ACQ Sessions: Jason Calacanis

ACQ Sessions: Jason Calacanis

October 04, 2022 2h 29m

We kick off ACQ Sessions with the-behind-the-scenes story of All-in, from the world’s greatest moderator himself Jason Calacanis. ACQ Sessions is our new, occasional “MTV Unplugged” version of Acquired: a great IRL guest, a bottle (or two) of wine, and no script. We talk about everything you’d imagine we would over wine with JCal — All-In, bestie relationships, money & politics in Silicon Valley, who his influences and mentors have been (one surprise — the great Fred Wilson of USV!), what motivates him to keep grinding and why, at age 50+ when he could easily be winding down he’s instead speeding up into the most productive phase of his entire career. Pour a beverage yourself, pull up a comfy seat and join us! 

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Full Transcript

so wait it was a magazine magazine yeah magazines was like the original platform for wait are we start have we started silicon alley i guess this is the trick we've just been recording the whole time yeah welcome to quiet sessions all that stuff that you said beforehand that like is really juicy i don't think we should put that no definitely not definitely not we don't I want to tell people where their bodies are buried.

Well, cheer. all the time yeah welcome to acquired sessions all that stuff that you said beforehand that like is really juicy i don't think we should put that no definitely not definitely not we don't want to tell people where the bodies are buried well cheers boys here we go where this is the is this the first one or this is the first in real life but i think this is our ninth tenth together something like that a lot between the two pods yeah for sure great to know you boys so this is the first acquired sessions acquired sessions i feel like i should get out on guitar here and just play some dylan this is this is your baby what is acquired sessions acquired sessions is normally on the show we are like so scripted yeah you are and we have a great time we do four hour episodes you know it's awesome but uh really for folks like you who we know really well yeah what happens if we throw out the script? And just chop it up.
And we just chop it up. David Rosenthal unplugged.
Wow. I love it.
I love it. This is the literally MTV unplugged.
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That's great. So, well, we have no agenda, obviously.
No, no. Wait.
Where do you want to start? We We got to think Vanta. Oh, yes.

Oh, Vanta, I'm an investor. We're investors too.
Well, great. They're an awesome company.
Big supporter of podcasts. So yeah, go Vanta.
We are huge fans of Vanta and their approach to the whole compliance process, SOC2, HIPAA, GDPR, and more. And we've got CEO and co-founder Christina Cassioppo back with us today.
Vanta was already the best place to check the box and get security compliance certified. But now you've just launched Vanta Trust Reports, which take things even further.
Tell us about that and how they can help companies deepen their relationships and trust with their customers and partners over time. Really excited about these.
Actually, a bit of not yet told Vanta history, but something like Vanta Trust Reports, honestly, a much worse, much more poorly designed version, but yours truly, which is why I can say that, were launched in the very early days of Vanta when we wanted to help companies get secure and prove that security, but weren't yet convinced we wanted to or had to go all through the nuances of what a SOC 2 was. So we figured, hey, let's just make this report of the best security practices.
Let's check companies against those practices all the time and make this live and updating visible and transparent. This should help these companies prove their security and grow their business.
And it should also help them be more secure because they've got this report, like this kind of security status page out in the wild. So 2017, Vanta tried this and found out that no one really knew what a Vanta report was and everyone wanted a SOC 2.
So flash forward to 2022, and it's actually really exciting. Turns out creating standards is, you know, people have to know who you are before you can create your own standard.
A little bit, you know, and so honestly, like, I mean, I'm joking, but I'm not like literally the company strategy on that day sort of became, okay, use the existing standards to bolster yourself and build something better here. And so this launch of trust reports is really exciting.
These are companies that maybe it's before they've gotten a compliance certification, maybe in their process of getting one. For some, actually, they already have one, but then rather than keep going through their buyer's process, they're like, look, this is just constantly up to date and has all the information you need.
You know, take a look at this instead, rather than my, you know, compliance PDF from months ago. So relative to a SOC 2, which is done once a year and kept up to date annually, a Vanta trust report is kept up to date to the minute, basically, continuously.
You always know what the company's practices are. So just really excited to get this out into the world and into folks' hands.
Our thanks to Vanta, the leader in automated security and compliance software. If you are looking to join Vanta's 2000, nay, 3,000 customers to get compliance certified in weeks instead of months, you can click the link in the show notes or go to vanta.com slash acquired for a 10 discount thank you vanta so in the juicy stuff earlier you mentioned mahalo yeah i don't know is that why you started can we just keep like referring to the juicy stuff yeah the juicy stuff yeah no we want to talk about that stuff yeah is mahalo why you started you went from print to print to Well, in the 90s, you know, I grew up in Brooklyn.

My dad... started you went from print to print to well when i in the 90s um you know i grew up in brooklyn um my dad had his bar uh seized by the feds because he didn't pay his taxes during the 1987 crash he became like he got behind and the fed showed up one day and this was the maybe six weeks before I was set to go to college and he said hey son i can't help you with college good luck uh and uh i might be going to jail so take care of your mom so he was like really behind on his taxes and you know state liquor authority they kind of take it serious so feds come shotguns the whole thing they seize the everything in it.
And I was like, well, I guess I'm going to school at night. And I'm going to work during the day.
And I worked fixing laser printers. And that was like a really good racket.
The HP had just come out. Were you set to go to college somewhere else? Well, that's another story.
But I was set to go to Brooklyn College. I got into that.
I had also taken the police exam to be a police officer. So my brother went into the force.
And then I said, you know what? I'm going to see if I can go to college and make that work. So I'm going to go to Brooklyn College.
So I decided to work during the day. And then I went to school four nights a week, 6 to 9 p.m.
Carried full credits, 16 credits a semester. And I would work fixing laser printers all day.
I was a bad student. I was always that student who underperformed.
I didn't find great meaning in academics, but I had a computer when I was in high school and I was more interested in playing with my 300 baud modem, which then became a 1200 baud modem and my PC junior. So it kind of, you know, like many people of that era, we were sort of set on a path because we were the first generation to have a computer at home i actually had an atari 2600 and it could play tank was the game that came with it and pong and so my dad bought this for us when i was six or seven years old 1976 1977 and he had one of the first pongs in brooklyn in his bar so he must have cleaned up on that oh my god it was.
It was crazy. And so I just got exposure to video games and computers.

And I was like, wow, this is incredible.

Computers are going to change everything.

And then I happened to hack some software.

We used to run a lot of scams.

You told us about the VHS.

So VHS, Jason's Hot Tapes was technically my first business.

But there was a side job I had, which was cracking software. So we would make copies of Chess Master and stuff like that, and then sell them for $10.
And then we started hacking and doing what was called phone freakings. When you were doing this stuff, you'd be reasonably technical to do it.
Not like Wozniak technical, but like... We soldered chips sometimes.
We changed... Yeah.
To put memory in at that time you had to like take the memory chips and put them in and then bend them over and stick them in did you ever think about like did you consciously ever make a fork where you were like not tech media and of course media about tech but you're like i'm not gonna be the guy doing the boards i'm gonna be the guy writing about people doing the boards. It's a very good question.
I used to go to Bleecker Street. I used to hang out in the West Village or the East Village.
It was like the cool places to hang out. And like a thing to do would be to go to Tower Records and look at the zine section.
So there was a concept of a zine, which was short for magazine. But a zine was something you wrote with your friends.
You printed it yourself at a photocopy store. It's like blogs before blogs.
Blogs before blogs. And I created a zine.
I was like, I'm going to be a magazine publisher. So the first one I did was Cyber Surfer, which was about dial-up services and CD-ROMs.
And I did it with my friend Brian Alvey, whom you might have heard of in my career. We went to high school together.
Weblogs? We did weblogs together. Yeah, so but in the early 90s, I did it with my friend, Brian Alvey, whom you might have heard of in my career.
We went to high school together. You did weblogs? We did weblogs together.
Yeah. But in the early 90s, I did.
Which is Engadget, Twad. All that stuff.
Everything you sold to AOL. I think I sold to AOL.
But anyway, before that, I did that magazine. And then I met Jerry Colonna at Internet World, the first one.
And there was a booth. That's right.
When Jerry was a VC before he was like the whisperer of startup coaches. He was consulting for Lycos and I think CNGI.
And so there was a Lycos booth. And I had met this young lady at it.
And we hit it off. And we're talking.
And then she introduced me to Jerry Colonna. And then I met Jerry Colonna in an office no bigger than this room in Union Square.
And he said, listen, I'm leaving Lycos, but I'm going to start this Hack Me Ventures with my friend Fred. I want you to come read business plans for us.
And so I met Fred Wilson, and I would go up to them, and they were doing, J.P. Morgan was going to back them for their venture firm.
This was 1994, 1995. This became Flatiron.
It became Flatiron. J.P.
Morgan was the first big anchor of Flatiron? They were half of it. And Masayoshi-san SoftBank was the other half.
No way. So they wanted you to come be a VC associate.
Not a VC. Just to read business plans.
So the deal was they would take me for sushi and pay me $1,000. Wait, what do VC associates do besides just read business plans? Exactly.
Well, anyway, it was the thing. And so I had the magazine story at Silicon Island Reporter.
And they were paying me. And so I read about this Beverly Hills internet company, which got rebranded as GeoCities.
And I wrote a little coverage of it, and I said, you should invest. I'm 24 years old.
I don't even know what PC is. That's where Flatiron made all their money.
Yeah. They were going to invest anyway.
Flatiron became USV, right? Yeah. Flatiron went with Jerry Colonna.
Then when Jerry decided he wanted to move to Colorado and just chill, he had made enough money, I think. Coach Found.
Coach founders, I think. And yeah, maybe he had like, I think he's been pretty public about it.
Like, I don't want to say a nervous breakdown, but a kind of like maybe a fork in the road. Like making a decision about what you want in your life kind of situation.
He wrote that great book about it. Yeah, yeah, yeah.
And so Jerry was a good mentor. But Fred actually became ultimately my deep mentor at that time.
And Fred said to said to me listen you're doing silicon on a reporter you're writing about us and the companies we're investing in and um you're doing stuff which would you rather do and i was like i think i'll do the magazine uh this was before now it's like i do both and now it's like i do both why choose but just to back up to dio cities that sold to yahoo for like five billion and i think four or five was the main investor yeah flat iron maybe owned five or ten percent of it it was like a huge win for them i mean fred was on fire for a new york vc and jerry they did pretty well they had how did that happen right like i mean silicon valley was here but they were in new york like what was going on yeah we just there was a lot of good companies brewing in new york and my concept with silicon i reporter was well they have red herring in the bay outside in the bay but i own new york and i had silicon reporter and then i started one called digital coast reporter in la so i had two magazines two conferences two email newsletters that's kind of king of new york right i grew that business to 10 million dollars in revenue off my credit cards um and um had a 75 to 100 people working for me when i was 27 years old. And I didn't know anything about how to run a magazine, how to run Edsels.
I taught myself everything. What did your family think of this? It was pretty heady stuff because I wound up being on the cover of the New York Times on Charlie Rose.
And they wrote a feature story about me for 8,000 words in the New Yorker. So anyway, it's a really cool time in New York because at that time time you were either in media or finance or art publishing it was like a finite set and i was in publishing but i was also in this new thing technology and so everybody wanted in on that it would be like the equivalent of crypto is today like at its peak where like and you were the equivalent of like satoshi or something like it was crazy to be the New York internet guy.
Can I? So we talked about a lot of this when we did our big Empire of Jason Calacanis episode with you. So I want to put this on pause.
Yeah, sure. People can go listen to that.
You should. It's great.
We get the detailed story of Weblogs, Inc. and all that great stuff.
you mentioned, I want to like take us from you're only as good as the, you know, your greatest, your newest thing. Sure.
Because the last time we talked to you, you were just starting all in. It's hilarious.
And like, can we talk podcasting? Of course. I love it.
Podcasting is like, I think perhaps my greatest medium. What happened with all in? How did, I mean, it's weird.
Has it surpassed your wildest expectations? I thought it would be something Chamath and I would do 10 times. Yeah.
So the origin story is pretty simple. Chamath, I knew because he was running ICQ.
Chamath was running ICQ? At AOL. And I had sold my company, AOL.
And the revolving door of AOL. I didn't know that was the lineage.
It was like Ted Leonsis had this March to a Billion. My Greek brother, a mentor, had this March to a Billion off-site.
And so I went to this, and I just sold Weblogs Inc. Like a million AOL users? Hot shit.
That's idea was that well with weblogs inc and with uh aol and other assets they wanted to buy they were going to march to a billion users yeah it was like this crazy rallying car and we had these t-shirts march to a billion so i go to that and i see 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 said what are you doing here he's like i'm running icq into the ground you know i'm just writing it down every month it loses a million members it's hilarious and he's like yeah but i'm leaving i'm gonna go um i'm gonna go to the west coast i'm gonna go work at this vc or whatever it's all right nice seeing you um and so then when he was there i was in la uh and what vc did he go work because he was at facebook mayfield mayfield for a year and then sean parker him to Zuck and Zuck needed you know like a Chamath he needed like somebody who would just Chamath built the growth he built the growth team and he was like I don't there is no equivalent of growth that was the idea of growth hacking didn't exist as a term until Chamath did what he did. He said, just find me the smartest people.

I'm hiring based on IQ.

And I'm hiring based on desire to make a lot of money and be a beast.

And he just went, he went into beast mode because, you know, he too was very hungry.

And he was like.

But you guys must have been like brothers from another month.

Yeah, for sure.

For sure.

We're, we're, we're definitely, you know, both outsiders in Silicon Valley.

And, you know, I had Chamath come on the pod this week in startups, that is.

We listened to it.

It was, it's fun to go.

Thank you. Definitely, you know, both outsiders in Silicon Valley.
And, you know, I had Chamath come on the pod, this week in startups, that is. We listened to it.
It's fun to go back to that moment. The first one.
And, you know, you can see how he's not, you know, polished. He's not Chamath, you know, as gregarious or whatever.
He's a little more reserved. He doesn't have the Laura on.
No Laura Piano. Was he in great shape or? No.
No. Not one of the teachers.
He was like a dork you know like he but he was this is bezos pre uh yeah whatever you know he he always was a poker player he was playing atlantic city so he was you know like myself an outsider who wanted to take risk and wanted to win and um you know confident you know even maybe more confident than both of us should be. And so I kind of introduced Shemoth to the world by convincing him to come on the pod, which he was like reluctant to do when he was on Facebook, but he did it after Facebook.
So I kept asking him to come. He finally was in LA.
He came on the pod. And then people, I was like, he's really good on stage.
Like he's funny, whatever. whatever and so which at this point you had an eye for because you're like of course I mean one of the things when I was a podcaster in those early days you know talking about 12 years ago whatever is you know I introduced a lot I think like 14 right 14 yeah I introduced people to the world yeah uh yeah it was 2008 I guess whatever so I introduced a lot of people who were in tech to the you know know, and it was only a couple thousand people.
And then as now, too, like you could be a great founder, you could be a great person in tech. But like that doesn't automatically make you a compelling guest, as we know.
No, of course not. No, I mean, I have my own theories about what makes for a great guest.
We'll put that on the side for now. But anyway, we start a friendship.
We start playing cards we start hanging out you know trading notes kind of thing and uh he's gonna start his venture firm i'm a scout at sequoia all that stuff we start playing and trading notes and we just become great friends but then he was coming out of cnbc one day and he's like oh my god you know just like we have such a good rapport when you interview me because he had done a bunch of interviews with me on stage and stuff like that on my events he's like i want to do a podcast with you i was like yeah you can come on this week and start up any time it's twice a week now and which it's now five times a week six six plus i'll see i'm gonna go i may go back down to five next year it's a little much right now yeah dude you i mean we'll come back to this but you're killing yourself right now and you're on act three yeah i have more energy now than i i may i may have i i just this like coming out of the pandemic might have as much energy as i did when i was in my 20s but for different reasons different type of energy um anyway chumov calls me you know coming out of the studio i don't know if it was in he was in new york or was he was in the one market one in san francisco here but um he said i want to do this pod with you i said okay and he said i want to do a new pot with you just me and you we talk i was like sure he's like what should we call it we're texting back and forth i was like we should call it all this is 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 you'd been referring to this poker game on air on 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 then chamath had a poker game sax i had hosted it floating and putting all that together um yeah i'd refer to it many times in the pod but try to you know keep it from becoming public right but it was me bill gurley it's all public now mark pinkness right or maybe i think it used to come to the code one yeah um which is another funny story um and uh lots of funny stories in my life but anyway um so then the pandemic happens and we're like where are you going just dropping these little breadcrumbs got to pick them up on the way. At some point, we got to pick these up.
Anyway, at some point, I'll write a biography. Anyway, nine years.
Third book. Anyway, then the pandemic starts to happen.
We're like, well, Saks has some ideas about masks and then Friedberg. Saks and Friedberg weren't.
there was no besties originally, right? No, no. It was just you and Chamath.
And in truth, like, Freiburg and I weren't besties before All In. I mean, we knew each other.
We were friends, but not besties. I was besties with Sax and Chamath, and now Freiburg is a bestie.
But he played in the game, obviously, and we had just started to have a developer friendship, but anyway, that foursome kind of clicked, right? Pretty quickly. Um, and I think, you know, I was a really good interviewer.
I'd studied interview techniques and really, you know, after doing whatever I'd done at least a thousand episodes of twist at that point. And I had had sacks on many times and Chamath.
So I was them and at the poker game we break chops and i make jokes um and chamath's a great host and just very comfortable with each other uh and and freeberg kind of joined that group and um it clicked and i think during the pandemic and i i thought maybe this last 10 20 episodes but during the pandemic i think people wanted information and i realized in perspective i mean i think that's a thing i'll tell you i never expected to be listening to david sacks talk coming from where he comes from politically and where i come from politically and going yeah that is a good point and that perspective is like so helpful in our polarized world today yeah it's very unique and you know around the poker table we all listen to each other we're friends but the world does not want us to be friends in some ways the world wants us to be enemies and i kind of think about it like um you know best of enemies kind of situation like we debate specific things like uh gore vidal and um

who is this adversary uh anyway it's a great documentary about gore vidal and um who's gore william f buckley they're just two public intellectuals one was on the left one was on the right and there's this documentary best of enemies in the 60s they started debating like uh different political conventions and it was like the most compelling thing on tv But they were like friends.

Best of enemies.

They weren't besties like Saxon and I are. But, you know, Gourvidal was just, he was gay.
Kind of closeted or quietly gay. And on the left, and Buckley was like a serious conservative.
And they went to blows sometimes on the show. Like, at one point Buck buckley i think he called him like a sissy or something like really like derogatory as a gay man and the world didn't understand he was exactly gay it was like sort of time period in the 60s where like maybe some adults understood like yeah that's a gay man but we don't say that's when they got into town yesterday we were driving the castros right nearby and we saw a naked guy in the castro and I I was like, aw, a naked guy in the Castro's.
Ben was like, what is going to do? You've got to understand. No, the public nudity is a thing.
It was a huge, jacked dude walking around, and super sunny, so he was just all slick down. But did he have his shoes on? Was he wearing combat boots? They usually wear boots.
And then they usually carry a sarong. There was a big debate when I first moved up here because there was a number of folks who used to like to get a Starbucks.
And they had to like negotiate. And they were like, how about a sarong in Starbucks? Because you're going to sit.
Right. Right.
Bare ass. And for context, I've explained this to Ben.
But like this is a thing in the Castro in San Francisco. It's a cult.
It's like a. It's a very accepting place.
And it's like, ah, this is like a relic of the 60s 70s it actually was pretty awesome because david we're like driving up and david goes oh a naked guy it was the most like warm hearty 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 and here it means like like high fives and right ons. But, you know, growing up in New York, like if somebody takes their clothes off on a public transportation or in a cafe, like people are getting a baseball bat and calling the police and like the shit's about to go down.
Oh my gosh. You know, and then here it's like, you know, high five and live your life.
That's one of the things I love about San Francisco. But anyway, the pod's gotten very big.
So you get the gang together and like, why do you think it works? Why do you think it works? It's like the number one-ish tech or business podcast. In our business, it's number one, of course.
But it was number 28 last week in the world on iTunes. You guys have transcended.
Like, this is more than just- It has nothing to do with tech anymore. Yeah.
It has nothing to do with finance or tech anymore it is it works tipped over into colleges i was at i was you know skiing in tahoe and i you know i was with my kids and it's hard to get a table type situation i was like hey i hate to be a pest but i see you're wrapping up are you and no pressure but are you going to be leaving soon because i'd love to camp out here and get your and they're like stop busting my balls and the woman looked at me and she goes jacal and i was like oh have we met and she's like no i listened to your pod twice a week i'm like it's only on one she's like i listened to it twice and i was like oh my god that's so nice she's like i was like are you in the industry she's like i'm a dentist wow reno and i'm like you're a dentist in reno's can i ask how you found out about she's like i don't know like she's like i deeply care about san francisco politics no it's not how she had found it and this is you know during the pandemic situation then that's when i realized that it crossed over was there a moment for you either you for or you where you were like whoa this is you know i've been um micro famous you know micro celebrity multiple times in my career but this is yeah not for me you know and i got a lot of famousamous, you know, micro-celebrity multiple times in my career. But this is different.
Eh, not for me, you know. And I got a lot of famous friends.
You know, I'm used to getting recognized. I'm used to people taking pictures.
What I'll say is, like, where it used to be, you know, if I go to Austin or New York, people would say, I would have three people stop me on the street a day if I was walking around in New York. Now it's 20, you know, or 10.
And they want to take a selfie. And it's, you know, it's just, you know how podcasting is.
You guys get recognized. And it creates a level of intimacy with people.
Oh, for sure. If they're in the habit.
Yes. Because you're hearing people every week.
And then people become characters. And I tried to make everybody, I was, you know, in all honesty.
You mean people on the show or people in the audience? 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 this but i crafted some character kind of arcs i the fights are all real trust me there's nothing scripted about that but i did say like i think i can as the point guard here kind of shape the conversation and i literally created the character of the sultan of science right that's what i was gonna say and you know freeberg didn't even have a twitter handle well there's zero followers there's even a character of jcal on all in like there's how the world's greatest moderator sure yeah i think J. Cal, the guy who lets himself be the punching bag because it plays for the show.
A little bit. Which is part of the world's great.
If I'm being honest, I'd rather not be the punching bag. They're like, you're the poorest guy on the show.
I'm like, do we need to point that out so often, guys? You're like, not by much. I'm feeling really good about myself.
You don't have to point out that you all have more money than me and you two of you have planes and I don't

it's okay with me, I could have a plane, I guess

I could get one, but

you care about the environment

well no, it's also like I don't want to waste a ton of money

whatever reason

but you do let yourself play that role

you have been enormously successful

and you sort of let the role of J. Cal on the show

be like that guy who one day wants to be like us maybe he'll maybe he'll make it i actually never wanted to play that actually no that was not that was just the boys breaking my chops maybe so maybe it's a little bit of like them wanting to uh you know maybe uh take the piss out of me a little bit which is fine because you know i give it as good as i can get it but i think that's probably for them you can ask them when they're on the pod i think for them that's kind of the diss that's the one they can easily go to is i'm the poorest guy on the show but like i've done okay like what i maybe let's flip it like for them before all in i mean tamath had a little bit of a public

no they were not famous they had no go to mark they're all they're all this is a new thing for each of them to hit this level of notoriety it's not for me what do you think for i mean we should ask them this sure like if you were to speculate caveat that it's speculation what do you think for them all in has like done like well i mean for friedberg nobody knew who he was except if you worked at google or you were in vc like he's very connected in those circles what's that or monsanto or monsanto like he's very connected in those circles but he was kind of under the radar guy um i think really by design he didn't have any desire to so i think it's probably the biggest adjustment for him the the increase in profile has certainly been the highest for him and he's loved there was a moment when i like jokingly said to people during the q a session at all in summit uh you know just say who your favorite bestie is and then direct question and it was like five in a row sultan of science and it was like oh my oh my God, what have I done? Now I've created this monster.

You know,

and he,

at the time,

like would barely show up for like,

you know,

he would show up for two out of three episodes.

He'd be busy.

It wasn't a priority for him.

Right.

So I'd be like,

all right,

I'll put Brad Kersner in.

If you can't make it,

I'll try to get Bill Gurley to show up

or whoever Draymond

to fill in for him.

You know,

and it was always like,

I wonder if Freebird will show up,

but he's actually really committed

to the show now.

For Sachs,

he was high profile,

but nobody really knew him as a Republican.

So he kind of uncloaked as a Republican on the show.

Well, I feel like he was also like, he was almost even more so than any, well, not you,

but he was high profile if you knew about the PayPal Mafia.

But he was like the least kind of public of the PayPal Mafia.

Of the PayPal Mafia, you would say Elon, Reed, Hoffman, Peter Thiel, Max Levchin, Jeremy Stoppelman, Chad Hurley, Ruloff. Yeah.
And I guess Saks would be somewhere in that strata of like being known. But I feel like Saks being known.
Being known, yeah. Being known.
But yeah, you know, I think part of the reason this works is Saks. I think Saks has probably taken the brunt of the head of the pod.
Yeah. Because he is so passionate about, you know, a lot of topics that maybe are unpopular in the tech circles.
So I do think like it's cost him deal float on the margins. Probably.
I think there's probably. I don't really margin.
I wonder. I wonder? He said that jokingly on the show.
I don't know. I'm just thinking like maybe there's somebody.
Kraft has ascended because he's done all in. I guess.
Yeah. Sure.
I'm trying to think if like would, is there a founder? I wonder. I don't know this.
But is there a founder who's a young founder who would say, I would never take money from Peter Thiel's venture firm because I'm so liberal. For sure there are.
And those people feel that way about Kraft now. But for every one of those, there's 10 more.
I kind of agree with your position. Yeah, I would agree with that.
So anyway, I do think like he's joked that it's cost him deal flow. I don't know if it has.
I think truly the benefits of- The pod too, I think for people in America and people in tech has moved, I think, a lot of people towards the center. I think a lot of people were moving towards the center, and we codified it for people.
We maybe made it okay to admit you're a moderate. Yeah.
You know, I've been telling folks from the beginning, I'm an independent and a moderate. I voted probably Democratic three out of five times, four out of five times.
but mostly that's a function of the fact that i've lived only in new york and california in my life where you don't really get many republicans or moderates but i voted for bloomberg giuliani when brie was crazy and pataki who are all republicans were you here during the sports league era or were you still no i wasn't but i would have uh voted for him um I like competent people and I supported Bloomberg for president, which got me a lot of flack. Really? I don't understand why.
People were very upset that I was for him instead of whoever. I think you guys talked about this on the pod that like, oh, what was the two by two quadrant of like, whatever it was.
We all think we are here in Silicon Valley, which is like social, liberal, fiscal, conservative. Yeah.
We were like, everybody should be that. But we're the smallest of the four groups.
Yes. It is a small group.
I think I believe in competence and staying out of people's lives. So it's very hard to know.
And then even David. I mean, this is, I think, when David and I fight on the pod, which some people love.
And I think some people probably turn the pod off when that happens and they don't like it.

And certainly the MAGA group has no love lost for J-Gal.

I'll tell you that.

Like, my replies have been really crazy.

We get, like, brigaded the last couple weeks.

Oh, my God.

Nuts.

It's funny, but it's also, like, on the margins.

Like, they can get a little scary.

Like, they'll dox me sometimes. And, you know, that's not fun.
A handful of times it's happened. But, you know, I had to tell David, like, David, I am not like, I don't actually listen to MSNBC and Rachel Maddow to get my information.
And by the way, you're pro-choice,-gay marriage anti-war yeah he's the dove and i i was like well okay if you if we don't play this game i'm gonna just dub you david the dove and now you're making me into jason the hawk like what are we talking about here like um but anyway you know what just goes to show how silly the coalition building is like it's totally like, exactly. The two party system requires that if you feel very strongly about something, then you're not allowed to think independently about anything else.

it's so crazy you know i and i think what messes people up is the fact that i actually just think donald trump is a horrible human who you should do no business with has no business being in any

political office and you know it is just horrible on any number of levels but i believe that

independent of his party, he's a Democrat, obviously. Obviously, yeah.
Yeah, and so I would hate him as a Democrat or a Republican. So it's not personal and I would love to say- Or it is personal with him, but it's not- It's very personal with him, yeah.
I mean, I just think this is just a horrible human being on, you know, in every way. Now I understand for some people, he represents change.
For some people, it's like the way the Republicans secured office and that's all they care about is winning. I get it.
Whatever. And I think so much of the human condition is like being a part of a community.
And he, for so many people, is a symbol that means, hey, all my and neighbors we're we get to agree on something so that we all can find togetherness in something and for some people that's the flat earth and for other people that's startups and for some people it's the tribe yeah we don't you know a lot of people don't practice religion anymore and so he's their religion and hillary clinton or elizabeth warren or bernie sanders might be other religions or the new iphone like i found myself ordering this phone and i love it and it's the i4 14 pro and it's magic and whatever but like it's not that different than my old phone but i got to participate in all the fun watching of the keynote and the tweeting and the nerding out i'm like let me look at the image quality versus the old one because it really is pretty it really is pretty. It is pretty.
But like, I got to be part of a tribe. And like, that is a thing that no matter what your tribe is, that is so fun to be there on tribe day and tribe week.
I will say the thing I'm proud about the show, I think, is that it has, you know, through a lot of the trials and tribulations shown that you can be friends, disagree, learn from each other and and have a vibrant debate, which is how we all grew up, I think. When I say we, including you guys, but also specifically the besties, I want to be friends with people who I disagree with.
I want to debate stuff, right? And then people are like this guy, Dean Preston, and he's like one of these supervisors here. He's a super idiot, like guy in San Francisco who like, you know, like won't let them build housing and all that stuff.
and he's like one of these supervisors here he's a super idiot like guy in san francisco who like um you know like won't let them build housing all this stuff and he's like you're just a conservative blah blah and i was like you don't actually understand who i am he's like you're a conservative billionaire i'm like wrong on both accounts but thank you for the latter my besties remind me on the latter i on it. Not trying to be a billionaire.
Thank you. On that, another thing that's really fascinating to me about All In and you guys is before All In, and still to a large extent, I feel like Silicon Valley has this weird relationship with money.
Like, super weird relationship with money. Remember there's a whole thing about like zuck drove like an acura svv that all came from david filo and um david filo and jerry yang were driving their old cars right like the cool thing like you you could like make money build a company but like you never want to like you never and be understated you guys i think are the first like 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 uh you know yeah i believe in capitalism i think it's great if people

create jobs and if they get rewards for doing so like fine i literally the book i'm right my

second book right now i'm writing is about wealth and money and like but not like in my regard

Thank you. words for doing so like fine i 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 so i'm like literally been thinking about this topic a ton and i think we worry a little bit too much about wealth creation um with like a small like outlier wealth creation and we we don't think enough about inspiring people to create companies and learn.
And like the time,

you know, with a small outlier wealth creation. And we don't think enough about inspiring people to create companies and learn.
And the time I create the most controversy is when I'm like, I believe anybody can do it. And people are like, you're so wrong.
And I'm like, am I? Because I go on YouTube and you could type in any topic that you want to learn and you can learn it. And all the stuff that was at MIT, where I never got to go, and Stanford and Brown, is online for free.
And I listen to macroeconomic classes and AI classes. When I'm like, it's 10 o'clock at night, and I'm doing my email, I'll just put one of those playlists on from MIT OpenCourseWare.
And I'm like, I can't believe I can take a course at MIT for free anytime I want. And then, you know, flip it, you can build a business there.
Like David Senra over the Founders podcast, like Mr. Beast, MKBHD.
The world has never been this equitable. Yeah.
But people want to spread a narrative that the world is unfair and like i watched oh i think the world becomes so fair and so just and so much information opportunity become available that i'm like wait a second i could never figure out how a term sheet worked and nobody would share their term sheet and now there are a thousand videos and blog posts on how to negotiate your term sheet The world is still unfair. I think, very.
I think the key insight is like, recognize that the world is unfair and actually what that is, is a game on the field and figure out how to play the game on the field. But I mean, it's never been more fair.
So the world is unfair, true statement. And in America, it's never been more fair.
You learn google has like five courses online i think it's called grow with google or something where they're teaching how to be a ux designer how to do this how to do that and it's free so that they can get more people to apply for jobs and the average job entry salary for these things is like 80k so i i find it's very weird in the world I think there's like a group of people who want the world to be more unfair than it actually is because it makes them feel more virtual signaling goodness well that's their community that's how they find that there are other people who love that they tweet that the world is unfair so they and they have to and it typically like is a certain type of person I'll just leave it at that okay can i so i'm going to leave your question i teach founder university now i have a course where i teach people for 12 weeks um or i should say i have a team that teaches it and i'm going to actually teach it myself uh this next cohort where i just teach people how to start companies all right let's plug it how can they find out where they're not university that's it there you go yeah i mean, basically, it's free. The way I did it was you apply.
If you want to build a company, you pay $700. If you go and you get to week 12, we charge your stripe back, the card back, the $700.
If you don't come, or if you don't have an excused absence, if people miss something because of their kids or whatever, fine. But we just try to get people to complete it.
Over 90% of people complete it. That's cool.
And then we're investing're investing 25k in some of those folks to help them start their companies like people don't know all the work i'm doing like quietly but like 200 people go to this course now i'll maybe have 400 in the next coat the fourth cohort we'll see but you know like people can learn how to create companies and they're like no they can't and i'm like yes they can you have to have gone to Stanford. I'm like, no, I've invested in 350 companies.

Like maybe 5% of the founders went to Stanford.

Like, no, that's just not, it's patently false.

Like, you know, you have some confirmation bias.

You're dealing with a data set from 10, 20 years ago.

I get it.

But I'm telling you like on the streets,

ground level truth.

We all meet with founders all day.

It's never been more diverse. It's never been been more open nobody cares where you went to school nobody cares where you live anymore nobody cares where you live they care about what you've built and your traction like it is post pandemic all people care about is like show me your metrics show me the product show me your team what are your skills great let's go what's your growth rate it's basically become like as beautiful of a meritocracy as i've ever seen and man you say the m word it freaks people the fuck out i'm like why is this so scary for you that silicon valley is a meritocracy and they're like because it's not and i'm like it kind of is can i can i answer your question earlier of what why i think all in works yes all right right.
Go ahead. So I think you've got the perfect storm of three things.
The first thing is... A lot of zeros on this out there, by the way.
Billionaire porn. Most people, you're counter-positioned.
Most people who attain that level of wealth crawl into a quiet hole and make sure no one knows about the private jets. You're doing shows from boats and jets.
Yeah. So there's like like i don't think we've done one from a jet but yeah there was definitely two boats in the last two years that's true in some peak moments of all in it's like watching billions in real life it's like you hear you hear chamath talk about this spread trade and you're like this guy's got a lot of money on that spread trade and like does he actually have a key insight here or is he and like there's there's this interesting intrigue there so bucket one is like billionaire porn bucket two is uh by the research you guys do and and the folks that you each work with because there's definitely researchers that seem to be involved you bring things to the table they're like brand new insights that aren't widely available yet so i feel like i was learning things about covid19 on all in that i wasn't getting through any other source i'm like somehow this is not making it to me and this feels very like a lot of it proved out to be like this was good information before it was mass all four of us are information junkies with a lot of research and teams that how many how many people all in how many people touch an episode of all in one producer nick that's it no i mean but like the research i don't know i i'm pretty sure files open on people's computers when they're talking uh we have a docket with the notes but that's mainly for me to queue it up like i just read the four or five bullet points so people know it so i i do that with my team the docket but the docket is built from you know the five or six stories that people submit to our group chat and say hey put this on the docket right and um i i think sax has some research help i'm sure friedberg and chamoff 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 world. So you guys are investors.
You know how it is. Like you do 20 meetings a week with founders.
They're going to tell you everything about the world. And you guys are young still, but imagine you do that for 20 years.
You're going to get smart or you're a journalist for 20 years. You're going to get pretty, I wouldn't necessarily say smart, but you'll be informed.
And if you're hearing the right pitches, you actually are getting cutting edge information before it's widely available. Definitely.
So, okay, that's number two. Yeah, we probably have a slight information edge.
Yeah. Certainly a huge, I will say the information edge compared to journalists having been, this is not a dig to my journalist friends.
I was a journalist. journalist i had 75 people at the magazine we were always trying to figure out from the principles what was going on and tell that story but we were only as good as our access to information and we probably i now looking back on it i think we had between five and 35 of a story and i know that's like probably triggering to a lot of journalists

that they have that little information.

You weren't on the inside.

But you weren't on the inside.

So when you're on the inside,

you have 100% or even on the inside,

you might only have 50% depending.

You get enough to run with

and you feel like, okay,

now there's enough story here, let's do it.

And like, that's clearly not the whole story,

but it's enough to put the piece together.

You're trying, and then over time,

process journalism, as some people have dubbed it, you know, maybe the six or seven stories will tell the full story yep which a third component you think makes it successful it's the thing that David and I took forever to realize works about acquired which is relationship and charisma yes like people like having fun by listening to stuff sure and so like if we can make history fun then a little bit of joy goes a long way four hours of us diving into stuff you would never read in a book and you guys do that in spades like it's just so fun to like temporarily join your world i mean the fact that you as a podcaster who makes elite content like top 100 content find content, find it compelling. It's just, yeah, that's very...
Listen every week. Don't miss it.
I can't believe it. Literally walking the baby up and down the hills listening to...
I mean, I have people tell me they listen to it twice. They take notes.
I'm like, wow, that's great. You know, I was very...
Don't take notes. Maybe I should take notes.
Well, anyway, I was very intentional with my role in it to step back and be like the point guard. But, you know, I'm a shooting guard, too.
So sometimes I will want to shoot the ball and I can do both. I'm a combo guard.
How did the Freeburg Host episode come about? So one week, you switched roles. Well, he was like, I think this could be done better.
This could be better. And I was like, go ahead.
And I was like, sure. I'll just shoot.
And you passed the rock and all. I was like, yeah, you want to be a good guy? Show us.
And he did a solid job. But let's be honest.
It's not a point guard. It's not Showtime, that's for sure.
Like, I don't think people are going to go to watch him play point guard. I mean, he did a serviceable job.

And put that on his tombstone.

No, but he shines when I created science quarter for him to shine.

I said, bring me a sign.

He's like, oh, you know, I don't know if I want to talk about politics.

I was like, listen, Sacks wants to talk about carnivore politics.

I'm giving him his red meat.

Here's your quinoa.

Come to me with a science story, you know, and we'll do this quinoa corner kind of thing. And I made him the sultan of science and so good you know it was it was a distinct effort i really wanted to make him shine you know and um it worked you know it worked because you see how engaged he is and what used to happen was and fans know this i'm not speaking at a school here you see it every episode sax would disengage during science and quinoa would disengage during politics.
And what I've been trying to do is keep both of them involved when the other is doing stuff. And Chamath and I are involved.
That's a hard job. That's a delicate.
I studied the McLaughlin group. People don't know this, but I went back to look at McLaughlin and I watched him moderate.
So people, there's a big debate. Do I interrupt too much or not enough? Do my interruptions, I call them interjections, do they help? And I actually looked at the interjections.
And if you look at McLaughlin, you guys did not grow up on McLaughlin. I'm super unfamiliar with what this is.
So the McLaughlin group was the best Sunday morning show. And it was so good, SNL with parody mclaughlin it probably had a million people watching it but this guy mclaughlin was like pretty cantankerous and if he didn't like what people would say he'd be like wrong this is the answer you know like and it became so competitive that you wanted to watch it yeah now what i didn't realize by adopting that would be that sax is the ultimate debater and will fight like a dog until he wins any debate.

And so I may have pushed Sax into more of a debate situation where I'm trying to not have it be a debate.

I'm trying to have it be a conversation.

So what I've been working on is trying to keep it be a conversation.

And then some people in the audience are like, you have to be the fact checker for Saks. And I'm like, no, that's not my role.
I'm not real time fact checking Saks. And so that is a delicate balance of like, and then sometimes I'll ask questions, specifically because I know the audience doesn't know what, you know, fair market value when they hear an acronym so i'm like explain that right and

i'll stop somebody now i mean you're you're expanding the team to dentists like when that's correct thank you so people are like oh jay kyle's an idiot he doesn't know that term or i say to somebody can you unpack that can you explain that obviously you know that for myself you were what the third or fourth investor in uber yeah like exactly well played i think he's been in Robinhood, too. Oh, Com, too? Wow, who knows? And I'm like, dude, like, I'm asking that question on behalf of the audience.
So when I'm moderating, as opposed to being an interviewer, or as opposed when I'm working with Molly, and we're chopping up the news, when I'm the shooter there, right? And she's maybe playing point guard a little bit, and I'm shooting, and then sometimes I'll pass it to her, and she shoots. she shoots.
Like I can travel between those roles and you know, in that role, I'm acting on behalf of the audience and I get the sense like he's going, Chamath's going too fast. They don't know what the spread trade is.
Let me pause. Can you explain one more time or let me reflect back to you.
Is this what a spread trade is? And he's like, almost this. And that's what I think has brought in to your point a lot of the dentist crowd and having an intimate sense of where your audience's edges are is is a really important role there like when we have guests on i'm always trying to catch yes where where do they just go slightly too deep and i need to pull them up so that we yeah and and you know podcasting is about So it is really an art.
Like, do you want to stop somebody when they're going down this like crazy rabbit hole? There's no clock in this room. Well, they're going down some rabbit hole that has never existed in media before.
Right. So...
And you want to let them go, but you need to make sure they're taking the stairs. Because like, if they just jump in, you're like, oh God, no one has any context.
They can't learn anything new because you're like, you're not connecting it to something they understand. they understand they just jumped into brain surgery yes let's just explain to us what's going on here what how are we going to chop up this brain right like yeah yeah it's a it's a bit of an art but you know i i have to say like it's it's been a different muscle for me to flex and uh it's been great fun for me the other thing like i don't know if you think about it on this axes at all but like i kind of think of there's i used to think it was very binary like there's two categories of podcasts there's uh candy and there's vegetables and like i listen to the audio version of stratechery and that's my vegetables and it's not like deeply it's enjoyable intellectually but it's not like fun and um i i can't i certainly can't be doing anything else with the language center in my brain while I'm listening to that.
I have to be on a run and sometimes even at home so I can take some notes or look something up. I can be cleaning.
It's a pause type podcast. You have pauses sometimes.
Sometimes you hit and rewind. Let me make sure I get what he's saying here.
Or I can listen to the talk show with John Gruber and it's just like if I missed out on 20 minutes because I like brushing my teeth and then I left the room and I came back and I'm like, Oh, I didn't actually miss anything. Cause this has just been like, it's comforting.
It's like, I love all the stuff he's talking about, but like, it's not must listen every time, every minute, every second concept. And I'm not using hard parts of my brain to understand.
All in has become candied vegetables. It's both.
It's both. Yeah, for sure.
Yeah, I try to do with This Week in Startups and All In is try to have it be both. A little bit of personality, a little bit of entertainment, some fun hot takes.
Right. I mean, related but separate topic.
Silicon Valley. Yeah.
I feel like, especially there's a lot of, part of the origins of All In, there's a lot of bashing on San Francisco politics and California. There's a lot of crap wrong here.
Yeah. But you guys are all still here.
For now. How are you guys feeling about that? For now.
Yeah, how do you feel about that? What do you think of the Bay Area? You know, I lived in New York, Brooklyn, then Manhattan, and then I lived in L.A., and then I lived here. And so I think I'm moving to places I enjoy less and less each time.
I enjoyed Brooklyn and Manhattan much more than LA. I enjoyed LA much more than San Francisco.
I don't know where to go next, but I'm going to go somewhere. So why are you still here then? There's no reason for you to be here.
I came up here because I had a lot of friends up here. And I had done LA.
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. I wonder how I would do if I was up there in the industry.
And I was kind of this. Because if you wouldn't, you'd always wonder.
Well, Michael Morris used to call me the mouth from the south. Because they had like two investments in LA.
Oh, the mouth from the south. What have you had to invest in J.
Cal? Sir Michael saying that. But I moved up here.
And yes, I love it up here. It's quite bucolic.
My kids are loving it. It's quite nice.
I would love to live in another city in my life or two. I could see myself in Austin or Miami.
I like both of those cities. I think Austin's kind of the future.
I think California is going to be damaged for a decade or two. So I think for the rest of our adult lives, this town.
Because of the pandemic? I think the politics and not appreciating the politics, the regulation, and not appreciating the tech industry is really the problem. And then you look at this guy, Dean.
All right, listeners, it is time to talk about one of our favorite companies, Statsig. It's funny, David, Statsig has gone from this little startup when we first started working with them a couple of years ago to this total powerhouse now.
I know it's wild. I was looking it up and they have added all these customers since we started working together.
OpenAI, Figma, Atlassian, Vercel, Notion, tons more. At this point, if there's a growth stage tech company out there, there's pretty good chance they're using Statsig.
Yep. So listeners, if you are unfamiliar with Statsig, they basically took what was the standard product infrastructure at every big tech company and they built it as a standalone company.
This includes advanced experimentation tools, A-B testing, feature flags, product analytics, session replays, and more. So if you're building the next great software company, this sort of infrastructure is essential because it allows your product and engineering teams to release things quickly, measure the impact of them, and track progress over time.
Totally. So, I mean, as we've talked about on the show forever at companies like Facebook or Netflix, data was just a part of how everything was built, which contributed to all the crazy bottoms-up organic growth that they had.
Now with Statsig, you can get that from day one at your startup. And today, they're not only trusted by startups, but also by more mature enterprises like Bloomberg and Microsoft and Electronic Arts.
Turns out that a single system for data-driven product decisions is useful at any scale. Yeah.
And by the way, the scale they're operating at is completely insane. They process over 2 trillion events per day now.
By the way, David, this is updated. The last I checked it was 1 trillion.
And then this morning I pulled it up 2 trillion. And they handle releases to billions of end users.
If you're listening to this podcast and you've used software in the last few years, there is a very good chance you've been a part of many experiments orchestrated by Statsig. Yeah, it's just awesome.
And as they've gone upmarket, they've also started to offer some interesting deployment models, like being able to run the whole thing natively inside your existing data warehouse, or just using Statsig's fully hosted solution. If you want to leverage Statsig to grow

your business, there are a bunch of great ways to get started. Statsig has a very generous free

tier for small companies, a startup program with a billion free events that's $50,000 in value,

and significant discounts for enterprise customers. To get started, go to Statsig.com slash acquired and just tell them that Ben and David sent you.
Thank you, Statsig. when they sold their homes.
And I'm like, and you also lost two incredible founders who've created billions of, tens of billions of dollars of wealth

for San Francisco, you idiot.

And like at the same time,

Francis Suarez in Miami

is listing all of the venture capital

and doing a tweet storm

about all the companies

that raised venture capital.

So you have one guy, Dean Preston,

dunking on people saying,

we have this 1%.

So when they sold their $30 million house,

we were able to extract a million too. That's why tech doesn't like me i was like hey dummy yeah now that all the future earnings are gone now what's like california marginal tax rate is 13.3 percent i mean but just so they have an exit tax now for homes in san francisco right so if your home costs over 10 million when you sell it i mean i think it's just a sales tax 1.2 million from them selling their home versus 13 percent of their future earning stream literally the chef at slack made a billion two paid a billion two in taxes yeah from their rsu's like are you such a where do you think a million two probably yeah like the The million two.
Yeah. But that order of magnitude.
Probably paid in taxes on their RSUs at Slack.

Yeah.

You. probably yeah like the bill the million two yeah but that order magnitude 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 uh but anyway the fact that we hate entrepreneurs who create jobs and wealth or certain certain people do, is just insane.
It's just insane. Like, I mean, you could go change the tax code.
It's fine. Like, you know, raise the minimum wage.
Like Bernie Sanders and Elizabeth Warren attacking Bezos endlessly. And then Amazon starts paying $22 an hour, gives you benefits, and pays for your college.
And it's like, okay, hold on a second. I know what Bezos just did.
He took the platform that you could never actually enact, and he enacted it inside of Amazon. If it's not perfectly clear what just happened, literally he's dunking on you.
You wanted free college and couldn't get it done. He gave it to Amazon employees.
You wanted a $15 minimum wage. He made it $22.
And you wanted everybody to have universal't get it done he gave it to amazon employees you wanted a 15 minimum wage he made a 22 and you wanted everybody to have universal health care and he gave universal health care like that is literally what besos did to them how embarrassing maybe you can argue that like them pushing and pushed it but no no yeah definitely it is literally him showing like uh as the amazon crew showing, let the free markets work. The DoorDash, Uber, Amazon, Starbucks absolute race and battle to just hire entry-level employees and make it delightful for them is what has driven, and a lack of immigration as is what has driven these salaries up right and the benefits up it's extraordinary what's happened with the free market is still seven dollars federal minimum wage is seven and change so right and 15 here in the city in New York is 15 like yeah it's weird all right listeners it is time to tell you about one of our favorite things now that Jason is out of the room temporarily.
For all of us who have been paying attention in this crazy space, there are now a ton of options for picking a corporate card and expense management software. So how do you cut through the noise? What's the difference between all of these companies? Well, any founder or CFO who's expanding globally and is becoming really like an enterprise grade company will tell you most are really not up to the job.
Reimbursements take forever. Issuing cards internationally, huge, huge pain.
And they basically never offer currency visibility. Totally.
Well, this is why. So Brex was one of the first corporate cards, as most folks know.
The first like new innovative. First new innovative startup, corporate card for startups.
That's how they started. But now they've added on a whole spend management platform on top of the corporate card.
And it makes so much sense for it to all be together. The data being integrated lets them do really great stuff.
You want your employees to be compliant. So it ensures 100% compliance, but also you need it to be easy for them.
So you can do cool stuff like have managers set budgets. And then as long as people are spending within those budgets, then they're just in policy.
Everything's always approved all the time. No receipt chasing.
So receipt chasing, no approvals, no, it's all just done. It's all integrated.
And they really are thinking about this the way enterprise companies who are expanding globally and deal with lots of contractors in lots of countries with lots of currencies and just need a command center that they're not going to outgrow, that is really when you need breaks. Yeah, like globally, like how many companies these these days even startups employ people globally who are you know not just need to be paid but then are like spending oh dude buying things going to dinners etc around the world like you need something that operates globally so plus it's awesome the like the remote work thing is here to stay they shared the stat with us More than half of the startups in the last YC batch are from outside the U.S.
And then there was another one. Accenture said that workforce models with productivity anywhere are now used by 63% of growth companies.
So remote is not going away. So you really do need to figure this out for people who live everywhere.
Despite you and I and Jason being together here in person today. We are remote.
So many of you are, we know, too, obviously. The last thing that we want to tell you about with Brex today is related to being remote in different time zones.
Brex now has 24-7 enterprise class, enterprise grade support, which is important because if something goes really wrong with your spend in a time zone half the world away when everybody in HQ is asleep, you really want somebody to be on that. So Brex now 24-7 is able to take care of everything.
Yep. If you have global enterprise ambitions, Brex is the answer.
And of course, they have a great mobile app. They were like one of the first corporate card programs to have a delightful mobile app.
And now that they're serving large, growing customers around the world, they can do everything from that mobile app too. Indeed, indeed.
If you want to learn more about Brex cards and spend management and why both of those together are now loved by teams all over the world go visit brex.com slash acquired or click the link in the show notes thanks brex we referenced this at the start of our conversation you're working as hard or harder than you ever have you said you've got a smarter a new well of energy yes tell us about it well i find great purpose in what i do and uh when my friend tony shea died i really thought deeply about like what i wanted to get out of the rest of my life and i realized like these are the things i really love doing and these are things maybe not so much and i just realized my life over the last two years and so What are those buckets I really love doing. And these are things maybe not so much.
And I just realigned my life over the last two years. So what are the two buckets? Yeah, exactly.
So I can tell you the things that just to me, I'm just not going to get any pleasure about in life. Working like, no offense to my incredible lawyers, but negotiating term sheets and legal and HR issues and accounting and operations and tax and that entire stack of things.
Not fun to me. not fun at all and i'm sure you never viewed that as fun but at least before you were like i'm willing to put up with it because it may maybe it's a thing that creates value enough for me to do it um doing my podcast every day absolute joy entertaining an audience you know thinking uh thinking about the world and having these conversations i had toby from shopify on today like i leave the toby interview it's like his third or fourth time on the pod that's awesome and it's just like instead of us having dinner or lunch we just record a pod the end um did you in person or did he no just you know popped on zoom i he you know he just started because he did that tweet about his compensation tool yeah where you know here's your total comps use a slider i was like that's brilliant come on the show you want to come on the show and talk about it's like yeah of course um and so like those conversations i just looked at them and i'm like my energy coming out of the show is on 11 why am i not doing this every day and i watched howard stern when i was a kid or charlie rose do it day in and day out.
And I was like, I could be like those guys. They, every day, get on there.
And they seem to love it. And I do.
And so I just committed to doing it every day. And I love it.
Isn't it weird when there's something that takes a ton of work but somehow doesn't drain you? Not at all. To me, it's like going to the gym.
It's like working out or having dinner dinner it's just something i do every day that gives me great joy and then that's i recruited molly i was like i need somebody to do this with me every day oh yeah who i respect and who's awesome and bring something to the table that i don't have and having she's so great having someone to play off of sure like i feel like that's the thing that's kept acquired going yeah is that like you and i can like i don't know how you did it alone for i don't know a decade uh well i you know i'd have guests on it was largely a guest-driven show and then i would do the news round table once a week because it was once a week then twice a week then three times a week and then i was like well however many i just sell out i'll do it five six days a week whatever um and um i enjoy meeting with founders uh when they fit a certain profile uh but it's very hard to meet with a large number of founders, given how many are coming in. And it's hard to work with them when they're just talkers.
Yeah. To me, that's a very hard part of the job, because it becomes very repetitive.
So how have you excised that? Well, I created a platform, Foundry University, where if you want to build something, I will talk myself to 200 people you can build. And then whatever arises, as the performance and the product, you know, and as people move from talkers to the walkers to from, you know, when they actually start building stuff, that's when I get great joy.
And so I'm like, bring me the people who have product velocity. So I told my team, listen, you're doing my team does six people don't understand the scale of the business I have.
Nobody's Yeah, I don't really understands what I'm doing. And I kind of like it that way.
But the angel syndicate is now the largest syndicate in the world. I've deployed like $185 million in my career as an angel investor doing 50 million a year.
Now, I'm raising the fourth awesome. I'm raising the fourth fund in public.
11,000 angels in the syndicate. This is going at a really significant velocity.
If you were to look at the slope, it's not quite a hockey stick, but it's hockey stick-esque in terms of the total capital I've deployed. It's in really high-quality companies I've been getting better at.
There's 11. I have 22 people and 10 on the media side and 12 on the investment side.
And of the investment team, like people don't understand. They're like, oh, you're a solo GP.
I'm like, yeah, with 12 people. Those people are doing 60 introductory meetings per week.
Six zero. And then we're doing maybe 15, 20 second meetings.
So there's, it'll be 100 meetings a week shortly. Probably across 10 people.
Or 12 people. But you're not doing the.
I'm not doing them. Yeah.
And what happens is... You had this line, was it on, it was on Twist, I think.
Not for me. That's a lot of work.
People say that's a lot of work, but you're like, yeah, but not for me. That is the new philosophy.
This is why my energy is really high. This is your unlock.
I have told everybody who comes to work for me, I work 60, 70 hours a week. Keep up.
If you can't keep up, don't be here. I'm looking for a fixed 50, a solid 70 hours a week keep up if you can't keep up don't be here uh i'm looking for a you know a fixed 50 a solid 60 hours a week if you want you don't have to match me 67 but 60 or 70 hours a week but keep up and are you looking in that team are you looking for like the next jason calacanis to be a part of that team or is it like someone who likes doing that part like that's well let me ask it more directly is it someone who's content with doing this or are you looking for people that are like hungry enough to be the next jason i'm open to all of it yeah i'm open to all of it i don't they don't need to want to have my you know absurd um unhealthy desire in my youth to be successful um and if they did they probably wouldn't come work for me but maybe they would actually i would uh so yeah they probably would not very long ago yeah you come you'd learn years you'd extract two people come and they work for two three four years and they go start their own venture fund or whatever muscle tough it's great um but what i told them was you know let's just find the great companies and And I looked at investment team meetings.
Usually they're Monday.

People do it for an hour or two, and then they go to lunch.

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

Hit me with companies.

So that was another innovation I did.

And I also brought Mike Savino, who was my first boss when I was in my 20s doing IT.

And I brought him on as president.

So this is like one of my lifelong best friends.

And I said, run the company.

Here's what I want to do.

The podcast, meet with founders,

do the LP fundraising.

That's it.

You know, teach the course.

Are you enjoying the LP fundraising?

I am now, yeah.

I'm kind of like,

remember in X,

I don't know if you watch Billions. Oh yeah, every episode.

Great.

So you know, like at some point, he he was like i'm gonna go raise money yeah it's cap raise time it's cap raise time and like wags is like so i got my wags mike savino's my wags yeah and i got my wags who just fixes everything and i'm like i'm gonna go raise money and so i literally was like we're doing 506c and they're like and so you've talked about this about this now. You're now, you were in kind of this one bucket with your capital.
And now you're going simultaneously in two directions of you want the public and you want the big institutions, right? We'll see. I've had select institutions make small bets.
The first fund was 10. The next fund was 11.
And then the last fund was 44 million. The first fund I in five years, the second fund two years, the third fund two and a half.
Five years. I was just, that was my first fund.
It was, you know, me, Bill Gurley, Dave Goldberg, rest in peace, Tony Hsieh, rest in peace, David Sachs, Chamath, just a bunch of my friends put money in. And it was to see if I wanted to be a venture capitalist and do this as a career.
And I was like, yeah, I just did it over five years. And the second one, I raised 11.
It took me six months to a year to raise the first. It took me, the second one took three to six months.
The, no, it took six months. The third one took me three months to six months.
And in this one, I think I'll wind up raising in the first 10 days what I raised in the first, yeah, a couple of funds.

Wow. I literally did two webinars.
A couple hundred people came to each. So for people who are listening, 506C is you can raise in public, which means you just can tell people I'm raising a fund.
And I was like, well, I'm doing all in. It doesn't make any money.
I have this week in startups. And I watched a bunch of these young, um, aspiring VCs raise on publicly.
Right. Yeah.
You didn't raise publicly. No.
You did private. I thought about it, but for a whole bunch of reasons.
Well, it's kind of scary because people don't do it, but if you have no track record and you want to raise, so like this guy, Mack, the VC. Yeah.
You, you did a great episode with him. Yeah, it was great.
I had was great i had him on uh i had like you know first time founders for a season of angel um which is like a subsection of the this week's startups podcast 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 dollars and uh he's african-american and he's like it's just a matter of how hard do you want to work and i'm like well careful saying that publicly because there's a group of people who do not want you saying that he's like no it's just all you have to do is like you go to angelish you set it up and then you just start talking to other vcs you talk to them and you just you just have to be willing to take 50 meetings a week i'm like dude do not say that it's easy to raise a venture fund as a black man in Silicon Valley. What? But that's his position.

It's not that it's easy, but that it's possible.

On the internet, too, you find your people who believe that with you,

and then they believe in you, and then they back you.

Correct.

And that's the, like—

Correct, correct.

And so the whole thing goes, but what I noted when I was taking my notes,

watching him, was so many times people were like,

oh, when's your next fund?

And I'm like, three years.

They're like, oh, let me know.

And I'm like, okay.

Right, I'll put that right there in the place where I keep everyone who tells me yeah three years from now what to do yeah and so you know um 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're gonna have 250 accredited up to 10 million and then 2 000 qps and so it's it's so it's a lot more work. And QPs.
Not for you. But not for me.
To catch everyone up. Qualified purchasers.
Look at you playing Jason. I know you know what a QP is.
I just want to dish the ball. I think it's 5 million in investable assets.
And then accredited now is 200 if you're an individual for the last two years, each of the last two years, and 300 if you're a couple, each of the last two years in income or a million dollars. In net worth.
In net worth outside of your primary residence. So there's a whole, and these things are going to change over time.
But I believe that we're going to have a test for accreditation. And you'll be able to be sophisticated if you take a course.
So I think that's coming in the coming years. So just like I democratized, Angel Investing wrote the book, Angel was the first syndicate on AngelList, the most successful syndicate on AngelList, created my own, got the domain name The Syndicate, created the largest one, have done 265 syndicate deals, by far like the largest amount of anybody, I think.
I don't know. I mean, now as a participant with a fund on AngelList, like these are like, those are big numbers.
Like we've done- You do something consistently. Four SPVs on AngelList.
And we list and we have the fun too but like yeah like that's a lot you're herding cats you need to have a lot of people um but anyway putting all that together i think now is the time to democratize venture capital so that's what i'm attempting to do here is i want uh 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. It's high risk.
It's high reward. I'm in 20 venture funds myself, including yours.
Thank you. But don't pitch Jason.
I'm sure I will do yours. No, I mean, I'm just going to pick them based on people I know or people I know online or on a pod.
And yeah, I'll do one or two new ones a year. Well, this is kind of to the conversation earlier like on the internet this is the democratizing thing nobody's going to just give you if you just you know nobody's going to just invest in your fund but if you go do stuff yes and then people like oh jason does stuff great i'm gonna back jason ben does stuff like be of action yeah and it doesn't mean you have to start a podcast you could be a blog you could do whatever you could create, whatever it is.
You can do any of those things. You can have a track where you can be an advisor to startups, whatever it is.
Do you like the idea? I'm curious, as someone that's always raised from sort of individuals, do you like the idea of having some institution be like, can we invest $15 million? Oh yeah, of course. I mean, I've had five, you know, $1 million checks, $10 dollar checks in the fund from institute from you know fund to funds and institutions you know but i would very much at some point i don't need it but i would be meaningful for me uh both my parents are cancer survivors to have memorial sloan ketterings endowment or an endowment ucsf or something like that somebody like that you know if they wanted i would work you know really hard to try to get them a great return i would find more i would find even more meaning in what i do yep uh and you know i got that from sequoia like you know you they would have this sequoia dinner every year for the founders and they would say here are what the foundations who are lps are doing with the money you made for them with your companies.
Click, click, here's what

Ford Foundation's doing, here's what this foundation's doing.

Their conference rooms are named

after their LPs.

And this is real.

I find we have state pension funds

and stuff like that.

In PSL Ventures.

You take it much more seriously.

Of course.

Because it's not just about the reward. It's not like, oh, I'm so excited about what we're going to do for them.
It's like, this is really important to preserve and not grow, but like preserve this capital. Yeah, yeah.
Which the psychology of doing that while you're taking big swings with asymmetric upside, that I find to be a fascinating dance. That was like one of the seasons of Billions was he's like, I'm going to be a family office.
No, I'm going to raise my own fund, right? And so there's this natural tension for acts like, which should it be? And he decided, yeah, I like when I have other people's money because he seemed to perceive like i think he felt that he wasn't a

somebody in his ecosystem in his community without managing outside capital i think it's like playing you know in the bubble with nobody in the stands versus right getting on the court yes at madison square it's like and there's people in the stands your returns your numbers don't mean anything unless you're putting them up for dude i'm doing this public where i should say quasi public people They'll have to sign up to come to a webinar.

But I'm sharing with them like here's my the totality of my investments and here's what i've done and here's what i plan on doing with my team um so you know i'm kind of enjoying it um and if you know i've met with all the top endowments in the world over the years and they're're very kind to me, but it's always been like solo GP is a blocker, no track record. Your fund is so small.
Small fund. We're a $50 billion endowment.
Yeah, and you know, like, you know, at some point, like one of the ones who's the most rigorous, I won't say exactly which one was like, we have a lot of respect for you. We know who you are.
People would like you to sign a book and take a selfie with you when you're here. But I just want to be straight with you.
We don't add many funds. And if you go through our process, it's going to take a lot of your time.
And it's going to result in you not getting our money this time. I don't want to put you through that.
But I respect you. And if you want to do it, we'll do it.

But maybe just put one more fund on the board and let's talk in the next one.

And I was like, let's do that.

I don't need the money.

Let's wait.

And I think what a lot of these funds are doing.

Was that in the last fund cycle?

That was in the third fund cycle.

Yeah.

So now.

So I will contact them.

What I decided to do was let's see what my syndicate members

and the public want to do.

Let's see which QPs come out of the woodwork.

Yep.

And literally I did the second call this week,

the first one last week.

I'm doing the third one next week

and it's been so productive.

I added two more.

So I'm going to do five webinars this fall

and then I'm going to go on the road

and start meeting with folks.

Are there any downsides

to doing the raising in public thing other than? Not that I can see. I mean, I guess you could fail in public to fail to raise the fund.
That doesn't seem like something you're scared of. No.
I could also, you know, the freeing thing, you know, is I looked at the model and I said, you know what I could do? I could just invest my own money in each company and then syndicate them and never have another LP. Right.
But then you're raising capital every single time you're making an investment. Yeah.
And I'm getting deal by deal carry and I have a hundred percent of my investment, not 25% carry on it. And I don't ever have to talk to anybody.
I could just say, I'm bet would anybody like to join me yeah and i don't have to have a fund i don't have to do audits i don't have to do any work so literally this you know it's so funny hearing you say this myself lots of our other friends in the ecosystem that are in similar positions they're having this same question like on the one hand i could do what you just said and do very little work but but have it all be pure on the other yeah i could go do what you are actually doing and like raise have lps be accountable yeah how did you weigh these two um i i'm going into my second era my second decade of uh investing and i again last two years a lot of like sort of post-pandemic and Tony's death thinking, huh, like what's possible here? Because I've won so much in my life. I don't mean to be obnoxious about this.
I know it probably sounds that way, but for a kid who's, you know, going to be a cop to be where I am, and this is why when the guys break my chops on the pod, I'm like, guys, I don't aspire to be a billionaire. It's not important to me.
If it was, I would do a late stage fund. I aspire to be happy and do what I love doing every day, which is the podcast.
maybe get in 40 days of skiing hang out with my kids take them on the mountain and then meet with like you know early founders and be able to say i helped that company at the earliest stages that to me is the rush i found him first i backed him first i sat there with them and figured it out with them we were talking about the legendary twist episode 180 with you and Travis. Yes.
Like, man, that was... That's the secret before the show stuff, David.
Yeah, that is the secret. But from the juicy before the show.
I can talk about Travis. Yeah, but that was like, you know, Urbu was such a baby company back then.
One city. One city.
I invested and I had an open angel for him where Cyan Bannister and Chris Fralick from First Run, you the company. I think they both met them there.
Sokka was there too, but he had a relationship with Travis, so I can't take any credit for that. And Kevin Systrom was watching, and I was going to kick him out because he was at this co-working space called Dogpatch Labs.
I worked there too. I worked at Co-Tweet.
Yeah, so he was... Oh, Co-Tweet, I know that.
Yeah. So he's sitting over there building bourbon.
Yep. 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 get him out.
Wait, this open angel form was at Dogpatch Labs? Here on the pier. No way.
I think that pier then they shut down because it was going to collapse. Condemned.
Yeah, condemned. So that was there.
Naval also did a bunch of like events there for angel hacks at the time naval and i were very friendly um not not friendly now but not we don't hang out or we but we used to hang um kind of bummed about that if i'm being honest um i really respect him and uh he was doing something called venture hacks at the time so he would just send an email with here are the five companies and i was doing it in person and he's like i'm gonna do this thing angel list i'm like well i'm just in person thing and he's like great let's just you know trade notes or whatever and then he sent me the syndicate thing he's like do you know about spvs i was like i don't explain it to me he taught me what spvs were he introduced me to assure fund management which i wound up investing in um did you buy that? I didn't buy it. I mean, I bought 5% of the company.
I invested in it. But they back everybody.
And they've done more SPVs. I don't know if they're up to $10,000, $5,000.
I mean, they've done a ton of it. Seriously great group over there.
And so he taught me how to do syndicates. And the first one I did was Calm at $4 or $5 million.
That's nuts. It's funny.
I was looking for your- Like literally winning a championship the first time you step on the court. I was looking at your track record, getting ready for this.
And I was telling David, I think the word that I used, because obviously Uber is some ridiculous multiple on a return. But then there's these other ones that are promising but early.
And then there's other ones where it's been a less than Uber multiple, but still a good Uber multiple. But you look at calm you just i looked at david i was like he sharpshooter that one like that one i could be even more proud of because i'll tell you why it was like ridiculously early and like a super low basis they had it was four million dollars we put 370 ak and on six percent and they didn't raise any money until it was a 250 million dollar valuation so no dilution and sharpshooter sharpshooter and it's like

really like

I could even cry telling the story. But Alex, Stu, and I became very good friends.
Ed and Michael Acton afterwards. Because he wasn't actively running comm while Alex was.
Alex at some conference, I was interviewing him and doing a little victory lap for him, giving him his flowers. And he said, I just want to stop and tell you, you don't actually know this story, but we were going to shut the company down.
And Mike and I had a conversation. What? Do we take your money? But we're not sure about this.
But you believed in us so much, and you insisted on us taking the money, but we had just pitched 40 investors and they all said no.

And we were trying to debate if we could in good conscience burn your money to do this.

And we probably, Com would not be here for one for you.

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

Yes, I think so.

I think so.

Because you're like, take more of my money.

No, no.

But if you think about that as like a, that is not the case with Uber or Robin Hood. I was along for the ride.
Let's be honest. I did not change the trajectory of the Japanese.
But like, but for Jason Calacanis, Colin did not. Well, he said it's, they were going to shut it down possibly.
I don't believe that they would, but I do think it was on the table. That's like real angel investing.
That's real. That's real.
There's a lot of like individuals participating in venture rounds and like yeah no offense oh hey i don't take any offense so like call that angel investing but like coming in when the company could die needs 100k 200k 300k to get it to the stage where they revenue to date i think when i invest like ever yeah uh because when I invested. Like ever.
Yeah, because they were selling the app for $10. Because remember, at the early stages, there was no subscription model.
Right, in the App Store. You just sold an app for $10, the person had it for life.
That's right. So the business model of apps was make a lighter for $1, then make lighter two and charge $3, 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 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 um because you know i was under nda as well you know hey subscriptions are coming that's going to change everything and they were going to do ten dollars a year and i said to alex and michael how much does it cost to go to a meditation class this is donation based there's only like 10 places you can go i'm like well what what's the suggested donation it's like twenty dollars you know i said you want to charge ten dollars a year it's twenty dollars a month how often do you have to do this to visit yeah i 20 hours a visit i.
How often do you have to do this to get value? $20 a visit.

Yeah, $20 a visit.

I said, how often do you have to do this to get value?

It should be a daily practice.

We're like, how often do you have to go and learn?

I said, if you go weekly, that's good.

I said, so it's $80 a month to go.

And we're charging $10 a year.

So that's like $1,000 a year versus $10.

What if it was $10 a month?

They're like, we've been thinking about that. I was like, OK.
And they're like, OK okay yeah i think we're gonna do that and it was then they went to ten dollars a month or whatever they didn't wind up at sixty dollars a year whatever it was but we have money printing machine pretty quickly so i've never made an investment at like pre-product market fit that's like now worth over you know a billion dollars like that's a that's a that's a very early to very successful and i'm curious like did it feel any different when you were making that investment were you like there's something more special here of course than my normal investment absolutely really absolutely and that's what i've basically turned into a playbook at launch and that i'm teaching these 12 people how to do is how to do that what do you think it was like what what was when you look back and you're like factors nine nine okay all right yeah well angel angel dot university no i don't even teach an angel university but oh um i i'm training my team when they're meeting with those 60 companies and every time they pitch me one they say this has three of the nine this has four of the nine and then i'm creating the anti-list these are the things that kill companies so how many of the 15 things we have a long list of things that kill companies how many of the red flags does it have reasons to not invest how many reasons to invest does it have and you know like one of them for me and everybody's got their different philosophy i won't give all of them but one of them is world-class design and so i'm trying to teach people what world-class design is and world-class design to me is if you were to look at all the companies in the space this one would have the best design, or this would be one of the top 10%. So if you were to look at something like Calm or Robinhood, okay, they're the best looking app with the best UX of all of anybody in the category.
So Calm was better than Headspace, Robinhood was better than E-Trade. I mean, it just doesn't take our rocket science to look at them.
But when I first explained this to my team, they would bring me companies and they'd say world-class design and i'm like i'm like they're like i really like the design i'm like pull it up and they pull it up and i'm like that's a template from yeah you know like a website builder and it's a stock photo but where's the actual design of the product and they're like oh that's on this product page my product product page i was like okay yeah again that's just like the i mean if this was a bank's website maybe but that's not world class that's serviceable design that's utilitarian design that's okay design that's good design it's not world class so let's if we're going to say world class like a world class performance is different than a serviceable performance world world-class cinematography-class script world-class dialogue that's different and that's and then product velocity is the other one i like so okay we met with this company in june it's now july what's changed about the product and they're like we don't know i'm like okay well let's find out where's their change log where's their roadmap so in the earliest stages you might have revenue or user traction, but you might be able to ask them for their product roadmap. And somebody like Travis would be like, yeah, here, get on the phone with this guy and we'll walk you through it.
Here's what we're debating about on Sunday. We're reprioritizing.
And then a month later, they've like, and then you go like, if we're with Raul, with superhuman. And I was an investor in his company before that report of Raul, like the change log at superhuman, people don't realize like they're like bink bink new feature bink new feature oh boom we fixed grammarly oh bink we have calendar boop oh we got a new calendar feature boop we got this feature and you're like hmm so here's an interesting question we should ask ruffle this we've had on the show three times now product genius like the the parallels between superhuman and figma are uncanny like design led founder like revolutionary design in the software rewriting the entire browser stack in order to get the performance and i remember it being breakthrough when it came out and then the only thing that i can recall being different between then and now is adding a calendar thing that i don't use and a mobile app and iPad support.
And why? Outlook support. You just don't, you know, when you hit command K, you probably know 50% of the features.
Right. Like do you use remind me of this? I do.
Okay, great. Do you use labels? Do you do snippets? I do.
Okay. Yeah.
Which it was all there when I started using it three, four years ago. I think a lot of those things have gotten better and better yeah so it's just that like polish polish polish polish um i really like want them to make snippets multiplayer i want to share my snippets oh yeah i love yeah so i want all of david's past emails they're so nice i don't do email anymore like you Do you do it on the phone? just don't do email i don't email anybody you know we pass i actually do have pass emails from i've been literally creating a collection of how to pass with my team and i'm standardizing that i'm trying to i don't know that i'll be successful and this may be a mistake but i'm trying to just not have i don't end up having a conversation with the company if i'm not going to invest no but you must say hey we are not going to invest you've took a pitch oh no i get it i don't i don't i don't you basically don't take a pitch i don't unless you're going to invest it's the weirdest thing oh that's very weird so you do all your work up front you front load it the deck everything we're in this unique position as you are too but um with acquired we're like you know we have every six months we have six companies that we work with on the show as our sponsors and our partners and we get to know them really well treasury and i'm now an investor in just about all of those companies so so it's not like uh but it's not pitching's growth stage investing.
Yes, it's growth stage. They're clearly the winner.
They're not yet priced as if they're the winner most of the time. Yeah, exactly.
They're going to just keep compounding. Yeah, look, pricing's going to be hard.
Well, depending on entry price. We'll see.
Yeah, I don't know what's going to happen to these companies after, you know, the flat is the new up, but I think, you haircut is the new flat well public comps got hit 50 plus percent i mean they got hit harder again yeah i mean i'm buying equities right now i've been doing it at jtrading.com and um i am gonna buy more sorry about all i picks a couple weeks ago which one whatever i told you oh yeah no no i actually love Taiwan S semiconductor uh and stitch fix was the other one i think you're still no i didn't know twilio twilio was yours and i love that one too and i i like shopify as a pick um i'm actually really enjoying it it's really not investing out not investment advice but it's balancing out my um understanding of what public success is compared to private and so for me it's just a way like am i going to fight with a blaster no i'm a jedi i use a lightsaber but you know but if you learn if you use a blaster it's not as elegant it's helpful it's really helpful if you look at the very best people the best gps like in venture over the past two decades sure they all trade public stocks. Yes they do it for this same reason they're gonna fight with the saber yeah but like they want to know how to also use a blaster or how to fight in the next wing or something like it's not what a jedi does but jedi will do it it also keeps you really sensitive to the public cycles so that like yes it's not that you have to think about the public comps when you're investing but you have to be aware of how much those will change yeah and early stage investing it's almost silly to compare to like my opinion is it's very silly to compare to public comps because the only thing you know for sure is we're going to be at a different place in the cycle by the time this company gets liquid so it's ridiculous but it's helpful to drive into you like how much variability there is when was the last time it was this different that's yeah i'm really enjoying understanding what the founders of those companies go through versus the founders of the private companies that go through what the boards decisions the board has to make of a public company versus the board of a private company yeah so it you know i'd like to join a public board at some point it's probably not a good idea for me to have said that because I might get an invite for one and that might be too much work.
But yeah, especially given the market right now, I better be careful. But you could also invite me to do that.
But it's just, it's been great. Especially through the show now.
You have relationships with public company founders. Sure, of course.
I mean, if I really wanted to, I'm sure I could lobby. Oh oh you don't have to be on the board though you can have a great relationship doing the analysis and i'm doing it anyway with molly every day okay you know twilio's or adobe's come i just bought adobe this week when they bought figment so funny so did i not investment advice not investment advice but i was like they bought figment tanked okay so here's my theory on this they bought figment and tanked and i was like why did why do people hate this and they're like oh no adobe's admitting defeat and that like they can't innovate in house or and to me i look at it like adobe has customer channel and it was foretold five plus years ago that they were not going to build the next figma like that would be a full rewrite of their entire software stack so buying the thing even though they paid a tremendous premium because 50x revenue multiple because of the network effects that figma has um and obviously all the product stuff but if they can get that through adobe's channel like i think that is an absolute win-win acquisition and all these people that are like oh they're gonna.
They're going to kill Figma. No, they're not.
That's why they paid $20 billion for it and have a gigantic bonus for Dylan to stay on board. Yes.
They're taking a YouTube approach. I think everybody in M&A knows now.
Yeah. Like, WhatsApp.
WhatsApp. Just leave it alone.
Don't screw it up. And then, so I like your analysis.
I added to that analysis is, if you're not going to win the war and you can build an alliance and then fight another war, like they've just removed the downside of Figma creating Photoshop. I'd be concerned for Adobe if they didn't buy Figma.
Correct. So the fact that you're giving us a discount on the shares for them doing the right thing is like Christmas.
Like, thank you. You just discounted the right move.
Fantastic. It would be like, people are like, oh, you know, the Warriors signed Kevin Durant.
And you know what? We're going to lower them. Their biggest odds are going down.
We're lowering the cost. But they paid a lot to get them on the team, so.
Yeah, and oh, you know what? We're going to biggest odds we're lowering the cost but they paid a lot

to get them on the team so yeah and oh you know what we're gonna lower the cost of the tickets so 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 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. And what if there's always the internal people who are penciling out that spreadsheet.
Yep. There's a group of MBAs who penciled out that spreadsheet with Figma.
No offense to MBAs who are listening. And they said, hey, boss, if X, Y, if X, Y, Z.
they said you know here's like five potential paths if we make figma free for 10 users and whatever or if we you know take whatever figma costs and then we blend it with the adobe suite okay 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 right right but they may not have all the non-designers right only designers pay adobe right well no they have they have marketing cloud but that's a totally different set yeah yeah only but when you look at figma like i got a figma account like people who are doing giving feedback on designs the business side the sales side can get into figma so i think they got the whole creator class exactly so i think you're opening up the aperture of who design software is for with figma it's for bd it's for the ceo sure the cfo can come in and take a look at the product oh legal should come in and take a look at the product. Oh, legal should come in and take a look at the product.
Yeah, buy them a seat.

So it's like Slack is for the dev team. And it's like, yeah, and the sales team.
And ops. And anybody else might as well be on there because that's where everybody is.
So that's what I think is going to happen with Figma. It's like everybody's going to have a Figma account in the future.
Just watch the product team build the product and put a comment in. And who cares if it's $100 a year? It cost of doing business any 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 a 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 in two weeks ago which was like if they're paying 50x now and the company's growing okay they're paying 20x next year 25x who cares right it's such a high growth company and then i was just thinking well somebody's got a theory there and when i sold weblogs to Aol people were like oh my god these people are idiots they gave 30 million dollars to you know for weblogs inc they've only got 200k in revenue what they didn't realize was aol autos aol tech aol lifestyle those were sold out at like a 90 rpm revenue per thousand pages the ads different CPMs.
So then they would put an Engadget or an Autoblog story or Blogging Baby or whatever other blog

we had on the homepage of AOL.

And a half million people would flow through.

And then they would put those ads on our sites.

And then they would blow out $50,000 or $100,000 in ads a day on a blog.

And those people were like, great, because it was costing aol to make content like 500 per piece of content three thousand dollars per piece of content on aol.com slash autos whatever and we were doing it for at the time five blocks above five dollars a blog post because we said well people can write for an hour so it's 20 bucks an hour and it wage. It made sense 15 years ago.
The internet media game has changed so much. And then I was like, okay.
You guys were doing $200K annual revenue? We had done $200K to date. Holy crap.
Over the 18 months. What is that? I mean, now the world we're in today.
People looked at the multiple, and they were like, J-Cow just robbed. And I was like, okay, no.
$30 million sale? I look like an idiot. What like here's a i look like an idiot five years later and that's the best the best m&a yeah is when yeah you look like you robbed the bank yeah and then five years later it looks like you robbed the founder youtube instagram figma will be in this category like yeah when they bought instagram they're like 30 people work at this company and they gave them a billion dollars.
You guys are morons. And now it's a $150 billion company.
Here's a thought exercise question. Obviously irrelevant because you don't monetize it.
What do you think the enterprise value of All In is? Well, it would do $10 million in... When I was at the Code Conference, a lot of people have been trying to buy it or put it as part of their network, network obviously uh which would kill it yeah my partners are right like let's not make money from it part of part of the delightfulness of it is that we're not trying to monetize it well but but you do get a huge economic value out of it schmack pulled me aside at some point it was like hey schmack like just we're friends like yeah you're all your next fund won't be bigger hey dumbass yeah i was like you know when a friend who can be like, hey, dumbass, like, that's a good friend.
So I appreciate you about saying that. And he's right.
And it's playing out. And we had a rule, no talking our books on the pod.
But we kind of talked about it. We're like, the pod is great when we talk about our bets.
So explaining our bets, not talking our book, is the new philosophy. So like,, Freeberg just talked about his SPAC.
Freeberg still has a SPAC. Yeah, he did.
He just found a target for it. Chamath talked about the healthcare company.
The healthcare company, which is, I mean, we wanted to talk about that because Chamath and I both agree, like, maybe we're, I mean, maybe. Like, we're definitely over-prescribing these drugs to kids kids, like for ADHD and attention drugs, and adults are taking too many.
I think that that's not disputable. I think science is showing that.
So, you know, to make software that could help kids with ADHD is like noble. But I think people want to hear us explain our bets.
So, you know, explaining our bets, I think is kind of a cool aspect of the show. Talking your book is lame, but explaining your bets is cool.
So anyway, in the event, did a couple million dollars, had a small profit. But it was the number one tech event of the year by far.
Right. So I'm kind of bummed that Freberg's a little bit of a blocker for it, but I might turn him around and we'll have a vote maybe in the fall another one oh well i'm going to do another one the question is am i doing it under the all-in brand or do i have to create a new brand for it yep and so i told the guys i said i'm gonna do it again well code conference is done so like there's a vacuum conference is done yeah they need a new host um that's crazy like it's such a valuable...
No, no, I talked to Bankoff about it,

and he's been very public.

You know, Kara Swisher, I think,

is going to do the pivot stuff

and wants to do other stuff.

And, you know, she's...

I really respect what Kara has done,

you know, in terms of, like,

she does stuff,

and then she moves on to the next thing

and tries.

Like, you know,

it's kind of my approach as well,

which is, like, Bob Dylan, you know,

said, like, don't look back kind of thing,

and he always tried to make the next album

and forget about the past one. And much to the chagrin of people who loved him as a folk artist and didn't like, you know, said like, don't look back kind of thing.
And he always tried to make the next album and forget about the past one. And much to the chagrin of people who loved him as a folk artist and didn't like, you know, like a Rolling Stone.
And when he went electric, they booed him. You know, I was like, really? You're booing Bob Dylan because he's using an electric guitar? Are you guys dumb? Like, did you hear all along the watchtower? Like, this is incredible.
And so I think, you know, Kara Swisher, like moving on. But Jim said he's going to keep doing it.
doing it and you know it's probably a small list of people who could actually host that credibly you know a very small list um and so which you're definitely on i am you think how could you not be i mean i'm not even saying that to like make you feel like no i'm joking okay okay you're you're joking about being humble had that kind of prestige, it seems like Friedberg would want to do it. It seemed more like the thing he was averse to is the like.
Yeah, I mean, whatever the issue is, like we've had our issues. We all have issues.
But I think there's basically two possibilities for all in Summit. I'm going to present it to the boys and say like, here's the plan.
Yes or no. And we we agreed we'll put it to a vote.
So we put it to a vote. If three of us want to do it, we'll do it.
And if two of us want to do it, then we can't. And Freeburg already said, if you do it on your own with a different name, I'll come and support you and I'll show up to do a talk or do an interview or whatever.
And I was like, great. So I'll do it with a different name if they don't want to do it.
And the fans can decide if they want to come or not. Partially in.
Partially in, exactly. So, you know, it's up to the boys if they want to do it.
But it was like a pretty great success. You already have call-ins.
Well, yeah. And I started doing a call-in show called After All In for the last two episodes where I took calls about the last episode of All In.
Just to support David because I don't think people remember how great that app is. It's really made great progress.
So I want to be supportive of him. And I have a small investment in it.
I'm very meaningful. On the one hand, this is ridiculous.
On the other hand, it might be ridiculously low. It's worth $50 million, to answer your question.
$50 to $100 million. I mean, as a top 40 podcast, it's worth at least $50 million question 50 to 100 million i mean as a top as a top 40 podcast it's worth at least 50 million on its own though but i mean like economic value that the four of you oh who knows over the lifetime like if chamath or sax or i or friedberg were to get but one more deal out of it and it's an uber right the economic value is nine figures right possibly 10 you know like so yeah that's the thing like i think like man weblogs like you were doing 200k of revenue you sold it for 30 million pretty great takeaway yeah and now look at this like you know yeah i mean listen i hope it keeps going i hope we can keep it on track and um you know i i love doing pods this week in startups is a juggernaut as well you know yeah that was out for 10 years.
What is that, like a quarter million listeners or something? Yeah, something in that range. I mean, it's hundreds of thousands per episode.
It's a very niche podcast. I'm not trying to make it all in.
I'm trying to make it for founders. And so in order to make it bigger, it'd have to be worse for founders.
That's what we. And so we talk about what we think about with our show.
I want founders and capital allocators to listen to it. Okay, listeners, now is a great time to introduce a new friend of the show who many of you will be familiar with, Claude.
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. Yep.
We're excited to be partnering with them because Claude represents exactly the kind of step change technology that we love covering here on Acquired. It's a powerful tool that fundamentally changes how people work.
I know, Ben, you have used Claude for some Acquired work recently.. 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.

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.

I just got my most important hundred dates for the episode done in like 20 seconds. You texted me to this table.
It was awesome. 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.
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. Listeners, stay tuned to hear all about that.
Yes. So listeners, by using Claude as your personal or business AI assistant, you'll be in great company.
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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.com.
Or click the link in the show notes. I'm not trying to move up the rankings.
I don't mind, you know, hanging with, you know, all in being number one in tech and then hanging out with you guys at, you know, slumming it at six to 15 with you guys in the rankings. It's like, that's where we belong.
Look, I got number one on lock. But who's counting? Whatever.
You know, like, that's where we belong with these things, right? Like, it's a niche podcast by definition, right? Like, it's not supposed to appeal to everybody. And you try.
If you want to appeal to everybody, like, read the Bible. Like, that the bible like that's right if you go to this is the beauty of the internet reads bible passages and he and huge it's like if you can literally true crime true crime religion read the bible or ben shapiro dunking on libs the end that's like that's how you do it or do it daily but joe rogan's out right he's on spotify right right you know he's not in the other rankings so i mean or do a daily news program for 20 minutes like but that's not what i want to do i want to talk for an hour or three about deep topics in founders and catalogs would be a fun acquired episode is uh howard stern i feel like it's underappreciated how much howard stern i copied my that's the playbook that should be the next Taylor Swift type episode that we do.
Yeah, no for sure. He wrote the playbook for all of us.
I literally took notes for it. King of all media Do you know him? I have never met him I'd love to at some point.
I have a lot of respect for him I mean obviously he did crazy stuff when he was young and that shock jock stuff but he in his later years became a great interview. Great interviewer Great interviewer.
He really refined his technique I really appreciate that about him and he created characters sound familiar yep he branded them yep he showcased them the whack pack you know all this stuff did he ever do a event 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 So yes, he did the equivalent of those in New York.

But it was a very New York thing.

So he played tennis against Baba Booey.

But he got 10,000 people to show up and buy tickets to a tennis match that they pumped up for whatever number of months.

I remember this from my childhood.

And then he did his books, which were phenomenal.

And then 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 uh the process of doing a reality show right now so literally gonna do are you really yeah i mean just you or the besties or just me um the besties don't want to do it they don't have time for it i mean there was there was talk of like maybe all in you know kind of going on to one of those services like people had reached out like hey would this work you know? That's a lot more work though.
Well, we would have to show up in a location. We'd have to do it weekly.
There'd be some format, some shiny floor, whatever. It's a different beast.
I don't think they have the time for it, if I'm being honest. But for me, I would like to do a reality show in the Gordon Ramsay kind of vein, you know, where I'm helping founders.
I think it would be great for Reach. So I had done a reality TV show with NBC and the Weinstein Corporation.
Oh, wow. Yeah.
And it didn't make it on air, but I have the— You should be a Shark Tank judge. I had been—they had reached out before.
Mark Burnett had reached out early on when it was Dragon's Den. Right.
Before when they were going to bring it here. So when it was Dragon's Den, they had reached out before mark bernard had reached out early on when it was dragon's den um right before when they were going to bring it here so when it was dragon's den they

had reached out early but i wasn't very successful back then um i wish but you know i think now i

think i would have the credibility and the advice to give that i could do a gordon ramsay style show

that would be very entertaining and educational and be completely different than you know the

fundraising aspect and the pitch aspect of shark tank so i'm not going to do that. But, you know, I've got, you know, the I won't say which one, but a very major, the major, you know, reality TV folks reached out, I think, in part because all that was doing so well.
Would founders and companies feel comfortable? I feel like a really amazing window and insight would be the type of conversations that you have with a founder as they're building the company. Would founders and companies be open to that? Yeah.
So the NBC show I had done the pilot for, which never made it on air, what was really good was really about me incubating companies. And they spent like $400,000 or $500,000 doing the doing the pilot it was really good and it would have been a big hit did did it get canceled because of the heart of leinstein stuff wow so they were just like anything that was in his company all the ip is dead because he's a monster and so anything associated with it but you got to remember he did project runway so he had done some of these giant shows people don't know know that about that.
That's right. I forgot.
Yeah, that had the TWC at the beginning. So, you know, NBC bought the show in the room, loved it, and did the pilot.
It came close. And Chamath was on that episode, actually.
He did the pilot with me. Oh, my God.
He was like my VC friend who came in. My VC friend.
No, it's hilarious. But I'm excited to do it.
If it works out, it works out. If it doesn't, you know, no skin off my back.
But I like the media space. And then, you know, 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.
I'll be gone soon. Well, you know, you never know.
And, you know, I've had you never know and uh yeah you know you've mentioned your friends yeah i have two friends who died young and i'm just like i you know i talked to my wife i was like i don't know like what if i make it another year or make it 25 years but i want to make it count i'm not going for max dollars like and so when the guys break my chops about that i'm like guys it's, it's not my priority. Literally, maximizing money is like...

Well, also, you're probably at a point now where...

It's literally not in the top ten.

What is more money going to do?

It seems unlikely.

You're literally going to change.

It's not something about my life.

You don't want to play.

You guys understand my life.

It is ridiculous and charmed.

I can do whatever I want.

I have enough money to do whatever I want.

My kids are fine.

I can have whatever I want.

I don't care about a third home.

I have a ski house.

I have my regular house. It's good.
I'm good. My kids have their college paid for i'm good like 100 i literally do not care about do you feel like that's a demon that you fight is like no any allure toward no i had it when i was younger i wanted to be powerful i wanted to be important i want to have money i wanted to be seen i wanted people to recognize my greatness like any person recognize me for what i do i got all that it literally does not even come up my radar to have more money is the last thing i'm thinking about i do want to have i do want to you know be the greatest investor of all time yeah like to me that's meaningful or be one of the i want to be like i know i'm mount rushmore for angels yeah i want to be mount rushmore for investors.
So when you guys do your thing in 10, 20 years, it's like, okay, you know, here's Doug Leone and Moritz. And, you know, here's, you know, John Doerr.
Here's Gurley. Like if we are making a Mount Rushmore.
You want to be on that with them. I would like to make it there or at least be in the conversations.
All right, listeners, we kicked Jason out of the room again because we have our next sponsor of the episode, our very good longtime friends over at tiny Berkshire Hathaway of the internet. If you'll recall, indeed, indeed.
So there are so much so the Berkshire Hathaway of the internet, as we told you about a few seasons ago, they literally built a business on the internet selling busts of Warren and Charlie that you can order. Berkshirenerds.store.
Berkshirenerds.store. That's not what we're here to talk to you about today, though.
They've got something new to share with us this season that we've been talking a little bit about kind of from the founder angle, but we want to share with you from the VC angle. Yeah.
So the core business of Tiny is acquiring wonderful internet businesses. These are businesses doing 5 million or more in revenue at 30 to 40% operating margins.
Well, and the DNA really comes from Andrew and his partners originally running MetaLab. And of course, it was a very successful, it is a very successful design agency that started spitting off cash.
What do you do with the extra cash? Well, they know how to run a great internet business with MetaLab. And so they started buying more and more and more businesses.
And so now with this awesome portfolio, Dribbble, Pixel Union, Creative Market, 8020, Girlboss, these are all tiny companies. And so what are they doing differently now? It's funny.
It's different in a sense, but it really is the same tiny playbook that they've always been running to buy wonderful internet businesses. But something changed in the last five years.
We were in this crazy go-go era where lots of businesses, even ones that really aren't the shape of what venture capital should be funding, well, most venture capitalists were funding those businesses too. And so you end up in this situation where you've got a lot of companies that have raised a lot of money that probably aren't tripling, quadrupling year over year the way you would sort of expect a venture business to be doing to raise their next round of capital, especially in this environment.
And so if the business is growing, you know, 20, 30, 40%, and it can get profitable or it is profitable, well, most of the time- That doesn't really make sense in the context of a venture portfolio. Right.
But the founders probably want to keep running that business. They probably want to keep serving those customers, doing their life's work.
Exactly. And you end up with a lot of these companies in a portfolio that are capable of being tiny-like businesses, but are not going to provide a big exit that's going to move the needle for the venture portfolio.
Well, Tiny realized they can provide the perfect solution to this problem for the VCs on the boards of these companies, for the founders running these companies, and most importantly for Tiny to then come in, partner with these founders, and own these companies in perpetuity without looking for an exit.

So really what Tiny can kind of do is come in, buy the company from the VCs, or a lot of the company from the VCs.

The VCs get their money back.

Some or all the money back. And most importantly, get their time back, get off the board, so they have capacity to do new deals.
So it's great for founders to keep doing their life's work. They can figure out a structure with Tiny.
Tiny is very good at figuring out structures that make sense to align interests. Yes, they're incentives and masters.
Yes. It's really super cool.
Honestly, I've talked with a with a bunch of folks varying different financial groups and institutions over the years who have had some version of this idea and it's never gotten off the ground. And I'm so glad that Tiny is now doing it and they are the perfect ones to do it.
And this is the perfect time to do it. So very excited for this to exist.
Yes. Well, if you are running a business like that

or you are invested in a business like that

or your friend is invested in a business like that,

you really should shoot a note to hi at tiny.com

and just tell them that Ben and David sent you.

Don't tell them Jason sent you.

He's not here right now.

You can say Jason sent him too.

All right.

Our thanks to Tiny.

When you guys are having the conversation in 20 years and i'm gone or i'm retired and you're saying mount rushmore imagine you retiring yeah it was possible um i met don valentine when they were like you know he was not active investment but when i pitched mahalo he was in the room he came up i talked to him he was oh he was still hanging out there all the time yeah um yeah like why retire um he was just awesome oh um but you know if you had that conversation right now about mount rushmore like you gotta okay so who's who's on your mount rush well i mean you gotta have don valentine yeah right that's just not possible but how are you scoping it because you probably need paul graham too well yeah i mean you got paul graham is in the running for sure but that's like a number of startups but there's a lot of big ones in there. You have big impacts.
So Paul Graham's definitely running. But OK.
So do you go with John Doerr is in there along with. So if you're doing firms, it's a lot easier because you get Kostla, Doerr, and Perkins, Tom Perkins.
You get the three of them at once. You do Sequoia.
Which people, Vinod Kostla spent a decade at Kleiner Perkins with John Doerr. Yeah, and you had...
You look at that firm, that's like the OKC with James Harden, you know, whatever. But then you have Doug, Leone, Mike Moritz, and Valentine.
Jim Gratz, Ruloff. Well, Ruloff's next generation.
But you put the same time for those 30 years and it's like well that's mount rushmore right so if it's a mount rushmore of mount rushmore's is kind of how you might look at it you know you definitely have to have we just did benchmark you gotta have the fab four era of the fab four era of benchmark was truly something special yeah it's kind of like it kind of builds itself the mount rushmore right now right it's it's going to be sequoia kleiner benchmark and then we're like we're going to have a big debate on the fourth arm right yeah like is it well it just depends how wide we're willing to scope it is it like traditional series a type venture firms or is it angelus naval right that's had a huge impact do you put yc in there do you put yc or tech stars both have a huge impact do you put um you know uh who else could be in there that's just you can argue for founders fund you can say yc and tech stars not yet the founders completely different things on the way what yc is like yeah for sure i mean three orders of magnitude for sure they've done the same number of companies i think but just in terms of terms of returns, yes. But Techstars, I think, was a little before Y Combinator.
But anyway, you definitely have Y Combinator in the running for that fourth spot, I guess. And then who else would you put in there? Masa? Or Yuri Milner? That's high beta.
Well, no, I mean, but in that impact on the industry? Maybe, I mean, Excel, I don't know, depending on... Excel would be in the running, for sure.
Ron Conway. i think the way you kind of have to define it which is unfortunate because it means that it's gonna be a long ass time before your firm hits mount rushmore is three successful generational transitions where each of the generations would have been on mount rushmore all right so then let's just do this instead of mount rushmore because you're we're talking firms so for firms you do mount rushmore? So I think if you were just going to say the Hall of Fame.
Yeah. Oh, yeah.
Just the Hall of Fame. Yeah.
And the Hall of Fame has, let's just say. Oh, dude, we should open the Venture Capital Hall of Fame.
Venture Capital Hall of Fame. The Venture Capital Hall of Fame.
Capital Allocator Hall of Fame. Top 25.
I was trying to figure out when we were doing the benchmark episode research, which will be out by the time this comes this comes out. 2480 Sand Hill Road is a very special building.
It was the Forethought PowerPoint. The Quadris Complex.
Quadris Complex office. Then it was Microsoft Silicon Valley.
We're the only three people who make shit about this. Oh, no.
Three of us are so excited right now. This is the internet.
This is the internet. It's like, wow.
We've aggregated all the other people. Everybody else who cares about this is listening right now.
And like Sebastian, who wrote the Parallels, you guys are taking this way too seriously. It's not that important.
We're like alone yelling in David's house about a fictional Hall of Fame. TVI, Meryl Pickard.
TVI. That's a good deal.
August Capital, Benchmark Capital, Shasta Capital, all in this same building. And I think there's some space for rent in there.
I don't want to go live down there, but I think we've got to take out a lease just to put the museum. The whole thing.
A Venture Capital Hall of Fame is something we should grab right on. We should just do it.
That would be pretty fun. Fuck it.
We'll just do it. Yeah.
We'll do it like every year. We induct somebody.
We'll get up there, the three of us, and be like, this year we're inducting into the Venture Capital Hall't know how it exists hilarious you know cooper's town there is a um what do you call it there it'd be our cooper's town yeah there is the computer history museum but it's for the pc which is totally valid right right it's not for capital allocators it's not for people like there should be a hall of fame and do we do we Midas-list style ask people for the real hard truth numbers?

No, no, no.

It's about impact.

We decide.

The three of us.

We decide.

It has to be impact on the game.

Does the NBCA have a Lifetime Achievement Award?

Is that the closest thing?

It doesn't really exist anymore.

It's about impact, legacy, the intent of the person.

This is why Paul Graham would be first ballot. is why yeah okay who are the first ballot entrance so obvious we've already talked about it we've already talked about 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 this is 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 you gotta be you're not playing in the league anymore so paul graham's still playing in the league does jeff bezos count like well i mean how many investments has he made that google investment is crazy so there's that but there's also like i think amazon is the best venture firm of all time and just in terms of like it's internal oh they're not separate companies but like yes capital allocating, lowercase a.
They've been great at placing bets. But you're right.
Jeff Bezos is probably the most successful angel of all time. Yeah, I mean, if you just did it on dollar.
And LP. Yeah, and LP.
When you're looking at it, I think you've got to look at impact. Like impact on the game, legacy.
So is Carmelo Anthony Hall of Fame? Of course he is, but he didn't win a ring. But he's Carmelo he's Carmelo Anthony, right? Or Charles Barkley.
He didn't win a ring, but... Okay, so then we got, like, Arthur Rock.
You got to look at, like, the founding father type. Of course, of course.
Yeah, there's no doubt. I mean, that's like going back to Bob Cousy or whatever.
Going back to, like, some really, like, you know, people who built the league kind of situation before it became the league, right? So you got the league, and you got the people before the league, you got people in the league yeah you can generational shit right here you know patrick ewing yeah you know because i think like you look at girly like he's part of that patrick ewing generation right like that him elijah on charles barclay generation yeah 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 but if you started before 2000 it's a different group do you notice we haven't talked about entries and harwitz in this conversation no impact on the game they're in they're in both of them are in for sure no doubt they totally are i guess impact on the game totally changed i mean i just feel like it's gratuitous it's just like raising 10 billion dollars three funds a year i want to see what happens with the crypto stuff i think they're just an index of venture i find it quite soulless if i'm being honest like i feel like it's a giant index on venture and i don't think that their hearts are super into it well i do think they have interesting ambitions though i think this like that's the problem it's more ambition yeah it's more ambition than soulful but there should be a jp morgan or a goldman sachs silicon valley and there be for sure i don't know yeah why is it why does goldman sachs manage the money of entrepreneurs i just feel it's too okay fine but i just feel like it's it's too it's it's like too premeditated and less soulful i i feel like it's a soulful business where like your intentionality and your relationship with the founders really matters it's not the craft it's i mean it's like the literal antithesis of it's industrialization it's the yes it's the industrialization of it it's the it's the factorization of it and listen i'm sure it'll be very successful at the end of the day all the returns will be great except for the crypto stuff well i mean there'll be mean reversion because like when you get the law of large numbers you have mean reversion exactly it will be mean reversion for sure i mean that was at some point they leaked a lot of their returns and they were like 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 gonna i think in the arc it will not be comparable to benchmark and sequoia and we i mean made a lot of hay of the fact that they had, that they made $11 billion in profit on Coinbase. And like, I do not think they sold out of that.
So they did not make $11 billion in profit. Fair enough.
Well, I mean, it's timing is everything. We'll see.
I mean, it's interesting too. I mean, having just done this benchmark episode, like the Benchmark Fund 7, one of, if not the best institutional size fund of all time.
Just like unreal. 20 to 25 bucks.
like the benchmark fund seven one of if not the best institutional size fund of all time just like unreal 20 to 25 that like the the fluctuation in the marks on that fund and it'll probably probably end up between 15 and 25 x maybe but like but it fluctuates up up and down so much of course i mean it's we live in a very volatile time right now so yeah i like the hall of fame idea it's kind of interesting i think we actually would be a fun thing we should get some space on Sand Hill and put up a... No, we live in a very volatile time right now.
I like the Hall of Fame idea. It's kind of interesting.
I think that actually would be a fun thing. We should get some space on Sand Hill and put up a...
No, we could just do it as like a dinner. We just literally have every year.
We don't need a space. We could just start in a restaurant, but you could get like a little hall and say, we're going to induct into the Venture Capital Hall of Fame the following people.
And here they are. And we just have three pictures.
Boom, boom, boom. And you just drop it.
And it's like, here's our three people. And then people come up and say something about the person.
And I think like we could do like the three who we would hope would be there. And then we'll have like one or two post-tunits.
We do it like the sports where you have the person who's being inducted chooses who inducts them. Sure.
Oh, that's fun. Yeah, so Ruloff does Doug or whoever does Moritz.
Yeah, yeah. Sean Parker does Moritz.
Mike chooses who, you know. Yeah, he could have Larry and Sergey come up.
He has Jason Calacanis come up and be like. No, no, he doesn't have Larry and Sergey come up, obviously.
Yeah, totally, totally. John Doerr would ask Bezos.
I mean, it's a killer. It's a killer idea.
I i mean we just do bezos yep doug and mike yep and then who would do one in memoriam yes we would do one in memoriam you know whatever yes 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 yeah you do a combo you do a combo maybe it's four people a year you know you have to think how do you you want to get to 25 so maybe it's you want to get to 25 to 50 over 10 20 years so yeah maybe it's three a year in order for this to like feel good i think you're right that it has to be about impact not about returns no returns is like so that would be like saying it's like albums sold for the rock and whole full of fame right there are people that'd be a very andreason harrowitz way to do it oh what's the total assets under management you know and it's like okay dude we get it yeah nickelback sold a lot of albums yeah they're the nickelback eventually no i didn't mean that i wasn't talking about it oh god oh god oh god like a mill'm not saying that there's like oh boy there's you know if you were to look at ron conway does ron conway who had a bigger impact ron conway or indrescent like i think it's a conversation you know and if you because ron conway when i came into the industry like there was at one point i was at a the Crunchies, and Ron Conway, at one point, somebody said, hey, can everybody stand up who said Ron Conway invest in their company? And 100 people stood up. And my mind was like, oh, whoa, angel investing's cool.
I mean, I wasn't an angel investor at the time. It was long before I became a scout.
But I always remember that moment that moment when like a hundred people stood up. That that like inspired, partially inspired.
It was inception. Is that what gave you the, is that what like put you in business as an angel investor? The scout is what put me in business.
Yeah. What happened was I had.
Was your Uber investment you personally or was that Sequoia's money? That was Sequoia's money. Okay.
And we were like, Rulof and I were trying to figure out like, do we let people know we're doing this or not? It was like big controversy at the time like we want to keep this stealthy but I mean Travis knew but you know it was it was a pretty great deal you know it was like um wow you know at the time they carried 50 50 50 at the time yeah they dropped it down after that I bet it's like every time I'd see Doug Leon he's like 50 and they had 30 percent carry at Sequoia at that point I think yeah I mean if I were you I'd be like 50 percent carry to them can't believe it doug would always this they're so classy doug always made a joke would always make a joke it was like 50 carry oh god we get 30 you get 50 this is funny we get 30 we get a lot of pretty funny we're very lucky i think if you look at what we do as capital allocators, I think it's a very special part of the—it's a very special function in the world. I take it very seriously, as you do, for the retirees you're investing on behalf of, but also 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. Yeah, exactly.
So the human species getting moved forward by, as Steve Jobs would say in those commercials, like this is the crazy ones. They do need fuel.
They, you know, maybe don't have an idea of, you know, you know, if they should even build this company. And I think the capital allocators really come in and say, here's some fuel, you know, here, go fight that war.
You know, it's fuel and it's belief, too. I mean, your story about Calm is not uncommon, I think, amongst founders.
Oh, my God. I mean, look at the stories about Don Valentine and Atari and other places where he was at Cisco.
He's like, we got to get this thing back on the rails. This thing's going to zero.
There's a lot of existential moments where things go to zero. So can I ask you, as we start to drift toward the drift toward the end of the episode here that's your line that's your favorite line drift that's that's the ben's signature line here toward the end of the drift towards the end of the episode is this a good format together like is this different enough from our normal show should we do this yeah i think so yeah do you like this i think a casual glass of wine and just you know, if you have friends of the pod and you want to go deep and talk about them in a more casual way, sure.
Yeah, I mean, I think it's a great way to just have somebody on again, you know? So if you profile somebody, like, I forgot that you had done, like, the first episode with me. And that was more about my career and more details.
And so I'm starting to tell stories over again. like well let's talk about some other stuff right yeah so i think it's a different context our audience was i like this i like this format well part of what we you know like lex has done so great with his show yeah but but those type of conversations but i feel like that's more what's the right word our shows are about the business of tech yeah no his is intellectual dark don't know why he's in the tech vertical but i like the format and like kevin rose used to do the foundation series and like yeah i mean long-faring interviews like howard i mean i think joe rogan stole it from howard yeah and i think it's now lex stole it from joe or i don't even say stole i think you know inspired by yeah so lex is clearly inspired by joe and joe was joe was in the running to replace jackie martling on the howard stern show people don't know this so really he was very enamored with stern and uh he wanted to be stern i think and he eventually has supplanted did become Stern.
Yeah, he did become Stern. And so good on him.
Yeah. Right down to the Sirius, Spotify, like right down to it.
He became Stern. Doing a platform deal.
Yeah, doing a platform deal. Which is what Stern did.
Stern had multiple platform deals. He did syndication first.
Then he did the Sirius XM one because it was a new platform. And he used his number one show to build their platform right which is i think what uh yeah which is but actually bring it all the way full circle back to charlie rose like yeah he was like a you know business i mean he did more than business but like he would have culture business anybody in new york because new york everybody in new york was pretty fucking interesting so yeah yeah you know he could have somebody from wall street a publisher an author of somebody who does films you know he would have like spike lee on it You know, he'd have Woody Allen on.
He would have, from Wall Street, a publisher, an author, somebody who does films. He would have Spike Lee on.
He'd have Woody Allen on. He would have any actress on who was doing something interesting, any novelist, Margaret Atwood, anybody, which was coming through New York on a press tour.
You would do your press tour, and then you would just go chill with Charlie, and you would get to do something long for him. It was like a little like sort of more jazzy, you know, a little bit more like acoustic.
So I like this format for you guys. Do you listen to Smart List at all? Do you know about that show? I have listened to one or two episodes.
It's Bateman, Will. Arnett.
Arnett. And then somebody else.
Yeah, the guy from Will and Grace, Sean. I don't know who that person is, but they bring on a surprise guest each time.
And the other people don't know. Yes.
So they're not prepared. Yes.
And it's like Katy Perry. It's like Chris Pratt.
Yeah, it's become a big deal. I kind of want to do that of tech.
But like. Wait, you and I don't know who the one of us is bringing somebody.
You guys are not good. You can't make.
You got to know the person's background much better. But they all seem to know.
Because the celebrities carry a certain charisma with them that our industry doesn't have yeah but maybe it doesn't have to be a surprise as much as like well that the other thing is that it's even though they have guests the show is actually about them the guest is a prop in a way yeah i guess i've only listened to one or two you know i see it in the rankings like it does incredibly well like it's a top 10 or top 25 podcast. Is it part of a network? Is it part of Spotify or something? I don't think so.
I see it on iTunes very high. I don't think so.
It's really weird that Spotify doesn't allow Joe Rogan and call her daddy on iTunes because the advertising would be huge. Right.
So why not bake the ads in and them over there's some nba that's run the numbers that says it's more valuable if it's driving new subscribers i guess that's it i guess that's it yeah oh i guess you know what they want to be able to have those new subscribers so when they go renegotiate with the yeah music i saw they're doing audiobooks too now that's the next piece yeah that is the next piece yeah they're doing audiobooks one-off purchases smart i mean audio is great all right it's getting really hot in here it's getting so hot for those who don't know we're in like a sauna a new yeah it's david's new house david just moved david's got a new empty house we there's no air conditioning here it's sort of like the shining there's no furniture we just feel like this is all from Craigslist. All of it.
Literally in the last two days. That explains the smell.
That, all right. You could have, I mean, listen, you're rich, dude.
Just go on and buy some Crate & Barrel. We can't all be Jason Calacatus.
No, come on, man. I know those fees.
Oh my God. I love Craigslist.
I love Craigslist. I love it.
You buy used furniture on Craigslist. All the time.
I do not buy new furniture. All right, let's got to stop.
I bought a temporary couch on Craigslist. It's the thrill of the market.
You're going to get robbed. Don't do it.
It's too crazy. Craig Newmark, I love you.
With that, our thank you to Vanta. Vanta.com slash acquired.
Vanta.com slash acquired. Our thank you also, you don't know who the other sponsors are because we haven't we don't know who the other sponsors are because we felt very strongly that it was we wanted to make better use of your time do you want to read our Brex ad? they don't sponsor my pod so no maybe they have I don't know there's also a.
Brex, yeah. I know a lot of people who use Brex.
I think we use Brex at one of my companies. If you're enterprise, if you're global, by far the best corporate spend management.
It's much more than a card now. Yeah, for expenses and everything like that, right? And then they've kind of expanded behind that.
So you can give cards to each of your employees. And then if they screw up, you can turn it off or something.
Yes, exactly. They jump the fence.
Pre-approve some budgets. Yeah, you don't want people jumping the fence and going crazy all the listeners know because they they heard it like an hour ago they're very familiar oh that's in here yeah so anyway thanks shout out brex so that's brex shout out brex and then use the promo code twist we share we share this uh last sponsor these are these are great folks these are these are like dear friends and and geniuses and raconteurs master Masterworks? No, no, no.
Good guess, though. Think smaller but bigger.
Smaller but bigger. Literally small.
Gosh, I can't believe it. But secretly huge.
Tiny. Oh, tiny, of course.
Yes, they're buying companies. They're buying companies.
They're doing a good job. Yes, they're creating like the Berkshire of the internet.

And can you imagine a better time to get the monkey off your back of venture capital?

Yes, sell your company.

Secure the bag.

Secure the bag.

That's our favorite J-Cow line.

Secure the bag.

Let's go, man.

Trust me, if you haven't secured the bag yet, it's a wonderful experience, man.

There's nothing like getting home with the bag.

You get that tiny bag.

You get that AOL weblogs exit. Oh, man, let me tell you something.
I'll tell you the story. What did you do when you secured the bag? I'll tell you what happened.
It's a funny story. I'm in my office, and I got Bank of America, and I got, like, low thousands of dollars in my Bank of America, and I got an American Express card with negative 10 on it and a Visa with negative 5 or 10 on it.
And I'm there and they're like oh wires are good you know the bd people are well and so i'm like hitting refresh yeah on the thing this is 2006 seven five six yeah i'm hitting refresh i'm hitting refresh and then bing bing bing bing bing you know all the numbers come in for the whole you know amount and you own most of weblogs uh brian and i were equal partners then we had peter rojas had some ownership and then mark cuban was our big investor uh and by big investor he put 300k in for five percent so that was a great outcome for him uh oh wow yeah uh or more maybe on 10 i think on 10 anyway long story short uh my wife comes in she said you okay and i said what she said are you crying and i reached up and i had a tear in my eye you're like this is a new experience i've never had this before and she said i said she said why are you crying and i said i'll never my family will never have to worry about money again because i spent my whole life worrying about money yeah you know my dad had lost the business everything was a very cathartic thing for me and i think people you know who are already rich uh you know or maybe who come from means just they don't understand the concept of living with the fear of being broke and in debt all the time and then when you have the bag you secure that tiny bag and it's a tiny bag but it's filled with diamonds and cash and you just open it up and say thank you tiny thank you tiny for securing the bag acquire.fm slash tiny no it's literally they don't give us a thing oh they don't we don't know that's right uh email uh is it high at tiny uh and tell them about whatever it is like just know that tiny tell them that them that Ben David and Jason. You can mention Jason.
But 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. Then I tried to buy a Ferrari.
They wouldn't sell it to me in Beverly Hills. What, like no new money or something? Yeah, basically i went in there and they're like oh yeah what am i like to buy a ferrari uh today in 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 an answer on the waitlist so i said to this guy can i ask what do you do here he's like we sell ferraris i'm like to who this is actually no this is part of their strategy it's part of the strategy part of the they have the ferraris but they don't sell the ferraris to build we're not putting on your list i was like well how long is the wait list he's like i was like okay i was like i'm a cash buyer he's like everybody's a cash buyer i'm like okay um uh can i ask you a question then he's like sure come into my office with like espresso you want some Pellegrino I was like like, espresso.
You want some Pellegrino? I was like, no, I'm good. You want some Pellegrino? Like, let me offer you a Pellegrino espresso.
And I was like, I was like, I have the same one touch. Sure.
And this Italian guy is like, I was like, I don't mean to be rude, but what do you do here all day? He's like, well, we deliver the cars and we service them and we sell used cars, pre-owned, certified. For more.
And I was like, oh. I was like, well, I would like oh well the one you're looking at is pre-owned i was like no no no the one i'm looking at the 430 the red one out there that's the one i want that's got a sticker in the window he's like yeah no we certify them we put the sticker on the window i was like oh well that goes for 230 000 or whatever and so uh yeah what do you want for it.
He's like, 300. And I was like...
You're like, the sticker says... No, no, no.
This is the protection of the...

I said, the... 230 000 or whatever and so uh yeah what do you want for he's like 300 and i was like you're like the sticker says no no this is the used one i was looking at he's like you can't get these cars and i was like so you pay over 70 000 he's like it only has 2 000 miles on it and i was like 2 000 miles it's 70 000 more than new i said why wouldn't i buy a new he's like because you can't get them and i just i'm such an idiot from brooklyn who doesn't understand the concept that people would pay over for the car and i'm just perplexed that would bother me i was like all right well let me think about it i laughed and and then i was with my friend and i was like um and i had the rob report and it said like number one car was the ferrari f30 that turned the page was corvette C6 was was the number two car and the starting line was make ferrari buy two for half the price of a ferrari and beat them off the line or something like that and i was like let's go to the court let's go to the chevy store let's go to the chevy store i walk in there's corvettes everywhere the guy looks at me he goes you want to buy a corvette i said yeah he said if you buy a corvette today i'll give you five thousand dollars off i was like yeah so we go out on the 405 and we're driving the corvette and he's like this is a corvette son like you're going 70 miles an hour i'm not i said i'm not he says i'm not selling this car to you unless you hit that gas much harder and i said okay and i punch it to 100 miles per hour the guy, yeah, how does that feel? I'm like, great.
I come home with a Corvette. I come home with a yellow convertible Corvette.
My wife's like, what happened to the Ferrari? I was like, this thing only costs 65 grand. It's like 70 and I got five grand off.
And it's American, baby. And it's American.
And that was the car that I famously was, according to Gawker, Robert Scoble, myself, and Elon, when Elon got the first P1 of the Roadster, he was like, I got it. I was like, oh, let's meet in Brentwood.
And we were driving them at a... You were racing.
You were racing. We were driving them along Sunset Boulevard.
A spirited drive. A spirited drive along Sunset Boulevard.
And we did it like five times. And five out of five times, the Tesla just destroyed the Corvette.
And I was like, I'm doing something wrong. And then we switched cars.
And I was like, nope. Electric is going to beat everything.
And this was the first one that was the prototype. That's in space right now.
It's the cherry red one. That's in space.
Oh, that's the one that's in space. And there's a famous photo of me and elon in front of the corvette uh with that that one's it but there's a famous photo of the two of us uh you know in front of my corvette and his p1 uh and i remember that night like it was yesterday because we were just before the iphone you realize like robert scroba was recording this on his nokia you know these are the memories right like crazy the journey that you've been on yeah it's pretty this is the stuff you just will cherish forever my life is unbelievable i am so grateful for it and uh thanks for having me on the pod guys listeners thank you so much acquired.fm slash slack come join us we'd love your feedback this is cool this is a new shtick yeah acquired.fm slashm slash store.
You can buy cool shirts. Swag.
Slash jobs. Find your next career experience.
Acquired.fm slash Craigslist. You can get a couch.
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 it. Let's go eat some food.
Let's have some sushi or Mexican. I don't know what we're going for here.
That was awesome. Oh, so fun.
Thank you so much. Of course.
All right, listeners. We hope you enjoyed that very first Acquired Sessions with Jason Calacanis.
It's a new format we're playing with. We would love your thoughts.
AcquiredFM at gmail.com or tweet at us at AcquiredFM. I am curious what you liked, what you didn't like.
And on that note of feedback, we have something that we really, really want you to participate in. No pressure or anything, but it would mean the world to us if you did.
We just launched the 2022 Acquired Survey, and we have had the wonderful problem of our audience growing a lot since the last time we did one of these. And we no longer feel like we have a great handle on who all of you are.
And so we would be eternally grateful if you would spare the three minutes to participate.

Tell us a little bit about yourself.

One lucky winner will get second generation AirPods Pro, which I have been wearing all over the place and are indeed twice as noise canceling, whatever that means, Apple.

And has some, I think, better battery life, too.

And David, for you, they have very tiny little ear tips, right? Yes, for my tiny, tiny ears. I'm so excited about the extra small tips.
They finally fit in my ears. It's awesome.
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And,

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we'll see you next time.

We'll see you next time.