Acquired - ACQ Sessions: Jason Calacanis

Episode Date: October 4, 2022

We kick off ACQ Sessions with the-behind-the-scenes story of All-in, from the world’s greatest moderator himself Jason Calacanis. ACQ Sessions is our new, occasional “MTV Unplugged” version of Acquired: a great IRL guest, a bottle (or two) of wine, and no script. We talk about everything you’d imagine we would over wine with JCal — All-In, bestie relationships, money & politics in Silicon Valley, who his influences and mentors have been (one surprise — the great Fred Wilson of USV!), what motivates him to keep grinding and why, at age 50+ when he could easily be winding down he’s instead speeding up into the most productive phase of his entire career. Pour a beverage yourself, pull up a comfy seat and join us! Sponsors:ServiceNow: https://bit.ly/acqsnaiagentsHuntress: https://bit.ly/acqhuntressVanta: https://bit.ly/acquiredvantaMore Acquired!:Get email updates with hints on next episode and follow-ups from recent episodesJoin the SlackSubscribe to ACQ2Merch Store!‍Note: Acquired hosts and guests may hold assets discussed in this episode. This podcast is not investment advice, and is intended for informational and entertainment purposes only. You should do your own research and make your own independent decisions when considering any financial transactions.

So wait, it was a magazine. Magazine, yeah. That's how I started, yeah. Magazines was like the original platform for... Wait, have we started? Silicon Alley. I guess we started. This is the trick.

We've just been recording the whole time. We just started, yeah, the whole time. Yeah, but... Welcome to Applied Sessions. All that stuff that you said beforehand that was really juicy, I don't think we should put that in. No, definitely not. Definitely not. We don't know. Welcome to Acquired Sessions. All that stuff that you said beforehand that, like, is really juicy, I don't think we should put that in.

No, definitely not. Definitely not. And 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.

Great to know you, boys. So this is the first Acquired Sessions. Acquired Sessions. I feel like I should should get out 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 you know it's awesome but uh really for folks like you who we know really well, what happens if we throw out the script? And just chop it up.

And we just chop it up. David Rosenthal unplugged. Wow, I love it. I love it. It's just literally MTV unplugged. Literally. Okay, listeners, now is a great time to tell you about longtime friend of the show, ServiceNow.

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and make work better for everyone. Yep. So learn how you can put AI agents to work for your people by clicking the link in the show notes or going to servicenow.com slash AI dash agents. That's great. So, well, we have no agenda, obviously, but... Wait, where do you want to start? We got to think Vanta. Oh, yes.

Oh, Vanta. I'm an investor. We're investors too. Well, great. They're an awesome company. Big supporter of podcasts. So yeah, go Vanta. We are huge fans of Vanta and their approach to the whole compliance process, SOC2, HIPAA, GDPR, and more.

And we've got CEO and co-founder Christina Cassiopo back with us today. Vanta was already the best place to check the box and get security compliance certified. But now you've just launched Vanta Trust Reports, which take things even further. Tell us about that and how they can help companies deepen their relationships and trust with their customers and partners over time. Really excited about this. It's actually a bit of a not yet told Vanta history, but something like Vanta Trust Reports, honestly, a much worse, much more poorly designed version, but yours truly, which is why I can say that, were launched in the very early days of Vanta when we wanted to help companies get secure and prove that security. But weren't yet convinced we wanted to or had to go all through the nuances of what a SOC 2 was.

So we figured, hey, let's just make this report of the best security practices. Let's check companies against those practices all the time and make this live and updating, visible and transparent. This should help these companies prove their security and grow their business. And it should also help them be more secure because they've got this report, like this kind of security status page out in the wild. So 2017, Vanta tried this and found out that no one really knew what a Vanta report was. And everyone wanted a SOC 2. So flash forward to 2022.

And it's actually really exciting. Turns out creating standards is, you know, people have to know who you are before you can create your own standard. A little bit, you know. And so honestly, like, I'm joking, but I'm not. Like, literally, the company strategy on that day sort of became, okay, use the existing standards to bolster yourself and build something better here. And so this launch of trust reports is really exciting. These are companies that maybe it's before they've gotten a compliance certification,

maybe in their process of getting one. For some, actually, it's they they've gotten a compliance certification, maybe in their process of getting one. For some, actually, they already have one. But then rather than keep going through their buyer's process, they're like, look, this is just constantly up to date and has all the information you need. You know, take a look at this instead, rather than my, you know, compliance PDF from months ago. So relative to a SOC 2, which is done once a year and kept up to date annually, a Vanta trust report is kept up to date to the minute, basically continuously. You always know what the company's practices are. So just really excited to get this out into the world and into folks' hands. Our thanks to Vanta, the leader in automated security and compliance software. If you are looking to join Vanta's 2,000, nay, 3,000 customers

to get compliance certified in weeks instead of months, you can click the link in the show notes or go to vanta.com slash acquired for a 10% discount. Thank you, Vanta. So in the juicy stuff earlier, you mentioned Mahalo. Yeah. Is that why you started the podcast? Can we just keep referring to the juicy stuff? Yeah, the juicy stuff. Yeah, no, we weren't don't know is that why you started can we just keep like referring to the juicy stuff it's yeah the juicy yeah no we weren't talking

about that stuff yeah yeah is mahalo why you started you went from print to print to well when i in the 90s um you know i grew up in brooklyn um my dad had his bar uh seized by the feds because he didn't pay his taxes during the 1987 crash he became like he got behind and the fed showed up one day and this was the maybe six weeks before i was set to go to college and he said hey son i can't help you with college good luck 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, you know, state liquor authority, they kind of take it serious. So feds come, shotguns, the whole thing.

They seize the place. They seize everything in it. And I was like, well, I guess I'm going to school at night, and I'm going to work during the day. And I worked fixing laser printers. And that was like a really good racket. The HP had just come out. Were you set to go to college somewhere else? Well, that's another story. But I was set to go to Brooklyn College. I got into that.

I had also taken the police exam to be a police officer. So my brother went into the force. And then I said, you know what? I'm going to see if I can go to college and make that work. So I'm going to Brooklyn College. So I decided to work during the day. And then I said, you know what? I'm going to see if I can go to college and make that work. So I'm going to go to Brooklyn College. So I decided to work during the day and then I went to school four nights a week, 6 to 9 p.m., carried full credits, 16 credits a semester. And I would work fixing laser printers all day. I was a bad student. I was always that student who underperformed.

I didn't find great meaning in academics, but I had a computer when I was in high school, and I was more interested in playing with my 300-baud modem, which then became a 1200-baud modem on my PC Junior. So it kind of, you know, like many people of that era, we were sort of set on a path because we were the first generation to have a computer at home. I actually had an Atari 2600, and it could play Tank,

was the game that came with it, and Pong. And so my dad bought this for us when I was six or seven years old, 1976, 1977. And he had one of the first Pongs in Brooklyn in his bar. He must have cleaned up on that. Oh, my God. It was crazy. And so I just got exposure to video games and computers. And I was like, wow, this is incredible.

Computers are going to change everything. And then I happened to hack some software. used to i ran a lot of scams uh but uh you 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 10 bucks and then we started like hacking and doing what was called phone freakings when you were doing this stuff like it's you to be reasonably technical to do it not like the you know not like wasniak technical but like you we soldered chips sometimes we changed yeah like 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 you consciously ever make a fork

where you were like, not tech media? And of course, media about tech, but you're like, I'm not going to be the guy doing the boards. I'm going to be the guy writing about the people doing the boards. It's a very good question. I used to go to Bleaker Street. I used to hang out in the West Village or the East Village. It was like the cool places to hang out. And like a thing to do would be to go to tower records and look at the zine

section so there was a concept of a zine which was short for magazine but a zine was something you wrote with your friends you printed it yourself at a photocopy store it's like blogs before blogs blogs before blogs and i created a zine i was like i'm going to be a magazine publisher so the first one i did was cyber surfer which was about dial up magazine dial up services and cd-roms and i did it with my friend brian alvey 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 90s i did which is gadget twad all that stuff yeah everything you sold aol i think i sold aol but anyway before that i did this mag i did that magazine and then i had met fred i met

jerry colonna at uh internet world the first one and he there was a booth that's right when jerry was a vc before he was like the before he was a vc he was consulting for lycos and i think cngis and so there was a Lycos booth. And I had met this young lady at it. And we hit it off and we're talking. And then she introduced me to Jerry Colonna. And then I met Jerry Colonna in an office no bigger than this room on Union Square. And he said, listen, I'm leaving Lycos, but I'm going to start this Hack Me Ventures with my friend Fred.

I want you to come read business plans for us. And so I met Fred Wilson. And I would go up to them and they were doing, J.P. Morgan was going to back them for their venture firms. This was 1994, 95. This became Flatiron. It became Flatiron. J.P. Morgan was the first big anchor of Flatiron.

They were half of it. And Masayoshi-san, SoftBank, was the other half. No way. So they wanted you to come be a VC associate. Not a VC, just to read business plans. So the deal was, they would take me for sushi and pay me $1,000 to read business plans. Wait, what do VC associates do besides just read business plans? Exactly. Well was they would take me for sushi and pay me a thousand bucks to read business plans. Wait, what do VC associates do

besides just read business plans? Exactly. Well, anyway, it was a thing. And so I had the magazine started, Silicon Eye Reporter, and they were paying me. And so I read about this Beverly Hills Internet Company,

which got rebranded as GeoCities. And I wrote a little coverage of it and I said, you should invest. I'm 24 years old. I don't even know what VC is. That's where Flatiron made all their money. Yeah. They were going to invest anyway. Flatiron became

USV, right? Yeah. Square Ventures. Flatiron went with Jerry Colonna then when Jerry decided he wanted to move to Colorado and just chill. Yeah. He had made enough money I think. Coach Founders. Coach Founders I think. And yeah, maybe he had like, I think he's been pretty public about it. Like, I don't want to say a nervous breakdown, but a

kind of like, maybe a fork in the road. Like making a decision about what you want in your life kind of situation. He wrote that pretty public about it. I don't want to say a nervous breakdown, but maybe a fork in the road. Making a decision about what you want in your life kind of situation. He wrote that great book about it. Yeah, yeah, yeah. And so Jerry was a good mentor. But Fred actually became ultimately my deep mentor at that time. And Fred said to me, listen, you're doing Silicon Valley Reporter. You're writing about us

and the companies we're investing in. And you're doing stuff. Which would you rather do? And I was like, I think I'll do the magazine.'re investing in. And you're doing stuff, which would you rather do? And I was like, I think I'll do the magazine. This was before. Now it's like, I do both. And now it's like, I do both. Why choose?

But just to back up to GeoCities, that sold to Yahoo for like $3 billion. $5 billion. And Flatiron was the main investor. Yeah, Flatiron maybe owned 5% or 10% of it at the time. It was like a huge win for them. I mean, Fred was on fire. For a New York VC and Jerry, they did pretty well.

How did that happen, right? I mean, Silicon silicon valley was here but they were in new york like what was going on yeah we just there was a lot of good companies brewing in new york and my concept with silicon valley reporter was well they have red herring in the bay upside in the bay but i own new york and i had silicon reporter and then i started one called digital coast reporter in la so i had two two conferences, two email newsletters. That's kind of king of New York, right? I grew that business to $10 million in revenue off my credit cards. And had 75 to 100 people working for me when I was 27 years old. And I didn't know anything about how to run a magazine, how to run ancillary.

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

you were the equivalent of like satoshi or something like it was crazy to be yeah the new york internet guy um can I so we talked all about a lot of this when we did our like big jason cal empire of jason calacanis episode with you so i want to like yeah put this on pause so yeah sure people can go listen to that you should it's great we get like the detailed story of like weblogs inc and all that great stuff and you mentioned i want to like take us from you're only as good as the you know your greatest your newest thing sure um because the last time we talked to you you 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 happened with all in how did i mean it's weird

has it surpassed your wildest expectations um i thought it would be something chamath and i would do 10 times yeah so the the origin story is pretty simple um chamath uh i knew because he was running icq chamath was running icq at aol and i had sold my company aol and that's like the revolving door i don't know that lineage it was was like Ted Leonsis had this March to a Billion, my Greek brother, a mentor, had this like March to a Billion off-site. And so I went to this and I just sold Weblogs Inc.

Like a million AOL users? Hot shit. That's the implication? That was the idea. It was that, well, with Weblogs Inc. and with AOL and other assets

they wanted to buy, they were going to March to a Billion users. Yeah. It was like this crazy rallying cry. And we had these t-shirts March to a Billion. So I go to that and I see Chamath and I was like, hey. And he's like, hey. And we introduced

each other and we had known of each other and I was like, what are you doing here? He's like, I'm running ICQ into the ground. I'm just writing it down every month that loses a million members. It's hilarious. And he's like, yeah, but I'm leaving. I'm going to go to the West Coast. I'm going to go work at this VC or whatever. I was like, all right, nice seeing you.

And so then when he was there, I was in LA. What VC did he go work? Because he was at Facebook. Mayfield. Mayfield. Mayfield for a year. And then Sean Parker introduced him to Zuck. And Zuck needed, you know, like a Chamath.

He needed, like, somebody who would just. Chamath built the growth teamath he built the growth he built the growth team and he's like i don't there is no equivalent of growth that was the idea of growth hacking didn't exist as a term until chamath did what he did he said just find me the smartest people i'm hiring based on iq and i'm hiring based on desire to make a lot of money and be a beast and he just went he went into beast mode because he, too, was very hungry. But you guys must have been like brothers from another month.

Yeah, for sure. We're definitely both outsiders in Silicon Valley. And I had Chamath come on the pod, This Week in Startups, that is. We listened to it. It's fun to go back to that moment. You can see how he's not

polished. He's not you know polished he's not Chamath you know as Gregarious or whatever he's a little more reserved he doesn't have the loro on no loro piano

was he in great shape or no not one of those he was like a he was like a dork you know but he was

he was Bezos pre no he was like Bezos pre yeah whatever you know he he always was a poker player. He used to play in Atlantic City.

So he was, you know, like myself, an outsider who wanted to take risks and wanted to win. And, you know, confident, you know, even maybe more confident than both of us should be. And so I kind of introduced Chamath to the world by convincing him to come on the pod, which he was 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 L.A. He came on the pod, and then people, I was like, he's really good on stage. He's funny, whatever,

and so. Which at this point, you had an eye for, because you were like. Of course. I mean, one of the things when I was a podcaster in those early days,

I'm talking about 12 years ago, whatever, is I introduced a lot of people to the world. I think like 14, right? 14, yeah. I introduced, one of the things when I was a podcaster in those early days, you know, I'm talking about 12 years ago, whatever, is, you know, I introduced a lot of people to the world. I think like 14, right? 14, yeah. I introduced people to the world. Yeah. Yeah, it was 2008, I guess, whatever. So I introduced a lot of people who were in tech to the, you know, and it was only a couple thousand people.

And then as now, too, like, you could be a great founder, you could be a great, you know, person in tech, tech. But that doesn't automatically make you a compelling podcast guest. As we know. No, of course not. No, I mean, I have my own theories about what makes for a great guest. We'll put that on the side for now. But anyway, we start a friendship. We start playing cards together. We start hanging out, trading notes kind of thing.

And he's going to start his venture firm. I'm a scout at Sequoia, all that stuff. We start playing and trading notes. And we just become great friends. But then he was coming out of CNBC one day. And he's like, oh, my God. You know, just like we have such a good rapport when you interview me. Because he had done a bunch of interviews with me on stage and stuff like that at my events.

He's like, I want to do a podcast with you. I was like, yeah, you can come on this week and start up at any time. It's twice a week now. Which it's now five times a week? Six. Six times a week. Dude. Plus I'll see. i may go back down to

five next year it's a little much right now yeah dude you i mean we'll come back to this but you're killing yourself right now and you're on act three yeah i have more energy now than i 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 20s but for different different reasons, different type of energy. Anyway, Chamath calls me, you know, coming out of the studio. I don't know if he was in New York or if he was in the One Market one in San Francisco here. But he said, I want to do this pod with you. I said, okay.

And he said, I want to do a new pod with you. Just me and you. We talk. I was like, sure. He's like, what should we call it? We're texting back and forth. I was like, we should call it All In. And this is 2020? Yeah. It's like two years ago or whatever. And I said, yeah, we should call it all this is 2020 yeah it's like two years ago and I said yeah we should call it all in like we should come with the poker name he's

like yeah great like a raise or something's like all in cuz you were you'd been referring to this poker game on air on talk about it once in a while the poker game that doesn't exist and yeah 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 I read 20 years then Chamath had had a poker game with Brooke Hammerling, the famous PR person, at the Code Conference, which was the All Things D conference before that for 20 years. Then Chamath had a poker game. Saks, I had hosted it floating and putting all that together. Yeah, I'd referred to it many times in the pod, but tried to keep it from becoming public.

But it was me, Bill Gurley. It's all public now. Mark Pincus, right? Pincus used to come to the code one yeah um which is another funny story um and uh lots of funny stories in my life but anyway um so then the pandemic happens and we're like where are you going just dropping these little red cards we got to pick them up on the way yeah at some point we got to pick these up anyway at some point i'll write a biography. Anyway, nine years. Third book.

Anyway, the pandemic starts to happen. We're like, well, Sax has some ideas about masks. And then Friedberg has some ideas. There was no besties originally, right? It was just you and Chamath. And I mean, in truth, like, Friedberg and I weren't besties before All In. I mean, we knew each other. We were friends, but not besties.

I was besties with Sax and Chamath, and now Freiburg is a bestie. And, but he played in the game, obviously, and we had just started to have a developer friendship. But anyway, that foursome kind of clicked, right, pretty quickly. And I think, you know, I was a really good interviewer I'd studied interview techniques and really you know after doing whatever I'd done at least a thousand episodes of Twist

at that point and I had had Sax on many times and Chamath so I was very comfortable with them and at the poker game we break chops and I make jokes and Chamath's a great host and we're just very comfortable with each other and Freeberg kind of joined that group, and it clicked.

And I think during the pandemic, and I thought maybe this last 10, 20 episodes, but during the pandemic, I think people wanted information. And I realized- And perspective. Sure. I think that's a thing.

I'll tell you, I never expected to be listening to david sacks talk coming from where he comes from politically and where i come from politically and going yeah that is a good point and that perspective is like so helpful in our polarized world today yeah it's very unique and you know around the poker table we all listen to each other we're friends but the world does not want us to be friends in some ways the world wants us to be enemies and i kind of think about it like um you know best of the enemies kind of situation like we debate specific things like uh gorvodol and um who is this advertiser yeah anyway it's a great documentary about

gorvodol and um who's william Buckley. They're just two public intellectuals. One was on the left, one was on the right. And there's this documentary, Best of Enemies. In the 60s, they started debating different political conventions. It was the most compelling thing on TV. But they were like friends. Best of Enemies. They weren't besties like Saxon and I are.

But, you know, Gore Vidal was just, he was gay. Kind of closeted or quietly gay and on the left and buckley was like a serious conservative and they went to blows sometimes on the show like at one point buckley i think he called him like a sissy or something like really like derogatory as a gay man and the world didn't understand he was exactly gay it was like sort of time period in the 60s where like maybe some adults understood like yeah that's a gay man but we don't say that's when they got into town yesterday we were driving the castros right here by and we saw a naked guy in the castro and i was like oh naked guy in the cat and ben was like what is going to like dude you gotta understand in the castro like huge jacked dude walking around and and super sunny so he's like just

all like slick down but did he have his shoes on was he wearing combat boots they usually wear boots yeah and then they usually carry a sarong there was a big debate when i first moved up here because there was a number of folks who used to like to get a starbucks and they had to like negotiate and they were like how about a sarong in starbucks because you're gonna sit right right bare ass and for for context for you know i've explained this to ben but like this is a thing in the castro in san francisco it's a cult it's like uh now it's like you see it's like ah this is like a relic of the 60s 70s it actually was pretty awesome because david we're like driving up and david goes oh a naked guy it was was the most warm-hearted. I had to adjust as well as a New Yorker because as a New Yorker, if somebody's naked, that's a sign that there's about to be some crazy person in a fight and police and chaos.

And here, it means high fives and right-ons. But growing up in New York, if somebody takes their clothes off on a public transportation or in a cafe, people are getting a baseball bat and calling the police and the shit's about to go down. Oh my gosh. And then here it's like, high five and live your life. That's one of the things I love about San Francisco. But anyway, the pod's gotten very big. So you get the gang together and why do you think it works?

Why do you think it works? It's like the number one ish tech in our business is number one of course but it's number it was number 28 last week like in the world you guys have transcended like this is more than just anymore yeah it has nothing to do with finance or tech anymore it is we're 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 at i was you know skiing in tahoe and i you know i was with my kids and it's hard to get a table type situation i was like hey i hate to be a pest but i see you're wrapping up are you and no pressure but are you going to be leaving soon because i'd love to camp out here and

get your and they're like stop busting my balls and the woman looked at me and she goes j cal and i was like oh have we met and she's like no i listened to your pod twice a week i'm like it's only on one she's like i listened to it twice and i was like oh my god that's so nice she's like no i listen to your pod twice a week i'm like it's only on one she's like i listen to it twice and i was like oh my god that's so nice she's like i was like are you in the industry she's like i'm a dentist wow reno and i'm like you're a dentist in reno's can i ask how you found out about she's like i don't know like she's like i deeply care about san francisco politics no it's not how she had found it and this is you know during the pandemic situation then that's when i realized it had crossed over was there a moment for you either you four or you where you were like whoa this is you know i've been um micro famous you know micro celebrity multiple times in my career but this is york yeah not for me you know and i

got a lot of famous friends uh you know i i'm used to getting recognized i'm used to people taking pictures what i'll say is like where it used to be you know if i go to austin or new york people would say i would have three people stop me on the street a day if i was walking around in new york now it's 20 you know or 10 and they want to take a selfie and it's you know just you're not podcasting is you guys get recognized and it creates a level of intimacy with people. Oh, for sure. If they're in the habit. Yes.

Because you're hearing people every week. And then people become characters. And I try to make everybody, I was, you know, in all honesty. You mean people on the show or people in the audience? In all honesty, I did craft with All In. I was very premeditated in creating some character. I've never really talked about this. Yeah, yeah, yeah. But I crafted some character kind of arcs i the fights are all real trust me there's

nothing scripted about that but i did say like i think i can as the point guard here kind of shape the conversation and i literally created the character of the sultan of science right as i was gonna say and you know freeberg didn't even have a twitter handle well there's zero followers there's even a character of jcal on all in like there's the world's greatest moderator sure yeah i think more like jcal the guy who lets himself be the punching bag because it plays for the show a little bit uh which is rather not if i'm being honest i'd rather not be 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 you're like not by much like 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 It's okay with me. I could have a plane, I guess. I could get one. 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. But you do let yourself play that role of 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 make it.

I actually never wanted to play that, actually. No, that was just the boys breaking my chops, maybe. So maybe it's a little bit of them wanting to maybe take the piss out of me a little bit, which is fine, because I give it as good as I can get it. But I think that's probably for them, and you can ask them when they're on the pod,

I think for them, that's kind of the 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. Maybe let's flip it. For them, before All In... I mean, Chamath had a little bit of a public business. No, they were not famous.

They're all... This is a new thing for each of them to hit this level of notoriety. It's not for me. What do you think for, I mean, we should ask them this. Sure. Like, if you were to speculate, caveat that it's speculation. What do you think for them All In has, like, done? Well, I mean, for Friedberg, nobody knew who he was, except if you worked at Google or you were in VC.

Like, he's very connected in those circles. What's that? Or Monsanto. Or Monsanto. Like he's very connected in those circles, but he was kind of under the radar guy. I think really by design, he didn't have any desire to.

So I think it's probably the biggest adjustment for him. The increase in profile has certainly been the highest for him. And he's loved. There was a moment when i like jokingly said to people during the q a session at all in summit uh you know just say who your favorite bestie is and then direct question and it was like five in a row sultan of science and it was like oh my god what have i done now i've created this monster you know and he at the time like would barely show up for like you know he would show up for two out of three episodes he'd be

busy it wasn't a priority for him right so i'd be like all right i'll put brad kersner in if you can't make it i'll try to get bill girley to show up or whoever draymond to fill in for him you know and it was always like i wonder if freebird will show up but he's actually really committed to the show now um for sax he was high profile but nobody really knew him as a republican so he kind of uncloaked as a republican on the show well i feel like he was also like he was almost even more so than any, you know, well, not you, but he was high profile if you knew about the PayPal Mafia. But he was like the least kind of public of the PayPal Mafia. Of the PayPal Mafia, you would say Elon, Reid, Hoffman, Peter Thiel, Max Levchin, Jeremy Stoppelman, Chad Hurley, Ruloff. Yeah.

And I guess Sacks would be somewhere in that strata of like being known. Not success, being known. Being known, yeah. Being known. But yeah, you know, and I think part of the reason this works is Sacks, I think Sacks has probably taken the brunt of the head of the pod. Yeah. Because he is so passionate about, you know, a lot of topics that maybe are unpopular in the

tech circles so i do think like it's cost him deal float on the margins probably i think there's probably i don't really margin i wonder i wonder he said that jokingly on the show i don't know i'm just thinking like maybe there's somebody has ascended because he's done all in in a way that. I guess. Yeah, sure. I'm trying to think if like would, is there a founder? I wonder. I don't know this, but is there a founder who's a young founder who would say, I would never take money from Peter Thiel's venture firm because I'm so liberal. For sure there are.

And those people feel that way about Kraft now. But for every one of those, there's 10 more who know about Kraft now. I kind of agree with your position. Yeah, I would agree with that. So anyway, I do think like he's joked that it's cost him deal flow. I don't know if it has. I think truly the benefits are— The pod, too, I think for people in America and people in tech, has moved, I think, a lot of people towards the center.

I think a lot of people were moving towards the center, and we codified it for people. We maybe made it okay to admit you're a moderate. Yeah. codified it for people. We maybe made it okay to admit you're a moderate. I've been telling folks from the beginning, I'm an independent and a moderate. I voted probably Democratic three out of five times, four out of five times. But mostly that's a function of the fact that I've lived only in New York and California in my life where you don't really get many Republicans or moderates. But I voted for Bloomberg, Giuliani, when Brea was crazy, and Pataki, who were all Republicans. It's insane to me that that is the same Giuliani.

Were you here during the Schwarzenegger era, or were you still in New York? No, I wasn't, but I would have voted for him. I like competent people, and I supported Bloomberg for president, which got me a lot of flack. Really? I don't understand why. People were very upset that I was for him instead of whoever i think you guys talked about this on the pod that like oh what was the two by two quadrant of like whatever it was we all think we are here in silicon valley which is like social uh liberal

fiscal conservative yeah we were like everybody should be that but we're the smallest of the four groups yes it is a small group i i um i I think I believe in competence and staying out of people's lives. So, you know, it's very hard to know. And then even David. I mean, this is, I think, when David and I fight on the pod, which some people love. And I think some people probably turn the pod off when that happens and they don't like it. And certainly the MAGA group has no love lost for J-Gal. I'll tell you that.

Like, my replies have been really crazy I would get like brigaded the last couple weeks nuts it's funny but it's also like on the margins like they can get a little scary like they'll dox me sometimes and you know that's not fun

a handful of times it's happened but you know I had to tell David like David I am not like, I don't actually listen to MSNBC and Rachel Maddow to get my information. And by the way, you're pro-choice, pro-gay marriage, anti-war. Yeah, he's the dove. And I was like, well, okay, if we don't play this game i'm gonna just dub you david the dove and now you're making me into jason the hawk like what are we talking about here like um but anyway you know it just goes to show how silly the coalition building is like

it's totally silly exactly the the two-party system requires that if you feel very strongly about something yeah then you're not allowed to think independently about anything else it's so crazy you know i and i think independently about anything else. It's so crazy. You know, and I think what messes people up is the fact that I actually just think Donald Trump is a horrible human who you should do no business with, has no business being in any political office, and, you know, is just horrible on any number of levels. But I believe that independent of his party, he's a Democrat, obviously. Obviously, yeah.

Yeah. And so, like, I would hate him as a Democrat or a Republican. So it's not personal. And I would love to see- Or it is personal with him, but it's not- It's very personal with him, yeah. I mean, I just think this is like just horrible human being on, you know, in every way. Now, I understand for some people, he represents change.

For some people, it's like the way the Republicans secure an office and that's all they care about is winning. I get it, whatever. And I think so much of the human condition is like being a part of a community. And he, for so many people, is a symbol that means, hey, all my friends and neighbors, we 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 the tribe. Yeah, we don't, you know, a lot of people don't practice religion anymore. And so he's their religion and Hillary Clinton or Elizabeth Warren, or Bernie Sanders might be other religions and or the new iPhone, like I found myself ordering this phone, and I love it. And it's the iPhone 14 Pro, and it's

magic and whatever. But like, it's not that different than my old phone but I got to participate in all the fun watching of the keynote and the tweeting and the nerding out and like Let me look at the image quality versus the old one. I gotta say 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 you know through a lot of the trials and tribulations shown that you can be friends disagree and learn from each other and have a vibrant debate which is how we all grew up i think when i say we including you guys but also

specifically the besties i want to be friends with people who I disagree with. I want to debate stuff, right? And then people are like this guy, Dean Preston, and he's like one of these supervisors here. He's a super idiot, like guy in San Francisco who won't let them build housing and all that stuff. And he's like, you're just a conservative, blah, blah, blah. And I was like, you don't actually understand who I am. He's like, you're a conservative blah blah and i was like you don't actually understand who i am he's like you're a conservative billionaire i'm like wrong on both accounts but thank you for the latter my besties remind me on the ladder not trying to be a billionaire thank you um and uh on on that what another thing that's really

fascinating to me about all in yeah and you guys is before all in and maybe it's still to a large extent i feel like silicon valley has this weird relationship with money like super weird relationship with money like you know remember there's a whole thing about like zuck drove like an acura sv that all came from, that all came from David Filo and David Filo and Jerry Yang were driving their old cars to work. Right, like the cool thing, like you could like make money, build a company, but like you never want to, like you never.

Be understated. You guys, I think are the first like, like you guys are like, fuck, like we got a private jet. Like that's fine. Like, you know. I mean, listen, I, you know, I believe in capitalism.

I think it's great if people create jobs and if they get rewards for doing so, fine. Literally, the book I'm writing, my second book right now I'm writing is about wealth and money. But not in my regard, but in a sort of big picture societal regard. So I've literally been thinking about this topic a ton. And I think we worry a little bit too much about wealth creation with a small outlier wealth creation. And we don't think enough about inspiring people to create companies and learn. And the time I create the most controversy is when I'm like, I believe anybody can do it. And people are like, you're so wrong. And I'm like, am I?

Because I go on YouTube and you could type in any topic that you want to learn and you can learn it. And all the stuff that was at MIT where I never got to go and Stanford and Brown is online for free. And I listen to macroeconomic classes and AI classes. When I'm like, it's 10 o'clock at night and I'm doing my email, I'll just put one of those playlists on from MIT OpenCourseWare. And I'm like, I can't believe I can take a course at MIT for free anytime I want. And then you can build a business there. Like David Senra over at the Founders Podcast, like, Mr. Beast, MKBHD.

The world has never been this equitable. Yeah. But people want to spread a narrative that the world is unfair. And, like, I watched the world become so fair and so just and so much information and opportunity become available that I'm like, wait a second, I could never figure out how a term sheet worked and nobody would share their term sheet. And now there are a thousand videos and blog posts on how to negotiate your term sheet. The world is still unfair. I think, very. I think the key insight is like, recognize that the world is unfair. And actually what that is, is a game on the field and figure out how to play the game on the field. But I mean it's never been more fair.

So the world is unfair. True statement. And in America it's never been more fair. You can learn. Google has like five courses online. I think it's called Grow with Google or something where they're teaching how to be a ux designer how to do this how to do that And it's free So that they can get more people to apply for jobs and the average job

Entry salary for these things is like 80k so I I find it's very weird in the world I think there's like a group of people who want the world to be more unfair Than it actually is because it makes them feel more virtual signaling goodness well that's their community that's how they find that there are other people who love that they tweet that the world is unfair so they and they have to and it typically like is a certain type of person i'll just leave it at that okay can i so i'm going to your question founder university

now i have a course where i teach people for 12 weeks, or I should say I have a team that teaches it. And I'm going to actually teach it myself, this next cohort, where I just teach people how to start companies. All right, let's plug it. How can they find out? Founder.university, that's it. There you go. Yeah, I mean, basically it's free. The way I did it was you apply.

If you want to build a company, you pay $700. If you go and you get to week 12 we charge your stripe back the card back the 700 bucks if you don't come or if you don't have an excused absence if people miss something because of their kids or whatever fine but we just try to get people to complete it over 90 people complete it that's cool so and then we're investing 25k and some of those folks to help them start their companies like people don't know all the work i'm doing like quietly but like 200 people go to this course now maybe i'll have 400 in the next cohort the fourth cohort we'll see but you know like people can learn how to create companies and they're like no they can't and i'm like yes

they can like you have to have gone to stanford i'm like no i'm invested in 350 companies like maybe five percent of the founders went to stanford like no that's just not it's patently false like you, you know, you have some confirmation bias. You're dealing with a data set from 10, 20 years ago. I get it. But I'm telling you, like on the streets, ground level truth. We all meet with founders all day. It's never been more diverse. It's never been more open. 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 post pandemic. All people care about is like, show me your metrics. Show me the product. Show me your team. What are your skills? Great, let's go. What's your growth rate? It's basically become like as beautiful of a meritocracy as I've ever seen.

And man, you say the M word, it freaks people the fuck out. I'm like, why is it so scary for you that Silicon Valley is a meritocracy as i've ever seen and man you say the m word it freaks people the fuck out i'm like why is it so scary for you that silicon valley is a meritocracy and they're like because it's not and i'm like it kind of is can i can i answer your question earlier of what why i think all in works yes all right go ahead so i think you're the you've got the perfect storm of three things the first thing is there is on this out there by the way billionaire born 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 I don't think we've done one from a jet but yeah there was definitely two boats in the last two years that's true in some peak moments of all in it's like watching billions in real life it's like you hear you hear chamath talk about this spread trade and you're like this guy's got a lot of money on that spread trade and like does he actually have a key insight here or

is he and like there's there's this interesting intrigue there so bucket one is like billionaire porn bucket two is uh by the research you guys do and and the folks that you each work with because there's definitely researchers that seem to be involved you bring things to the table that are like brand new insights that aren't widely available yet so i feel like i was learning things about covid19 on all in that i wasn't getting through any other source i'm like somehow this is not making it to me and this feels very like a lot of it proved out to be like this was good information before it was mass all four of us are information junkies with a lot of research and teams that company how many people all in how many people touch an episode of all in one

producer nick that's it. No, I mean, but like the research, the like the rest of it. I don't know. I'm pretty sure. Are the text files open on people's computers when they're talking? We have a docket with the notes,

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

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

Yeah. And you guys are young still, but imagine you do that for 20 years. You're going to get smarter. You're a journalist for 20 years. You're going to get pretty, I wouldn't necessarily say smart, but you'll be informed. And if you're hearing the right pitches, you actually are getting cutting-edge information before it's widely available.

Definitely. So, okay, that's number two. Yeah, we probably have a slight information edge. Yeah. Certainly a huge, I will say, the information edge compared to journalists. This is not a dig to my journalist friends. I was a journalist. I had 75 people at the magazine.

We were always trying to figure out from the principles what was going on and tell that story. But we were only as good as our access to information. And we probably, now looking back on it, I think we had between five and 35% of a story. And I know that's probably triggering to a lot of journalists that they have that little information. You weren't on the inside. But you weren't on the inside. So when you're on the inside, you have 100%. Even on the inside, you might only have 50%, depending. You get enough to run with and you feel like okay now there's enough story

here let's do it and 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 yep which the third component you think makes it successful it's the thing that david and i took forever to realize works about acquired which is relationship and charisma yes like people like having fun by listening to stuff sure and so like if we can make history fun then a little bit of joy goes a long way four hours of us diving into stuff you would never read in a book and you guys do that in spades like and it's just so fun to like temporarily join your world i mean the fact that you as a

podcaster who makes elite content like top 100 content find it compelling is just yeah that's very um listen every week don't miss it i can't literally walk in the baby up and down the hills listening i mean i have people tell me they listen to it twice they take notes i'm like wow that's great you know i i don't think maybe i should take notes 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 shoot the ball and i can do both i'm a combo guard. How did the Freeburg host episode come about? So one week, you switched roles. Well, he was like, I think this could be done better.

This could be better. And I was like, go ahead. And I was like, sure. I'll just shoot. You passed the rock. I was like, yeah, you want to be a point guard? Go ahead, show us. And he did a solid job.

But let's be honest. It's not a point guard. It's not Showtime, that's for sure. Yeah. Like, I don't think people are going to go to watch him play point guard. I mean, he did a serviceable job. Put that on his tombstone. No.

But he shines when I created Science Quarter for him to shine. I said, bring me a sign. He's like, oh, you know, I don't know if I want to talk about politics. I was like, listen, Sachs wants to talk about Carnivalist politics. I'm giving him his red meat. Here's your quinoa. Come to me with a science story, you know, and we'll do this quinoa corner kind of thing. And I made him the Sultan of Science.

So good. You know, it was a distinct effort. I really wanted to make him shine, you know, and it worked. You know, it worked because you see how engaged he is and what used to happen was and fans know this i'm not speaking out of school here you see it every episode sax would disengage during science and quinoa disengaged during politics and what i've been trying to do is keep both of them involved when the other is doing stuff. And Shamath and I are involved. That's a hard job.

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

unfamiliar so the mclaughlin group was the best sunday morning show and like it was so good like snl with parody mclaughlin it probably had a million people watching it but this guy mclaughlin was like pretty cantankerous and if he didn't like what people would say, he'd be like, wrong. This is the answer. You know, like it became so competitive that you wanted to watch it. Now, what I didn't realize by adopting that would be that Sachs is the ultimate debater and will fight like a dog until he wins any debate. And so I may have pushed Sachs into more of a debate situation where I'm trying to not have it be any debate. And so I may have pushed Saks

into more of a debate situation where I'm trying to not have it be a debate. I'm trying to have it be a conversation. So what I've been working on is trying to keep it be a conversation. And then some people in the audience are like, you have to be the fact checker for Saks. And I'm like, no, that's not my role.

I'm not real time fact checking Saks. And so that is a delicate balance of like, and then sometimes I'll ask questions, specifically because I know the audience doesn't know what fair market value when they hear an acronym means. So I'm like, explain that. Right. And I'll stop somebody. I mean, you're expanding the TAM to dentists.

Correct. Thank you. So people are like, oh, J. Kyle's an idiot. He doesn't know that term or i say to somebody can you unpack that can you explain that obviously you know that's her myself 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 i'm like 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 when I'm working with Molly and we're chopping up the news, when I'm the shooter there, right, and she's maybe playing point guard a little bit and I'm shooting and then sometimes I'll pass it to her and she shoots. Like I can travel between those roles and, you know, in that role, I'm acting on behalf of the audience and I get the sense like he's going, Chamath's going too fast they don't know what the spread trade is let me pause can you explain one more time or let me reflect back to you is this what a spread trade is and he's like almost this and that's what i

think has brought in to your point a lot of the dentist crowd and having an intimate sense of where your audience's edges are is a really important role there. Like when we have guests on, I'm always trying to catch where did they just go slightly too deep and I need to pull them up so that we... And you know, podcasting is about going deep. So it is really an art.

Like do you want to stop somebody when they're going down this like crazy rabbit hole? There's no clock in this room. Well, they're going down some rabbit hole that has never existed in media before. Right. And you want to let them go, but you need to make sure they're taking the stairs. Because if they just jump in, you're like,

oh God, no one has any context. They can't learn anything new because you're not connecting it to something they understand. They just jumped into brain surgery. Yes. Let's just explain to us what's going on here. How are we going to chop up this brain? Right. Yeah. It's a bit of an art, but I have to's it's been a different muscle for me to flex and 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 was very binary like there's two categories of podcasts there's uh candy and there's vegetables and like i listen to the audio version of stratechery and that's my vegetables and it's not like deeply it's enjoyable intellectually but it's not like fun and um i i can't i certainly can't be doing anything else with the language center in my brain while i'm listening to that i have to be like on a run and like sometimes even at home so i can take some notes or look something up i can be cleaning. It's a pause type podcast. You have pauses sometimes.

Sometimes you hit and rewind. Let me make sure I get what he's saying here. Or I can listen to the talk show with John Gruber. And it's just like, if I missed out on 20 minutes, because I was like brushing my teeth. And then I left the room and I came back and I'm like, oh, I didn't actually miss anything. Because this has just been like, 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 try to do with this week in startups and all in is try to have it be both.

A little bit of personality, a little bit of entertainment, some fun hot takes. Yeah, I what do you wait related but separate topic um silicon valley yeah i feel like especially there's a lot of part of the in the origins of all and there's a lot of like bashing on san francisco politics and california like there's a lot of crap wrong here yeah but you guys are all still here how are you guys feeling about that yeah how do you how do you feel about about that yeah how do you how do you feel about that like what what do you think of the bay area um you know i lived in new york

brooklyn and manhattan and then i lived in la and then i lived here and so i think my i'm moving to places i enjoy less and less each time like i enjoyed brooklyn and manhattan much more than la i enjoyed la much more than San Francisco. So I don't know where to go next, but I'm going to go somewhere. So why are you still here then? There's no reason for you to be here. I came up here because I had a lot of friends up here. And I had done LA.

And I was like, I wonder how far. I had been a Sequoia Scout. And then I was like, my friends are telling me I can start a venture fund. You kind of need to be up there. I wonder how I would do if I was up there in the industry. And I was kind of this- Because if you wouldn't, you'd always wonder. Well, Michael Morris used to call me the mouth from the South,

because they had like two investments in LA. Oh, the mouth from the South. Sir Michael saying that. But I moved up here. And yes, I love it up here. It's quite bucolic. My kids are loving it. It's quite nice. I would love to live in another city in my life or two. I could see myself in Austin or Miami. I like both of those cities. I think Austin's kind of the future.

I think California is going to be damaged for a decade or two. So I think for the rest of our adult lives, this town. Because of the pandemic? damaged for a decade or two. So I think for the rest of our adult lives, this pandemic or I think the politics and not appreciating the politics, the regulation and not appreciating the tech industry is really the problem. And then you look at this guy. All right, listeners, our next sponsor is a new friend of the show.

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backed by a 24-7 team of experts who monitor, investigate, and respond to threats with unmatched precision, head on over to huntress.com slash acquired or click the link in the show notes. Our huge thanks to Huntress. And Preston, like he is dunking on the founder of Away and Stuart Butterfield from Slack. They're a couple. And he's like, we got a million two out of them when they sold their homes. And I'm like, and you also lost two incredible founders who've created billions of, tens

of billions of dollars of wealth for San Francisco. You idiot. And like, at the same time, Francis Suarez in Miami is listing all of the venture capital and doing a tweet storm about all the companies that raise venture capital. So you have one guy, Dean Preston, dunking on people saying, we have this 1%. So when they sold their $30 million house, we were able to extract a million, too. That's why tech doesn't like me. And I was like, hey, dummy.

Yeah, now all the future earnings are gone. Now, California marginal tax rate is 13.3%. I mean, but just as they have an exit tax now for homes in San Francisco. So if your home costs over $10 million, when you sell it, I mean, I think it's just a sales tax. $1.2 million from them selling their home versus 13% of their future earning stream. Literally, the chef at Slack paid $1.2 billion in taxes from their RSUs. Where do you think you got this? Probably. The million two chef probably paid in taxes on their RSUs at Slack.

You absolute moron. Like you're literally so upset about their mansion and dunking and you're dunking on an individual's name. But anyway, the fact that we hate entrepreneurs who create jobs and wealth, or certain people do, is just insane. It's just insane. Like, what? I mean, you could go change the tax code. It's fine. Like, you know, raise the minimum wage, like Bernie Sanders and Elizabeth Warren attacking Bezos endlessly. And then Amazon starts paying 22 an hour, gives you benefits and pays for your college. And it's like, okay, hold on a second. I know what Bezos just did. He took the platform that

you could never actually enact. And he enacted it inside of Amazon. If it's not perfectly clear what just happened, literally, he's dunking on you. You wanted free college and couldn't get it done. He gave it to Amazon employees. You wanted a $15 minimum wage, he made iting on you you wanted free college and couldn't get it done he gave it to amazon employees you wanted a 15 minimum wage he made it 22 and you wanted everybody to have universal health care and he gave universal health care like that is literally what bezos did to them how embarrassing maybe you could argue that like them pushing him pushed it but no no yeah definitely it is literally him showing like, as the Amazon crew showing like, let the free markets work.

Like the DoorDash, Uber, Amazon, Starbucks, absolute race and battle to just hire entry-level employees and make it delightful for them is what has driven, and a lack of immigration is what has driven, and a lack of immigration, is what has driven these salaries up, right? And the benefits up. It's extraordinary

what's happened with the free market. Minimum wage is still $7. Federal minimum wage is $7 and change still, right? And $15 here in the city. In New York, it's $15. Yeah, it's weird. Alright, listeners, it is time to tell you about one of our favorite things now that Jason is out of the room temporarily.

For all of us who have been paying attention in this crazy space, there are now a ton of options for picking a corporate card and expense management software. So how do you cut through the noise? What's the difference between all of these companies? Well, any founder or CFO who's expanding globally and is becoming really like an enterprise grade company will tell you most are really not up to the job. Reimbursements take forever, issuing cards internationally, huge, huge pain, and they basically never offer currency visibility. Totally. Well, this is why, so Brex was one of the first corporate cards as most folks

know. The first like new innovative. First new innovative startup, corporate card for startups. That's how they started. But now they've added on a whole spend management platform on top of the corporate card. And it makes so much sense for it to all be together. Like the data being integrated lets them do really great stuff to like want your employees to be compliant, so it ensures 100% compliance, but also you need it to be easy for them. So you can do cool stuff like have managers set budgets, and then as long as people are spending within those budgets, then they're just in policy. Everything's always approved all the time. No receipt chasing. No receipt chasing.

No approvals. It's all just done it's all integrated and they really are thinking about this the way enterprise companies who are expanding globally and deal with lots of contractors in lots of countries with lots of currencies and just need like a command center that they're not going to outgrow that is really when you need brex yeah like, like how many companies these days, even startups employ people globally who are, you know, not just need to be paid, but then are like spending,

buying things, going to dinners, et cetera, around the world. Like you need something that operates globally. So it's awesome. The remote work thing is here to stay. They shared the stat with us. More than half of the startups in the last YC batch are from outside the US. And then there was another one. Accenture said that workforce models with productivity anywhere are now used by 63% of growth companies. So remote is not going away. So you really do need to figure this out for people who live everywhere.

Despite you and I and Jason being together here in person today. We are remote. So many of you are, we know, too, obviously. The last thing that we want to tell you about with Brex today is related to being remote in different time zones. Brex now has 24-7 enterprise class, enterprise grade support, which is important because if something goes really wrong with your spend in a time zone, half the world away when everybody in HQ is asleep, you really want somebody to be on that. So Brex now 24-7 is able to take care of everything. Yep. If you have global enterprise ambitions, Brex is the answer. And of course,

they have a great mobile app. They were like one of the first corporate card programs to have a delightful mobile app. And now that they're serving large growing customers around the world, they can do everything from that mobile app too. Indeed, indeed. If you want to learn more about Brex cards and spend management management and why both of those together are now loved by teams all over the world, go visit brex.com slash acquired or click the link in the show notes. Thanks, Brex.

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

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

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

Not fun to me. Not fun at all. And I'm sure you never viewed that as fun, but at least before you were like, I'm willing to put up with it because maybe it's a thing that creates value enough for me to do it. Doing my podcast every day. Absolute joy. Entertaining an audience. 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 the end um did you do it in person or did he no just you know popped on zoom he you know he just started because he did that tweet about his compensation tool yeah where you know here's your total comps. You can move the slider. I was like, that's brilliant. Come on the show.

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

And I do. And so I just committed to doing it every day. And I love it. Isn't it weird when there's something that takes a ton of work but somehow doesn't drain you? Not at all. To me, it's like going to the gym it's like working out or having dinner it's just something i do every day that gives me great joy and then that's i recruited molly i was like i need somebody to do this with me every day oh yeah

who i respect and who's awesome and bring something to the table that i don't have and having she's so great having someone to play off of sure 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. Well, you know, I'd have guests on. It was largely a guest-driven show. And then I would do the news roundtable once a week. Because it was once a week, then twice a week, then three times a week. And then I was like, well, however many I just sell out, I'll do it five, six days a week, whatever.

And I enjoy meeting with founders when they fit a certain profile. But it's very hard to meet with a large number of founders given how many are coming in and it's hard to work with them when they're just talkers. Yeah. To me, that's a very hard part of the job because it becomes very repetitive. So how have you excised that?

Well, I created a platform, Founder University, where if you want to build something, I will talk myself to 200 people. You can build. And then whatever arises, as the performance and the product, you know, and as people move from talkers to the walkers to from, you know, when they actually start building stuff, that's when I get great joy. And so I'm like, bring me the people who have product velocity so i told my team listen you're doing my team does six people don't understand the scale of the business i have nobody's yeah i don't really understands what i'm doing and i kind of like it that way but the angel syndicate is now the largest syndicate in the world i've deployed like 185 million dollars in my career as an angel

investor doing 50 million a year now. That's awesome. I'm raising the fourth fund in public. Like 11,000 angels in the syndicate. This is going at a really significant velocity. If you were to look at the slope, it's not quite a hockey stick, but it's hockey stick-esque in terms of the total capital I've deployed. And it's in really high-quality companies I'm getting better at. There's 11.

I have 22 people and 10 on the media side and 12 on the investment side and of the investment team like people don't understand like oh you're a solo gp I'm like yeah with 12 people um those people are doing 60 introductory meetings per week six zero and then we're doing maybe 15 20 second meetings so there's it'll be 100 meetings a week shortly probably across 10 people or 12 people. But you're not doing the... I'm not doing them. Yeah. And what happens is...

You had this line, was it on, it was on Twist, I think. Not for me. That's a lot of work. People say that's a lot of work but you're like, yeah, but not for me.

That is the new philosophy. This is why my energy is really high. This is your unlock. I have told everybody who comes to work for me, I work 60, 70 hours a week. Keep up.

If you can't keep up, don't be here. I'm looking for a fixed 50, a solid 60 hours a week. You don't have to match me 60 or 70 hours a week, but keep up. And are you looking in that team, are you looking for the next Jason Calacanis to be a part of that team? Or is it someone who likes doing that part like that's well let me ask it more directly is it someone who's content with doing this or are you looking for people that are like hungry enough to be the next jason i'm open to all of it yeah i'm open to all of it i don't they don't need to want to have my you know absurd um unhealthy 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. So yeah, they probably would. Not for very long. Yeah, mine might be like three years. You'd come, you'd learn, you'd extract. Which I'm fine with, too.

People come and they work for two, three, four years and they go start their own venture fund or whatever. I'm also fine with it. It's great. But what I told them was, you know, let's just find the great companies. And I looked at investment team meetings, usually they're Monday. People do it for an hour or two, and then they go to lunch.

I said, I want to do it twice a week, Tuesday and Thursdays, 2 to 4 p.m. Hit me with companies. So that was another innovation I did. And I also brought Mike Savino, who was my first boss when I was in my 20s doing IT, and I brought him on as president. So this is like one of my lifelong best friends. And I said, run the company. Here's what I want to do.

The podcast, meet with founders, do the LP fundraising. That's it. Teach the course. Are you enjoying the LP fundraising? I am now, yeah. I am kind of like, remember in X,

I don't know if you watch Billions. Oh yeah, every episode every episode great so you know like at some point um uh he was like i'm gonna go raise money yeah it's cap raise time it's cap raise time and like wags is like so i got my wags mike savino's my wags yeah and i got my wax who just fixes everything and i'm like i'm gonna go raise money and so literally was like we're doing 506c and they're like, don't do that. You're now, you were in kind of this one bucket with your capital. And now you're going simultaneously in two directions of you want the public and you want the big institutions, right?

We'll see. I've had select institutions make small bets. The first fund was 10. The next fund was 11. And then the last fund was 44 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 Hsieh, rest in peace. David Sachs, Chamath. Just a bunch of my friends put money in. And it was to see if I wanted to be a venture capitalist and do this as a career. And I was like, yeah, capitalist and do this as a career. And I was like, yeah, I just did it over five years. And the second one, I raised 11. It took me six months to a year to raise the first.

It took me, the second one took three to six months. The, no, it took six months. The third one took me three months to six months. And in this one, I think I'll wind up raising in the first 10 days what I raised in the first, yeah, a couple of funds. Wow. I literally did two webinars. A couple hundred people came to each show. For people who are listening, 506C is you can raise in public, which means you just can tell people I'm raising a fund.

And I was like, well, I'm doing all in. It doesn't make any money. I have this week in startups. And I watched a bunch of these young, inspiring VCs raise publicly. Right. You didn't raise publicly. No. You did it private. I thought about it, but for a whole bunch of reasons.

Well, it's kind of scary because people don't do it. But if you have no track record and you want to raise, so like this guy, Mac, the VC. Yeah. You did a great episode with yeah it was great i had him on uh i had like you know first time founders for a season of angel um it's like a subsection of the this week in service podcast and i became an lp in his fund and he just told me like i just did like hundreds of meetings i did like five meetings a day for a year and i raised my whatever 10 million dollars and uh he's african-american and he's like it's just a matter of how hard do you want to work and i'm like well careful saying that publicly because there's a group of people who do not want you saying that he's like no it's just all you have

to do is like you go to angelish you set it up and then you just start talking to other vcs you talk to me you just you just have to be willing to take 50 meetings a week and i'm like dude do not say that it's easy to raise a venture fund as a black man in Silicon Valley. But that's the position. It's not that it's easy, but that it's possible. On the internet, too, you find your people who believe that with you. And then they believe in you. And then they back you. Correct.

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

I'll put that right there in the place where I keep everyone who tells me. Yeah, three years from now, what to do. Yeah. And so I mentioned it on All In. I tweeted it. And all of a sudden, I had 1,000 people sign up. Is there a limit to the number of LPs you can have? Of course, yeah.

It's 250 accredited, up to 10 million, and then 2,000 QPs. And so it's a lot more work. And QPs. Not for me. Not for you. But not for me. To catch everyone up. Qualified purchasers.

Look at you playing Jason. I know you know what a QP is. I just wanted to dish the ball. I think it's 5 million in investable assets. And then accredited now is 200 if you're an individual for the last two years. Each of the last two years. And 300 if you're a couple, each of the last two years in income, or a million dollars. In net worth.

In net worth, outside of your primary residence. So there's a whole, and these things are going to change over time, but I believe that we're going to have a test for accreditation, and you'll be able to be sophisticated if you take a course. So I think that's coming in the coming years. So just like I democratized angel investing was the book angel was the first syndicate on angel list the most successful syndicate on angel list created my own got the domain name the syndicate created the largest one have done 265 syndicate deals by far like the largest amount of anybody i think

i don't know i mean now as a participant of the fund on angel list like these are like those are big numbers like you do something've done... You do something consistently. Four SPPs on AngelList and we have the fund, too, but, like, you know, yeah, like, that's a lot. You're herding cats. You need to have a lot of people. But anyway, putting all that together, I think now is the time to democratize venture capital.

So that's what I'm attempting to do here, is I want more people who are accredited and qualified purchasers who've never been in a venture fund to look at the asset class and just consider it. It's high risk. It's high reward. I'm in 20 venture funds myself, including yours. Thank you.

But don't pitch, Jason. I'm sure I will do yours. No, I mean, I'm just going to pick them based on people I know or people I know online or on the pod. And, you know, I'll do one or two new ones a year. Well, this is kind of to the conversation earlier. Like on the internet, this is the democratizing thing.

Nobody's going to just give you, if you just, you know, nobody's going to just invest in your fund. But if you go do stuff. Yes. And then people are like, oh, Jason does stuff. Great.

I'm going to back Jason. Ben does stuff. Be of action. Yeah. And it doesn't mean you have to start a podcast. You could be a blog. You could do events. Whatever. You could create Founder create founder university whatever it is you can do any of those

things uh you could have a track where you can be an advisor to startups whatever it is do you like the idea i'm curious as someone that's always raised from sort of individuals do you do you like the idea of having some institution be like can we invest 15 million dollars oh yeah of course i mean i've had five you know million dollar checks 10 million dollar checks in the fund from institute from you know fund to funds and institutions you know but i would very much at some point i don't need it but it would be meaningful for me uh both my parents are cancer survivors to have memorial sloan kettering's endowment or an endowment or something like that somebody like that you know if they wanted i would work you work really hard to try to get them a great return.

I would find even more meaning in what I do. And I got that from Sequoia. They would have this Sequoia dinner every year for the founders and they would say, here are what the foundations who are LPs are doing with the money you made for them with your companies. Click, click. Here's what Ford Foundation's doing. Here's what this foundation's doing.

Their conference rooms are named after their LPs. And the conferences are famously named after them. And this is real. Powerful. I find we have state pension funds and stuff like that. That'll make you get- In PSL Ventures. You take it much more seriously.

Of course. Because it's not just about the reward. It's not like, oh, I'm so excited about what we're going to do for them. It's like, this is really important to preserve and not grow, but like preserve this capital. Yeah. Yeah. Which the psychology of doing that while you're taking big swings with asymmetric upside, that's that I find to be a

fascinating dance that was like one of the seasons of that of billions was he's like i'm gonna be a family office no i'm gonna raise my own phone right and so there's this natural tension for acts like which should it be and he decided yeah i like when i have other people's money because he he seemed to perceive like i think he felt that he wasn't a somebody in his ecosystem in his community without managing outside i think it's like playing you know in the bubble with nobody in the stands versus right getting on the court at madison square it's like and there's people in the stands your returns your numbers don't mean anything unless you're putting them up for dude i'm doing this public where i should say

quasi-public people still have to sign up to you know come to a webinar um but i'm sharing with them like here's my the totality of my investments and here's what i've done and here's what i plan on doing with my team um so you know i'm kind of enjoying it um and if you know i've met with all the top endowments in the world over the years and they're very kind to me but it's always been like solo gp is a blocker no track record your fund is so small we're a 50 billion dollar endowment yeah and you know like you know um at some point like one of the ones who's the most rigorous i wouldn't say exactly which one was like we have a lot of respect for you we know who you are people would like you to sign a lot of respect for you. We know who you are.

People would like you to sign a book and take a selfie with you when you're here. But I just want to be straight with you. We don't add many funds. And if you go through our process, it's going to take a lot of your time. And it's going to result in you not getting our money this time. I don't want to put you through that.

But I respect you. And if you want to do it, we'll do it. But maybe just put one more fund on the board and let's talk on the next one. And I was like, let's do that. I don't need the money.

Let's wait. And I think what a lot of these funds are doing now- Was that in the last fund cycle? That was in the third fund cycle. Yeah, so now- So I will contact them. What I decided to do was let's see what my syndicate members and the public want to do let's see which qps come out of the

woodwork 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 i added two more so i'm going to do five webinars this fall and then i'm going to go on the road and start meeting with folks. Are there any downsides to doing the raising in public thing other than... Not that I can see. I mean, I guess you could fail in public to fail to raise the fund. That doesn't seem like something you're scared of. No. I could also, you know, the freeing thing, you know, is I looked at the model and I said, you know what I could do? I could just invest my own money in each company

and then syndicate them and never have another LP. Right. But then you're raising capital every single time you're making an investment. Yeah. And I'm getting deal by deal carry. And I have 100% of my investment, not 25% carry on it. And I don't ever have to talk to anybody i could just

say i'm placing this bet would anybody like to join me 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 so literally this you know it's so funny hearing you say this myself lots of our other friends in the ecosystem that are in similar positions they're having this same question. Like on the one hand, I could do what you just said and do very little work, but, but have it all be pure on the other. Yeah.

I could go do what you are actually doing and like raise, have LPs be accountable. Yeah. How did you weigh these two? Um, I, I'm going into my second era, my second decade of,

uh, investing. And I, again, last two years, a lot of like sort of post-pandemic and tony's death thinking huh like what's possible here because i've won so much in my life i didn'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 pod i'm like guys i don't aspire to be a billionaire it's not important to me if it was i would do a late stage fund i aspire to be happy and do what i love doing every day which which is the podcast, maybe get in 40 days of skiing, hang out with my kids, take them on the mountain, and then meet with like,

you know, early founders and be able to say, I helped that company at the earliest stages. That to me is the rush. I found them first. I backed them first. I sat there with them and figured it out with them. We were talking about the legendary twist episode 180 with you and Travis. Yes. Like,

I mean, that's the secret before the show stuff, David. Yeah, that is. But, but from the juicy before the show. I can talk about Travis.

Yeah. Yeah. But that was like, you know, you know, Urbu was such a baby company back then. And like, you know,

one city, one city. I invested and I had an open angel for him where Siam Bannister and Chris Fralick from First Run, you know, invested in the company. I think they both met them there. Sokka was there too, but he already, he had a relationship with Travis, so I can't take any credit for that. And Kevin Systrom was watching and I was going to kick him out because he was at this co-working

space called Dog Patch. I worked there too. Yeah. I worked at Co-Tweet. Yeah. So he was, oh, Co-Tweet yeah so he was oh co-tweet i know that yeah so he's sitting over there building bourbon yes and that's right sock is like can bourbon come in i'm like fuck no this is like private shit and he's like but and i'm like just

tell him to sit at his desk and i won't wait this open angel form was at dog patch labs here on the pier no way i think that three year then they shut down because it was going to collapse condemned yeah condemned um so that was there and uh nival also did a bunch of like events there for angel i at the time nival and i were very friendly um not not friendly now but not we don't hang out or we but we used to hang um kind of 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 and he's like i'm gonna do this thing angel list i'm like well i'm just in person thing

and he's like great let's just you know trade notes or whatever and then he sent me the syndicate thing he's like do you know about spvs i was like i don't explain it to me he taught me what spvs were he introduced me to assure fund, which I wound up investing in. Did you buy that? I didn't buy it. I mean, I bought 5% of the company. I invested in it. But they back everybody. And they've done more SPVs.

I don't know if they're up to 10,000, 5,000. I mean, they've done a ton of it. Seriously great group over there. And so he taught me how to do syndicates. And the first one I did was calm at four or five that's nuts it's funny i was i was looking like literally like winning a championship the first time you step on the court i was looking at your track record getting ready for this and i was telling david like i think the word that i used because like obviously uber is some ridiculous

multiple on a return 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 look at Calm. I looked at David, and I was like, he sharpshooted that one. That one I could be even more proud of because I'll tell you why. It was ridiculously early and a super low basis. It was $4 million. We put $370,000 in on 6%,

and they didn't raise any money until it was a $250 million valuation, so no dilution. Sharpshooter. Sharpshooter. It's like Vanto. Vanto is the same story. I could even cry like telling the story

but Alex too and I became very good friends and Michael Acton you know afterwards because he wasn't actively running comm while Alex was. Alex at some conference I was interviewing him

and doing a little victory lap for him and giving him his flowers. And he said, I just want to stop and tell you, you don't actually know this story, but we were going to shut the company down. And Mike and I had a conversation. What? Do we take your money? But we're not sure about this.

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

And they found product market fit while burning your money. Yes, I think so. I think so. Because you're like, take more of my money. No, no. But if you think about that as like a,

that is not the case with Uber or Robinhood. I was along for the ride. Let's be honest. I did not change the trajectory of the company. But for Jason Calacanis, Calm was not. Well, he said they were going to shut it down, possibly. I don't believe that they would, but I do think it was on the table.

That's like real angel investing. That's real. There's a of like individuals participating in venture rounds and like yeah no offense oh hey i don't take any offense so like call that angel investing but like coming in when the company could die needs 100k 200k 300k to get it to the stage where they revenue to date i think when i invested I invested. Like, ever. Yeah, because they were selling the app for $10. Because remember, at the early stages,

there was no subscription model. Right, in the App Store. You just sold an app for $10. That's right. So the business model of apps was make a lighter

for $1, then make lighter 2, and charge $3, and then lighter 4 would come out. And you'd be like, well, this doesn't make any sense. Making Microsoft Word

1.0, you buy it, you throw it away but we can just update it. 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'd buy Angry Birds 2 Angry Birds 3. It was a really weird time and then they were like they told me because it's under NDA

as well, hey, subscriptions are coming. That's going to change everything. And they were going to do $10 a year. And I said to Alex and Michael, how much does it cost to go to a meditation class? It's donation-based, and there's only 10 places you can go. I'm like, well, what's a suggested donation? They said $20. I said, you want to church $10 a year.

It's $20 a month. How often do you have to do this to get value? $20 a visit. Yeah, $20 a visit.20 a month how often do you have to do this to get value $20 a visit I said how often do you have to do this to get value it should be a daily practice how often do you have to go and learn I said if you go weekly that's good so it's $80 a month

to go and we're charging $10 a year so that's like $1,000 a year versus $10 what if it was $10 a month we've been thinking about that i was like okay and they're like okay yeah i think we're gonna do that and it was then they went to ten dollars a month or whatever they didn't wind up at sixty dollars a year whatever it was but we got money printing machine pretty quickly so i've never made an investment at like pre-product market fit that's like now worth over you know

a billion dollars like that's a that's a very early to very successful and i'm curious like did it feel any different when you were making that investment were you like there's something more special here of course than my normal investment absolutely really absolutely and that's what i've basically turned into a playbook at launch and that i'm teaching these 12 people how to do is how to do that. What do you think it was? Like what was, when you look back and you're like Nine factors. Nine factors. Okay, alright.

Angel.University No, I'm not even teaching Angel.University I'm training my team when they're meeting with those 60 companies and every time they pitch me one, they say this has three of the nine, this has four of the nine and then I'm creating the anti-list, these are the things that kill companies so how many of the 15 things, we have a long list of things that kill companies, has three of the nine. This has four of the nine. And then I'm creating the anti-list. These are the things that kill companies. So how many of the 15 things,

we have a long list of things that kill companies. How many of the red flags does it have? Reasons to not invest. How many reasons to invest does it have? And, you know, like one of them for me, and everybody's got their different thoughts, so I won't give all of them, but one of them is world-class design.

And so I'm trying to teach people what world-class design is. And world-class design to me is, if you were to look at all the companies in the space, this one would have the best design. Or this would be one of the top 10%. So if you were to look at something like Calm or Robinhood, okay,

they're the best-looking app with the best UX of anybody in the category. So Calm was better than Headspace. Robinhood was better than E-Trade. I mean, it 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 and they'd say world class design and i'm like i'm like like i really like the design i'm like pull it up and they pull it up and i'm like that's a template from yeah you know like a website builder and it's a stock photo

but where's the actual design of the product and they're like oh that's on this product page and we probably was like okay yeah again that's just like the i mean if this was a bank's website maybe but that's not world class that's serviceable design that's utilitarian design that's okay design that's good design it's not world class so let's if we're going to say world class like a worldclass performance is different than a service performance. World-class cinematography, world-class script, world-class dialogue, that's different. And then product velocity is the other one I like. Okay, we met with this company in June. It's now July.

What's changed about the product? And they're like, we don't know. I'm like, okay, well, let's find out. Where's their change log? Where's their roadmap? So in the earliest stages you might have revenue traction or user traction but you might be able to ask them for their product roadmap and somebody like travis would be like yeah here get on the phone with this guy and we'll

walk you through it here's what we're debating about on sunday we're reprioritizing a month later they play and then they're like check check check and then you go like if we're with ro with super human and i was investor in his company before that report, of Raul, like the changelog at Superhuman. Dude, Superhuman. People don't realize, like... They're like, bink, bink, new feature, bink, new feature. Oh, boom, we fixed Grammarly. Oh, bink, we have Calendar.

Boop, oh, we got a new Calendar feature. Boop, we got this feature. And you're like, hmm. So here's an interesting question. We should ask Raul this. We've had him on the show three times now. Product genius. Like, the parallels between superhuman

and figma are uncanny like design led founder like revolutionary design in the software rewriting the entire browser stack in order to get the performance and i remember it being breakthrough when it came out and then the only thing that i can recall being different between then and now is adding a calendar thing that i don't use and a mobile app and ipad support and and why outlook support you just don't you know when you hit command k yeah you probably know 50 of the features right like do you use remind me of this i do okay great do you use labels do you do snippets i do okay yeah which it was all there when i started using it for three four years ago i think a lot of those things have gotten better and better yeah so it's just that

like polish polish polish polish um i really like want them to make snippets multiplayer i want to share my snippets oh yeah oh with your team i love yeah so i want all of david's past emails they're so nice i don't do email anymore. You do it on the phone? No, no, I just don't do email. David just doesn't respond to emails. I don't email anybody. When you pass on a company,

what do you say? I've been literally creating a collection of how to pass with my team, and I'm standardizing that. I'm trying to... I don't know that I'll be successful, and this may be a mistake, but I'm trying to just not have...

I don't end up having a conversation with a company if I'm not going to invest. No, but you must say, hey, we are not going to invest. You've took a pitch. Oh, no, I get it. I don't— How do you say no? I don't— You basically don't take a pitch unless you're going to invest. It's the weirdest thing.

Oh, that's very weird. So you do all your work up front? You front load it, the deck, everything? We're weird so you do all your work up front you front load it the deck everything we're in this unique position as you are too but um with acquired we're like you know we have every six months we have six companies that we work with on the show as our sponsors and our partners and we get to know them really well and treasury and i'm now an investor in just about all of those companies so so it's not like uh and it's... And I'm now an investor in just about all of those companies. Okay, fair enough. Got it. So it's not like they're pitching me. It's growth stage investing.

Yes, it's growth stage investing. They're clearly the winner. Yeah. They're not yet priced as if they're the winner most of the time. Yeah, exactly. But they're going to just keep compounding. Yeah, good luck. Yeah.

Pricing's going to be hard. Well, it's a pretty good... We'll see. We'll see. It's a pretty good entry price. We'll see. Yeah, I don't know what's going to happen to these companies after... You know, the flat is the new up, but I think, you know, 50% haircut is the new flat.

Well, public comps got hit 50 plus percent. Yeah, I mean, this week they got hit harder again. Yeah, I mean, I'm buying equities right now. I've been doing it at JTrading.com, and I am going to buy more. Sorry about all my picks a couple weeks ago. Which one? Whatever I told you. Oh, yeah, yeah, no, no. I actually love Taiwan S no i actually love taiwan semiconductor uh and stitch fix was the other one no i did not

say twilio twilio was yours and i love that one too and i i like shopify as a pick um i'm actually really enjoying it it's really not investing out not investment advice but it's balancing out my um understanding of what public success is compared to private. And so for me, it's just a way, like, am I going to fight with a blaster? No, I'm a Jedi. I use a lightsaber. But I'll learn to use a blaster. But if you look at the very best.

It's not as elegant. 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, they all trade public stocks. And they do it for this same reason. They're going to fight with the saber, but they want to know how to also use a blaster. Or how to fight in an X-Wing or something.

It's not what a Jedi does, but Jedi will do it. It also keeps you really sensitive to the public cycles. 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. And early stage investing, it's almost silly to compare. My opinion is it's very silly to compare to public comps because the only thing you know for sure is we're going to be at a different place in the cycle by the time this company gets liquid. So it's ridiculous

but it's helpful to drive into you like how much variability there is when was the last time it was this different that's yeah i'm really enjoying understanding what the founders of those companies go through versus the founders of the private companies that go through what the boards decisions the board has to make of a public company versus the board of a private company yeah so it you know i'd like to join a public board at some point it's probably not a good idea for me to have said that because i might get an invite for one and that might be too much work but um yeah but hey especially given the market right now i'm very careful but you could you could also invite me to do that but it's just it's been especially through the show now you

have relationships with public company founders sure of course yeah i mean if i really wanted to i'm sure i could lobby oh you don't have to be on the board though you can have a great relationship doing the analysis and i'm doing it anyway with molly every day okay you know twilio's or adobe's come i just bought adobe this week when they bought fig so funny so did i not investment advice not investment advice but i was like they bought figment tanked okay so here's my theory on this they bought figma and tanked and i was like why did why do people hate this and they're like oh no adobe's admitting defeat and that like they can't innovate a house or and to me i look at it like adobe has customer channel and it was foretold five plus years ago that they were not going to build

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

YouTube approach. I think everybody in M&A knows now. Yeah. WhatsApp. WhatsApp. Just leave it alone. Don't screw it up. So I like your analysis. I added to that analysis is, if you're not going to win the war, and you can build an alliance and then fight another war, they've just removed the downside of Figma creating Photoshop. I'd be concerned for Adobe if 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.

You just discounted the right move. Fantastic. People are like, oh, you know, the Warriors signed Kevin Durant. And you know what? We're going to lower the cost. But they paid a lot to get him on the team. Yeah. And oh, you know, the Warriors signed Kevin Durant. And you know what? We're going to lower the cost. But they paid a lot to get him on the team. Yeah, and oh, you know what?

We're going to lower the cost of the tickets. It's like, okay, I'll buy courtside seats. Or they're lowering the odds in Vegas. It's like, wait, why are you lowering the odds? Their odds increased. I'll place that bet. So it's just an obvious bet. And then all that's left is Canva.

And Melanie's awesome. Totally different thing. But but yeah and they have a free canva already and you know what if there's always a the internal people who are penciling out that spreadsheet yep there's a group of mbas who penciled out that spreadsheet with figma no offense to mbas who are listening and they said hey boss if x y if x listening. And they said, hey, boss, if X, Y, if X, Y, Z, and they said, here's like five potential paths. If we make Figma free for 10 users and whatever, or if we take whatever Figma costs and then we blend it with the Adobe suite, okay, we would get this many more Figma users. But we know when we get Figma users,

then we get non-designers to pay for it. So right now, Adobe has a bunch of designers paying for it. Right, right, right. But they may not have all the non-designers in there. Only designers pay Adobe. Right. Well, no, they have Marketing Cloud, but that's a totally different set of...

Yeah, only... But when you look at Figma, like, i got a figma account like people who are doing giving feedback on designs the business side the sales side can get into figma so i think they got the whole creator class exactly so i think you're opening up the aperture of who design software is for with figma it's for bd it's for the ceo sure the cfo can come in and take a look at the product. Oh, legal should come in and take a look at the product.

Yeah, buy them a seat. So it's like Slack is for the dev team. And it's like, yeah, and the sales team. And ops. And anybody else might as well be on there because that's where everybody is. So that's what I think is going to happen with Figma.

It's like everybody's going to 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 the cost of doing business. Any company that has like that kind of strong network effects inside an organization deserves a meaningful revenue multiple because they just, their differentiator is literally the company's moat.

So like I tweeted this, but like if I have a castle and it has a moat around it that is much wider or deeper than your identical castle shouldn't you pay more for my castle it's more defendable 100 like the virality of i think sax made this point on all in two weeks ago which was like if they're paying 50x now and the company's growing okay they're paying 20x next year 25x who cares right it's such a high growth company and then i was just thinking well somebody's got a theory there and when i sold web weblogs to AOL, people were like, oh my God, these people are idiots. They gave $30 million for Weblogs Inc.

They've only got 200K in revenue. What they didn't realize was AOL autos, AOL tech, AOL lifestyle, those were sold out at like a $90 RPM, revenue per 1,000 pages. Yes. The ads were different CPMs. So then they would put an Engadget or an Autoblog story or Blogging Baby or whatever other blog we had on the homepage of AOL.

And a half million people would flow through. And then they would put those ads on our sites. And then they would blow out $50,000 or $100,000 in ads a day on a blog. And those people were like, great, because it was costing AOL to make content like $500 per piece of content, $3,000 per piece of content on AOL.com slash autos, whatever. And we were doing it for, at the time, $5 a blog post because we said, well, people can write for an hour. So it's $20 an hour and it's $6 minimum wage. It made sense 50 years ago.

The internet media game has changed so much. And then I was like, okay. You guys were doing 200K annual revenue? We had done 200K to date over the 18 months.

What a day. I mean, now like the world we're in today. People looked at the multiple and they were like, J Cowards is robbed. And I was like, okay, no. $30 million sale? I but now i look like what do you think like here's a i look like an idiot five years later and that's the best the best m&a yeah

is when yeah you look like you robbed the bank yeah and then five years later it looks like you robbed the founder youtube instagram figma will be in this category like yeah when they bought instagram they're like 30 people worked at this company and they gave them a billion dollars. You guys are morons. And now it's a $150 billion company. 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 $10 million in... When I was at the Code Conference, a lot of people have been trying to buy it or put it as part of their network obviously. Which would kill it. Yeah, my partners

are right, let's not make money from it. Part of the delightfulness of it is that we're not trying to monetize it. But you do get huge economic value out of it. Shmuck pulled me aside at some point and was like, hey Shmuck, we're friends. Your next fund will be bigger.

I was like, when you have a friend who can be like hey dumbass yeah like that's a good friend so i appreciate you not saying that and he's right and it's playing out um and we had a rule no um no talking our books on the pod but we kind of talked about it we're like the pod is great when we talk about our bets so explaining our bets not talking our book is the new philosophy so like you guys just started doing that about his stack you know um i still call yeah he did he just uh found a target for it yeah chamath talked about um the uh health care the health care company which is i mean we wanted to talk about that because chamath and i both agree like maybe we're i mean maybe like we're definitely overprescribing

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

So I'm kind of bummed that Freeberg's a little bit of a blocker for it, but I might turn them around and we'll have a vote maybe in the fall. Doing another one? Well, I'm going to do another one. The question is, am I doing it under the All In brand or do I have to create a new brand for it? And so I told the guys, I said, I'm going to do it again.

Well, Code Conference is done. So like there's a vacuum. Code Conference is done. Yeah. They need a new host. That's crazy that that can be done. Like it's such a valuable. No, value no i talked to bank off about it and he's been very public you know kara swisher i think is going to do the pivot stuff and wants

to do other stuff and you know she's i really respect what kara has done you know 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 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 a Rolling Stone. And when he went electric, they booed him. I was like, really?

You're booing Bob Dylan because he's using an electric guitar? Are you guys dumb? Did you hear all along the Watchtower? This is incredible. And so I think Kara Swisher is moving on but Jim said he's going to keep doing it and it's probably

a small list of people who could actually host that credibly. A very small list. Which you're definitely on. I am? You think? How could you not be on?

Maybe I can make that work. I'm not even saying that to make you feel like... No. I'm joking. I'm being a little bit facetious here. Okay, okay.

You're joking about being humble. I'm trying to joke about being humble But 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 mean, whatever the issue is, like we've had our issues. We all have issues. But I think there's basically two possibilities

for all in Summit. I'm going to present it to the boys and say like, here's the plan. Yes or no. And we agree, we'll put it to a vote. So we put it to the boys and say like here's the plan yes or no and we agree we'll put it to a vote so we put it to a vote if three of us want to do it we'll do it and if two of us want to do it then we can't

and if I already, Freebrook already said if you do it on your own with a different name I'll come and support you and I'll show up to do a talk or do an interview or whatever and I was like great so I'll do it with a different name if they don't want to do it, and the fans can decide if they want to come or not. Partially in. Partially in, exactly. So it's up to the boys if they want to do it, but it was a pretty great success.

You already have call-ins. Well, yeah, and I started doing a a call in show called After All In for the last two episodes where I took calls about the last episode of All In just to support David because I don't think

people remember how great that app is and it's really made great progress so I want to be supportive of him and I have a small investment in it

and I'm not very meaningful but on the one hand this is ridiculous on the other hand it might be ridiculously low it's worth 50 million to answer your question 50 to 100 million i mean as a top as a top 40 podcast it's worth at least

50 million on its own though but i mean like economic value that the four of you oh who knows over the lifetime like if chamath or sax 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 10 you know like so yeah that's the thing like i think like man weblogs like you were doing 200k of revenue you sold it for 30 million pretty great takeaway yeah and now look at this like you know yeah i mean listen i hope it keeps going i hope we can keep it on track and um you know i i love doing pods this week in startups is a juggernaut as well you know yeah that one's out for 10 years and all in is what is that like a quarter million listeners

or something yeah some of that range yeah i mean it's hundreds of thousands per episode and yeah it's very niche podcast you know i'm not trying to make it all in um i'm trying to make it for founders and so you know if in order to make it bigger it'd have to be it for founders. And so, you know, if in order to make it bigger, it'd have to be worse for founders. Right. And that's what we talk about. I want founders and capital allocators to listen to it. We want to thank our longtime friend of the show, Vanta, the leading trust management platform. Vanta, of course, automates your security reviews and compliance efforts. So frameworks like SOC 2, ISO 27001, GDPR, and HIPAA compliance and monitoring.

Vanta takes care of these otherwise incredibly time and resource draining efforts for your organization and makes them fast and simple. Yep, Vanta is the perfect example of the quote that we talk about all the time here on Acquired. Jeff Bezos, his idea that a company should only focus on what actually makes your beer taste better, i.e. spend your time and resources only on what's actually going to move the needle for your product and your customers and outsource everything else that doesn't. Every company needs

compliance and trust with their vendors and customers. It plays a major role in enabling revenue because customers and partners demand it, but yet it adds zero flavor to your actual product. Vanta takes care of all of it for you. No more spreadsheets, no fragmented tools, no manual reviews to cobble together your security and compliance requirements. It is one single software pane of glass that connects to all of your services via APIs and eliminates countless hours of work for your organization. There are now AI capabilities to make this even more powerful, and they even integrate

with over 300 external tools. Plus, they let customers build private integrations with their internal systems. And perhaps most importantly, your security reviews are now real-time instead of static, so you can monitor and share with your customers is ready to automate compliance and streamline security reviews like Vanta's 7,000 customers around the globe and go back to making your beer taste better, head on over to vanta.com slash acquired and just tell them that Ben and David sent you. And thanks to friend of the show, Christina, Vanta's CEO, all acquired listeners get $1,000 of free credit. Vanta.com slash acquired. I'm not trying to move up the rankings. I don't mind, you know, hanging with, you know,

all in being number one in tech and then hanging out with you guys at, you know, slumming it at six to 15 with you guys in the rankings. It's like, that's where we belong. Look, I got number one on lock. Four to six, but who's counting? Whatever, you know,

that's where we belong with these things, right? Like it's a niche podcast by definition, right? Like it's not supposed's a niche podcast by definition right like it's not supposed to appeal to everybody and you try if you want to appeal to everybody like read the bible like that's right if you go to this is the beauty of this guy who reads bible passages and he and huge it's like if you can literally true crime true crime religion read the bible or ben shapiro dunking on libs. The end. That's how you get it. Or do it daily. But Joe Rogan's out.

He's on Spotify. Right, right. He's not in the other rankings. Or do a daily news program for 20 minutes. But that's not what I want to do. I want to talk for an hour or three about deep topics in Founders and Capital Outfitters. You know what would be a fun acquired episode is Howard Stern. I feel like it's underappreciated how much Howardard stern i copied my that's the playbook that should be the next taylor swift yeah type episode that we do yeah no for sure he wrote the playbook

i literally took notes for it king of all media do you know him i have never met him i'd love to at some point i have a lot of respect for him i mean obviously he did crazy stuff when he was young and that shock jock stuff but he in his later years became a great interview great interview great interview where he really refined his technique i really appreciate that about him and he created characters sound familiar yep 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 u.s open sores where and then he would do howard stern's like new year's eve celebration so yes he did the equivalent of those in new york but it was a very new york thing so he like he played tennis against baba booey and but i mean he got 10 000

people to show up and buy tickets right to a tennis match that they pumped up you know like for whatever number of months i remember this from my childhood and then he did his books uh which were phenomenal he did a movie he did a movie he did tv shows so he's done a lot of stuff and i i'm just starting uh the process of doing a reality show right now so i'm literally gonna do are you really yeah i mean just you or the besties or just me um besties don't want to do it they don't have time for it i mean there was there was talk of like maybe all in you know kind of going on to one of those services. Like people had reached out like, hey, would this work? That's a lot more work, though.

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

And the Weinstein Corporation. Oh, wow. Yeah. And it didn't make it on air, but I have the- You should be a Shark tank judge i had been they had reached out before mark bernard had reached out early on when it was dragons den um right before when they were going to bring it here so when it was dragons down they had reached out early but i wasn't very successful back then um i wish but you know i think now i think i would

have the credibility and the advice to give that i could do a gordon ramsay style show that would be very entertaining and educational and be completely different than you know the fundraising aspect and the pitch aspect of shark tank so i'm not going to do that but i'm you know i've got you know the i won't say which one but a very major the major you know uh reality tv folks reached out i think in part because all that was doing so well would founders and companies feel comfortable like i feel like a really amazing window and insight would be the type of conversations that you have with a founder

as they're building the company yeah so they would founders and companies be open to that yeah so the nbc show i had done the pilot for which never made it on air um uh what was really good was really about you know me incubating companies and uh they spent like four or five hundred thousand dollars doing the pilot it was really good and it would have been a big hit did did it get canceled because of the hard wow so they were just like anything that was in his company and all the ip is dead because he's a monster and so anything associated with it but you got to remember he did project runway so he had done some of these giant shows people don't know that about that and so that's right i forgot yeah that had the twc at the beginning exactly so you know i just nbc you

know i nbc bought the show in the room loved it and did the pilot and it came close and chamath was on that episode actually he did the pilot oh my god he was like my vc friend who came in and it was my vc friend it's no it's hilarious um but i'm excited to do it if it works out it works out if it doesn't you know no skin off my back but i like the media space and then you know i this is the thing i'm choosing to do media because I get joy out of it. I'm 51 now. I'll be gone soon. Like, I want to enjoy. You will not be gone soon. Well, you know, you never know.

And, you know, I've had two friends. Well, you've been to your friends, yeah. I have two friends who died young. And I'm just like, I, you know, I talked to my wife. I was like, I don't know. Like, what if I make it another year or make it 25 years? But I want to make it count. I'm not going for max dollars.

Like, and so when the guys break my chops about that, I'm like, guys, it's not my priority. Literally, maximizing money is like... Well, also, you're probably at a point now where... It's literally not in the top 10. What is more money going to do? It seems unlikely. You're literally trying to get a plan.

It's not about my life. You don't want to play. You guys understand my life. It is ridiculous and charmed. I can do whatever I want. I have enough money to do whatever I want. My kids are fine. I can have whatever I want. I don't care like a third home like it's i have a ski house i have my regular house

it's good i'm i'm good my kids have their college paid for i'm good like 100 i literally do not care about do you feel like that's a demon that you fight is like no any allure toward no i had it when i was younger i wanted to be powerful. I wanted to be important. I wanted to have money. I wanted to be seen. I wanted people to recognize my greatness like any person recognized me for what I do. I got all that. It literally does not even come up my radar.

To have more money is the last thing I'm thinking about. I do want to be the greatest investor of all time. To me, that's meaningful. I know I'm Mount Rushmore for angels. Yeah. I want to be Mount Rushmore for all time. Yeah. Like to me, that's meaningful or be one of the, I want to be like, I know I'm Mount Rushmore for angels. Yeah. I want to be Mount Rushmore for all investors. So when you guys do your thing in 10,

20 years, and it's like, okay, you know, here's Doug Leone and Moritz. And you know, uh, here's,

you know, early John door. Here's girly. Like if we are making them out Rushmore, you want to be on that with them. I would like to make it there or at least be in the conversations. All right, listeners,

we kicked Jason out of the room again because we have our next sponsor of the episode, our very good longtime friends over at tiny Berkshire Hathaway of the internet. If you'll recall indeed indeed so they're so much so the berkshire hathaway of the internet that as we told you about a few seasons ago they literally built a business on the internet selling bus of warren and charlie that you can order berkshire nerds.store that's not what we're here to talk to you about today though they've got something new to share with us this season that we've been talking a little

bit about uh kind of from the founder angle, but we want to share with you from the VC angle. Yeah. So the core business of Tiny is acquiring wonderful internet businesses. These are businesses doing 5 million or more in revenue at 30 to 40% operating margins. Well, and the DNA really comes from Andrew and his partners originally running MetaLab. And of course, it was a very successful, it is a very successful design agency that started spitting off cash. What do you do with the extra cash? Well, they know how to run a great internet business with MetaLab. And so they started buying more and more and more businesses. And so now with this awesome portfolio, Dribbble, Pixel Union, Creative Market, 8020, Girlboss, these are all tiny

companies and... So what are they doing differently now? It's funny. It's different in a sense, but it really is the same tiny playbook that they've always been running to buy wonderful internet businesses. But something changed in the last five years. We were in this crazy go-go era where lots of businesses, even ones that really aren't the shape of what venture capital should be funding, well, most

venture capitalists were funding those businesses too. And so you end up in this situation where you've got a lot of companies that have raised a lot of money that probably aren't tripling, quadrupling year over year the way you would sort of expect a venture business to be doing to raise their next round of capital, especially in this environment. And so if the business is growing, you know, 20, 30, 40 percent, and it can get profitable or it is profitable, well, most of the time... That doesn't really make sense in the context of a venture portfolio.

Right. But the founders probably want to keep running that business. They probably want to keep serving those customers, doing their life's work. Exactly. And you end up with a lot of these companies in a portfolio that are capable of being tiny-like businesses, but are not going to provide a big exit that's going to move the needle for the venture portfolio. Well, Tiny realized they can provide the perfect solution to this problem for the VCs on the boards of these companies, for the founders running these companies, and most importantly, for Tiny to then come in, partner with these founders, and own these companies in perpetuity

without looking for an exit. So really, what Tiny can kind of do is come in, buy the company from the VCs, or a lot of the company from the VCs or a lot of the company from the VCs, get them some or all the money back, get their time back, get off the board. So they have capacity to do new deals. So it's great for founders to keep doing their life's work. They can figure out a structure with tiny where tiny is very good at figuring out structures that make sense to align interests. It's really super cool. Honestly, I've talked with a bunch of folks of varying different financial groups and institutions over the years who have had some version of this idea, and it's never gotten off the ground.

And I'm so glad that Tiny is now doing it. And they are the perfect ones to do it. And this is the perfect time to do it. So very excited for this to exist. Yes. Well, if you are running a business like that, or you are invested in a business like that, or your friend is invested in a business like that, you really should shoot a note to hi at tiny.com and just tell them that Ben and David sent you. Don't tell them Jason sent you. He's not here right now. You can say Jason sent them too.

All right. Our thanks to Tiny. When you guys are having the conversation in 20 years and I'm gone or I'm retired and you're saying Mount Rushmore. I can imagine you retiring. Yeah, I think it's possible. I met Don Valentine when they were like, you know, he was not active investing. But when I pitched Mahalo, he was in the room. He came up.

I talked to him. Oh, he was still hanging out there all the time. He was still hanging out. That's awesome. Yeah. Yeah. Like, why retire? He was just awesome.

Oh. But, you know, if you had that conversation right now about Mount Rushmore, like, you gotta, okay, so. Who's on your Mount Rushmore? Well, I mean, you gotta have Don Valentine. Yeah. Right. That's just not possible.

And how are you scoping it? Because you probably need Paul Graham, too. Well, yeah. I mean, you got Paul Graham is in the running for sure, but that's like not possible but how are you scoping it because you probably need paul graham too well yeah i mean you got paul graham is in the running for sure but that's like a number of startups but there's a lot of big ones in there you have big impact so paul graham's definitely running but okay so do you go with john doors in there along with so if you're doing firms it's a lot easier because you get kosla door and um perkins tom perkins you get theostler, Doerr, and Perkins, Tom Perkins. You get the three of them at once. You do Sequoia. Which people forget.

Vanu Kostler spent a decade at Kleiner Perkins with John Doerr. Yeah. And you had, yeah. So, I mean, you look at that firm, it's like, that's like the OKC with like James Harden, you know, whatever. But then you have Doug, Leone uh Mike Moritz and Valentine Ruloff yeah but you put all of them there active all at the same time for those 30 years and it's like well that's Mount Rushmore right so if it's a Mount Rushmore of Mount Rushmores

is kind of how you might look at it you know you definitely have to have we just did benchmark you gotta have the fab four era of the fab four era of benchmark was truly something special yeah so i mean it's kind of like it kind of builds itself the mount rushmore right now right it's it's going to be sequoia kleiner benchmark and then we're like we're going to have a big debate on the fourth arm right yeah like is it well it just depends how wide we're willing to scope it is it like traditional series a type venture firms or is it angelus naval right that's had a huge impact you put yc in there do you put yc or techstars both have a huge impact do you put um you know uh who else could be in there that's just you can argue for founders fun you can't say yc and techstars it's a completely

different thing on the way like what yc is like. YC is like three orders of magnitude more significant. For sure. They've done the same number of companies, I think, but just in terms of returns, yes. But Techstars, I think, was a little before Y Combinator. But anyway, you definitely have Y Combinators running for that fourth spot, I guess. And then who else would you put in there? Masa? Or Uri Melner?

That's high beta. Well, no. I mean, but maybe Founders Fund. Impact on the industry? Impact on the industry. No Founders Fund yet. Excel, I don i don't know depending on excel would be in the running for sure it's ron comway i think the way you kind of 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 three successful generational transitions where each of the generations would have been on mount rushmore all right so then let's just do this. Instead of Mount Rushmore, because we're talking firms.

So for firms, you do Mount Rushmore, right? So I think if you were just going to say the Hall of Fame. Yeah. Oh, yeah. Just the Hall of Fame. Yeah. And the Hall of Fame has, let's just say. Oh, dude, we should open the Venture Capital Hall of Fame.

Venture Capital Hall of Fame. The Venture Capital Hall of Fame. Capital Allocator Hall of Fame. Top 25. I was trying to figure out when we were doing the benchmark episode research, which will be out by the time this comes out. 2480 Sandhill Road is a

very special building. It was the Forethought PowerPoint Quadris Complex office. Then it was Microsoft Silicon Valley. This is the internet! This is the internet! It's like, wow. We've the only three people who want to be shit about this. Oh, no. The three of us are so excited right now. This is the internet. It's like, wow.

We've aggregated all the other people who care about this. Everybody else who cares about this is listening right now. It's like, and like Sebastian who wrote The Parallels.

Yeah, yeah, yeah. You guys are taking this way too seriously. It's not that important. But then we're like alone yelling in David's house about a fictional Hall of Fame. TVI,

TVI, Meryl Pickard, TVI, that's a good, August Capital, Benchmark Pickard, August Capital, Benchmark Capital, Shasta Capital, all in this same building. And I think there's some space for rent

in there. I don't want to go live down there, but I think we've got to take out a lease just to put the museum, the Hall of Fame. A Venture Capital Hall of Fame is something we can collaborate on. We should just do it. That would be pretty fun. Fuck it. We'll just do it. 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 into the

There should totally be a Hall of Fame. We should totally do this. Kim's in Ohio exists. It's fucking hilarious. You know, Cooperstown. There is a, what do you call it? It'd be our Cooperstown. Yeah.

There is the Computer History Museum, but it's for the PC, which is totally valid. Right, right, right. But it's not for capital allocators. It's not for people. Like, totally valid right it's not for capital allocators it's not for people like yeah there should be a hall of fame and do we like do we midas list style ask people for the real hard truth no no no it's about impact you know we decide the three of us we decide it has to be impact on the game does the nbca have like a lifetime achievement award is that the closest thing it doesn't really exist anymore yeah no it no. It's about impact, legacy, like the intent of the person.

Right. This is why like Paul Graham would be like, you know, first ballot. This is why. Yeah. Okay, who are the first ballot entrants? I mean, it's so obvious. We've already talked about it. We've already talked about it.

Those are all first ballot. Do we have anybody who we haven't talked about or who's not obvious but would be a first ballot? You can't. This is what I'd say. If you're under 20 years, you're not. Like like let's wait till you're 25 years in yeah just like the sports hall of fames you gotta have a yeah you gotta be you're not playing in the league anymore so paul graham's still playing in the league does jeff bezos count like wow i mean how many investments has he made that google investment is crazy so there's that but there's also like

i think amazon is the best venture firm of all time. Just in terms of, like, it's internal. They're not separate companies. So, yes, capital allocating, lowercase c, lowercase a. They've been great at placing bets. But you're right. Jeff Bezos is probably the most successful angel of all time. Yeah, I mean, if you just did it on dollar. And LP.

Yeah, and LP. Put it on, you know, when you're looking at it, I think you've got to look at impact. Like, impact on the game, legacy. So is Carmelo Anthony Hall of Fame? Of course he is, but he didn't win a ring. But he's Carmelo Anthony, right? Or Charles Barkley. He didn't win a ring.

Okay, so then we've got like Arthur Rock. You've got to look at like the founding father type. Of course, of course. Yeah, there's no doubt. I mean, that's like going back to Bob Cousy or whatever. Going back to like some really like people who built the league kind of situation before it became the league. So you've got the league and you have the people before the league. You have people in the league.

You've got generational shit right here. Patrick Ewing. Because I think you look at Gurley like he's part of that Patrick Ewing generation. That Hakeem Olajuwon, Charles Barkley generation. You start talking about Founders Fund or YC or AngelList. Now you're talking about more modern era. Still going. Modern era.

After 2000. But if you started before 2000, it's a different group. Do you notice we haven't talked about Andreessen Horowitz in this conversation? Oh, God. Who cares? No. Impact on the game? They're in.

They're in. Both of them are in. For sure. No doubt. First ballot. They totally are. I guess. Impact on the game?

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

Well, I do think they have interesting ambitions, though. I think this, like... That's the problem. It's more ambition than soulful but there should be a jp morgan or a goldman sachs of silicon valley and they're big for sure i don't know yeah why is it why does goldman sachs manage the money of entrepreneurs i just feel it's too okay fine but i just feel like it's it's too it's it's like too premeditated and less soulful i i feel like it's a soulful business where your intentionality and your relationship with the founders really matters. It's not the craft.

I mean, it's the literal antithesis of it. It's the industrialization. Yes, it's the industrialization of it. It's the factorization of it. And listen, I'm sure it'll be very successful. At the end of the day, all the returns will be great except for the crypto stuff. Well, I mean, there'll be mean reversion. Because like when you get the law of large numbers, you have mean reversion.

Exactly. It will be mean reversion for sure. I mean, that was, at some point they leaked a lot of their returns and they were like, eh, not fair. That was the 2015 thing. Well, they did actually. It was early. So yeah, that was stupid that the journalists didn't understand it.

But there were some older ones. But it was like during that time, like you start comparing it to Sequoia or Benchmark. I think in the arc, it will not be comparable to Benchmark and Sequoia. And we made a lot of hay of the fact that they made $11 billion in profit on Coinbase. And I do not think they sold out of that. No, they didn't. So they did not make $11 billion in profit as of today. Well, I mean, timing is everything.

We'll see. It's interesting, too. I mean, having just done this Benchmark episode, like the Benchmark Fund 7, one of, if not the best institutional-sized fund of all time. Just, like, unreal. 20 to 25x.

But even that, like, the fluctuation in the marks on that fund, and it'll probably end up between 15 and 25x, maybe. But it fluctuates up and down so much. Yeah, of course. I mean, we live in a very volatile time right now so yeah i like the hall of fame idea it's kind of interesting i think we actually would be a fun thing we should get some space on sandhill and put up no i just we

could just do it as like a dinner we just literally have we don't need every year we get a yeah we get we could just start in a restaurant but you could get like a little hall yeah and say we're going to induct into the ventureure Capital Hall of Fame the following people. And here they are. And we just have three pictures. Boom, boom, boom. And you just drop it.

And it's like, here's our three people. And then people come up and say something about the person. And I think we could do the three who we would hope would be there. And then we'll have one or two posters. We do it like the sports where you have the person who's being inducted chooses who inducts them sure which oh that's fun uh yeah

so ruloff does doug yeah whoever does maritz yeah yeah but john parker does maritz mike chooses who you know he has jason calacanis come up and be like. No, no, he just had Larry and Sergey come up, obviously. Yeah, totally. John Doerr would ask Bezos. I mean, it's a killer. It's a killer idea. I mean, we just do Bezos, Doug and Mike. Yep. And then.

Who inducts Bill? You do one in memoriam. Yes. You would do one in memoriam. Yes, exactly. You do, you know, whatever. Yes. Because it would be anticlimactic if the only person, because we will induct Don first. And if the only person that we inducted that year wasn't a living person who could attend

maybe it's four people a year you know you have to think how do you you want to get to 25 so maybe it's you want to get to 25 to 50 over 10 20 years so yeah maybe it's three a year in order for this to like feel good i think you're right that it has to be about impact not about returns no returns is like so that would be like saying it's like albums sold for the rock and roll full of fame right there are people that'd be a very andreessen horowitz way to do it as well yeah entries but oh what's the total assets under management you know and it's like okay dude we get it yeah nickelback sold a lot of albums yeah they're the nickelback eventually no i didn't mean that you said it i wasn't talking about it oh god oh god oh god now they've sold tons of albums right i'm not saying that they're a million no but there's like oh boy there's you know if you

were to look at ron conway does ron con did ron conway who had a bigger impact ron conway or andreessen like i think it's a conversation you know and if you because Ron Conway when I came into the industry like there was at one point I was at a the Crunchies and Ron Conway at one point

like somebody said like hey can everybody stand up who said Ron Conway invest in their company and a hundred people stood up and my mind was like oh whoa

angel investing's cool I mean I wasn't an angel investor at the time I was you know long before i became a scout but that i always remember that moment when like a hundred people inspired partially inspired is that what gave you the is that what like put you in business as an angel the scourge is what put me in business yeah what happened was i had was your uber investment you personally or was that sequoias that was sequoias okay yeah and we were like rulaf 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 the stealthy but i mean travis knew but you know it was it was a pretty great deal you know it was like um you know at the time they carried 50 50 at the time yeah they dropped it down after that i bet like every time i'd see doug leone he's like 50 and they had 30% carry at Sequoia at that point, I think. Whereas you, I mean, if I were you, I'd be like, 50% carry to them. I can't believe it. No, no, no. Doug would always, they're so classy, Doug would always make a joke, he'd say, 50% carry.

Oh, God, we get 30, you get 50. This is funny. We get 30. We get a lot of it. Pretty funny. Pretty funny. You know, listen, we're very lucky, I think, if you look at what we do as capital allocators, We get 30. We get a lot of it. Pretty funny. We're very lucky.

I think if you look at what we do as capital allocators, I think it's a very special part of the – it's a very special function in the world. I take it very seriously, as you do, for the retirees you're investing on behalf of. But also, I was just thinking about humanity, and I don't mean to make it heady, but these companies do move the human species forward. Like an Elon. Yeah, exactly. So the human species getting moved forward by, as Steve Jobs would say in those commercials, like, this is the crazy ones. They do need fuel. They maybe don't have an idea of if they should even build this company.

And I think the capital allocators really come in and say, here's some fuel. Here, go fight that war. It's fuel and it's belief, too. I mean, your story about Calm is not uncommon, I think, amongst founders. I mean, the stories about Don Valentine and Atari and other places where he was at Cisco,

he's like, listen, we've got to get this thing back on the rails. This thing's going to zero. There's a lot of existential moments where things go to zero and like so can i ask you as we start to like wind down drift toward the end of the episode here that's your line that's your favorite line drift that's that's the ben signature is this a good time together like is this different enough from our normal show should we do this what should we change yeah do you like this i think a casual glass of wine and just you know uh if you have friends of the pod and you want to go deep and talk about them in a more casual way sure yeah

i mean i think it's a great way to just have somebody on again you know so if your profile somebody like i forgot that i had you had done like the first episode with me and uh that was more about my career and more details and so i'm starting to tell stories over again it's like well let's talk about some other stuff right yeah so i think it's a different our audience was i like this i like this well part of what we you know like lex has done so great with his show yeah but but those type of conversations but i feel like that's more what's the right word our shows are about the business of tech yeah no his is intellectual i don't know why he's in the tech vertical but i like the format and like kevin rose used to do the foundation series

and like yeah i mean long-form interviews like howard i mean i think joe rogan stole it from howard yeah and i think it's now lex stole it from jo. Yeah. And I think it's now Lex stole it from Joe. Yeah. I don't want to say stole. I think, you know, inspired by. Yeah. So Lex is clearly inspired by Joe. And Joe was in the running to replace Jackie Martling on the Howard Stern show.

People don't know this. So he was very enamored with Stern. And he wanted to be Stern, I think. And he eventually has supplanted Stern in a way. He did become Stern. Yeah, he did become Stern. And so good on him. Yeah.

Right down to the, you know, Sirius, Spotify, like right down to it. He became Stern. Well, yeah, doing a platform deal. Yeah, doing a platform deal. Which is what Stern did. Stern had multiple platform deals. He did syndication first. Then he did the Sirius XM one because it was a new platform

and he built the platform. He used his number one show to build their platform, right? Which is, I think, what, yeah. Which is, but actually to bring it all the way to Full Circle, back to Charlie Rose. Like, he was like a, you know, I mean, he did more than business, but like he would have. He did culture, business, anybody in New York, because New York, everybody in New York was pretty fucking interesting.

Yeah. Yeah. You know, he could have somebody from Wall Street, a publisher, an author, somebody who does films. He would have Spike Lee on it. He'd have Woody Allen on. He would have any actress on who was doing something interesting, any novelist, Margaret Atwood, anybody, which is coming through New York on a press tour. 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. It was like a little sort of more jazzy, you know, a little bit more acoustic. So I like this format for you guys. Do you listen to Smart List at all? Do you know about that show? I have listened to one or two episodes. It's Bateman, Will, Arnett, and then somebody else.

Yeah, the guy from Will and Grace Sean I don't know who that person is but they bring on a surprise guest each time and the other people don't know yes so they're not prepared yes

and it's like it's like Katie Perry it's like Chris Pratt yeah it's become a big deal I kind of want to do that of tech but like wait you and I don't know who the

one of us is bringing somebody no that's not your racket you guys are not good you can't make you got to know the person's background much better but there's a celebrity to carry a certain charisma with them that our industry doesn't have yeah but maybe it doesn't have to be a surprise as much as like well that the other thing is that it's even though they have guests the show is actually about them the guest is a prop in a way yeah i guess i've only listened to one or two you know i see it in the rankings like it does incredibly well like it's a top 10

or top 25 podcast is it part of a network is it part of spotify or something i don't think so because i see it on itunes i don't think so it's really weird that like spotify doesn't allow joe rogan and call her daddy on itunes because the advertising would be huge right so why not like the ads in and put them over there's some nba that's run the numbers that says it's more valuable if it's driving new subscribers to spotify i guess that's it i guess that's it yeah oh guess you know what they want to be able to have those new subscribers so when they go renegotiate with the yeah music i saw they're doing audiobooks too now that's the next piece yeah that is the next piece yeah they're doing audiobooks one-off purchases smart i mean audio is great all right it's getting

really hot in here it's getting so hot for those of you who don't know we're in like a sauna a new yeah david's new house david just moved david's got a new empty house we there's no air conditioning here it's sort of like The Shining. There's no furniture. We just furnished this room. We literally, this is all from Craigslist. All of it. Literally, in the last two days.

That explains the smell. That, all right. You could have, I mean, listen, you're rich, dude. Just go on and buy some Crane Barrel. We can't all be Jason Calacanis. No, come on, man. I know those fees. Oh, my God.

Craigslist, I love Craigslist. I love it. You buy used furniture on Craigslist? All the time. I do not buy new furniture. All right, it's got to stop. I bought a temporary couch on Craigslist. It's the thrill of the...

No, no, no. You're going to get robbed. Don't do it. It's too crazy. Craig Newmark, I love you, but... All right, with that, our thank you to Vanta. Oh, Vanta.com slash... Acquired. Oh, there we go, Vanta.com slash acquired.

Vanta.com slash acquired. Our thank you also, you don't know who the other sponsors are because we didn't record them live with you because we felt very strongly that it was, you know, we wanted to make better use of your time. I love reading the ads. Are you kidding me? Do you want to read our Brex ad? They don't sponsor my pod, so no.

Maybe they have. I don't know. There's also a lot of ad living in it. I know a lot of people who use Brex ad? They don't sponsor my pod, so no. Maybe they have. I don't know. There's also a lot of ad- The Brex card. You're talking about Brex card. Brex, yeah. I know a lot of people who use Brex. I think we use Brex. It is.

One of my companies. If you're enterprise, if you're global, by far the best corporate spend management. It's much more than a card now. Yeah, for expenses and everything like that, right? And then they've kind of expanded behind that. So you can give cars to each of your employees and then if they screw up, you can turn it off or something.

Yes, exactly. They go, they jump the fence. Pre-approve some budgets. Yeah, you don't want people jumping the fence and going crazy. All the listeners know

because they heard it like an hour ago. They're very familiar with it. Oh, it's in here, yeah. So anyway, thanks. Shout out Brax. So that's Brax. Shout out Brax.

And then... Use the promo code to us. We share this last sponsor. These are great folks. These are like dear friends and geniuses and raconteurs. Masterworks? No, no, no. Good guess though.

Think smaller but bigger. Literally small. But secretly huge. Tiny. Oh, tiny, of course. Yes, they're buying companies. They're buying companies. They're doing a good job. Yes, they're creating like. Tiny. Yes. They're buying companies. They're buying companies.

They're doing a good job. Yes, they're creating the Berkshire of the internet. There you go. The internet. Can you imagine a better time to get the monkey off your back of venture capital and- Yes. Sell your company. Secure the bag.

Listen to the VC telling you, let's go. That's my favorite J-Cal line, 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. You get that AOL. 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. You get that AOL weblog

exit. They call it. Oh, man. Let me tell you something. I'll tell you the story. What did you do when you secured the bag? I'll tell you what happened. It's a funny story. I'm in my office, and I got Bank of America, and I got low thousands of dollars in my Bank of America, and I got an low thousands of dollars in my Bank of America.

And I got an American Express card with negative 10 on it, and a Visa with negative 5 or 10 on it. And I'm sitting there, and they're like, oh, wires are good. You know, the BD people are AOL. And so I'm like hitting refresh on the thing. This is 2006, 2007? 2006, yeah. I'm hitting refresh.

I'm hitting refresh. And then bink, bink, bink, bink, bink. All the numbers come in for the whole amount. And you own most of Weblogs, eh? Brian and I were equal partners. Then we had Peter Rojas had some ownership. And then Mark Cuban was our big investor. And by big investor, he put 300K in for 5%.

So that was a great outcome for him. Oh, wow. Yeah. Or more. Maybe on 10%. I think on 10%. Anyway, long story short, my wife comes in. She said, you OK?

And I said, what? She said, are you crying? And I reached up, and I had a tear in my eye. You're like, this is a new experience. I've never had this before. And she said, why are you crying? And I said, my family will never have to worry about money again because i spent my whole life worrying about money yeah you know

my dad had lost the business everything was a very cathartic thing for me and i think people you know who are already rich uh you know or maybe who come from means just they don't understand the concept of living with the fear of being broke and in debt all the time. And then when you have the bag, you secure that tiny bag. And it's a tiny bag, but it's filled with diamonds and cash. And you just open it up and say, thank you, Tiny. Thank you, Tiny, for securing the bag. AcquireDiamond.fm slash Tiny. No, it's Tiny.

They don't give us a thing. Oh, they don't? We don't? No, they just want you to know Tiny will help you secure the bag. Is it Hiatt Tiny? And tell them that they would send you one. Whatever it is, just don't give us a thing. Is it the Hyatt Tiny? And tell them Ben David sent you. Just know that Tiny. Tell them that Ben David and Jason sent you. You can mention Jason.

I did buy a one-touch espresso machine. I bought a Jora one-touch espresso machine, which at the time was like two grand. And I was like, this is unbelievable. Then I tried to buy a Ferrari. They wouldn't sell it to me in Beverly Hills. You were the riffraff? What, like no new money or something?

Yeah, basically. I went in there and they're like, oh, yeah. I'd like to buy a Ferrari today at the 430. 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 names from 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 Nance 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. It's part of the strategy. They have the Ferraris, but they don't sell the Ferraris to Bill DeSteve. We're not putting anybody on your list. I was like, well, how long is the wait list? He's like.

Don't even bother getting on it. I was like, OK. I was like, I'm a cash buyer. He's like, everybody's a cash buyer. I'm like, OK. 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, I'm good. You want some Pellegrino? He literally offered me Pellegrino espresso. And I was like, I have the same one touch. Sure. And this Italian guy is like, I was like, I don't mean to be rude, but what do you do here all day? He's like, well, we deliver the cars and we service them and we sell used cars, pre-owned, certified.

For more. And I was like, oh. I was like, well, I would take a pre-owned one. He's like, oh, well, the one you're looking at is pre-owned. I was like, no, no, no. The one I'm looking at, the 430, the red one out there, that's the one I want. That's got a sticker in the window. He's like, yeah, yeah.

We certify them. We put the sticker on the window. I was like, oh. Well, that goes for $230,000 or whatever. And so, yeah, what do you want for it? He's like, $300,000. And I was like, no, no, no. This is a potentially paid one.

I was like, the used one I was looking at. He's like, yeah, you can't get these cars. And I was like, ah. So you pay over $70,000. He's like, but it only has 2,000 miles on it. And I was like, 2,000 miles, it's $70,000 more than new. I was like, why wouldn't I buy a new? He's like, but it only has 2,000 miles on it. And I was like, 2,000 miles, it's 70,000 more than new. I said,

why wouldn't I buy a new? He said, because you can't get them. And I just, I'm such an idiot from Brooklyn who doesn't understand the concept that people would pay over for the car and I'm just perplexed.

That would bother me too. I was like, all right, well let me think about it and I left and then I was with my friend and I was like, and I had the Rob report

and it said like, number one car was the Ferrari F30 and then I turned the page and it was like, and I had the Rob report and it said like, number one car was the Ferrari F30 and then turn the page, it was Corvette C6 was the number two car. And the starting line was, make Ferrari,

buy two for half the price of a Ferrari and beat them off the line or something like that. And I was like, let's go to the, let's go to the Chevy store.

Let's go to the Chevy store. I walk in, there's Corvettes everywhere. The guy looks at me and he goes, you want to buy a corvette i said yeah he said if you buy a corvette today i'll give you five thousand dollars off i was like yeah so we go out on the 405 and we're driving the corvette and he's like this is a corvette son like you're going 70 miles an hour i said i'm not he says i'm not selling this car to you unless you hit that gas much harder. And I said, okay.

And I punch it to 100 miles per hour. The guy's like, yeah, how does that feel? I'm like, great. That guy's good at his job. I come home with a Corvette. I come home with a yellow convertible Corvette. My wife's like, what happened to the Ferrari? I was like, this thing only costs 65 grand.

It's like 70 and I got five grand off. And it's American, baby. And it's like 70 and i got five grand and it's american baby and it's american and uh that was the car that i famously uh was according to gawker robert scoble myself and elon when elon got the first p1 of the roadster right he was like i got it i was like oh let's meet in brentwood and we were driving them at a you were racing we were driving them along sunset boulevard a spirited drive a spirited drive along sunset boulevard and we did it like five times and five out of five times the tesla just destroyed the corvette and i was like i'm doing something wrong and you know then

we switch cars and we and i was like nope electric just gonna beat everything and this was the first one that you know first yeah that was the prototype that's, you know, first. Yeah. It's amazing. The prototype. That's in space right now. It's the Cherry Red one that's in space. Oh, that's the one that's in space. And there's a famous photo of me and Elon in front of the Corvette. With the spaceman.

That one's it. But there's a famous photo of the two of us, you know, in front of my Corvette and his P1. And I remember that night like it was yesterday. Wow. Just before the iPhone, you realize. Like, Robert Scobo was recording this on his Nokia smartphone. Dude, these are the memories, right? Crazy.

This is the journey that you've been on. Yeah, it's pretty crazy. And this is the stuff you just will cherish forever. My life is unbelievable. I am so grateful for it. And thanks for having me on the podcast. Listeners, thank you so much. Acquire.fm slash Slack.

Come join us. We'd love your feedback. Oh, Slack's cool. I got to pop over there. This is a new shtick. Yeah. Acquire.fm slash Slack. Come join us. We'd love your feedback. Slack's cool. I'm going to pop over there. This is a new shtick. Acquire.fm slash store. You can buy cool shirts. Swag.

Slash jobs. Find your next great career experience. Acquire.fm slash Craigslist. You can get a couch. You can get a couch. That's right. Acquire.fm slash David buys you some smelly furniture. My God, it is hot in here.

All right. We got to go. Let's go eat some food. Let's have some sushi or Mexican. I don't know what we're going for here. That was awesome. Oh, so fun. thank you so much of course all right listeners we hope you enjoyed that uh very first acquired sessions with jason calacanis it's a new format we're playing with we would love your thoughts acquired fm at gmail.com or tweeted us at acquired

fm i am curious what you liked what you didn't like and uh on that note of feedback we have something that we really really want you to participate in no pressure or anything but it would mean the world to us if you did we just launched the 2022 acquired survey and we have had the wonderful problem of our audience growing a lot since the last time we did one of these. And we no longer feel like we have a great handle on who all of you are. And so we would be eternally grateful if you would spare the three minutes to participate. Tell us a little bit about yourself. One lucky winner will get second generation AirPods Pro, which I have been wearing all over the place and are indeed twice as noise-canceling,

whatever that means, Apple, and has some, I think, better battery life too. And David, for you, they have very tiny little ear tips, right? Yes, for my tiny, tiny ears. I'm so excited about the extra small tips. They finally fit in my ears. It's awesome. 10 other winners will get Acquired t-shirts from our fancy new merch store. Again, three minutes to participate at acquired.fm slash survey, or you can click the link in the show notes. And thank you so much for helping us. It really does help us run the show here at Acquired World HQ. All right. Well, with that, our huge thank you to our sponsors for this episode. We've got Vanta, Brex, and our friends over at Tiny. Links for each of those are in the show notes. And with that, listeners, we'll see you

next time. We'll see you next time. Thank you.