ACQ Sessions: Jason Calacanis

0:09 Wait with a magazine. Magazine, yeah. Yeah. Magazines was like the original platform for Wait are we st have we started? Silicon Alley this is the trick we've just been recording the whole time. Yeah, but all that stuff that you said beforehand that like is really juicy st I don't think we should put that in. No, definitely not. Definitely not. We don't want to tell people where the bodies are buried. Well cheers, boys. Cheers. Here we go. Is this the first one? This is the first in real life. But I think this is our Ninth, tenth together, something like that? A lot. Between the two pods, yeah, for sure.

0:41 Great to know you, boys. So this is the first acquired sessions. Acquired sessions. I feel like I should get out of a guitar here and just play some Dylan. This is 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. But uh Well like for folks like you who we know really well.

1:04 Yeah. Throw out the script. And just chop it up. And we just chop it up. David Rosenthal unplugged. Wow. Love it. Literally. All right listeners. Now is a great time to talk about a new partner of ours here on Acquired, Lagora.

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3:25 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 Lagora.com/slash acquired. And just tell'em that Ben and David sent you. So in the juicy stuff earlier, you mentioned Mahlo. Yeah. Can we just keep perhaps, like, referring to the juicy stuff as well. Yeah, we want to talk about that stuff. Yeah. Is Mahalo why you Started

3:52 Print to Well when I in the nineties, um I you know, I grew up in Brooklyn. Um My Dad. Had his bar. Uh seized by the Feds.

4:03 because he didn't pay his taxes during the Nineteen eighty seven crash. He became like he got behind. And uh the Fed showed up one day, and this was the maybe six weeks before I was set to go to college. And he said, Hey son I can't help you with college, good luck.

4:20 Uh and uh I might be going to jail so take care of your mom. So he was like really behind on his taxes and yeah, state liquor authority. They kinda take it serious. So feds come, shotguns, the whole thing, they seize the place, they seize everything in it, and uh I was like wow

4:37 I guess I'm going to school at night. And I'm gonna work during the day and I worked. uh fixing laser printers. And uh that was like a really good racket. The HP had just come out and Were you set to go to college somewhere else? Well that's another story, but I was set to go to Brooklyn College. I got into that. I had also taken the police exam to be a police officer. So my brother went into the force. And then I said, You know what?

4:59 I'm gonna see if I can go to college and make that work. So I'm gonna go to Brooklyn College. So I decided to work during the day and then I went to school four nights a week, six to nine PM, carried full credits, sixteen credits a semester. And uh I would work fixing laser printers all day. I was a bad student. Uh I was always that student who underperformed. I didn't find

5:20 great meaning in academics but I had a computer when I was in high school and I was more interested in playing with my three hundred board modem. So they make him a twelve hundred broad modem I'm a P C junior, so Okay. Kinda you know, like many people of that era, we were sort of set on a path because we were the first generation to have a computer at home.

5:38 Uh I actually had an Atari twenty six hundred 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, nineteen seventy six, nineteen seventy seven, and he had one of the first pongs in Brooklyn in his bar. So he must have cleaned up on that. Oh my God, it was crazy. Um And so we uh I I just got exposure to video games and computers and I was like wow, this is incredible. Like computers are gonna change everything. And then I happen to w hack some software. We used to

6:05 I ran a lot of scams. Uh but uh He told us about the the VHS. So VHS, Jason's Hot Tapes was technically my first business, but there was a side job I had which was cracking software, so we were We would make copies of like Chess Master and stuff like that and then sell them for ten bucks. And then we started like hacking and doing what was called phone freaking. W when you were doing this stuff, like It's you to be reasonably technical to do it. Not like the m you know, not like waziak technical, but like

6:31 You solder chip sometimes. We change Yeah, we put we to put memory in at that time, you had to like take the memory chips And put them in and then bend them over and stick them in. Did you ever think about like did did you consciously ever make a fork? where you were like, not tech media. And of course media about tech, but you're like, I'm not gonna be the guy

6:51 doing 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 Street and I used to hang out in the West Village or the East Village. There's like the cool places to hang out. And um Like a thing to do would be to go to Tower Records.

7:08 and look at the zine section. So there was a concept of a zine, which was short for magazine, but a zine was something you wrote with your friends. you printed it yourself at a photocopy store. It's like blogs before blogs. Blogs before blogs. And I created a zine. I was like, I'm gonna be a magazine publisher. So the first one I did was Cyber Surfer. which was about dial up magaz dial up services and CD ROMs. And I did it with my friend Brian Alve, uh whom you might have heard of in my career. We went to high school together. Weblogs? We did weblogs together. Yeah. So but in the early nineties I did. All that stuff. Yeah. Uh but anyway

7:45 Before that I did this mag I did that magazine and then I had met Fred I met Jerry Colonna. At uh Internet World, the first one. And he there was a Booth. That's right, when Jerry was a V C before he was like the VCO. And I think CMG like us. And so there was a Lycos booth.

8:04 And I had met this young lady at it and we hit it off and we're talking and then she introduced me to Jerry Clowner. And then I met Jerry Klona in an office no bigger than this room in on uh Union Square. And he said, listen, I'm leaving Likos, but I'm gonna start this acme ventures with my friend Fred. Um I want you to come um 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 gonna back them for their venture firm. This was nineteen ninety four, ninety five. This became flat iron. It became flat iron. They were half of it and Masioshi saw and soft bank was the other half. No way. So they wanted you to come like be a V C associate. Not a V C. Just to read business plans. So the deal was they would take me for sushi and pay me a thousand bucks. Wait, what do VC associates do besides just read business plans. Exactly. Well anyway, it was the thing. And so I had the magazine started Silicon Eye Reporter and they were pay me and so I read Uh about this um

8:52 Um 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 twenty four years old, I don't even know what V C is. That's where Flatiron made all their money. Yeah. Uh they were gonna invest anyway. Flatiron went with Jerry Kelowna then when Jerry decided he wanted to move to Colorado and just chill. Yeah. Um he had made enough money, I think. And Coach Founders.

9:15 Coach founders, I think. And yeah, maybe he had like uh I think he's been pretty public about it. Like I don't want to say a nervous breakdown, but a kind of like Maybe a fork in the road, like making a decision about what you want in your life kind of situation. He wrote that great book about it. Yeah, yeah, yeah. And so Jerry was a good mentor, but Fred actually became ultimately my my deep mentor uh at that time. And Uh, Fred said to me, Listen, you're doing Silicon Eye Reporter. You're writing about us. And the companies we're investing in.

9:40 And um You're doing stuff, which would you rather do? And I was like, I think I'll do the magazine. Uh this was before now it's like I do both. And now it's like I do both, or white choose. But just to back up to T Cities That sold the Yahoo for like three. And Flatiron was the main investor. Yeah, Flatiron maybe about five or ten percent of it. It was like a huge win for them. I mean Fred was on fire. For a near VC and Jerry they did pretty well.

10:03 How did that happen, right? Like I mean Silicon Valley was here, but they were in New York. Like what was going on? Well they have red herring in the bay outside in the bay, but I own New York and I had Silicon Arporter and then I started one called Digital Coast Reporter in LA. So I had two magazines, two conferences, two email newsletters

10:25 That's kinda King of New York, right? That grew that business to ten million dollars in revenue off my credit cards. Um and um Had a seventy five to a hundred people working for me when I was twenty seven years old and I didn't know anything about how to run a magazine, how to run answers, I taught myself everything. What your family think of this? Like

10:43 was pretty heady stuff because I wound up being on the cover of the New York Times on Charlie Rose and they wrote a feature story me about me for eight thousand words in the New Yorker. So anyway, it's a really cool time in New York because at that time You were either in media or finance or art. Publishing, it was like a spring I set and I was in publishing, but I was also in this new thing technology. And so

11:02 Everybody wanted in on that. It would be like the equivalent of crypto. Is today like at its peak where like and you were Satoshi or something. Like it was crazy to be the New York internet guy. Um Can I so we talked a lot a lot of this when we did our like big Jas like Empire of Jason Calcanus episode with you. So I want to like put this on pause. So people can go listen to that. You should. It's great. We get like the detailed

11:31 story of like weblogs inc and all that great stuff. And i you mentioned I want to like Take us from you're only as good as the you know, your greatest your your newest thing. Sure. Um'cause the last time we talked to you, you h were just starting all in. Hilarious. And like can we talk podcasting? Of course. I love it. Podcasting is like I think perhaps My greatest medium. What?

11:52 happened with all in. How did I I mean it's weird. It has it surpassed your wildest expectations? Um, I thought it would be something Chamath and I would do ten times. Yeah. So the the origin story is pretty simple. Um Chamoth.

12:08 Uh I knew because he was running ICQ. Jamath was running ICQ at AOL and I had sold my company AOL and Like the revolving door of the line is like Ted Leonis had this March to a billion Uh my Greek brother, a mentor, had this like march to a mil a billion.

12:27 Um off site. And so I went to this and I just sold Weblogs. Like a million AOL users. That's the the That was the idea. And with uh AOL and other assets they wanted to buy, they were gonna march to a billion users. Yeah it was like this crazy rallying car, and we had these t shirts march to a billion. So I go to that and I see Chamoff and I was like, Hey and he's like, Hey and we

12:49 introduce each other and we had known of each other and I was like, What are you doing here? He's like, I'm running I CQ into the ground, you know, I'm just writing it down every month it loses a million members or whatever. That's hilarious. And he's like, Yeah, but I'm anything I'm gonna go um I'm gonna go to the West Coast, I'm gonna go work at this V C or whatever. I was like, all right, nice seeing ya. Um, and so then when he was there, I was in LA Uh V C did he go work?'Cause at Face Mayfield. Mayfield for a year and then Sean Parker introduced him to uh um Zuck. And Zuck needed, you know, like a Chamoth. He needed like somebody who would just

13:22 He built the growth team and he's like I don't Th there is no equivalent of growth. There was that was the the idea of growth hacking didn't exist as a term until Chemoff did what he did. He said, Just find me the smartest people.

13:35 I'm hiring based on IQ. And I'm hiring based on desire to make a lot of money and be a beast. And he just went he went into beast mode because you know he was very hungry. Um anybody brothers from another movie. We're we're we're definitely, you know, both outsiders in Silicon Valley and um You know, I had Chamoff come on the pod. Between startups, that is. Uh, we listened to it. It was it's fun to go back to that moment. You know he you can see how he's not

14:04 Yeah, polish. He's not Chamoff. You know it's gregarious or whatever. He doesn't have the Laura on. No Laurel Piana. Was he in great shape or No. Not one of the picture. He was like a he was like a dork, you know? Like he but he was pre his basos pre uh yeah, whatever. He always was A poker player. He was playing Atlantic City, so he was

14:26 you know, like myself, an outsider who wanted to take risk and wanted to win. And um you know, confident, you know, even maybe more confident than both of us should be, but Um And so I kinda introduced Shamath to the world.

14:42 By convincing him to come on the pod, which he was like reluctant to do when he was at Facebook, but he did it after Facebook. So I kept asking him to come. He finally was in LA, he came on the pod. And then people I was like, really good on stage. Like he's he's funny, whatever. And so Which at this point you had an eye for because you're like of course. I mean one of the things when I was a podcaster in those early days, you know, talking about twelve years ago, whatever. is you know, I introduce a lot of the world, right? I introduce people to the world. Yeah. Oh yeah, it was eight two thousand eight, I guess, whatever. So I introduced a lot of people who were in tech. To the

15:14 Yeah, and it was only a couple thousand people. And then as now too, like You could be a great founder, you could be a great, you know, person in tech, but like that doesn't automatically make you a compelling No, of course not. No, I mean there I have my own theories about what makes for a great guest, but on the side for now. But um anyway, we we we start a friendship, we start playing cards together. Uh, we start hanging out. Yeah, trading notes kind of thing, and uh he's gonna start his venture firm. I'm a scout at Sequoia, all that stuff. We start playing and trading notes, and we just become great friends.

15:44 But then he was coming out of C N B C 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. It's like I wanna do a podcast with you. I was like, Yeah, you can come on the Swing Star Up any time. It's twice a week now. And which it's now five times. Six six minus plus I'll see. I'm gonna go I may go back down to five next year. It's a little much right now. Yeah, dude. You're I mean we'll come back to this, but you're killing yourself right now and you're on act three.

16:11 Yeah. I have more energy now than I I may I may have I I just this like coming out of the pandemic might have as much energy as I did when I was in my twenties. But for different reasons, different type of energy. Um anyway. Tremov calls me, you know, coming out of the studio. I don't know if it was in he was in New York or he was in the one market one in San Francisco here, but um he said, I'm gonna just pop with you. I said, Okay. And he said

16:35 Do a new part with it. Just me and you. We talk. I was like, Sure. He's like, What should we call when texting back and phone? I was like, We should call it all the time. This is twenty twenty. Yeah. It's like two years ago or whatever. And I said, Yeah, we should call it all in. Like we should come with a poker name. He's like, Yeah, great, like a raise or something. It's like all in. Because you would you'd been referring to this poker game on air on Twitter. Yeah, we talk about it once in a while, the poker game that doesn't exist. And Sky Dayton and I had a poker game with Brooke Hammerling, the famous PR person. at the code conference, which was the all things D conference before that for twenty years.

17:05 Then Shamatha had a poker game, Saks, I had hosted it floating. And putting all that together. Um Yeah, I'd refer to it many times in the pod, but try to you know keep it from becoming public. Uh but it was me, Bill Gurley. It's all public now. Mark Pinctis, right? Or maybe it used to come to the code one. Yeah. Um Which is another funny story. Um And uh lots of funny stories in my life. But anyway, um so then

17:31 The pandemic happens and we're like well. We gotta pump up on the point, we gotta pick these up. Anyway. I at some point I'll write a biography. Anyway, um Ten nine years. Uh third book. Anyway, the um Then we if we were The pandemic starts to happen like, Well, Sachs has some ideas about masks and then Freedberg has some ideas.

17:55 There was no besties originally, right? It was just you and the truth. Like Uh Freeberg and I weren't besties before all in. I mean we knew each other. We were friends, but not besties. I was besties with Saks and Chamath, and now Freeberg is a bestie. Um and But he he played in the game, obviously, and we had just started to have a developer friendship. But anyway that foursome kind of clicked, right? Pretty quickly. Um and I think

18:21 You know I was a really good interviewer. I'd studied interview techniques and really, you know, after doing a 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 them. And at the poker game, we break chops and I make jokes. Um and Chamot's a great host and very comfortable with each other. Uh And and Freeberg kinda joined that group and um

18:46 You clicked? And I think during the pandem and I I I thought maybe this last ten, twenty episodes. But during the pandemic, I think people wanted information and I realize like I think that's a thing I'll s I'll tell you I never expected to be

19:03 listening to David Sack's talk f coming from where he comes from politically and where I come from politically and going yeah. Mm, that is a good point. And that perspective is Like

19:14 so helpful in our polarized world today. Yeah. And you know, around the poker table, we all listen to each other and we're friends, but the world does not want us to be friends in s in some ways. The world wants us to be enemies and I kinda think about it like um you know best of enemies kind of situation. Like we debate specific things like uh Gorvadal and um Who's his adversary, yeah. Anyway, it's a great documentary about Gor Vidal and um William F. Buckley. They're just two public intellectuals. One was on the left, one was on the right. Uh and there's this documentary, Best of Enemies, in the sixties. they started debating like uh different convent political conventions and it was like the most compelling thing on T V. But they were like friends. Best of enemies, uh enemies. They weren't besties like Saxon I are, but you know Gor Vidal was just

20:02 He was gay. Um kind of closeted or quietly gay and on the left and Buckley was like a Sure is conservative and They went to blow sometimes on the show, like

20:13 At one point Buckley I think he called him like a sissy or something like really like derogatory as a gay man and the world didn't understand he was exactly gay. It was like sort of time period in the sixties where like Maybe some adults understood like Yeah, that's a gay man, but we don't say that's it. When they got into town yesterday, we were drive the Castro right here by and we we saw a naked guy in the castro and I was like oh naked guy in the cast. And Ben was like huge Jacked dude walking around and s and super sunny, so he's like just all like slick down sweat. Did he have his shoes on?

20:48 Was he wearing combat boots? Yeah. And then they usually carry a sarong. There was a big debate when I first moved up here because there was a number of folks who used to like to get a Starbucks and they had to like negotiate And they were like How about a sarong in Starbucks,'cause you're gonna sit right bare ass. And and for for context for You know, I I've explained this to Ben, but like this is a thing in the Castro in San Francisco. It's a cult it's like a

21:12 Now it's like you see it and it's like ah this is like a relic of the sixties, seventies. It actually was pretty awesome because David we're like driving up and David goes, Oh, a naked guy. It was the most like warm hearted. I had to um yeah adjust as well as a New Yorker because as a New Yorker, if somebody's naked That's a sign that if there's about to be some crazy person in a fight and police and chaos. And here it means like high fives and right ons. But you know, growing up in New York, like if somebody takes their clothes off on a public transportation or in a cafe. Like

21:44 People are getting a baseball bat and uh calling the police and like the 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. I that's one of the things I love about San Francisco. But anyway The pot's gotten very big. So you get the gang together and like Yeah, wh why do you think it works? Like Is it you think it was it's like the number one ish tech. Well in our business in our business it's number one, of course, but it's number it was number twenty eight last week.

22:09 Like in the girl on IG. You guys have transcended. Like this is more than it's like. It has nothing to do with tech anymore. It has nothing to do with finance or tech anymore. It is tipped over into colleges. I was at I was you know, skiing in Tahoe and I you know, I was with my kids and It's hard to get a table type situation. I was like Hey, I hate to be a past, but I see you're wrapping up.

22:29 And no pressure, but are you gonna be leaving soon?'Cause I'd love to camp out here and get your like stop busting my looked at me and she goes, Jake Al? And I was like, Have we met? And she's like No, I listen to your pod twice a week. I'm like, it's only on once I I listen to it twice. And I was like, Oh my God, that's so nice. She's like I was like, C are you in the industry? She's like, I'm a dentist. Yeah. We know. And I'm like

22:50 Your dentist in Renos, can I ask how you found out about she's like I don't know like She's like I deeply care about San Francisco politics. No, except how she had found it and this is, you know, during the pandemic situation, then that's when I realized it had crossed over. W there a moment for you Either you four or you where you were like Whoa this is Yeah, I've been

23:09 Um micro famous you know, micro celebrity multiple times in my career. But the dark Yeah, not for me, you know, and I got a lot of famous friends. Uh You know, I I'm used to getting recognized, I'm used to people taking pictures. What I'll say is like

23:23 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 twenty, you know, or ten. And they wanna take a selfie and it's

23:37 Yeah, it's just You know how podcasting is you you guys get recognized and It creates a level of intimacy p with people. If they're in the habit. Yes. Because you're hearing people every week. And then people become characters.

23:50 And I try to make everybody I I was you know, in in a show or I in all honesty, I did craft It was all in I was very premeditated in creating some character. I've never really talked about this. Yeah, yeah, this stuff. I crafted some character kind of arcs. I

24:07 The fights are all real. Trust me, there's nothing striped 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

24:20 the Sultan of Science. Right. And you know, Freeberg didn't even have a Twitter handle. Well there's zero followers. There's even a character of J. Cal on All In. Like there's the world's greatest moderator, sure. Yeah. I think more like J C Hal, the guy who lets himself be the punching bag because it plays for the show. A little bit.

24:39 Uh I'm not sure. If I'm being honest, I'd rather not be in the punching bag. Like they're like you're the poorest guy on the show. I'm like Do we need to point that out so often, guys? You're like not by much. Like I I'm feeling really good about myself. You don't have to point out that you all have more money than me and you Two of you have planes and I don't and it's it's okay with me. I I could have a plane, I guess. I could get one, but you care about the environment. Well, no, it's also like I don't want to waste a ton of money and you know whatever reason. Um But you do you do let yourself play that role of like

25:11 Like you have been enormously successful and you sort of let the role of J. Cal on the show be like. That guy who one day wants to be like us, maybe he'll maybe he'll make it. I actually Never wanted to play that actually. No, that was not that was just the boys breaking my chops, maybe. So maybe it's a little bit of like them.

25:30 wanting to uh you know maybe uh take the piss out of me a little bit, which is fine because you know, I give it as good as I can get it. But I think That's probably for them. You can ask them when they're on the pod. I think for them that's kind of the dis That's the one they can easily go to is I'm the poorest guy on the show, but like I've done okay. Like what I well maybe let's flip it, like for them Before all in

25:54 Maybe Tamoth had a little bit of a public. No, they were not famous. No market. They're all this is a new thing for each of them to hit this level of notoriety. It's not for me. What do you think for I mean we should ask them this, sure like If you were to speculate, Yeah. carry out that it's speculation. W what do you think for them All in has like

26:14 Done. Well, I mean for Friedberg. nobody knew who he was except if you worked at Google or you were in V C. Like he was very connected circles. What's that? Or Monsanto. Like he's very connected in those circles, but he was kind of under the radar guy. Um I think really by design. He didn't have any desire to

26:34 So I think it's probably the biggest adjustment for him. The the the increase in profile has certainly been the highest for him. And he's love. When I like jokingly said to people during the Q and A session at All and Summit. Uh you know, just say who your favorite bestie is, and then direct question. And it was like five in a row, Sultan of Science. And it was like, Oh my God, what have I done? Now I've created this monster. Yeah, and he

26:55 at the time like would barely show up for like you know, he would show up for two out of three episodes, he'd be busy. It wasn't a priority for him. Right. So I'd be like, all right, I'll put Brad Kirstener in, if you can't make it, I'll try to get Bill Gurley to show up or whoever Draymond. to fill in for him. You know, and it was always like I wonder if Freebird was show off, but he's actually really committed to the show now. Um for Saks, he was high profile, but Nobody really knew him as a Republican. So he kind of encloaked as a Republican on the show. Well I feel like he was also like

27:21 He was I Almost even more so than any, but He was high profile if you knew about the Paypal Mafia Munda, but he was like the least kind of public of the PayPal Mafia. PayPal Mafia, you would say

27:36 Elon Reed Hoffman Peter T. L. Max Levchen. Jeremy Sopelman, Chad Hurley. Rule off. Yeah.

27:46 And I guess Sachs should be somewhere in that. Strada. But I feel like being known. Being known. Yeah. Being known. But yeah, you know, and I I think Part of the reason this works is sacks. I think Saks have probably taken the brunt of the head of the pod. Yeah. Because

27:59 He is so passionate about, you know, a lot of topics that maybe are unpopular in the tech circle, so I do think like it's cost them deal float on the margins probably. I think there's probably I don't really margin. I wonder. I don't know. I'm just thinking like maybe there's somebody ascended. Because he's done all in in a way that's Yeah, sure. I'm trying to think if like

28:24 Would Is there a founder I 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 Chill's venture firm? 'Cause I'm so liberal. For sure there are. And those people feel that way about craft now. But for every one of those there's ten more who know about. So anyway I do think like he's joked that it's cost him deal flow. I don't know if it has. Um I think. The pod too. I think for peop for people.

28:51 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.

29:02 Yeah. You know, I've I I've been telling folks from the beginning, I'm an independent and a moderate I voted probably democratic. Three out of five times. Four to 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

29:20 Republicans or moderates, but I voted for Bloomberg. Giuliani when it was crazy. And Pataki, who were all Republicans. No, I wasn't, but I would have uh voted for him. Um I I like competent people and I supported Bloomberg for president, which got me a lot of flack. I don't understand why. People were very upset that I was for

29:43 Him instead of whoever's gonna be. Whatever it was. We we all think we are here in Silicon Valley, which is like social, uh liberal, physical conservative. Yeah. We're like everybody should be that, but we're the smallest of the four groups. Yes. It is a small group. I I um I I think I believe in competence and staying out of people's lives. So I

30:07 you know, it's very hard to know'cause and then even David I mean, this is I think when David and I fight on the pod, which some people love and I think some people probably turn the pot off when that happens and they don't like it. Um, and certainly I the MAGA group was has no love lost for Jake Allen, I'll tell you that. Like my replies have been Really crazy. I mean, like brigade in the last couple of weeks. Nuts. Um it's funny, but it's also like

30:31 on the margins, like they can get a little scary, like they'll dox me sometimes and I you know, that's not fun. Um a a handful of times it's happened. Uh but You know, I had to tell David like David I I I'm not like

30:46 I don't actually listen to MS NBC and Rachel Maddow to get my information. Uh and by the way, your Pro choice. Pro gay marriage. Anti war. Yeah, he's the dove. And I I was like, Well, okay, if you if we wanna play this game I'm gonna just dub you David the dove. And now you're making me into chasing the hawk like

31:07 What are we talking about here? Like um but anyway, you know. Well just goes to show how silly the the coalition building is. Like it's totally exactly the the the two party system requires that if you feel very strongly about something, yeah, then you're not allowed to think independently about anything else. It's so crazy, you know, and I and I think what messes people up is the fact that I actually just think Donald Trump is a horrible human. Who you should do no business with, has no business being in any political office, and you know, it is just horrible on any number of levels. But I believe that

31:38 independent of his party, he's a Democrat, obviously. Yeah. And so like I would hate him as a Democrat or a Republican. So it's it's not personal and I I would I would love to Or it is personal with him, but it's very personal with the party. 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 I get it. Whatever. And I think so much.

32:06 of the human condition is like being a part of a community. And he for so many people is a symbol that means, Hey, all my friends and neighbors. We're we get to agree on something so that we all can find Togetherness in something. And for some people that's the flat earth, and for other people that's startups. And for some people it's It's a 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 and Or the new iPhone. Like I found myself ordering this phone and I love it and it's the i four fourteen pro and it's magic and whatever. But like

32:43 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 on like let me look at the image quality versus the old one because it really is pretty. It is pretty, but like I got to be part of a tribe. And like that is a thing that no matter what your tribe is That is so fun to be there on Tribe Day. And Tribe Week. I will say the thing I'm proud about the show, I think. is that it has

33:09 you know, through a lot of the trials and tribulations shown that you can be friends, disagree, learn from each other, and have a vibrant debate. Which is how we all grew up, I think. Uh when I say we, including you guys, but also specifically the Basties. w I want to be friends with people who I disagree with. I want to Debate stuff, right? And then people are

33:29 Like this guy Dean Preston in um It's like one of these supervisor series. Super idiot, like guy in San Francisco who like Um, you know, like won't let them build housing all the stuff. And he's like, You're just a conservative, blah blah blah and I was like You don't actually understand who I am. He's like, You're a conservative billionaire. I'm like Wrong?

33:45 On both accounts. That you remind the ladder. My besties remind me on the ladder. I'm working on it. Not trying to be a billionaire, thank you. All right, listeners, now is a great time to tell you about a longtime friend of the show, Vanta.

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35:24 We're huge fans of Vanta over here, and literally hundreds of acquired listeners have become Vanta customers at their companies over the years. So you can get$1,000 off Vanta at vanta.com slash acquired. That's V-A-N-T-A.com slash acquired for a thousand dollars off. And just tell'em. That Ben and David sent you. Another thing that's really fascinating to me about

35:46 All in. Yeah. Before all in, and maybe and still to a large extent, I feel like Silicon Valley has this weird relationship with money.

35:57 Like super weird relationship with money. Like You know, remember there's the whole thing about like Zuck drove like an accurate SBP. David Filo and Jerry Yang were driving their old cars to work. Like the cool thing, like you you could like make money and build a company but like you never want to like you never and be understanding. You guys I think are the first like Wait, like you're you guys like

36:21 What like we got a private jet, like that's fine. Like, you know. I mean listen, I I uh Uh, you know. Yeah, I believe in capitalism. I think it's great if people create jobs and if they get rewards for doing so, like

36:37 Fine. I uh the literally th the book I'm writ my second book right now I'm writing is about wealth and money and like But not like in my regard, but in a sort of like big picture societal regard. So I'm like literally been thinking about this topic a ton. And I think we worry a little bit too much about wealth. Creation. um, with like a small like outlier wealth creation and we we don't think enough about

36:59 inspiring people to create companies and learn and like the time I create the most controversies when I'm like I believe anybody can do it. And people are like, You're so wrong. And I'm like, Am I? Because I go on YouTube

37:14 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 in Stanford And Brown. is online for free. And I listen to macroeconomic classes and AI classes when I'm like it's ten o'clock at night and I'm doing my email, I'll just put one of those playlists on.

37:36 MIT open courseware and I'm like I can't believe I can take a course at MIT for free. Anytime I want. And then you you know Flip it, you can build a business there. Like

37:46 David Sunra over the Founders Podcast, like Mr. Beast, MKB H D, like the world. Nobody gave these guys permission. 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

38:07 Wait a second. We I could never figure out how a term sheet worked and nobody would share their term sheet and now there are a thousand videos and blog posts on how to negotiate your term sheet. The world is still unfair. I think I very I think the Key insight is like recognize that the world is unfair and actually what that is is a game on the field and figure out how to play the game on the field. But I mean it's never been more fair.

38:33 So The world is unfair. True statement. And in America. It's never been more fair.

38:39 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 U X 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 s entry salary for these things is like eighty K

38:56 So I I I find it's very weird in the world. I think there's like a group of people who want the world to be more unfair than it actually is because it makes them feel more virtuous signaling good. 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, so they

39:15 And they have to and it typically like is a certain I'll just leave it at that. Okay, can I so I'm gonna buy your passion. I teach founder university now. I have a course where I teach people for twelve weeks. Um or I should say have a team that teaches it. And I'm gonna actually teach it myself, uh, this next

39:31 cohort where I just teach people how to store companies. All right, let's plug it. How can they find out where it's university? That's it. There you go. Yeah. I mean it's basically it's free. You The way I did it was you apply. If you want to build a company, you Pay seven hundred bucks. If you go and you get to we twelve, we charge your Strike back, the card back, the seven hundred bucks.

39:49 If you don't come or if you don't have an excused absence if people miss something'cause of their kids or whatever, fine. But we just try to get people to complete it. N over ninety percent of people complete it. That's cool. So and then we're investing twenty five K in some of those folks to help them start their companies. People don't know all the work I'm doing, like quietly, but Like two hundred people go to this course now. Well maybe I have four hundred in the next cohort with the fourth cohort, we'll see. But

40:12 You know, like people can learn how to create companies. And they're like, No, they can't. And I'm like Yes they can. You have to have gone to Stanford. I'm like No, I've invested in three hundred and fifty companies like Maybe Five percent of the founders.

40:23 Major Sanford. Like no, that's just not it's patently false. Like you know s you have some confirmation bias. you're dealing with a data set from 10, 20 years ago. I get it. But I'm telling

40:35 On the streets. ground level truth. We all meet with founders all day. It's never been more diverse. It's never been more open. Nobody cares where you went to school. Nobody cares where you live anymore. Nobody cares where you live. They care about what you've built and your traction. Like it is

40:50 Post pandemic All people care about is like Show me your metrics. Showing the product. Show me your team.

40:56 What are your skills? Great, let's go. What's your growth rate? Basically become like as beautiful of a meritocracy as I've ever seen, man, you say the M word, it freaks people the fuck out. I'm like, why is it so scary for you that Silicon Valley is a meritocracy. And they're like,'Cause it's not and I'm like

41:14 It kinda is. Can I can I answer your question earlier of what why I think all in works? Yes. Alright, so I think you're the you've got the perfect storm of three things. Mm. The first thing is on this out there, by the way.

41:28 Most people you're counter positioned. Most people who attain that level of wealth. Crawl into a quiet hole and make sure no one knows. You're doing shows from boats and jets. Yeah. So there's like we've done one from a jet, but yeah, there was definitely two boats in the last two years. There are like in some peak moments of all in, it's like watching billions in real life. It's like you hear you hear Chemoff talk about this spread trade and you're like this guy's got a lot of money on that spread trade and like does he actually have a key insight here or is he bl and like there's there's this interesting intrigue there. So bucket one is like billionaire porn.

42:03 Yeah. Bucket two. Is uh by the research you guys do and and the folks that you each work with, because there's definitely researchers that seem to be involved. You bring things to the table they're like

42:16 Brand new insights. Mm-hmm. That art widely available yet. So I feel like I was learning things about covet nineteen. On all in.

42:26 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. Oh. All in, how many people touch an episode of All In? One. Producer neck, that's it. No, I mean but like the research the like the best new no I I I I'm pretty text files open on people's computers when they're talking.

42:55 Uh we have a docket with the notes, but that's mainly for me to queue it up. Like I just read the four or five bullet points so people know it. So I 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 document. Right. And um I I think Saks has some research help. I'm sure

43:15 Friedberg and Chemoth. read the stories or they're well read. 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 twenty meetings a week with founders, they're gonna tell you everything in the world. Yeah and you guys are young still, but you know, imagine you do that for twenty years. Like you're gonna get smart or you're journalist for twenty years, you're gonna get pretty

43:39 I wouldn't necessarily say smart, but you'll be informed. So 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. Certainly a huge inf I I will say the information edge compared to journalists. Having been a this is not a dig to my journalist friends, I was a journalist. I had seventy five people at the magazine. We were always trying to figure out from the principles what was going on.

44:06 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 Thirty five percent of a story.

44:17 And I know that's like probably triggering to a lot of journalists that they have that little information. You weren't on the inside. But you weren't on the inside. So when you're on the inside, you have a hundred percent, or even on the inside you might only have fifty percent depending. You get enough to run with and you feel like okay, now there's enough story here, let's do it. And like that's clearly not the whole story, but it's enough to put the piece together. You're you're trying and then over time, process journalism, as some people have dubbed it, you know, maybe the six or seven stories will tell the full story. Yeah. Which your third component? Really makes it successful. It's the thing that David and I took forever to realize works about acquired, which is relationship and charisma. Yes. Like people like having fun by listening to stuff. Sure. And so

44:57 Like If we can make history fun. Then people listen to four hours of us diving into stuff you would never read in a book. And you guys do that in spades. Like it's just so fun to, like I mean the fact that

45:14 You as a podcaster who makes elite content, like top one percent content, find it compelling. It's just Yeah, that's very um Listen every week. Don't miss it. Literally walking the baby up and down the hills, listening to the I mean I have people tell me they listen to it twice, they take notes. I'm like wow, that's great. Well anyway, I was very intentional with My role in it to step back. Uh and be like the point guard. Um, but you know, I'm a shooting guard too, so sometimes I will want to

45:44 shoot the ball and uh I can do both. I'm a combo girl. How did the um Freeberg host episode come about? So one one week you switched roles. Well he was like, I think this could be done better, this could be better and that person. Go ahead. And I just like sure, I'll just shoot. Like I

46:02 And You pass the rock and all I was like, Yeah, you wanna be great show us. And he he did a he did a solid job. But let's be honest, like. It's not showtime, that's for sure. Um like I don't think people are gonna go to watch him play point guard. I mean he did a serviceable job um and put that on his tombstone. No, I mean but he shines when I created science quarter for him to shine. I said, Bring me a science. He's like, Ah, you know, I don't know if I want to talk about politics. I was like, listen, Sachs wants to talk about current politics. I'm giving him his red meat. Here's your quinoa.

46:35 Come 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 and So good. You know, it was it was a distinct effort. I really wanted to make him shine, you know, and um it worked. You know, it worked because You see how engaged he is. Yeah. And what used to happen was, and fans know this, I'm not speaking out of school here, y you see it every episode, Saks would disengage during science and Quinoa Greenberg would disengage her in politics.

47:01 And what I've been trying to do is keep both of them involved. Yeah. When the other is doing stuff and Shamath and I are involved. That's a hard job. That's a that's a delicate. I studied uh 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

47:26 Uh do they help? And I actually looked at the interjections. And If you look at McLaughlin, have you d you guys did not grow up on McLaughlin. So the McLaughlin group was the the best Sunday morning show. And like it was so good, like SNL would parody McLaughlin. It probably had a million people watching it, but this guy McLaughlin was like

47:45 pretty cantankerous and if he didn't like what people would say, he'd be like, wrong. This is the answer, you know, like it and it became so competitive that You want to watch it. Yeah. Now What I didn't realize by adopting that would be that Sack's is the ultimate debater. And will fight like a dog until he wins.

48:04 Any debate, and so I may have pushed True uh uh 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.

48:18 And then the aud 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 way of job. I'm not real-time fact checking facts. And um so that is a delicate balance of like And then sometimes I'll ask questions.

48:32 Specifically'cause I know the audience doesn't know what You know, fair market value when they hear an acronym in me. So I'm like Explain that. Right. And I'll stop somebody now. I mean you're you're expanding the TAM to dentists. Like when that's correct. Thank you. So People are like, Oh, Jay Cow's an idiot. He doesn't know that term.

48:48 Or I say to somebody, can you unpack that? Can you explain that? Obviously you know that term my stuff. You were what the third or fourth investor in Uber? Yeah, like exactly. Well played. I think he's been in Robin Hood too. Like too? Wow, who knows? And I'm like, uh dude, like I'm asking that question on behalf of the audience. So when I'm moderating, as opposed to being an interviewer, or as opposed to 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.

49:21 And You know, in that role I'm acting on behalf of the audience and I get the sounds like He's going Chamat's going too fast. They don't know what the spread trade is. Let me pause.

49:32 Can you explain one more time or let me reflect back to you, is this what a spread trade is? And he's like almost the this And that's what I think has brought in, to your point, a lot of the dentist crowd. And having an intimate sense of where your audience's edges are is is a really important role there. Like when you have guests on I'm always trying to catch

49:51 Yes. Wh where where do they just go slightly too deep and I need to pull'em up so that we Yeah and and and you know Podcasting is about going deep. So you it is really an art. Like do you want to stop somebody when they're going down this like crazy rabbit hole. And that well, they're going down some rabbit hole. That has never existed in media before. Right. So And you want to let'em go, but you need to make sure they're taking the stairs. Cause like if they just jump in, you're like, Oh God, no one has any context. They can't learn anything new because you're like you're not connecting it to something they understand. They just jumped into brain surgery. Yes. Let's just explain to us what's on here. Wha how are we gonna chop up this brain. Right. Like yeah.

50:26 Yeah, it's a it's a bit of an art, but you know, I I have to say, like it's it's been a different muscle for me to flex. And uh it's been great fun for me. The other thing, like I don't know if you think about it on this axes at all, but like I kind of think of there's I used to think it is very binary. Like there's two categories of podcasts. There's uh candy and there's vegetables. And like I listen to the audio version of Stratekeri and that's my vegetables, and it's not like deeply it's enjoyable intellectually, but it's not like fun and Um

50:55 I I can't I certainly can't be doing anything else with the language center in my brain while I'm listening to that. I have to be like on a run and like sometimes even at home so I can take some notes or look something up. I can be cleaning. Pause that I can't pass. Yeah, pause it sometimes. Sometimes you hit and rewind. Right. Let me make sure I get what he's saying here. Or I can listen to the talk show with John Gruber and it's just like

51:17 If I missed out on twenty minutes'cause I was like brushing my teeth and then I left the room and I came back and I'm like Oh, I didn't actually miss anything because this has just been it's comforting. Yeah. It's like I love all the stuff he's talking about, but like it's not must listen every time, every minute, every second concept, and I'm not using hard parts of my brain to understand. All in has become candied vegetables. It's both. It's both, yeah, for sure. Yeah, I thought I'd try to do with this week and startups and all in is try to have it be both.

51:44 A little bit of personality, a little bit of entertainment, some fun hot takes. Yeah, I mean Related but separate topic. Um Silicon Valley. Yeah. I feel like there especially there's a lot of Part of the even the origins of all then, there's a lot of like bashing on San Francisco politics and Calvin, like there's a lot of crap wrong here. Yeah.

52:04 But you guys are all still here. How are you guys feeling about that? Yeah. How how do you feel about that? Like what what do you think of the area? You know, I lived in New York. Brooklyn, then Manhattan, and then I lived in LA. And then I lived here and so

52:18 I think my Um moving to places I enjoy less and less each time. I I enjoyed Brooklyn and Manhattan much more than LA. I enjoyed LA much more than San Francisco. So I don't know where to go next, but I'm gonna go somewhere like it's a good thing. So why are you still here then? Uh I can't I'm gonna came up here because I had a lot of friends up here. And

52:39 I had done LA And I was like, I wonder how far, you know, I'd been a Sequoia scout. And then I was like, My friends are telling me I could start a venture fund. You kinda need to be up there. I wonder how I would do if I was up there in the industry. And I was kind of this if you wouldn't, you'd always wonder. Well Mare Michael Moretti used to call me the mouth from the south.

52:57 Uh because they had like two investments in LA. Oh the mouth from the south is here. Sir Michael saying that. Uh but I moved up here and I yes, I love it up here. It's quite bucolic, my kids are loving it. Um it's it's quite nice. I Would love to live in another city in my life, uh or two. Uh I could see myself in Austin or Miami. I like both of those cities. I think Austin's kinda the future. I think California's gonna be

53:23 uh damaged for a decade or two, so I think for the rest of our adult lives Because of the pandemic or I think the politics And not appreciating The politics of regulation and not appreciating

53:37 The tech industry is really the problem. Um, and then you look at this guy Dean Preston, like he is Dunking on Um the founder of Away and Stuart Butterfield from Sack. They're a couple. Yeah. 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

53:55 Tens of billions of dollars of wealth for San Francisco. You idiot. And like at the same time Francis Suarez in Miami is listing all of the venture capital and doing a tweet storm about all the companies that raise venture capital.

54:09 So you have one guy deimpressed and dunking on people saying, We have this one percent. So when they sold their thirty million dollar house. We were able to extract a million two, that's why tech doesn't like when I was like, hey dummy. Yeah, now the all the picture earnings are gone. I think it's a good thing. California marginal tax rate is thirteen point three percent. I mean, but just they have an exit tax now for homes in San Francisco. So if your home costs over ten million.

54:34 When you sell it. I mean I think it's just a sales tax. Thirteen percent of their future earnings stream. Literally the chef at Slack made a billion to paid a billion two in taxes. Yeah. from their RSUs. Like are you such a where do you think that would serve Probably. Like the bil the million two. Yeah. But that'll be magnitude. Probably paid in taxes on their RSUs at Slack. Yeah. You absolute moron. Like

55:03 You're literally so upset about their mansion. And dunking and and you're donky on An individual's name. Uh but anyway. The fact that we hate entrepreneurs who create

55:14 jobs and wealth or certain people do. It's just insane. It's just insane. Like what I mean, you could Go change the tax code. It's fine, like you know, raise the minimum wage. Uh like Bernie Sanders and Elizabeth Warren attacking Bezos endlessly and then Amazon starts paying twenty two an hour.

55:34 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 Inact.

55:44 And he enacted it inside of. Amazon. If it's not perfectly clear what just happened. Literally he's dunking on you. You wanted free college and couldn't get it done. He gave it to Amazon employees.

55:55 You wanted a fifteen dollar minimum wage, he made it twenty two. And you wanted everybody to have universal healthcare. And he gave universal health care. Like that is literally what Bezos did to them. How and maybe you could argue that like them pushing him pushes it, but No, no.

56:09 Yeah. Definitely i i it it is literally him showing like Uh it's the Amazon crew showing like Let the free markets work. Like

56:18 The door dash The Amazon, Starbucks. Absolute. Um

56:26 uh race en and battle to just hire entry level employees and make it delightful for them. Is what has driven And a lack of immigration has is what has driven these uh salaries up, right? And the benefits up. It's extraordinary what's happened with the free market. Minimum wage is still$7.

56:44 Federal minimum wage is seven and change still, right? Uh, and fifteen here in the city, uh in New York is fifteen, like Yeah. It's weird. All right listeners.

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58:42 We referenced this at the start of our conversation. You're working as harder harder than you ever have. You said you've got a smarter. A new well of energy. Yes. Tell us about it. Well, I find great purpose in what I do.

58:57 And uh when my friend Tony Shay died, I really thought deeply about like what I wanted to get out of the rest of my life and I realised like w these are the things I really love doing. And these are things maybe not so much. And I just realigned my life over the last two years. And So what are the two buckets? Yeah, exactly.

59:17 So I can tell you the things that just to me I'm just not gonna get any pleasure of out in life. Um Working like no offense to my incredible lawyers, but negotiating terms sheets and legal and HR issues and accounting and operations and tax and you know, that entire stack of things. Not fun to me. Not fun at all. And I'm sure you never viewed that as fun, but at least before you were like, I'm willing to put up with it'cause it may may maybe it's a thing that creates value enough for me to do it.

59:43 Um, doing my podcast every day. Absolute joy. Hm. Entertaining an audience. you know, thinking uh thinking about the world and having these conversations. I had Toby from Shopify on today. Like I leave the Toby interview. It's like his third or fourth time on the pod. That's awesome. And it's just like instead of us having dinner or lunch, we just record a pod.

1:00:02 The end. Um person or did he No, just you know talk on Zoom.'Cause he did that tweet about his compensation tool where you know, here's your total comps. Use a slide. I was like, That's brilliant. Come on the show. Yeah, of course. Um and so like those conversations, I just looked at them and I'm like, My energy Coming out of the show. is on eleven.

1:00:26 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 can be like those guys. Uh they

1:00:37 Every day get on there. And they seem to love it. And I do, and so I just committed to doing it every day. And I love it. Isn't it weird when there's something that takes a ton of work, but somehow it doesn't drain you. Not at all. To me it's like going to the gym. It's like working out or having dinner. It's just something I do every day. That gives me great joy. And then that's I recruited Molly. I was like I need somebody to do this with me every day. Oh yeah. Who I respect and who's awesome and bring something to the table that I don't have. And having so great. Having someone to play off of like I feel like that's the thing that's kept acquired going. Yeah. Is that like you and I can like I don't know how you did it alone for a decade.

1:01:13 Uh well, I you know, I'd have guests on. It was it was largely a guest driven show and then I would do the news round table once a week,'cause it was once a week, then twice a week, then three times a week, and then I was like, Well However many ages I'll out I'll do it. Five, six days a week, whatever. Um and um I enjoy meeting with founders uh uh when they fit a certain profile. Uh but

1:01:34 it's very hard to meet with a large number of founders given how many are coming in. And it's hard to work with them when they're just talkers. Yeah. To me that's a very hard part of the job because it becomes very repetitive. So how have you exercised that? Well, I created a platform. Founder University, where if you want to build something, I will talk myself to 200 people you can build.

1:01:56 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. Yeah. And so I'm like Bring me the people who have product velocity.

1:02:13 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 I kinda like it that way, but The Angel Syndicate is now the largest syndicate in the world. I've deployed like a hundred eighty five million dollars in my career as an angel investor doing fifty million a year. Now I'm raising the fourth fund in public. Like

1:02:34 Eleven thousand angels in the syndicate. Like this is going at a really significant velocity. If you were to look at the slope Uh it's not quite a hockey stick, but it's hockey stick. Ask in terms of The total capital I've deployed. And it's in really high quality companies I'm getting better at. There's eleven, I have twenty two people and ten on the media side and twelve on the investment side. And of the investment team, like people don't understand. They're like, Oh, you're a solo GP. I'm like, Yeah, with twelve people. Um

1:03:01 Those people are doing sixty introductory meetings per week. Six zero. And then we're doing maybe fifteen, twenty second meetings. So there's It'll be a hundred meetings a week shortly, probably across ten people. Or twelve. But you're not doing the I'm not doing them. Yeah. Uh and what happens is You had this line, was it on Twisted. People say that's a lot of work, but you're like, you have enough for me. That is the new philosophy. This is why my energy is really high. This is your I have told everybody who comes to work for me. I work Sixty, seventy hours a week.

1:03:30 Keep up. If you can't keep up, don't be here. Uh, I'm looking for a f you know, a fixed fifty, a solid sixty hours a week. If you want you don't have to match me sixty seven, but sixty or seventy hours a week, but keep up. And are you looking in that team, are you looking for like the next Jason Calicanus to be a part of that team? Or is it like someone who Likes doing

1:03:50 That part like that's Well but let me ask it more directly, is it someone who's content with doing this, or are you looking for people that are like hungry enough to be the next Jason? I I'm open to all of it. You know, I'm open to all of it. I don't they don't need to want to have my You know Absurd.

1:04:06 um unhealthy desire in my youth to be successful. Um and if they did, they probably wouldn't come work for me, but maybe they would. Actually I would. Uh so yeah, they probably would. Uh not for very long. Yeah, you come, you'd extract. People come and they work for two, three, four years and they go s start their own venture fund or whatever. Muscle towel that's great. Um Por I Told them was, you know, let's just find the great companies and I looked at investment team meetings, usually they're Monday.

1:04:33 People do it for an hour or two and then they go to lunch. Uh, I said I want to do it twice a week, Tuesday and Thursdays, two to four PM. Uh Hit me with companies. So that was another innovation I did. And I also brought Mike Savino, who was my first boss

1:04:46 when I was in my twenties 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 finders. do the LP fundraising. That's it.

1:05:00 Hm uh teach the course. Are you enjoying the L P fundraising? I am now, yeah. I am I'm kind of like Uh remember in X I don't know if you watch Billions every episode. Great. So you know, like at some point, um Uh He was like

1:05:16 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 uh I got my Wags who just fixes everything. And I'm like, I'm gonna go raise money. And so it literally was like we're doing five oh six C and they're like, And so you've talked about this now. You're you're 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.

1:05:40 And you want the big institutions, right? We'll see. Um I've had select institutions make small bets. The first one was ten, the next one was eleven. And then the last fund was forty four million. The first fund I deployed in five years, the second fund two years, the third fund two and a half. 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, Chamoth. Just a bunch of my friends put money in and

1:06:07 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 I raised eleven. Took me six months to a year to raise the first. It took me the second one took three to six months. The

1:06:23 No, it took six months. The third one took me three months to six months. And in this one I I think I'll wind up raising in the first Ten days what I raised in the

1:06:34 First. Yeah, a couple of funds. I literally did two webinars, a couple of hundred people came to each so for people who are listening, five oh six C is you can raise in public. Which means you just can tell people I'm raising a fund. And I was like, Well I'm doing all in, it doesn't make any money.

1:06:49 Have this week in Startups and I watched A bunch of these young um Inspiring VCs raise our Publicly. Right. Yeah. You didn't raise publicly.

1:06:58 No. Well it's kinda scary because people don't do it, but if you Have no track record. And you wanna raise so like this guy Mac the V C Yeah, you you did a great episode with it. Yeah, it was great. I had him on. Uh I had like, you know, first time founders for a season of Angel, um which is like a subsection of the This Week in Star Wars 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 raised my whatever ten million dollars and

1:07:29 Uh, he's African American and he's like It's just a matter of how hard do you want to work. And I'm like Well be careful saying that publicly because there's a group of people who do not want you saying that He's like, No, it's just all you have to do is like you go to Angelus, you set it up, and then you just start talking to other VCs, you talk to them and you just you just have to be willing to take fifty meetings a week. I'm like dude do not say that it's easy to raise a Venturephon as a black man in Silicon Valley. But that's the It's not that it's easy, but on the internet too, you find your people who believe that you and then they believe in you and then they back you and that's the line. Correct, correct. And so the whole thing but what I noted when I was taking my notes watching him was so many times people like, Oh you're ca when's your next fund? I'm like, three years. They're like, Oh, let me know and I'm like

1:08:11 Okay. Right. I'll I'll put that right there in the place where I keep everyone who tells me three years what you do, yeah. And so, you know, um I mentioned it on all in. I'm Tweeted it and all of a sudden, you know, I had a thousand people sign up. Is there a limit to the number of LPs you can have core five by six? Two and fifty accredited, up to ten million, and then two thousand QPs. And so it's it's a it's a lot more work. And and and QP not for me. Not for you. But not for me.

1:08:38 purchasers. Look at you playing Jason. I know you know what it gives you. I just want to dish the ball. I think it's five million in uh investable assets. Like uh and then uh accredited now is two hundred if you're an individual for the last two years each of the last two years and three hundred if you're a couple, each of the last two years in income. Or a million dollars in net worth. In net worth outside of your primary residents. So there's a whole and these things are gonna change over time, but I believe That we're gonna have a test. for accreditation.

1:09:04 and you'll be able to be sophisticated if you take a course. So I think that's coming in the coming year. So Just like I democratized Angel Investing, wrote the book Angel, was the first syndicate on Angel List, the most successful syndicate on Angel List, created my own, got the domain name the syndicate, created the largest one, have done two hundred sixty five syndicate deals, by far like the largest amount of anybody, I think. I don't know. Oh, with the Fund Angel list. Like I did these are like all those are big numbers. Like Four SPVs on Angel List and we we have the fun too, but like you know. You're herding cats, you need to have a lot of people. Um

1:09:40 But anyway, putting all that together, I think now's the time to democratise venture capital. So that's what I'm attempting to do here is I want uh more people who are accredited in qualified purchases who've never been in a venture fund. to look at the asset class and just consider it. Um it's high risk, it's high reward. I'm in twenty venture funds myself, including yours. Thank you. Um and I'm sure but don't pitch Jason. I'm sure do yours. No, I mean I I'm just gonna pick them based on people I know or people I know online or people in pod and Yeah, I'll probably do one or two new ones a year and um But this is kinda to the conversation earlier. Like on the internet, this is the democratizing thing. Nobody's gonna just give you

1:10:18 If you just r you know, nobody's gonna just invest in your fund, but if you go do stuff and then people like, Oh Jason does stuff. Great, I'm a back taste. Ben does stuff. Like be of action. Yeah. And it doesn't mean you have to start a podcast. You could be a blog, you could do events, you could create founder university, whatever it is. You can do any of those things. Um you can have a track where you can be an advisor to startups, whatever it is. Do you like the idea? I'm I'm curious, as someone that's always raised uh uh from sort of individuals, Do you

1:10:44 Do you like the idea of having some institution be like, ha can we invest fifteen million dollars? Oh yeah, of course. I mean I I've had five, you know, million dollar checks, ten million dollar checks in the fund from institu from you know, fund to funds and and institutions you know, but I would very much at some point I don't need it. But it would be meaningful for me, uh, both my parents are cancer survivors, to have Memorial Sloan Cattering's endowment or an endowment or something like that. Yeah, somebody like that, you know, if they wanted I would work you know, really hard to try to get them a great return. I would find more I would find even more meaning in what I do. Yep. Uh and I you know I got that from Sequoia. Like, you know, you they would have this Sequoia dinner every year for the founders and they would say

1:11:25 Here are what The foundations who are LPs are doing with the money. you made for them with your company. Click, click, here's what Four Foundations doing, here's what this foundation's and you're just conference rooms are named after their conferences are famous and named And and this is real. Like I I find we have like state pension funds and stuff like that. In PSL ventures. And like

1:11:47 You take it much more seriously. You're like I am it's'cause it's not just about the reward. It's not like oh I I'm so excited about It's like This is really important to preserve and not to grow, but like preserve this capital. Yeah, yeah. Which w the the psychology of

1:12:06 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 uh billions was he's like, I'm gonna be a family office. No, I'm gonna raise my own fund. And so there's this natural tension for um Acts like Which should it be? And he decided Yeah, I like when I have other people's money because I he I he seem to perceive like

1:12:31 I think he felt that he wasn't a somebody in his ecosystem, in his community without Managing outside cap. You know, in the bubble with nobody in the stands versus getting on the court at Madison Square. It's like and there's people in the stands. Your returns your numbers don't mean anything unless you're putting'em up for Dude, I'm doing this public where I should say quasi public people that still have to sign up. to you know come to a webinar um

1:12:56 But I'm sharing with them like here's my the totality of my investments and here's what I've done and here's what I plan on doing with my team. Um so you know, it I'm kind of enjoying it. Um and If You know, I've met with all the top endowments in the world over the years and they're very kind to me, but it's always been like solo GP is a blocker, no track record. Your funds is so small. Small f yeah. Small funds. We're a fifty billion dollar endowment. Yeah, and you know, like you know

1:13:22 Um at some point, like one of the ones who's the most rigorous, I wouldn't say exactly which one was like We have a lot of respect for you. We know who you are. People would like you to sign a book and take a selfie with you when you're here. But I just wanna be straight with you. We don't add many funds. And if you go through our process.

1:13:41 It's going to take a lot of your time. Mm. And it's gonna result in you. Not getting our money this time. I don't want to put you through that, but I respect you.

1:13:51 And if you want to do it. We'll do it. But maybe just put one more fund on the board and let's talk on the next one. And I was like Let's do that. Hm. I don't need the money.

1:14:02 Let's wait. And I think what a lot of these funds are doing is Was that in the last fun cycle? That was in the third fun cycle. Yeah. So now So I will contact them. What I decided to do was Let's see what. my syndicate members and the public wanna do. Let's see which QPs come out of the woodwork. Yep. And uh 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.

1:14:24 Uh, I added two more, so I'm gonna do five webinars this fall and then I'm gonna go on the road and start meeting with folks. Are there any downsides to doing the the raising in public thing other than 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.

1:14:41 No. I could also you know the the the freeing thing, you know Is I looked at the model and I said You know what I could do?

1:14:51 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.

1:15:02 Yeah, and I'm getting deal by deal carry. And I have a hundred percent of my investment, not twenty-five percent carry on it. And I don't ever have to talk to anybody. I could just say, I'm placing this bet.

1:15:14 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. Wait, this is so literally this you know, we're so funny hearing you say this. Myself.

1:15:25 lots of our other friends in the ecosystem that are in similar positions, they're having this same question like on the one hand I could do what you just said. And do very little work but but have it all be pure. On the other Yeah. I could go do what you were actually doing and like raise have LPs be account of it. Yeah, how did you weigh these two?

1:15:44 Um I I'm going into my second era my second decade of uh investing. And I

1:15:52 Again, last two years a lot of like sort of Post pandemic and Tony's death thinking, huh. Like What's possible here? Because

1:16:03 I've won so much in my life, I don't mean to be obnoxious about this. I know it probably sounds that way, but For a kid who's, you know, gonna be a cop. To be where I am. Uh And this is why like when the guys break my chops on the pot, I'm like guys

1:16:17 I don't aspire. To be a billionaire. I 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 forty days of skiing, hang out with my kids, take them on the mountain, and then meet with like

1:16:34 you know, early founders and be able to say, I helped that company. At the early stages, that to me is the rush. I found him first. I backed him first. I sat there with them and figured it out with them. We were talking about the legendary twist episode one eighty with you and and Travis. Yes. Like

1:16:54 I mean that's the secret before the show stuff, David. Yeah, that is the secret stuff. Yeah, but that was like you know, you know, Urbu was such a baby company back then and like crazy one city. And I invest it and I had an open angel for him where Cyan Banisher and Chris Fralak from First Run, you know, invested in the company. I think they both met them there. Saka was there too, but he already he had a relationship with Travis, so I can't take any credit for that. And Kevin Sistram was watching and I was gonna kick him out.

1:17:24 Because he was at this co working space called Dog Pass. I worked there too. Yeah, Co Tweet. Yeah, so he was Oh coatweed, I know that. Yeah. So he's sitting over there building bourbon. Yep. And Saka's like, Can Bourbon come in? I'm like, Fuck no, this is like private shit. And he's like but and I'm like, just tell him to sit at his desk and I won't get it. No, then they shut down because it was gonna call. Naval also did a bunch of like events there for Angel Power. I at the time, Naval and I were very friendly. Um Not Not friendly now, but

1:18:01 Not We don't hang out or we but we used to hang. Um kinda bummed about that if I'm being honest. Um, I really respect him and uh he was doing something called venture hacks at the time. So he would just send an email with here are the five companies and I was doing it in person.

1:18:16 He's like, I'm gonna do this thing Angel list. I'm like, Well I'm just in person thing and he's like, Great, let's just, you know trade notes or whatever and he then he sent me the syndicate thing. He's like, Do you know about SPVs? I was like, I don't explain it to me. And he taught me what SPVs were. He introduced me to a short fund management, which I wound up investing in. Um did you buy that? I didn't buy it, I I mean I bought five percent of the company, I invested in it, but they back everybody and uh they've done more S P V is like L like I don't know if they're up to ten thousand, five thousand, I mean they've done a ton of it.

1:18:45 Seriously great group over there. Um, and so he taught me how to do Syndicates and the first one I did was calm. I had four or five. It's funny, I was I was looking for it. 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 uh because like obviously Uber is some ridiculous multiple on a return. Um, but then there's these other ones that are like promising but early, and then there's other ones where it's been a less than Uber multiple, but still a good Uber multiple. But you look at Calm. You just sh I t I looked David and I was like he sharpshootered that one. That one I could be even more proud of because I'd tell you why it was like ridiculously early and like a super low basis. They had

1:19:24 It was four million dollars, we put three hundred eighty K in on six percent, and uh they didn't raise any money until it was a two hundred fifty million dollar donation, so no dilution. Um and uh sharpshooter. Sharpshooter. It's like the same story. I could even cry like Telling the story, but um Alex too and I became very good friends. And Michael Acton, you know, afterwards, um,'cause he wasn't actively running Calm while Alex was. Um Alex at some conference I was interviewing him and doing a little victory lap for him and um giving him his flowers and he said, Yeah, I just want to stop and tell ya

1:19:57 uh you don't actually know this story about we were gonna shut the company down. And we have Mike and I had a conversation. What do we take your money? But we're not sure about this. But you believed in us so much. And you insisted on us taking the money

1:20:12 But we had just pitched forty 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 when it's a product market fit while burning through your money. I think so. I think so because you're like take more of my money. No. But I mean if you think about that as like a

1:20:33 That is not the case with Uber or Robin Hood. I was along for the ride, let's be honest. Uh the I did not change the trajectory of the but for Jason Calicanus calling is not It well he said it's they were gonna 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 venture rounds. And like Yeah. No offense.

1:20:58 Oh any offense. So like call that angel investing, but like coming in when the company could die. needs a hundred K, two hundred K, three hundred K to get it to the stage where they're revenue to date, I think, when I invest. Yeah, uh because they were selling the app for ten dollars. Because remember, at the early stages there was no subscription model. Right in the app store. You just sold an app for ten dollars and had it for life. So the business model of apps was Make a lighter for a dollar, then make lighter two and charge three dollars and then lighter four would come out.

1:21:30 And you're like Well, this doesn't make any sense, but it's like making Microsoft Word one point oh, you buy it, you throw it away. It's like but we could just update it. And it's like yeah, but we need to make more money, so shut the old one down. So you'd buy Angry Birds and you buy Angry Birds two, Angry Birds three, and Yeah.

1:21:45 time and then they're like, Yeah, we're doing so they they told me like, you know, um 'Cause you know, I was under NDA as well, and you know, hey subscriptions are coming. That's gonna change everything. And then we're gonna do ten dollars 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 like ten places you can go. I'm like, well what if what's a suggested donation? It's like twenty dollars, you know.

1:22:07 I said you wanna charge ten dollars a year, it's twenty dollars a month. How often do you have to do this to visit? Yeah, I yeah, twenty hours a visit, I said, How how often do you have to do this if to get value? Which should be a daily practice. I said, if you go weekly that's good, Isaac, so it's eighty dollars a month. to go and we're charging ten dollars a year. So that's like a thousand dollars a year versus ten dollars. What if it was ten dollars a month? Like we've been thinking about that. I was like

1:22:33 Okay. And they're like, Okay, yeah, I think we're gonna do that and it was a then they went to ten dollars a month or whatever. And then I wound up at sixty dollars a year or whatever it was. But it became a money printing machine pretty quickly. So I've never made an investment at like Pre-product market fit that's like now worth over you know a billion dollars. Like that's a that's a that's a very early to very successful. And I'm curious. Like, did it feel any different when you were making that investment? Were you like, there's something ac more special here than quite my normal investment. Absolutely. Really. Absolutely. And that that's what I've basically turned into a playbook at launch and that I'm teaching these twelve people how to do is how to do that. What do you think it was? Like what what was when you look back and you're like factors. Nine factors. Okay. All right.

1:23:17 Yeah. Well Angel.univers. Angel Dot University. No, I teach an Angel.university, but um I I'm training my team when they're meeting with those sixty companies. And every time they pitch me one, they say this has three of the nine. This has four of the nine. And then I'm creating the anti-list. These are the things that kill companies. So how many of the fifteen things we have a long list of things that kill companies. How many of the red flags does it have? Reasons to not invest. How many reasons to invest does it have? And you know, like one of them for me, and everybody's got their different flaws, so I won't give all of them, but one of them is world class design. And so I'm trying to teach people what world class design is.

1:23:48 And work class design to me is if you were to look at all the companies in the space, this one would have the best design. Where this would be one of the top ten percent. So if you were to look at Something like Calm or Robin Hood. Okay. They're the best looking app with the best UX of all of of anybody in the category. Right. So Calm was better than Headspace, Robin Who was better than E Trade. I mean it's just doesn't take a rocket science to look at them. But when I first explained this to my team, they would bring me Companies

1:24:14 And they'd say Work West Design. And I was like I'm like I really like the design. I'm like Pull it up. They pull up and I'm like That's a template from Yeah. You know, like a website builder and it's a stock photo, but where's the actual design of the product? And they're like, Oh, that's on this product page product page. I was like

1:24:33 Okay, th yeah, again, that's just like the I mean if This was a bank's website, maybe, but That's not world class. That's serviceable design, that's utilitarian design, that's okay design, that's good design, it's not world class. So let's if we're gonna say world class.

1:24:49 Like a world class performance is different than a serviceable performance, world class cinematography, world class script. World class dialogue. That's different. That's and then product velocity is the other one I like. So Okay, we met with this company in June. It's now July. What's changed about the product? And they're like, We don't know. I'm like

1:25:06 Okay, well let's find out. Where's their change log? Where's their roadmap? So in the earliest stages you might have revenue traction or user traction, but you might be able to ask them for their product roadmap and Somebody like Travis would be like Yeah, here I'm get on the phone with this guy and we'll walk you through it. Here's what we're debating about on Sunday. We're reprioritizing. And then that's check check. And then you go like if we're with Raul with superhuman and I was an investor in his company before that report of Ro like the change log at superhuman. Superhuman that people realize like

1:25:35 They're like bink, bink, new feature, bink, new feature. Oh boom, we fix grammarly. Oh bink, we have calendar, boop, oh we got a new calendar feature, boop, we got this feature, and you're like Hm. So here's an interesting question. We should ask Ruffle this,'cause we've had him on the show three times now. Product genius. Like The the parallels between superhuman and Figma are uncanny. Like design led founder, uh like revolutionary design in the software, rewriting the entire browser stack in order to get to performance. And I remember it being Breakthrough when it came out.

1:26:05 And then the only thing that I can recall being different between then and now is Adding a calendar thing that I don't use and a mobile app. And iPad support. And it And why?

1:26:15 Outlook support. You just don't you know, when you hit Command K, you probably know fifty percent of the features right. Like do you use remind me of this? I do. Okay, great. Do you use labels? Do you do bits? I do. Okay. Yeah. Which it was all there when I started using it. Four 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. Um I really like want them to make snippets multiplayer.

1:26:43 I wanna share my snippets with your team. Yeah. I love I want to go off David's pass emails. They're so nice. I don't think I'm not going to be able to do it. Like I'm not going to do it. You do it on the phone. No, I just don't do email. I just doesn't email. I've been I've been literally creating a collection of how to pass with my team and I'm standardizing that. I'm trying to update the founders. I don't know that I'll be successful or this may be a mistake, but I'm trying to

1:27:10 Just not head. 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 Oh no, I I I don't I don't I don't know.

1:27:23 You basically don't take a picture. Unless you're gonna invest. It's the weirdest thing. Oh that's very weird. So you do all your work up front? You front load it, the deck, everything. We're in this unique 'Cause I you are too, but um With acquired where like

1:27:38 You know, we have every six months we have six companies that we work with on the show. as our sponsors and our partners. And we get to know them really well. And I'm now an investor in just about all of those companies. So it's not like a pitching me. It's growth stage investing. Yes, it's growing investment. Yeah. They're not priced as if they're the winner. Most of the time. Yeah, exactly. They're gonna just keep compounding. Yeah, good luck. Yeah. Pricing's gonna be hard. Uh depending on entry price. We'll see. Yeah, I don't know what's gonna happen to these companies after You know, like flat is the new up, but I think

1:28:12 You know, fifty percent haircut is the new flat. So Yeah. Fifty plus percent. Yeah, they got hit harder again. Yeah, I mean I I'm buying equities right now. I've been doing it at Jtrading dot com and um I am gonna buy more sorry about all the fixed a couple weeks ago. Which one? Uh whatever I told you. No, I I actually love Taiwan semiconductor. Uh Ditchfix was the other one.

1:28:37 Twili always yours, and I love that one too. And I I I like Shopify as a pick. Um I'm actually really enjoying it. It's really not investment out not investments, but I'm it's balancing out my Um understanding of what public success is compared to private. And so for me it's just a way

1:28:55 Like am I going to fight with a blast or no I'm a Jedi I use a lightsaber. But But if you learn the very best, it's helpful. It's really helpful. If you look at the very best people, the best GPs in venture over the past Two decades. True. They all trade public stocks. Yes. And they do it for the same reason. They're gonna fight with the saber, but like they wanna know. Yeah, or how to Fighting an X-Wing or something. Like it's not what a Jedi does, but Jedi will do it. It also keeps you really sensitive to the public cycles.

1:29:30 So that like y it's not that you have to think about the public comps when you're investing, but you have to be aware of how much those will change. Yeah. And early stage investing, it's almost silly to compare to like my opinion is it's very silly to compare to public comps, because the only thing you know for sure is we're gonna be in a different place in the cycle by the time this company gets liquid. So Just it's ridiculous, but it's helpful to gr drive into you like how much variability there is, when was the last time it was this different, that sort of thing. Yeah, I'm really enjoying understanding what the founders of those companies go through versus the founders of the private companies that go through, what the board's d decisions the board has to make of a public company versus the board of a private company. Yeah. So it

1:30:11 Yeah, I'd like to join a public board at some point. It's probably not a good idea for me to have said that because I might get an influence for one and that might be too much work, but Um Yeah. Uh especially given the market right now. But you can you could also invite me to do that. But it's just it's been especially through the show now. You you have relationships with public company founders. Sure, of course. Oh, I'm just going to be able to do it. You don't have to be on the board, though. You can have a great relationship. Doing the analysis and I'm doing it anyway with Molly every day. Okay, you know, Twilios or Adobe's coming out. I just bought Adobe this week when they bought Figma. So funny, so did I. Not investment advice. Not investment advice, but I was like, They bought Figma pink.

1:30:49 Okay, so here's my theory on this. They bought Figma untanked and I was like, Why did why do people hate this? And they're like, Oh no, Adobe's admitting defeat and that like they can't innovate in house or And To me. I I look at it like Adobe

1:31:03 has customer channel And It was foretold five plus years ago that they were not going to build the next Figma. Like that would be a full rewrite of their entire software stack. So buying the thing, even though they paid a tremendous premium because fifty X revenue multiple because of the network effects that Figma has. Um and obviously all the product stuff, but if they can get that through Adobe's channel

1:31:27 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 twenty billion dollars for it and have a gigantic bonus for Dylan to stay on board. Yes. They're taking a YouTube approach. I think everybody in MA now knows now. Yeah like Or WhatsApp. WhatsApp just leave it alone. Don't screw it up. Um and then so I I like your analysis. I

1:31:54 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

1:32:04 They've just removed the downside of Figma creating Photoshop. I'd be concerned for Adobe if Fig they didn't buy Figma. Correct. So The fact that you're giving us a discount on the shares for them doing the right thing. is like Christmas, like thank you. Yeah. Yep. You just discounted the right move. Fantastic. It would be like

1:32:25 People are like, oh, you know, the Warriors signed Kevin Durant. And you know what? But they paid a lot to get him on the team, so Yeah, and oh you know what? We're gonna lower the cost of the tickets. So I'll bite. courtside seats or yeah, or they're lowering the odds in Vegas. It's like

1:32:43 Wait, you're why are you lowering the odds? The odds increased. I I'll place that bet. So it's just an obvious bet, and then there's all that's left is Canva. And Metlane is awesome. Totally different thing. But yeah, and they have a free Canva. Already And you know, what if There's a

1:32:59 The internal people who are penciling out that spreadsheet. Yep. There's a group of MBAs Who penciled out that spreadsheet with Figma. No offense to MBAs who are listening. And they said hey boss. If

1:33:11 X Y if XYZ And they said, you know, here's like five potential paths. If we make Figma free. Or if we You know,

1:33:23 Take Whatever Figma costs, and then we blend it. Yep. with the Adobe Suite. Okay. we would get this many more Figma users. But we know when we get Figma users

1:33:34 Then we get non designers to pay for it. So right now Adobe has a bunch of designers paying. Right, right. But they may not have all the non designers in there. Only designers pay Adobe. Right. Well no they've they have marketing cloud, but that's a totally creative. Yeah, yeah, only But when you look at Figma, like I got a Figma account. Like people who are Doing Giving feedback on designs

1:33:57 The business side, the sales side can get into Figma. So I Plus they got the whole creator class. Exactly. So I think The you're opening up the aperture of who designed software is for with Figma. It's for B D. It's for the CEO. Sure, the CFO can come in and take a look at the product. Oh, legal should come in and take a look at the product. Yeah, buy them a seat. So it's like Slack is for the dev team and it's like

1:34:16 Yeah, and the sales team. And ops. And anybody else might as well be on there'cause that's where everybody is. So that's where they can have a Figma. It's like everybody's gonna have a Figma account in the future. Just watch. the product team build the product and put a comment in and who cares if it's a hundred bucks a year, it's costing doing business. Any any company that

1:34:33 Has un like that kind of strong network effects inside an organization. deserves a meaningful revenue multiple because they just Their differentiator is literally a the company's moat. So like I I tweeted this, but like if I have a castle

1:34:48 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 because it's more defendable? Hundred percent. Like the virality of it. I think Sachs made this point on All N two weeks ago, which was like If they're paying fifty X now and the company's growing

1:35:04 Okay, they're paying twenty X next, twenty five X, who cares? Right. If seeing such a high growth company. And then I was just thinking Well, somebody's got a theory there and When I sold weblogs to AOL, people were like, Oh my God, these people are idiots. They gave thirty million dollars to you know for weblogs inc. They've only got two hundred K in revenue. What they didn't realize was AOL autos, AOL tech. AOL lifestyle, those were sold out at like a$90 RPM revenue per thousand pages. They adds different CPMs.

1:35:32 So then they would put an ingadget or an autoblock story. Or blogging baby or whatever other blog we had on the homepage of AOL. And a half million people would flow through. And then they would put those ads on our sites.

1:35:46 And then they would blow out fifty or a hundred thousand dollars in ads a day on a blog. And those people were like, Great. Um because it was costing AOL to make content. Like five hundred dollars per piece of content.

1:35:57 Three thousand dollars per piece of content. on AOL dot com slash auto's whatever. And we were doing it for At the time, five blocks of bog

1:36:06 Five dollars a blog post. 'Cause we said, Well, people can write four an hour, so it's twenty bucks an hour and it's six dollar minimum wage. It makes sense. You guys were doing two hundred K Annual revenue. We had done two hundred K to date. Holy crazy. Over the eighteen months. What is it?

1:36:27 Jake Howd has robbed. Yeah. And I was like Okay, thirty million dollars. I look like an idiot. I look like an idiot five years later, and that's the best The best MA is when You look like you robbed the bank.

1:36:43 Yeah. And then five years later, it looks like you robbed the founder. YouTube, Instagram, Figma will be in this category. Like Yeah, when they bought Instagram, they're like thirty people work at this company and they gave them a billion dollars. You guys are morons. And now it's a hundred. Here's a thought exercise question. Obviously irrelevant because you don't monetize it. Yeah. What do you think the enterprise value of all in is? Well, it would do ten million dollars in I I I when I was at the code conference, you know, a lot of people have been trying to buy it or

1:37:10 Yeah, put it as part of their network, obviously. Uh which would kill it. Yeah. My partner's alright, 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 huge economic value out of it. Shmuck pulled me aside at some point and was like, Hey Shmuck like Just we're friends, like you're all your next friend will be bigger than I was like yeah, when you have a friend who can be like hey dumbass, yeah like that's a good friend. So I appreciate that. And he's right. And it's playing out. Um and we had a rule no

1:37:41 Um no talking our books on the pod. But we kinda talked about it and we're like The pot is great when we talk about our bets. So explaining our bets. Not Talking our book is the new philosophy. So like Friedberg doing it's talked about his spaces.

1:37:55 You know, um I did, he just uh found a target for it. Yeah. The healthcare company. Which is a I mean, we wanted to talk about that because Chemoth and I both agree like maybe we're But I mean maybe. Like we're definitely over prescribing.

1:38:13 these drugs to kids like for ADHD and attention drugs and adults are taking too many. I I think that that's not disputable. Uh I think all the science is showing that. Um, so you know, to make software that could help kids with ADHD is like noble. Um but I think people want to hear us explain our bets. So, you know, explaining our bets I think is kind of a cool aspect of the show. Talking your buck is lame, but explaining your bets is cool. So anyway, um in the event, did a couple million dollars, had a small profit. Um, but it was the number one tech event of the year by far. Right. So you know, I'm kinda bummed that

1:38:48 You know, Freeberg's a little bit of a blocker for it, but I might turn him around and we'll have a vote maybe in the doing another one. Oh well, I'm going to do another one. The question is, am I doing it under the all in brand or do I have to create a new brand for it? And so I told the guys, Listen, I'm gonna do it again. Well code conference is done. So like there's a bad thing. Yeah. They need a new host. Um That's crazy that that can be done. Like it's such a value. No, he's I talked to Bancoff about it, uh and he's been very public. Kara Swisher, I think, is gonna do the pivot stuff and wants to do other stuff. And you know, she's I I really respect what Kara has done, you know, um, 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

1:39:28 Bob Dylan, you know, said like don't look back kind of thing and he always tried to make the next album and forget about the past one and Much to the chagrin of people who loved him as a folk artist and didn't like, you know Like a rolling stone and when he went electric, they booed him. You know, I was like, Really? You're booing Bob Dylan because he's using an electric guitar? Are you guys dumb? Like did you hear all along the watchtower? Like this this is incredible. Um and so I think, you know, Carol 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. Yeah.

1:39:57 Which you're definitely. I am. You think? How could you not be there work? I mean I'm not I'm not even saying that to like make you feel like a little bit of physician. Okay, okay. You're you're joking about being humble. But if it's if it had that kind of prestige, it seems like Friedberg would want to do it. It seemed more like the thing he was averse to is the like Yeah, I I mean whatever, the issue is like we've had our issues. Um we will have issues. Um but Um, I think the there's basically two possibilities for all and summit. Um, I'm going to present it to the boys uh and say like here's the plan. Yes or no?

1:40:33 And we agree we'll put it to a vote. Will we put it to a vote? If three of us want to do it, we'll do it. And if two of us wanna do it. Then we can't.

1:40:42 Uh and if I already Freeberg already said, if you do it on your own with a different name, I'll come and support you and I'll show up to do a talk. Or do an interview or whatever. And I was like, Great. So I'll do it with a different name. If they don't wanna do it, um and the fans can decide if they wanna come or not and partially in. Exactly. So you know, it's up to the boys um if they want to do it, but it was like a pretty great success. Yeah Well yeah, and I I I I started doing um I started doing a call in show called After All In for the last two episodes where I took

1:41:13 calls about the last episode of all just to support David because I don't think people remember how great that app is. I want to be supportive of him and I have a small investment in it. Do you um very meaningful, but On the one hand this is ridiculous, on the other hand it might be ridiculously low. It's worth fifty million, yeah to to answer your question. Fifty to a hundred million. I mean that's a top as a top forty podcast.

1:41:35 It's worth at least fifty million. On its own though, but I mean like economic value that the four of you Oh who knows over the life Like if Chemoff or Sachs or I or Friedberg were to get but one more deal out of it and it's an Uber. Right. The economic value is nine figures. Right. Possibly ten. You know, like so you have to do it. But that's the thing like I think like man, weblogs like you were doing two hundred K of revenue. You sold it for thirty million. Pretty great. Takeaway, yeah. And now look at this. Like, you know. Yeah, I mean, listen, I hope it keeps going. I I hope we can keep it on track and um you know, I I love doing pods this week in startups is a juggernaut as well, you know. It's that was that for ten years and all in is What is that, like to quarter million listeners or something? Yeah, something in that range, yeah. I mean it's hundreds of thousands per episode and Yeah. It's it's very niche podcast, you know, it's not I'm not trying to make it all in.

1:42:24 Um I'm trying to make it for founders. And so you know if in order to make it bigger, it have to be worse for founders. Right. And I want with our show. I want the artist and capital allocators to listen to it. And I'm not trying to move up the rankings. I don't mind. you know, hanging with you know all in being number one in tech and then hanging out with you guys that

1:42:46 You know, slumming it at six to fifteen with you guys in the rankings. It's like that is where we belong. Whatever. It's not supposed to appeal to everybody and you try if you want to appeal to everybody, like read the Bible. Like that's If you go to the this is the beauty of it, who reads Bible passages and he and huge. It's like if you you can literally True crime religion read the Bible. Or Ben Shapiro dunking on libs. The end. That's like it's a Rogan. Or 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 twenty minutes. Like, but I that's not what I want to do. I wanna talk for an hour or three

1:43:32 About deep topics in founders and counters. I feel like it's underappreciated how much Howard Stern. That should be the next Taylor Swift type episode that we do. Yeah, no for sure. He wrote the playbook. I literally took notes. Right. King of all media. Do Nom?

1:43:51 I have never met him, would love to at some point. I have a lot of respect for him. I mean obviously he did crazy stuff when he was young and that shock jock stuff, but he in his later years became a great interviewer. Great interviewer. Great interviewer. He really refined his technique. I really appreciate that about him and he created characters. Sound familiar? Yep.

1:44:07 Uh he branded them. Yep. He showcased them, the whack pack, you know, all this stuff. Did he ever do a event? He used to do live events. He did the US open source where and then he would do Howard Stern's like New Year's Eve celebration. So yes, he did the equivalent of those in New York. But it was a very New York thing. So he like He played tennis against Baba Bui and but I mean he got ten thousand 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 from my childhood.

1:44:37 And then he did his books. Uh, which were phenomenal. And he did a movie. He did a movie, he did TV shows, so he's done a lot of stuff. And uh I I'm just starting uh the process of doing a reality show right now. So Literally gonna do it. No, just me. Um Besties don't want to do it. They don't have time for it. I mean I there was there was talk of like maybe all in you know, kinda going on to one of those services like people had reached out, like, Hey, would this work?

1:45:04 You know, and a lot more work though. Well, you know, we would have to show up in a location. We'd have to do it weekly. you know, there'd be some formats, some shiny floor or whatever. It's it's a it's a different beast. I don't think they have the time for it if I'm being honest. Uh but for me, I would like to do a reality show in the Gordon Ramsey kind of vein. Um, you know, where I'm helping founders. I think it'd be great for reach. Uh so I'm I had done a reality TV show with NBC. Uh and the Wine Stein Corporation. Um yeah, and it didn't make it on air, but I have the

1:45:37 You should be a sharp tape judge. I had been they had reached out before, Mark Bernard had reached out early on when it was Dragon's Den. Um before when they were gonna bring it here. So when it was Dragon's Den they they had reached out early, but I wasn't very successful back then. Um I wish but you know, I think now I think I would have the credibility and the advice to give that I could do a Gordon Ramsey style show. that would be very entertaining and educational and be completely different than

1:46:02 you know, the fundraising aspect and the pitch aspect of Shark tank, so I'm not gonna do that. But I I'm You know, I've got You know, the I won't say which one, but a very major

1:46:14 the major, you know, uh reality TV folks reached out, I think in part that was doing so well. Founders and companies feel comfortable. Like I feel like a A really amazing window in insight would be the type of conversations that you have with a founder as they're building the company. Yeah, so they would founders and companies be open to that. Yeah, so the NBA C show I had done the pilot for, uh which never made it on air. Um Um

1:46:37 What was really good was really about You know, me incubating companies. And uh they spent like four or five hundred thousand dollars doing the pilot. It was really good and it would have been a big hit. Did did it get canceled because of the hardware stuff? Wow. So they were just like anything that was in his company. Because he's uh Monster. And so anything associated with it. But you gotta remember he did Project Runway. So he had done some of these giant shows. People don't know that about that. Yeah, that had the T W C at the beginning. Exactly. So you know, I just and you know, I'm I NBC bought the show in the room, loved it, and did the pilot. Came close. And Shamath was on that episode, actually. He did the pilot with it. Oh my god. It was like my VC friend who came in and it was hilarious. It's no, it's hilarious. Um But uh I'm excited.

1:47:25 to do it. If it works out, it works out. And if it doesn't, you know, no skin off my back. Um but I like the media space and then Yeah. I This is the thing, I'm choosing to do media'cause I get joy out of it. I'm fifty one now, I'll be gone soon. Like I would enjoy I'll be gone soon. Well, you know, it's you never know. And uh you know, I've had to be friends, yeah. I have two friends who died young and I'm just like I you know talked to my wife, I was like, I don't know, like what if I make it another year or make it twenty five years, but I want to make it count.

1:47:55 I'm not going for max dollars. Like and then 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 at a point now where like literally not in the top ten. It seems unlikely. You guys want to understand my life. Like it is ridiculous and charmed. Like I can do whatever I want, I have enough money to do everyone, my kids are fine. I can have whatever I want. I don't care about like a third home. Like it's I have a ski house, I have a my regular house. It's good. I'm I'm good. My kids have their college paid for that. A hundred percent.

1:48:29 I literally do not care about what my Do you feel like that's a demon that you fight is like any allure toward No, I had it when I was younger. I want it to be powerful. I want it to be important. I want to have money. I want it to be seen. I wanted people to recognize my greatness like any person recognize me for what I do. I got all that. It literally does not even come at my radar to have more money is the last thing I'm thinking about. I do want to have I do want to you know, be the greatest investor of all time. Yeah.

1:48:55 Like to me that's meaningful or be one of the I wanna be Like I know I'm Mount Rushmore for Angels. Yeah. I wanna be Mount Rushmore for all investors. So when you guys do your thing in ten, twenty years and it's like okay, you know, here's Doug Leone and Maritz and you know, uh here's Yeah. John Door, here's girly. Like it would

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1:50:10 to how users actually behaved. So if you want to make learning your competitive advantage, whether you're building new AI experiences or just evolving your existing core product, go to statsig.com slash acquired to get started. When you guys are having the conversation in twenty years and I'm gone or I'm retired. And you're saying Mount Rocky. P yeah, I think it's possible. Um

1:50:32 I met Don Valentine when they were like, you know, he was not active investment, but when I pitched Mahalo, he was in the room, he came up, I talked to him. He was oh he was still hanging out there all the time. Um yeah, like why retire? Um He was just awesome. Oh um But you know, if you had that conversation right now about Mount Rushmore Like you gotta Okay, so Who's who's on your memoirs? Well, I mean you gotta have Don Valentine. Yeah. Right. That's just not possible but how are you scoping it?'Cause you probably need Paul Graham too. Well, yeah, I mean yeah, Paul Graham is in the running for sure. But that's like a number of startups, but there's a lot of big ones in there. Yeah, big impact. So Paul Graham's definitely in the running, but Okay, so do you go with

1:51:08 John Dor's in there along with so If you're doing firms it's a lot easier'cause you get Kosla Door And um Perkins, Tom Perkins. You get the three of them at once. Yeah. You do Sequoia.

1:51:22 Which was prone. People forget. Venezuel Kosla spent a decade at Kleiner Perkins with John Doyle. Yeah, and you and you had Yeah. So I mean you you look at that firm, it's like that's like the OK C with like James Harden, you know, whatever. But then you have Doug. Leone. Uh Mike Morris and Valentine.

1:51:41 Rule off. Well, Rollo's active all the same time. So those thirty years and it's like, well, that's Mount Rushmore, right? So if it's a Mount Rushmore of Mount Rushmore's is kinda how you might look at it. You know, you definitely have to have We just did back. You gotta have the Fab Fero the Fab Four era of Benchmark. The Fab Four era benchmark was truly something special. It's kinda like it kinda builds itself the Mount Rushmore right now, right? It's it's gonna be a Sequoia cleiner. Benchmark.

1:52:09 And then we're like We're gonna have a big debate on the fourth arm. Yeah. Like is it Well it just depends how wide we're willing to scope it. Is it like traditional series A type venture firms or is it Angelis, Naval? Yeah, that's had a huge impact. Y C in there, do you put it Y C or Techstars both have a huge impact? Do you put um You know. Uh You can argue for founders fund. You can say Y C A star is not completely different things on the way.

1:52:35 W Y C is like Yeah, for sure. I mean t I three orders of magnitude more significant. They've done the same number of companies, I think, but just in terms of returns, yes. But Tech starters, I think, was a little before Y Combinator, but anyway, you you definitely have Y Combinators, you know, in the running for that fourth spot, I guess. And then who else would you put in there? Masa? Oh your email beta. Well no, I mean but yet in in that maybe it may be now. I don't know. Excel would be in the running. For sure. It's Ron Comway. I think the way you kinda have to define it, which is unfortunate because it means that it's gonna be a long ass time before your firm hits Mount Rushmore is

1:53:11 three successful generational transitions where each of the generations would have been on Mount Rushmore. Right. So then let's just do this. Instead of Mount Rushmore, because you're we're talking firms. So for firms you do Mount Rushmore, right? So I think if you were just gonna 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 Allocat Hall of Fame, top twenty. I was trying to figure out. When we were

1:53:38 Doing the benchmark episode research, which will be out by the time this comes out. Yeah. Uh twenty four eighty Sand Hill Road. Is a very special building. It was the Fore thought, PowerPoint. The Quadris Complex. Quadrus Complex. Yeah. Office. Then it was Microsoft Silicon Valley. Everybody else who cares about this is listening right now.

1:54:06 Sebastian who wrote the parallel song. Yeah, yeah, yeah. You guys are taking this way too seriously. It's not that important. But then we're like a lone gelly in David South. T VI not official hall of fame. T VI, Meryl Pickers. TVI. That's a good deal. August Capital, benchmark capital. Shasta Capital all in this same building, and I think there's some space for rent in there. I don't wanna go live down there, but like I think we gotta take out a lease just to put the museum. We should just do it. Fuck it, we'll just do it like it. We'll just we'll do it like every year we induct somebody. We'll get up there the three of us and be like This year we're inducting This should truly be a hole. We should totally do this. You know, Cooper's town there is a um what do you call it? There it'd be our Cooper Standard. There is the computer history museum, but

1:54:53 That's for the PC, which is totally valid. No, it's not for capital allocators. It's not for people. Like there should be a hall of fame. And do we like do we Midas list style ask people for the real hard truth number? No, no, no. It's about impact. No, we decide, the three of us. We decide. It has to be impact on the game. Does the NBCA have like a lifetime achievement award? Is that the closest thing? Yeah, no, it's it's about impact. legacy like the intent of the person, like this is why like Paul Graham would be like, you know, uh first ballot. This is why you know Okay who were the first ballot And it's so obvious. We've already talked about it. Those are all first ballot. And do we have anybody who we haven't talked about or who is not obvious but would be a first ballot? If you're under twenty years, you're not like just like let's wait till you're twenty five years in. Yeah, just like the sports hall of fame, you gotta have a Yeah, you gotta be you're not playing in the league anymore. So Paul Graham's still playing in the league. Does Jeff Bezos

1:55:48 Count. Like, wow, I mean how many investments has he made? That Google investment is crazy. So there there's that, but there's also like I think Amazon is the best venture firm of all time. Just in terms of like it's internal. But they're not separate companies. But like Capital Allocating, lowercase C, lowercase A. They've been great at placing bets. But you're right, Death Basis is probably the most successful angel of all time. If you just did another Yeah, put on, you know, when you're when you're looking at I think you gotta look at impact. Like impact on the game, legacy, like so is Carmelo Anthony.

1:56:19 Hall of Fame? Of course he is, but he didn't win a ring, but he you know, it just Carmelo Anthony, right? Like or Charles Barkley. Didn't win a ring, but Okay, so then we got like Arthur Rock. Like you gotta look at like the founding father type. Of course, of course, yeah, that's no doubt. I mean that's like going back to Bob Cousy or whatever, going back to like some really like You know, people who built the league kind of situation before it became the league, right? So you got the league and you got the people before the league, you have people in the league. Yeah, you think generational shit right here, you know, Patrick Ewing. Yeah. So I think like You look at Gurley like he's part of that Patrick Ewing generation, right? Like that team Elijah on Charles Barkley generation. Yeah, you start talking about Founders Fund or Y C or Angelist, like okay, now you're talking about more modern era. Yeah. Still going, modern era after two thousand. But if you started before two thousand, it's a different group.

1:57:04 Do you notice we haven't talked about in Jesus and Horowitz in this conversation? Who cares? No, impact on the game is. Both of them are in for sure. No doubt. They totally are. I guess totally changed the game. I mean, I just feel like it's gratuitous. It's just like raising ten billion dollars, three funds a year. I want to see what happens with the crypto stuff. I think they're just an index of venture. I find it quite soulless if I'm being honest. Like I feel like it's a giant index on venture and I don't think that their hearts are super into it. Well I do think they have interesting ambitions though. I think this like That's the problem. The J P Morgan It's more ambition than Soulful. But there should be a JP Morgan or a Goldman Sachs of Silicon Valley. I don't know.

1:57:45 Yeah. Why is why does Goldman Sachs manage the money of entrepreneurs? Okay, fine, but I just feel like it's It's too pr it's it's like too premeditated and less soulful. I I feel like it's a soulful business where like your intentionality and your relationship with the founders really matter. It's I mean it's like the literal antithesis of it. It's industrialization. It's the inten yes, it's the industrialization of it. It's the it's the factorization of it. And and listen I'm sure it'll be very successful at the end of the day, all the returns will be great except for the crypto stuff. It'll be mean reversion. Because like when you get the law of large numbers, you have mean reversion. Exactly. It will be mean reversion for sure. I mean that was

1:58:24 At some point they leaked a lot of their returns and they were like not fair. That was the twenty fifteen. Well they did actually it was early. So yeah, that was stupid that the journalists didn't understand it, but there were some older ones, but it was like during that time, like you start comparing it to Sequoia or benchmark. I think I don't think it's gonna I think in the arc it will not be comparable to benchmark and sequoia. And we I mean made a lot of hay of the fact that they had uh that they made eleven billion dollars in profit on Coinbase and like I do not think they sold out of that. No they so they did not make eleven billion dollars in profit as Well, I mean it's timing is everything. We'll see. I mean It's interesting too. I mean having just done this spenchbrank episode, like the Benchmark Fun seven.

1:59:01 one of if not the best institutional size fund of all time. Just like Unreal. Twenty to twenty five. The the five hundred fluctuation in the marks on that fund and it'll probably Probably end up between fifteen and twenty five X. Maybe but like but it fluctuates up up and down so much. We live in a very vol volatile time right now. So Yeah, I like the Hall of Fame idea. It's kind of interesting. That actually would be a fun thing. We should get some space on Sand Hill and put up a No, I just we could just do it as like a dinner. We just literally have every year we get a we get a we could just start in a restaurant, but you could get like a little hall. Yeah. And say we're gonna induct into the Venture Capital Hall of Fame.

1:59:40 The following people. And uh here they are. And we just have three pictures. Boom boom boom and you just drop it and it's like these are three people and then people come up and say something about the person. And I think like you'd you we w we could do like The three Who

1:59:53 we would hope would be there. And then we'll have like sports where you have the person who's being inducted chooses who inducts them. Short. Uh in the off does. Doug. Yeah. Or whoever does maritts. Yeah, yeah. But John Parker does marit.

2:00:10 Mike chooses who you know we can have Larry and Jason Calicanus come up and be like Larry and Surge. John Dore would uh ask Bezos. I mean killer. It's a killer idea. I mean we just do Bezos, Doug and Mike. Yeah. And then You would do one in memorium. Yes, exactly. You know, whatever. Because it would be anticlimactic if the only person'cause we will induct on first and if the only person that we inducted that year

2:00:41 wasn't a living person who could attend. Yeah, you do a combo. You do a combo. Maybe it's four people a year, you know. You have to think h how do you you want to get to twenty five, so maybe it's You wanna get to twenty five to fifty over ten, twenty years. So yeah. Maybe it's three a year. In order for this to like feel good, I think you're right that it has to be about impact, not about returns. No, returns is like so. That would be like saying it's like album sold for the Rock and Hall Fall of Fame. Right. There are people That'd be a very Andrews and Horowitz way to do it as well. Oh, what's the total assets under management? You know, and it's like, okay, dude, we get it. Yeah, you can't. Nickelback sold a lot of albums. Yeah, they're the Nickelback of that. No, I didn't mean that Andrew. I wasn't talking about Andrew's. Oh God. I'm not saying that they're the milli vanilla.

2:01:27 No, there was like. There there's you know, if you were to look at Ron Conway. Does Ron Con did Ron Conway Who had a bigger impact, Ron Conway or Andreessen? Like I think it's a conversation. You know, and if you'cause Ron Combin when I came into the industry, like there was at one point I was at a

2:01:41 Um The crunchies And Ron Conway they at one point like somebody said, Like, hey, is can everybody stand up who said Ron Conway invests in their company and a hundred people. And my mind was like Oh. Whoa.

2:01:55 Angel investing's cool. I mean I wasn't an angel investor at the time, but You know, long before I became a scout, but that I always remember that moment when like a hundred inspired. Is that what like put you in business as an analyst. Yeah. What happened was I had Was your Uber investment you personally or was that Sequoisman. Sequoisman. And we were like Rulf and I were trying to figure out like Do we let people know we're doing this or not? It was like a big controversy at the time. Like we want to keep this stealthy, but I mean Travis knew, but You know, it was it was a pretty great deal. You know, it was like um at the time. Fifty fifty at the time. Yeah, they dropped it down after that. Doug Leoni was I bet like every time I see Doug Mion, he's like fifty. And they had thirty percent

2:02:38 Carry at Sequoia at that point, I think. Fifty percent carry to them. I can't believe it. Doug always this look they're so classy, Doug always made a joke would always make a joke. Fifty percent carry. Oh God. We get thirty. You get fifty. Which is fine. We get thirty. We get a lot of it. We are we're very lucky, I I think if you look at what we do. as capital allocators. I think it's a very special part of the It's a very special function in the world. I take it very seriously, as you do for the retirees you're investing about half of, but Also I was just thinking about humanity and I don't mean to make it heady.

2:03:15 But these companies do move the human species forward as 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.

2:03:29 they, you know, maybe don't have an idea of you know, um, you know, if they should even build this company. And I think the capital allocators really come in and say, Here's some fuel. You know, here, go fight that war, you know. It's feel and it's belief too. I mean like what you're saying your story about calm is not uncommon, I think, amongst founders. I mean look at I mean the stories uh about Don Valentine and Atari and other places where he was Cisco is like we gotta 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

2:04:00 So can I ask you as we start to like Drift drift toward the end of the episode here. That's your line. That's your favorite line. Drift. The drift towards the end of the year. Is this our format? Like sho is this different enough from our normal show? Should we do this what should we change? Yeah, do you like this? I think a casual glass of wine and just You know, uh if you have friends of the pod and you want to go deep and

2:04:26 talk about them in ever more casual way? Sure. Yeah. I mean I think it's a great way to just have somebody on again. You know. So if you profile somebody like I forgot that I had You had done like the first episode with me and uh that was more about my career and more details and so I'm starting to tell stories over again. It's like well let's talk about some other stuff, right? Yeah, but our audience was wide this format. Well part of 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

2:04:58 What's the right word? Our shows are about the business of tech. Yeah, no, his is intellectually. I don't know why he's in the tech Verbutta but I like the format and like Kevin Rose used to do the foundation series and like yeah, I mean long for long interviews like how I mean I think Joe Rogan stole it from Howard. And I think it's now Lex stole it from Joe. I I wanna say we say stole, I think. you know, inspired by. Yeah. So Lex is clearly inspired by Joe and Joe was

2:05:26 Uh Joe was in the running to replace Jackie Martling. on the Howard Stern show people don't know this. So really enamored. With Stern. And uh he wanted to be Stern I think, and he eventually has supplanted Stern away. Yeah, it did become Sern and so Good on him, yeah.

2:05:47 Right down to the you know serious Spotify like right down to it. He became Yeah, doing a platform. Yeah, doing a platform. Which is what Stern did. Stern had multiple platform deals. He did syndication first, then he did the Sirius X M one'cause it was a new platform and he built the plat he used his number one show to build their platform, right? Which is I think What uh yeah. But actually to bring it all the way full circle back to Charlie Rose, like Yeah, he was like a you know, bus I mean he did more than business, but like he would have culture, business anybody in New York'cause 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 of somebody who does films, you know. He would have like Spike Leon, you know, he'd have Woody Allen on, he would have

2:06:27 You know, any actress on who was doing something interesting, any novelist, Margaret Atwood, anybody was just coming through New York on a press tour. You know, you you would do your press tour. And then you would Just go chill with Charlie and you would get to do something long for him. Yeah, you know. It was like a little like sort of more jazzy. You know, a little bit more like

2:06:46 Acoustic. So I I like this format for you guys. Should listen to Smartless at all? Do you know about that show? I I have listened to one or two episodes. It's Bateman. Will Arnett. Arnett and then somebody else. Yeah, the guy from uh Will and Grace, Sean. I don't know who that person is, but They bring on A surprise guest each time.

2:07:03 And other people don't know. Yes. So they're not prepared. Yes. And it's like it's like it's like Katy Perry, it's like Chris Pratt. Yeah, it's become a big deal. I kinda wanna do that of tech. But like you and I don't know who the one of us is bringing somebody. But celebrities carry a certain charisma with them that our tree doesn't have. But maybe it but it doesn't have to be the surprise as much as like Well the the other thing is the

2:07:32 It th even though they have guests, the show is actually about them. The guest is a prop. In a way, yeah, I guess. I've only listened to one or two. You know, I see it in the rankings, like it does incredibly well. Like it's a top ten or top twenty five podcasts. Is it part of a network? Is it part of Spotify or something? I don't think so because I see it on iTunes very hard. I think so. What's really weird that like Spotify. Doesn't allow

2:07:54 Joe Rogan and Call Her Daddy on iTunes because The advertising would be huge. Right. Right so why not like take the ads in and put them over? There's some MBA that's run the numbers that says it's more valuable if it's driving new subscribers to production. I guess that's it. I guess that's it. Yeah. Oh, I guess you know what, they want to be able to have those new subscribers so when they go renegotiate with the music. I so they're doing audio books too now. That's the next piece. Yeah, that is the next piece. Yeah, yeah, they're doing audio books, one off purchases. Smart. I mean audio is great. Alright, it's getting really hot in here. It's getting hot. We're in like a sauna.

2:08:30 A new Yeah, it's a David just moved. David's got a new empty house. We we've never sort of like the shining there's no furniture. We just finish this room. It explains the smell. You couldn't I mean listen, you're rich, dude. You go on my socks barrel. Jason Calicetus. No, come on, man. I know those fees. Oh my God. Craigslist, I I love Craigslist. I love it. You buy use furniture on Craigslist. All the time. I do not buy new furniture. I bought a a temporary couch on Craigslist. No, I don't know. You're gonna get robbed. Don't do it. It's too crazy. Craig Newmark, I love you, but that our Tavanta.

2:09:15 Ovanta.com slash Acquire. Uh our thank you also you don't know who the other sponsors are because we haven't we didn't talk for them live with you'cause we like we felt very strongly that it was you know we wanted to make better use of your time. I love reading the adjunct. Do you want to read our Brexad? They don't sponsor myPods and no. Brex? Maybe they have. I don't know. There's also a lot of it. Brexit, yeah. Brex, yeah. I know. If you're enterprise, if you're global by far the best corporate spend management. It's much more than a card now. Much for expenses and everything like that, right? And then they've kind of expanded behind that. So you can give cars to each of your employees and

2:09:57 Then if they screw up you can turn it off or something. Yes, exactly. Preapproved some budgets. All the listeners know because they they heard it like an hour ago. They're very familiar with it. Oh, it's in here, yeah. So anyway, shout out Brex. So that's Brex. Shout out Brex. And then Use the promo code twist. We share We share this uh last sponsor. These are these are great folks. These are these are are like dear friends. And and geniuses and rat contours. Masterworks?

2:10:24 No no no think think smaller but bigger. Shop. Literally small. You gotta kill it. Tiny.

2:10:35 Oh tiny, of course. Yes. They're buying companies. They're buying companies. They're doing a good job, yes, they're creating like the Berkshire of the Internet. And can you imagine a better time to get the monkey off your back of Venture Capital? Sell your company. Secure the bag. Listen to the bag. Secure the bag telling you. Let's go with Jake Allies. 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. Oh man, let me tell you something. What did you do when you secured the bag? I'll tell you what happened. I the I got it's a funny story. I'm in my office. And uh got Bank of America.

2:11:14 And I got like low thousands of dollars in my bank of my account. I got an American Express car with ten negative ten on it. And I've used it with negative. five or ten 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.

2:11:30 on the thing. This is refreshing refresh. I'm hitting refresh. I'm hitting refresh. And then Bing ping ping ping pink. You know, all the numbers come in to the for the whole, you know, amount. And you own most of weblogs, eh? Uh Brian and I were equal partners. Then we had Peter Rojas had some ownership, and then Mark Cuban was our big investor. Uh and by big investor we put three hundred K in for five percent. So that was a great outcome for him. Uh wow. Yeah.

2:11:56 Uh Or more, maybe on ten percent. I think on ten percent. Anyway, long story short, uh My wife comes in. She you okay? And I said what?

2:12:06 She said. Are you crying? And I reached up and I had a tear in my eye. You're like this is a new experience. I've never had this before. And she said uh I said, She said, Why are you crying? And I said, I'll never my family will never have to worry about money again. Because I spent my whole life worrying about money. Yeah. You know, my dad had lost the business and everything. It was a very cathartic thing for me. And I think people you know, who are already rich, uh, you know, or maybe who come from means just they don't understand the concept of living with the fear. of being broke and in debt all the time and then when you have the bag you secure that tiny bag.

2:12:41 And it's a tiny bag. But it's filled with diamonds and cash. And you just open it up and say, Thank you, Tiny. Thank you, Tiny. No, it's highly they don't give us a thing. Is it high at tiny? Uh and tell them that's like just know that tiny bit. Tell them that Ben David and Jason. You should get by. A one touch express machine. I bought a Jorah.

2:13:10 One touch espresso machine, which at the time was like two grand. And I was like, This is unbelievable. Then I tried to buy a Ferrari. Uh they wouldn't sell it to me. In Barrel. You were the no new money or something? Yeah, basically. I went in there and they're like, Oh yeah, what do you am I I'd like to buy a Ferrari uh today at the four thirty and they're like, Oh, we don't have any available And I was like, Okay, can I put myself on the wait list we're not taking the answer on the wait list. So I said to this guy, Can I ask what do you do here? He's like, We sell Ferraris. I'm like, To who? No, this is part of their strategy. It's part of the strategy. We're not any part of your list. I was like, Well, how long is the wait list? He's like

2:13:51 I was like, okay. I was like, I'm a cash buyer. He's like Everybody's a cash buyer. I'm like, Okay. Um Uh Can I ask you a question then? He's like sure, come into my office with an espresso, you want some Pellegrino? I was like, No, good. And like literally offer me Pellegrino espresso and I was like uh I said I have to say more touch. Sure. And like this like Italian guy's like um I was like

2:14:14 I don't mean to be rude, but What do you do here all day? He's like, Well we deliver the cars and we service them and we sell used cars, you know, 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 preompt. I was like No no no, the one I'm looking at the four thirty, the red one out there, that's the one I want. That's got a sticker in the window. He's like, Yeah, yeah, no we we certify them we put the sticker on the window.

2:14:35 I said, Oh. Well that goes for two hundred thirty thousand dollars or whatever and So uh yeah, what do you want for it? He's like three hundred. And I was like the sticker says the potential. And I was like So you pay over seventy thousand. He's like, but it only has two thousand miles on it. And I was like

2:14:56 Two thousand miles. Seventy thousand more than new. I said, Why wouldn't I buy a new? He said,'Cause you can't get them. And I I just so I'm such an idiot from Brooklyn who doesn't understand the concept that people would pay over. the car and I I'm just perplexed. I was like, all right well let me think about it and I left and and then I was with my friend and I was like Um and I had the Rob report and it said like number one car was the Ferrari F

2:15:19 thirty and the turn of the page was Corvette. C six was the number two card. And the starting line was Make Ferrari o buy two. For half the price of a Ferrari. and beat them off the line.

2:15:31 Oh, or something like that. And I was like Let's go to the cor let's go to the Chevy Star. I walk in, there's Corvette everywhere. The guy looks at me and he goes, You wanna buy a Corvette? I said yeah. He said, If you buy a Corvette today, I'll give you five thousand dollars off. I was like, Yeah, so we go out on the four oh five and we're driving the Corvette. And he's like Is a Corvette sound like you're going seventy miles an hour

2:15:53 I'm not selling I said, I'm not he said, I'm not selling this car to you unless you hit that gas much harder. And I said, Okay. And I punch it to a hundred miles per hour. The guy's like, Yeah, how does that feel? I'm like, great. I come home with a yellow convertible Corvette, my wife's like Not to the Ferrari. I was like This thing only costs sixty five grand. It's like seventy and I got five grand off. And it's American, baby. And I'm uh that was the car that I famously Uh was according to Gawker.

2:16:23 Robert Scobe, myself, and Elon When Elon got the first P one of the Roadster, he was like I got it. I was like Oh, let's meet in Brentwood and we were driving them at a racing. We were driving them along Sunset Boulevard. Spirited drive. A spirited drive along Sunset Boulevard, and we did it like five times and Five out of five times the Tesla just destroyed the Corvette. And I was like, I'm doing something wrong and you know then we switched cards and we and I was like, nope. Electric just gonna be everything. And this was the first one.

2:16:55 That You know, first. That was the prototype. That's in space right now is the Cherry Redwood that's in space. And there's a famous photo of me and Elon in front of the space. Uh there's that that one's it, but there's a famous photo of the two of us Uh, you know, in front of my Corvette and his P one. Uh, and I remember that night like it was yesterday'cause we're this is before the iPhone, you realize. Like Robert Scobe was recording this on his Nokia, you know smartphone. These are the memories, right? Like crazy. This is the journey that you've been on. Yeah, that's pretty much. This is the stuff you just will cherish forever. My life is

2:17:28 Unbelievable. I am so grateful for it. And uh thanks for having me on the podcast. Listeners, thank you so much. Acquire dot F M slash Slack, come and join us. We'd love your feedback. This is cool, this is over there. New shtick. Quier dot fm slash store, you can buy cool shirts. Shwag. Uh slash jobs. Find your next card career experience. Craigslist. That's right. David buys you some smelly furniture. My God, it is hot in here. All right, we got to eat some food. I don't know what we're going for here. Oh so fun. Thank you so much. Of course. All right, listeners, we hope you enjoyed that uh very first acquired sessions with Jasanis. It's a new format we're playing with. We would love your thoughts. Acquire itfm at gmail.com or tweet at us at acquire itfm.

2:18:13 And uh With that, listeners. We'll see you next time. I'll see you next time.

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