ACQ Sessions: Jason Calacanis

Speaker 1 Wait, it would have magazine.

Speaker 1 Magazine, yeah. That's how I started, yeah.

Speaker 1 Magazines was like the original platform for

Speaker 1 have we started?

Speaker 2 Silicon Alley. I guess we started.

Speaker 1 This is the trick. We've just been reading the ball.
We just started the whole time. Yeah, but welcome to quiet sessions.

Speaker 2 All that stuff that you said beforehand that is really juicy. I don't think we should put that in.

Speaker 1 No, definitely not. Definitely not.
We don't want to tell people where the bodies are buried. Well, cheers, boys.
Cheers. Here we go.

Speaker 1 Is this the first one?

Speaker 1 This is the first in real life.

Speaker 1 I think this is our ninth, tenth together, something like that. A lot.
Between the two pods, yeah, for sure. Great to know you, boys.

Speaker 2 So this is the first Acquired Sessions.

Speaker 1 Acquired Sessions. I feel like I should get out of a guitar here and just play some Dylan.

Speaker 2 This is your baby. What is Acquired Sessions?

Speaker 1 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.

Speaker 1 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.

Speaker 2 David Rosenthal unplugged.

Speaker 1 Wow. Love it.

Speaker 1 This is the literally MTV unplugged. Literally.

Speaker 2 Okay, listeners, now is a great time to introduce a new friend of the show who many of you will be familiar with, Claude.

Speaker 2 Claude is an AI assistant built by Anthropic, and it's quickly become an essential tool for us in creating, acquired, and the go-to AI for millions of people and businesses around the world.

Speaker 1 Yep. We're excited to be partnering with them because Claude represents exactly the kind of step change technology that we love covering here at Acquired.

Speaker 1 It's a powerful tool that fundamentally changes how people work. I know, Ben, you have used Claude for some acquired work recently.

Speaker 2 Yes. So listeners, I used to take four plus hours.
the day before recording to take all the dates for my raw notes and put them in a table at the top of my script for recording day.

Speaker 2 On the Rolex episode, I actually fed my raw notes into Claude and asked it if it could do that for me, which was amazing.

Speaker 2 I just got my most important 100 dates for the episode done in like 20 seconds.

Speaker 1 You texted me this table. It was awesome.

Speaker 2 Yeah, that freed up an extra half day that I used instead to focus on explaining how a mechanical watch works, which I'm so glad I got to spend the time doing that instead of making the table.

Speaker 1 Totally. So cool.
I was actually just chatting with Claude to brainstorm ideas for something big that you and I are working on for later this summer, and it was insanely helpful.

Speaker 1 Listeners, stay tuned to hear all about that.

Speaker 2 Yes. So listeners, by using Claude as your personal or business AI assistant, you'll be in great company.

Speaker 2 Organizations like Salesforce, Figma, GitLab, Intercom, and Coinbase all use Claude in their products.

Speaker 2 So whether you are brainstorming alone or you're building with a team of thousands, Claude is here to help.

Speaker 1 And if you, your company, or your portfolio companies want to use Claude, head on over to claude.com. That's C-L-A-U-D-E E dot com or click the link in the show notes.

Speaker 1 So, in the juicy stuff earlier, you mentioned mahalo. Yeah, I don't know, is that why you started

Speaker 2 like referring to the juicy stuff as yeah, the juicy thing?

Speaker 1 Yeah, no, we want to talk about that stuff. Yeah, yeah, yeah,

Speaker 1 is mahalo why you started you went from print to print to well when I in the 90s, um, you know, I grew up in Brooklyn. Um,

Speaker 1 my

Speaker 1 dad

Speaker 1 had his bar uh seized by the feds because he didn't pay his taxes during the 1987 crash.

Speaker 1 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.

Speaker 1 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.

Speaker 1 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.

Speaker 1 And I worked fixing laser printers. And that was like a really good racket.
The HP had just come out.

Speaker 1 Were you set to go to college somewhere else?

Speaker 1 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...

Speaker 1 went into the force and then I said, you know what? I'm going to see if I can go to college and make that work. So I'm going to go to Brooklyn College.

Speaker 1 So I decided to work during the day, and then I went to school four nights a week, 6 to 9 p.m., carried full credits, 16 credits a semester. And I would work fixing laser printers all day.

Speaker 1 I was a bad student. I was always that student who underperformed.

Speaker 1 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 and my PC Jr.

Speaker 1 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.

Speaker 1 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.

Speaker 1 And he had one of the first Pongs in Brooklyn in his bar.

Speaker 1 He must have cleaned up on that. Oh my God, it was crazy.

Speaker 1 And so we, I just got exposure to video games and computers, and I was like, wow, this is incredible. Like, computers are going to change everything.
And then I happened to hack some software.

Speaker 1 We used to, I ran a lot of scams, but

Speaker 1 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

Speaker 1 we would make copies of like Chess Master and stuff like that and then sell them for 10 bucks. And then we started like hacking and doing what was called phone freaking.

Speaker 2 When you were doing this stuff, like,

Speaker 2 you had to be reasonably technical to do it. Not like the, you know, not like Wozniak technical, but like

Speaker 1 we solder chips sometimes. We changed.

Speaker 1 Like we put, to put memory in at that time, you had to like take the memory chips and put them in and then bend them over and stick them in.

Speaker 2 Did you ever think about, like, did you consciously ever make a fork where you were like, not tech media?

Speaker 2 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.

Speaker 1 It's a very good question.

Speaker 1 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

Speaker 1 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.

Speaker 1 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.

Speaker 1 I was like, I'm going to be a magazine publisher. So the first one I did was Cyber Surfer, which was about

Speaker 1 dial-up services and CD-ROMs. And I did it with my friend Brian Alvey, whom you might have heard of in my career.
We went to high school together. Weblogs? We did weblogs together.
Yeah.

Speaker 1 So, but in the early 90s, I did

Speaker 2 Screen Gadget, Twad.

Speaker 1 All that stuff. Yeah, which is a lot of people.
Which everything you sold to AOL. I think I sold to AOL.
But anyway, before that,

Speaker 1 I did that magazine. And then I had

Speaker 1 I met Jerry Kelowna at Internet World, the first one. And there was a booth.

Speaker 2 That's right, when Jerry was a VC before he was like the

Speaker 1 VC, he was consulting for Lycos and I think CMGI.

Speaker 1 And so there was a Lycos booth, and I had met this young lady at it, and we hit it off, and we were talking, and then she introduced me to Jerry Klona.

Speaker 1 And then I met Jerry Klona in an office no bigger than this room in Union Square. And he said, Listen, I'm leaving Lycos, but I'm going to start this Acme Ventures with my friend Fred.

Speaker 1 I want you to come read business plans for us. And so I met Fred Wilson, and I would go up to them, and they were doing JP Morgan, it was going to back them for their venture firm.
This was 1994, 95.

Speaker 1 This became Flatiron. And it became Flatiron.

Speaker 2 JP Morgan was the first big anchor of Flatiron.

Speaker 1 They were half of it, and Masayoshi-san, SoftBank, was the other half. No way.
So they wanted you to come be a VC associate. Not a VC, just to read business plans.

Speaker 1 So the deal was they would take me for sushi and pay me $1,000. Wait, what do VC

Speaker 2 do besides just read business plans? Exactly.

Speaker 1 Well, anyway, it was the thing. And so I had the magazine started at Silicon Eye Reporter, and they were paying me.
And so I read about this

Speaker 1 Beverly Hills internet company, which got rebranded as GeoCities. And I wrote a little coverage of it, and I said, you shouldn't invest.
I'm 24 years old. I don't even know what VC is.

Speaker 1 That's where Flatiron made all their money. Yeah, they were going to invest anyway.
Flatiron became USV, right? Yeah,

Speaker 1 Flatiron went with Jerry Kelowna. Then, when Jerry decided he wanted to move to Colorado and just chill,

Speaker 1 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.

Speaker 1 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.

Speaker 1 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

Speaker 1 Fred said to me, listen, you're doing Silicon Eye Reporter. You're writing about us and the companies we're investing in.
And

Speaker 1 you're doing stuff. Which would you rather do? And I was like, I think I'll do the magazine.

Speaker 1 This was before. Now it's like

Speaker 1 I do both. Why choose? But just to back up to Teo Cities, that sold to Yahoo for like $300.
$5 billion. And

Speaker 1 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 New York, VC, and Jerry.
They did pretty well.

Speaker 1 nothing. How did that happen, right? Like, I mean, Silicon Valley was here, but they're in New York.
Like, what was going on?

Speaker 1 Yeah, we just, there were a lot of good companies brewing in New York, and my concept with Silicon Valley Reporter was, well, they have Red Herring

Speaker 1 upside in the bay, but I own New York, and I had Silicon Valley Reporter, and then I started one called Digital Coast Reporter in LA. So I had two magazines, two conferences, two email newsletters.

Speaker 1 I was kind of king of New York, right? I grew that business to $10 million in revenue off my credit cards

Speaker 1 and

Speaker 1 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 anselves. I taught myself everything.
What did your family think of this?

Speaker 1 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 of me about me for 8,000 words in the New Yorker.

Speaker 1 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.

Speaker 1 And I was in publishing, but I was also in this new thing, technology.

Speaker 1 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

Speaker 2 can I so we talked all about a lot of this when we did our like big Jason Cal like Empire of Jason Calicanus episode with you so I want to like put this on pause so sure people can go listen to that you should it's great we get like the detailed story of like web blogs inc and all that great stuff and you mentioned i want to like take us from you're probably as good as the you know your greatest your newest thing sure um because the last time we talked to you you were just starting all in hilarious and like can we talk podcasting of course i love it podcasting is like i think perhaps my greatest medium what happened with all in how did

Speaker 2 i i mean it's weird

Speaker 1 has it surpassed your wildest expectations um i thought it would be something chamath and i would do 10 times. Yeah.
So the origin story is pretty simple.

Speaker 1 Chamath,

Speaker 1 I knew because he was running ICQ.

Speaker 2 Chamath was running ICQ?

Speaker 1 At AOL, and I had sold my company to AOL and like the revolving door of AOL.

Speaker 1 There was like Ted Leonces had this march to a billion.

Speaker 1 My Greek brother, a mentor, had this like march to a billion.

Speaker 1 off-site. And so I went to this and I just sold Weblogs.
Like a million AOL users.

Speaker 2 Hot shit. That's the idea.

Speaker 1 That was the idea.

Speaker 1 Well, with Web Logs Inc.

Speaker 1 and with AOL and other assets they wanted to buy, they were going to march to a billion users. It was like this crazy rallying cry, and we had these t-shirts march to a billion.

Speaker 1 So I go to that and I see Chamoff and I was like, hey, and he's like, hey, and we introduced each other and we had known of each other. And I was like, what are you doing here?

Speaker 1 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. I said, it's hilarious.
And he's like, yeah, but I'm anything. I'm going to go.

Speaker 1 I'm going to go to the West Coast. I'm going to go work at this VC or whatever i was like all right nice seeing you um and so then when he was there i was in la

Speaker 2 uh and what vc did he go work because he was at face

Speaker 1 mayfield for a year and then sean parker introduced him to uh um zuck and zuck needed you know like a chamath he needed like somebody who would just

Speaker 1 chamoth be a

Speaker 1 growth team he built the growth team and he's like i don't There is no equivalent of growth. That was the idea of growth hacking didn't exist as a term until Chamath did what he did.

Speaker 1 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 because he, too, was very hungry.

Speaker 1 But you guys must have been like brothers from another beach. Yeah, for sure, for sure.

Speaker 1 We're definitely both outsiders in Silicon Valley. And,

Speaker 1 you know, I had Chamoff come on the pod this week in Startups, that is. We listened to it.
It's fun to go. It's hilarious because that's all the first time.
And, you know, you can see how he's not

Speaker 1 polished. He's not Chamoth,

Speaker 1 gregarious or whatever. He's a little more of a pair of people.
He doesn't have the Lauro on. No Laura Pian.
He was a little bit more. Was he in great shape?

Speaker 1 No.

Speaker 1 Not what I was taking short.

Speaker 1 He was like a dork, you know, like he, but he was.

Speaker 1 He was Bezos pre. No, he was like Bezos pre.
Yeah, whatever. But, you know, he always was a poker player.
He was playing Atlantic City.

Speaker 1 So he was, you know, like myself, an outsider who wanted to take risk and wanted to win. And,

Speaker 1 you know, confident, you know, even maybe more confident than both of us should be.

Speaker 1 And so I kind of introduced Shamath to the world by convincing him to come on the pod, which he was like reluctant to do when he was at Facebook, but he did it after Facebook.

Speaker 1 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.
He's funny or whatever. And so.

Speaker 2 Which at this point you had an eye for, because you really, of course.

Speaker 1 I mean, one of the things when I was a podcaster in those early days, you know, talking about 12 years ago, whatever, is, you know, I introduced a lot of people to the world.

Speaker 1 Introduced people to the world.

Speaker 2 Yeah.

Speaker 1 Yeah, it was 2008, I guess, whatever. So I introduced a lot of people who were in tech to the,

Speaker 1 you know, and it was only a couple thousand people. And then as now, too, like,

Speaker 1 you could be a great founder. You could be a great, you know, person in tech, but like, that doesn't automatically make you a compelling podcast.

Speaker 1 As we know. No, of course not.
No, I mean,

Speaker 1 I have my own theories about what makes for a great guest, but we'll put that on the side for now. But anyway, we start a friendship.
We start playing cards together.

Speaker 1 We start hanging out, you know, trading notes kind of thing. And he's going to start his venture firm.
I'm a scout at Sequoia, all that stuff.

Speaker 1 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...

Speaker 1 We have such a good rapport when you interview me because he had done a bunch of interviews with me on stage and stuff like that on my events. He's like, I want to do a podcast for the.

Speaker 1 I was like, yeah, you can come on the Swing Star Ups anytime. It's twice a week now.

Speaker 2 Which it's now five times

Speaker 1 Sunday. Plus, I'll see.
I'm gonna go, I may go back down to five next year. It's a little much right now.

Speaker 1 Yeah, dude, you're, I mean, we'll come back to this, but you're killing yourself right now, and you're on act three.

Speaker 1 Yeah, I have more energy now than

Speaker 1 I may, I may have, I, I, just this, like, coming out of the pandemic, might have as much energy as I did when I was in my 20s, but for different reasons, different type of energy.

Speaker 1 Um, anyway, Trimoff calls me, you know, coming out of the studio.

Speaker 1 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 pod with you.

Speaker 1 I said, okay and he said well 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 when texting back and forth I was like we should call it all in 2020 yeah it's like two years ago whatever and I said yeah we should call it all in like we should come with a poker name he's like yeah great like a raise or something it's like all in because you would you'd been referring to this poker game on air on Twitter yeah I would talk about it once in a while the poker game that doesn't exist and Sky Dayton and I had a poker game with Brooke Hammerling the famous PR person at the code conference which was the all things D conference before that for 20 years.

Speaker 1 Then Chamoth had had a poker game, Sachs, I had hosted it, floating,

Speaker 1 and putting all that together.

Speaker 1 Yeah, I'd refer to it many times on the pod, but tried to, you know, keep it from becoming public. Right.
But it was me, Bill Gurley. It's all public now.
Mark Pinkus, right? Or maybe Pinky.

Speaker 1 Pinkus used to come to the Code one. Yeah.

Speaker 1 Which is another funny story.

Speaker 1 And lots of funny stories in my life. But anyway, so then the pandemic happens and we're like, well, where are you going just dropping these little fred curves we got to pick them up on the

Speaker 1 point we got to pick these up anyway at some point i'll write a biography anyway um

Speaker 1 nine years uh third book anyway the um

Speaker 1 then we we were the pandemic starts to happen like well sax has some ideas about masks and then freebergs and freeberg weren't there was no besties originally right now it was just you and i mean in truth like uh freeberg and i weren't besties before all in i mean we knew each other.

Speaker 1 We were friends, but not besties. I was besties with Sax and Shamath.
And now Freeberg is a bestie.

Speaker 1 But he played in the game, obviously, and we had just started to have a developer friendship. But anyway, that force him kind of clicked, right, pretty quickly.

Speaker 1 And I think...

Speaker 1 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.

Speaker 1 And I had had Sax on many times and Shamath. So I was very comfortable with that.
I mean, at the poker game, we break chops and I make jokes.

Speaker 1 And Shamath's a great host. And we're just very comfortable with each other.

Speaker 1 And Freeberg kind of joined that group. And

Speaker 1 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.

Speaker 2 And I realized like in perspective. I mean, I think that's a thing.

Speaker 2 I'll tell you, I never expected to be listening to David Sachs talk, coming from where he comes from politically and where I come from politically, and going,

Speaker 2 that is a good point. And that perspective is

Speaker 1 so helpful in our polarized world today. Yeah,

Speaker 1 it's very unique. And, you know, around the poker table, we all listen to each other and we're friends, but the world does not want us to be friends in some ways.
The world wants us to be enemies.

Speaker 1 And I kind of think about it like

Speaker 1 best of enemies kind of situation. Like we debate specific things, like Gourvadal and

Speaker 1 who is his adversary. Anyway, it's a great documentary about Gourvadal and

Speaker 1 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.

Speaker 1 They started debating different political conventions, and it was like the most compelling thing on TV.

Speaker 1 But they were like friends.

Speaker 1 Best of enemies.

Speaker 1 They were besties, like Saxon I are, but you know, Gourvadal was just, he was gay,

Speaker 1 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.

Speaker 1 Like, at one point, Buckley, I think he called him like a sissy or something like

Speaker 1 really like derogatory as a gay man. And the world didn't understand he was exactly gay.

Speaker 1 It was like sort of time period in the 60s where like maybe some adults understood like, yeah, that's a gay man, but we don't say that's a good idea.

Speaker 1 When Ben got into town yesterday, we were driving the castros right nearby and we saw a naked guy in the castro and i was like oh naked guy in the castro and ben was like what is going to be like dude you got on the unity in the camera

Speaker 2 like huge jacked dude walking around and and super sunny so he's like just all like slick down

Speaker 1 but did he have his shoes on was he wearing combat boots they usually wear boots yeah and then they usually carry a sarong there was a big debate when i first moved up here because there was a number of folks who used to like to get a Starbucks and they had to like negotiate.

Speaker 1 And they were like, how about a sarong and Starbucks? Because you're going to sit.

Speaker 1 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

Speaker 1 now it's like you see it's like ah this is like a relic of the 60s 70s yeah and actually it was pretty awesome because david we're like driving up and david goes oh a naked guy it was the most like warm-hearted yeah i had to um yeah adjust as well as a new yorker because as a new yorker if somebody's naked that's a sign that if there's about to be some crazy person in a fight and police and chaos.

Speaker 1 And here it means like high fives and right ons.

Speaker 1 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

Speaker 1 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.

Speaker 1 That's one of the things I love about San Francisco. But anyway, the pod's gotten very big.

Speaker 2 So you get the gang together and like,

Speaker 1 why do you think it works?

Speaker 2 Like, is it

Speaker 2 works? It's like the number one-ish technology.

Speaker 1 Well, in our business, it's number one, of course, but it was number 28 last week. Like, in the world on IG.
You guys have transcended. Like, this is more.
It has nothing to do with tech anymore.

Speaker 1 It has nothing to do with finance or tech anymore. It is

Speaker 1 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.

Speaker 1 I was like, hey, I hate to be a pest, but I see you're wrapping up.

Speaker 1 And no pressure, but are you going to be leaving soon?

Speaker 2 Because I'd love to camp out here and get your time. And they're like, stop busting my pencil.

Speaker 1 And the woman looked at me and she goes, Jay Cal. 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.

Speaker 1 And I was like, oh my God, that's so nice. She's like, I was like, are you in the industry? She's like, I'm a dentist.

Speaker 1 What?

Speaker 1 Reno. And I'm like, you're a dentist in Reno.
Can I ask how you found out about it? She's like, I don't know.

Speaker 2 It's like, I deeply care about San Francisco politics.

Speaker 1 No. Somehow she had found it.
And this is, you know, during the pandemic situation. And then that's when I realized it had crossed over.

Speaker 1 Was there a moment for you,

Speaker 1 either either you four or you, where you were like, whoa, this is

Speaker 1 you know, I've been

Speaker 1 micro famous, you know, micro celebrity multiple times in my career. But this is New York.

Speaker 1 Yeah, not for me, you know, and I got a lot of famous friends.

Speaker 1 You know, I'm used to getting recognized. I'm used to people taking pictures.

Speaker 1 What I'll say is like where it used to be, you know, if I go to Austin or New York, people would say, I would have three people stop me on the street a day if I was walking around in New York.

Speaker 1 Now it's 20, you know, or 10 and they want to take a selfie and it's, you know, just, you know how podcasting is, you guys get recognized and it creates a level of intimacy with people

Speaker 1 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

Speaker 1 a show or in all honesty, I did craft. With all in, I was very premeditated in creating some character.
I've never really talked about this. Yeah, yeah, yeah.

Speaker 1 I crafted some character kind of arcs.

Speaker 1 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,

Speaker 1 kind of

Speaker 1 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.

Speaker 1 Well, there's zero followers.

Speaker 2 There's even a character of J Cal on All In.

Speaker 1 J. Cal the world's greatest moderator.
Sure. Yeah.

Speaker 2 I think more like JCL, the guy who lets himself be the punching bag because it plays for the show.

Speaker 1 A little bit.

Speaker 1 Which rather, no, if I'm being honest, I'd rather not be the punching bag. Like, they're like, you're the poorest guy on the show.
I'm like, do we need to point that out so often? You're like,

Speaker 1 not by much.

Speaker 1 Like, I'm feeling really good about myself. You don't have to point out that you all have more money than me and you.
Two of you have planes and I don't. And it's okay with me.

Speaker 1 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.

Speaker 2 But you do let yourself play that role of like, like you have been enormously successful and you sort of let the role of JKow on the show be like that guy who one day wants to be like us, maybe he'll, maybe he'll make it.

Speaker 1 I actually

Speaker 1 never wanted to play that actually. No, that was not, that was just the boys breaking my chops, maybe.

Speaker 1 So maybe it's a little bit of like them wanting to, you know, maybe take the piss out of 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

Speaker 1 you can ask them when they're on the pod i think for them that's kind of the diss

Speaker 1 that's the one they can easily go to is i'm the poorest guy on the show but like i've done okay like what uh maybe let's flip it like for them before all in I mean, maybe Tamant had a little bit of a public discussion.

Speaker 1 No, they were not famous. No, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, they're all, this is a new thing for each of them to hit this level of notoriety.

Speaker 1 It's not for me. What do you think for, I mean, we should ask them this.
Sure. Like, if you were to speculate,

Speaker 1 caveat that it's speculation. What do you think for them, All-In has, like,

Speaker 1 done?

Speaker 1 Well, I mean, for Friedberg,

Speaker 1 nobody knew who he was except if you worked at Google or you were in VC. Like, he's very connected in

Speaker 1 those circles.

Speaker 2 What's that? Or Monsanto.

Speaker 1 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 desire to.

Speaker 1 So I think it's probably the biggest adjustment for him.

Speaker 1 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 Olin Summit,

Speaker 1 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?

Speaker 1 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.

Speaker 1 Right. So I'd be like, all right, I'll put Brad Kirstner 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.

Speaker 1 You know, and it was always like, I wonder if Freebread will show up. But he's actually really committed to the show now.
For Saks, he was high profile, but nobody really knew him as a Republican.

Speaker 1 So he kind of uncloaked as a Republican on the show. Well, I feel like he was also like, he was

Speaker 1 almost even more so than any, you know, well, not you, but he was high profile if you knew about the PayPal Mafia Monday. But he was like the least kind of public of the PayPal PayPal Mafia.

Speaker 1 Of the PayPal Mafia, you would say Elon Reed Hoffman, Peter T.L.,

Speaker 1 Max Levchin, Jeremy Stoppelman, Chad Hurley, Ruloff. Yeah.
And I guess Sachs would be somewhere in that strata of like being known. But I feel like being known.
Being known. Yeah.
Being known.

Speaker 1 But yeah, you know, and I think part of the reason this works is Sachs, I think Sachs has probably taken the brunt of the head of the pod

Speaker 1 because he is so passionate about, you know, a lot of topics that maybe are unpopular in the tech circles. So I do think it's cost him deal flow on the margins, probably.
I think there's probably.

Speaker 2 I don't really margin.

Speaker 1 I wonder. I wonder if

Speaker 1 he said that jokingly on the show. I don't know.
I'm just thinking like maybe there's some of that.

Speaker 2 Kraft has ascended because he's done all in in a way that's yeah, sure.

Speaker 1 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 Chill's venture firm?

Speaker 1 because I'm so liberal? For sure there are. And

Speaker 2 those people feel that way about Kraft now, but for every one of those, there's 10 more.

Speaker 1 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 yield flow. I don't know if it has.
I think surely the benefit of the...

Speaker 1 The pod too,

Speaker 1 I think for people, for people in America and people in tech, has moved, I think, a lot of people towards the center.

Speaker 1 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.

Speaker 1 You 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.

Speaker 1 But mostly that's a function of the fact that I've lived only in New York and California my life, where you don't really get many Republicans or moderates, but I voted for Bloomberg, Giuliani, when Verre was crazy, and Pataki, who are all Republicans.

Speaker 1 Were you here to the same sportsman or were you still here? No, I wasn't, but I would have voted for him.

Speaker 1 I like competent people, and I supported Bloomberg for president, which got me a lot of flack. Really?

Speaker 1 I don't understand why.

Speaker 1 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?

Speaker 1 What we all think we are here in Silicon Valley, which is like social, uh, liberal, fiscal, conservative. Yeah, we're like, everybody should be that, but we're the smallest of the four groups.

Speaker 1 Yes, it is a small group. I, I, um,

Speaker 1 I think I believe in competence and staying out of people's lives. So I, you know, it's very hard to know.

Speaker 1 Because then, even David, I mean, this is, I think, when David and I fight on the pod, which some people love.

Speaker 1 And I think some people probably turn the pod off when that happens and they don't like it.

Speaker 1 And certainly, the MAGA group has no love lost for Jake Al, I can tell you that. Like, my replies have been really crazy.
I mean, get like brigaded the last couple weeks.

Speaker 1 Nuts.

Speaker 1 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.

Speaker 1 A handful of times it's happened.

Speaker 1 But,

Speaker 1 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.

Speaker 1 And by the way, you're pro-choice,

Speaker 1 pro-gay marriage. Anti-war.

Speaker 1 Yeah, he's the dove. And I was like, well, okay, if you if we want to play this game, I'm going to dub you David the Dove.
And now you're taking me into Jason the Hawk.

Speaker 1 Like, what are we talking about here?

Speaker 1 But anyway, you know.

Speaker 2 It just goes to show how silly the coalition building is.

Speaker 1 It's totally silly, exactly.

Speaker 2 The two-party system requires that if you feel very strongly about something, then you're not allowed to think independently about anything else.

Speaker 1 It's so crazy.

Speaker 1 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 business being in any political office, and

Speaker 1 is just horrible on any number of levels. But I believe that independent of his party, he's a Democrat, obviously.
Obviously, yeah. Yeah, and so like I would hate him as a Democrat or a Republican.

Speaker 1 So it's not personal, and I would love to. Or it is personal with him, but it's very personal with the party.
Yeah, I mean, I just think this is a just horrible human being

Speaker 1 in every way. Now, I understand for some people,

Speaker 1 he represents change. For some people, it's like the way the Republicans secured office, and that's all they care about is winning.
I get it, whatever.

Speaker 2 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,

Speaker 2 we get to agree on something so that we all can find togetherness in something. And for some people, that's the flat earth.
And for other people, that's startups. And for some people, it's...

Speaker 1 It's the tribe.

Speaker 1 A lot of people don't practice religion anymore. And so he's their religion.
And Hillary Clinton or Elizabeth Warren, or Bernie Sanders might be other religions.

Speaker 2 Or the new iPhone. Like, I found myself ordering this phone, and I love it, and it's the i414 Pro, and it's magic, and whatever.

Speaker 2 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.

Speaker 2 And, like, let me look at the image quality versus the old one.

Speaker 1 It really is pretty.

Speaker 2 It is pretty, but, like, I got to be part of a tribe. And, like, that is a thing that no matter what your tribe is, that is so fun to be there on tribe day and tribe week.

Speaker 1 week. I will say the thing I'm proud about the show, I think, is that it has,

Speaker 1 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.

Speaker 1 When I say we, including you guys, but also specifically the besties,

Speaker 1 I want to be friends with people who I disagree with. I want to...
debate stuff, right? And then people are, like this guy, Dean Preston, and he's like one of these supervisors here.

Speaker 1 He's a super idiot, like guy in San Francisco who like,

Speaker 1 you know, like won't let them build housing and all this 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.

Speaker 1 He's like, you're a conservative billionaire. I'm like, wrong on both accounts, but thank you for the latter.
My besties remind me on the latter. I'm working on it.

Speaker 1 Not trying to be a billionaire. Thank you.

Speaker 2 Now is a great time to thank good friend of the show, ServiceNow.

Speaker 2 We have talked, listeners, about ServiceNow's amazing amazing origin story and how they've been one of the best performing companies the last decade.

Speaker 2 But we've gotten some questions from listeners about what ServiceNow actually does.

Speaker 1 So today, we are going to answer that question.

Speaker 1 Well, to start, a phrase that has been used often here recently in the press is that ServiceNow is the quote-unquote AI operating system for the enterprise.

Speaker 1 But to make that more concrete, ServiceNow started 22 years ago focused simply on automation. They turned physical paperwork into software workflows, initially for the I.T.

Speaker 1 department within enterprises. That was it.
And over time, they built on this platform, going to more powerful and complex tasks. They were expanding from serving just I.T.

Speaker 1 to other departments like HR, finance, customer service, field operations, and more.

Speaker 1 And in the process, over the last two decades, ServiceNow has laid all the tedious groundwork necessary to connect every corner of the the enterprise and enable automation to happen.

Speaker 2 So when AI arrived, well, AI kind of just by definition is massively sophisticated task automation.

Speaker 2 And who had already built the platform and the connective tissue within enterprises to enable that automation? ServiceNow. So to answer the question, what does ServiceNow do today?

Speaker 2 We mean it when they say they connect and power every department. IT and HR use it to manage people, devices, software licenses across the company.

Speaker 2 Customer service uses ServiceNow for things like detecting payment failures and routing to the right team or process internally to solve it.

Speaker 2 Or the supply chain org uses it for capacity planning, integrating with data and plans from other departments to ensure that everybody's on the same page.

Speaker 2 No more swivel chairing between apps to enter the same data multiple times in different places.

Speaker 2 And just recently, ServiceNow launched AI Agents so that anyone working in any job can spin up an AI agent to handle the tedious stuff, freeing up humans for bigger picture work.

Speaker 1 ServiceNow was named to Fortune's World's Most Admired Companies list last year and Fast Company's Best Workplace for Innovators last year. And it's because of this vision.

Speaker 1 If you want to take advantage of the scale and speed of ServiceNow in every corner of your business, go to servicenow.com/slash acquired and just tell them that Ben and David sent you.

Speaker 2 Thanks, ServiceNow.

Speaker 1 Another thing that's really fascinating to me about All In and you guys is

Speaker 1 before All In, and maybe it's still to a large extent, I feel like Silicon Valley has this weird relationship with money, like super weird relationship with money.

Speaker 1 Like, you know, remember there's a whole thing about like Zuck drove like an Acura SB. Oh, yeah, that all came from David Philo and

Speaker 1 David Philo and Jerry Yang were driving their old cars towards the world.

Speaker 1 Like the cool thing, like, you, you could, like, make money, build a company, but, like, you never want to, like, you never be understanded. You guys, I think, are the first, like,

Speaker 1 like, you're, you guys, like, whatever. Like, we got a private jet.
Like, that's fine. Like, you know, I mean, listen, I, I, uh,

Speaker 1 uh, you know,

Speaker 1 I believe in capitalism. I think it's great if people create jobs and if they get rewards for doing so, like,

Speaker 1 fine. I'm literally the book I'm writing, 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.

Speaker 1 So, I'm like, literally been thinking about this topic a ton. And I think we worry a little bit too much about wealth creation

Speaker 1 with like a small like outlier wealth creation and we don't think enough about inspiring people to create companies and learn and like

Speaker 1 the time I create the most controversies when I'm like I believe anybody can do it and people are like you're so wrong and I'm like

Speaker 1 am I because I go on YouTube and you could type in any topic that you want to learn and you can learn it.

Speaker 1 And all the stuff that was at MIT where I never got to go in Stanford and Brown is online for free. And I listen to macroeconomic classes and AI classes.

Speaker 1 When I'm like, it's 10 o'clock at night and I'm doing my email, I'll just put one of those playlists on from MIT Open Courseware.

Speaker 1 And I'm like, I can't believe I can take a course at MIT for free anytime I want. And then you, you know, flip it, you can build a business there.

Speaker 1 Like David Senra over at the Founders Podcast, like Mr. Beast, MKBHD.
Like,

Speaker 1 nobody gave these guys permission.

Speaker 1 Yeah.

Speaker 1 But people want to spread a narrative that the world is unfair.

Speaker 1 And like I watched, oh, I think the world becomes so fair and so just and so much information and opportunity become available that I'm like, wait a second.

Speaker 1 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.

Speaker 2 The world is still unfair. I think, very.

Speaker 1 I think the

Speaker 2 key insight is like recognize that the world is unfair.

Speaker 1 And actually actually what that is is a game on the field and figure out how to play the game on the field but I mean it's never been more fair so the world is unfair true statement and in America it's never been more fair you can learn Google has like five courses online I think it's called grow with Google or something where they're teaching how to be a UX designer how to do this how to do that and it's free so that they can get more people to apply for jobs and the average job entry salary for these things is like 80k so i i i find it's very weird in the world i think there's like a group of people who want the world to be more unfair than it actually is because it makes them feel more virtuous signaling good well that's their community that's how they find that there are other people who love that they tweet that the world is unfair so they and they have to and it typically like is a certain type of person i'll just leave it at that okay can i so i'm going to

Speaker 1 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.

Speaker 1 And I'm going to actually teach it myself this next cohort where I just teach people how to start companies.

Speaker 2 All right, let's plug it. How can they find out where Founder.university?

Speaker 1 That's it. There you go.
Yeah. I mean, it's basically it's free.

Speaker 1 The way I did it was you apply. If you want to build a company, you pay $700.

Speaker 1 If you go and you get to week 12, we charge your stripe back, the card back, the 700 bucks.

Speaker 1 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.

Speaker 1 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.

Speaker 1 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.

Speaker 1 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.

Speaker 1 I'm like, no, I've invested in 350 companies. Like

Speaker 1 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.

Speaker 1 I get it. But I'm telling you, like, on the streets, ground level truth.
We all meet with founders all day. It's never been more diverse.
It's never been more open.

Speaker 1 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.

Speaker 1 Like it is post-pandemic, all people care about is like, show me your metrics, show me the product, show me your team, what are your skills, great, let's go. What's your growth rate?

Speaker 1 It's basically become like as beautiful of a meritocracy as I've ever seen. And man, you say the M-word, it freaks people the fuck out.

Speaker 1 I'm like, why is this so scary for you that Silicon Valley is a meritocracy? And they're like, because it's not. And I'm like,

Speaker 1 it kind of is.

Speaker 2 Can I answer your question earlier of why I think all in works? Yes.

Speaker 1 All right. Go ahead.

Speaker 2 So I think you've got the perfect storm of three things.

Speaker 2 The first thing is...

Speaker 1 A lot of theories on this out there, by the way.

Speaker 2 billionaire porn.

Speaker 2 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.

Speaker 1 You're doing shows from boats and jets. Yeah.
So there's like we've done one from a jet, but yeah, there was definitely two boats in the last two years.

Speaker 1 That's true.

Speaker 1 Not by boat.

Speaker 2 In some peak moments of All In, it's like watching billions in real life. It's like you hear Chamoff talk about this spread trade, and you're like, this guy's got a lot of money on that spread trade.

Speaker 2 And like, does he actually have a key insight here?

Speaker 2 And like, there's this interesting intrigue there. So bucket one is like billionaire porn.

Speaker 2 Bucket two

Speaker 2 is

Speaker 2 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.

Speaker 2 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.

Speaker 2 And this feels very like a lot of it proved out to be like this was good information before it was massive.

Speaker 1 All four of us are information junkies with a lot of research and teams that come together.

Speaker 1 How many people,

Speaker 1 All In, how many people touch an episode of All In?

Speaker 1 One.

Speaker 1 Producer Nick, that's it. No, no, I mean, but like the research, the like.
I don't know.

Speaker 1 I'm pretty sure.

Speaker 2 Make sure text files open on people's computers when they're talking.

Speaker 1 We have a docket with 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.

Speaker 1 So I do that with my team, the docket, but the docket is built from the five or six stories that people submit to our group chat and say, hey, put this on the docket.

Speaker 1 And

Speaker 1 I think Sachs has some research help. I'm sure

Speaker 1 Friedberg and Chamoff.

Speaker 1 read the stories or they're well read. I mean, all of us read constantly and we're in the information business of talking to people about the the world.
So, you guys are investors. You know how it is.

Speaker 1 Like, you do 20 meetings a week with founders. They're going to tell you everything about the world.

Speaker 1 And you guys are young still, but imagine you do that for 20 years. Like, you're going to get smart or you're a journalist for 20 years.

Speaker 1 You're going to get pretty, I wouldn't necessarily say smart, but you'll be informed.

Speaker 2 And if you're hearing the right pitches, you actually are getting like cutting-edge information before it's widely available.

Speaker 1 Definitely. So, okay, that's number two.
So, yeah, we probably have a slight information edge. Yeah.
Certainly, a huge information.

Speaker 1 I will say the information edge compared to journalists having been, this is not not a dig to my journalist friends. I was a journalist.
I had 75 people at the magazine.

Speaker 1 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.

Speaker 1 And we probably, now looking back on it, I think we had between five and 35% of a story. And I know that's like probably triggering to a lot of journalists that they have that little information.

Speaker 1 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.

Speaker 2 You get enough to run with, and you feel like, okay, now there's enough story here, let's do it. And like, that's clearly not the whole story, but it's enough to put the piece together.

Speaker 1 You're trying. And then over time, process journalism, as some people have dubbed it, maybe the six or seven stories will tell the full story.
Yep.

Speaker 1 Which a third component that makes it successful.

Speaker 2 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.

Speaker 2 And so, like, if we can make history fun,

Speaker 1 then

Speaker 2 listen to four hours of us diving into stuff you would never read in a book. And you guys do that in spades.
Like, it is just so fun to, like, temporarily join your world.

Speaker 1 I mean, the fact that

Speaker 1 you, as a podcaster who makes elite content, like top 1% content, find it compelling is just, yeah, that's very,

Speaker 1 listen every week. Don't miss it.
I can't. Literally walking the baby up and down the hills, listening.
to the notes. I mean, I have people tell me they listen to it twice, they take notes.

Speaker 1 I'm like, wow, that's great. You know, I listen to it.
Don't take notes. Maybe I should take notes.
Well, anyway, I was very intentional with my role in it to step back

Speaker 1 and be like the point guard.

Speaker 1 But, you know, I'm a shooting guard too, so sometimes I will want to shoot the ball and I can do both. I'm a combo guard.
How did the Freeburg host episode come about? So one week

Speaker 1 you switched roles. Well, he was like, I think this could be done better.
This could be be better, and that was like, go ahead. And I just like, sure, I'll just shoot.

Speaker 1 And you pass the rock and I'll. I was like, yeah, you want to go? Go ahead, show us.
And he did a solid job. But let's be honest.
It's not a point guard.

Speaker 1 It's not showtime, that's for sure.

Speaker 1 Like, I don't think people are going to go to watch him play point guard. I mean, he did a serviceable job.

Speaker 2 Put that on his tombstone.

Speaker 1 No,

Speaker 1 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.

Speaker 1 I was like, listen, Sachs wants to talk about current or his politics. I'm giving him his red meat.
Here's your quinoa.

Speaker 1 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.
So good. You know, it was a distinct effort.

Speaker 1 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.

Speaker 1 You see it every episode. Sachs would disengage during science and Kinois

Speaker 1 would disengage during politics.

Speaker 1 And what I've been trying to do is keep both of them involved when the other is doing stuff. And Shamoth and I are involved.

Speaker 1 That's a hard job.

Speaker 1 That's a delta.

Speaker 1 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?

Speaker 1 Do my interruptions, I call them interjections,

Speaker 1 uh do they help and i actually looked at the interjections and if you look at mclaughlin have you did you guys did not grow up on mclaughlin super unfamiliar so the mclaughlin group was like the best sunday morning show and like it was so good like s and l 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 it and it became so competitive that you wanted to watch it yeah now what i didn't realize by adopting that would be that Sachs is the ultimate debater and will fight like a dog until he wins any debate.

Speaker 1 And so I may have pushed

Speaker 1 Sachs 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.

Speaker 1 And then some people in the audience are like, you have to be the fact checker for Sachs. And I'm like, no, that's not my right.
I'm not real-time fact-checking Sachs.

Speaker 1 And so that is a delicate balance of like,

Speaker 1 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 means. So I'm like, explain that.
Right.

Speaker 1 And I'll stop somebody.

Speaker 2 Now, I mean, you're expanding the TAM to dentists.

Speaker 1 Like, when that's correct. Thank you.
So people are like, oh, J. Cow's an idiot.
He doesn't know that term. Or I say to somebody, can you unpack that? Can you explain that?

Speaker 1 Obviously, you're not going to be able to do that. You know, that's for my story.
You were the third or fourth investor in Uber. Yeah, like exactly.
Well played.

Speaker 2 I think he's been in Robin Hood too.

Speaker 1 Like

Speaker 1 wow, who knows? And I'm like, dude, like I'm asking that question on behalf of the audience. So when I'm moderating,

Speaker 1 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?

Speaker 1 And she's maybe playing point guard a little bit and I'm shooting and then sometimes I'll pass it to her and she shoots. Like I can travel between those roles.

Speaker 1 And, you know, in that role, I'm acting on behalf of the audience. And I get the sense, like, he's going, Chamat's going too fast.
They don't know what the spread trade is. Let me pause.

Speaker 1 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.

Speaker 1 And that's what I think has brought in, to your point, a lot of the dentist crowd.

Speaker 2 And having an intimate sense of where your audience's edges are is a really important role there. Like it's a number of guests on.
I'm always trying to catch.

Speaker 1 Yes.

Speaker 2 Where do they just go slightly too deep? And I need to pull them up.

Speaker 1 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 crazy rabbit hole? There's no clock in this room.

Speaker 1 Well, they're going down some rabbit hole that has never existed in media before. Right.
So.

Speaker 2 And you want to let them go, but you need to make sure they're taking the stairs. Because if they just jump in, you're like, oh, God, no one has any context.

Speaker 2 They can't learn anything new because you're not connecting it to something they understand.

Speaker 1 They just jumped into brain surgery.

Speaker 1 Let's just explain to us what's going on here. How are we going to chop up this brain? Right.
Like, yeah.

Speaker 1 Yeah, it's a bit of an art, but you know, I have to say, like, it's, it's been a different muscle for me to flex, and it's been great fun for me.

Speaker 2 The other thing, like, I don't know if you think about it on this axes at all, but like, I kind of think of there's, I used to think it's very binary. Like, there's two categories of podcasts.

Speaker 2 There's candy and there's vegetables. And, like, I listen to the audio version of Strateckeri, and that's my vegetables.
And it's not like deeply, it's enjoyable intellectually, but it's not like fun.

Speaker 2 And

Speaker 2 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

Speaker 1 you 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

Speaker 2 If I missed out on 20 minutes because I was like brushing my teeth and then I left

Speaker 2 and I came back and I'm like, oh, I didn't actually miss anything because this has just been,

Speaker 2 it's comforting. It's like, I love all the stuff he's talking about, but like, it's not must listen every time, every minute, every second concept.

Speaker 2 And I'm not using hard parts of my brain to understand.

Speaker 1 All in has become candied vegetables. It's both.
It's both, yeah, for sure. Yeah, I thought I'd try to do it with this week in Startups and All In is try to have it be both.

Speaker 1 A little bit of personality, a little bit of entertainment, some fun hot takes.

Speaker 1 Related but separate topic.

Speaker 1 Silicon Valley. Yeah.
I feel like, especially, there's a lot of part of the, in the origins of all in, there's a lot of like bashing on San Francisco politics and California.

Speaker 1 I'm like, there's a lot of crap wrong here. Yeah.
But you guys are all still here.

Speaker 1 How are you guys feeling about that? Yeah.

Speaker 1 How do you feel about that? Like, what do you think of the Bay Area?

Speaker 1 You know, I lived in New York, Brooklyn, then Manhattan, and then I lived in L.A., and then I lived here. And so

Speaker 1 I think my, I'm moving to places I enjoy less and less each time. Like, I enjoyed Brooklyn and Manhattan much more than L.A.
LA. I enjoyed LA much more than San Francisco.

Speaker 1 So I don't know where to go next, but I'm going to go somewhere.

Speaker 1 So why are you still here then? Well, I can't. There's no reusing for me.
I came up here because I had a lot of friends up here

Speaker 1 and I had done LA.

Speaker 1 And I was like, I wonder how far, you know, I had 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.

Speaker 1 I wonder how I would do if I was up there in the industry. And I was kind of this kind of.

Speaker 2 Because if you wouldn't, you'd always wonder.

Speaker 1 Well, Michael Morris used to call me the mouth from the south because they had like two investments in L.A. Oh, the mouth from the south is here.

Speaker 1 What if you've had to invest in Jay 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.

Speaker 1 It's quite nice. I

Speaker 1 would love to live in another city in my life or two.

Speaker 1 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.

Speaker 1 So I think for the rest of our adult adult lives, this is.

Speaker 1 I think the politics and not appreciating the politics of regulation and not appreciating

Speaker 1 the tech industry is really the problem. And then you look at this guy, Dean Preston, like he is dunking on

Speaker 1 the founder of Away and Stuart Butterfield from Slack. They're a couple.

Speaker 1 And he's like, we got a million, two out of them when they sold their homes.

Speaker 1 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.

Speaker 1 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.

Speaker 1 So you have one guy Dean Preston dunking on people saying, we have this 1%. So when they sold their $30 million house, we were able to extract a million, too.
That's why tech doesn't like me.

Speaker 1 And I was like, hey, dummy. Yeah, now all the future earnings are gone.

Speaker 1 Now, what's the

Speaker 1 California marginal tax rate is 13.3%.

Speaker 1 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.

Speaker 1 1.2 million from them selling their home versus 13% from their future earnings stream.

Speaker 1 Literally, the chef at Slack made a billion two, paid a billion two in taxes

Speaker 1 from their RSUs. Like, are you such a, where do you think that's the cert problem? Yeah, like the bill, the million two

Speaker 1 probably probably paid in taxes on their RSUs at slack like you absolute moron like you're literally so upset about their mansion and dunking and you're dunking on an individual's name but anyway the fact that we hate entrepreneurs who create jobs and wealth or certain people do it's just insane it's just insane like what I mean you could Go change the tax code.

Speaker 1 It's fine. Like, you know, raise the minimum wage.
Like Bernie Sanders and Elizabeth Warren attacking Bezos endlessly. And then

Speaker 1 Amazon starts paying $22 an hour,

Speaker 1 gives you benefits, and pays for your college. And it's like, okay, hold on a second.
I know what Bezos just did.

Speaker 1 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.

Speaker 1 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.

Speaker 1 And you wanted everybody to have universal health care, and he gave universal health care. Like, that is literally what Bezos did to them.

Speaker 1 How important is it? Maybe you could argue that, like, them pushing him pushed it, but no, no,

Speaker 1 definitely. It is literally him showing, like,

Speaker 1 it's the Amazon crew showing, like, let the free markets work. Like

Speaker 1 the DoorDesh, Uber,

Speaker 1 Amazon, Starbucks, absolute

Speaker 1 race and battle to just hire entry-level employees and make it delightful for them is what has driven,

Speaker 1 you know, and a lack of immigration is what has driven these salaries up, right? And the benefits up. It's extraordinary what's happened with the free market.

Speaker 1 Minimum wage is still $7.

Speaker 1 Federal minimum wage is $7 and change still, right?

Speaker 1 And 15 here in the city in New York is 15. Like,

Speaker 1 yeah, it's weird.

Speaker 2 All right, listeners, this is a great time to thank our longtime friend of the show, Vanta, the leading agentic trust platform that helps you automate compliance and manage risk.

Speaker 2 David, I caught up with Christina and the Vanta team to get the latest.

Speaker 1 Ooh, nice.

Speaker 2 So listeners probably know, Vanta started by focusing on compliance automation. So helping companies to get their SOC2, ISO 27001, GDPR, and HIPAA.

Speaker 2 The big insight was to build a system that could monitor all of your compliance and risk continuously, not just once a year for your audit, so you could feel confident in your security posture all the time.

Speaker 2 But now they have realized that the business that they're really in is making it easier for you to earn the trust of your customers.

Speaker 1 Yep, makes sense.

Speaker 2 So when you start scaling, you end up with more compliance and security requirements and more tools, which can get very chaotic.

Speaker 2 Vanta has become the always-on AI-powered security expert that scales with you. And as Vanta puts it, they are the best security hire you'll never have to make.

Speaker 2 And of course, the fastest growing companies in the world like Cursor, Snowflake, Replit, Linear, and Ramp, all use Vanta to make sure that their security programs are always a step ahead and function as a real driver of growth for the business.

Speaker 1 Makes total sense. It's funny.
When we first started working with Vanta almost five years ago, I think it was,

Speaker 1 we thought, oh, this is one of those great acquired universe products that lets you focus only on what differentiates your product and outsource the things that don't.

Speaker 1 But over the last couple of years, their product has advanced so much that it's not just Vanta does that for you. It's now actually Vanta does that better.

Speaker 1 Without a real-time monitoring system, there's just no way that you could give your vendors and customers this level of confidence and trust. Yep.

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Speaker 2 You can just head on over to Vanta.com/slash acquired and tell them that Ben and David sent you, and you'll earn $1,000 of free credit. That's Vanta.com/slash/acquired.

Speaker 1 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.

Speaker 1 Tell us about it. Well, I find great purpose in what I do.

Speaker 1 And when my friend Tony Shea died, I really thought deeply about like what I wanted to get out of the rest of my life. And I realized like

Speaker 1 these are the things I really love doing. And these are things maybe not so much

Speaker 1 and I just realigned my life over the last two years and so what are the

Speaker 1 buckets yeah exactly so I can tell you the things that just to me I'm just not going to get any pleasure of out of life

Speaker 1 working like no offense to my incredible lawyers but negotiating term sheets and legal and HR issues and accounting and operations and tax and you know that entire stack of things

Speaker 2 not fun to me not fun at all and I'm sure you never viewed that as fun but at least before you were like I'm willing to put up with it because it maybe it's a thing that creates value enough for me to do it.

Speaker 1 Doing my podcast every day. Absolute joy.

Speaker 1 Entertaining an audience,

Speaker 1 thinking about the world and having these conversations. I had Toby from Shopify on today.
I leave the Toby interview. It's like his third or fourth time on the pod.
That's awesome.

Speaker 1 And it's just like, instead of us having dinner or lunch, we just record a pod. The end.

Speaker 2 Did you hear the person or did he eat?

Speaker 1 No, just talked on Zoom.

Speaker 1 I had to start it because he did that tweet about his compensation tool where, you know, here's your total comps, use the slider. I was like, that's brilliant.
Come on the show.

Speaker 1 You want to come on the show and talk about it? He's like, yeah, of course.

Speaker 1 And so, like, those conversations, I just looked at them and I'm like, my energy coming out of the show

Speaker 1 is on 11.

Speaker 1 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.

Speaker 1 They

Speaker 1 every day get on there

Speaker 1 and they seem to love it. And I do.
And so I just committed to doing it every day. And I love it.

Speaker 2 Isn't it weird when there's something that takes a ton of work, but somehow doesn't drain you? Not at all.

Speaker 1 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.

Speaker 1 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 someone

Speaker 2 having someone to play off of, I feel like that's the thing that's kept Acquired going. Yeah.
Is that like you and I can like it?

Speaker 1 I don't don't know how you did it alone for a decade.

Speaker 1 Well,

Speaker 1 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.

Speaker 1 And then I was like, well, however many ages,

Speaker 1 I'll do it five, six days a week, whatever.

Speaker 1 And

Speaker 1 I enjoy meeting with founders

Speaker 1 when they fit a certain profile.

Speaker 1 But it's very hard to meet with a large number of founders given how many are coming in.

Speaker 1 And it's hard to work with them when they're they're just talkers yeah to me that's a very hard part of the job because it becomes very repetitive so how have you excised that well i created a platform founder university where if you want to build something i will talk myself to 200 people you can build and then whatever arises as the performance and the product

Speaker 1 you know and they as people move from talkers to the walkers to from, you know, when they actually start building stuff, that's when I get great joy.

Speaker 1 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.

Speaker 1 Nobody's, yeah, I don't, really understands what I'm doing. And I kind of like it that way, but the Angel Syndicate is now the largest syndicate in the world.

Speaker 1 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.

Speaker 1 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.

Speaker 1 And it's in really high-quality companies. I'm getting better at.
There's 11, I have 22 people, and 10 on the media side, and 12 on the investment side.

Speaker 1 And of the investment team, like people don't understand. They're like, oh, you're a solo GP.
I'm like, yeah, but 12 people.

Speaker 1 Those people are doing 60 introductory meetings per week, six, zero. And then we're doing maybe 15, 20 second meetings.
So there's, it'll be 100 meetings a week shortly, probably on the 12th.

Speaker 2 across 10 people or 12 people.

Speaker 1 But you're not doing the. I'm not doing them.
Yeah. And what happens is.
You had this line.

Speaker 2 Was it on, it was not on, it was on Twisted.

Speaker 1 Not for me.

Speaker 1 That's a lot of work. People say that's a lot of work, but you're like, you have enough for me.
That is the new philosophy. This is why my energy is really high.
This is your.

Speaker 1 I have told everybody who comes to work for me, I work 60, 70 hours a week. Keep up.

Speaker 1 If you can't keep up, don't be here. I'm looking for a fixed 50, a solid 60 hours a week.

Speaker 1 You don't have to match me 67, but 60 or 70 hours a week, but keep up.

Speaker 2 And are you looking in that team? Are you looking for like the next Jason Calicanis to be a part of that team? Or is it like someone who likes doing that part?

Speaker 2 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?

Speaker 1 I'm open to all of it.

Speaker 1 I'm open to all of it. They don't need to want to have my, you know, absurd,

Speaker 1 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 very long.

Speaker 1 Yeah, I might be.

Speaker 2 You'd come, you'd learn.

Speaker 1 It's on five with two. If people come and they work for two, three, four years and they go start their own venture fund or whatever, I'm also talking.
It's great.

Speaker 1 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.

Speaker 1 I said I want to do it twice a week, Tuesday and Thursdays, 2 to 4 p.m.

Speaker 1 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.

Speaker 1 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.

Speaker 2 You know, teach the course. Are you enjoying the LP fundraising?

Speaker 1 I am now, yeah.

Speaker 1 I'm kind of like,

Speaker 1 remember in X? I don't know if you watch Billions. Yeah.
oh yeah every episode great so you know like at some point um

Speaker 1 uh

Speaker 1 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 is 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 wait and so you've talked about this now you but 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 um i've had select institutions make small bets the first one was 10 the next fund was 11 and then the last one was 44 million the first fund i deployed in five years second fund two years the third fund two and a half five years

Speaker 1 i was just that was my first fund it was you know me bill gurley dave goldberg rest in peace tony shea rest in peace david sacks chamoth just a bunch of my friends put money in and it was to see if i wanted to be a venture capitalist and do this as a career and I was like yeah I just did it over five years and the second one I raised 11 took me six months to a year to raise the first it took me the second one took three to six months the

Speaker 1 no it took six months the third one took me three months to six months and in this one I I think I'll wind up raising in the first 10 days what I raised in the first

Speaker 1 Yeah, a couple of funds.

Speaker 1 I literally did two webinars, a couple hundred people came to each. So for for people who are listening, 506C is you can raise in public, which means you just can tell people I'm raising a fund.

Speaker 1 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

Speaker 1 aspiring VCs raise publicly. Right.

Speaker 1 You didn't raise publicly. No.
You did a private. I thought about it, but for a whole bunch of reasons.
Well, it's kind of scary because people don't do it.

Speaker 1 But if you have no track record and you want to raise, so like this guy, Mac the VC.

Speaker 1 Yeah, you did a great episode with it. Yeah, it was great.
I had him on.

Speaker 1 I had like, you know, first time founders for a season of Angel, which is like a subsection of the This Week at Service podcast.

Speaker 1 And I became an LPN's fund and he just told me, like, I just did like hundreds of meetings. I did like five meetings a day for a year.
And I raised my whatever, $10 million. And he's African-American.

Speaker 1 And he's like, it's just a matter of how hard do you want to work. And I'm like, well, be careful saying that publicly because there's a group of people who do not want you saying that.

Speaker 1 He's like, no, it's just all you have to do is you go to Angelish, you set it up, and then you just start talking to other VCs.

Speaker 1 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.

Speaker 1 But that's what I mean. But they also give it a, it's not that it's easy, but on the internet, too, you find your people who believe that,

Speaker 1 and then they believe in you, and then they back you, and then that's the link. Correct, correct.
And so the whole thing, but what I noted when I was taking my notes watching him was

Speaker 1 so many times people are like, oh, you're, when's your next fund? And I'm like, three years. They're like, oh, let me know.
And I'm I'm like, okay.

Speaker 1 Right.

Speaker 2 I'll put that right there in the place where I keep everyone who tells me.

Speaker 1 Yeah, three years from now what to do. Yeah.
And so, you know,

Speaker 1 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 in the middle of the year? Of course, yes.

Speaker 1 250 accredited, up to 10 million, and then 2,000 QPs. And so it's a lot more work.

Speaker 2 And QPs.

Speaker 1 Not for you. But not for me.
To catch all of you. 45 purchasers.

Speaker 1 Look at you playing Jason. I know you know what he's doing.

Speaker 2 I just want to dish the ball.

Speaker 1 I think it's $5 million in investable assets.

Speaker 1 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.

Speaker 1 And net worth. In net worth outside of your primary residence.
So there's a whole, and these things are going to change over time. But I believe that we're going to have a test for accreditation.

Speaker 1 And you'll be able to be sophisticated if you take a course. So I think that's coming in the coming years.

Speaker 1 So just like I democratized Angel Investing, wrote the book Angel, was the first syndicate on Angel List, the most successful syndicate on Angel List, created my own, got the domain name, the syndicate, created the largest one, have done 265 syndicate deals by far, like the largest amount of anybody, I think.

Speaker 1 I don't know. I mean, now as a participant with the fund on Angel List,

Speaker 1 those are big numbers.

Speaker 1 Do something consistently. Four SPVs on Angel List, 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.

Speaker 1 But anyway, putting all that together, I think now is the time to democratize venture capital.

Speaker 1 So that's what I'm attempting to do here is I want more people who are accredited and qualified purchases who've never been in a venture fund to look at the asset class and just consider it.

Speaker 1 It's high risk. It's high reward.
I'm in 20 venture funds myself, including yours. Thank you.

Speaker 1 And I'm sure.

Speaker 2 But don't pitch Jason.

Speaker 1 I'm sure

Speaker 1 you do yours. No, I mean, I'm just going to pick them based on people I know or people I know online or people on the pod.
And, yeah, I'll do one or two new ones a year.

Speaker 1 But this is kind of to the conversation earlier, like on the internet, this is the democratizing thing.

Speaker 1 Nobody's going to just give you, if you just, you know, nobody's going to just invest in your fun, but if you go do stuff,

Speaker 1 and then people are like, oh, Jason does stuff. Great.
I'm going to back Jason. Ben does stuff.

Speaker 1 Be of action.

Speaker 1 And it doesn't mean you have to start a podcast. You could be a blog.
You could do events. Founder.
You could create founder university, whatever it is. You can do any of those things.

Speaker 1 You can have a track where you can be an advisor to startups, whatever it is.

Speaker 2 Do you like the idea? I'm curious, as someone that's always raised from sort of individuals,

Speaker 2 do you like the idea of having some institution be like, can we invest $15 million?

Speaker 1 Oh, yeah, of course. I mean, I've had five million dollar checks, $10 million checks in the fund from institution, from fund to funds and institutions, you would know.

Speaker 1 But I would very much at some point, I don't need it. But it would be meaningful for me,

Speaker 1 both my parents are cancer survivors, to have Memorial Sloan Kettering's endowment or an endowment. CSF or something like that.
Yeah, somebody like that.

Speaker 1 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.

Speaker 1 And, you know, I got that from Sequoia. Like, you know, they would have this Sequoia dinner every year for the founders and they would say, here are what the foundations who are LPs

Speaker 1 are doing with the money. you made for them with your companies.
Click, click, here's what Ford Foundation is doing. Here's what this foundation is doing.
And you're just...

Speaker 1 Their conference rooms are named after their conferences are famously named after their

Speaker 2 powerful. Like, I find we have like state pension funds and stuff like that.

Speaker 2 That'll make you get in PSL ventures. And like, you take it much more seriously.
You're like, I am.

Speaker 2 Because it's not just about the reward. It's not like, oh, I'm so excited about what we're going to do for them.
It's like,

Speaker 2 this is really important

Speaker 2 to preserve and not grow, but like preserve this capital.

Speaker 1 Yeah, yeah.

Speaker 2 Which the psychology of doing that while you're taking big swings with asymmetric upside, that I find to be a fascinating dance.

Speaker 1 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 fund.

Speaker 1 And so there's this natural tension for

Speaker 1 acts like, which should it be? And he decided, yeah, I like when I have other people's money because he seemed to perceive like.

Speaker 2 I think he felt that he wasn't a somebody in his ecosystem, in his community, without managing outside cash.

Speaker 1 I think it's like playing, you know, in the bubble with nobody in the stands versus getting on the court at Madison Square Park. It's like, and there's people in the stands.

Speaker 2 Your numbers don't mean anything unless you're putting them up for.

Speaker 1 Dude, I'm doing this public, or I should say quasi-public. People that still have to sign up to

Speaker 1 come to a webinar.

Speaker 1 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.

Speaker 1 So, you know, I'm kind of enjoying it.

Speaker 1 And

Speaker 1 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.

Speaker 1 Small

Speaker 1 funds. We're a $50 billion endowment.
Yeah. And, you know, like, you know,

Speaker 1 at some point, like one of the ones who's the most rigorous, I wouldn't say exactly which one was like,

Speaker 1 we have a lot of respect for you. We know who you are.

Speaker 1 People would like you to sign a book and take a selfie with you when you're here.

Speaker 1 But I just want to be straight with you. We don't add many funds.
And if you go through through our process, it's going to take a lot of your time.

Speaker 1 And it's going to result in you not getting our money this time. I don't want to put you through that, but I respect you.
And if you want to do it, we'll do it.

Speaker 1 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 is...

Speaker 1 Was that in the last fund cycle? That was in the third fund cycle. Yeah, so now...

Speaker 1 So I will contact them. What I decided to do was, let's see what my syndicate members and the public want to do.
Let's see which QPs come out of the woodwork. Yep.

Speaker 1 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.

Speaker 1 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.

Speaker 2 Are there any downsides to doing the

Speaker 2 raising in public thing other than

Speaker 1 not that I can see? I mean, I guess you could fail in public to fail to raise the fund. That doesn't seem like something you're scared of.
No.

Speaker 1 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?

Speaker 1 I could just invest my own money in each company and then syndicate them and never have another LP.

Speaker 2 Right. But then you're raising capital every single time you're making an investment.

Speaker 1 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.

Speaker 1 Would anybody like to join me? Yep.

Speaker 1 And I don't have to have a fund. I don't have to do audits.
I don't have to do any work. Raise this.
So literally, this, you know, it's so funny hearing you say this.

Speaker 1 Myself, lots of our other friends in the ecosystem that are in similar positions, they're having this same question: like, on the one hand, I could do what you just said and do very little work, but, but have it all be pure.

Speaker 1 On the other,

Speaker 1 I could go do what you are actually doing and like raise, have LPs via count of it. Yeah, how did you weigh these two?

Speaker 1 I'm going into my second era, my second decade of investing.

Speaker 1 And I, again, last two years, a lot of like sort of post-pandemic and Tony's death thinking, huh,

Speaker 1 like, what's possible here?

Speaker 1 Because I've won so much in my life. I 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,

Speaker 1 and this is why, like, when the guys break my chops on the pod, I'm like, guys, I don't aspire

Speaker 1 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.

Speaker 1 Maybe get in 40 days of skiing, hang out with my kids, take them on the mountain, and then meet with like you know, early founders and be able to say, I help that company at the earliest stages.

Speaker 1 That to me is the rush. I found them first.
I backed them first. I sat there with them and figured it out with them.
We were talking about the legendary Twist episode 180 with you and Travis. Yes.

Speaker 1 Like, I mean,

Speaker 1 that's the secret before the show stuff, David. Yeah, that is the secret.
But from the Juice. I didn't talk about Travis.

Speaker 1 Yeah, but that was like, you know, you know, Urbu was such a baby company back then. And like, crazy.
One city.

Speaker 1 And I invested and I had an open angel forum where Cyan Bannister and Chris Fralick from First Round, you know, invested in the company. I think they both met them there.

Speaker 1 Sokka was there too, but he already, he had a relationship with Travis, so I can't take any credit for that.

Speaker 1 And Kevin Systrom was watching, and I was going to kick him out because he was at this co-working space called Dog Patch Labs.

Speaker 1 I worked there too. Yeah, I worked at Co-Tweet.
Yeah, so he was, oh, Co-Tweet, I know that. So he's sitting over there building Bourbon.

Speaker 1 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 give him

Speaker 2 so this open angel form was at dog patch labs here on the pier no way

Speaker 1 and then they shut down because it was gonna collect condemned yeah condemned um so that was there and uh noval track also did a bunch of like events there for angels i at the time noval and i were very friendly um

Speaker 1 not not friendly now but not we don't hang out or we but we used to hang um kind of bummed about that if i'm being honest um i really respect him and uh

Speaker 1 he was doing something called venture hacks at the time so he would just send an email with here are the five companies and i was doing it in person and he's like i'm gonna do this thing angel list i'm like well i'm just in-person thing and he's like great let's just you know trade notes or whatever and then he sent me the syndicate thing he's like do you know about spvs i was like i don't explain it to me and he taught me what spvs were he introduced me to assure fund management which i wound up investing in um did you buy that i didn't buy it i i mean i bought five percent of the company i invested in it but they back everybody and uh they've done more spvs like lit, like I don't know if they're up to 10,000, 5,000.

Speaker 1 I mean, they've done a ton of it.

Speaker 1 Seriously great group over there.

Speaker 1 And so he taught me how to do syndicates. And the first one I did was calm at four or five.
That's no, it's funny. I was looking forward to that.

Speaker 1 Like literally like winning a championship the first time you step on the court.

Speaker 2 I was looking at your track record getting ready for this and I was telling David, like, I think the word that I used, because like obviously Uber is some ridiculous multiple on a return.

Speaker 2 But then there's these other ones that are like promising but early. And then there's other ones where it's been a less than Uber multiple, but still a good Uber multiple.

Speaker 1 But you look at Calm.

Speaker 2 I looked at David and I was like, he sharpshootered that one.

Speaker 1 That one I could be even more proud of because

Speaker 2 it was like ridiculously early and like a super low basis.

Speaker 1 They had, it was $4 million. We put 370 AK in on 6%.

Speaker 1 And they didn't raise any money until it was a $250 million value. So no dilution.

Speaker 1 Sharpshooter. Sharpshooter.
And

Speaker 1 really, like

Speaker 1 I could even cry like telling the story, but Alex too and I became very good friends. And Michael Acton, you know, afterwards,

Speaker 1 because he wasn't actively running comm while Alex was. Alex at some conference, I was interviewing him and doing a little victory lap for him and

Speaker 1 giving him his flowers. And he said, I just want to stop and tell you,

Speaker 1 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?

Speaker 1 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.

Speaker 1 And we were trying to debate if we could, in good conscience, burn your money to do this. And we probably, Comm would not be here for 15 years.

Speaker 2 And they found a product market fit while burning through your money.

Speaker 1 I think so. I think so.
You're like, take more of my money. No, no, no.
But you have to think about that as like a that is not the case with Uber or Robinhood.

Speaker 1 I was along for the ride, let's be honest.

Speaker 1 I did not change the trajectory of that.

Speaker 2 But like, but for Jason Calicandis, calling it.

Speaker 1 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.

Speaker 2 That's like real angel investing.

Speaker 2 There's a lot of individuals participating in venture rounds.

Speaker 1 And like,

Speaker 2 no offense.

Speaker 1 Oh, hey.

Speaker 1 I don't take any offense.

Speaker 1 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're revenue to date, I think, when I invested ever yeah uh because they were selling the app for ten dollars because remember at the early stages there was no subscription model right in the app store you just sold an app for ten dollars the person had it for right so the business model of apps was make a lighter for a dollar then make lighter two yeah and charge three dollars and then lighter four would come out and you'd be like well this doesn't make any sense it's like making microsoft word 1.0 you buy it you throw it away it's like but we could just update it and it's like yeah but we need to make more money so shut the old one down so you'd buy Angry Birds and you buy Angry Birds Two, Angry Birds Three.

Speaker 1 And, you know, it was a really weird time. And then they're like, yeah, we're doing so.
They told me, like, you know,

Speaker 1 because, you know, I was under NDA as well. You know, hey, subscriptions are coming.
That's going to change everything. And then we're going to do $10 a year.

Speaker 1 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 the suggested donation?

Speaker 1 It's like $20. You know,

Speaker 1 I said, you want to church $10 a year. It's $20 a month.
How often often do you have to do this to

Speaker 1 get 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.
We're like, well, how often do you have to go and learn?

Speaker 1 I said, if you go weekly, that's good. I was like, so it's $80 a month

Speaker 1 to go, and we're charging $10 a year. So that's like $1,000 a year versus $10.
What if it was $10 a month? They're like, we've been thinking about that. I was like, okay.

Speaker 1 And they're like, okay, yeah, I think we're going to do that.

Speaker 1 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.

Speaker 2 So I've never made an investment at like pre-product market fit that's like now worth over a billion dollars. Like

Speaker 2 that's a very early to very successful. And I'm curious, like, did it feel any different when you were making that investment?

Speaker 1 Were you like, there's something more special here

Speaker 1 than my normal investment? Absolutely. Really? Absolutely.
And that's what I've...

Speaker 1 basically turned into a playbook at launch and that I'm teaching these 12 people how to do is how to do that.

Speaker 2 What do you think it was? Like what was when you look back and you're nine factors.

Speaker 1 Nine factors. Nine factors.

Speaker 2 Yeah. Wow.

Speaker 2 Angel.university. Angel.university.

Speaker 1 No, I'm not even teaching at angel.university, but

Speaker 1 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.

Speaker 1 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?

Speaker 1 Reasons to not invest? How many reasons to invest does it have?

Speaker 1 And, you know, like one of them for me, and everybody's got their different philosophy, I won't give all of them, but one of them is world-class design.

Speaker 1 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.

Speaker 1 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 all of anybody in the category.

Speaker 1 So Calm was better than Headspace, Robinhood was better than E-Trade. I mean, it's just, it doesn't take a rocket science to look at them.

Speaker 1 But when I first explained this to my team, they would bring me companies and they'd say, world-class design. And I'm like,

Speaker 1 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

Speaker 1 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. I mean, product page.

Speaker 1 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.

Speaker 1 That's good design. It's not world-class.
So let's, if we're going to say world-class,

Speaker 1 like a world-class performance is different than a serviceable performance, world-class cinematography, world-class script, world-class dialogue. That's different.

Speaker 1 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.

Speaker 1 I'm like, okay, well, let's find out. Where's their change log? Where's their roadmap?

Speaker 1 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.

Speaker 1 And somebody like Travis would be like, yeah, here, I'll get on the phone with this guy and we'll walk you through it. Here's what we're debating about on Sunday.
We're reprioritizing.

Speaker 1 And then a month later, they've like

Speaker 1 checked, check, check. And then you go like, if we're with Row, with Superhuman, and I was the investor in his company before that report of Roo, like the change log at Superhuman.

Speaker 2 Superhuman that people don't realize like,

Speaker 1 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.

Speaker 2 So here's an interesting question. We should ask Ruffle this because we've had him on the show three times now.
Product genius. Like,

Speaker 2 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.

Speaker 2 And

Speaker 2 I remember it being breakthrough when it came out.

Speaker 2 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.

Speaker 2 And why?

Speaker 1 Outlook support. You just don't, you know, when you hit Command K,

Speaker 1 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?

Speaker 2 I do.

Speaker 1 Okay. Yeah.

Speaker 2 Which it was all there when I started using it three, four years ago.

Speaker 1 I think a lot of those.

Speaker 1 things have gotten better and better. Yeah.
So it's just that like polish, polish, polish, polish, polish, polish.

Speaker 1 I really like want them to make snippets multiplayer. I want to share my snippets

Speaker 1 with your team. I love

Speaker 2 all of David's pass emails. They're so nice.

Speaker 1 I don't pass email anymore.

Speaker 1 You do it on the phone? No, no, I just don't

Speaker 1 know how to do it. I don't email anybody.

Speaker 2 I actually do have Sapph Pass emails from one of those.

Speaker 1 I've been literally creating a collection of how to pass with my team, and I'm standardizing that. I'm trying to

Speaker 1 founders. I don't know that I'll be successful, and this may be a mistake, but I'm trying to

Speaker 1 just not have

Speaker 1 I don't end up having a conversation with a company if I'm not going to invest.

Speaker 1 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.

Speaker 1 I don't.

Speaker 2 You basically don't take a pitch

Speaker 1 unless you're going to invest.

Speaker 2 It's the weirdest thing.

Speaker 1 Oh, that's very weird. So you do all your work up front.
You front load it, the DAC, everything. We're in this unique position.
You are too, but

Speaker 1 with Acquired, we're like, you know, we have every six months, we have six companies that we work with on the show right as our sponsors and our partners and we get to know them really well modern treasury and it's and i'm now an investor in just about all of those companies

Speaker 1 so it's not like uh they're pitching me it's growth stage investing yes it's like growth stage investing

Speaker 1 yeah they're not priced as if they're the winner most of the time yeah exactly they're gonna just keep compounding yeah good luck yeah pricing's gonna be hard well it depends we'll see depending on entry price we'll see yeah i don't know what's gonna happen to these companies after you know like flat is the the new up, but I think, you know, 50% haircut is the new flat.

Speaker 1 Well, telecoms got hit 50 plus percent.

Speaker 2 I mean, this week they got hit harder again.

Speaker 1 Yeah, I mean, I'm buying equities right now. I've been doing it at jtrading.com, and um, I am going to buy more.
Sorry about all four a couple weeks ago.

Speaker 2 Which one?

Speaker 1 Whatever I think. Oh, yeah, yeah.
No, no, I actually love Taiwan Semiconductor.

Speaker 1 Since Fix was the other one,

Speaker 1 Twilio. Twilio was yours, and I love that one too.
And I like Shopify as a pick.

Speaker 1 I'm actually really enjoying it. It's really

Speaker 1 balancing out, not investment advice, but it's balancing out my

Speaker 1 understanding of what public success is compared to private. And so for me, it's just a way, like, am I going to fight with a blast or no, I'm a Jedi I use a lightsaber.

Speaker 1 But, you know, if you learn to use a blast,

Speaker 1 it's not as elegant.

Speaker 2 It's helpful. It's really helpful.

Speaker 1 If you look at the very best people, the best GPs

Speaker 1 in venture over the past two decades, they all trade public stocks. And they do it for this same reason.

Speaker 1 They're going to fight with the saber, but like they want to know how to use a blast or use a blast. Yeah, or how to fight in an X-Wing or something.
It's not what a Jedi does, but Jedi will do it.

Speaker 2 It also keeps you really sensitive to the public cycles so that like,

Speaker 2 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.

Speaker 2 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.

Speaker 2 So

Speaker 2 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 doing.

Speaker 1 Yeah, I'm really enjoying understanding what the founders of those companies go through versus the founders of the private companies that go through, what the board's, decisions the board has to make of a public company versus the board of a private company.

Speaker 1 So it, you know, I'd like to join a public board at some point. It's probably not a good idea for me to have said that because I might get an invite for one and that might be too much work.
But

Speaker 1 yeah,

Speaker 1 especially given the market right now, I'm very careful. But you could also invite me to do that.
But it's just, it's basically. Especially through the show now.

Speaker 1 You have relationships with public company founders. Sure, of course.

Speaker 1 And if I really wanted to, I'm sure I could lobby. Oh, and I'm not sure.

Speaker 1 You don't have to be on the board, though. You can have a very good idea.
I'm really enjoying doing the analysis. And I'm doing it anyway with Molly every day.
Okay, you know, Twilio's or Adobe's.

Speaker 1 I just bought Adobe this week when they bought Figma.

Speaker 2 So funny, so did I. Not investment advice.

Speaker 1 Not investment advice, but I was like, they bought Figma.

Speaker 1 They tanked.

Speaker 2 Okay, so here's my theory on this. They bought Figma and tanked.
And I was like,

Speaker 2 why do people hate this? And they're like, oh no, Adobe's admitting defeat and that like they can't innovate in-house.

Speaker 1 And to me,

Speaker 2 I look at it like Adobe has customer channel and it was foretold five plus years ago that they were not going to build the next Figma. Like that would be a full rewrite of their entire software stack.

Speaker 2 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.

Speaker 2 But if they can get that through Adobe's channel, like I think that is an absolute win-win acquisition. And all these people that are like, oh, they're going to ruin it.
They're going to kill Figma.

Speaker 2 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.

Speaker 1 They're taking a YouTube approach.

Speaker 1 I think everybody in M ⁇ A knows now. Yeah.
Like

Speaker 1 WhatsApp. WhatsApp.
Just leave it alone. Don't screw it up.

Speaker 1 And then, so I like your analysis.

Speaker 1 I added to that analysis is if you're not going to win the war and you can build an alliance and then fight another war, like they've just removed the downside of Figma creating Photoshop.

Speaker 2 I'd be concerned for Adobe if they didn't buy Figma.

Speaker 1 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.

Speaker 1 You just discounted the right move. Fantastic.
It would be like, people are like, oh, you know, the Warriors signed Kevin Durant.

Speaker 1 And you know what? We're going to lower.

Speaker 2 But they paid a lot to get him on the team.

Speaker 2 Yeah. And oh, you know what?

Speaker 1 We're going to lower the cost of the tickets. It's like,

Speaker 1 okay, I'll buy courtside seats or, you know, or they're lowering the odds in Vegas. It's like, wait, why are you lowering the odds? Their odds increased.
I'll place that bet.

Speaker 1 So it's just an obvious bet. And then there's all that's left is Canva.
And Melanie's awesome. Totally different thing.
But yeah, and they have a free Canva already.

Speaker 1 And, you know, what if there's always the internal people who are penciling out that spreadsheet? Yep.

Speaker 1 There's a group of MBAs who penciled out that spreadsheet with Figma, no offense to MBAs who are listening.

Speaker 1 And they said, hey, boss, if, X, Y, if, X, Y, Z, and they said, you know, here's like five potential paths.

Speaker 1 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,

Speaker 1 okay,

Speaker 1 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.

Speaker 1 But they may not have all the non-designers in there. Only designers pay Adobe.
Right. Well, no,

Speaker 2 they have marketing cloud, but that's a totally different creative.

Speaker 1 Yeah, yeah. Only.
But when you look at Figma, like, I got a Figma account, like, people who are doing,

Speaker 1 giving feedback on designs, the business side, the sales side can get into Figma.

Speaker 1 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.

Speaker 1 Sure, the CFO can come in and take a look at 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.

Speaker 1 And it's like, yeah, and the sales team and ops.

Speaker 1 And anybody else might as well be on there because that's where everybody is.

Speaker 1 These are some of the things that have a figma. It's like everybody's going to have a figma in the future.

Speaker 1 Just watch the product team build the product and put a comment in. And who cares if it's 100 bucks a year? It's cost of doing business.

Speaker 2 Any company that has like that kind of strong network effects inside an organization deserves a meaningful revenue multiple because they just their differentiator is literally the company's moat so like i i tweeted this but like if i have a castle and it has a moat around it that is much wider or deeper than your identical castle shouldn't you pay more for my castle because it's more defendable 100 like the virality of it i think sax made this point on all end two weeks ago which was like if they're paying 50x now and the company's growing Okay, they're paying 20x next year, but 25x, who cares?

Speaker 1 Right. This is such a high growth company.
And then I was just thinking, well, somebody's got a theory there.

Speaker 1 and when i sold web logs to aol people were like oh my god these people are idiots they gave 30 million dollars to you know for web logs inc they only got 200k in revenue what they didn't realize was aol autos aol tech aol lifestyle those were sold out at like a 90

Speaker 1 rpm revenue per thousand pages the ads were different cpms so then they would put an in gadget or an auto blog story or blogging baby or whatever other blog we had on the homepage of aol AOL and a half million people would flow through and then they would put those ads on our sites

Speaker 1 and then they would blow out 50 or $100,000 in ads a day on a blog and those people were like great because it was costing AOL to make content like $500 per piece of content $3,000 per piece of content on AOL.com slash autos whatever and we were doing it for at the time five bucks a blog five dollars a blog post because we said well people can write four an hour so it's 20 bucks an hour and it's $6 minimum wage.

Speaker 1 It makes sense. God, 50 years.
The media game has changed so much. And then I was like, you guys are doing 200K annual revenue? We had done 200K to date.
Holy over the 18 months. What is it?

Speaker 1 I mean, now, like, the world is a lot more than that. People went to the multiple and they were like,

Speaker 1 Jay Cowles is robbed.

Speaker 1 And I was like,

Speaker 1 okay, $30 million.

Speaker 1 And then I look like what do you think? Like, here's a I look like an idiot five years later. And that's the best, the best M ⁇ A is when you look like you robbed the bank.

Speaker 1 And then five years later, it looks like you robbed the founder.

Speaker 2 YouTube, Instagram, Figma will be in this category.

Speaker 1 Yeah, when they bought Instagram, they're like, 30 people work at this company and they gave them a billion dollars. You guys are morons.
And now it's $100.

Speaker 1 Here's a thought exercise question. Obviously irrelevant because you don't monetize it.

Speaker 1 What do you think the enterprise value of all in is? Well, it would do $10 million in,

Speaker 1 when I was at the code conference, a lot of people have been trying to buy it or you know, put it as part of their network, obviously.

Speaker 2 Which would kill it.

Speaker 1 Yeah. My partners are right.
Like, let's not make money from it.

Speaker 1 Part of the delightfulness of it is that we're not trying to monetize it. Well, but you do get a huge economic value out of it.

Speaker 1 Shamaf pulled me aside at some point and was like, hey, Schmuck, like, just we're friends. Like,

Speaker 1 your next fund will be bigger. Hey, dumb.

Speaker 1 And I was like, you know, when you have a friend who can be like, hey, dumbass, like, that's a good friend. So I appreciate Shamov saying that.
And he's right. And it's playing out.
And we had a rule,

Speaker 1 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,

Speaker 1 Frieb,

Speaker 1 we talked about his SPAC, you know,

Speaker 1 I

Speaker 1 embraced Paul. Yeah, he did.
He just found a target for it.

Speaker 1 Jamat talked about the healthcare company. The healthcare company, which is, I mean, we wanted to talk about that because Jamath and I both agree, like, maybe we're, I mean, maybe,

Speaker 1 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.

Speaker 1 I think all science is showing that.

Speaker 1 So, you know, to make software that could help kids with ADHD is like noble.

Speaker 1 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.

Speaker 1 So, anyway, and the event did a couple million dollars, had a small profit,

Speaker 1 but it was the number one tech event of the year by far. Right.

Speaker 1 So,

Speaker 1 you know, I'm kind of bummed that, you know, Freeberg's a little bit of a blocker for it, but I might turn him around and we'll have a vote maybe on the other side. I'm doing another one.

Speaker 1 Oh, well, I'm going to do another one. The question is, am I doing it under the all-in brand or do I have to create a new brand for it?

Speaker 1 And so, I told the guys, listen, I'm going to do it again. Well, Code Conference is done.
So, like, there's a value. Code Conference is done.
Yeah. They need a new host.

Speaker 1 That's crazy that that can be done.

Speaker 2 Like, it's such a value.

Speaker 1 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.

Speaker 1 And, you know, I really respect what Kara has done, you know,

Speaker 1 in terms of like she does stuff and then she moves on to the next thing and tries.

Speaker 1 Like, you know, it's kind of my approach as well, which is like Bob Dylan, you know, said, like, don't look back kind of thing.

Speaker 1 And he always tried to make the next album and forget about the past one. And much to the chagrin of people who loved him as a folk artist and didn't like, you know, like a Rolling Stone.

Speaker 1 And when he went electric, they booed him. You know, I was like, really? You're booing Bob Dylan because he's using an electric guitar? Are you guys dumb? Like, did you hear all along the watchtower?

Speaker 1 Like, this is incredible.

Speaker 1 And so I think, you know, Kara Swisher, like, moving on, but Jim said he's going to keep doing it. And, you know, it's probably a small list of people who could actually host that credibly.
You know,

Speaker 1 which is the smallest.

Speaker 1 And so. Which you're definitely on.
I am, you think?

Speaker 1 How could you? Can you not make that work? I mean, I'm not even saying that to like make you feel like you're not. No,

Speaker 1 I'm putting a little bit of information. Okay, okay.

Speaker 1 You're joking about being humble.

Speaker 2 if it had that kind of prestige it seems like freeberg would want to do it it seemed more like the thing he was averse to is the like

Speaker 1 yeah i mean whatever the issue is like we've had our issues um we will have issues um but um i think that there's basically two possibilities for all in summit um i'm going to present it to the boys uh and say like here's the plan

Speaker 1 yes or no and we agree we'll put it to a vote so we put it to a vote if three of us want to do it we'll do it and if two of us want to do it, then we can't.

Speaker 1 And if I already, Freeberg already said, if you do it on your own with a different name, I'll come and support you and I'll show up to do a talk or do an interview or whatever. And I was like, great.

Speaker 1 So I'll do it with a different name if they don't want to do it.

Speaker 1 And the fans can decide if they want to come or not.

Speaker 1 Partially in. Partially in, exactly.
So, you know, it's up to the boys if they want to do it. But it was like a pretty great success.

Speaker 1 You already have call-ins. Yeah.
Well, yeah. And

Speaker 1 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.

Speaker 1 And it's really made great progress. So I want to be supportive of him.
And I have a small investment in it. Do you think it's very meaningful? On the one hand, this is ridiculously.

Speaker 1 On the other hand, it might be ridiculously low.

Speaker 1 It's worth 50 million to answer your question. 50 to 100 million.
I mean,

Speaker 1 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

Speaker 1 know

Speaker 1 have. If Chamoth or Saks 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,

Speaker 1 possibly 10. You know, like, so yeah.
But that's the thing. Like, I think, like, man, weblogs, like, you were doing 200K of revenue.
You sold it for 30 million. Pretty great.
Takeaway, yeah.

Speaker 1 And now, look at this. Like, you know.
Yeah, I mean, listen, I hope it keeps going. I hope we can keep it on track.
And,

Speaker 1 you know, I love doing pods. This week in startups is a juggernaut as well.
You know, it's a lot of fun. Yeah, that was for 10 years.
And all in is.

Speaker 2 What is that, like a quarter million listeners or something?

Speaker 1 Yeah, something in that range. Yeah.
I mean, it's hundreds of thousands per episode.

Speaker 1 Yeah. It's a very niche podcast.
You know, I'm not trying to make it all in.

Speaker 1 I'm trying to make it for founders. And so, you know, if in order to make it bigger, it'd have to be worse for founders.
Right. And so we talk about it.
That's what we think about with ourselves.

Speaker 1 So I want founders and capital allocators to listen to it. And I'm not trying to move up the rankings.

Speaker 1 I don't mind, you know, hanging with, you know, all in being number one in tech and then hanging out with you guys at, you know, slumming it at six to 15

Speaker 1 with you guys in the rankings. It's like, that's where we belong.
Like, I got number one on list.

Speaker 1 But who's counting? Whatever. You know, that's where we belong with these things, right? Like, it's like it's a niche podcast by definition, right? Like, it's not supposed to appeal to everybody.

Speaker 1 And you try, if you want to appeal to everybody, like, read the Bible. Like, that's if you go to the, this is the biggest thing.
Literally, this guy who reads Bible passages and he and it's huge.

Speaker 1 It's like, if you can literally

Speaker 1 read the Bible or Ben Shapiro dunking on Libs. The end.

Speaker 1 That's like, that's how you do it. Or do it or do it daily.
But Joe Rogan's out, right? He's on Spotify. Right, right.
You know, he's not in the other ranking.

Speaker 1 So, I mean, 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 County. It would be a fun equipment.

Speaker 1 That episode is Howard Stern. I feel like it's underappreciated how much Howard Stern is doing.
I copied my

Speaker 1 that's the playbook.

Speaker 2 That should be the next Taylor Swift type episode that we do.

Speaker 1 Yeah, no, for sure. He wrote the playbook.
I literally took notes for it. King of all media.

Speaker 2 Do you know him?

Speaker 1 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.

Speaker 1 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.

Speaker 1 Sound familiar? Yep.

Speaker 1 He branded them. Yep.
He showcased them. the whack pack, you know, all this stuff.
Did he ever do an event?

Speaker 1 He used to do live events. He did the U.S.
open source, where, and then he would do Howard Stern's like New Year's Eve celebration.

Speaker 1 So, yes, he did the equivalent of those in New York, but it was a very New York thing. So, he like he played tennis against Baba Bui.

Speaker 1 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.

Speaker 1 And then he did his books,

Speaker 1 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.

Speaker 1 Literally going to do it. Are you really? Yeah.
I mean, I have to do it. Just you or the besties? No, just me.
The besties don't want to do it. They don't have time for it.

Speaker 1 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?

Speaker 1 You know, and that's a lot more work, though. Way less.
Well, you know, we would have to show up in a location. We'd have to do it weekly.
You know, there'd be some format, some shiny floor, whatever.

Speaker 1 It's a different beast. I don't think they have the time for it, if I'm being honest.

Speaker 1 But for me, I would like to do a reality show in the Gordon Ramsey kind of vein, you know, where I'm helping founders. I think it'd be great for reach.

Speaker 1 So

Speaker 1 I had done a reality TV show with NBC and the Weinstein Corporation.

Speaker 1 Oh, wow. Yeah, and it didn't make it on air, but I have the...

Speaker 2 You should be a shark tank judge.

Speaker 1 I had been, they had reached out before. Mark Bernard had reached out early on when it was dragon's den

Speaker 1 before when they were gonna bring it here so when it was dragon's then they had reached out early but I wasn't very successful back then I wish but you know I think now I think I would I have the credibility and the advice to give that I could do a Gordon Ramsey style show that would be very entertaining and educational and 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,

Speaker 1 the major, you know, reality TV folks reached out, I think, in part because I was doing so well. Would founders and companies feel comfortable?

Speaker 1 Like, I feel like a really amazing window in insight would be. the type of conversations that you have with a founder as they're building the company.
Yeah, so they're going to be able to.

Speaker 1 Would founders and companies be open to that? Yeah, so the NBA show I had done the pilot for, which never made it on air,

Speaker 1 what was really good was really about, you know, 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.

Speaker 2 Did it get canceled because of the Hardware 161 stuff? Wow. So they were just like anything that was in his body.

Speaker 1 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.

Speaker 1 People don't know that about that. That's right, I forgot.
Yeah, that had the TWC at the beginning. Exactly.
So, you know, I had this NBC, you know,

Speaker 1 NBC bought the show in the room, loved it, and did the pilot. Came close.
And Shamath was on that episode, actually. He did the pilot with me.

Speaker 2 Oh, my God.

Speaker 1 He was like my VC friend who came in.

Speaker 1 My VC friends. It's hilarious.

Speaker 1 No, it's hilarious.

Speaker 1 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.

Speaker 1 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 it.

Speaker 2 I'll be gone soon.

Speaker 1 Well, you know,

Speaker 1 you never know. And, you know, I've had

Speaker 1 some friends, yeah. I have two friends who died young.
And I'm just like, I, you know, talk to my wife. I was like, I don't know.
Like, what if I make it another year or make it 25 years?

Speaker 1 But I want to make it count. I'm not going for max dollars.
Like, and so when the guys break my chops about that, I'm like, guys, it's not my priority. Like, literally, maximizing money is like.

Speaker 1 Well, also, like, you're probably at a point now where like literally not in the top 10. What is more money going to do? Like,

Speaker 1 you literally change

Speaker 1 my life. Like,

Speaker 1 You guys understand my life. It is ridiculous and charmed.
Like, I can do whatever I want. I have enough money to do a map.
My kids are fine. I can have whatever I want.

Speaker 1 I don't care about 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.
Now I'm good. 100%.

Speaker 1 I literally do not care about my money.

Speaker 2 Do you feel like that's a demon that you fight? Is like any allure toward?

Speaker 1 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.

Speaker 1 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.

Speaker 1 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.

Speaker 1 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.

Speaker 1 So when you guys do your thing in 10, 20 years, and it's like, okay, you know, here's Doug Leone and Moritz and, you know,

Speaker 1 here's

Speaker 1 Gurley, John Dore, here's Gurley.

Speaker 2 Like, if we are making a Mount Rushmore, you want to be on that with them.

Speaker 1 I would like to make it there, or at least be in the conversation.

Speaker 2 All right, listeners, it's time to talk about another one of our favorite companies, Statsig. Since you last heard from us about StatSig, they have a very exciting update.

Speaker 2 They raised their Series C, valuing them at $1.1 billion.

Speaker 1 Yeah, huge milestone. Congrats to the team.
And timing is interesting because the experimentation space is really heating up.

Speaker 2 Yes. So why do investors value StatSeg at over a billion dollars? It's because experimentation has become a critical part of the product stack for the world's best product teams.
Yep.

Speaker 1 This trend started with Web 2.0 companies like Facebook and Netflix and Airbnb. Those companies faced a problem.

Speaker 1 How do you maintain a fast, decentralized product and engineering culture while also scaling up to thousands of employees? Experimentation systems were a huge part of that answer.

Speaker 1 These systems gave everyone at those companies access to a global set of product metrics, from page views to watch time to performance.

Speaker 1 And then every time a team released a new feature or product, they could measure the impact of that feature on those metrics.

Speaker 2 So Facebook could set a company-wide goal like increasing time in app and let individual teams go and figure out how to achieve it.

Speaker 2 Multiply this across thousands of engineers and PMs, and boom, you get exponential growth. It's no wonder that experimentation is now seen as essential infrastructure.

Speaker 1 Yep. Today's best product teams like Notion, OpenAI, Ripling, and Figma are equally reliant on experimentation.
But instead of building it in-house, they just use StatSig.

Speaker 1 And they don't just use StatSig for experimentation.

Speaker 1 Over the last few years, StatSig has added all the tools that fast product teams need, like feature flags, product analytics, session replays, and more.

Speaker 2 So if you would like to help your team's engineers and PMs figure out how to build faster and make smarter decisions, go to statsig.com slash acquired or click the link in the show notes.

Speaker 2 They have a super generous free tier, a $50,000 startup program and affordable enterprise contracts for large companies. Just tell them that Ben and David sent you.

Speaker 1 When you guys are having the conversation in 20 years and I'm gone or I'm retired and you're saying Mount Rocky, I can imagine you retiring. Yeah, I think it's possible.

Speaker 1 I met Don Valentine when they were like, you know, he was not active investing, but when I pitched Mahalo, he was in the room. He came up.
I talked to him. He was, oh, he was still hanging out there.

Speaker 1 He was out there all the time.

Speaker 1 Yeah, like, why retire? He was just awesome.

Speaker 1 But, you know, if you had that conversation right now about Mount Rushmore,

Speaker 1 like, you got to, okay, so who's on your Mount Rushmore? Well, I mean, you got to have Don Valentine. Yeah.
Right. That's just not possible.

Speaker 2 But how are you scoping it? Because you probably need Paul Graham, too.

Speaker 1 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.

Speaker 1 So Paul Graham's definitely running. But okay, so do you go with John Doar's in there along with...
So if you're doing firms, it's a lot easier because you get Khoshla, Dorr, and

Speaker 1 Perkins, Tom Perkins. You get the three of them at once.
You do Shakoia. Which

Speaker 1 people forget. Vanir Khoshla spent a decade at Kleiner Perkins with John Doerr.

Speaker 1 Yeah, and you had. Yeah, so I mean, you look at that firm, it's like, that's like the OKC with like James Harden, you know, whatever.
But then you have Doug,

Speaker 1 Leone,

Speaker 1 Mike Moritz, and Valentine.

Speaker 1 Ruloff. Well, Ruloff's going to be a little bit different.
Yeah, but you get all of them there active all at the same time. So those 30 years, and it's like, well, that's Mount Rushmore, right?

Speaker 1 So if it's a Mount Rushmore of Mount Rushmores is kind of how you might look at it. You know, you definitely have to have

Speaker 1 Sequoia and Kleiner.

Speaker 1 You got to have those early.

Speaker 2 The Fab Four era of Benchmarkman.

Speaker 1 The Fab Four era of Benchmark was truly something special. Yeah, the starting 11th,

Speaker 1 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.

Speaker 1 Like, is it...

Speaker 2 Well, it just depends how wide we're willing to scope, but is it like traditional Series A-type venture firms?

Speaker 1 I mean, is it Angelus, Naval?

Speaker 1 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,

Speaker 1 you know...

Speaker 1 Who else could be in there? That's just... You can argue for Founders Fund.

Speaker 2 You can say YC and Techstars.

Speaker 1 You have the Founders Fund. Completely different things.

Speaker 2 YC is like...

Speaker 2 three orders of magnitude more.

Speaker 1 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.

Speaker 1 But anyway, you definitely have Y Combinators in the running for that fourth spot, I guess. And then who else would you put in there? Masa? She's coming.

Speaker 1 Oh, Gary Miller. That's a high beta.
Well, no, I mean, but

Speaker 1 maybe,

Speaker 2 I don't know. Depending on the industry.

Speaker 1 Excel would be in the running for sure. It's Ron Conway.

Speaker 2 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.

Speaker 1 All right, so then let's just do this. Instead of Mount Rushmore, because we're talking firms.
So for firms, you do Mount Rushmore, right? So I think if you were just going to say the Hall of Fame.

Speaker 1 Yeah. Oh, yeah.
Just the Hall of Fame. Yeah.
And the Hall of Fame has...

Speaker 2 Let's just say, oh, dude, we should open the Venture Capital Hall of Fame.

Speaker 1 The Venture Capital Hall of Fame.

Speaker 1 The Investor Hall of Fame, Capital Allocator Hall of Fame, top 20. I was was trying to figure out when we were doing the benchmark episode research, which will be out by the time this comes out.

Speaker 1 2480 Sandhill Road is a very special building. It was the Forethought PowerPoint.
The Quadras Complex. Quadras Complex

Speaker 1 office. Then it was Microsoft Silicon Valley.
Three people for the shit about this.

Speaker 1 Three of us are so excited right now. This is the internet.
It's like, wow.

Speaker 2 We're segregating all the other people.

Speaker 1 Everybody else who cares about this is listening right now.

Speaker 1 And like Sebastian, Sebastian, who wrote the parallels. Yeah, yeah, yeah.
You guys are taking this way too seriously. It's not bad information.
But then we're like a lone guy in David's House.

Speaker 1 TVI, Meryl Picker. TVI, that's a good idea.
Yeah, wow. August Capital, Benchmark Capital, Shasta Capital, all in this same building.
And I think there's some space for rent in there.

Speaker 1 I don't want to go live down there, but like, I think we got to take out a lease just to

Speaker 1 collaborate on. We should just do it.
That would be for you. Fuck it.
We'll just do it. Yeah.
Yeah, we do. We'll just just do it like every year.
We induct somebody.

Speaker 1 We'll get up there, the three of us, and be like,

Speaker 1 this year we're inducting.

Speaker 1 There should totally be a Hall of Fame.

Speaker 2 We should totally do this.

Speaker 1 It fucking exists. It's hilarious.
You know, Cooperstown.

Speaker 1 There is a, what do you call it? It'd be our Cooperstown. Yeah.
There is the Computer History Museum, but

Speaker 1 it's for the PC, which is totally valid.

Speaker 1 It's not for capital allocators. It's not for people.
Like, there should be a Hall of Fame.

Speaker 2 And do we Midas List style ask people for the real hard truth numbers?

Speaker 1 No, no, no, no. It's about impact.
You have to do it. No, we decide.

Speaker 1 the three of us we decide it has to be impact on the game does the nbca have like a lifetime achievement award is that the closest thing it doesn't barely exist anymore yeah no it's it's about impact

Speaker 1 legacy like the intent of the person like this is why like paul graham would be like you know uh first ballot this is why yeah you know okay who are the who are the first ballot entrants so obvious we've already talked about it we already talked about it those are all first ballot do we have anybody who we haven't talked about or who's non-obvious but would be a first ballot

Speaker 1 this is what what I'd say. If you're under 20 years, you're not like just like, let's wait till you're 25 years in.
Yeah, just like the Sports Hall of Fames, you got to have a.

Speaker 1 Yeah, you got to be, you're not playing in the league anymore. So Paul Graham's still playing in the league.

Speaker 2 Does Jeff Bezos count?

Speaker 1 Wow, I mean, how many investments has he made? That Google investment is crazy.

Speaker 2 So there's that, but there's also, like, I think Amazon is the best venture firm of all time. Just in terms of like, it's internal.
They're not separate companies.

Speaker 1 So yes, capital allocating, lowercase C, lowercase A. They've been great at placing bets.
But you're right.

Speaker 2 Jeff Bezos is probably the most successful angel of all time.

Speaker 1 Yeah, I mean, if you just did it on the ball.

Speaker 1 Yeah. And don't put it on, you know,

Speaker 1 when you're looking at it, I think you got to look at impact. Like impact on the game, legacy.
So is Carmelo Anthony Hall of Fame? Of course he is, but he didn't win a ring.

Speaker 1 But, you know, he just, he's Carmelo Anthony, right? Like, or Charles Barkley. He didn't win a ring.

Speaker 2 Okay, so then we got like Arthur Rock. Like you got to look at like the founding father type.

Speaker 1 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

Speaker 1 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.

Speaker 1 You're generational shit right here. You know, Patrick Ewing.

Speaker 1 So I think like you look at Gurley, like he's part of that Patrick Ewing generation, right? Like that Hakeem Elijah on Charles Barkley generation.

Speaker 1 You know, you start talking about Founders Fund or YC or Angel List, like, okay, now you're talking about more modern era. Yeah.
Still going, modern era after 2000.

Speaker 1 But if you started before 2000, it's a different group.

Speaker 2 Do you notice we haven't talked about Andreessen Horowitz in this conversation?

Speaker 1 Oh, God. Who cares? No, Impact on the Game?

Speaker 1 They're in. Both of them are in, for sure.
No doubt.

Speaker 1 They totally are. I guess.
Impact on the game?

Speaker 1 I mean, I just feel like it's gratuitous. It's just like raising $10 billion, three funds a year.
I want to see what happens with the crypto stuff. I think they're just an index of venture.

Speaker 1 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.

Speaker 1 Well, I do think they have interesting ambitions, though. I think this, like...
That's the problem. It's more ambition.
It's more ambition than soulful. But there should be a J.P.

Speaker 1 Morgan or a Goldman Sachs of Silicon Valley. Should there be? For sure.
I don't know. Yeah.

Speaker 1 Why does Goldman Sachs manage the money of entrepreneurs? I just feel it's too. Okay, fine, but I just feel like it's...

Speaker 1 It's too, it's, it's like too premeditated and less soulful. I feel like it's a soulful business where like your intentionality and your relationship with the founders really matter.
It's craft.

Speaker 1 I mean, it's like the literal antithesis of of it it's the industrialization it's the intent yes it's the industrialization of it it's the it's the factorization of it and listen

Speaker 1 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 yeah it'll be mean reversion because like when you get the law of large numbers you have mean reversion exactly it'll be mean reversion for sure i mean that was at some point they leaked a lot of their returns and they were like

Speaker 1 not fair that was the 2015 well they did actually it was early so yeah that was stupid that the journalists didn't understand it but there were some older ones but it was like during that time like you start comparing it to sequoia or benchmark I think I don't think it's going to, I think in the arc, it will not be comparable to Benchmark and Sequoia.

Speaker 2 And we, I mean, made a lot of hay of the fact that they had, uh, that they made $11 billion in profit on Coinbase. And, like, which is, I do not think they sold out of that.
No, they did.

Speaker 2 So they did not make $11 billion in profit as of course.

Speaker 1 Well, I mean, it's timing is everything. We'll see.
I mean, it's interesting, too.

Speaker 1 I mean, having just done this benchmark episode, like the Benchmark Fund 7, one of, if not the best institutional size fund of all time, just like unreal. 20 to 20.

Speaker 1 Even that, like the the 500 fluctuation in the marks on that fund and it'll probably probably end up between 15 and 25x

Speaker 1 maybe but like but it fluctuates up up and down so much of course i mean it's we live in a very volatile volatile time right now so yeah i like the hall of fame idea it's kind of interesting i think we that actually would be a fun thing we should get some space on sandhill and put up no i just we could just do it as like a dinner we just literally have we don't need a year we get a yeah we get our 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.

Speaker 1 And here they are. And we just have three pictures, boom, boom, boom.
And you just drop it. And it's like, these are three people.
And then people come up and say something about the person.

Speaker 2 And I think

Speaker 2 we could do

Speaker 2 the three

Speaker 2 who we would hope would be there.

Speaker 1 And then we'll have a lot of people. We do it like

Speaker 1 where you have the person who's being inducted chooses who inducts them. Sure.

Speaker 1 Oh, that's funny. Yeah, so Rudolph does Doug or whoever does Moritz.
Yeah, yeah. John Parker does Moritz.

Speaker 1 Mike chooses who, you know. He could have Larry and Sergei.
He has Jason Calakanis come up and be like. Larry and Sergeant.
Yeah, obviously. Totally.

Speaker 1 John Dorr would ask Bezos.

Speaker 1 It's killer. It's a killer idea.
I mean, we just do Bezos, Doug and Mike. Yep.
And then...

Speaker 1 Who inducted Mario? We'd do one in Memoriam. Yes, first of all.
You would do one in Memorial.

Speaker 1 You know, whatever.

Speaker 2 Because it would be anticlimactic if the only person, because we will induct on first, and if the only person that we inducted that year wasn't a living person who could attend.

Speaker 1 Yeah, you do a combo. You do a combo.
Maybe it's four people a year.

Speaker 1 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.

Speaker 2 In order for this to like feel good, I think you're right that it has to be about impact, not about returns.

Speaker 1 No, returns is like so, that would be like saying it's like albums sold for the rock and hole full of fame. Right.
There are people.

Speaker 2 That'd be a very Andreessen Horowitz way to do it as well. That way, yeah.

Speaker 1 Andrees, but oh, what's the total assets under management? You know, and it's like, okay, dude, we get it. Yeah.
Nickelbacks sold a lot of albums. Yeah, they're the nickelback eventual.

Speaker 1 Oh, I didn't mean that. You said that you said it.

Speaker 1 I wasn't talking about the Andreessen.

Speaker 1 The Nickelback of Venice. Oh, God.
Oh, God. Like the Million Vanilla sold tons of albums.
I'm not saying that they're the Million Vanilla. No, there's like...
Oh, boy.

Speaker 1 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.

Speaker 1 Because Ron Conway, when I came into the industry, like, there was at one point, I was at

Speaker 1 the Crunchies,

Speaker 1 and Ron Conway, at one point, like, somebody said, like, hey, can everybody stand up who's had Ron Conway invest in their company? And 100 people said that.

Speaker 1 And my mind was like, oh,

Speaker 1 whoa, angel investing's cool. I mean, I wasn't an angel investor at the time.

Speaker 1 you know, long before I became a scout, but I always remember that moment when like 100 people. And that like inspired

Speaker 1 me. The scout program is a bad thing.

Speaker 1 Is that what gave you the is that what like put you in business as an angelist the scout is what put me in business yeah what happened was i had was your uber investment you personally or was that sequoya's sequoia's media yeah

Speaker 1 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 the stealthy but i mean travis knew but you know it was it was a pretty great deal you know it was like um wow you know at the time carry 50 50 50 50 at the time yeah they dropped it down after that doug meon was i bet it was like every time i'd see doug meon he's like 50 and they had 30% carry at Sequoia at that point, I think.

Speaker 1 Whereas you're, I mean, if I were you, I'd be like 50% carry to them. I can't believe it.

Speaker 1 Doug had always, they're so classy. Doug always made a joke.
We'd always make a joke. I was like, 50% carry.
Oh, God. We get 30%.
You get 50.

Speaker 1 Which is funny.

Speaker 1 We get 30. We get a lot of fun.

Speaker 1 Listen, 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.

Speaker 1 I take it very seriously, as you do for the retirees you're investing about half of, but also just think about humanity, and I don't mean to make it heady, but these companies do move the human species forward as look at Elon.

Speaker 1 Yeah, exactly. So the human species getting moved forward by, as Steve Jobs would say in those commercials, like this is the crazy ones.
They do need fuel.

Speaker 1 They, you know, maybe don't have an idea of, you know,

Speaker 1 if they should even build this company. And I think the capital allocators really come in and say, here's some fuel.

Speaker 1 Here, go fight that war.

Speaker 1 It's fuel and it's belief, too. I mean, like, what you're saying, your story about comm

Speaker 1 is not uncommon, I think, amongst founders. I mean, look at the stories about Don Valentine and Atari and other places where he was at Cisco.

Speaker 1 He's like, listen, we got to get this thing back on the rails. This thing's going to zero.

Speaker 1 There's a lot of existential moments where things go to zero.

Speaker 2 So can I ask you, as we start to

Speaker 2 drift toward the end of the episode here,

Speaker 1 that's your line. That's your favorite line.
Drift.

Speaker 1 That's the Ben's signature line. A little less here toward the end of the episode.

Speaker 1 Is that our time?

Speaker 2 Like, is this different enough from our normal show?

Speaker 1 Should we do this? I think

Speaker 1 you like this. I think a casual glass of wine and just, you know,

Speaker 1 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.

Speaker 1 You know, so if you profile somebody, like, I forgot that I had, you had done like the first episode with me and that was more about my career and more details.

Speaker 1 And so I'm starting to tell stories over again. It's like, well, let's talk about some other stuff, right? Yeah.
So I think it's like

Speaker 2 our audience was one type of society.

Speaker 1 I like this format. Well, part of what we, you know, like Lex has done so great with his show.
Yeah. But those types of conversations, but I feel like that's more,

Speaker 1 what's the right word?

Speaker 1 Our shows are about the business of tech. Yeah, no, his is intellectually.
It's not about that. I don't know why he's in the tech vertebrae, but I like the format.

Speaker 1 And like Kevin Rose used to do with the Foundation series and like.

Speaker 1 Yeah, I mean, long-form interviews, like Howard. I mean, I think Joe Rogan stole it from Howard, and I think it's now Lex stole it from Joe, or I don't want to even say stole, I think,

Speaker 1 you know, inspired by. 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?

Speaker 1 He was very enamored with Stern.

Speaker 1 And he wanted to be Stern, I think, and he eventually has supplanted Stern in a way. Indeed, did become Stern.
Yeah, it did become Stern. And so good on him, yeah.

Speaker 1 Right down to the Sirius, Spotify, like right down to it. He became

Speaker 1 a platform dealer. Yeah, doing a platform.
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.

Speaker 1 built the platform. He used his number one show to build their platform, right? Which is, I think, what, yeah, which but actually to bring it all the way full circle back to Charlie Rose.

Speaker 1 Like, yeah, he was like a, you know, business. I mean, he did more than business, but like he would have.

Speaker 1 Culture, business, anybody in New York, because New York, everybody in New York was pretty fucking interesting. So

Speaker 1 he could have somebody from Wall Street, a publisher, an author,

Speaker 1 somebody who does films, you know. He would have like Spike Lee on it.
You know, he'd have Woody Allen on.

Speaker 1 He would have, you know, any actress on who was doing something interesting, any novelist, Margaret Atwood, anybody was just coming through New York on a press tour.

Speaker 1 You know, you, you would do your press tour, and then you would just go chill with Charlie, and you would get to do something long for him. Yeah.

Speaker 1 It was like a little

Speaker 1 more jazzy, you know, a little bit more like acoustic. So I like this format for you guys.

Speaker 2 Did you listen to Smartlist at all? Do you know about that show?

Speaker 1 I have listened to one or two episodes. It's Bateman, Will Arnett, Arnett, and then somebody else.

Speaker 2 Yeah, the guy from Will and Grace, Sean.

Speaker 1 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.

Speaker 2 and it's like it's like it's like katy perry it's like chris pratt yeah it's become a big deal i kind of want to do that of tech but like

Speaker 1 wait you and i don't know who the one of us is bringing you from you guys are not good you can't make you got to know the person's background much better but there's a celebrity carry a certain charisma with them that our entry doesn't have

Speaker 2 but maybe it doesn't have to be the surprise as much as like

Speaker 1 well that the other thing is that it's even though they have guests the show is actually about them the guest is a prop in a way Yeah, I guess I've only listened to one or two you know I see it in the rankings like it does incredibly well like it's a top 10 or top 25 podcast is it part of a network?

Speaker 1 Is it part of Spotify or something? I don't think so because I see it on iTunes very often. I think so

Speaker 1 it's really weird that like Spotify doesn't allow Joe Rogan and Call Her Daddy on iTunes because

Speaker 1 The advertising would be huge. Right.

Speaker 1 So why not take the ads in and put them over there.

Speaker 2 There's some NBA that's run the numbers that says it's more valuable if it's driving new subscribers to spot.

Speaker 1 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 music.
So they're doing audiobooks too now.

Speaker 1 That's the next piece. Yeah, that is the next piece.
Yeah, they're doing the audio books, one-off purchases. Smart.
I mean, audio is great.

Speaker 1 It's getting really hot in here. It's getting really hot.
We got

Speaker 1 hot. For those of you who don't know, we're in like a sauna.
A new,

Speaker 1 yeah, David's new house. David just moved.
David's got a new empty house.

Speaker 1 There's no way to do it. It's

Speaker 1 It's sort of like the shining.

Speaker 2 There's no furniture. We just

Speaker 1 literally

Speaker 1 literally in the last like two days. That explains the smell.
All right. You could have, I mean, listen, you're rich, dude.
Just go on. Oh, buy some crane barrel.

Speaker 2 We can't all be Jason Calicadas.

Speaker 1 No, come on, man. I know those fees.
Oh, my God. I've had ravens.
Craigslist, I love Craigslist. I love it.
You buy used furniture on Craigslist. All the time.
I do not buy any furniture.

Speaker 1 All right, that's kind of stuff. I bought a temporary couch on Craigslist.

Speaker 1 It was was not going to be a good thing. No, no, no.
You're going to get robbed. Don't do that.
It's too crazy. Craig Newmark, I love you, but

Speaker 1 with that. With that.
Our thank you to Vanta. Oh, Vanta.com/slash

Speaker 1 acquired.

Speaker 1 Oh,

Speaker 1 Vanta.com slash acquired.

Speaker 2 Our thank you also.

Speaker 2 You don't know who the other sponsors are because we haven't talked about them live with you because we felt very strongly that it was, you know, we wanted to make better use of your time.

Speaker 1 I love reading the angle.

Speaker 2 Can I make a video? Do you want to read our Brex ad?

Speaker 1 They don't sponsor my pods. I know.

Speaker 1 Maybe they have. I don't know.
There's also a lot of adults. I'm not sure if you're talking about Brexit.
Brex, yeah, yeah.

Speaker 1 I know there's people who use Brex. I think we use Brex.
It is one of my companies.

Speaker 2 If you're enterprise, if you're global, by far the best corporate spend management.

Speaker 1 It's much more than a card now. Much more clear.
Yeah, for expenses and everything like that, right? And then they've kind of expanded behind that. So you can give cards to each of your employees.

Speaker 1 Then if they screw up, you can turn it off or something. Yes, exactly.

Speaker 2 Pre-approve some budgets.

Speaker 1 Yeah, you don't want people to jump on the fence and going crazy.

Speaker 2 All the listeners know because they heard it like an hour ago.

Speaker 1 They're very familiar. Oh, it's in here, yeah.
So anyway, thanks for shout out Brex. So that's Brex.

Speaker 2 Shout out Brex. And then use the promo code twist.

Speaker 2 We share this last sponsor.

Speaker 1 These are great folks, Keith.

Speaker 2 These are like dear friends and geniuses and rack contours.

Speaker 1 Masterworks? No, no, no.

Speaker 2 Think smaller, but bigger.

Speaker 1 Smaller, bigger. Literally small.

Speaker 1 Gotcha, Kelly. But secretly huge.
Tiny. Oh, tiny, of course.
Yes. They're buying companies.

Speaker 2 They're buying companies.

Speaker 1 They're doing a good job. Yes, they're creating like the Berkshire of

Speaker 2 the Internet. And can you imagine a better time to get the monkey off your back of venture capital and sell your company?

Speaker 1 Secure the bag. Listen to the company.
Secure the bag.

Speaker 1 Let's have a favorite takeout live. Secure the bag.

Speaker 1 Let's go, man. Trust me, if you haven't secured the bag yet, it's a wonderful experience, man.
It's not like getting home with the bag. You get that tiny bag.

Speaker 1 Oh, man. Let me tell you something.

Speaker 1 I'll tell you the story. What did you do when you secured the bag? I'll tell you what happened.

Speaker 1 It's a funny story. I'm in my office, and I got Bank of America, and I got like

Speaker 1 low thousands of dollars in my Bank of America. And I got an American Express card with negative 10 on it, and a Visa with negative 5 or 10 on it.

Speaker 1 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.

Speaker 1 on the thing. This is

Speaker 1 refreshed.

Speaker 1 I'm hitting refresh. I'm hitting refresh.

Speaker 1 And then bing, bing, bing, bing, bing. You know, all the numbers come in for the whole, you know, amount.

Speaker 2 And you own most of weblogs, April.

Speaker 1 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.

Speaker 1 Oh, wow. Yeah.

Speaker 1 Or more, maybe I own 10%. I think I own 10%.
Anyway, long story short,

Speaker 1 my wife comes in. She said, you okay? And I said, what? She said, are you crying?

Speaker 1 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

Speaker 1 she said, why are you crying? And I said, I'll never, my family will never have to worry about money again.

Speaker 1 Because I spent my whole life worrying about money.

Speaker 1 You know, my dad had lost the business. It was a very cathartic thing for me.
And I think people, you know, who are already rich,

Speaker 1 or maybe who come from means, just they don't understand the concept of living with the fear of being broke and in debt all the time. And then, when you have the bag, you secure that tiny bag.

Speaker 1 And it's a tiny bag,

Speaker 1 but it's filled with diamonds. And gosh, you just open it up and say, Thank you, Tiny.

Speaker 1 Thank you, Tiny, for securing that bag. Acquired.fm slash tiny.
No, it's tiny. They don't give us a thing.

Speaker 1 They don't really know what it is.

Speaker 1 Tiny will help you secure the bag. Is it hiat

Speaker 2 and tell them Ben David?

Speaker 1 Whatever it is. Just know that tiny.
Tell them that Ben David.

Speaker 1 You can imagine, Jason. Yeah.

Speaker 1 I did buy a One Touch Espresso machine. I bought a Jura One Touch Espresso machine, which at the time was like two grand.
And I was like, this is unbelievable.

Speaker 1 Then I tried to buy a Ferrari. Oh,

Speaker 1 they wouldn't sell it to me in Beverly Hills.

Speaker 2 You were the reframed? No new money or something?

Speaker 1 What's the matter? Yeah, basically. I went in there and they're like, oh, yeah.

Speaker 1 I'd like to buy a Ferrari today, the 4.30. 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.

Speaker 1 So I said to this guy, can I ask, what do you do here?

Speaker 1 He's like, we sell Ferraris. I'm like, to who?

Speaker 1 This is actually, 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 a business.

Speaker 1 We're not putting any point in your list. I was like, well, how long is the wait list? He's like,

Speaker 1 don't even bother getting off. I was like, okay.
I was like, I'm a cash buyer. He's like, everybody's a cash buyer.
I'm like, okay.

Speaker 1 Can I ask you a question then? He's like, sure. Come into my office.
We're like an espresso. You want some Pellegrina? I was like, no, I'm good.
You want some Pellegrino?

Speaker 1 Like, literally, you want me to Pellegrino and espresso. And I was like, I was like, I have the same one touch.
Sure.

Speaker 1 And this Italian guy is like,

Speaker 1 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 cards, pre-owned, certified. For more.

Speaker 1 And I was like, oh, I was like, well, I would take a pre-owned one. He's like, oh, well, the one you're looking at is pre-owned.
I was like, no, no, no.

Speaker 1 The one I'm looking at, the 4-30, the red one out there, that's the one I want. That's got a sticker in the window.
He's like, yeah, yeah. We certify them.
We put the sticker on the window.

Speaker 1 I was like, oh, well that goes for two hundred thirty thousand dollars or whatever and so uh yeah what do you want for it he's like 300

Speaker 1 and i was like you're like the sticker says no no no this is the potential

Speaker 1 i said the used one i was looking at he's like yeah you can't get these cars and i was like ah

Speaker 1 so you pay over 70 000 he's like but it only has two thousand miles on it and i was like two thousand miles It's 70,000 more than new. I said, why wouldn't I buy a new?

Speaker 1 He said, because you can't get them.

Speaker 1 And I just, I'm such an idiot from Brooklyn who doesn't understand the concept that people would pay over for the car. And I'm just perplexed.

Speaker 2 That would bother me.

Speaker 1 I was like, all right, well, let me think about it. I left.
And then I was with my friend, and I was like,

Speaker 1 and I had the Rob report, and it said, like, number one car was the Ferrari F30. And the turn of the page was Corvette.
C6 was the number two car.

Speaker 1 And the starting line was, make Ferrari buy two for half the price of a Ferrari and beat them off the line. Or something like that.
And I was like, let's go to the Corvette.

Speaker 1 Let's go to the Chevy Store. Let's go to the Chevy's store.
I walk in. There's Corvettes everywhere the guy looks at me he goes you want to buy a Corvette I said yeah

Speaker 1 he said you buy a Corvette today I'll give you five thousand dollars off I was like yeah so we go out on the 405 and we're driving the Corvette and he's like this is a Corvette son like you're going 70 miles an hour I'm not selling I said I'm not he says I'm not selling this car to you unless you hit that gas much harder and I said okay and I punch it to 100 miles per hour.

Speaker 1 The guy's like, yeah, how does that feel? I'm like, great.

Speaker 1 That guy's good. I come home with the

Speaker 1 i come home with a yellow convertible corvette my wife's like what happened to the ferrari i was like this thing only costs 65 grand it's like 70 and i got five grand and it's american baby and it's american and uh that was the car that i famously uh

Speaker 1 was according to gawker Robert Scob and 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

Speaker 1 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

Speaker 1 the Corvette. And I was like, I'm doing something wrong.
And then we switched cars and we and I was like, nope, electric's just going to beat everything. And this was the first one

Speaker 1 that, you know, first that was the one. It's the one, the prototype.
That's in space right now. It's the cherry red one.

Speaker 1 That's the one that's in the space. And there's a famous photo of me and Elon in front of the

Speaker 1 That one's it, but there's a famous photo of the two of us

Speaker 1 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.
Robert Scobe was recording this on his Nokia, you know,

Speaker 1 smart.

Speaker 2 These are the memories, right? Like, this is the journey that you've been on. Yeah, it's pretty cool.
This is the stuff you just will cherish forever.

Speaker 1 My life is unbelievable. I am so grateful for it.
And thanks for having me on the pod, guys.

Speaker 2 Listeners, thank you so much. Acquired.fm slash Slack.
Come join us. We'd love your feedback.
This is a good thing.

Speaker 1 Slack's cool. This is a new shtick.

Speaker 2 Acquired.fm slash store.

Speaker 1 You can buy cool shirts.

Speaker 1 Schwag.

Speaker 2 Slash jobs. Find your next work in your experience.

Speaker 2 You've got a bunch of new ones. That's right.
Acquired.fm slash David buys you some smelly furniture. My God, it is hot in here.
All right, we got some.

Speaker 1 Let's go eat some food. Let's you share Mexican.
I don't know what we're going for here.

Speaker 1 Oh, so fun. Thank you so much.
Of course.

Speaker 2 All right, listeners, we hope you enjoyed that very first Acquired Sessions with Jason Calicanis. It's a new format we're playing with.
We would love your thoughts.

Speaker 2 Acquired FM at gmail.com or tweet at us at acquired FM.

Speaker 2 And with that, listeners, we'll see you next time.

Speaker 1 We'll see you next time.