head with its top competitor in a pilot it wins seventy percent of the time a demo is one thing but what matters most is an associate who reaches for it at two in the morning during a closing or whether a general counsel trusts what it says before the board meeting so if your legal team wants to check it out whether you're at a firm or in-house go to legora.com slash acquired and be sure to tell them that ben and david sent you we reference this at the start of our conversation you're working as hard or harder than you ever have you said you've got a smarter a new well of energy yes tell us about it well i find great purpose in what i do and uh when my friend tony shea 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 and so what are the two buckets 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 um 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 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 um doing my podcast every day absolute joy entertaining an audience you know thinking uh thinking about the world and having these conversations i had toby from shopify on today like i leave the toby interview it's like it's third or fourth time on the pod that's awesome and it's just like instead of us having dinner or lunch we just record a pod the end um did you do it in person or did he no just you know on zoom he you know he just started because he did that tweet about his compensation tool yeah where you know here's your total comps you can use the slider i was like that's brilliant come on the show want to go on the show and talk about it's like yeah of course um 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 uh they every day get on there and they seem to love it and i do and so i just committed to doing it every day and i love it isn't it weird when there's something that takes a ton of work but somehow doesn't drain you 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 oh yeah who i respect and who's awesome and bring something to the table that i don't have and having she's so great having someone to play off of like i feel like that's the thing that's kept acquired going yeah is that like you and i can like i don't know how you did it alone for i don't know a decade uh well i you know i'd have guests on it was largely a guest driven show and then i would do the news round table 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 sell out i'll do it five six days a week whatever um and um i enjoy meeting with founders uh 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 yeah to me that's a very hard part of the job because it becomes very repetitive so how have you excised that well i created a platform found 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 yeah i don't really understands what i'm doing and i kind of like it that way but the angel syndicate is now the largest syndicate in the world i've deployed like 185 million dollars in my career as an angel investor i'm doing 50 million a year now that's awesome 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 and 12 on the investment side and of the investment team like people don't understand like oh you're a solo gp i'm like yeah with 12 people um those people are doing 60 introductory meetings per week six zero and then we're doing maybe 15 20 second meetings so there's it'll be 100 meetings a week shortly probably across 10 people or 12 people but you're not doing the i'm not doing them yeah uh and what happens is you had this line was it on it was on twist i think you know that's a lot of people say that's a lot of work but you're like yeah but now for me that is the new philosophy this is why my energy is really high this is your i have told everybody who comes to work for me i work 60 70 hours a week keep up if you can't keep up don't be here uh i'm looking for a you know a fixed 50 a solid 60 hours a week you don't have to match me 67 but 60 or 70 hours a week but keep up 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 i'm open to all of it yeah i'm open to all of it i don't they don't need to want to have my you know absurd um unhealthy a desire in my youth to be successful um and if they did they probably wouldn't come work for me but maybe they would actually i would uh so yeah they probably would not for very long yeah you'd come you'd learn three years you'd extract two people come and they work for two three four years and they go start their own venture fund or whatever muscle top that's great um but what i told them was you know just find the great companies and i looked at investment team meetings usually 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 two to four pm uh 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 i.t 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 um are you enjoying the lp fundraising i am now yeah i am i'm kind of like uh remember an 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 and so you've talked about this now you're you're now you were in kind of this one bucket with your capital and you're like i'm gonna go raise money and i'm like and now you're going simultaneously in two directions of you want the public and you want the big institutions right we'll see um i've had select institutions make small bets the first one was 10 the next one was 11 and then the last one was 44 million the first one i deployed in five years second fund two years the third fund two and five years i was just that was my first fund it was you know me bill girley dave goldberg rest in peace tony shea rest in peace david sacks chamath just a bunch of my friends put money in and 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 i literally did two webinars a couple 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 uh publicly right yeah you didn't raise publicly no i thought about it but for a whole bunch of reasons 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 mack the dc yeah you did a great episode with yeah it was great i had him on uh i had like you know first time founders for a season of angel um which is like a subsection of the this week in service podcast and i became an lp in his fund and he just told 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 uh 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 well 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 angel let's just set it up and then you just start talking to other vcs you talk to them and you just you just have to be willing to take 50 meetings a week and 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 what this is it's not that it's easy but on the internet too you find your people who believe that with you and then they believe in you and then they back you and that's the correct correct and so the whole thing but what i noted when i was taking my notes watching him was so much of the time i was like oh my god i'm not gonna do this i'm not gonna do this i'm not gonna 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 right now i'll put that right there in the place where i keep everyone who tells me yeah three years from now what to do yeah and so you know um i mentioned it on all in i tweeted it and all of a sudden you know i had a thousand people sign up is there a limit to the number of lps you're gonna have of course yeah it's 250 accredited up to 10 million and then 2 000 qps and so it's it's a lot more work and qps not for me not for you but not for me to catch qualified purchasers people look at you playing jason i know you know what a qp is i just want to dish the ball i think it's five million in investable assets like uh and then uh 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 in net worth 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 year 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 i mean now as a participant of a fund on angel list like these are like those are big numbers like you do something consistently for spps on angel list and we have the fun too but like you know yeah you're hurting cats you need to have a lot of people um 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 uh 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 um it's high risk it's high reward i'm in 20 venture funds myself including yours thank you um and i'm sure but don't but don't pitch jason i'm sure i will do yours no i mean i i'm just going to pick them based on people i know or people i know online or pod and yeah i'll do one or two new ones a year and um well this is kind conversation earlier, like on the internet, this is the democratizing thing. Nobody's going to just give you, if you just, you know, nobody's going to just invest in your fund, but if you go do stuff and then people are like, oh, Jason does stuff. Great. I'm going to back Jason. Ben does stuff. Be of action. Yeah. And it doesn't mean you have to start a podcast. 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. 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? 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 I would be meaningful for me. Both my parents are cancer survivors to have Memorial Sloan Kettering's endowment or an endowment. UCSF or something like that. 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. And I, you know, I got that from Sequoia, like, you know, you, 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. Click, click. Here's what Ford Foundation's doing. Here's what this foundation's doing. And you're just like. They have their conference rooms are named after their LPs. And the conferences are famously named after them. It's like. And this is real. Powerful. Like I, I find we have like state pension funds. And stuff like that. That'll make you get. In PSL Ventures. And like, you take it much more seriously. You're like, I am, it's cause it's not just about the reward. It's not like, oh, I, I'm so excited about what we're gonna do for them. It's like, this is really important to preserve and not grow, but like preserve this capital. Yeah. Yeah. 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. That was. That was like one of the seasons of that of billions was he's like, I'm gonna be a family office. No, I'm gonna 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 I, he, I, he seemed to perceive like. I think he felt that he wasn't a somebody in his ecosystem and his community without managing outside capital. I think it's like playing, you know, in the bubble with nobody in the stands versus getting on the court. Yes. Like Madison square. It's like, and there's people in the stands, your returns, your numbers don't mean anything unless you're putting them up for. Dude, I'm doing this public where I should say quasi public people that still have to sign up to, you know, come to a webinar. Um, 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. Um, so, you know, I'm kind of enjoying it. Um, 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, but it's always been like solo GP is a blocker, no track record. Your fund is so small. Small fund. Small fund. We're a $50 billion endowment. Yeah. And you know, like, you know, um, 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 now- Was that in the last fund cycle? That was in the third fund cycle. Yeah. So now- 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. 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 going to do five webinars this fall and then I'm going to go on the road and start meeting with folks. Are there any downsides to doing the raising in public thing other than- Not that I can see. I guess you could fail in public to fail to raise the fund. That doesn't seem like something you're scared of. The freeing thing 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." Right. But then you're raising capital every single time you're making an investment. Yeah. And I'm getting deal by deal carry. And I have 100% 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?" And I don't have to have a fund. I don't have to do audits. I don't have to do any work. Literally, 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. On the one hand, I could do what you just said and do very little work, but have it all be pure. On the other, I could go do what you are actually doing and raise, have LPs, be accountable. Yeah. How did you, how did you weigh these two? 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 don't mean to be obnoxious about this. I know it probably sounds that way. But for a kid who's, you know, going to be a cop to be where I am. Yeah. And this is why I 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. We were talking about the legendary… That's the rush. …Twist episode 180 with you and Travis. Yes. Like, man. I mean, that was… That's the secret before the show stuff, David. Yeah, that is the secret. But from the juicy before the show… No, I mean, I'll talk about… I can talk about Travis. Yeah. Yeah. But that was like, you know, you know, Urbu was such a baby company back then and like, you know… Crazy. One city. One city. I mean, I invested and I had an open angel for them where Cyan Bannister and Chris Fralick, from First Run, you know, invested in the company. I think they both met them there. Sokka 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 going to kick him out because he was at this co-working space called Dogpatch Labs. Dogpatch Labs. I worked there too. Yeah. I worked at CoTweet. Yeah. So he was… Oh, CoTweet. I know that. Yeah. So he's sitting over there building bourbon. Yep. And… That's right. And Sokka's 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 just…" Wait. This Open Angel Forum was at Dogpatch Labs? Here on the pier. No way. Oh, okay. I think that pier then they shut down because it was going to collapse. Condemned. Yeah. Condemned. So that was there. And… Naval also did a bunch of like events there for Angel Hacks. I… at the time, Naval and I were very friendly. Not friendly now, but not… we don't hang out or… 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 going to do this thing AngelList." I'm like, "Well, I'm doing this 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 Assure Fund Management, which I wound up investing in. Did you buy that? 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, 5,000. I mean, they've done a ton of them. Seriously great group over there. And so he taught me how to do Syndicates. And the first one I did was Calm at $4 or $5 million. That's nuts. It's funny. I was looking for your… Like, literally, like, winning a championship the first time you step on the court. 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, but still a good Uber multiple. But you've looked at it. If you look at Calm, you just… I looked at David, and I was like, he sharpshooted that one. He did. That one I could be even more proud of because… I'll tell you why. I mean, it was, like, ridiculously early and, like, a super low basis. They had… it was $4 million. We put $370,000 AK and owned 6%. And they didn't raise any money until it was a $250 million valuation. So no dilution. Wow. And… Sharpshooter. Sharpshooter. And… It's like Vanto. Vanto is 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 and giving him his flowers. And he said, "You know, 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. What? "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 and they found product market fit while burning through your money i think so i think so because you're like take more of my money no no but i mean if you think about that as like a that is not the case with uber or robin hood i was along for the ride let's be honest uh i did not change the trajectory but like but for jason calacanis calm 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 that's like real angel investing like there's there's a lot of like individuals participating in venture rounds and like yeah no offense oh hey i don't take any offense so like call that angel investing but like coming in when the company could die needs 100k 200k 300k to get it to the stage where they revenue to date i think when i like ever yeah because they were selling the app for ten dollars because remember at the early stages there was no subscription model right in the app store you just sold an app for ten dollars a person had it for life so the business model of apps was make a lighter for a dollar then make lighter two yeah and charge three dollars 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 hell up and you buy angry birds and you buy angry birds two angry birds three and you know it was a really weird time and then they're like yeah we're doing so they told me like you know um because you know i was under nda as well and you know hey subscriptions are coming that's going to change everything and they were going to do ten dollars 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 what's the suggested donation it's like twenty dollars you know i said you want to charge ten dollars a year it's twenty dollars a month how often do you have to do this to visit yeah i 20 hours a visit i said how often do you have to do this if 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 eighty dollars a month to go and we're charging ten dollars a year so that's like a thousand dollars a year versus ten dollars what if it was ten dollars 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 gonna do that and it was then they went to ten dollars a month or whatever and they didn't wind up at sixty dollars a year whatever it was but we got money printing machine pretty quickly 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 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 of course than my normal investment absolutely really 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 what do you think it was like what what was when you look back and you're like factors nine nine okay all right yeah well angel angel that university no i don't even teach an angel at university but oh um i i'm training my team when they're meeting with those 60 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 15 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 so 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 10 so if you were to look at something like com or robin hood okay they're the best looking app with the best ux of all of anybody in the category right so com was better than headspace robin who was better than e-trade i mean it just doesn't take our rocket science 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'm 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 yeah 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 with product page 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 so let's if we're gonna say world-class like a world-class performance is different than a serviceable form it's world-class cinematography world-class script world-class dialogue that's different and that's and then product velocity 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 i'll get on the phone with this guy and we'll walk you through it here's what we're debating about on sunday we're reprioritizing a month later they play and then check check check and then you go like if we're with ro with superhuman and i was an investor in his company before that report of ro like the changelog at superhuman superhuman that people don't realize like 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 so here's an interesting question we should ask rahul this we've had him on the show three times now product genius 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 outlook support you just don't you know when you hit command k yeah you probably know 50 of the features right like do you use remind me of this i do okay great do you use labels do you do snippets i do okay yeah which it was all there when i started using it for three four years ago i think a lot of those things have gotten better and better yeah so it's just that like polish polish polish polish polish um i really like want them to make snippets multiplayer i want to share my snippets oh yeah oh with your team yeah i love it yeah so i want all of david's pass emails they're so nice i don't know like you do it on the phone no no i just don't do anything i don't i don't email anybody you know when you pass i actually do have pass emails from i've been literally creating a collection of how to pass with my team and i'm standardizing that 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 the company if i'm not going to invest no but you must say hey we are not going to invest you've took a pitch oh no i i get it i don't i don't i don't you basically don't take a pitch unless you're going to invest it's the weirdest thing oh that's very weird so you do all your work up front you front load it the deck everything we're in this unique position as you are too but um with acquired we're like you know we have every six months we have six companies that we work with on the show right as our sponsors and our partners and we get to know them really well in treasury and i'm now an investor in just about all of those companies so it's not like uh it's growth stage investing yes it's like later they're clearly the winner yeah they're not yet priced as if they're the winner most of them yeah yeah exactly they're gonna just keep compounding yeah good luck yeah pricing's gonna be hard well we'll see we'll see on entry price we'll see yeah i don't know what's gonna happen to these companies after you know the flat is the new up but i think you know 50 haircut is the new flat well public comps got hit 50 plus percent yeah i mean this week they got hit harder again yeah i mean i'm buying equities right now i've been doing it jtrading.com and um i am going to buy more sorry about all my picks a couple weeks ago which one whatever i thought oh yeah yeah no no i actually love taiwan semiconductor uh no i didn't know this was the other one i think no no no i didn't know twilio twilio was yours and i love that one too and i i like shopify as a pick um i'm actually really enjoying it it's really not investing balancing out not investment advice but it's balancing out my um 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 a blaster no i'm a jedi i use a lightsaber but you know but if you learn if you use a blast very fast it's not as elegant it's helpful it's really helpful if you look at the very best people the best gps like hold on in venture over the past two decades sure they all trade public stocks yes and they do it for the same reason they're going to fight with the saber yeah but like they want to know how to also use a blast or how to fight in an x-wing or something like it's not what a jedi does but jedi will do it it also keeps you really sensitive to the public cycles so that like yes it's not that you have to think about the public comps when you're investing but you have to be aware of how much those will change yeah 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 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 board's decisions the board has to make of a public company versus the board of a private company yeah so it you know i'd like to join a public board at some point it 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 um yeah especially given the market right now i'm gonna be careful but you could you could also invite me to do that but it's just it's been especially through the show now you have relationships with public company founders sure of course yeah i mean if i really wanted to i'm sure i could lobby oh you don't have to be on the board though you can have a great relationship doing the analysis and i'm doing it anyway with molly every day okay you know twilio's or adobe's come i just bought adobe this week when they bought figs so funny so did i not investment advice not investment advice but i was like they bought figs okay so here's my theory on this they bought figment 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 innovate in 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 be able to do that they were not going to be able to do that they were not going to be able to do that they were not going to build the next figma like that would be a full rewrite of their entire software stack yeah so buying the thing even though they paid a tremendous premium because 50x revenue multiple because of the network effects that figma has um 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 and they're not going to be able to do that because they're not going to stay on board yes they're taking a youtube approach i think everybody in m a now knows now yeah like whatsapp 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 of figma creating photoshop i'd be happy to do that but i don't think that's going to be a big deal for adobe if fig they didn't buy figma 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 yeah you just discounted the right move fantastic it would be like people are like oh you know the warriors signed kevin durant um and you know what we're gonna lower the biggest odds but they paid a lot to get them on the team so yeah and oh you know okay i'll buy court side 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 totally different thing but yeah and they have a free canva already and you know what if there's always a the internal people who are penciling out that spreadsheet yep 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 pay for it so right now adobe has a bunch of designers paying right right but they may not have all the non-designers right only designers pay adobe right well no they have marketing cloud but that's a totally different yeah yeah 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 plus they got the whole creator class 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 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 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? It's more defendable. 100%. Like the virality of it. I think Saks made this point on all in two weeks ago, which was like, if they're paying 50 X now and the company's growing, okay, they're paying 20 X next year, 25 X, who cares? Right. It's such a high growth company. And then I was just thinking, well, somebody's got a theory there. And when I sold web logs to AOL, people were like, Oh my God, these people are idiots. They gave $30 million to, you know, for web logs, Inc. They've only got 200 K 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 thousand pages. Yes. 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 and a half million people would flow through. And then they would put those ads on our sites. And then they would blow out 50 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 $500 per piece of content, $3,000 per piece of content on AOL.com. Slash autos, whatever. And we were doing it for, at the time, five bucks a blog, $5 a blog post. Cause we said, well, people can write for an hour. So it's 20 bucks an hour and it's $6 minimum wage. It made sense. God, 50 years ago. The internet media game has changed so much. And then I was like, you guys are doing 200 K annual revenue. We had done 200 K to date. Holy. Over the 18 months. What is it? I mean, now like the world we're in today. People looked at the multiple and they were like, Jay Cowell just robbed AOL. And I was like, okay, $30 million. But now I look like, what do you, what do you think? Like, here's a, I look like an idiot five years later. And that's the best, the best M and a is when you look like you robbed the bank. Yeah. And then five years later, it looks like you robbed the founder. YouTube, Instagram, Figma will be in this category. Like, yeah. When they bought Instagram, they're like 30 people work at this company and they gave them a billion dollars. You guys are morons. And now it's a hundred. Here's a thought exercise question. Obviously irrelevant because you don't monetize it. Yeah. So what do you think the enterprise value of all in is? Well, it would do $10 million in, 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. I mean, 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. Well, but, but you do get a huge economic value out of it. Pull me aside at some point. It was like, Hey, Schmuck, like just we're friends. Like you're all, your next fund won't be, be bigger. Hey, dumbass. And I was like, you know, when you have a friend who can be like, Hey, dumbass. Yeah. Like that's a good friend. So I appreciate Schmuck 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. 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, you guys just started doing that. Freedberg just talked about his SPAC. You know, Freedberg still has a SPAC. Yeah, he did. He just found a target for it. And Schmuck talked about the healthcare company. The healthcare company, which is, I mean, we wanted to talk about that because Schmuck 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 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. Right. So, you know, I'm kind of bummed that, you know, Freedberg'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. Doing another one. 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. Well, code conference is done. So like there's a vacuum. Code conference is done. Yeah. They need a new host. That's crazy. Like it's such a value. 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, this is incredible. And so I think, you know, Kara Swisher, like moving on, but Jim said he's going to keep doing it. 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, which you're definitely on. I am. You think? How could you not be on? I mean, I'm not, I'm not even saying that to like, make you feel like, no, I'm joking. I'm being a little bit facetious. Okay. Okay. You're joking about being humble. If it had that kind of press, it seems like friedberg would want to do it it seemed more like the thing he was averse to is the like yeah i mean whatever the issue is like we've had our issues um we've all have issues um but um i think the there's basically two possibilities for all in summit um i'm going to present it to the boys uh 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 uh 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 um and the fans can decide if they want to come or not and partially in partially in exactly so you know it's up to the boys um they want to do it but it was like a pretty great success you already have colin so yeah well yeah and i i started doing um i started doing a colin show called after all in for the last two episodes where i took calls about the last episode of all just to support david because i don't think people remember how great that app is and it's really made great progress so i want to be supportive of him and i have a small investment in it do you um very meaningful but on the one hand this is ridiculous on the other hand it might be ridiculously low it's worth 50 million to answer your question 50 to 100 million i mean as a top 40 podcast it's worth at least 50 million on its own though but i mean like economic value that the four of you oh who knows like 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 right possibly 10 you know like so yeah that's the thing like i think like man weblogs like you were doing 200k of revenue you sold it for 30 million pretty great takeaway yeah and now look at this like you know yeah i mean listen i hope it keeps going i hope we can keep it on track and um you know i i love doing pods this week in startups is a great way to keep it going and i think it's going to be a great way to keep it going as well you know yeah that one's out for 10 years and all in is what is that like a quarter million listeners or something yeah some of 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 um 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 right and that's what we talk about i want to think about with ourselves i want founders and capital allocators to listen to it and i'm not trying to move up the rankings i don't want to 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 fifteen right with you guys in the rankings it's like that's where we belong look i got number one on four to six but who's counting whatever you know like 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 right if you go to this is the beauty of this guy who reads bible passages and he's huge it's like if you can literally true crime true crime religion read the bible or ben shapiro dunking on libs the end that's like that's how you do it or do it daily but joe rogan's out right he's on spotify right right you know he's not in the other rankings so i mean we'll 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 would be a fun acquired episode is uh howard stern i feel like it's underappreciated how much i copied my that's the playbook that should be the next taylor swift type episode that we do yeah no for sure he wrote the playbook i literally took notes for it king of all media do you know him i have never met him i'd 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 interview great interview great interview where he really refined his technique i really appreciate that about him and he created characters sound familiar yep branded them yep he showcased them the whack pack you know all this stuff did he ever do a event he used to do live events he did the u.s open sores 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 right 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 a live event and he did a live event he did his books uh which were phenomenal he did a movie 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 so i'm literally gonna do are you really yeah i mean just you or the besties or no just me um the 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 that's a lot more work though well you know we would have to do it weekly you know there'd be some format some shiny floor whatever it's 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 um oh wow 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 bernard had reached out early on when it was dragon's den um right before when they were going to bring it here so when it was dragon's den 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 because all that was doing so well 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 yeah so they would founders and companies be open to that yeah so the nbc show i had done the pilot for which never made it on air um uh what was really good was really about you know me incubating companies and uh they spent like four or five hundred thousand dollars doing the pilot it was really good and it would have been a big hit did did it get canceled because of the heart wow so they were just like anything that was in his company and all the ip is dead because he's a monster and so anything associated with it but you got to remember he did project runway so he had done some of these giant shows people don't know that about that and so that's i forgot uh yeah that had the twc at the beginning exactly so you know i just nbc you know i nbc bought the show in the room loved it and did the pilot and it came close and chamath was on that episode actually he did the pilot oh my god he was like my vc friend who came in and it was my vc friend it's no it's hilarious um 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 i'll be gone soon well you know it's you never know and uh yeah well you've been to your friends yeah i have two friends who died young and i'm just like i you know i 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 well so like you're probably at a point now where like literally not in the top 10 what is more money gonna do like you know you don't want to understand my life like it is ridiculous and charmed like i can do whatever i want i have enough money to do my kids are fine i can have whatever i want i don't care about like a third home like it's 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 i'm good like 100 i literally do not care about do you feel like that's a demon that you fight is like no any allure toward 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 recognize 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 what 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 and it's like okay you know here's doug leone and moritz and you know uh here's you know really john door here's girly like if we are making them out rushmore you want to be on that with them i would like to make it there or at least be in the conversations all right listeners now is a great time to talk about one of our favorite companies statsig yes there is a reason why the best product teams rely on statsig whether they are iterating on their core product features or shipping ai powered experiences at scale 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 this is where statsig comes in it brings experimentation feature flags analytics into one unified system so teams can ship safely test rigorously and directly link what they changed to how users actually behaved 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 slash acquired to get started when you guys are having the conversation in 20 years and i'm gone or i'm retired and you're saying mount rushmore imagine you retiring yeah i think it's possible um i met don valentine when they were like you know he was not active investing 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 um yeah like why retire um he was just awesome oh um but you know if you had that conversation right now about mount rushmore like you gotta okay so who's on your mount rushmore well i mean you gotta have don valentine yeah right that's just not possible but how are you scoping it because you probably need paul graham too 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 yeah big impact so paul graham's definitely running but okay so do you go with john doors in there along with so if you're doing firms it's a lot because you get kosla door and um perkins tom perkins you get the three of them at once yeah you do sequoia you know which people forget venera kosla spent a decade at klein and perkins with john door like 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 leone uh mike and valentine rule off well we'll have to get it back next time we'll have to get it back next time but you put all of them they're active all the same time 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 we just did benchmark you gotta have the fab four era of the fab four era of benchmark was truly something special yeah it's kind of like it kind of builds itself the mount rushmore right now right it's 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 yeah like is it well it just depends how wide we're willing to scope it is it like traditional series a type venture firms or is it angelus naval right that's had a huge impact do you put yc in there do you put yc or techstars both have a huge impact do you put um you know uh who else could be in there that's just you can argue for founders fun you can say yc and techstars not yet the founders completely different things on the way like what yc is like yeah for sure i mean three orders of magnitude for sure they've done the same number of companies i think but just in terms of yes but techstars i think was a little before white combinator but anyway you you definitely white combinators you know and running for that fourth spot i guess and then who else would you put in there masa well no i mean but maybe maybe i don't know depending on excel would be in the running for sure it's ron conway 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 successful generational transitions where each of the generations would have been on mount rushmore 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 yeah oh yeah just the hall of fame yeah and the hall of fame has let's just say oh dude we should open the venture capital hall of fame capital allocator hall of fame top 25 i was trying to figure out when we were doing the benchmark episode research which will be out by the time this comes out yeah uh 2480 sandhill road is a very special building it was the forethought powerpoint the quadris complex quadris complex yeah office then it was microsoft silicon valley this is the internet right now this is the internet it's like wow we've aggregated all the other people everybody else who cares about this is listening right now yeah it's like and like sebastian who wrote the parallels yeah yeah yeah you guys are taking this way too seriously it's not that important but then we're like alone tvi meryl pickard tvi that's a good uh august capital benchmark capital shasta capital all in this 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 whole thing venture capital fame is something we should go right on we should just do it that would be pretty fuck it we'll just do it like yeah yeah 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 yeah yeah yeah this year we're in the building we're conducting we should totally do this can ohio exists hilarious you know cooperstown there is a um what do you call it there it'd be our cooperstown yeah there is a computer history museum but it's not for the pc which is totally valid but it's not for capital allocators it's not for people like yeah there should be a hall of fame and do we like do we midas list style ask people for the real hard truth no no no it's about impact you know we decide the three of us we decide it has to be impact on the game does the nbca have like a lifetime of impact on the game achievement award is that the closest thing it doesn't really exist anymore yeah no it's it's about impact legacy like the intent of the person right this is why like paul graham would be like you know uh first ballot this is why yeah you know okay who are the first ballot entrance so obvious we've already talked about it those are all first ballot do we have anybody who we haven't talked about or who's not obvious but would be a first ballot you can't 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 yeah it's just like the sports hall of fame so you gotta have a yeah you gotta be you're not playing in the league anymore so paul graham's still playing in the league does jeff bezos count like wow i mean how many investments has he made that google investment is crazy 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 oh they're not separate companies but like yes capital allocating lowercase c lowercase a they've been great at placing bets yeah but you're right jeff bezos is probably the most successful angel of all time yeah i mean if you just did it on dollar yeah you know when you when you're looking at it i think you gotta look at impact like impact on the game legacy like so he's carmelo anthony hall of fame of course he is but he didn't win a ring but you know he just he's carmelo anthony right like or charles barkley didn't win a ring but okay so then we got like arthur rock like you gotta look at like the founding father type of course of course yeah there's no doubt i mean that's like going back to bob koozie or whatever they're 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 then you have the people before the league you have people in the league yeah you can generational shit right here you know patrick ewing yep you know because i think like you look at girly like he's part of that patrick ewing generation right like that him elijah on charles barkley generation yeah you start talking about founders fund or yc or angel list like okay now you're talking about more modern era yeah still going modern era after 2000 but if you started before 2000 it's a different group do you notice we haven't talked about entries in harlott's in this conversation oh god who cares no impact on the game they're in they're in both of them are in for sure no doubt first ballot they totally are i guess impact on the game totally changed i mean i just feel like it's gratuitous it's just like raising 10 billion dollars 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 well i do think they have interesting ambitions though i think this like that's the problem it's more ambition yeah it's more ambition than soulful but there should be a jp more goldman sachs of silicon valley and there'll be for sure i don't know yeah why is it why does goldman sachs manage the money of entrepreneurs 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 craft it's i mean it's like the literal antithesis of it's an industrialization it's the intent 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 well i mean it'll be mean reversion because like when you get the law of large numbers you have mean reversion 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 not fair that was the 2015 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 arc it will not be comparable to benchmark at sequoia and we i mean made a lot of hay of the fact that they had uh that they made 11 billion dollars in profit on coinbase and like right which is i do not think they sold out of that no they so they did not make 11 billion dollars yeah fair enough as fair enough well i mean it's timing is everything we'll see i mean it's interesting too i mean having just done this benchmark episode like the benchmark fund seven one of if not the best institutional size fund of all time just like unreal 20 to 25 that's like the the 500 fluctuation in the marks on that fund and it'll probably be probably end up between 15 and 25 x maybe but like but it fluctuates up up and down so much of course i mean it's we live in a very volatile time right yeah so yeah i like the hall of fame idea it's kind of interesting i think we actually would be a fun thing we should get some space on sandhill and put up no i just we could just do it as like a dinner we just literally have we don't need every year we get a yeah we get our we could just start in a restaurant but you could get like a little hall yeah 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 and i think like you we could do like the three who we would hope would be there and then we'll have we do it like the sports where you have the person who's being inducted chooses who inducts them sure which oh that's fun yeah so ruloff does doug yeah whoever does moritz yeah yeah but john parker does moritz - Mike chooses who, you know. - Yeah, go ahead, you can have Larry. jason calacanis come up and be like larry and sergey yeah yeah obviously totally yeah uh john door would uh ask bezos i mean it's killer it's a killer idea i mean we just do bezos yep doug and mike yep and then who indexed you do one in memoriam yes you would do one in memoriam you know whatever yes because it would be anticlimactic if the only person because we will induct on first and if the only person that we inducted that year wasn't a living person who could attend yeah you do a combo you do a combo maybe it's four people a year you know 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 in order for this to like feel good i think you're right that it has to be about impact not about returns no returns is like so that would be like saying it's like albums sold for the rock and roll full of fame right there are people that'd be a very andreason horowitz way to do it as well yeah injuries but oh what's the total assets under management you know and it's like okay dude we get it yeah nickelback sold a lot of albums yeah they're the nickelback event no i didn't mean that you said it i wasn't talking about it oh god oh god oh god now they've sold tons of albums right i'm not saying that they're a million no but there's like oh boy 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 andreason 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 a hundred people stood up and my mind was like oh whoa angel investing's cool i mean i wasn't an angel investor at the time i was you know long before i became a scout but that i always remember that moment when like a hundred that like inspired partially inspired the scout program is that what gave you the is that what like put you in business as an angel the scout is what put me in business yeah what happened was i had was your uber investment you personally or was that sequoias that was sequoias okay 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 you know at the time they carry 50 50 at the time yeah they dropped it down after that yeah i bet it's like every time i'd see doug leone he's like 50 and they had 30 percent carry at sequoia at that point i think yes i mean if i were you i'd be like 50 carry to them i can't believe it no no no doug and always this they're so classy doug always made a joke would always make a joke was like 50 carry oh god we get 30 you get 50 this is funny we get 30 we get a lot we're 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 on behalf 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 look at elon 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 they're not going to say here's some fuel you know here go fight that war you know it's fuel and it's belief too i mean like what you're telling your story about com yeah is not uncommon i think amongst oh my god i mean look at i mean the stories uh about don valentine and atari and other places where he was at cisco it's like so we got to get this thing back on the rails this thing's going to zero yeah you know like there's a lot of existential moments where things go to zero and like so can i ask you as we start to like wind down drift toward the end of the episode here that's your line that's your favorite line drift that's that's the ben signature line here toward the end of the time together like is this different enough from our normal show should we do this what should we change yeah do you like this i think a casual glass of wine and just you know uh if you have friends of the pod and you want to go deep and talk about them in 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 your profile somebody like i forgot that i had you had done like the first episode with me and uh 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 yeah so i think it's a different our audience was i like this i like this format well part of what we you know like lex has done so great with his show yeah 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 yeah no his is intellectual i don't know why he's in the tech but i like the format and like kevin rose used to do with the foundation series and like yeah i mean long-form interviews like howard i mean i think joe rogan stole it from howard yeah 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 yeah so lex is clearly inspired by joe and joe was on joe was in the running to replace jackie martling on the howard stern show people don't know this so really he was very enamored with stern and uh he wanted to be stern i think and he eventually has supplanted yeah in a way he did become yeah it did become stern and so good on him yeah right down to the you know serious spotify like right down to it he became doing a platform yeah doing a platform which is what stern did stern had multiple platform deals he did syndication first then he did the serious xm one because it was a new platform and he built the plot he used his number one show to build their platform right which is i think it's a great show and i think it's a great show and i think it's a great show and i think what uh yeah which this but actually 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 culture business anybody in new york because new york everybody in new york was pretty fucking interesting so yeah 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 was just 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 yeah you know it was like a little like sort of more jazzy you know a little bit more like acoustic so i like this format for you guys do you listen to smart list at all do you know about that show i i have listened to one or two episodes it's bateman will arnett arnett and then somebody else yeah the guy from uh will and grace sean i don't know who that person is but they bring on a surprise guest each time and and the other people don't know yes so they're not prepared yes and it's like it's like it's like katie perry it's like chris pratt yeah it's become a big deal i kind of want to do that of tech but like wait you and i don't know who the one of us is bringing somebody you guys are not good you can't make you got to know the person's background much better but the celebrities carry a certain charisma with them that our industry doesn't have yeah but maybe it doesn't have to be a surprise as much as like well that the other thing is that it's even though they have guests the show is actually about them the guest is a prop 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 because i see it on itunes i don't think so it's really weird that like spotify doesn't allow joe rogan and call her daddy on itunes because the advertising would be huge right right so why not like there's some nba that's around the numbers that says it's more valuable if it's driving new subscribers i guess that's it i guess that's it yeah oh guess you know what they want to be able to have those new subscribers so when they go renegotiate with the yeah music i saw they're doing audiobooks too now that's the next piece yeah that is the next piece yeah they're doing audiobooks one-off purchases smart i mean audio is great all right it's getting really hot in here it's getting so hot for those of you who know we're in like a sauna a new yeah david's new house david just moved david's got a new house empty house we there's no way it's sort of like the shining there's no furniture we just literally this is all from craigslist all of it literally in the last like two days explains the smell that all right you could i mean listen you're rich dude just go on oh my god we can't all be jason calicatus oh you're no come on man i know those fees oh my god i love craigslist i love craigslist i love it you buy used furniture on craigslist all the time i do not buy new furniture it's gonna stop i bought a temporary couch on craigslist it's the thrill of the it was not no you're gonna get robbed don't do it it's too crazy craig newmark i love you but all right with that with that our thank you to vanta oh vanta.com slash acquired vanta.com slash acquired uh our thank you also you don't know who the other sponsors are because we haven't we don't have 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 i love reading that are you kidding me do you want to read our brex ad they don't sponsor my pod so no maybe they have i don't know there's also a lot of ad brex yeah i know a lot of people who use brex i think we use brex it is one of my companies if you're enterprise if you're global by far the best corporate spend management it's much more than a card now yeah for expenses and everything like that right and then they've kind of expanded behind that so you can give cars to each of your employees and then if they screw up you can turn it off or something yes exactly if they jump pre-approve some budgets yeah you don't want people jumping the fence and going crazy all the listeners know because they they heard it like an hour ago they're very familiar oh so anyway thanks shout out brex so that's brex shout out brex and then use the promo code twist we share this uh last sponsor these are these are great folks these are these are like dear friends and and geniuses and raconteurs masterworks no no no good guess think think smaller but bigger literally small but secretly huge tiny oh tiny of course yes they're buying companies they're buying companies they're doing a good job yes they're creating like the berkshire of of the internet the internet and can you imagine a better time to get the monkey off your back of venture capital and sell your company let's secure the bag that's my favorite takeout line 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 that aol weblog oh man let me tell you something i i'll tell you the story what did you do when you secured the bag i'll tell you what happened i i got this a funny story i'm in my office you 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 5 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 yeah on the thing this is 2006 five is six yeah i'm hitting refresh i'm hitting refresh and then bing bing bing bing bing you know all the numbers come in to the for the whole you know amount and you own most of weblogs uh brian and i were equal partners then we had peter rojas had some ownership and then mark cuban was our big investor uh and by big investor put 300k in for five percent so that was a great outcome for him uh oh wow yeah uh or more maybe on ten percent i think on ten percent 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 you're like this is a new experience i've never had this before 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 because i spent my whole life worrying about money yeah you know my dad had lost the business everything 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 and it's a tiny bag but it's filled with diamonds and cash and you just open it up and say thank you tiny thank you tiny for securing the bag acquire.fm slash tiny no it's literally they don't give us a thing oh we don't know that's right uh is it high at tiny uh and tell them whatever it is like just know that tiny tell them that ben david and jason you can mention jason yeah but i did buy a one touch espresso machine i bought a jora one touch espresso machine i bought a jora one touch espresso machine which at the time was like two grand and i was like this is unbelievable that's the that i tried to buy a ferrari oh they wouldn't sell it to me in beverly hills you were like no new money or something what's yeah basically i went in there and they're like oh yeah what are 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 from 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 you don't know this is actually no this is part of their strategy it's part of the strategy part of the strategy is they have the ferrari's but they don't sell the ferrari's to build we're not putting anybody to list i was like well how long is the waitlist he's like don't even bother getting on it i was like okay i was like i'm a cash buyer he's like everybody's a cash buyer i'm like okay um uh can i ask you a question then he's like sure come into my office with like espresso you want some pellegrino i'm saying i'm good and you want some people who offer me pellegrino espresso and i was like i have the same one touch jura and it's like italian guys 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 for more 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 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 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. and i was like you're like the sticker says no no no this is a potential use i said the used one i was looking at he's like you can't get these cars and i was like 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 said 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 the car and i'm just perplexed that would bother me all right well let me think about it i left and 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 f30 and then turn the page it was corvette c6 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 or something like that and i was like let's go to the court 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 on the 405 and we're driving the corvette and he's like this is a corvette son like you're going 70 miles an hour 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 100 miles per hour the guy's like yeah how does that feel i'm like great 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 65 grand it's like 70 and i got five grand and it's american baby and it's american and uh that was the car that i famously uh was according to gawker robert scoble myself and elon when elon got the first p1 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 uh you were racing we were driving them along sunset boulevard 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 just gonna beat everything and this was the first one that you know first yeah that was amazing the prototype that's in space right now it's the cherry red one that's the one that's the one that's the famous photo of me and elon in front of the corvette uh with that 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 just before the iphone you realize like robert scrobb was recording this on his nokia you know yeah these are the memories right like crazy the journey that you've been on yeah it's pretty this is the stuff you just will cherish forever my life is unbelievable i am so grateful for it and uh thanks for having me on the podcast listeners thank you so much acquire.fm slash slack come join us we'd love your feedback this is cool this is a new shtick yeah acquire.fm store you can buy cool shirts uh slash jobs find your next career experience craigslist you can get a bunch of new ones that's right acquire.fm slash david buys you some smelly furniture my god it is hot in here all right we got it let's go eat some food let's have some sushi or mexican i don't know what we're going for here oh so fun thank you so much of course 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 acquired.fm at gmail.com or tweet at us at acquired.fm and uh with that listeners we'll see you next time we'll see you next time