ACQ Sessions: Jason Calacanis
02:30:03 Share

So you wrote a magazine? Magazine, yeah. That's how I started, yeah.

- You say more. - 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. - Welcome to Applied Sessions. - All that stuff that you said beforehand that like is really juicy, I don't think we should put that in. - No, definitely not. Definitely not. We don't want to tell people where the bodies are buried. - Well, cheers boys. - Cheers. - Here we go. Is this the first one or? - This is the first in real life. - Wow, IRL. - But I think this is our ninth, 10th together, something like that. - A lot between the two pods, yeah, for sure.

Great to know you, boys. So this is the first Acquired Sessions. Acquired Sessions. I feel like I should get out a guitar here and just play some Dylan.

This is your baby. What is Acquired Sessions? Acquired Sessions is normally on the show, we are like so scripted. Yeah, you are. And we have a great time. We do four hour episodes. You know, it's awesome. But really for folks like you who we know really well, what happens if we throw out the script? And just chop it up. And we just chop it up. David Rosenthal unplugged. Wow, I love it. I love it. This is literally MTV unplugged. Literally. Literally.

Okay, listeners, now is a great time to thank one of our big partners here at Acquired, ServiceNow. Yes, ServiceNow is the AI platform for business transformation, helping automate processes, improve service delivery, and increase efficiency. 85% of the Fortune 500 runs on them, and they have quickly joined the Microsofts and the NVIDIAS as one of the most important enterprise technology vendors in the world.

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Well, we have no agenda, obviously. No agenda. Wait. Where do you want to start? We've got to thank 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, SOC 2, HIPAA, GDPR, and more. And we've got CEO and co-founder Christina Cassioppo 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. Actually, a bit of 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

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 to suck too. 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.

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 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 talking about that stuff. Yeah, yeah, yeah. Is Mahalo why you started, you went from print to print to... Well, in the 90s, you know, I grew up in Brooklyn. My dad...

had his bar seized by the feds because he didn't pay his taxes during the 1987 crash. He became like, he got behind and the feds showed up one day and this was the maybe six weeks before I was set to go to college. And he said, "Hey son, I can't help you with college. Good luck. And I might be going to jail, so take care of your mom." So he was like really behind on his taxes and you know, state liquor authority, they kind of take it serious.

So feds come, shotguns, the whole thing. They seize the place. They seize everything 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 and Were you set to go to college somewhere else? Well, that's another story, but I was set to go to Brooklyn College. I got into that I had also taken the police exam to be a police officer So my brother went into the force and then I said, you know what? I'm gonna see if I can go to college and make that work So I'm gonna Brooklyn College. So I decided to work during the day and then I went to school four nights a week 6:00 to 9:00 p.m Carried full credits 16 credits a semester and

and I would work fixing laser printers all day. I was a bad student. I was always that student who underperformed. I didn't find great meaning in academics, but I had a computer when I was in high school, and I was more interested in playing with my 300-baud modem, which then became a 1200-baud modem on my PC Junior. So it kind of, you know, like many people of that era, we were sort of set on a path because we were the first generation to have a computer at home.

I actually had an Atari 2600 and it could play Tank was the game that came with it and Pong. And so my dad bought this for us when I was six or seven years old, 1976, 1977. And he had one of the first Pongs in Brooklyn in his bar. He must have cleaned up on that. Oh my God, it was crazy. And so I just got exposure to video games and computers. And I was like, wow, this is incredible. Computers are going to change everything. And then I happened to hack some software. We used to...

I ran a lot of scams. You told us about the VHS. So VHS, Jason's Hot Tapes was technically my first business, but there was a side job I had, which was cracking software. So we were

We would make copies of like Chessmaster and stuff like that and then sell them for $10. And then we started like hacking and doing what was called phone freakings. When you were doing this stuff, like you had to be reasonably technical to do it. Not like the, you know, not like Wozniak technical, but like you could. We soldered chips sometimes. We changed. Yeah. 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 Bleecker Street. I used to hang out in the West Village or the East Village. It was like the cool places to hang out. And...

Like a thing to do would be to go to Tower Records and look at the zine section. So there was a concept of a zine, which was short for magazine. But a zine was something you wrote with your friends. You printed it yourself at a photocopy store. It's like blogs before blogs. Blogs before blogs. And I created a zine. I was like, I'm going to be a magazine publisher. So the first one I did was Cyber Surfer, which was about dial-up services and CD-ROMs. And I did it with my friend Brian Alvey, whom you might have heard of in my career. Yeah.

We went to high school together. Weblogs? We did weblogs together. Yeah. But in the early 90s, I did... Engadget, Twad... All that stuff. Everything you sold to AOL. Everything I sold to AOL. But anyway, before that, I did that magazine. And then I met Jerry Colonna at Internet World, the first one.

And there was a booth. That's right. When Jerry was a VC before he was like the whisperer of startup coaches. Before he was a VC, he was consulting for Lycos. And I think CMGI. And so there was a Lycos 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.

So they wanted you to come like 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 a thousand bucks. 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. The Flatiron became USV, right? Yeah. Square Ventures. Flatiron went with Jerry Colonna then when Jerry decided he wanted to move to Colorado and just chill. Yeah.

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

you're doing stuff which would you rather do and I was like I think I'll do the magazine

This was before. Now it's like, I do both. And now it's like, I do both. Why choose? But just to back up to GeoCities, that sold to Yahoo for like $3 billion. $5 billion. And Flatiron was the main investor. Yeah, Flatiron maybe owned 5% or 10% of it at the time. It was like a huge win for them. I mean, Fred was on fire for a New York VC and Jerry. They did pretty well. How did that happen, right? I mean, Silicon Valley was here, but they were in New York. What was going on? There was a lot of good companies brewing in New York. And my concept with Silicon Valley Reporter was, well,

Well, they have Red Herring and Upside in the Bay, but I own New York, and I had Silicon Island Reporter. And then I started one called Digital Coast Reporter in LA. So I had two magazines, two conferences, two email newsletters. I was kind of king of New York, right? I grew that business to $10 million in revenue off my credit cards. And had 75 to 100 people working for me when I was 27 years old, and I didn't know anything about...

how to run a magazine, how to run an sales. I taught myself everything. What did your family think of this? It was pretty heady stuff because I wound up being on the cover of the New York Times on Charlie Rose and they wrote a feature story about me for 8,000 words in the New Yorker. So anyway, it's a really cool time in New York because at that time,

You were either in media or finance or art publishing. It was like a finite set and I was in publishing but I was also in this new thing technology and so everybody wanted in on that it would be like the equivalent of crypto is today 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 about a lot of this when we did our like big Jason, Empire of Jason Calacanis episode with you. So I want to like put this on pause. So people can go listen to that. You should. It's great. We get like the detailed 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. 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? I thought it would be something Chamath and I would do 10 times. Yeah. So the origin story is pretty simple. Chamath, I knew because he was running ICQ. Chamath was running ICQ? At AOL. And I had sold my company to AOL. And like the revolving door of AOL. I didn't know that was the lineage. It was like Ted Leonsis had this March to a Billion podcast.

uh my greek brother a mentor had this like march to a million a billion uh off site and so i went to this and i just sold weblogs like a million users hot that's the the that was the idea with that well with weblogs inc and with uh aol and other assets they wanted to buy they were going to march to a billion users yeah it was like this crazy rallying car and we had these t-shirts march to a billion so i go to that and i see chamath and i was like hey and he's like hey and we

introduce each other and we had known of each other and I said what are you doing here he's like I'm running ICQ into the ground you know I'm just writing it down every month it loses a million members it's hilarious and he's like yeah but I'm leaving I'm gonna go um

I'm going to go to the West Coast. I'm going to go work at this VC or whatever. I was like, all right, nice seeing you. And so then when he was there, I was in LA. What VC did he go work? Because he was at Facebook. 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 team. - He built the growth team and he was like, there is no equivalent of growth. 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 went into beast mode 'cause he too was very hungry.

You guys must have been like brothers from another moment. Yeah, for sure. We're definitely both outsiders in Silicon Valley. 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...

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? No. Not when I'm taking care of him. He was like a dork, you know? But he was... His Bezos pre... No, yeah, his Bezos pre... Yeah, whatever. You know, 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. Yeah.

and confident, 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 LA. He came on the pod.

And then people, I was like, he's really good on stage. Like, he's funny, whatever. And so... Which at this point you had an eye for. Sure, of course. I mean, one of the things when I was a podcaster in those early days, you know, I'm talking about 12 years ago, whatever, is, you know, I introduced a lot of people to the world. 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 person in 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. Plus I'll see. I'm going to go, I may go back down to five next year. It's a little much right now. Yeah, dude, I mean, we'll come back to this. We'll come back. You're killing yourself right now, and you're on act three. Yeah. I have more energy now than...

I may have... Just this coming out of the pandemic might have as much energy as I did when I was in my 20s, but for different reasons, different type of energy. Anyway, Chamath calls me 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 just pop 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 In. Like, we should come up with a poker name. He's like, yeah, great. Like, Arrays or something. I was like, All In. Because you'd been referring to this poker game on air on Twitter. Yeah, I would talk about it once in a while, the poker game that doesn't exist. And Sky Dayton and I had a poker game with Brooke Hammerling, the famous PR person, at the Code Conference, which was the All Things Deconference before that for 20 years. Right, right.

Then Chamath had a poker game. Sax, 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. Which is another funny story. Yeah.

And lots of funny stories in my life. But anyway, so then the pandemic happens and we're like... We're letting you go and just dropping these little breadcrumbs here. We got to pick them up. At some point, we got to pick these up. Anyway, at some point, I'll write a biography. Anyway, nine years. Third book. Anyway, then the pandemic starts to happen. We're like, well, Sacks has some ideas about masks. And then Friedberg... Sacks and Friedberg weren't...

There was no besties originally, right? No, no. It was just you and Chamath. And in truth, like, Freeburg 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 Freeburg is a bestie. 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 like, oh. 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,

Mmm, 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 more friends But the world does not want us to be friends in some ways the world wants us to be enemies and I kind of think about it like you know best of the enemies kind of situation like we debate specific things like Gore Vidal and

Who was his adversary? Anyway, it's a great documentary about Gore Vidal and William F. Buckley. They're just two public intellectuals. One was on the left, one was on the right. And there's this documentary, Best of Enemies. In the 60s, they started debating like different political conventions. It was like 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. Yeah.

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 sixties where like maybe some adults understood like, you know, that's a gay man, but we don't say that. When they got into town yesterday, we were driving the Castros right here by and we,

We saw a naked guy in the Castro, and I was like, oh, a naked guy in the Castro. Ben was like, what is going on? Dude, you've got to understand. No, it's the palimpsest nudity in the Castro. It's a huge, jacked dude walking around, and super sunny, so he's just all slick down, sweaty. But did he have his shoes on? Was he wearing combat boots? They usually wear boots. And then they usually carry a sarong. There was a big debate when I first moved up here because there was...

a number of folks who used to like to get a Starbucks and they had to like negotiate and they were like, how about a sarong in Starbucks? Cause you're going to sit. Right. Right. Bare ass. And for, for context, for, you know, I've explained this to Ben, but like, this is a thing in the Castro in San Francisco. It's a cult. It's like a,

It's a very accepting place. Now it's like you've seen this like, ah, this is like a relic of the 60s, 70s in San Francisco. Yeah, it actually was pretty awesome because David, we're like driving up and David goes, oh, a naked guy. It was the most like warm hearted. I had to 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 like high fives and right ons. But, you know, growing up in New York, like if somebody takes their clothes off on a,

public transportation or in a cafe, like people are getting a baseball bat and calling the police and like this shit's about to go down. Oh my gosh. You know, and then here it's like, you know, high five and live your life. That's one of the things I love about San Francisco. But anyway, the pod's gotten very big. So you get the gang together and like, why do you think it works? Why do you think it works? It's like the number one-ish band.

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 tech anymore yeah it has nothing to do with finance or tech anymore i think it works tipped over into colleges i was at i was you know skiing in tahoe and i you know i was with my kids and it's hard to get a table type situation i was like hey i hate to be a pest but i see you're wrapping up are you

and no pressure, but are you gonna be leaving soon? 'Cause I'd love to camp out here and get your table. - And they're like, "Stop busting my balls, Jason." - And the woman looked at me and she goes, "Jake Howell?" And I was like, "Have we met?" And she's like, "No, I listen to your pod twice a week." I'm like, "It's only on one." She's like, "I listen to it twice." And I was like, "Oh my God, that's so nice." She's 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. Can I ask how you found out about your... She's like, I don't know. She's like, I deeply care about San Francisco politics. No. It's not how she had found it. And this is during the pandemic situation. And then that's when I realized it had crossed over. It's definitely 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 micro-famous, micro-celebrity multiple times in my career. But this is different. In New York.

Not for me. And I got a lot of famous friends. I'm used to getting recognized. I'm used to people taking pictures. What I'll say is where it used to be, if I go to Austin or New York, people would say, I would have three people stop me on the street a day if I was walking around in New York.

Now it's 20, you know, or 10, and they want to take a selfie. And it's, you know, it's just, you know how podcasting is. You guys get recognized and it creates a level of intimacy with people. Oh, for sure. If they're in the habit. Yes. Because you're hearing people every week. And then people become characters. And I tried to make everybody, I was, you know, in all honesty. In all honesty, I did craft people.

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. 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, that's what I was going to say. And, you know, Freeberg didn't even have a Twitter handle. Zero followers. There's even a character of J. Cal on All In. J. Cal, the world's greatest moderator? Sure, yeah. I think more like J. Cal, the guy who lets himself be the punching bag because it plays for the show. A little bit.

Which is part of the world's great. If I'm being honest, I'd rather not be in the punching bag. They're like, you're the poorest guy on the show. I'm like, do we need to point that out so often, guys? You're like, not by much. I'm feeling really good about myself. You don't have to point out that you all have more money than me and two of you have planes and I don't. It's okay with me. I could have a plane, I guess. I could get one. 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... 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. Maybe it's a little bit of like them...

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

Before All In, Chamath had a little bit of a public presence. No, they were not famous. They had no go-to market. This is a new thing for each of them to hit this level of notoriety. It's not for me. We should ask them this, but if you were to speculate, caveat that it's speculation, what do you think for them All In has done? Well, I mean, for Freedberg...

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 and

You know, just say who your favorite bestie is and then direct a 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 Kirshner in. If you can't make it, I'll try to get Bill Gurley to show up or whoever Draymond.

to fill in for him you know and it was always like i wonder if freebird will show up but he's actually really committed to the show now um for sax he was high profile but nobody really knew him as a republican so he kind of uncloaked as a republican on the show well i feel like he was also like he was almost even more so than any you know well not you but he was high profile if you knew about the payfail mafia money but he was like the least kind of public of the

PayPal Mafia.

And I guess Saks would be somewhere in that strata of being known. Not success, being known. Being known, yeah. Being known. But yeah, I think part of the reason this works is Saks... I think Saks has probably taken the brunt of the head of the pod because he is so passionate about a lot of topics that maybe are unpopular in the tech circle. So I do think it's cost him deal flow on the margins, probably. I think there's probably...

I don't really marginally. I wonder. He said that jokingly on the show. I don't know. I'm just thinking like maybe there's somebody. Kraft has ascended because he's done all in. 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—

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

Giuliani when Brie was crazy and Pataki who are all Republicans. Were you here during the sports league 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, 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 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 can tell you that. My replies have been really crazy. I would get like brigaded the last couple weeks. It's 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. 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're going to play this game, I'm going to dub you David the Dove. And now you're making me into Jason the Hawk? Like,

What are we talking about here? But anyway, you know. Well, it just goes to show how silly the coalition building is. It's totally silly, exactly. The two-party system requires that if you feel very strongly about something, then you're not allowed to think independently about anything else. It's so crazy. 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 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 I would hate him as a Democrat or a Republican. So it's not personal, and I would love to see it. Or it is personal with him, but it's not personal with the party. It's very personal with him, yeah. I mean, I just think this is just a horrible human being 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 something

in something. And for some people, that's the flat earth. And for other people, that's startups. And for some people, it's... It's a tribe. Yeah. We don't, you know, a lot of people don't practice religion anymore. And so he's their religion. Yeah.

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 because it really is pretty it is pretty but like I got to be part of a tribe and

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, learn from each other and have a vibrant debate, which is how we all grew up, I think. When I say we, including you guys, but also specifically the besties.

I want to be friends with people who I disagree with. I want to debate stuff. Right. And then people are like this guy, Dean Preston. And, um, it's like one of these supervisors here is a super idiot, like guy in San Francisco who like, um, you know, like won't let them build housing and all that stuff. And he's like, you're just a conservative, blah, blah, blah. And I was like,

You don't actually understand who I am. He's like, you're a conservative billionaire. I'm like, wrong on both accounts. Thank you for the latter. My besties remind me on the latter. Yeah, I'm working on it. I'm working on it. Not trying to be a billionaire. Thank you. On that, another thing that's really fascinating to me about All In and you guys is before All In, and still to a large extent, I feel like Silicon Valley...

has this weird relationship with money. Like, super weird relationship with money. Like, you know, remember there's a whole thing about, like, Zuck drove, like, an Acura SUV. Oh, my God, 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 like what I'm like we got a private jet like that's fine like you know, I mean listen I You know, yeah, I believe in capitalism I think it's great if people create jobs and if they get rewards for doing so like fine I have literally the book I'm right my second book right now I'm writing is about wealth and money and like but not like in my regard but in a sort of like big picture societal regard so I'm like literally been thinking about this topic a ton and

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 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 flip it, you can build a business there.

David Senra over at the Founders Podcast, Mr. Beast, MKBHD. Nobody gave these guys permission. The world has never been this equitable. Yeah. But people want to spread a narrative that the world is unfair. And 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 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. And it typically is a certain type of person. I'll just leave it at that.

Okay, can I? So I'm going to leave it at that. I teach Foundry 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. 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% of people complete it. That's cool. So, and then we're investing 25K in some of those folks to help them start their companies. People don't know all the work I'm doing like quietly, but like 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. You have to have gone to Stanford. I'm like, no, I'm invested in 350 companies. Like,

Maybe 5% of the founders went to Stanford. Like, no, that's just not, it's patently false. Like, you know, you have some confirmation bias. You're dealing with a data set from 10, 20 years ago. I get it.

But I'm telling you, on the streets, ground level truth. We all meet with founders all day. It's never been more diverse. It's never been more open. Nobody cares where you went to school. Nobody cares where you live anymore. Nobody cares where you live. They care about what you've built and your traction. It is post-pandemic. All people care about is like, show me your metrics. Show me the product. Show me your team. What are your skills? Great, let's go. What's your growth rate? It's basically become...

Like, as beautiful of a meritocracy as I've ever seen, 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 answer your question earlier of why I think all in works? Yes. All right. Go ahead. So I think you've got the perfect storm of three things. The first thing is... A lot of theories on this out there, by the way. Billionaire porn. Billionaire porn.

Most people, you're counter-positioned. Most people who attain that level of wealth...

crawl into a quiet hole and make sure no one knows about the private jets. You're doing shows from boats and jets. Yeah. So there's like... I don't think we've done one from a jet, but yeah, there was definitely two boats in the last two years. That's true. Not my boat. In some peak moments of All In, it's like watching billions in real life. It's like you hear Chamath talk about this spread trade and you're like, this guy's got a lot of money on that spread trade. And like, does he actually have a key insight here? And like, there's this interesting intrigue there. So Bucket One is like billionaire porn. Yeah.

Bucket two is by the research you guys do and the folks that you each work with, because there's definitely researchers that seem to be involved, you bring things to the table that are like,

brand new insights that aren't widely available yet. So I feel like I was learning things about COVID-19 on all in that I wasn't getting through any other source. I'm like, 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 could inform us. How many people are,

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 your text files open on people's computers when they're talking? We have a docket with the notes, but that's mainly for me to queue it up. Like I just read the four or five bullet points so people know it. So I do that with my team, the docket. But the docket is built from...

you know, the five or six stories that people submit to our group chat and say, hey, put this on the docket. And I think Saks has some research help. I'm sure Friedberg and Chamath read the stories or they're well-read. All of us read constantly and we're in the information business of talking to people.

about the world. So you guys are investors. You know how it is. You do 20 meetings a week with founders. They're going to tell you everything about the world. 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 5% 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%. Or even on the inside, you might only have 50%, depending. You get enough to run with and you feel like, OK, now there's enough story here. Let's do it. And that's clearly not the whole story, but it's enough to put the piece together. And then over time, process journalism, as some people have dubbed it, maybe the six or seven stories will tell the full story. Yeah. Yeah.

Which a 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 1% content, find it compelling. It's just, yeah, that's right. Listen every week. Don't miss it. I can't really walk in the baby up and down the Hills. Listen, 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. Uh,

But, you know, I'm a shooting guard too, so sometimes I will want to shoot the ball. And I can do both. I'm a combo guard. How did the Freeberg host episode come about? So one week 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 pass the rock and I'll... I was like, yeah, you want to be a combo guard? Go ahead, show us. And he did a solid job. But let's be honest. He's not a point guard.

It's not Showtime, that's for sure. 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, I mean, but he shines when I created Science Quarter for him to shine. I said, bring me a science. He's like, oh, you know, I don't know if I want to talk about politics. I was like, listen, Sax wants to talk about current events politics.

I'm giving him his red meat. Here's your quinoa. Come to me with a science story, you know, and we'll do this quinoa corner kind of thing. And I've made him the Sultan of science. And so good. You know, it was, it was a distinct effort. I really wanted to make him shine, you know, and it worked, you know, it worked because you see how engaged he is. And what used to happen was, and fans know this, I'm not speaking out of school here. You see it every episode. Sacks would disengage during science and quinoa. Yeah.

And what I've been trying to do is keep both of them involved when the other is doing stuff. And Chamath and I are involved. That's a hard job. That's a delicate. I studied the McLaughlin group. People don't know this, but I went back to look at McLaughlin and I watched him moderate. So people, there's a big debate. Do I interrupt too much or not enough? Do my interruptions, I call them interjections,

do they help? And I actually looked at the interjections and if you look at McLaughlin, you guys did not grow up on McLaughlin. - I'm super unfamiliar with what this is. - So the McLaughlin group was like the best Sunday morning show. And like it was so good, like SNL would parody McLaughlin. It probably had a million people watching it, but this guy McLaughlin was like pretty cantankerous. And if he didn't like what people would say, he'd be like, "Wrong, this is the answer." You know, like, and it became so competitive that you wanted to watch it. - Yeah.

What I didn't realize by adopting that would be that Sax is the ultimate debater and will fight like a dog until he wins any debate. And so I may have pushed Sax 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 where

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...

you know, fair market value when they hear an acronym in me. So I'm like, explain that. Right. And I'll stop somebody. Now, I mean, you're, you're expanding the TAM to dentists. Like that's correct. Thank you. So people are like, Oh, J. Kyle's an idiot. He doesn't know that term. Or I say to somebody, can you unpack that? Can you explain that?

Obviously, you know that term. Doing that for myself. You were, what, the third or fourth investor in Uber? Yeah, like, exactly. Well played. I think he's been in Robin Hood, too. Oh, gone, too? Wow, who knows? And I'm like, dude, like, I'm asking that question on behalf of the audience. So when I'm moderating, as opposed to being an interviewer, or as opposed when I'm working with Molly and we're chopping up the news, when I'm the shooter there, right, and she's maybe playing point guard a little bit, and I'm shooting, and then sometimes I'll pass it to her and she shoots, I'm like,

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. Yeah.

And that's what I think has brought in, to your point, a lot of the dentist crowd. And having an intimate sense of where your audience's edges are is a really important role there. It's an art. Like when we have guests on, I'm always trying to catch where did they just go slightly too deep and I need to pull them up so that we... Yeah. And, you know, podcasting 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 like if they just jump in, you're like, oh God, no one has any context. They can't learn anything new because you're like, you're not connecting it to something they understand. They just jumped into brain surgery. Yes. Let's just explain to us what's going on here. How are we going to chop up this brain? Right. Like, yeah. Yeah.

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

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. Right. Let me make sure I get what he's saying here. Or I can listen to the talk show with John Gruber and it's just like,

If I missed out on 20 minutes because I was like brushing my teeth and then I left the room and I came back and I'm like, oh, I didn't actually miss anything because this has just been like... It's comforting. It's like I love all the stuff he's talking about, but like it's not...

I 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 mean, wait, related, but separate topic. Um,

Silicon Valley. Yeah, I feel like especially there's a lot of Part of the origins of all and there's a lot of like bashing on San Francisco politics and Calvin like there's a lot of crap wrong here Yeah, but you guys are all still here. How are you guys feeling about it? Yeah, how do you how do you feel about that? Like what? What do you think of the Bay Area? You know, I lived in New York Brooklyn, Manhattan and then I lived in LA and then I lived here and so

I think I'm moving to places I enjoy less and less each time. I enjoyed Brooklyn and Manhattan much more than L.A. I enjoyed L.A. much more than San Francisco. 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 L.A.,

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

What have you had me do to you, J-Cal? 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 or...

I think the politics and not appreciating the politics, the regulation, and not appreciating the tech industry is really the problem. And then you look at this guy, Dean,

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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 $1.2 million. 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 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. Yeah.

from their RSUs? Like, are you such a... 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...

It's just insane. It's just insane. Like what? I mean, you could go change the tax code. It's fine. Like, you know, raise the minimum wage like Bernie Sanders and Elizabeth Warren attacking Bezos endlessly. And then Amazon starts paying 22 an hour, gives you benefits and pays for your college. And it's like, OK, hold on a second. I know what Bezos just did. He took the platform that you could never actually enact and he enacted it inside of

Amazon. If it's not perfectly clear what just happened, literally he's dunking on you. You wanted free college and couldn't get it done. He gave it to Amazon employees. You wanted a $15 minimum wage. He made it $22. And you wanted everybody to have universal health care, and he gave universal health care. That is literally what Bezos did to them. How embarrassing for them. Maybe you could argue that them pushing him pushed it, but... No, no. Definitely, it is literally him showing, as the Amazon crew showing, let the free markets work. Yeah.

The DoorDash, Uber, Amazon, Starbucks absolute race and battle to just hire entry-level employees and make it delightful for them is what has driven...

And a lack of immigration is what has driven these salaries up, right? And the benefits up. It's extraordinary what's happened with the free market. 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.

All right, 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 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. The data being integrated lets them do really great stuff to like...

You 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 Rex. Yeah, like...

Globally, 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 like 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 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 out of 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. You know, thinking about the world and having these conversations. I had Toby from Shopify on today. Like, I leave the Toby interview. It's like his third or fourth time on the pod. That's awesome. And it's just like, instead of us having dinner or lunch, we just record a pod.

The end. Did you do it in person or did he? No, just popped on Zoom. You know, I had to start it because he did that tweet about his compensation tool where, you know, here's your total comps, use a 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 11,000.

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, 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. I don't know either. 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, Foundry 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, 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 in my career as an angel investor. I'm doing 50 million a year now. That's awesome. I'm raising the fourth fund in public. Like,

11 000 angels in the syndicate like this is going at a really significant velocity if you were to look at the slope it's not quite a hockey stick but it's hockey stick-esque in terms of the total capital i've deployed and it's in really high quality companies i'm getting better at there's 11 i have 22 people and 10 on the media side 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. 6-0. 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. 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

unhealthy desire in my youth to be successful. And if they did, they probably wouldn't come work for me, but maybe they would. Actually, I would. So yeah, they probably would. - Not for very long. - Yeah, mine might be like three years ago. - You'd come, you'd learn, you'd extract. - It's our father too. People come and they work for two, three, four years and they go start their own venture fund or whatever. Mazel tov, 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. You teach the course. Are you enjoying the LP fundraising? I am now, yeah. I'm kind of like... Remember in X? I don't know if you watch Billions. Oh, yeah. Every episode. Great. So, you know, like at some point...

He was like, I'm gonna go raise money. Yeah, it's cap raise time. It's cap raise time and like WAGs is like so I got my WAGs Mike Savino's my WAGs Yeah, and I got my WAGs who just fixes everything and I'm like, I'm gonna go raise money And so literally was like we're doing 506c and they're like, and so you've talked about this now You're you're now you were in kind of this one bucket with your capital and now you're going simultaneously in two directions of you want the public and

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. Wow. That was my first fund. It was 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, 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. 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 aspiring VCs raise publicly. Right. You didn't raise publicly. No. You did 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, he

Yeah, you did a great episode with him. Yeah, it was great. I had him on. I had first-time founders for a season of Angel, which is like a subsection of the This Week in Service podcast. And I became an LPN's fund. And he just told me, I just did hundreds of meetings. I did five meetings a day for a year. And I raised my whatever, $10 million. And he's African-American. And he's like,

it's just a matter of how hard do you want to work and I'm like 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 AngelList you set it up and then you just start talking to other VCs you talk to them and you just you just have to be willing to take 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

easy but on the internet too you find your people who believe that with you and then they believe in you and then they back you and that's the correct correct and so the whole thing but what i noted when i was taking my notes watching him was so many times people like oh you're when's your next fund i'm like three years they're like oh let me know and i'm like okay

Right. I'll put that right there in the place where I keep everyone who tells me. Yeah, three years from now what to do. Yeah. And so, you know, I mentioned it on All In. I tweeted it and all of a sudden, you know, I had a thousand people sign up. Is there a limit to the number of LPs you 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. Yeah.

To catch everyone up. Qualified purchasers. Look at you playing Jason. I know you know what a QP is. I just want 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.

accreditation and you'll be able to be sophisticated if you take a course. So I think that's coming in the coming year. So just like I democratized angel investing was the book angel was the first syndicate on AngelList the most successful syndicate on AngelList 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 and

I don't know. I mean, now as a participant of a fund on AngelList, like these are like, those are big numbers. Like we've done- You do something consistently. Four SPPs on AngelList and we have the fund too, but like, 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's the time to democratize venture capital. So that's what I'm attempting to do here is I want more people who are accredited and qualified purchasers who've never been in a venture fund to

to look at the asset class and just consider it. Um, it's high risk. It's high reward. I'm in 20 venture funds myself, including yours. Thank you. Um, and I'm sure, but don't pitch Jason. I'm sure I will do yours. No, I mean, I, I'm just going to pick them based on people I know or people I know online or pod. And yeah, I'll do one or two new ones a year. And, um,

Well, this is kind 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. You could create Founder University. Whatever it is. You can do any of those things. 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 like the idea of having some institution be like, can we invest $15 million? Oh, yeah, of course. I mean, I've had $5 million checks, $10 million checks in the fund from fund to funds and institutions, you know. But I would very much at some point, I don't need it, but it would be meaningful for me, both my parents are cancer survivors, to have...

memorial Sloan Kettering's endowment or an endowment or something like that. Somebody like that, you know, if they wanted, I would work, you know, really hard to try to get them a great return. I would find more, I would find even more meaning in what I do. Uh, and I, you know, I got that from Sequoia, like, you know, you, they would have this Sequoia dinner every year for the founders and they would say, here are what the foundations who are LPs, uh,

are doing with the money you made for them with your companies yeah click click here's what four foundations doing here's what this foundations are his and you're just their conference rooms are named after their and that conference is famous and it's like and this is real powerful like i i find we have like state pension funds and stuff like that and that'll make you get in psl ventures and like you take it much more seriously you're like i am it's because it's not just about the reward it's not like oh i 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 going to be a family office. No, I'm going to raise my own phone. Right. And so there's this natural tension for acts like, which should it be? And he decided, well,

Yeah, I like when I have other people's money because he seemed to perceive like... I think he felt that he wasn't a somebody in his ecosystem, in his community, without managing outside capital. I think it's like playing, you know, in the bubble with nobody in the stands versus getting on the court at Madison Square Garden 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, or I should say quasi-public, people that still have to sign up to, you know, come to a webinar. Yeah.

But I'm sharing with them, like, here's the totality of my investments, and here's what I've done, and here's what I plan on doing with my team. So, you know, I'm kind of enjoying it. And...

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. Small fund. We're a $50 billion endowment. Yeah. And, you know, like, you know, at some point, like one of the ones who's the most rigorous, I wouldn't say exactly which one was like, we have a lot of respect for you. We know who you are.

People would like you to sign a book and take a selfie with you when you're here. But I just want to be straight with you. We don't add many funds. And if you go through our process, it's going to take a lot of your time. And it's going to result in you not getting our money this time. I don't want to put you through that. But I respect you. 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. And literally, I did the second call this week, the first one last week. I'm doing the third one next week. And it's been so productive. I added two more. So I'm going to do five webinars this fall. And then I'm going to go on the road and start meeting with folks. Are there any downsides to doing the raising in public thing other than... Not that I can see. I mean, I guess you could fail in public to fail to raise the fund. That doesn't seem like something you're scared of.

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. Literally, it's so funny hearing you say this.

myself, lots of our other friends in the ecosystem that are in similar positions, they're having this same question. Like on the one hand, I could do what you just said and do very little work, but have it all be pure. On the other, I could go do what you are actually doing and like raise, have LPs be accountable. Yeah. How did you weigh these two? I'm going into my second era, my second decade of investing, basically.

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 don't mean to be obnoxious about this. I know it probably sounds that way. But for a kid who's, you know, going to be a cop to be where I am. And this is why I like when the guys break my chops on the pod. I'm like, guys, I don't aspire to.

To be a billionaire, it's not important to me. If it was, I would do a late stage fund. I aspire to be happy and do what I love doing every day, which is the podcast. Maybe get in 40 days of skiing, hang out with my kids, take them on the mountain, and then meet with early founders and be able to say, I helped that company at the earliest stages. That, to me, is the rush.

I found him first. I backed him first. I sat there with him and figured it out with him. We were talking about the legendary twist episode 180 with you and Travis. Yes. Like, man. That's the secret before the show stuff, David. Yeah, that is. But from the juicy before the show. I can talk about Travis. Yeah, but that was like, you know, Urbu was such a baby company back then. One city. One city. I invested and I had an open angel for him where...

and Chris Fralick from First Run invested in the company. I think they both met them there. Sokka was there too, but he already had a relationship with Travis, so I can't take any credit for that. And Kevin Systrom was watching, and I was gonna kick him out because he was at this co-working space called Dog Pats. I worked there too. I worked at CoTweet. Yeah, so he was, oh, CoTweet, I know that. So he's sitting over there building bourbon, and Sokka's like, can bourbon come in? I'm like, fuck no, this is like private shit.

And he's like, but, and I'm like, just tell him to sit at his desk and I won't kick him out. Wait, this open angel forum was at dog patch labs here on the pier. No way. Then they shut down because it was going to collapse. Yeah. Condemned. Um, so that was there. And, uh, also did a bunch of like events there for angel. I, at the time, Naval and I were very friendly. Um,

Not friendly now, but we don't hang out, but we used to hang. Kind of bummed about that, if I'm being honest. I really respect him. And he was doing something called venture hacks at the time. So he would just send an email to...

with here are the five companies and I was doing it in person and he's like I'm gonna do this thing AngelList I'm like well I'm doing this in person thing and he's like great let's just you know trade notes or whatever and then he sent me the syndicate thing he's like do you know about SPVs I was like I don't explain it to me he taught me what SPVs were he introduced me to Assure Fund Management which I wound up investing in did you buy that I didn't buy it I mean I bought 5% of the company I invested in it but they back everybody and

they've done more SPVs like 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 looking for 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 we were some ridiculous multiple on a return But then there's these other ones that are like promising but early and then there's other ones where it's been a less than uber multiple It's still good an uber multiple, but you look at calm and

you just, I looked at David and I was like, he sharpshootered that one. That one I could be even more proud of because I'll tell you why. It was like ridiculously early and like a super low basis. They had, it was $4 million. We put 370 AK in on 6% and they didn't raise any money until it was a $250 million valuation. So no dilution. Sharpshooter. Sharpshooter. And,

It's like Vantam. Vantam is the same story. I could even cry telling the story. But Alex, too, and I became very good friends. And Michael Acton afterwards because he wasn't actively running Calm while Alex was. Alex, at some conference, I was interviewing him and doing a little victory lap for him and giving him his flowers. And he said, 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 through your money. Yes, I think so. I think so. Because you're like, take more of my money. No, no. But I mean, if you think about that as like a...

That is not the case with Uber or Robinhood. I was along for the ride. Let's be honest. I did not change the trajectory of those companies. But for Jason Calacanis, Calm was not... That's what they said. 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 lot of individuals participating in venture rounds. Party rounds.

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— $10,000 in revenue to date, I think, when I invested. Like ever. 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. The person had it for life. 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. It's like making Microsoft...

Word 1.0, you buy it, you throw it away. It's like, but we can just update it. And it's like, yeah, but we need to make more money. So shut the old one down. So you'd buy Angry Birds and you buy Angry Birds 2, Angry Birds 3. And, you know, it was a really weird time. And then they're like, yeah, we're doing... They told me like, you know, because, you know, I was under NDA as well. You know, hey, subscriptions are coming. That's going to change everything. And they were going to do $10 a year. And I said to Alex and Michael...

How much does it cost to go to a meditation class? It's donation-based, and there's only like 10 places you can go. I'm like, well, what's a suggested donation? It's like $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. 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. I was like, so it's $80 a month.

to go and we're charging $10 a year. So that's like a thousand dollars a year versus $10. What if it was $10 a month? They're like, we've been thinking about that. I was like, okay. And they're like, okay, yeah, I think we're going to do that. And then they went to $10 a month or whatever. And they didn't wind up at $60 a year, whatever it was. But it became a money printing machine pretty quickly. So I've never made an investment at like pre-product market fit that's like now worth over a billion dollars. That's a very early to very successful. And I'm curious,

Did it feel any different when you were making that investment? Were you like, there's something more special here 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? When you look back and you're like- Nine factors. Nine factors. Okay. All right.

Well, angel.university. No, I don't even teach at an 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. 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 doesn't take a rocket science to look at them. But when I first explained this to my team, they would bring me companies that

And they'd say, world-class design. And I'm like, I really like the design. I'm like, pull it up. And they pull it up. And I'm like, that's a template from, 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 I was like,

Okay, yeah, again, that's just like the, I mean, if this was a bank's website, maybe, but that's not world-class. That's serviceable design. That's utilitarian design. That's okay design. That's good design. It's not world-class. So let's, if we're going to say world-class, like a world-class performance is different than a serviceable performance. World-class cinematography, world-class script, world-class dialogue, that's different.

And then product velocity is the other one I like. So, okay, we met with this company in June. It's now July. What's changed about the product? And they're like, we don't know. I'm like, okay, well, let's find out. Where's their 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 this. And then a month later, they're like, check, check, check. And then you go like, or with Ro, with Superhuman, and I was an investor in his company before that report of Ro, 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 Rahul 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 why? Outlook support. You just don't, you know, when you hit Command K, 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. Which it was all there when I started using it. Three, four years ago. I think a lot of those things have gotten better and better. Yeah. So it's just that, like, polish, polish, polish, polish, polish.

I really like want them to make snippets multiplayer. I want to share my snippets. Oh, yeah. Oh, with your team? I love... I want all of David's pass 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. I don't email anybody. I actually do have all your pass emails. I've been literally creating a collection of how to pass with my team and I'm standardizing that.

I'm trying to, I don't know that I'll be successful and this may be a mistake, but I'm trying to just not have, I don't end up having a conversation with the company if I'm not going to invest. No, but you must say, hey, we are not going to invest. You've took a pitch. Oh, no, I get it. I don't. You basically don't take a pitch unless you're going to invest. It's the weirdest thing. Oh, that's very weird. So you do all your work upfront? Yeah.

You front load it, the deck, everything? We're in this unique position. You are too. But 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. It's Modern Treasury and it's Pilot and Vouch. And I'm now an investor in just about all of those companies. Okay, 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. 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, depending on 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 Semiconductor. Stitch Fix was the other one. No, Stitch Fix wasn't yours. Twilio. Twilio was yours, and I love that one, too. And I like Shopify as a pick. I'm actually really enjoying it. It's really balancing out... Not investment advice? Not investment advice, but it's balancing out my...

understanding of what public success is compared to private. And so for me, it's just a way, like, am I going to fight with a blaster? No, I'm a Jedi. I use a lightsaber. But, you know, I'll learn if you use a blaster. 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 sure they all trade public stocks yes and they do it for this same reason they're gonna fight with the saber yeah but like they want to know how to also use a blaster or how to fight in an x-wing or something like it's not what a jedi does but jedi will do it it also keeps you really sensitive to the public cycles so that like yes it's not that you have to

think about the public comps when you're investing, but you have to be aware of how much those will change. And early stage investing, it's almost silly to compare to, like my opinion is it's very silly to compare to public comps because the only thing you know for sure is we're going to be at a different place in the cycle by the time this company gets liquid. So...

It's ridiculous, but it's helpful to drive into you like how much variability there is. When was the last time it was this different? That's what 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. So it, you know, I'd like to join a public board at some point. It probably not a good idea for me to have said that cause I might get an invite for one and that might be too much work. But, um,

Yeah. But especially given the market right now, I'm,

Better be careful. But you could also be. Somebody might invite me to do that. But it's just, it's been great. Especially through the show now. You have relationships with public company founders. Sure, of course. That you can. I mean, if I really wanted to, I'm sure I could lobby. Oh, I'm going to say, you don't have to be on the board, though. You can have a great relationship with. Yeah, I'm just enjoying doing the analysis. And I'm doing it anyway with Molly every day. Okay, you know, Twilio's or Adobe's. I just bought Adobe this week when they bought Figma. It's so funny. So did I. Not investment advice. Not investment advice. But I was like. They bought Figma tanked.

Okay, so here's my theory on this. They bought Figma and tanked. And I was like, why do people hate this? And they're like, oh no, Adobe's admitting defeat and that they can't innovate in-house. And to me,

I look at it like Adobe has customer channel and it was foretold five plus years ago that they were not going to build the next Figma. 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,

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. Like WhatsApp. WhatsApp. Just leave it alone. Don't screw it up. And then, so I like your analysis. I added to that analysis is,

If you're not going to win the war,

You can build an alliance and then fight another war like they've just removed the downside Yeah, a Figma creating Photoshop. I'd be concerned for Adobe if fig they didn't buy figma, correct? So the fact that you're giving us a discount on the shares for them doing the right thing is like Christmas like thank you Yeah, you just discounted the right move Fantastic would be like people are like, oh, you know the Warriors signed Kevin Durant and

And you know what? We're going to lower the cost. But they paid a lot to get them on the team. Yeah. And oh, you know what? We're going to lower the cost of the tickets. OK. 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 yeah. And they have a free Canva.

already. And what if there's always the internal people who are penciling out that spreadsheet? There's a group of MBAs who penciled out that spreadsheet with Figma, no offense to MBAs who are listening. And they said, hey boss, if X, Y, if X, Y, Z, and they said, here's like five potential paths. If we make Figma free,

for 10 users and whatever, or if we, you know, take whatever Figma costs and then we blend it with the Adobe suite, uh,

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... But when you look at Figma, like, I got a Figma account. Like, people who are...

giving feedback on designs, the business side, the sales side can get into Figma. Plus they got the whole creator class. Exactly. So I think you're opening up the aperture of who design software is for with Figma. It's for BD. It's for the CEO. Sure, the CFO can come in and take a look at the product. Oh, legal should come in and take a look at the product. Yeah, buy them a seat. So it's like Slack is for the dev team. And it's like, yeah, and the sales team and ops.

And anybody else might as well be on there because that's where everybody is. So that's what I think is 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 $100 a year? It's the cost of doing business. Any company that has that kind of strong network effects inside an organization deserves a meaningful revenue multiple because their differentiator is literally the company's moat. So I tweeted this, but 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.

Hundred percent like the virality of it I think sacks made this point on all in two weeks ago Which was like if they're paying 50x now and the company's growing, okay, they're paying 20x next year. Yeah 25x who cares right using such a high growth company and then I was just thinking well somebody's got a theory there and When I sold web logs to a well people were like, oh my god, these people are idiots They gave 30 million dollars to you know for web logs Inc They've only got 200k in revenue what they didn't realize was a well autos a well tech is

AOL lifestyle those were sold out at like a $90 RPM revenue per thousand pages 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 fifty or a hundred thousand dollars in ads a day on a blog and

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 makes sense. God, 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. Holy crap. Over the 18 months. What a deal. I mean, now, like, the world we're in today. People looked at the multiple, and they were like, J. Cal just robbed. And I was like, what?

Okay, no. $30 million sale? I look like an idiot. What do you think? I look like an idiot five years later. And that's the best M&A is when you look like you robbed the bank and then five years later it looks like you robbed the founder. YouTube. Instagram. Figma will be in this category. Yeah, when they 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 $150,000 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 like let's not make money from it part of part of the delightfulness of it Is that we're not trying to monetize it well, but but you do get a huge economic value out of it Shemak pull me aside at some point and was like hey Shemak like just we're friends like yeah, you're all your next fun won't be bigger Hey dumbass, yeah, I was like, you know when you have a friend who can be like a dumbass Yeah, like that's a good friend. So I appreciate you not saying that and he's right and it's playing out and we had a rule no

No talking our books on the pod. But we kind of talked about it. We're like, the pod is great when we talk about our bets. So explaining our bets, not talking our book is the new philosophy. So like, Freeberg just talked about his SPAC.

You know, I embrace call. Freeberg still has his back. Yeah, he did. He just found a target for it. Chamath talked about the healthcare company. The healthcare 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 over-prescribing these drugs to kids, like for ADHD and attention drugs and adults are taking too many. I think that that's not disputable. I think all the science is showing that.

So, you know, to make software that could help kids with ADHD is like noble. But I think people want to hear us explain our bets. So, you know, explaining our bets, I think, is kind of a cool aspect of the show. Talking your book is lame, but explaining your bets is cool. So anyway, in the event, did a couple million dollars, had a small profit. But it was the number one tech event of the year by far. Right. So, you know, I'm kind of bummed that...

You know, Freeburg'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, no, I talked to Bankoff about it, and he's been very public. You know, Kara Swisher, I think, is going to do the pivot stuff and wants to do other stuff. And, you know, she's... I really respect what Kara has done, you know, in terms of, like, she does stuff, and then she moves on to the next thing and tries. Like, you know, it's kind of my approach as well, which is, like,

Bob Dylan said, 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.

you know, very smallest. And so- Which you're definitely on. I am? You think?

How could you not be honest? I mean, I'm not even saying that to make you feel like... No, I'm joking. I'm being a little bit facetious. Okay, okay. You're joking about being humble. I'm trying to joke about being humble. 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, we've had our issues. We've all had 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 agreed 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 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. Yeah.

- Partially, exactly. So, you know, it's up to the boys if they want to do it, but it was like a pretty great success. - Call-in, you already have call-in, so. - Well, yeah, and I started doing a call-in show called After All In for the last two episodes where I took calls about the last episode of All In, just to support David because I don't think people remember how great that app is. It's really made great progress, so I want to be supportive of him, and I have a small investment in it, and it's very meaningful.

On the one hand, this is ridiculous. On the other hand, it might be ridiculously low. It's worth $50 million, to answer your question. $50 to $100 million. I mean, as a top 40 podcast, it's worth at least $50 million. On its own, though. But I mean, like, economic value that the four of you... Oh, who knows? Over the lifetime. I mean, if Chamath...

If Chamath or Sachs or I or Friedberg were to get but one more deal out of it, and it's an Uber, the economic value is nine figures, possibly 10. But that's the thing. I think, man, weblogs, you were doing 200K of revenue. You sold it for 30 million. Pretty great takeaway, yeah.

And now look at this. Yeah, I mean, listen, I hope it keeps going. I hope we can keep it on track. And I love doing pods. This Week in Startups is a juggernaut as well. It's been sold out for 10 years and all in is... What is that, like quarter million listeners or something? Yeah, something in that range, yeah. I mean, it's hundreds of thousands per episode. And it's a very niche podcast. I'm not trying to make it all in. I'm trying to make it for founders. And so if...

In order to make it bigger, it'd have to be worse for founders. Right. And that's what we talk about. It's like what we think about with our show. I want founders and capital allocators to listen to it. Our sponsor for this episode is a brand new one for us. Statsig. So many of you reached out to them after hearing their CEO Vijay on ACQ2 that we are partnering with them as a sponsor of Acquired. Yeah. For those of you who haven't listened, Vijay's story is amazing.

Before founding Statsig, Vijay spent 10 years at Facebook, where he led the development of their mobile app ad product, which, as you all know, went on to become a huge part of their business. He also had a front row seat to all of the incredible product engineering tools that let Facebook continuously experiment and roll out product features to billions of users around the world. Yep. Yep. Yep.

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So what does that actually mean? It lets you tie a new feature that you just shipped to a core metric in your business and then instantly know if it made a difference or not in how your customers use your product. It's super cool. Statsig lets you make actual data-driven decisions about product changes instantly.

test them with different user groups around the world, and get statistically accurate reporting on the impact. Customers include Notion, Brex, OpenAI, Flipkart, Figma, Microsoft, and Cruise Automation. There are like so many more that we could name. I mean, I'm looking at the list, Plex and Vercel, friends of the show at Rec Room, Vanta. They like literally have hundreds of customers now. Also, Statsig is a great platform.

for rolling out and testing AI product features. So for anyone who's used Notion's awesome generative AI features and watched how fast that product has evolved, all of that was managed with Statsig. MARK MIRCHANDANI: Yep. If you're experimenting with new AI features for your product and you want to know if it's really making a difference for your KPIs, Statsig is awesome for that.

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I'm not trying to move up the rankings. I don't mind hanging with all and being number one in tech and then hanging out with you guys at 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. That's where we belong with these things, right? It's a niche podcast by definition, right? It's not supposed to appeal to everybody. If you want to appeal to everybody, read the Bible. Right. If you go to the This is the Beauty of Internet. There's a guy who reads Bible passages. That's huge. It's like if you can literally— True crime. True crime. Religion. Read the Bible or Ben Shapiro dunking on libs. The end. The end.

That's how you get it. Or do it daily. But Joe Rogan's out, right? 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 outliers with Molly. You know what would be a fun acquired episode is Howard Stern. I feel like it's underappreciated how much Howard Stern I copied my that's the playbook that should be the next Taylor Swift type episode that we do. Yeah, no for sure. He wrote the playbook for all of us. 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 interviewer. Great interviewer. Great interviewer. 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 an 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 Bowie and, but I mean, he got 10,000 people to show up and buy tickets to a tennis match that they pumped up, you know, like for whatever number of months. I remember this from my childhood. And then he did his books, uh,

which were phenomenal. And he did a movie. He did a movie. He did TV shows. So he's done a lot of stuff. And I'm just starting the process of doing a reality show right now. So I'm literally going to do it. Are you really? Yeah. Just you or the besties? No, just me. The besties don't want to do it. They don't have time for it. I mean, there was talk of like maybe all in, you know, kind of going on to one of those services. Like people had reached out like, hey, would this work?

That's a lot more work, though. Well, we would have to show up in a location. We'd have to do it weekly. 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 Burnett had reached out early on when it was Dragon's Den. Right. Before when they were going to bring it here. So when it was Dragon's Den, they had reached out early. But I wasn't very successful back then. 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, 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. 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,

What was really good was really about me incubating companies. And they spent like $400,000 or $500,000 doing the pilot. It was really good. And it would have been a big hit. Did it get canceled because of the Harvey Weinstein stuff? Yeah, because of the Weinstein stuff. 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. That's right. I forgot. Yeah, that had the TWC at the beginning. Exactly. So, you know, NBC bought the show in the room, loved it, and did the pilot. It came close. And Chamath was on that episode, actually. He did the pilot with me. Oh, my God. He was like my VC friend who came in. My VC friend. No, it's hilarious. But I'm excited.

To do it, if it works out, it works out. If it doesn't, you know, no skin off my back. But I like the media space. And then, you know, I, this is the thing, I'm choosing to do media because I get joy out of it. I'm 51 now. I'll be gone soon. Like, I want to enjoy. You will not be gone soon. Well, you know, you never know. And, yeah.

Well, you've mentioned your friends, yeah. I have two friends who died young and I'm just like, I talked to my wife, I was like, I don't know, 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. So when the guys break my chops about that, I'm like, guys, it's not my priority. Literally, maximizing money is like number one. You're probably at a point now where like, it's literally not in the top 10. What is more money going to do? It seems unlikely. You don't want to play. You guys understand my life. It is ridiculous and charmed. Like,

Like 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 about like a third home. Like I have a ski house. I have my regular house. It's good. I'm good. My kids have their college paid for. Do you actually feel that way? I am good. 100%. I literally do not care about more money. Do you feel like that's a demon that you fight? No. Is like 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 have, I do want to, you know, be the greatest investor of all time. Yeah. Like to me, that's meaningful or be one of the, I want to be,

Like I know I'm Mount Rushmore for angels. Yeah. I want to be Mount Rushmore for all investors. So when you guys do your thing in 10, 20 years, it's like, okay, you know, here's Doug Leone and Moritz and, you know, here's, you know, John Doerr, here's Gurley. Like if we are making a Mount 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. The Berkshire Hathaway of the internet, if you'll recall. Indeed, indeed. 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. BerkshireNerds.store. BerkshireNerds.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, 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... Companies like 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

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%, 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 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. The VCs get their money back. Some or all the money back. And most importantly, get their time back, get off the board. Yeah.

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. Tiny is very good at figuring out structures that make sense. Yes, they're incentives masters. Yes, 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 retire. 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. Yeah. Like why retire? He was just awesome. But, you know, if you had that conversation right now about Mount Rushmore.

Like, you gotta... Okay, so... Who's on your mountain rest? 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 a number of startups, but there's a lot of big ones in there. You have big impacts. So Paul Graham's definitely in the running. But, okay, so do you go with... John Doerr. John Doerr's in there along with... So if you're doing firms, it's a lot easier because you get Koshla, Doerr, and...

Perkins, Tom Perkins. You get the three of them at once. You do Sequoia. People forget. Vinny Costola spent a decade at Kleiner Perkins with John Doerr. Yeah. So I mean you look at that firm. That's like the OKC with like James Harden, whatever. But then you have Doug, Leone, Mike Moritz, and Valentine. Jim Gatz.

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 definitely have to have the Sequoia and Kleiner. You got to have Bill Gurley. The Fab Four era of Benchmark. The Fab Four era of Benchmark was truly something special. It kind of builds itself, the Mount Rushmore right now, right? It's going to be Sequoia, Kleiner, Benchmark,

And then we're like, we're going to have a big debate on the fourth arm, right? 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? I mean, is it Angelus, Naval? Right. That's had a huge impact. Do you put YC in there? Do you put... YC or Techstars both have a huge impact. Do you put, you know,

Who else could be in there that's just... You could argue for Founders Fund. You can say YC and Techstars. Not yet. It's a completely different thing. YC is like... Yeah, for sure. Three orders of magnitude more significant. 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?

Oh, wow. That's high beta. Well, no, I mean, but... Maybe Founders Fund. Maybe Founders Fund. No Founders Fund yet. I don't know. Depending on... Excel would be in the running for sure. Ron Conway. I think the way you kind of have to define it, which is unfortunate because it means that it's going to be a long-ass time before your firm hits Mount Rushmore, is...

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?

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

is a very special building. It was the forethought PowerPoint. The Quadris Complex. Quadris Complex. Yeah. Office. Then it was Microsoft Silicon Valley. We're the only three people who want to shit about this. Oh, no. The three of us are so excited right now. This is the internet. We're like, wow. We've aggregated all the other people. Everybody else who cares about this is listening right now. And like Sebastian who wrote the parallel. Yeah, yeah, yeah. You guys are taking this way too seriously. It's not that important. We're like alone yelling in David's house about a fictional Hall of Fame.

TVI, Merrill Pickard. TVI. That's a good. August Capital. One on 20 at Microsoft. Benchmark Capital. Shasta Capital. All in this same building. And I think there's some space for rent in there.

I don't want to go live down there, but like, I think we got to take out a lease just to put the museum, the 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 like, we'll just, we'll do it like every year we induct somebody. We'll get up there, the three of us and be like, this year we're inducting into the Venture Capital Hall of Fame. We should totally do this. Kim O'Hara exists.

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, but it's not for capital allocators. It's not for people. Like, yeah, there should be a Hall of Fame. And do we, like, do we Midas-less style ask people for the real hard truth numbers? No, no, no. It's about impact. No, we decide. The three of us. We decide. It has to be impact on the game. Does the NVCA have, like, a Lifetime Achievement Award? Is that the closest thing there is? It doesn't really exist anymore. Yeah, no. It's about impact.

like the intent of the person. This is why like Paul Graham would be like, you know, first ballot. This is why. Yeah. Okay. Who are the first ballot entrants? 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? Wait,

Peter Thiel. This is what I'd say. If you're under 20 years, you're not... Let's wait until you're 25 years in. Yeah, just like the Sports Hall of Fame. You've got to have a... Yeah, you've got to be... You're not playing in the league anymore. So Paul Graham's still playing in the league. Does Jeff Bezos count as...

Well, 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. Oh, yeah, yeah. 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. You've got to put on, you know, when you're looking at it, I think you've got to look at impact. Yeah.

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, you know, he's Carmelo Anthony, right? Or Charles Barkley. He didn't win a ring, but... Okay, so then we got, like, Arthur Rock. You gotta look at, like, the founding father type. Of course, of course. Yeah, there's no doubt. I mean, that's like going back to Bob Cousy or whatever. Going back to, like, some really, like...

You know, people who built the league kind of situation before it became the league, right? So you got the league and you have the people before the league, you have people in the league. You've got generational shit right here. You know, Patrick Ewing. Because I think like you look at Gurley, like he's part of that Patrick Ewing generation, right? Like that Hakeem Olajuwon, Charles Barkley generation. You start talking about Founders Fund or YC or AngelList. Like, okay, now you're talking about more modern era. Still going, modern era, after 2000. But if you started before 2000, it's a different group.

Do you notice we haven't talked about Andreessen Horowitz in this conversation? Oh, god. Who cares? No, Impact on the Game, they're in. I'm just observing that. 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 adventure. 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 J.P. Morgan or a Goldman Sachs of Silicon Valley. Should there be? I don't know. Yeah. Why does Goldman Sachs manage the money of entrepreneurs? I just feel it's too... Okay, fine. But I just feel like it's...

It's too premeditated and less soulful. 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 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, you start comparing it to Sequoia or Benchmark. I think in the arc, it will not be comparable to Benchmark and Sequoia. And we, I mean, made a lot of hay of the fact that they had...

that they made $11 billion in profit on Coinbase. And like, I do not think they sold out of that. So they did not make $11 billion in profit as of today. Well, I mean, it's timing is everything. We'll see. I mean, it's interesting too. I mean, having just done this benchmark episode, like the,

Benchmark Fund 7, one of, if not the best institutional-sized fund of all time. Just unreal. 20 to 25x. But even that, 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. Yeah.

I like the Hall of Fame idea. It's kind of interesting. I think that actually would be a fun thing. We should get some space on Sand Hill and put up a... No, we could just do it as like a dinner. We just literally have... We don't need a space. Every year, we could just start in a restaurant, but you could get like a little hall and say, we're going to induct into the Venture Capital Hall of Fame the following people. And here they are. And we just have three pictures.

boom, boom, boom. And you just drop it. And it's like, here's our three people. And then people come up and say something about the person. And I think like you, we, we could do like the three who we would hope would be there. And then we'll have, we do it like the sports where you have the person who's being inducted chooses who inducts them. Sure. That's fun. Yeah. So Ruloff does Doug or whoever does Moritz. Yeah. Yeah. But John Parker does Moritz. Yeah.

Mike chooses who, you know. Yeah, no, he can have Larry and Sergey come up. He has Jason Calacanis come up and be like... No, no, he can have 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...

You do one in memoriam. Yes. You would do one in memoriam. So you do, you know, whatever. 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. Yeah, you do a combo. You do a combo. Maybe it's four people a year. 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 Hall of Fame. Right. There are people. That'd be a very Andreessen Horowitz way to do it.

That was, yeah, Andreessen was like, oh, what's the total assets under management? You know, and it's like, okay, dude, we get it. Nickelback sold a lot of albums. Yeah, they're the Nickelback of that. No, I didn't mean that. You said that, you said it. I wasn't talking about Andreessen. Oh, God. Oh, God. Oh, God. Like a million, 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 Conway, did Ron Conway, who had a bigger impact, Ron Conway or Andreessen? Like, I think it's a conversation. Hmm.

You know, because Ron Conway, when I came into the industry, like there was at one point, I was at the Crunchies and Ron Conway, at one point, like somebody said like, hey, can everybody stand up who said Ron Conway invest in their company? And 100 people stood up. And my mind was like, oh, whoa, angel investing is cool. I mean, I wasn't an angel investor at the time. I was-

long before I became a Scout. But I always remember that moment when like a hundred people stood up. That inspired. It was inception. Is that what gave you the... Is that what like put you in business as an angel investor? The Scout is what put me in business. What happened was I had... Was your Uber investment you personally or was that Sequoia's money? That was Sequoia's money. And we were like, Ruloff and I were trying to figure out like, do we let people know we're doing this or not? It was like a big controversy at the time. Like we want to keep this stealthy. I mean, Travis knew, but...

You know, it was a pretty great deal. You know, it was like, um... Wow. You know, at the time, they carried 50-50. 50-50 at the time, yeah. They dropped it down after that. Yeah, I bet. Every time I'd see Doug Leone, he's like, 50-50. 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, would always make a joke, would say, 50% carry. Oh, God, we get 30, you get 50. This is funny. Yeah.

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. Look at Elon. Yeah, exactly. So the human species getting moved forward by, as Steve Jobs would say in those commercials, this is the crazy ones. They do need fuel. They maybe don't have an idea of...

you know, if they should even build this company. And I think the capital allocators really come in and say, here's some fuel. You know, here, go fight that war, you know. It's fuel and it's belief, too. I mean, like, your story about Calm is not uncommon, I think, amongst founders. I mean, look at, I mean, the stories about Don Valentine and Atari and other places where he was at Cisco. He's like, so we got to get this thing back on the rails. This thing's going to zero. Yeah. You know, like, there's a lot of existential moments where things go to zero and, like,

So can I ask you, as we start to like drift toward the end of the episode here. That's your line. That's your favorite line. Drift. That's the Ben signature line. As we coalesce here toward the end of the episode. As our time together. Is this different enough from our normal show? Should we do this? Yeah, I think so. What should we change? Yeah, do you like this?

I think a casual glass of wine and just, you know, if you have friends of the pod and you want to go deep and talk about them in a more casual way, sure. Yeah. I mean, I think it's a great way to just have somebody on again, you know? So if you profile somebody like, I forgot that I had

you had done the first episode with me. And that was more about my career and more details. So I'm starting to tell stories over again. It's like, well, let's talk about some other stuff, right? Yeah, a bit. I think it's like a nice... It's a different context. Our audience was one-tenth the size at that point. I like this format. Well, part of what we... Lex has done so great with his show. 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 dark. It's not about that. 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 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 on Joe was in the running to replace Jackie Martling on the Howard Stern show people don't know this so really he was very enamored with Stern and He wanted to be Stern I think and he eventually has a planted. Yeah, the way he did becomes. Yeah, I did become Stern and so I

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...

Which this would actually bring it all the way full circle back to Charlie Rose. He was like a... I mean, he did more than business, but he would have... He did culture, business, anybody in New York. Because New York, everybody in New York was pretty fucking interesting. Yeah. 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...

you know, any actress on who was doing something interesting, any novelist, Margaret Atwood, anybody, which is coming through New York on a press tour, you know, you 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 like sort of more jazzy, you know, a little bit more like...

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. Arnett, and then somebody else. Yeah, the guy from Will & 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 Katy 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... No, no, that's not your right. You guys are not... You can't make... You got to know the person's background much better. But they all seem to know... Because the celebrities carry a certain charisma with them that our industry doesn't have. Yeah. But maybe it doesn't have to be the surprise as much as like... Yeah, that's true. Well, the other thing is that even though they have guests, the show is actually about them. The guest is a prop. Yeah.

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 very highly. I don't think so. Yeah, it's really weird that, like, Spotify doesn't allow Joe Rogan and Call Her Daddy on iTunes because...

the advertising would be huge right right so why not like bake the ads in and put them over there's some nba that's around the numbers that says it's more valuable if it's driving new subscribers i guess that's it i guess that's it yeah oh guess you know what they want to be able to have those new subscribers so when they go renegotiate with the yeah music so 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

It's getting so hot. For those of you who don't know, we're in like a sauna. A new, yeah, it's David's new house. David just moved. David's got a new empty house. 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 like two days. That explains the smell.

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. It's got to stop. I bought a temporary couch on Craigslist. It's the thrill of the... 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.

Ovanta.com slash. Ovanta.com slash acquired. Our thank you also, you don't know who the other sponsors are because we haven't, we didn't record them live with you because we like, we felt very strongly that it was, you know, we wanted to make better use of your time. 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. Brex? Maybe they have. I don't know. There's also a lot of ad-libbing in it. You're talking about Brex? Brex, yeah. I know a lot of people who use Brex. I think we use Brex. It is. I'm 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. 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 that. Oh, because it's in here, yeah. So anyway, thanks. Shout out Brax. So that's Brax. Shout out Brax. Use the promo code twist. We share this last sponsor.

these are these are great folks these are these are like dear friends and and geniuses and raconteurs masterworks no no no good guess think think smaller but bigger literally small but secretly huge tiny

Oh, tiny, of course. Yes, they're buying companies. They're doing a good job. Yes, they're creating the Berkshire of the internet. And can you imagine a better time to get the monkey off your back of venture capital and sell your company? Secure the bag. 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 a bag. You get that tiny bag. You get that AOL web blog. 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. I got, it's a funny story. I'm in my office and I got Bank of America and I got like,

Low thousands of dollars in my bank account. I got an American Express card with 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, 7? I'm hitting refresh. I'm hitting refresh.

And then bink, bink, bink, bink, bink. You know, 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 he owned 10%. I think he owned 10%. Anyway, long story short, my wife comes in. She said, you OK? And I said, what? She said, yeah.

"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." 'Cause I spent my whole life worrying about money. My dad had lost the business and everything. It was a very cathartic thing for me. And I think people who are already rich 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 piece.

It's a tiny bag, but it's filled with diamonds and cash. You just open it up and say, thank you, Tiny. Thank you, Tiny, for securing the bag. Acquire.fm slash Tiny. No, it's literally, they don't give us a thing. Is it Hyatt Tiny? Whatever it is, just know that Tiny will help you secure the bag. You can mention Jason. I did buy a OneTouch Express machine. I bought a Jorah

one touch espresso machine which at the time was like two grand and i was like this is unbelievable that i tried to buy a ferrari ah they wouldn't sell it to me in beverly hills you were like no new money or something what's yeah basically i went in there and they're like oh yeah what am i like to buy a ferrari uh today the 430 and they're like oh we don't have any available and i was like okay can i put myself on the waitlist we're not taking names from the waitlist

So I said to this guy, can I ask, what do you do here? He's like, we sell Ferraris. I'm like, to who? 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 build these teams. 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, okay. I was like, I'm a cash buyer. He's like, everybody's a cash buyer. I'm like, okay. Um...

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 a 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,

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 certified 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... You're like, the sticker says $300,000. I was like, no, no, no. This is a potential... I said, did they use one I was looking at? He's like, yeah, you can't get these cars. And I was like...

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 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 a 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 that turn the page was Corvette C6 was the number two car and the starting line was make Ferrari or buy two for half the price of a Ferrari and Beat them off the line Let's go to the Chevy store. There's Corvettes everywhere. Yeah, he goes you want to buy a car? I said, yeah

He said, if you buy a Corvette today, I'll give you $5,000 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, OK. And I punch it to 100 miles per hour. The guy's like, yeah. How does that feel? I'm like, great. We go back. 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 American. And that was the car that I famously was, according to Gawker, Robert Scobel, myself and Elon. When Elon got the first P1 of the Roadster, he was like, I got it. I was like, oh, let's meet in Brentwood. And we were driving them at a...

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 then we switched cars. And I was like, nope, electric is going to beat everything. And this was the first one.

That, 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 because we were just before the iPhone, you realize. Like Robert Scobo was recording this on his Nokia, you know, smartphone. Dude, these are the memories, right? Like 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. 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 career experience. Acquire.fm slash Craigslist. 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 get some sushi or Mexican. I don't know what we're going for here. That was awesome. So fun. Thank you so much. Of course.

All right, listeners, we hope you enjoyed that very first Acquired Sessions with Jason Calacanis. It's a new format we're playing with. We would love your thoughts. AcquiredFM at gmail.com or tweet at us at AcquiredFM. I...

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