Acquired - ACQ Sessions- Jason Calacanis

0:09So wait, it was a magazine magazine. Yeah, I started yeah magazines were it's like the original platform for yeah, we started Silicon Valley. I guess this is the trick. We've just been reading all that stuff that you said beforehand that like is really juicy. I don't think we should put that. No, definitely not definitely not. We don't want to tell people where the bodies are buried. Well, cheers boys. Cheers. Here we go. Where this is the is this the first one or this is the first in real life, but I think this is our 9th, 10th together, something like that. A lot. Between the two pods, yeah, for sure. Great to know you, boys. This is the first acquired sessions. Acquired sessions. I feel like I should get out on 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 episodes. You know, it's awesome. But really for folks like you who we know really well, what happens if we...

1:06Throw out the script. And just chop it up. And we just chop it up. David Rosenthal unplugged. Wow. Literally MTV unplugged. Literally. All right, listeners. Now is a great time to talk about a new partner of ours here on Acquired, LaGora, the agentic operating system that is redefining how the world's best legal teams work.

1:28Yup, it's sort of obvious that AI is going to completely change the legal industry. I bet most of you listening have dropped a contract into some sort of AI chatbot out there. LaGora took that insight and asked the question, what if you really built something with that power from the ground up for the legal industry? So the founders did exactly what great founders do, operate with obsessive customer focus. They embedded inside a massive law firm.

1:54for months. They sat with the lawyers just watching how the work really gets done. And that's how you get features that customers love, like tabular review, where you drop in a folder of hundreds of contracts and it pulls every key term into a grid a lawyer can actually work with. Legora's bed here is interesting. Since it lets each lawyer handle more complexity, any given person can increase the quality of their work and do higher value work. And this means that the pie can grow even as each individual task takes less time.

2:24And they recently launched LaGora agent offering greater intelligence and performance. The agent lets lawyers set an objective. Then it can handle the planning and the execution and delivery of the final product. Legal teams get to maintain full control and transparency since they're still involved where judgment is required. And LaGora works where you already work. You can use it within Microsoft Word while redlining or drafting. The early LaGora numbers essentially speak for themselves when they have a head-to-head pilot with their top competitor they win 70% of the time LaGora now has over a hundred thousand lawyers on the platform from 1200 legal teams in 50 countries and crazily they went from one million to a hundred million in ARR in about 18 months truly insane numbers and that is the real test

3:16Plenty of things demo well, but the question is whether a busy associate actually reaches for it during crunch time, or whether a partner trusts it before going into a conversation with a major client. If your legal team wants to check it out, whether you're a law firm or you're in house at a company, you can learn more at logora.com slash acquired and just tell them that Ben and David sent you. So in the juicy stuff earlier, you met Tom Hollow.

3:40Yeah. Is that why you started? Can we just keep her personal like referring to the juicy stuff at the same thing? Yeah, the juicy stuff. Yeah, no one's gonna do 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...

4:09behind, and the Fed showed up one day, and this was 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, a state liquor authority, they kind of take it serious. So Fedscom, shotguns, the whole thing, they seize the place, they seize everything in it. And I was like, wow.

4:37I 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 rack, and the HP had just come out. Would 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.

5:03So, I decided to work during the day, and then I went to school four nights a week, six to nine pm, carried full credits, sixteen credits a semester. And I would work fixing laser printers all day. But 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-bought modem, which didn't make me have a 1,200-bought modem in my PC junior.

5:31You 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 a Tari 2600, and it could play Tank, was the game that came with it in Pong. And so my dad bought this for us when I was six or seven years old in 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.

5:59like computers are gonna change everything. And then I happened to hack some software. We used to, I ran a lot of scams. But you told us about the VHS. So VHS, Jason's hop 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 bucks. And then we started like hacking and doing what was called phone freaking. When you were doing this stuff like, It's you'd be reasonably technical to do it. Not like the, you know, not like was the act technical, but like, you, you, we saw our chips sometimes we changed. Yeah. Like we put, we 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, 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.

6:52Doing the boards. I'm gonna be the guy writing about the people doing the boards. It's a very good question. I used to go to bleaker's tree and I used to hang out in the West Village or the East Village. It was like the cool places to hang out. And like a thing to do would be to go to tower records and look at the zine section. So there was a concept of a zine which was short for magazine. But a zine was something you wrote with your friends. You printed it yourself at a photocopy store. It's like blogs before blogs. Blogs before blogs. And I created a zine.

7:21I was like, I'm gonna 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 Alvy, who you might have heard of in my career. We went to high school together. Web blogs? We went to high school together. Web blogs together. Yeah. So but in the early 90s, I did- Which is, I've been engaged at twod- All that stuff. Everything sold to AOL. I think I sold to AOL. But anyway, before that, I did that magazine, and then I had met Jerry Kelona.

7:51at internet world, the first one. And he, there was a booth. That's right, when Jerry was a VC before he was like the Whisperers. Before he was a VC, he was starting to like us. And I think CNG was. And so there was a LICO 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 Klon.

8:09And then I met Jerry Klone in an office, no bigger than this room in Union Square. And he said, listen, I'm leaving Licos, 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 JP Morgan was going to back them for their venture firms. It was 1994, 95. This became flat iron. It became flat iron. JP Morgan was the first big anchor of flat iron. They were half of it. And Masayoshi-san, soft bank was the other half. No way. So they wanted you to come, like, be a VC associate. Not a VC.

8:38Just to read business plans. So the deal was they would take me for sushi and pay me a thousand bucks. Wait, what do VCs do besides just read business plans? Exactly. Anyway, it was today. And so I had the magazine started silicon. I reported 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 VCs is. That's where flat iron made all their money. Yeah.

9:04Then we could invest anyway. But I had a USB, right? Yeah, it's where I went. Flatiron went with Jerry Clooney, then when Jerry decided he wanted to move to Colorado and just chill. Yeah. He had made enough money, I think, and 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. Do you know that great book about it? Yeah, yeah, yeah. And so Jerry was good mentor, but Fred actually became, ultimately, my deep mentor at that time.

9:33And 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 do we'd rather do? And 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. I want to choose. But just to back up to Deo Cities, that's sold Yahoo for like $5 billion. And I think $4 billion. Flat iron was the main investor. Yeah, flat iron maybe over 5% or 10% of it. It was a huge win for them. I mean, Fred was on fire for a New York VC and Jerry. They did pretty well.

10:03They had gotten that happened, 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 in the Bay, but I own New York, and I had Silicon Valley reporter, and then I started one called Digital Coast Reporter in LA. So I had two magazines, two conferences, two email newsletters. That's kind of King of New York, right? I grew that business to $10 million in revenue off my credit cards.

10:32had a 75 to 100 people working for me when I was 27 years old and I didn't know anything about how to run a magazine, how to run Ansel's. I taught myself everything. What do you family think of this? It was pretty heavy 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 anyways, 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 spinoid set, and I was in publishing, but I was also in this new thing technology. And so everybody wanted in on that. It would be like, the equivalent of crypto is today, like at its peak, where like, and you were the equivalent of like, Satoshi or something. Like it was...

11:15Crazy to be the New York internet guy. Can I so we talked all about a lot of this when we did our like big Jason Calcane Empire of Jason Calcane episode with you So I want to like put this on pause so yeah sure people can listen to that You should it's great. We get like the detailed story of like weblogs ink and all that great stuff and you mentioned I want to like Take us from you're as good as the you know, you're greatest, you're, you're newest thing. Sure. 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 Chimoff and I would do 10 times. Yeah. So the, the origin story is pretty simple. Um, Chimoff.

12:08I knew because he was running ICQ. Timoth was running ICQ? At AOL. And I had sold my company to AOL. And like the revolving door. There was like Ted Leoncis had this march to a billion. My Greek brother, a mentor, had this like march to a million offsite. And so I went to this and I just sold Weblogs and like a million AOL users. That was the AOL users. That was the AOL. With Weblogs Inc.

12:37and with AOL and other assets they wanted to buy, they were going to march to a billion users. It was like this crazy rallying car and we had these T-shirts, march to a billion. So I go to that and I teach them off. And I was like, hey, and he's like, hey, and we introduce each other and we had no one of each other. And I was like, what are you doing here? He's like, I'm running ICQ into the ground. And I'm just riding it down every month that loses a million members. And he's like, yeah, but I'm going to go.

13:01I gotta go to the West Coast. I'm gonna go work at this VC or whatever. Alright, nice seeing you. And so then when he was there, I was in LA. What VC did he go for? Because he was at Facebook. Maybe a field. Maybe a field for a year. And then Sean Parker introduced him to... Zuck. And Zuck needed, you know, like a Chimoff. He needed like somebody who would just... Chimoff be a part of their growth. He built the growth team and he was like, I don't...

13:26There is no equivalent of growth. The idea of growth hacking didn't exist as a term until Chimoff did what he did. He said, just find 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 into beast mode because, you know, he was very hungry. But you guys must have been like brothers from another. Yeah, for sure. For sure. We're definitely, you know, both outsiders in Silicon Valley. And, you know, I had had Chimoff come on the pod.

13:56this we can store it up. That is. We listen to it. It's fun to go back to that moment. And you know, you can see how he's not, you know, polished. He's not Chimoff, you know, it's gregarious or whatever. He doesn't have the loro on. No loro pan. Was he a great shaper? No. Not what I'm saying. He was like a, he was like a dork. You know, like he was, but he was, his business was pretty. 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, you know, confident, you know, even maybe more confident than both of us should be, but. And so I kind of introduced Shemaath to the world by convincing him to come on the pod, which he was like reluctant to do when he was on 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,

14:53It's really good on stage. He's funny, whatever. Which at this point, you had an eye for. One of the things when I was a podcaster in those early days, for about 12 years ago, whatever, is I introduced a lot of the world to the world. I introduced people to the world. Yeah. 2008, I guess, whatever. So I introduced a lot of people who were in tech and it was only a couple thousand people. And then as now, too, You could be a great founder. You could be a great person and tech, but like that doesn't automatically make you a compelling podcast. As we know. No, of course not. No, I mean, I have my own theories about what makes for a great guest. We'll put that on the side for now. But anyway, we start a friendship. We start playing cards together. We start hanging out.

15:36You know, trading notes kind of thing and he's going to start his venture firm. I'm a scout at Sequoia. All that stuff we start playing and trading notes. Let me just become great friends. But then he was coming out of CNBC one day and he's like, oh my god, you know, just like we have such a good rapport when you interview me because he had done a bunch of interviews with me on stage and stuff like that on my events. He's like, I want to do a podcast with you. I was like, yeah, you can come on this week and start up anytime. It's twice a week now.

15:59And which it's now five times six. I'm going to go back down to five next year. It's a little much right now. You're killing yourself right now and you're on act three. Yeah. I have more energy now than 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 20s. But for different reasons, different type of energy. Anyway.

16:25Tremoff calls me, you know, coming out of the studio. I don't know if he was in New York or if he was in the one market one in San Francisco here, but he said, well, I'm just proud of you. I said, okay. And he said, well, I want to do a new part with you. Just me and you, we talk. I was like, sure. He's like, what should we call him a texting microphone? I was like, we should call it all in. And this is 2020? Yeah. It's like two years ago. 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.

16:50because you've been referring to this poker game on air. I was talking about it once in a while, the poker game that doesn't exist. Skydaten 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 Chimoff had had a poker game, Sacks, I had hosted it, floating, and putting all that together.

17:13Yeah, I'd refer to it many times in the pod, but try to keep it from becoming public, right? But it was me, Bill Gurley. It's all public now. Mark Pink this, right? Or maybe he was- I think it's that used to come to the code one. Yeah. There's another funny story. And that's the funny story of my life. But anyway, so then the pandemic happens, and we're like, we'll stop. We're letting you go and just drop in these little red curbs here. We gotta pick them up on the other one. Yeah, some point we gotta pick these up. Anyway, at some point I'll write about it. Anyway.

17:41Nine years. Third book. Anyway, the pandemic starts to happen like, well, Saks has some ideas about masks and then Friedberg. Saks and Friedberg weren't, there was no besties originally. No, no, no, no, no, no, no.

18:00Freeberg and I weren't besties before all in. I mean, we knew each other. We were friends, but not besties. I was besties with Sacks and Chimoff, and now Freeberg is a bestie. But he played in the game, obviously, and we had just started to have a developer friendship. But anyway, that forced him to kind of click, right? Pretty quickly. And I think, you know...

18:22I 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 had sacks on many times and Shamath. So I was very comfortable with that. And at the poker game we break chops and I make jokes. And Shamath's a great host. And just very comfortable with each other. And Freeberg kind of joined that group. And it clicked.

18:47And 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 I'm a little... In perspective. I mean, I think that's a thing. I'll tell you, I never expected to be listening to David Sachs talk coming from where he comes from politically and where I come from politically and going, that is a good point. And that perspective is like...

19:14so helpful in our polarized world today. Yeah, it's very unique. And you know, around the poker table, we all listen to each other, 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 the enemies kind of situation. Like we debate specific things like Gervidol and...

19:36Who is this adversary? Anyway, it's a great documentary about Gourvardal and who's Gourvardal? They're just two public intellectuals. One was on the left, one was on the right, and there's this documentary, Best of Enemies. In the 60s, they started debating different political conventions. It was the most compelling thing on TV. But they were like friends. Best of Enemies. Best of Enemies. They weren't besties like Saxon IR, but Gourvardal was just, he was gay.

20:04kind of closeted or quietly gay and on the left and Buckley was like a serious conservative and they went to blows sometimes on the show. Like at one point Buckley, I think he called him like a sissy or something like really like derogatory as a gay man and the world didn't understand he was exactly gay. It was like sort of time period in the 60s where like maybe some adults understood like, you know, that's a gay man but we don't say that's a big man. When they got into the town yesterday, we were driving the casters right here by him.

20:33We saw a naked guy in the cast, and I was like, oh, naked guy in the cast. Ben was like, what is going on there? Dude, they got on the top of the nudity in the cast. It's like huge jacked dude walking around, and super sunny, so he's like just all like, stuck, licked down. But did he have shoes on? Was he wearing combat boots? Suddenly he was wearing boots. And then they usually carry us along. 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 and Starbucks because you're gonna sit. Right. Bear ass. And for context, I've explained this to Ben, but this is a thing in the Castro and San Francisco. It's a cult, it's like a...

21:12Now, you see this is like a relic of the 67. Yeah, it actually was pretty awesome because David were like driving up and David goes, oh, a naked guy. It was the most like warm hearted. I had to adjust as well as in New Yorker because if somebody's naked, that's a sign that there's about to be some crazy person in a fight and police and chaos. And here, it means high fives and write-ons. But growing up in New York, if somebody takes their clothes off on a public transportation or in a cafe, like people are getting a baseball pass and 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 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, why do you think it works? Like, is it that you think it works? It's like the number one ish. What are in our business? It's number one of course, but it's number, it was number 28 last week.

22:09You guys have transcended. Like this is more of an attack anymore. It has nothing to do with finance or tech anymore. It has worked. It has worked. It has worked. It has worked. It has worked. It has worked. It has worked. It has worked. It has worked. It has worked. It has worked. It has worked. It has worked. It has worked. It has worked. It has worked. It has worked. It has worked. It has worked.

22:39No, I listened to your pod twice a week. I'm like, it's only on one. 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. Whoa. Reno. And I'm like, you're a dentist in Reno's. Can I ask how you found out about it? She's like, I don't know. She's like, I deeply care about San Francisco politics. No. I actually have found it. And this is, you know, during the pandemic situation. And then that's when I realized it across the world. Wow. What was there a moment for you? Either you for or you where you were like, whoa, this is. You know, I've been

23:09Microfamous, you know, micro celebrity multiple times in my career. Not for me, you know, and I got a lot of famous friends. You know, I'm used to getting recognized. I'm used to people taking pictures. What I'll say is like where it used to be, you know, if I go to Austin or New York, people would say, I would have three people stop me on the street a day if I was walking around in New York. Now it's 20, you know, or 10 and they want to take a selfie and it's, you know, it's just, You're not podcasting it as 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 tried to make everybody, I was, you know, in a lot of shows or a lot of things. I did craft with all in. I was very premeditated in creating some character. I've never really talked about this. But I crafted some character, kind of arcs. The fights are all real.

24:09Trust me, there's nothing tripped about that. But I did say, like, I think I can as the point guard here kinda shape the conversation and I literally created the character of the Sultan of science. Right, that's what it's gonna say. And, you know, Freeberg didn't even have a Twitter handle. Well, there's even a character of J. Cal on all in. Like, there's been 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.

24:38A little bit. I would rather not be honest. I'd rather not be in the punching bag. They're like, you're the poor guy on the show. I'm like, do we need to point that out? So often? You're like nothing. Nothing much. I'm like, I feel like 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. It's okay with me. I could have a plane, I guess. I could get one but- You care about the environment.

25:03Well, no, it's also like I don't want to waste a ton of money and, you know, whatever reason. 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...

25:23Never wanted to play that actually. No, that was not that was just the boys breaking my chops. Maybe it's a little bit of like them Wanting to you know, maybe take the piss out of me a little bit which is fine because you know, I give it as good as I can get it But I think that's probably for them you can ask them when they're on the pod. I think for them that's kind of the disc That's the one they can easily go to is I'm the poorest guy on the show, but like I've done okay. Maybe let's flip it. Like for them, before all in, I mean, Timoth had a little bit of a public face. No, they were not famous. No, they had no mark. 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, but like, if you were to speculate, caveat that it's speculation, what do you think for them all in has like done? Well, I mean, for Friedberg,

26:18Nobody knew who he was except if you worked at Google or you were in VC. Like he was very connected in those circles. What's that? Or Monsanto. Like he's very connected in those circles, but he was kind of under the radar guy. I think really by design, he didn't have any desire to. So I think it's probably the biggest adjustment for him. The 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, 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 created this monster you know and he

26:56at 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 Brad Kersner in, if you can't make it, I'll try to get Bill Gurley to show up or whoever Dremond to fill in for him. You know, and it was always like, I wonder if Freebear would show up, but he's actually really committed to the show now. For Sacks, he was high profile, but nobody really knew him as a Republican. So he kind of unclowed as a Republican on the show. Well, I feel like he was also like, he was,

27:23Almost even more so than any, you know, was not you, but he was high profile if you knew about the paypal mafia money, but he was like the least kind of public of the Paypal Mafia. I mean, on the Paypal Mafia you would say Elon Reid Hoffman, Peter T.L. Max Levchin, Jeremy Stoppelman, Chad Hurley, Ruloff. Yeah. And I guess Zach should be somewhere in that.

27:48like 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 sacks. I think sacks are probably taken on 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 flow on the margins probably. I think there's probably I don't really marg- I wonder, I wonder. He said that jokingly on the show. I don't know. I'm just thinking like maybe there's somebody that's ascended because he's done all in in a way. I guess. Yeah. Sure. I'm trying to think if like, would is there a founder, I wonder, I don't know this, but is there a founder who's a young founder who would say, I would never take money from Peter Till's venture firm, because I'm so liberal. For sure there are. Okay, so those people feel that way about craft now, but

28:38For every one of those there's 10 more. I kind of agree with that. Yeah, I would agree with that. So anyway, I do think like he's choked that it's cost him a deal flow. I don't know if it has. I think it's really the center. The HUD too, I think 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. You know, I've been telling folks from the beginning, I'm an independent and a moderate I voted probably Democratic three out of five times, four out of five times. But mostly that's a function of the fact that I've lived only in New York and California in my life where you don't really get many Republicans or moderates, but I've voted for Bloomberg, Giuliani, when Brea was crazy, and Potalki, who are all Republicans. Were you here doing the same, or are we still here? No, I wasn't, but I would have.

29:32Uh, voted for him. Um, I like competent people and I support a Bloomberg for president, which got me a lot of flak. Uh, I don't understand why people were very upset that I was from him instead of whoever. I think you guys talked about this on the pod that like, uh, what was the two by two quadrant of like, whatever it was, we all think we are here in Silicon Valley, which is like, social, liberal, fiscal, conservative. Yeah. Everybody should be that. But we're the smallest of the four groups. Yes. It is a small group. I think I believe in competence and staying out of people's lives. So it's very hard to know because then even David, I mean, this is, I think, when David and I fight on the pod, which...

30:13Some people love, and I think some people probably turn the pot off when that happens, and they don't like it. And certainly, the Maga group has no love loss for Jayga. I can tell you that. My implies have been really crazy. I would get like brigade in the last couple of like nuts. It's funny, but it's also like on the margins, like they can get a little scary, like they'll dox sometimes, and that's not fun. A handful of times has happened.

30:41You know I had to tell David like David I am not like I don't actually listen to MSNBC and Rachel Maddo to get my information and by the way your pro choice pro game average anti-war Yeah, he's the dove and I was like well, okay if you don't play this game I'm gonna go W David the dove and not making me into Jason the Hawk like What are we talking about here? Anyway, it just goes to show how silly the coalition building is. It's totally silly. Exactly. The two-party system requires that if you feel very strongly about something, then you're not allowed to think independently about anything else. It's so crazy. I think what messes people up is the fact that I actually just think Donald Trump is a horrible human who...

31:31you should do no business with has no business being 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 and so like i would hate him as a democrat or a republican so it's it's not personal and i would or it is personal with him but it's very personally with the party 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 secured office and that's all they care about is winning. I got 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 were we get to agree on something so that we all can find

32:20togetherness 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 i4-14 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. Let me look at the image quality versus the old one. It really is pretty. It is pretty, but I got to be part of a tribe. And that is a thing that no matter what your tribe is, that is so fun to be there on tribe day and tribe day. I will say the thing I'm proud about the show, I think, is that it has...

33:09you 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, especially 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 it's like one of these supervisors here is a super idiot, like guy in San Francisco, who like...

33:36Um, you know, like won't let them build housing or 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. Right. Thank you for the latter. My besties remind me. I'm not working on it. I'm working on it. I'm not trying to be a billionaire. Thank you. 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.

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35:43Another thing that's really fascinating to me about all-in 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 SVS-V. Oh, that'll came from David Filo.

36:08David Phylo and Jerry Yang were driving their old cars right like the cool thing like you you could like make money But like you never want it like you never and be understanding you guys I think of the first like like you guys like whatever like we got a private jet like that's fine like you know, I mean listen, I 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, literally the book I'm right, my second book right now I'm writing is about wealth and money and like but not like in my regard but in a sort of like big picture societal regard so I'm like literally been thinking about this topic a ton and I think we worry a little bit too much about wealth creation with a small like outlier wealth creation and we 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

37:07I 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.

37:32When 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 OpenCourseWare 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, you can build a business there, like David Centro over the founders podcast, like Mr. Beast and KBHD, like, nobody gave me guys permission. The world has been equitable. Yeah. But people want to spread a narrative that the world is unfair. And like, I watched The world becomes so fair and so just and so much information and opportunity become available that I'm like wait a second I Could never figure out how a term sheet worked and nobody would share their term sheet and now there are a thousand videos and blog posts on how to Negotiate your term sheet the world is still unfair. I think I vary I think the key insight is like

38:24recognize 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 find it's very weird in the world. I think there's like a group of people who want the world to be more unfair than it actually is because it makes them feel more virtuous signalling goodness. Well, that's their community. That's how they find that there are other people who love that they tweet that the world is unfair. And they have to, and it typically is a certain type of person. I'll just leave it at that.

39:20Okay, can I, so I'm going to write a question. I'm going to go to each founder university now. I have a course where I teach people for 12 weeks, or I should say I have a team that teaches it. And I'm going to actually teach it myself this next cohort where I just teach people how store companies. All right, let's plug it. How can they find out? We're going to go to the university and that's that. There you go. Yeah, I mean, it's basically it's free. 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...

39:47straight back, the card back, the 700 bucks. If you don't come, or if you don't have an excuse at absence, if people miss something because they're their kids, we're gonna be fine. But we just try to get people to complete it. Over 90% of people completed. That's cool. So, and then we're investing 25K in some of those folks to help them start their companies. Like people don't know all the work I'm doing like quietly, but like 200 people go to this course now. Maybe I'll have 400 in the next, 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.

40:16Yes, they can. You have to have gone to Stanford. I'm like, no, I'm invested in 350 companies. Maybe 5% of the founders went to Stanford. No, that's just not, it's patently false. You have some confirmation bias. You're dealing with a data set from 10, 20 years ago. I get it. But I'm telling you, on the streets, ground level truth, we all meet with founders all day.

40:40It's never been more diverse. It's never been more open. Nobody cares where you went to school. No one cares where you live anymore. Nobody cares where you live. They care about what you've felt in your traction. Like, it is post pandemic. All people care about is like, show me your metrics, show me the product, show me your team. What are your skills? Great, let's go. What's your growth rate? It's basically become like as beautiful of a meritocracy as I've ever seen. I mean, you say the M word, it freaks people to fuck out.

41:07I'm like, why is this so scary for you that Silicon Valley is a meritocracy? And they're like, because it's not. And I'm like, it kind of is. Can I can I answer your question earlier of what why I think all in works? Yes. All right. Go ahead. So I think you're the you've got the perfect storm of three things. The first thing is on this out there. By the way, billionaire born. Most people, your counter position. Most people who attain that level of wealth.

41:34crawl into a quiet hole and make sure no one knows. You're doing shows from boats and jets. Yeah, so there's like, I don't know if we've done one from a jet, but yeah, there was definitely two boats in the last three years. That's true. In some peak moments of all in, it's like watching billions in real life. It's like, you hear, you hear Chimoff 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? And like, there's, there's this interesting entry there. So bucket one is like billionaire porn.

42:03Bucket 2 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 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 masked. All four of us are information junkies with a lot of research and teams. How many people, all in, how many people touch an episode of all in? One, producer neck, that's it. No, I mean, the research still, I know. I'm pretty sure. There were test files open on people's computers when they're talking.

42:55We 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 right and I I think sacks has some research help I'm sure Friedberg and Chimoff read the stories are there 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, like you do 20 meetings a week with founders, they're going to tell you everything about the world. 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 journalists for 20 years, you 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. So yeah, we probably have a slight information edge. Yeah.

43:51Certainly a huge infer 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 I now looking back on it. I think we had between five and 35% of a story And I know that's probably triggering to a lot of journalists that they have that little information. You weren't on the inside. But you were on the inside. So when you're on the inside, you have 100% or even on the inside, you may only have 50% depending. You get enough to run with and you feel like, okay, now there's enough story here. Let's do it. And that's clearly not the whole story, but it's enough to put the piece together. And then over time, process journalism as some people have dubbed it, maybe the six or seven stories will tell the full story. Which the third component?

44:46It makes it successful. It's the thing that David and I took forever to realize works about acquired, which is relationship and charisma. Like people like having fun by listening to stuff. Sure. And so, like, if we can make history fun, then- A little bit of joy, listen to four hours of stiving into stuff, you would never read in a book. And you guys do that in spades. Like 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 1% content find it compelling is just yeah, that's right Listen every week. Don't miss it. I can literally walk in the baby up and down the hills listening I have people tell me they listen to it twice. They take notes. I'm like wow, that's great You know, I don't think that maybe I should think well anyway, I was very intentional with my role in it to step back and be like the point guard

45:40But, 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 Free Break host episode come about? Well, one week. Yeah. You switched roles. Well, he was like, I think this could be done better. This could be better than that. But I was like, go ahead. And I just like, sure, I'll just shoot. Like, I... And... You passed the rack, and I'll... I was like, yeah, you want to be more like a grand show. And he did a solid job. But let's be honest, like... It's not a point guard.

46:10It's not show time, that's for sure. Like, I don't think people are gonna go to watch him play point guard. I mean, he did a serviceable job. And put that on his tombstone. No, I mean, but he shines when I created science quarter for him to shine. Bring me a sign. He's like, ah, you know, I don't know if I want to talk about politics. I was like, listen, sax wants to talk about carnivorous politics. I'm giving him his red meat. Here's your quinoa.

46:35come to me with a science story. You know, and we'll do this. Kinwa Corner kind of thing and I've made him the Sultan of science. So good. You know, it was it was a distinct effort. I really wanted to make him shine. You know, and it worked. You know, it worked because you see how engaged he is. And what used to happen was and fans know this. I'm not speaking out of school here. You see it every episode. Sacks would disengage during science and Kinwa would disengage during politics. Yeah.

47:01And what I've been trying to do is keep both of them involved when the other is doing stuff. And Shamaaf and I are involved. That's a hard job. That's a delicate. 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 grew up on McLaughlin. Super unfamiliar with McLaughlin. 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 pretty contankerous. And if he didn't like what people would say, he'd be like, wrong, this is the answer. And it became so competitive that you wanted to watch it. Yeah. Now,

47:55what I didn't realize by adopting that would be that sacks is the ultimate debater and will fight like a dog until he wins any debate. And so I may have pushed sacks into more of a debate situation where I'm trying to not have it be a debate. I'm trying to have it be a conversation. So what I've been working on is trying to keep it be a conversation. And then some people in the audience are like, you have to be the fact checker for sacks. And I'm like, No, that's not my own job. I'm not real-time fact checking sacks. And so that is a delicate balance of like, and then sometimes I'll ask questions, specifically because I know the audience doesn't know what, you know, fair market value, and they hear an acronym in me. So I'm like, explain that. Right. And I'll stop somebody. Now, I mean, you're, you're expanding the tim to dentists. Like, that's correct. Thank you. So people are like, oh, J. Kyle's an idiot. He doesn't know that term. Or I say to somebody, can you unpack that? Can you explain that?

48:52Obviously, you build that term myself. You were with the third or fourth investor in Uber. Yeah, exactly. Well played. I think he's been in Robinhood too. I like to. Wow, who knows. And I'm like, dude, 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.

49:22And, you know, in that role, I'm acting on behalf of the audience and I get the sense, like, he's going, Tiamat'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, oh, most of this. And that's what I think has brought in to your point, a lot of the dentist's crew. And having an intimate sense of where your audience's edges are is like really important role there. Like, when we're guests on, I'm always trying to catch Yes. Where did they just go slightly too deep and I need to pull them up, so do we. Yeah, and you know, podcasting is about going deep. So it is really an art. Like you want to stop somebody when they're going down this like crazy rabbit hole. They're going down some rabbit hole.

50:07that has never existed in media before. Right. And you want to let them go, but you need to make sure they're taking the stairs. Because 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 connected to something they understand. They just jumped into brain surgery. Yes. Let's just explain to us what's going on here. Let's know how we're going to chop up this brain. Right. Yeah. It's a bit of an art. But I have to say, it's been a different muscle for me to flex, and it's been great fun for me. The other thing, I don't know if you think about it on this axis at all, but

50:37I kind of think of there's, I use to think it is very binary. Like there's two categories of podcasts. There's candy and there's vegetables. And like I listen to the audio version of Stratekery and that's my vegetables and it's not like deeply, it's enjoyable intellectually, but it's not like fun. And 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.

51:03And like sometimes even at home so I can take some notes or look something up. I can be. Sometimes you're hitting 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, I didn't actually miss anything because this has just been like, it's comforting. Yeah. It's like I love all the stuff he's talking about, but like it's not.

51:30must listen every time, every minute, every second concept, and I'm not using hard parts of my brain to understand. But then it's become candy-advigables. It's both. It's both. Yeah, I try to try to do it with this week and start ups and all, and try to have it be both a little bit of personality, a little bit of entertainment, some fun hot takes. Yeah, I mean, related but separate topic. Silicon Valley. Yeah. I feel like, especially there's a lot of...

51:57Part of the origins of all in there's a lot of like bashing on San Francisco politics and Kelvin like there's a lot of crap wrong here Yeah, but you guys are all still here How are you guys feeling about it? Yeah, how do you how do you feel about that? Like what do you think of the area? You know, I lived in New York Brooklyn them in Hatton and then I lived in L.I. And then I lived here and so I think my I'm moving to places I enjoy less than less each time. 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. Which is why are you still here then? There's no reason for you to be here. I'm here because I had a lot of friends up here. And I had done LA. And I was like, I wonder how far 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

52:49how I would do if I was up there in the industry. And I was kind of this life. Because if you wouldn't, you'd always wonder. Well, Michael Moreci used to call me the mouth from the South because they had like two investments in LA. Oh, the mouth from the South is super. What have you got in your stomach, Jake Al? Sir Michael saying that. But I moved up here. And you know, so I love it up here. It's quite bucolic. My kids are loving it. It's quite nice. I would love to live in another city in my life or two.

53:15I could see myself in Austin or Miami. I like both the low cities. I think Austin's kind of the future. I think California's gonna be damaged for a decade or two, so I think for the rest of our adult lives this now. Because in the pandemic or I think the politics and not appreciating the politics, the regulation and not appreciating the tech industry is really the problem. And then you look at this guy Dean Preston, like he is dunking on The founder of Away and Stuart Butterfield from SAC, they're a couple. And he's like, we got a million two out of them when they sold their homes. And I'm like, and you also lost two incredible founders who've created billions of tens of billions of dollars of wealth for San Francisco, you idiot. And like, at the same time, Francis Suarez in Miami is listing.

54:04All of the venture capital and doing a tweet storm about all the companies that raised venture capital So you have one guy Dean Preston dunking on people saying we have this 1% so when they sold their 30 million dollar house We were able to extract a million to that's why tech doesn't like when I was like hey dummy Yeah, now the all the future earnings are gone now what's that? Hopefully the marginal tax rate is 13 0.3%. I mean, but just they haven't exit tax now for homes in San Francisco. Right. So if you're home cost 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% of their future earnings stream. Literally, the chef at Slack made a billion to paid a billion to in taxes. Yeah. From their RSUs. Like, are you such a, where do you think that's a certain problem? Yeah. Like the bill, the million two. Yeah. But that will have to.

54:56probably paid in taxes on their RSUs at Slack. Like, you absolute moron. Like, you're literally so upset about their mansion and dunking, and you're dunking on an individual's name. But anyway, the fact that we hate entrepreneurs who create jobs and wealth, or certain people do, is just insane. It's just insane. Like, what, I mean, you could go change the tax code.

55:23It's fine. Raise them in one way. 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.

55:52You wanted free college and couldn't get it done, he gave it to Amazon employees. You wanted a $15 minimum wage, he made a $22, and you wanted everybody to have universal health care, and he gave universal health care. Like that is literally what Bezos did to them. Maybe you could do that like them pushing it and pushing it. No, no, definitely, it is literally him showing like, as the Amazon crew showing like, let the free markets work. Like the DoorDash, Uber, Amazon, Starbucks, absolute race and battle to just hire entry-level employees and make it delightful for them is what has driven, you know, and a lack of immigration, is what has driven these salaries up, right? And the benefits up. It's extraordinary what's happened with the free market. It's just come to it. It's still seven dollars. Federal middle wage is seven and change, no, right? And 15 here in the city in New York is 15, like,

56:52Yeah, that's weird. All right, listeners. Now is a great time to thank our longtime friend of the show, ServiceNow. If you are running a large enterprise, AI agents are likely spread across every team and deploying them is no longer the hard part. 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.

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58:31So 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. We referenced this at the start of our conversation. You're working as hard or harder than you ever have. You said you've got a new well of energy. Yes. Tell us about it. Well, I find great purpose in what I do.

58:57And 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 realized my life over the last two years. 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 life.

59:22Working like no offense to my incredible lawyers but negotiating in terms of 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 maybe it's a thing that creates value enough for me to do it. Doing my podcast every day. Absolute joy.

59:47entertaining an audience, you know, thinking about the world and having these conversations. I had Toby from Shopify on today. Like, I leave the Toby interview. It's like his third or fourth time on the pod. And it's just like, instead of us having dinner or lunch, we just required a pod. At the end. And to me, no, just, you know, he had to start it because he did that tweet about his compensation tool, where, you know, here's your total cost. I was like, that's brilliant. Come on the show. I want to come on the show and talk to you guys. Like, yeah, of course.

1:00:17And so, like, those conversations, I just looked at them and I'm like, my energy coming out of the show is on 11. Why am I not doing this every day? And I watched Howard Stern when I was a kid or Charlie Rose do it day in and day out and I was like, I could be like those guys. They every day get on there and they seem to love it and I do and so I just commit it 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, who I respect and who's awesome and bring something to the table that I don't have. And 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 the decade.

1:01:13I, uh, well, I, you know, I'd have guests on. It was a large, a guest driven show. And then I would do the news roundtable once a week, because it was once a week, then twice a week, then three times a week. And then I was like, well, however many I just sell out, I'll do it five, six days a week, whatever. Um, and, um, I enjoy meeting with founders, uh, when they fit a certain profile. Uh, but it's very hard to meet with a large number of founders, given how many are coming in. And it's hard to work with them when they're just talkers.

1:01:42Yeah. 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 at university where if you want to build something, I will talk myself to 200 people, you can build and then whatever rises 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 a product of 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 understand 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 in my career as an angel investor doing 50 million a year now. 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

1:02:41It'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 a better at it. There's 11, I have 22 people and 10 on the media sign, 12 on the investment side. And of the investment team, like people don't understand, they're like, oh, you're a solo GP. I'm like, you have 12 people.

1:03:01Those 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 a hundred meetings a week shortly probably across 10 people or twelve, but you're not doing the I'm not doing them. Yeah, and what happens is you had this line wizard on it was on twist I think you know, that's a lot of people say that's a lot of work. We really give enough for me That is the new philosophy. This is why my energy is really high. This is your I have to 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. I'm looking for, you know, a fixed 50, a solid 60 hours a week, if you want. You don't have to match me 67, but 60 or 70 hours a week, but keep up. And are you looking in that team? Are you looking for, like, the next Jason Callicanis to be a part of that team? Or is it, like, someone who likes doing that part, like, well, let me ask it more directly. Is it someone who's content with doing this? Or are you looking for people that are, like, hungry enough to be the next Jason?

1:03:59I'm open to all of it. I'm open to all of it. They don't need to want to have my absurd unhealthy desire in my youth to be successful. And if they did, they probably wouldn't come work for me, but maybe they would. Actually, I would. So yeah, they probably would. Not for very long. Yeah, my brother, you'd come, you'd learn years, you'd extract it too. People come, and they work for two, three, four years, and they go start their own venture fund or whatever. Muscle talk, it's great. But what I...

1:04:28Told them most of you know, just find the great companies. And I looked at investment team meetings usually there Monday. People do it for an hour or two and then they go to lunch. I said I want to do it twice a week, Tuesday and Thursday, it's 2 to 4 p.m. Hit me with companies. So that was another innovation I did. And I also brought Mike Savino, who was my first boss when I was in my 20s doing IT. And I brought him on as president. So this is like one of my lifelong best friends. And I said, run the company. Here's what I want to do. The podcast, meet with founders.

1:04:58do the LP fundraising, that's it. You know, teach, of course. Are you enjoying the LP fundraising? I am now, yeah. I'm kind of like, remember it acts, I don't know if you watch Billion. Oh yeah, every episode. Great. So you know, like at some point, he was like, I'm gonna go raise money. Yeah, it's cap raised time. It's cap raised 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 literally, was like, we're doing 506C and they're like, and so you've talked about this now. You're now, you were in kind of this one bucket with your capital and now you're going simultaneously in two directions of you want the public and you want the big institutions, right? We'll see. 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.

1:05:52The first fund I deployed in five years, the second fund two years, the third fund two, and then five years. I was just, that was my first fund. It was, you know, me, Bill Gurley, Dave Goldberg, Rest in Peace, Tony Shea Rest in Peace, David Sachs, Chimoff, just a bunch of my friends put money in. And it was to see if I wanted to be a venture capitalist and do this as a career. And I was like, yeah, I just did it over five years. And the second one I raised 11 took me six months to a year to raise the first.

1:06:19It 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 think I'll wind up raising in the first ten days what I raised in the first... Yeah, a couple of funds. I literally did two webinars, a couple of hundred people came to each show. For people who are listening, 506c, is you can raise in public. Which means you just can tell people I'm raising a fund.

1:06:47And 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 aspiring VCs raise publicly, right? Yeah. You didn't raise publicly. No. You should probably. 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, Mac, the VC. Yeah. You did a great episode with it. Yeah, it was great. I had them on. I had like, you know, first-time founders for a season of Angel. It's just like a subsection of the This Week in Seraph's podcast. And I became an LPN's fund and you just saw me like I just did like hundreds of meetings. I did like five meetings a day for a year. And I rose my whatever $10 million. And he's African-American and he's like.

1:07:32It's just a matter of hard, do you want to work? And I'm like, well, say in that publicly because there's a group of people who do not want you to say anything. He's like, no, all you have to do is like, go to Angelisha, set it up. And then you just are talking to other VCEs, you talk to them and you just have to be willing to take 50 meetings a week. And I'm like, do not say that it's easy to raise a venture fund. That's a black man in Silicon Valley. But it's not that it's easy. But you find your people who believe that could you. And then they believe in you and then they back you. Correct. Correct. Correct. And so the whole thing goes, but what I know

1:08:02when I was taking my notes, watching him was so many times people, like, oh, you're, when's your next fund? And I'm like three years. They're like, oh, let me know. And I'm like, okay. Right. I'll put that right there in the place where I keep everyone who tells me three years. Yeah. Yeah. Yeah. And so, you know, I mentioned it on all end. I'm.

1:08:22tweeted it, and all of a sudden, you know, I had 1,000 people sign up. Is there a limit to the number of LPs? You can have more than $250,000 accredited up to 10 million, and then 2,000 QPs. And so it's a lot more work. And QPs. Not for you. Not for me. Not for you. But not for me. To catch your eye.

1:08:38to serve people looking at you playing Jason. I know you know what a QP is. I just want to ditch the ball. I think it's five million in investible assets. Yeah. And then accredited now is 200 if you're an individual for the last two years, each of the last two years and 300 if you're a couple, each of the last two years in income, or a million dollars in net worth. In net worth. In net worth. That's not every primary resident. 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.

1:09:05and 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, where the book Angel was the first syndicate on Angelist, the most successful syndicate on Angelist, 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 Angelist, these are like, those are big numbers.

1:09:31You do something consistently. For SPP, he's unhingealistic. We have the fun too, but like, you know, yeah, like that's a lot. You're hurting cats, so you need to have a lot of people. But anyway, putting all that together, I think now it's the time to democratize venture capital. So that's what I'm attempting to do here is I want more people who are accrediting qualified purchases who've never been in a venture fund.

1:09:52to look at the asset class and just consider it. It's high risk. It's high reward. I'm in 20 venture funds myself, including yours. Thank you. But don't, but don't pitch Jason. I'm sure I'm going to do yours. No, I mean, I'm just going to pick them based on people I know or people I know online or people pod and yeah, I'll probably do one or two new ones a year. Well, this is kind of to the 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 gonna just invest in your fund, but if you go do stuff, and then people are like, oh, Jason does stuff. Great, I'm a back-to-ace, Ben does stuff, I feel like. Be a Vaction. Yeah. And it doesn't mean you have to start a pocket, so you could be a blog, you could do whatever. Whatever you could create, founder, university, whatever it is. You can do any of those things. You could have a track where you could be an advisor to start-ups, whatever it is. Do you like the idea? I'm curious, as someone that's always raised from sort of individuals, do you,

1:10:44Do 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 dollar checks in the fund, 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 or cancer survivors, to have moral slow-caterings in doubt or an endowment. You see that for something like that. Yes, 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 even more meaning in what I do. And I got that from Sequoia, 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 where four foundations are doing, here's where this foundation is and you're doing it. Yeah, their conference rooms are named after their offices.

1:11:40And this is really powerful. Like I find we have like state pension funds and stuff like that. It's not gonna make you get in PSL ventures. Like you take it much more seriously. You're like, it's because it's not just about the reward. It's not like, oh, I'm so excited about what we're gonna do for them. It's like, this is really important to preserve and 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 like one of the seasons of that of billions was he's like, I'm going to be a family office. No, I'm going to raise my own phone, right? And so there's this natural tension for acts like, what should it be? And he decided, yeah, I like when I have other people's money because he seemed to perceive like, I think he felt that he wasn't a somebody in his ecosystem in his community with me.

1:12:36Managing outside cat. I think it's like playing, you know, in the bubble with nobody in the stands versus... Right. Getting on the court at Madison Square, and there's people in the stands. Your numbers don't mean anything unless you're putting them up for... Dude, I'm doing this public, where it should say quasi-public, people still have to sign up to, you know, come to a webinar.

1:12:56But I'm sharing with them like here's my, the totality of my investments and here's what I've done and here's what I plan on doing with my team. So, you know, I'm kind of enjoying it. And if, you know, I've met with all the top endowments in the world over the years and they're very kind to me, but it's always been like solo GP is a block or no track record. You're fun just so small. We're a $50 billion endowment. Yeah, and, you know, like, you know...

1:13:22At some point, one of the ones who's the most rigorous, I would 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.

1:13:51And 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 was in the last fund cycle. That was in the third fund cycle. Yes. So now. So I will contact them. What I decided to do is let's see what.

1:14:13My syndicate members and the public want to do. Let's see which two P's 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 gonna do five webinars this fall and that I'm gonna go on the road and start meeting with folks Are there any downsides to doing the the raising in public thing other than I'm not that I can see I mean I guess you could fail in public to fail to raise the fund that doesn't seem like something you're scared of no I could also, you know, the fraying thing, you know, is I looked at the model and I said, you know what I could do, I could just invest my own money in each company and then syndicate them and never have another LP. 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.

1:15:12I could just say, I'm placing this bet. Would anybody like to join me? Yeah. 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 this, you know, we'd 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 quest of like, 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, Yeah, I could go do what you are actually doing and like raise, have LPs via count of it. Yeah, 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 to be obnoxious about this, I know it probably sounds that way, but

1:16:08for a kid who's gonna be a cop to be where I am. And this is why I like when the guys break my chops on the pile. 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 early founders and be able to say, 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 twist episode 180 with you and Travis. Yes. I mean, that was... That's the secret for the show stuff, David. Yeah, that is the secret. But from the juicy, I can talk about Travis. Yeah, but that was like, you know, Erbu was such a baby company back then in like, crazy one city.

1:17:07I mean I invested and I had an open angel for him where Siam Bannescher and Chris Frallick from first run invested in the company. I think they both met them there. Soko was there too but he already had a relationship with Travis so I can't take any credit for that. And Kevin Sistram was watching and I was going to kick him out because he was at this co-working space called dog pass pass. I worked there too.

1:17:29Yeah, so he was, oh, coach, we didn't know that. Yeah, so he's sitting over there building bourbon. Yeah, it's right. Sock is like, can bourbon come in? I'm like, fuck, no, this is like private shit. And he's like, but, and I'm like, just tell him to sit at his desk and I'm working on him. Wait, this open angel form was at dog patch labs here on the pier. No, I think after a year, then they shut down because it was going to collapse. Condemned, yeah. Condemned. So that was there. No, I also did a bunch of like events there for angel lives. I, at the time.

1:17:57No, Vola and I were very friendly. Not friendly now, but we don't hang out or 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 an in person. And he's like, I'm going to do a single angel list. I'm like, well, I'm just in person thing. And it's like, great, let's just, you know, trade notes or whatever, then he sent me the syndicate thing. He's like, do you know about SPV? So I was like, I don't explain it to me. He taught me what SPVs were. He introduced me to a short fund management, which I wound up investing in. Did you buy that? I didn't buy it. I mean, about 5% of the company I was interested in it, but they back everybody and they've done more SPVs. Like, look, I don't know if they're up to 10,000, 5,000. I mean, they've done a ton of the seriously great group over there. And so he taught me how to do syndicates. And the first one I did was

1:18:51Calm. That's four or five hundred dollars. That's not. It's funny. I was looking for you. 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 less than Uber multiple. It's still good and Uber multiple. But you look at calm.

1:19:13You just, I looked at David and I was like, he sharpshootered that one. That was even more proud of because, I mean, T.O.Y. It was like ridiculously early, and like a super low basis. They had, it was $4 million, we put $378K and it was 6% and they didn't raise any money until it was a $250 million dollar motion. It's a no-down motion. Sharpshooter. And...

1:19:36I could even cry, like telling the story, but Alex, too, and I, I became very good friends. I had Michael Acton afterwards, because he wasn't actively running. While Alex was, Alex had some conference. I was interviewing him and doing a little victory lap for him and giving him his flowers. And he said, yeah, 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?

1:20:06But 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 for you. And they found product market fit while burning through your money. Yes, I think so. I think so because you're like, take more of my money. No. I mean, if you think about that as like a That is not the case with Uber or Robinhood. I was along for the ride. Let's be honest. I did not change the trajectory of the company. But like, but for Jason Callacannis, that's what they said. Well, he said it's they were going to shut it down possibly. I don't believe that they would, but I do think it was on the table. That's like real angel investing. There's a lot of like individuals participating in ventures and like no fence.

1:20:59So like call that angel investing but like coming in when the company could die Needs a hundred K 200 K 300 K to get into the stage where they haven't you to date I think when I invest ever Yeah, because they were selling the app for $10. Because remember, I think early stages, there was no subscription model in the App Store. You just sold an app for $10. That's right. That's right. So the business model of apps was make a lighter for a dollar, then make lighter too, and charge $3, and then lighter for would come out. And you would be like, well, this doesn't make any sense. Making Microsoft Word 1.0, you buy it, you throw it away, and it's like, but we could just update it. Yeah, but we need to make more money, so shut the old one down.

1:21:40So you buy angry birds, and you buy angry birds, two angry birds, three. It was a really weird time, and then they were like, yeah, we're doing so. They told me like, you know, because I was under NDA as well. Hey, subscriptions are coming. That's going to change everything. And they were going to do $10 a year. And I said, Alex and Michael, how much does it cost to go to a meditation class? It's donation based. And there's only one 10 places you can go. I'm like, well, what's the suggested donation? It's $20. You want to switch $10 a year? It's $20 a month.

1:22:10How often do you have to do this to get back? Yeah, it's 20 hours of visit. I said, how often do you have to do this to get value? It should be a daily practice. How often do you have to go and learn? I said, if you go weekly, that's good. So it's $80 a month to go and we're charging $10 a year. So that's like $1,000 a year versus $10. Whatever it was $10 a month, we've been thinking about that. I was like, Okay, and they're like, okay, yeah, I think we're gonna do that. And then they went to $10 a month or whatever. And they never wound up at $60 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. That's a very early to very successful. And I'm curious.

1:22:53Like, did it feel any different when you were making that investment where you, like, there's something more special here than my normal investment? Absolutely. Yeah. 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 was, when you look back and you're like... Nine factors. Nine factors. Okay. All right. Yeah.

1:23:17Well, angel, angel that university. No, I'm a nutrition angel at university, but 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 antilist, 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 that information, so I won't give all of them. But one of them is world class design.

1:23:45and so I'm trying to teach people what world-class design is. The 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 Comm or Robinhood, okay, they're the best looking app with the best UX of all of everybody in the category. So Comm was better than headspace, Robinhood was better than Detroit. 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. I'm 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 I'm like, oh, that's on this product page. I'm like, okay, again, that's just like the, I mean, if this was a bank's website, maybe, but that's not world class. That's

1:24:40serviceable design. That's utilitarian design. That's okay design. That's good design. It's not world class. So let's, if we're going to say world class, like a world class performance is different than a serviceable performance, world class cinematography, world class script, world class dialogue. That's different. And that's, and then product philosophy is the other one I like. So okay, we met with this company in June. It's now July. What's changed about the product? And they're like, we don't know. I'm like, okay, well, let's find out. Where's their change log? Where's their roadmap?

1:25:10So 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 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. And then you go like if we're with Rahul would superhuman and I was investor in his company before that report of Rahul like the change log at superhuman superhuman that people don't realize like The like, bank, bank, new feature, bank, new feature. Oh, boom, we fixed Grammarly. Oh, bank, 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 quote. We should ask Rahul this. We've had one of the show three times now. Product genius. Like, the parallels between superhuman and figma are uncanny. Like design led founder, like Rebelou Shari design in the software, rewriting the entire browser stack and we're gonna get the performance. And I remember it being breakthrough when it came out.

1:26:05and then the only thing that I can recall being different between then and now is adding a calendar thing that I don't use in a mobile app and iPad support. And why? Outlook support. You just don't, you know, when you hit command K, you probably know 50% of the features are right. Do you use remind me of this? I do. Okay, great. Do you use labels? Do you do still? I do. I do. Okay. Yeah. Which it was all there when I started using it. 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. I really like want them to make snippets multiplayer. I want to share my snippets. Oh, yeah. Oh, is your team? Yeah, I love. Yeah, so I want to love David's pass emails. They're so nice. I don't. You do it on the phone. No, no, I don't. I don't. I don't. I don't. I don't. I don't. I don't. I don't. I don't. I don't. I don't. I don't. I don't. I don't. I don't. I don't. I don't. I don't. I don't. I don't. I don't. I don't. I don't. I don't. I don't. I don't. I don't. I don't. I don't.

1:27:04I'm trying to have founders. I don't know that I'll be successful in this may be a mistake, but I'm trying to just not have, I don't end up having a conversation with a company if I'm not going to invest. No, but you must say, hey, we are not going to invest. You've took a pitch. Oh, no, I'm getting it. I don't, 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 upfront. You frontload it, the dad, everything. We're in this unique, Because as you are too, but with acquired, we have every six months, we have six companies that we work with on the show, as our sponsors and our partners, and we get to know them really well. It's good. And I'm not an investor in just about all of those companies, so it's not like a... It's growth-staging investment. It's growth-staging. It's growth-staging. It's growth-staging. It's growth-staging. It's growth-staging. It's growth-staging. It's growth-staging. It's growth-staging. It's growth-staging. It's growth-staging. It's growth-staging. It's growth-staging. It's growth-staging. It's growth-staging. It's growth-staging. It's growth-staging. It's growth-staging. It's growth-staging. It's growth-staging. It's growth-staging. It's growth-staging.

1:28:03pricing is going to be hard. We'll see. We'll see. We'll see. Yeah, I don't know what's going to 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, the cops got hit 50 plus percent. Yeah, I mean, they got hit harder again.

1:28:20Yeah, I mean, I'm buying equities right now. I've been doing it at jtrading.com and I am gonna buy more. Sorry about all the pics a couple weeks ago. Which one? Whatever, I think. Oh yeah, no, no. I actually love Taiwan semiconductor. It's fixed with the other one. It's fixed with the other one. No, it's fixed with the other one. Twilio was yours, and I love that one too. And I like Shopify as a pick. I'm actually really enjoying it. It's really not investing out. Not investing out. Not investing out. But it's balancing out my 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 blast or no, I'm a Jedi user, I'd say. But, you know, I'll learn if you look at the blast very best. It's not, it's helpful. It's really helpful. If you look at the very best people, the best GP's, like, whole adventure over the past.

1:29:11two decades, they all trade public stock. And they do it for the same reason. They're going to fight with the Saber, but they want to know how to use a blast. Or how to fight in the next wing or something. It's not what a Jedi does, but Jedi will do it. It also keeps you really sensitive to the public cycles so that it's not that you have to...

1:29:34Think 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 gonna be in 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? 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. I'd like to join a public board at some point. Probably not a good idea for me to have said that because I might get an info for one and that might be too much work.

1:30:20Yeah, but hey, especially given the market right now, I'm very very careful. But you could also buy me to do that. But it's just, it's great. Especially through the show now, you have relationships with public company founders. Sure, of course, yeah. And if I really wanted to, I'm sure I could lobby. Oh, I'm going to, you don't have some on the board though. You can have a great relationship. Yeah, I'm doing the analysis and I'm doing it anyway with Molly every day. Okay, you know, Twilio's or Dobie's come, I just bought a Dobie this week when they bought figs. So funny. So did I. Not an investment advice. Not an investment advice, but I was like, they bought fig ones.

1:30:49Okay, so here's my theory on this. They bought Figma in tanked, and I was like, why did people hate this? And they're like, oh no, Adobe is admitting defeat, and that they can't innovate in house. And to me, I look at it like Adobe has customer channel, and it was foretold five plus years ago that they were not going to build the next Figma.

1:31:12Like that would be a full rewrite of their entire software stack. So buying the thing, even though they paid a tremendous premium, 50X revenue multiple because of the network effects that Figma has, and obviously all the product stuff. But if they can get that through Adobe's channel, like I think that is an absolute win-win acquisition. And all these people that are like, oh, they're gonna ruin it, they're gonna kill Figma. No, they're not. That's why they paid $20 billion for it and have a gigantic bonus for Dylan to stay on board.

1:31:41Yes, they're taking a YouTube approach. I think everybody in M&A knows now. Yeah, like what's app? What's app? 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 concerned for Adobe if they didn't buy fake. 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. Yep. You just discounted the right move. Fantastic. It would be like, people are like, oh, you know, the Warriors signed Kevin Durant. And you know, we're going to lower them. We're lowering the cost. But they paid a lot to get them on the team. So yeah, and oh, you know what, we're going to lower the cost of the tickets. So okay, I'll buy.

1:32:40or they're lowering the odds in Vegas. It's like, wait, why are you lowering the odds? They're odds increased. I'll place that bad. So it's obviously bad. And then there's, oh, that's leftist Canva. And Melanie's awesome. Totally different thing. But yeah, and they have a free Canva already. And what if there's always the internal people who are penciling out that spreadsheet?

1:33:03There's a group of MBAs who penciled out that spreadsheet with Figma, no offense to MBAs or 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.

1:33:30we would get this many more Figma users, but we know when we get Figma users, then we get non-designers to pay for it. So right now Adobe has a bunch of designers paying. But they may not have all the non-designers in their business. Only designers pay Adobe. Well, no, they have marketing cloud, but that's a totally different set. But when you look at Figma, I got a Figma account. People who are giving feedback on designs.

1:33:57The 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, Legos 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 it, because that's where everybody is. And that's one of the things you'd have with Figma. It's like, everybody's gonna have a Figma cast on it. Yeah. Just to watch.

1:34:27the product team build the product and put a comment in and who cares if it's a hundred 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 viral identity, I think Saks made this point on all end two weeks ago, which was like, if they're paying 50X now and the company's growing, okay, they're paying 20X next year. 25X, who cares? You're seeing such a high growth company. And then I was just thinking, well, somebody's got a theory there and...

1:35:11When I sold Weblogs to AOL, people were like, oh my god, these people are idiots. They gave $30 million to, you know, for Weblogs Inc. They weren't got $200K in revenue. But they didn't realize was AOL, autos, AOL tech, AOL lifestyle. Those were sold out at like a $90 RPM revenue per 1,000 pages. The ads were different CPMs. So then they would put an Engaget or an autoblog story or blogging baby or whatever other blog we had on the homepage of AOL.

1:35:41And 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 $100,000 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 post.

1:36:08because we said, well, people can write four an hour, so it's 20 bucks an hour, and it's $6 minimum wage. It means that's God. If you hear some media game, it's changed so much. And that I was like, okay. You guys were doing 200K annual revenue. We had done 200K to date. Holy crap. Over the 18 months. What is it? I mean, now, like, the world we're in today. People went to the multiple and they were like, jay cows is robbed. And I was like, okay, $30 million. I was like, what do you think? Like, here's a, I was like, an 88 five years later, and that's the best.

1:36:38The best M&A is when you look like you robbed the bank, and then five years later, it looks like you robbed the founder. YouTube, Instagram, Figma will be in this category. Yeah, when they put Instagram, they're like, 30 people work with this company, and they gave them a billion dollars. You guys are morons, and now it's $150. It's a thought exercise question, obviously irrelevant because you don't monetize it. What do you think the enterprise value of all in is? Well, it would do $10 million in...

1:37:07When I was at the code conference, a lot of people have been trying to buy it or put it as part of their network obviously which would kill it. Yeah, 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 Shema pulled me aside at some point and was like hey, Shema like just we're friends like yeah, you're all your next fund won't be bigger. Hey dumbass Yeah, 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 Shema 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

1:37:45The pot 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. You guys just started doing that. You talked about his back. You know, uh, I, he did he just, uh, found a target for it. Yeah. Uh, Jamal talked about, um, the, uh, healthcare company, which is, I mean, we wanted to talk about that because Jamal and I both agree, like, maybe we're, maybe, like we're definitely over prescribing.

1:38:13these drugs for ADHD and attention drugs. And adults are taking too many. I think that's not disputable. I think all science is showing that. So to make software, that could help kids with ADHD is like noble. But I think people want to hear us explain our bets. So 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?

1:38:40But it was the number one tech event of the year. Right. Right. So, you know, I'm kind of bummed that, you know, Freeberg's a little bit of a blocker for it, but I might turn him around and we'll have a vote, maybe a little bit. Let's do it again on the other 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? Yep. 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 value. Code Conference is done. Yeah, they need a new host.

1:39:07That's crazy. Oh, good. Like, it's such a value. No, I talked to Bankoff about it and he's been very public. You know, Cara 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 Cara 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.

1:39:28Bob 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 sugar and a 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, it's 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 car swisher like moving on but Jim said he's gonna keep doing it and you know, it's probably a small list of people who could actually host that credibly, you know

1:39:57Very small list. Which you're definitely on. I am? You think? How could you not be on? I mean, I'm not even saying that to make you feel like... No, joking. I'm pushing a little bit for this issue. Okay, okay. You're joking about being humble. But if it's not, I'm trying to joke on you. But anyway, that kind of prestige, it seems like Friedberg would want to do it. It seemed more like the thing he was averse to is the like... Yeah, I mean, whatever the issue is, we've had our issues. We all have issues. But I think there's basically two possibilities for all in Summit.

1:40:27I'm going to present it to the boys and say, like, here's the plan. Yes or no. And we agree. We'll put it to a vote. So we put it to a vote. If three of us want to do it, we'll do it. And if two of us want to do it, then we can't. And if I already, FreeBurger, I 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 said, great. So I'll do it with a different name.

1:40:54if they don't want to do it, and the fans can decide if they want to come or not and partially and, partially and, exactly. So, you know, it's up to the boys. They want to do it, but it was like a pretty great success. You already have Collins. Yeah. Well, yeah, I started doing a, I started doing a call in show called After All In for the last two episodes where I took calls about the last episode of all. Just to support David, because I don't think people remember how great that...

1:41:19app is. It really made great progress. I want to be supportive of him and I have a small investment in it. Very meaningful. On the one hand, this is ridiculous sale on the other hand. It might be ridiculous so 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.

1:41:42Like if Chimoff or Sachs or I or Freeberg were to get but one more deal out of it and it's an Uber right the economic value is nine figures Right possibly 10, you know like so that's the thing like I think like man Weblogs like you were doing 200k revenue you sold it for 30 million pretty great Take away, 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, you know, I love doing pods. This week in startups is a juggernaut as well, you know, that would offer 10 years. And all in is. What is that like to quarter million listeners or something? Yeah, something that ran. Yeah. I mean, it's hundreds of thousands per episode. And yeah, it's very niche podcast. You know, I'm not trying to make it all in. I'm trying to make it for founders. And so, you know, if

1:42:29in order to make it bigger, it have to be worse for founders. Right. And that's what we thought. It's like what we think about with archaer. I want capital allocators to listen to it and I'm not trying to move up the rankings. I don't mind, you know, hanging.

1:42:42with, you know, all in being number one in tech and then hanging out with you guys at, you know, slumming it at six to 15 with you guys and the rankings. It's like, that's where we belong. Look, I got number one on board. 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 then you try. If you want to appeal to everybody, like read the Bible, like that's right.

1:43:05If you go to the, this is the big, big, big guy. He 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 lips. 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 ranking. So, I mean, or do a daily news program for 20 minutes. Like, that's not what I want to do. I want to talk for an hour or three.

1:43:33About deep topics in founders and I feel like it's underappreciated how much that's the playbook that should be the next Taylor Swift type episode that we do Yeah, I know for sure the playbook I literally took notes for it King of all media. Do you know him?

1:43:51I have never met him. I'm left 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's shock, shock stuff. But he and his later years became a great interview, a great interviewer. He really refined his technique. I really appreciate that about him. And he created characters. Sound familiar? Yup. He branded them. Yup. He showcased them. The whack pack, you know, all this stuff. Did he ever do an event?

1:44:14He used to do live events. He did the U.S. open stores, and then he would do Howard Stern's 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 played tennis against Bababooie, but I mean, he got 10,000 people to show up and buy tickets to a tennis match that they pumped up, you know, like for whatever number of months. I remember this for my childhood. And then he did his books, which were phenomenal. He did a movie.

1:44:41He did TV shows, so he's done a lot of stuff. And I'm just starting the process of doing a reality show right now. Oh, literally gonna do it. Are you really? Yeah, I mean, I don't know where the besties are. That's me. Besties don't want to do it. They don't have time for it. I mean, there was talk of like maybe all in, you know, kind of going onto one of those services like people had reached out like, hey, with this work, you know, it's a lot more work though. Well, you know, we would have to show up in a location. We'd have to do it weekly.

1:45:11You know, there'd be some formats, some shiny floor, whatever. It's a different beast. I don't think they have the time for it if I'm being honest. But for me, I would like to do a reality show in the Gordon Ramsay kind of vein, you know, where I'm helping founders. I think it'd be great for reach.

1:45:27I had done a reality TV show with NBC. And the wine scene corporation. Oh, wow. Yeah, and it didn't make it on air, but I have the... You should be a shark tit judge. I had been, they had reached out. Before Marcona, I had reached out early on when it was Dragon's Den. Right? Before when they were gonna bring it here. So when it was Dragon's Den, they had reached out early, but I wasn't very successful back then. I wish, but you know, I think now I think...

1:45:52I 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, reality TV folks reached out, I think in part because all of them were doing so well. Would founders and companies feel comfortable? Like I feel like 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 have been. 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.

1:46:38But what was really good was really about, you know, me incubating companies. And they spent like $400, $500,000 doing the pilot. It was really good. And it would have been a big head. Did it get canceled because of the hard work? Yeah, because of the hard work. Wow. So they were just like anything that was in his company. And all the IP is dead because he's...

1:46:56Monster and so anything associated with it, but you got to remember he did project runway So he had some of these giant shows people don't know that about that and so I forgot Yeah, that had the TWC at the beginning so you know, I just and you see you know, I'm I NBC bought the show in the room loved it and did the pilot came close and Shema was on that episode actually did the pilot. Oh my god My VCE friend who came in and it was my VCE friend. It's no it's hilarious But I'm excited to do it if it works out it works out if it doesn't you know no skin off my back but I like the media space and then you know I this is the thing I'm choosing to do media because I get joy out of it. I'm 51 now I'll be gone soon like well you know

1:47:43You never know. And, you know, if I had two friends. I have two friends who died young. And I'm just like, 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.

1:47:56I'm not going for max dollars. 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, you're probably going to play now. We're like, literally not in the top 10. What is more money than to do? Like, you know, you know, you get a flame like, like, you want to understand my life. Like, it is ridiculous and charmed. Like, I can do whatever I want. I have enough money to do it. I'm not my kids are fine. I can have whatever I want. I don't.

1:48:20care about a third home. I have a ski house. I have my regular house. It's good. I'm good. My kids have their college days for that. Like 100%. I literally do not care about my money. Do you feel like that's a demon that you fight is like any alert 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 recognized me for what I do. I got all that.

1:48:46It literally does not even come up my radar to have more money as the last thing I'm thinking about. I do want to be the greatest investor of all time. To me, that's meaningful. I know I'm Mount Rushmore for Angels. I want to be Mount Rushmore for all investors. When you guys do your thing in 10, 20 years, it's like, okay, here's Doug Leoni and Moritz. Here's John Doar, here's Gurley.

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1:50:23When you guys were having the conversation in 20 years and I'm gone or I'm retired and you're saying mountain you were tiring. Yeah, that was possible. I met Don Valentine when they were like, you know, he was not active at the festival when I pitched Mahalo. He was in the room. He came up. I talked to him. He was, oh, he was still hanging out. Yeah, yeah, like why retire? He was just awesome. But you know, if you had that conversation right now about Mount Rushmore.

1:50:48Like you got a you okay, so who's it? Who's on your mind? Well, I mean you got to have done Valentine. Yeah, right? That's not possible But how are you scoping it? So you probably need Paul Graham to well, yeah, I mean you got Paul Graham is in the running for sure But that's like a number of startups, but there's a lot of big ones in there You have big impacts of programs definitely running but okay, so do you go with John doors in there along with so if you're doing firms is a lot easier because you get post law door and Perkins, Tom Perkins, you get the three of them at once. You do Sequoia, you know? People forget. When we're close, let's spend a decade at Klein and Perkins with John Doerring. Yeah, and you had, yeah, so, I mean, you look at that firm, it's like that's like the OKC with like James Hardin, you know, whatever. But then you have Doug Leoni, Mike Moritz, and Matt Tine.

1:51:41rule off. Yeah, we've been all them there. Those 30 years, and it's like, well, that's Mount Rushmore, right? So it's a Mount Rushmore of Mount Rushmore is kind of how you might look at it. You definitely have to have. We just did Benchmark. You gotta have the FAB for the FAB for error. The FAB for error of Benchmark was truly something special. Yeah, sorry. I mean, it's kind of like, it kind of builds itself the Mount Rushmore right now, right? It's going to be Sequoia Cliner, Benchmark. And then we're like, We're gonna have a big debate on the fourth arm, right? Yeah. Like, is it, what just depends how wide we're willing to scope it? Is it like traditional series A type venture firms or is it? I mean, it's an angelist novel. Right. Yeah. That's how the huge impact is. Do you put my C in there? Do you put? YC or tech stars? Both have a huge impact. Do you put, um, you know, uh, what else could be in there? That's just... You could argue for a founder's phone. You could say YC and tech stars. You have the Favid's phone really different things on the way.

1:52:35What 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 returns. Yeah. But tech stars, I think, was a little before Y-combinator. But anyway, you definitely have Y-combinators in the running for that four-spot, I guess. And then who else would you put in there? Masa.

1:52:53Oh, that's not beta. Well, no, I mean, but in that maybe I don't know depending on Excel would be in the running. It's sure. It's wrong. I think the way you kind of have to define it, which is unfortunate because it means that it's going to be a long ass time before your firm hits Mount Rushmore is three successful generational transitions where each of the generations would have been on Mount Rushmore. All right, so then let's just do this instead of Mount Rushmore.

1:53:19because 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 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. 24 AD Sand Hill Road is a very special building. It was the for thought power point. The quadrice complex. Quadrice complex. Yeah. Office. Then it was Microsoft Silicon Web. For people who want to shit about this. Oh, no. This is the end right now. This is the end right now. This is the end right now. This is the end right now. This is the end right now. This is the end right now. This is the end right now. This is the end right now. This is the end right now.

1:54:07Sebastian, who wrote the parallels. Yeah, yeah, yeah. You guys have taken this way too seriously. It's not bad. But then we're like a lone villain in David's house. TBI. TBI, Meryl Pickard. TBI. That's a good deal. Wow. I guess capital, benchmark capital.

1:54:21Shasta 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 at least just the museum. The whole fame. A whole fame. A whole fame is something we should wrap right on. We should just do it. Fuck it. We'll just do it like we'll just do it like every where we induct somebody. We'll get up there the three of us and be like yeah, yeah, yeah, yeah. This year we're inducting There should actually be a whole thing. We can totally do this. We can't know how like this is hilarious. You know, Cooper's town. No, there is a, what do you call it? There, it'd be our Cooper's town. Yeah, there is a history exam, but that's for the PC, which is totally valid. That's not for capital allocators. It's not for people. Like, yeah, there should be a whole of fame. And do we, like, do we might as less style ask people for the real hard truth numbers? No, no, no, it's about impact. You have to decide the three of us. We decide. It has to be impact on the game. Does the NGCA have like a lifetime achievement?

1:55:12It's about impact legacy, like the intent of the person. This is why Paul Graham would be like, you know, first ballot. This is why. Who are the first ballot? Entrance so obvious. We've already talked about it. We already talked about it. Those are all first valid. Do we have anybody who we haven't talked about or who's not obvious, but would be a first pal? Yeah, I was right. If you're under 20 years, you're not like just like let's wait to your 25 years in. Yeah, just like sports hall of fame. So you gotta have a yeah, you gotta be you're not playing in the league anymore. So programs 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.

1:55:58And just in terms of like, it's internal. They're not separate companies, but like capital allocating, lower KC, lower KC, they've been creating a placing batch. But you're right, Jeff Bezos is probably the most successful angel of all time. Yeah, I mean, if you just did it on top of me. Yeah, and on, you know, when you're looking at it, I think you gotta look at impact.

1:56:16Impact on a game legacy. So he's Carmelo Anthony, Hall of Fame, of course he is, but he didn't win a ring, but he's Carmelo Anthony, right? Or Charles Barkley, he didn't win a ring, but... Okay, so then we got Arthur Rock. You got to look at the founding father type. Of course, of course, yeah, that's no doubt. I mean, that's like going back to Bob Coosie or whatever, going back to some really people who built the league kind of situation before it became the league, right? So you got the league and you got the people before the league, you got people in the league, you got these generational shit right here.

1:56:45of Patrick Ewing. So I think like, you look at girly, like he's part of that Patrick Ewing generation, right? That's the theme of life you want, Charles Barkley generation. You start talking about founder's fund or YC or angelist, like, okay, now you're talking about more modern era. Still going, modern era, after 2000. But if you started before 2000, it's a different group. Do you know what we haven't talked about in recent horror? What's in this conversation?

1:57:09No, impact on the game there, they're in. I mean, I just feel like it's gratuitous. It's just like raising $10 billion, three funds a year. I want to see what happens with the crypto stuff. I think they're just an index adventure.

1:57:27I 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. More ambition? Yeah. It's more ambition than soulful. But there should be a JP Morgan or Goldman Sachs of Silicon Valley. Should they be? I don't know. Yeah. Why does Goldman Sachs manage the money of entrepreneurs? I just feel it's too... Okay, fine. But I just feel like it's...

1:57:53It's too, it's like too premeditated and less soulful. I feel like it's a soulful business where like your intentionality and your relationship with the founders really matter. It's not the craft. I mean, it's like the literally interfaces of it. It's industrialization. It's the industrialization of it. It's the factorization of it. And listen.

1:58:13I'm sure it'll be very successful at the end of the day and all the returns will be great except for the crypto stuff. Well, that'll be a meme reversion because like when you get the law of large numbers, you have meme reversion. Exactly. It will be meme reversion for sure. I mean, that was at some point they leaked a lot of their returns and they were like Eh, not fair. That was the 2015 thing. 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 going to, I think in the arc, it will not be comparable to Benchmark and Sequoia. And we, I mean, made a lot of hay at the fact that they had, uh, that they made $11 billion 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 in profit. Yeah, that's fair enough. Well, I mean, it's timing is everything. We'll see. I mean,

1:58:56It's interesting, too. I mean, having just done this benchmark episode, like the benchmark fun 7, one of if not the best institutional size fund of all time, just like unreal. Like even that, like the, the fluctuation in the marks on that fund, and it'll probably end up between 15, 25x maybe, but like, but it fluctuates up and down so much. Yeah, of course. I mean, it's we live in a very volatile time, right? Yeah, so.

1:59:21Yeah, 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 a... No, just we could just do it as like a dinner. We just literally have every year. We can just start in a restaurant, but you could get like a little hall. I'd 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 drop it. And he's got three people. And then people come up and say something about the person. And I think like we could do like

1:59:51The three who we would hope would be there, and then we'll have like we do it like the sports where you have the person who's being inducted chooses who indexed them. Sure. Oh, that's fun. In the buff does Doug or whoever does Moritz. Yeah. Yeah, yeah, but yeah, Parker does Moritz. Mike chooses who you know, you can have Larry Jason Calacanus come up and be like I read surging. Yeah, yeah, yeah, totally. Yeah, John Doer would ask Bezos. Yeah, maybe killer. It's killer idea. I mean, we just do Bezos. Yup. Doug and Mike. Yup. And then who would you want to know more in? Yes. We could do one in memorial. Exactly. Yeah. You know, whatever. It would be anti-climactic if the only part 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. Maybe four people a year. You have to think, how do you want to get to 25? So maybe it's

2:00:51You want to get to 25 to 50 over 10, 20 years, so yeah, maybe it's three a year. In order for this to feel good, I think you're right that it has to be about impact, not about returns. No, returns is like so.

2:01:02That would be like saying it's like album sold for the rock and hole full of fame. Right. There are people that be a very Andreessen Harrow, it's way to do it as well. That would be Andreessen. Oh, what's the total assets under management? You know what I'm saying? Okay, dude, we get it, yeah. Nickelback sold a lot of albums. Yeah, they're the Nickelback of that. Oh, I didn't read that. You said it. You said it. I wasn't talking about Andreessen. I can tell it's a Nickelback. Oh, God. Oh, God. I'm not saying that. I'm not saying that. I'm not saying that. Oh, boy.

2:01:29If you were to look at Ron Conway, did Ron Conway, who had a bigger impact? Ron Conway are in Dresden, I think it's a conversation. And if you, because Ron Conway, when I came into the industry, there was that one point, I was at the Crunchies, and Ron Conway, at one point, somebody said, hey, can everybody stand up who said Ron Conway invests in their company? And 100% off. And my mind was like, whoa, angel investing is cool. I mean, I wasn't an angel at the time.

2:01:59you know, long before I became a scout, but I always remember that moment when like a hundred people stood up. It was the scout program. Is that what like put you in business as an angel? The scout was what put me in business. What happened was I had... Was your Uber investment you personally or was that a Sequoias? That was Sequoias, man. And we were like rule off and I were trying to figure out.

2:02:20Do we let people know we're doing this or not? It was like a big controversy at the time. Right. We want to keep the stealthy, but I mean Travis knew, but you know, it was it was a pretty great deal. You know, it was like, you know, at the time they carry 50 50 50 at the time. Yeah, they dropped it down after that. I bet every time I see Doug Mione's like 50 and they had 30% 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. Doug, they're so classy. Doug always made a joke. I would always make a joke. I was like, 50% carry. Oh, god. We get 30. You get 50. It was just funny. We get 30. We get a lot of it. Pretty funny. 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 might have.

2:03:12Also, I was just thinking about humanity, and I don't mean to make it heavy, but these companies do move the human species forward as... Look at Elon. 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, if they should even build this company. And I think the capital allocator's really come in and say, here's some fuel. You know, here, go fight that war, you know.

2:03:42It's fuel and it's belief, too. I mean, like, what your story about calm is not uncommon, I think, amongst founders. Oh, my God. I mean, look at, I mean, the stories about Don Valentine and Atari and other places where he was a Cisco. He'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, drift toward the end of the episode here?

2:04:05That's your line, that's your favorite line. Drift. That's the band signature line. I can call us here to the end of this. Drift starts the MV. Is this a good time? Is this different enough from our normal show? Should we do this? What shall we change? Yeah, do you like this? I think a casual glass of wine and just, you know, if you have friends of the pod and you want to go deep and talk about them in a more casual way, sure. Yeah, I mean, I think it's a great way to just have somebody on again.

2:04:33You know, so if you profile something like I forgot that I had you had done like the first episode with me and that was more about my career and more details and so I'm sorry to tell stories over again It's like let's talk about some other stuff, right? Yeah, so I think it's a different our audience was why I like the side of the format well, but what we you know like Lex has done so great with his show Yeah, but but those type of conversation, but I feel like that's more What's the right word?

2:05:00Our shows are about the business of tech. You know, his is intellectual about that. I don't know why he's in the tech, but I like the format. And like Kevin Rose used to do with 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. I want to see him say stole. I think, you know, inspired by. Yeah. So Lex is clearly inspired by Joe. And Joe was, Joe was in the running to replace Jackie Martling.

2:05:30on the Howard Stern trip, people don't know this. So he was very enamored with Stern. And he wanted to be Stern, I think, and he eventually has supplanted so in a way. Yeah, he did become Stern. Yeah, it did become Stern, and so good on him, yeah. Right down to the serious Spotify, like, right down to it. Well, yeah, doing a platform. Yeah, doing a platform. Which is what?

2:05:54Stern did. Stern had multiple platform deals. He did syndication first, then he did the Sirius XM1 because it was a new platform and he built the platform. He used his number one show to build their platform, right, which is I think what yeah, which this but actually bring it all the way to full circle back to Charlie Rose. Like yeah, he was like a, you know, business. And he needed more than business, but like he would have a culture business. Anybody in New York, because New York everybody in New York was pretty fucking interesting. Yeah. Yeah. You know, he could have somebody from Wall Street, a publisher, an author. Yeah.

2:06:22somebody who does films, you know, he would have, like, Spike Lee on it, you know, he'd have Woody Allen on, he would have, you know, any actress on who was doing something interesting, any novelist, Margaret Atwood, anybody, which was coming through New York on a press tour, you know, you would do your press tour, and then you would just go chill with Charlie, and you would get to do something long for him, you know. It was like a little, like, sort of, more jazzy, you know, like, acoustic. So I like this format for you guys. Do you listen to Smart List at all?

2:06:50Do you know about that show? I have listened to one or two episodes. It's Bateman, Will, Arnet, Arnet, and then somebody else. Yeah, the guy from Will and Grace Sean. I don't know who that person is, but they bring on a surprise guest each time. And the other people don't know. Yes. So they're not prepared. Yes. And it's like, it's like Katie Perry, it's like Chris Pratt. Yes, become a big deal. I kind of want to do that of tech.

2:07:14But like, you would, I don't know who the one of us is bringing somebody back. You guys are not going to, you can't make, you got to know the person's background much better. But they all have a very certain charisma with them. That R&D doesn't. Yeah. But maybe it doesn't have to be surprised as much as like, well, the, the other thing is that even though they have guests, the show is actually about them, the guest is a prop.

2:07:37In 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. So I see it on iTunes. I 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. So why not bake the ads in and put them all? There's some NBA that's run the numbers that says it's more valuable if it's driving new subscribers. I guess that's it. I guess that's it. Oh guess you know what? They want to be able to have those new subscribers when they go renegotiate with the music. So they're doing audiobooks too now. That's the next piece. Yeah, that was the next piece. Yeah, they're doing audiobooks one-off purchases. Smart. I mean audio is great.

2:08:25It's getting really hot in here. It's getting so hot. We're in like a sauna, a new... Yeah. David's new house. David just moved. David's got a new empty house. No way. It's sort of like the shining. There's no furniture. We just find this room. This is all from Craigslist, all of it literally in the last two days. That explains the smell. All right. You could have, I mean listen, you're rich, dude. Just go on. Oh my god. We can't. I'll be Jason Calecadas. Oh, come on, man. I know those fees. Oh my god. I love Craigslist. I love Craigslist. I love it.

2:08:59You buy used furniture on Craigslist. All the time. I do not buy any furniture. That's kind of stuff. I bought a temporary couch. It's the thrill of the- It was not good. You're going to get robbed. Don't do it. It's too crazy. Craig, Newmarket, I love you. All right. With that, that, our thank you to Vanta. Oh, Vanta.com slash acquired.

2:09:22Are thank you also you don't know who the other sponsors are because we haven't we don't for them like with you because we like we felt very strongly that it was you know we wanted to make their use of your time. I love reading that you can't I mean we want to read our Brex ad.

2:09:35I don't sponsor my pods some now. Brex, maybe they have, I don't know. There's also a lot of ad-libbing in it. Brex, Brex, Brex. I know about 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.

2:09:58than if they screw up, you can turn it off or something. They jump pre-approved some budgets. You don't want people jumping the fans out on crazy. All the listeners know because they heard it like an hour ago. They're very familiar. Oh, that's in here. So that's Brax. And then use the promo code to us. We share this last sponsor. These are great folks. These are like dear friends and geniuses and rack contours. Masterworks?

2:10:24No, no, no. Think smaller but bigger. Literally small. Oh, you got to get like secretly huge. Tiny. Oh, tiny of course. Yes, they're buying companies. Yeah, buying companies. They're doing a good job. Yes, they're creating like the birch year of the internet. And can you imagine a better time?

2:10:46to get the monkey off your back of venture capital. And some of your company. Secure the bag. Secure the bag. Let's go. Secure the bag. Let's go, man. Trust me, if you haven't secured the bag yet, it's a wonderful experience, man. There's nothing like getting home with the bag. You get that tiny bag. Get that AOL weblogs. Oh, man. Let me tell you something. I'll tell you the story. What did you do when you secured the bag? I'll tell you what happened. I got this funny story. I'm in my office and I got Bank of America.

2:11:15And I got like low thousands of dollars in my bank in America. I got an American Express car with 10 negative 10 on it and a visa with negative five or 10 on it. And I'm sitting there and they're like, oh, wires are good. You know the B.D. people are a well and so I'm like hitting refresh. Yeah. On the thing. This is 10,000 refresh. I'm hitting refresh. I'm hitting refresh. And then ping, ping, ping, ping, ping.

2:11:40you know, all the numbers come in for the whole, you know, amount. And you own most of web blogs. Brian and I were equal partners. Then we had Peter Rojas had some ownership and then Mark Cuban was our big investor. And by big investor, he put 300K and for 5%. So that was a great outcome for him. Or more, maybe one 10%. I think I'm 10%. Anyway, long story short, my wife comes in. She said, you okay? And I said, what? She said, are you crying?

2:12:08And I reached out 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 says, why are you crying? And I said, my family will never have to worry about money again. Because I spent my whole life worrying about money. My dad had lost the business. It was a very cathartic thing for me. And I think people who are already rich, or maybe who come for means, just they don't understand the concept of living with the fear.

2:12:35of being broke and in debt all the time. And then when you have the bag, you secure that tiny bag. It's a tiny bag. But it's still with diamonds and cash. You just open it up and say, thank you, tiny. Thank you, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny, you're a tiny

2:13:00and tell him that it's like just know that tiny little bit. Tell him that Ben David and Jason. You can mention Jason, yeah. You should have did by a one touch express machine and bought a Jura, one touch express machine, which at the time was like two grand. And I was like, this is unbelievable. That I tried to buy a Ferrari. They wouldn't sell it to me in Beverly Hills.

2:13:22You were like no new money or something. What's that? Yeah, basically I went in there and they're like, oh yeah, what are you? I like to buy a Ferrari today in the 430 and they're like, oh, we don't have any available. And I was like, okay, can I put myself in the way? We're not taking national weight list. So I said this guy can I ask, what do you do here? He's like, we sell Ferrari's. I'm like, to who? This is part of their strategy. It's part of the strategy. It's part of the strategy. I don't like it. I don't like it. But they don't sell the Ferrari's to build these things. We're not putting any British list. I was like, well, how long is the weight list? He's like,

2:13:51I was like, okay. I was like, I'm a cash buyer. I was like, everybody's a cash buyer. I'm like, okay. Can I ask you a question then? He's like, sure, come into my office with like a espresso. He wants some pelagrino. I was like, no, I'm good. He wants some pelagrino. Like when I do offer me a pelagrino espresso, and I was like, I was like, I have the same one touch. Sure. I'm like, it's like a tie, guys. I was like, I don't mean to be rude, but.

2:14:16What do you do here all day? He's like, well, we deliver the cars and we service them and we sell used cars and 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, no, the one I'm looking at, the four of 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.

2:14:37Well, that goes for $230,000 or whatever. And so, yeah, what do you want for? He's like 300. And I was like, you're like the stickers. No, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no I just saw 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 too. I was like, well let me think about it and I laughed and then I was with my friend and I was like, and I had the rob report and it said like number one car was the Ferrari F-13 that turned the page of 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.

2:15:31There's something like that. I was like, let's go to the court. Let's go to the sheriff's office. I'm walking. There's Corvette's everywhere. The guy that 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 $5,000 off. I was like, yeah. So we'd go out on the 405 and we're driving the Corvette. And he's like, there's a Corvette son. You're going 70 miles an hour. I'm not selling this car to you unless you hit that gas much harder. And I said, okay.

2:16:00Punch it to a hundred miles per hour guys like yeah, how does that feel? I'm like great I come over the yellow convertible core about my wife's like what happened to the Ferrari I was like this thing only cost 65 grand it's like 70 and I got five grand and it's American baby and it's American and that was the car that I famously Was according to Glocker Robert Skolman myself in Elon when Elon got the first P1 of the Roadster. He was like, I got it. I was like, oh, let's meet in Bretwood and we were driving them. It was crazy. We were driving them along Sunset Boulevard. The spirited drive. The spirited drive along Sunset Boulevard and we did it like five times and five out of five times the Tesla just destroyed the Corvette. I was like, I'm doing something wrong and then we switched cars and I was like, nope.

2:16:51Electric is gonna be and this was the first one That you know first. Yeah, that was amazing the prototype at that's in space right now is the cherry red one that's the one that's the one the famous photo of me and Elon in front of with that That one's it, but there's a famous photo of the two of us you know in front of my quirk baton his P1 and I remember that night like it was yesterday because before the iPhone you realized like Robert Scobo was recording this on his Nokia you know these are the memories right like this is the journey that you've been on yeah this is the stuff you just will cherish forever my life is unbelievable I am so grateful for it and thanks for having me on the podcast

2:17:33Listeners, thank you so much acquired.fm slash slack come join us. We'd love your feedback. This is a new stick. Yeah, acquired.fm slash store. You can buy cool shirts. Shrack. Uh, slash jobs. Find your next one. Craigslist. Craigslist. You get a bunch of new ones. That's right. I get fired.fm slash David buys you some smelly furniture. My god, it is hot in here. All right. We got it. Let's go eat something. I don't know what we're going for here. Oh, so fun. Thank you so much. Of course.

2:18:02All right, listeners, we hope you enjoyed that very first acquired sessions with Jason Callicanis. It's a new format we're playing with. We would love your thoughts at acquiredfm.gmail.com or tweet at us at acquiredfm. And with that, listeners, we'll see you next time. We'll see you next time.