ACQ Sessions: Jason Calacanis | Acquired

So wait, it was a magazine.

Magazine, yeah. I think that's how I started.

You said one. Magazines was like the original platform for.

Wait, have we started?

Silicon Valley. I guess we started.

This is the trick we've just been reporting the whole time.

Yeah, the whole time.

Welcome to acquired sessions.

All that stuff that you said beforehand that's like, is really juicy.

I don't think we should put that in.

No, definitely not.

Definitely not. And we don't want to tell people where the bodies are buried.

Well cheers, boys. Here we go.

This is 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.

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 your baby. What is acquired sessions?

Acquired sessions is normally on the show we are like so scripted.

Yeah, you are. And we have a great time.

We do four hour episodes.

You know, it's awesome.

But really for folks like you who we know really well, what happens if we throw out the script?

And just chop it out.

And we just chop it up.

David Rosenthal unplugged.

Wow. 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 got to thank Vanta.

Oh. Yes. Oh, Vanta.

I'm an investor. We're investors, too.

Well, great. They're an awesome company.

Big supporter of podcasts.

So, yeah, go Vanta.

We are huge fans of Vanta and their approach to the whole compliance process, SOC 2, HIPAA, GDPR, and more.

And we've got CEO and co -founder Christina Casioboe back with us today.

Vanta was already the best place to check the box and get security compliance certified, but now you've just launched Vanta Trust Reports, which take things even further.

Tell us about that and how they can help companies deepen their relationships and trust with their customers and partners over time.

Really excited about this.

It's actually a bit of not yet told Vanta history, but something like Vanta Trust Reports.

Honestly, a much worse, much more poorly designed version, but yours truly.

I'm sorry. I can say that.

We're 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.

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. Honestly, I'm joking, but I'm not.

Literally, the company's strategy on that day sort of became, OK, use the existing standards to bolster yourself and build something better here.

And so this launch of Trust Reports is really exciting.

These are companies that maybe it's before they've gotten a compliance certification, maybe in their process of getting one.

For some, actually, it's they already have one.

But then rather than keep going through their buyer's process, they're like, look, this is just constantly up to date and has all the information you need to take a look at this instead, rather than my 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 3000 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 percent discount.

Thank you, Vanta. So in the juicy stuff earlier, you mentioned Mahalo.

Yeah. I don't know.

Is that why you started the podcast?

Can we just keep referring to the juicy stuff?

Yeah. The juicy stuff.

We don't want to talk about that stuff.

That's stuff for you.

Yeah, yeah, yeah. Is Mahalo why you started, you went from print to print?

Well, in the 90s, you know, I grew up in Brooklyn.

My dad had his bar seized by the feds because he didn't pay his taxes during the 1987 crash.

He became like he got behind and the 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. And I might be going to jail.

So take care of your mom.

So he was like really behind on his taxes.

And, you know, state liquor authority, they kind of take it serious.

So feds come, shotguns, the whole thing.

They seize the place.

They seize everything in it.

And I was like, well, I guess I'm going to school at night and I'm going to work during the day.

And I worked fixing laser printers.

And that was like a really good rack of the HP had just come out.

And what you said to go to college somewhere else.

Well, that's another story.

But I was set to go to Brooklyn College.

I got into that. I had also taken the police exam to be a police officer.

So my brother went into the force and then I said, you know what, I'm going to see if I can go to college and make that work.

So I'm going to Brooklyn College.

So I decided to work during the day and then I went to school four nights a week, 6 to 9 p .m., carried full credit, 16 credits a semester.

And I would work fixing laser printers all day.

I was a bad student.

I was always that student to 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 BOD modem, which then became a 1200 BOD modem in my PC Jr.

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 in Pong.

And so my dad bought this for us when I was six or seven years old, 1976, 1977.

And he had one of the first pongs in Brooklyn in his bar.

He must have cleaned up on that.

Oh, my God, it was crazy.

And so we I just got exposure to video games and computers and I was like, wow, this is incredible.

Like computers are going to change everything.

And then I happened to hack some software.

We used to. I ran a lot of scams, but you told us about the VHS.

So VHS Jason's hot tapes was technically my first business, but there was a side job I had, which was cracking software.

So we were we would make copies of like chess master and stuff like that and then sell them for 10 bucks.

And then we started like hacking and doing what was called phone freakings.

When you were doing this stuff like it's you to be reasonably technical to do it.

Not like the, you know, not like Wozniak technical, but like you could solder chips sometimes we change.

Yeah, like we put we put memory in at that time.

You had to like take the memory chips and put them in and then bend them over and stick them in.

Did you ever think about like, did you consciously ever make a fork?

Where you were like not tech media and of course media about tech, but you're like, I'm not going to be the guy doing the boards.

I'm going to be the guy writing about the people doing the boards.

It's a very good question.

I used to go to Bleaker Street.

I used to hang out in the West Village or the East Village.

It was like the cool places to hang out and like a thing to do would be to go to Tower Records and look at the zine section.

So there was a concept of a zine, which was short for magazine, but a zine was something you wrote with your friends.

You printed it yourself at a photocopy store.

It's like blogs before blogs, blogs before blogs.

And I created a zine.

I was like, I'm going to be a magazine publisher.

So the first one I did was cyber surfer, which was about dial up magazine dial up services and CD -ROMs.

And I did it with my friend Brian Alvi, whom you might have heard of in my career.

We went to high school together with blogs.

We did web books together.

Yeah. So but in the early 90s, I did which is Engadget, twad.

All that stuff. Yeah.

Everything you sold AOL.

I think I sold AOL.

But anyway, before that, I did this magazine.

I did that magazine.

And then I had met Jerry Colonna at Internet World, the first one.

And he there was a booth.

That's right. When Jerry was a VC before he was like the whisperer of startup coaches.

And I think CMGIs. 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 and Union Square.

And he said, listen, I'm leaving Lycos, but I'm going to start this.

Hack me ventures with my friend Fred.

I want you to come read business plans for us.

And so I met Fred Wilson and I would go up to them and they were doing J .P.

Morgan was going to back them for their venture firms.

1994 -95. This became Flatiron.

It became Flatiron.

J .P. Morgan was the first big anchor of Flatiron.

They were half of it.

And Masayoshi San Softbank was the other half.

No way. So they wanted you to come like be a VC associate.

Not a VC, just to read business plans.

So the deal was they would take me for sushi and pay me a thousand bucks.

Wait, what do VC associates do besides just read business plans?

Well, it was a thing.

And so I had the magazine started Silicon Eye Reporter and they were paying me.

And so I read about this.

Beverly Hills Internet Company, which got rebranded as GeoCities.

And I wrote a little coverage of it and I said, you should invest.

I'm 24 years old. I don't even know what VC is.

That's where Flatiron made all their money.

Yeah, they were going to invest anyway.

The Flatiron became U .S .V, right?

Square ventures. Flatiron went with Jerry Colonna.

But then when Jerry decided he wanted to move to Colorado and just chill, he had made enough money, I think, and coach founders.

Coach founders, I think.

And yeah, maybe he had like I think he's been pretty public about it, like I don't want to say a nervous breakdown, but a kind of like maybe a fork in the road, like making a decision about what you want in your life kind of situation.

You wrote that great book about him.

Yeah, yeah, yeah. And so Jerry was a good mentor.

But Fred actually became ultimately my deep mentor at that time.

And Fred said to me, listen, you're doing Silicon Eye Reporter.

You're writing about us.

And the companies we're investing in.

And you're doing stuff, which do would you rather do?

And I think I'll do the magazine.

This was before. Now it's like I do both.

And now it's like I do both.

Why choose? But just to back up to DIO cities, that sold to Yahoo for like $5 billion.

And I think Flatiron was the main investor.

Yeah, Flatiron maybe over 5 % or 10 % of it at the moment.

It was a huge win for them.

I mean, Fred was on fire for a New York VC and Jerry.

They did pretty well.

They had done. How did that happen?

Like, I mean, Silicon Valley was here, but they were in New York.

What was going on? Yeah, we just there was a lot of good companies brewing in New York.

And my concept with Silicon Eye Reporter was where they have red herring.

In the Bay area. Upside in the Bay.

But I own New York and I had Silicon Eye 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 in revenue off my credit cards.

And had 75 to 100 people working for me when I was 27 years old.

And I didn't know anything about how to run a magazine, how to run it.

So I taught myself everything.

What'd your family think of this?

Like? It was pretty heady stuff because I wound up being on the cover of The New York Times on Charlie Rose and they wrote a feature story about me for 8 ,000 words in The New Yorker.

So anyway, it's a really cool time in New York because at that time you were either in media or finance or art publishing.

It was like a finite set.

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

And so everybody wanted in on that.

It would be like the equivalent of crypto is today 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 a lot about a lot of this when we did our big empire of Jason Kallikana's episode with you.

So I want to like put this on pause so people can go listen to that.

You should, it's great.

We get like the detailed story of like web blogs, Inc.

and all that great stuff.

And you mentioned, I want to like take us from your, as good as the, you know, your greatest, your newest thing.

Cause the last time we talked to you, you were just starting all in and like, can we talk podcasting?

Of course. I love it.

Podcasting is like, I think perhaps my greatest medium.

What happened with all in, how did I mean, it's weird.

Has it surpassed your wildest expectations?

Um, I thought it would be something Chamath and I would do 10 times.

Yeah. So the origin story is pretty simple.

Um, Chamath, uh, I knew because he was running ICQ.

Chamath was running ICQ.

At AOL. And I had sold my company AOL and like the revolving door.

There was like Ted Leonsis had this March to a billion, uh, my Greek brother and mentor had this like March to a mill, a billion, uh, offsite.

And so I went to this and I just sold.

Web logs, a million AOL users, hot shit.

That's the, that was the idea.

It was that, well, with web logs, Inc.

And with, uh, AOL and other assets they wanted to buy, they were going to March to a billion users.

It was like this crazy rallying card.

And we had these t -shirts March to a billion.

So I go to that and I see Chamath and I was like, Hey, and he's like, Hey, and we introduce each other and we had no one of each other.

And so 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.

That's hilarious. And he's like, yeah, but I'm gonna think I'm going to go, um, I got to go to the West coast.

I'm going to go work at this VC or whatever.

So 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?

Cause he was at Facebook.

Mayfield. Mayfield for a year.

And then Sean Parker introduced him to, uh, zuck and zuck needed, you know, like a Chamath, he needed like somebody who would just, Chamath 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.

Um, and he was like, you guys must've been like brothers from another.

Yeah, for sure. For sure.

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

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

That is, uh, we listened to it.

It was, it's fun to go back to that moment.

And you know, he, you can see how he's not, you know, polished.

He's not Chamath, you know, it's Gregarious or whatever.

It's a little more reserved.

He doesn't have Valero on.

No, Laura Piana. He was, he was, was he a great shaper?

No. He was like, he was like a dork, you know, like he, but he was, his bezos pre.

Uh, yeah, it was like, yeah, whatever.

You know, he, he always was a poker player.

He was playing in 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.

But, um, and so I kind of introduced Chamath 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, it's really good on stage.

Like he's funny or whatever.

And so, which at this point you had an eye for cause you were like, of course.

I mean, one of the things when I was a podcaster in those early days, you know, for about 12 years ago, whatever is, you know, I introduced a lot of things to the world, 14 years, 14 years, introduce people to the world.

Uh, yeah, it was 2008, I guess whatever.

So I introduced a lot of people who were in tech to the, you know, and it was only a couple of 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 podcast.

As we know. No, of course not.

No, I mean, there I have my own theories about what makes for a great guest.

We'll put that on the slide for now.

But, um, anyway, we started a friendship.

We started playing cards together.

Uh, we start hanging out, you know, trading notes kind of thing, and he's going to start his venture firm.

I'm a scout at Sequoia, all that stuff.

We started 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.

Cause he had done a bunch of interviews with me on stage and stuff like that.

And my events. He's like, I want to do a podcast with you.

I was like, yeah, you can come on this week and start up at any time.

It's twice a week now.

And, uh, which it's now five times a week, six, six mics.

I'm going to go, I may go back down to five next year.

It's a little much right now.

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 may.

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

Um, anyway, Chumaf 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, someone just put with it.

I said, okay. And he said, I want to do a new pod with it.

Just me and you. We talk.

I was like, sure. He's like, what should we call it?

We're texting back and forth.

I was like, we should call it all in 2020.

Yeah. It's like two years ago.

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 like all in because you ever, you'd been referring to this poker game on air on twice.

I would talk about it once in a while, the poker game that doesn't exist.

And yeah, Sky Dayton and I had a poker game with Brooke Hammerling, the famous PR person at the code conference, which was the all things D conference before that for 20 years.

Then Chumaf had had a poker game sacks.

I had hosted it floating and putting all that together.

Um. Yeah. I'd have referred to it many times on the pod, but try to, you know, keep it from becoming public.

But it was B Bill Gurley.

It's all public now.

Mark Pinkness, right.

Or maybe I think is that 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, well, where'd you go and just drop in these little red curtains here?

We got to pick them up on the same point.

We got to pick these up.

Anyway, at some point I'll write a biography.

Anyway, um, 10, nine years.

Uh, third book. Anyway, the, um, then we, we were, the pandemic starts to happen.

Like, well, sacks has some ideas about masks and then Friedberg.

Saks and Friedberg weren't, there was no besties originally.

It was just you and Chumaf.

I mean, in truth, like, uh, Friedberg and I weren't besties before all in.

I mean, we knew each other, we were friends, but not besties.

I was besties with Saks and Chumaf and now Friedberg is the bestie.

Um, and, but he played in the game obviously.

And we had just started to have a developer friendship.

But anyway, that for some 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 Chumaf, so I was very comfortable with that.

I mean, at the poker game, we break chops and I make jokes.

Um, and Chumaf's a great host and just very comfortable with each other.

Uh, and, and Friedberg kind of joined that group and, um, it clicked.

And I think during the pandemic, and I thought maybe this last 10, 20 episodes, but during the pandemic, I think people wanted information and I realized that perspective, 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.

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.

It's in some ways, the world wants us to be enemies.

And I kind of think about it like, um, you know, best of the enemies kind of situation.

Like we debate specific things like, uh, Gore Vidal and, um, who was this advert, yeah, anyway, it's a great documentary about Gore Vidal and, um, who's called 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 sixties.

They started debating like a different conventional political conventions.

That was like the most compelling thing on TV.

And they were like friends, best of enemies.

Uh, they weren't besties like Saxon I are, but you know, Gore Vidal was just, he was gay.

Um, kind of closeted or quietly gay and on the left.

And Buckley was like a serious conservative and they went to blow sometimes on the show.

Like at one point Buckley, I think he called him like a sissy or something like really like derogatory as a gay man.

And the world didn't understand he was exactly gay.

It was like sort of time period in the sixties where it like, maybe some adults understood like, you know, that's a gay man, but we don't say that.

When they got into town yesterday, we were driving the Castros right here by and we saw a naked guy in the castro and I was like, Oh, naked guy in the cat and Ben was like, dude, you gotta understand in the castro.

It's like huge jacked dude walking around and super sunny.

So he's like, just all like slick down.

So did he have his shoes on?

Was he wearing combat boots?

Some of the usual boots.

Yeah. And then they usually carry us around.

There was a big debate when I first moved up here because there was a number of folks who used to like to get a Starbucks and they had to like negotiate.

And they were like, how about a sarong in Starbucks?

Cause you're going to sit.

Right. Bareass and for context, for, you know, I've explained this to Ben, but like, this is a thing in the Castro and San Francisco, it's a cult.

It's like, uh, now it's like, you see, and it's like, ah, this is like a relic of the sixties, seventies.

It actually was pretty awesome.

Cause David, we're like driving up and David goes, Oh, a naked guy.

It was the most like warm hardy.

I had to, um, yeah.

I just, as well as a New Yorker, because as a New Yorker, if somebody's naked.

That's a sign that there's about to be some crazy person in a fight and police and chaos.

And here it means like high fives and right ons, but you know, growing up in New York, like if somebody takes their clothes off on a public transportation or in a cafe, like people are getting a baseball bat and a calling the police and like the shit's about to go down, 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, what, why do you think it works?

Like, is it, do you think it works?

Like the number one ish tech?

Well in our business is number one of course, but it's number, it was number 28 last week, like in the world on IG.

You guys have transcended like this is more than just a tech anymore.

It has nothing to do with finance or tech anymore.

It is tipped over into colleges.

I was at, I was as, you know, skiing and 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 and no pressure, but are you going to be leaving soon?

Cause I'd love to camp out here and get your day.

Like stop busting my balls.

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

And I was like, 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 said, I listened to it twice.

And I was like, oh my God, that's so nice.

Just like, I was like, are you in the industry?

She's like, I'm a dentist.

Reno. And I'm like, you're a dentist and Reno's can I ask how you found out about?

She's like, I don't know.

She's like, I deeply care about San Francisco politics.

No, I found it. And this is, you know, during the pandemic situation.

And that's when I realized it across the world.

Was there a moment for you, either you four or you where you were like, whoa, this is, you know, I've been, um, micro famous, you know, micro celebrity multiple times in my career, but this is not for me, you know, and I got a lot of famous friends.

Uh, you know, I, I'm used to getting recognized.

I'm used to people taking pictures.

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

If I was walking around in New York, now it's 20, you know, or 10 and they want to take a selfie and it's, you know, just, you know, podcasting is you guys get recognized and it creates a level of intimacy with people if they're in the habit, because you're hearing people every week and then people

become characters. And I tried to make everybody I was, you know, in, in all on show or, in all honesty, I did craft with all in, I was very premeditated and creating some character I've never really talked about 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 and, you know, Freiburg didn't even have a Twitter handle, zero followers.

There's even a character of JCal on All In.

JCal the world's greatest moderator.

Sure. Yeah. I think more like JCal the guy who lets himself be the punching bag because it plays for the show.

A little bit. I would rather not, if I'm being honest, I'd rather not be the punching bag.

Like they're like, you're the poorest guy on the show.

I'm like, do we need to point that out so often?

You're like, not that much.

Like I'm feeling really good about myself.

You don't have to point out that you all have more money than me and you, two of you have planes and I don't, and it's 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 and, you know, whatever reason.

But you do, you do let yourself play that role of like, like you have been enormously successful and you sort of let the role of JCal 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, 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.

And 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.

I'm the poorest guy on the show, but like, I've done okay.

Maybe let's flip it like for them before all in maybe Tamat had a little bit of a public business.

They were not famous.

They had no go to market.

What do you, 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, carry out that it's speculation.

What do you think for them all in has like Dutton, 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 or in circles.

What's that or Monsanto, or Monsanto.

Like he's very connected in those circles, but he was kind of under the radar guy.

I think really by design, he didn't have any desire to.

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

The, 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 and a session at all in summit, uh, you know, just say who your favorite bestie is.

And then direct question.

And it was like five in a row Sultan of science.

And it was like, Oh my God, what have I done?

Now I've created this monster.

You know, 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 Kursner and if you can't make her, 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, Freebird will show off, but he's actually really committed to the show now.

Um, for sacks, 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 more so than any, you know, was 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 mafia.

You would say Elon, Reed Hoffman, Peter TL.

Max Levchin, Jeremy Stoppelman, Chad Hurley.

Rule off. And I guess sacks would be somewhere in that strata.

Like being known, being known, being known.

Being known. But yeah, you know, and I think part of the reason this works is sacks, I think sacks have probably taken the brunt of the head of the pod 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 flows.

On the margins probably.

I think there's probably, I don't really marginal.

I wonder, I wonder.

He said that jokingly on the show.

I don't know. I'm just thinking like maybe there's somebody else has ascended because he's done all in a way that, 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 Chills venture firm because I'm so liberal for sure there are.

And okay. So those people feel that way about craft now, but for every one of those, there's 10 more, 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.

Um, I think the pod to 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 that we maybe made it okay to admit you're a moderate.

Yeah. You know, I I've been telling folks from the beginning, I'm an independent and a moderate, I voted probably democratic three out of five times, four 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've voted for Bloomberg, Giuliani when Bre was crazy and Pataki who were all Republicans to me, or we still know I wasn't, but I would have 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.

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

Yes, it is a small group.

I, I, um, I think I believe in competence and staying out of people's lives.

So I, you know, it's very hard to know.

Cause 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.

Um, and certainly I, the MAGA group has no love loss for Jake.

I'll tell you that like really crazy.

I would get like brigade in the last couple of months.

Nuts. Um, it's funny, but it's also like on the margins, like they can get a little scary.

Like they'll docs me sometimes.

And I, you know, that's not fun.

Um, a handful of times it's happened.

Uh, but you know, I had to tell David, like David, I, I am not like, I don't actually listen to MSNBC and Rachel Maddow to get my information.

Uh, and by the way, your pro choice pro gay marriage, anti -war.

Yeah. He's the dove and I was like, well, okay, if you don't play this game, I'm gonna play this w David, the dove, but now you're making me into Jason, the hawk.

Like, what are we talking about here?

Like, um, but anyway, you know, just goes to show how silly the coalition building is like, it's totally 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. And so like, I would hate him as a Democrat or a Republican, so it's not personal and I would, I would love to.

Or it is personal with him, but it's very personal with the party.

I mean, I just think this is like just horrible human being on, uh, you know, in every way.

And 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 friends and neighbors were, 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 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 iPhone 14 pro and it's magic and whatever, but like, it's not that different than my old phone, but I got to participate in all the fun watching of the keynote and the tweeting and the nerding out on like, let me look at the image quality versus the old one because it really is pretty.

It is pretty, but like, I got to be part of a tribe.

And like, that is a thing that no matter what your tribe is, that is so fun to be there on tribe day and tribe.

I will say the thing I'm proud about the show, I think is that it has, you know, through a lot of the trials and tribulations shown that you can be friends, disagree, learn from each other and have a vibrant debate, which is how we all grew up, I think, when I say we, including you guys, but also specifically

the besties, I want to be friends with people who I disagree with.

I want to debate stuff.

And then people are like this guy, Dean Preston.

And he's like one of these supervisors here is super idiot, like guy in San Francisco, like, um, you know, like, won't let them build housing or stuff.

And he's like, you're just a conservative blah, blah, blah.

And I was like, you don't actually understand who I am.

He's like, you're a conservative billionaire.

I'm like, wrong on both accounts, but thank you for the latter.

My besties remind me on that.

Not trying to be a billionaire.

Thank you. And, uh, on, on that, another thing that's really fascinating to me about all in, and you guys is before all in, and maybe it's still to a large extent, I feel like Silicon Valley has this weird relationship with money, like super weird relationship with money, like, you know, remember there's

a whole thing about like Zuck drove like an Acura SUV.

And like David Philo and, um, David Philo and Jerry Yang were driving their old cars to work like the cool thing.

Like you, you could like make money, build a company, but like, you never want it, like you never, and be understated.

You guys, I think are the first like, like, you guys like whatever.

Like, we got a private jet.

Like that's fine. Like, you know, I mean, listen, 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 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 of 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 a small like outlier wealth creation.

And we don't think enough about inspiring people to create companies and learn.

And like, the time I create the most controversy is when I'm like, I believe anybody can do it and people were 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 in Stanford and Brown is online for free.

And I listen to macro economic 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 open courseware.

And I'm like, I can't believe I can take a course at MIT for free any time I want.

And then you flip it.

You can build a business there.

Like David Sennro over the founders podcast, like Mr.

Beast, MKBHD, like nobody gave you guys permission.

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

And like, I watched the world become so fair and so just and so much information and opportunity to 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 I vary. I think the key insight is like recognize that the world is unfair.

And actually what that is, is a game on the field and figure out how to play the game on the field.

But I mean, it's never been more fair.

So the world is unfair.

True statement. And in America, it's never been more fair.

You can learn. Google has like five courses online.

I think it's called Grow with Google or something where they're teaching how to be a UX designer, how to do this, how to do that.

And it's free so that they can get more people to apply for jobs and the average job entry salary for these things is like 80 K.

So I I find that 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 their community.

That's how they find that there are other people who love that.

They tweet that the world is unfair.

And they have to and it typically like is a certain type of person.

I'll just leave it at that.

OK, can I so I'm going to leave it at that.

And when I teach Founder University now, I have a course where I teach people for 12 weeks or I should say I have a team that teaches it and I'm going to actually teach it myself.

This next cohort where I just teach people how to start companies.

All right. Let's plug it.

How can they find out where they're at university?

That's it. There you go.

Yeah, I mean, it's basically it's free.

You the way I did it was you apply.

If you want to build a company, you pay seven hundred bucks.

If you go and you get to we twelve, we charge your strike back the card back to seven hundred bucks if you don't come or if you don't have an excuse absence.

If people miss something because of their kids, we're going to be fine.

But we just try to get people to complete it over 90 percent.

People completed. That's cool.

So and then we're investing twenty five k and some of those folks to help them start their companies because people don't know all the work I'm doing like quietly, but like two hundred people go to this course now.

Maybe about four hundred in the next coat of the fourth cohort.

We'll see. But you know, like people can learn how to create companies.

And they're like, no, they can't.

And I'm like, yes, they can.

You have to have gone to Stanford.

I'm like, no, I'm invested in three hundred fifty companies.

Like maybe five percent 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 more open.

Nobody cares where you went to school.

No one cares where you live anymore.

Nobody cares where you live.

They care about what you've built in 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 then you say the N word.

It freaks people the fuck out.

I'm like, why is it so scary for you that Silicon Valley is a meritocracy?

And they're like, because it's not.

And I'm like, it kind of is.

Can I, can I answer your question earlier of what, why I think all in works?

Yes. All right. Go ahead.

So I think you're the, you've got the perfect storm of three things.

The first thing is billionaire born most people you're counter positioned.

Most people who attain that level of wealth crawl into a quiet hole and make sure no one knows you're doing shows from boats and jets.

Yeah. So there's like, I don't think we've done it from a jet, but yeah, there was definitely two boats in the last two years.

They're like, 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 COVID -19 on all in that I wasn't getting through any other source.

I'm like, somehow this is not making it to me.

And this feels very, like a lot of it proved out to be like, this was good information before it was mass.

Well, four of us are information junkies with a lot of research and teams.

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, they'll know I'm pretty sure files open on people's computers when they're talking.

We have a docket with the notes, but that's mainly for me to cue it up.

Like I just read the four or five bullet points.

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

And I think Saks has some research help.

I'm sure Friedberg and Shamoff read the stories or they're well read.

I know 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 in the world.

And you guys are young still, but, you know, imagine you do that for 20 years.

Like you're going to get smart or you're journalist for 20 years.

You can get pretty, I wouldn't necessarily say smart, but you'll be informed.

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

So okay. That's number two.

So yeah, we probably have a slight information edge.

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.

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.

When you weren't on the inside, but you weren't on the inside.

So when you're in the inside, you have a hundred percent 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, your try.

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, and it makes it successful.

It's the thing that David and I took forever to realize works about acquired, which is relationship and charisma.

Yeah. 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 into four hours of diving into stuff.

You would never read in a book and you guys do that in spades.

Like, and it's just so fun to like temporarily join your world.

And then the fact that you as a podcaster who makes elite content, like top 1 % content, find it compelling is just, yeah, that's right.

Listen every week. I mean, don't miss it.

I can't really walk in the baby up and down the hills listening to it.

I mean, I had people tell me, they listen to it twice.

They take notes. I'm like, wow, that's great.

You know, I, I don't take notes.

Maybe I shouldn't take notes.

Well, anyway, I was very intentional with my role in it to step back, and be like the point guard.

Um, but you know, I'm a shooting guard too.

So sometimes I will want to shoot the ball and I can do both.

I'm a combo guard. How did the, um, free break 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 on that person.

Go ahead. And I just like, sure.

I'll just shoot. Like, I, you know, you pass the rock and I'll like, yeah, you want to be a part of the show us.

And he did a, he did a solid job, but let's be honest.

Like, it's not a point guard.

It's not showtime. That's for sure.

Um, like I don't think people are going to go to watch him play point guard.

I mean, he did a serviceable job.

Um, 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, Saks wants to talk about current of his 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 in fans know this, I'm not speaking out of school here, you see it every episode.

Saks would disengage during science and quinoa we 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.

What's that's a hard job.

That's a, 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.

Uh, do they help? And I actually looked at the interjections.

And if you look at McLaughlin, you guys did not grow up on McLaughlin.

It was super unfamiliar.

So the McLaughlin group was the best Sunday morning show.

And like, it was so good.

Like SNL with parody, McLaughlin.

It probably had a million people watching it, but this guy McLaughlin was like pretty cantankerous.

And if he didn't like what people would say, he'd be like, wrong.

This is the answer.

You know, like, and it became so competitive that you want to watch it.

Now what I didn't realize by adopting that would be that Sacks is the ultimate debater and will fight like a dog until he wins any debate.

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

I'm trying to have it be a conversation.

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

And then the odd, some people in the audience are like, you have to be the fact -checker for Sacks.

And I'm like, no, that's not my role.

I'm not real time fact -checking Sacks.

And, um, 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, right?

So I'm like, explain that.

Right. And I'll stop somebody now.

I mean, you're, you're expanding the Tim to dentists.

Like that's correct.

Thank you. So people are like, Oh, J.

Kyle's an idiot. He doesn't know that term or I say to somebody, can you unpack that?

Can you explain that?

Obviously you know that term.

I saw the third or fourth investor in Uber.

Yeah, like exactly.

Well played. I think he's been in Robin Hood too.

Like, wow. Who knows?

And I'm like, uh, dude, like I'm asking that question on behalf of the audience.

So when I'm moderating, as opposed to being an interviewer or as opposed when I'm working with Molly and we're chopping up the news when I'm the shooter there, right?

And she's maybe playing point guard a little bit and I'm shooting and then sometimes I'll pass it to her and she shoots.

Like I can travel between those roles and you know, in that role, I'm acting on behalf of the audience and I get the sense like he's going, Chamath's going too fast.

They don't know what the spread trade is.

Let me pause. Can you explain one more time or let me reflect back to you?

Is this what a spread trade is?

And he's like, almost this.

And that's what I think has brought in to your point.

A lot of the dentists.

And having an intimate sense of where your audience's edges are is, is like really important role there.

Like it's an off guests on, I'm always trying to catch.

Yes. Where, where did they just go slightly too deep and I need to pull them up so that we, yeah.

And, and, and, you know, podcasting is about going deep.

So it is really an art.

Like, do you want to stop somebody when they're going down this like crazy rabbit hole in this room?

And that, 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 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 have to say like, it's, it's been a different muscle for me to flex and it's been great fun for me.

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

There's a candy and there's vegetables.

And like, I listened to the audio version of Stratecory and that's my vegetables and it's not like deeply it's enjoyable intellectually, but it's not like fun.

And, um, I can't, I certainly can't be doing anything else with the language center in my brain while I'm listening to that.

I have to be like on a run and like sometimes even at home, so I can take some notes or look something up.

I can be cleaning. Yeah.

Plause it 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, cause I was like brushing my teeth and then I left the room and I came back and I'm like, Oh, I didn't actually miss anything.

Cause this has just been like, it's comforting.

Yeah. It's like, I love all the stuff he's talking about, but like, it's not.

Must listen every time, every minute, every second concept.

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

All in has become candy and vegetables.

It's both. It's both.

Yeah, for sure. I try to do with this, we can start up Zen all in is try to have it be both a little bit of personality, a little bit of entertainment, some fun hot takes.

I mean, what do you related, but separate topic?

Um, Silicon Valley.

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

And like, there's a lot of crap wrong here, but you guys are all still here.

How are you guys feeling about that?

How do you, how do you feel about that?

Like what, what do you think of the Bay Area?

Um, you know, I lived in New York, Brooklyn, then Manhattan, and then I lived in LA.

And then I lived here.

And so I think my, I'm moving to places.

I enjoy less and less each time.

I enjoyed Brooklyn and Manhattan much more than LA.

I enjoyed LA much more than San Francisco.

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

So why are you still here then?

Uh, well I can't, I can't, 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 can start a venture fund.

You kind of need to be up there.

I wonder how I would do if I was up there in the industry.

And I was kind of this, because if you wouldn't, you'd always wonder.

Well, Michael Marchetti used to call me the mouth from the south, because they had like two investments in LA is, Oh, the mouth in the south is super, what does the man, Sir Michael saying that, uh, but I moved up here and I love it up here.

It's quite bucolic.

My kids are loving it.

Um, it's, it's quite nice.

I would love to live in another city in my life, uh, or two.

Uh, I could see myself in Austin or Miami.

I like both of those cities.

I think Austin's kind of the future.

I think California is going to be, uh, damaged for a decade or two.

So I think for the rest of our adult lives, this town or I think the politics and not appreciating the politics, the regulation and not appreciating the tech industry is really the problem.

Um, and then you look at this guy.

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Yup. So if you want cutting edge cybersecurity solutions backed by a 24 seven team of experts who monitor, investigate, and respond to threats with unmatched precision, head on over to huntress .com slash acquired, or click the link in the show notes are huge.

Thanks to Huntress.

And Preston, like he is dunking on, um, the founder of away and Stuart Butterfield from SAC.

There are a couple and he's like, we got a million two out of them when they sold their homes and I'm like, and you also lost two incredible founders who've created billions of tens of billions of dollars of wealth for San Francisco.

You idiot. And like at the same time, Francis Suarez in Miami is listing all of the venture capital and doing a tweet storm about all the companies that 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 two.

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 the California marginal tax rate is 13 .3%.

I mean, but just so they have an exit tax now for homes in San Francisco.

So if your home costs over 10 million, when you sell it, I mean, I think it's just one point 2 million from them selling their home versus 13 % of their future earnings stream.

Which is like the chef at slack made a billion to paid a billion two in taxes from their RSUs.

Like are you such a where do you think that's a million two?

Probably. Yeah, the bill, the million two.

Yeah, but that order probably paid in taxes on their RSUs at slack.

You absolute moron like you're literally so upset about their mansion and dunking and you're dunking on an individual's name.

But anyway, the fact that we hate entrepreneurs who create jobs and wealth or certain people do is just insane.

It's just insane. Like what I mean, you could go change the tax code.

It's fine. Like, you know, raise the minimum wage.

Like Bernie Sanders and Elizabeth Warren attacking Bezos endlessly.

And then Amazon starts paying 22 an hour, gives you benefits and pays for your college and it's like, okay, hold on a second.

I know what basis just did.

He took the platform that you could never actually enact and he enacted it inside of Amazon.

If it's not perfectly clear what just happened, literally, he's dunking on you.

You wanted free college and couldn't get it done.

He gave it to Amazon employees.

You wanted a $15 minimum wage.

He made it 22 and you wanted everybody to have universal health care and he gave universal health care.

Like that is literally what Bezos did to them.

How embarrassing are you that like them pushing and push it?

No, no. Definitely.

It is literally him showing like as the Amazon crew showing like, let the free dish, 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 has is what has driven these salaries up right and the benefits

up. It's extraordinary what's happened with the free market.

It's still $7 federal middle wage is seven and change.

No, 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 like the data being integrated lets them do really great stuff to like you want your employees to be compliant.

So it ensures 100 % compliance, but also you need it to be easy for them.

So you can do cool stuff like have managers set budgets and then as long as people are spending within those budgets, then they're just in policy.

Everything's always approved all the time.

No receipt chasing.

So they're a seat chasing, no approvals, no, it's all just done.

All integrated. And they really are thinking about this the way enterprise companies who are expanding globally and deal with lots of contractors in lots of countries, with lots of currencies and just need like a command center that they're not going to outgrow that is really when you need Brex.

Like you're using globally, like how many companies these days, even startups employ people globally who are, you know, not just need to be paid but then are like spending, buying things, going to dinners, et cetera, around the world like you need something that operates globally.

So plus it's awesome though.

Like the remote work thing is here to stay.

They shared the stat with us.

Uh, 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 to obviously, uh, the last thing that we want to tell you about with Brex today is related to being remote and different time zones.

Brex now has 24 seven 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 seven 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, uh, 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, a new well of energy.

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

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 that.

Cause 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, and to me, or did he, no, just, you know, popped on zoom.

I, you know, he had to start it cause he did that tweet about his compensation tool where, you know, here's your total comps.

I was like, that's brilliant.

Come on the show. You want to come on the show and talk about it?

He's like, yeah, of course.

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 a day in and day out.

And I was like, I could be like those guys.

Uh, they every day get on there and they seem to love it and I do.

And so I just committed to doing it every day.

And I love it. Isn't it weird when there's something that takes a ton of work, but somehow doesn't drain you?

Not at all to me. It's like going to the gym.

It's like working out or having dinner.

It's just something I do every day.

That gives me great joy.

And then that's I've 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. I feel like that's the thing that's kept acquired going.

Is that like you and I can like, I don't know how you did it alone for a decade.

Uh, well, I, you know, I'd have guests on and was largely a guest driven show.

And then I would do the news round table once a week.

Cause it was once a week, then twice a week, then three times a week.

And then I was like, well, however many I just sell out, I'll do it five, six days a week, whatever.

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 exercised that?

Well, I created a platform founder university where if you want to build something, I will talk myself to 200 people you can build.

And then whatever rises as the performance and the product, you know, and they, as people move from talkers.

To the walkers to from, you know, when they actually start building stuff, that's when I get great joy.

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.

That's awesome. You know, I'm raising the fourth fund in public, like 11 ,000 angels in the syndicate.

Like this is going at a really significant velocity.

If you were to look at the slope, it's not quite a hockey stick, but it's hockey stick -esque in terms of the total capital I've deployed.

And it's in really high quality companies.

I'm getting better at it.

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.

And like, you have 12 people.

Um, those people are doing 60 introductory meetings per week, six zero.

And then we're doing maybe 15, 20 second meetings.

So there's, it'll be a hundred meetings a week, shortly, probably across 10 people.

Or 12 people. You're not doing the, I'm not doing them.

Uh, and what happens is you had this line wizard on, it was not even, it was on twist, not for me.

Oh, the people say that's a lot of work.

Yeah, but now for me.

That is the new philosophy.

This is why my energy is really high.

This is your, I have told everybody who comes to work for me, I work 60, 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 part of that team or is it like someone who likes doing that part?

Like that's, well, let me ask you 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.

And 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, uh, for a long time.

You come, you learn, you extract it too.

People come and they work for two, three, four years and they go start their own venture fund or whatever muscle tov.

It's great. Um, but what I told them was, you know, let's just find the great companies.

And I looked at investment team meetings.

Usually they're Monday.

People do it for an hour or two.

And then they go to lunch.

Uh, I said, I want to do it twice a week, Tuesday and Thursday, it's two to four PM, uh, hit me with companies.

So that was another innovation I did.

And I also brought Mike Savino, who was my first boss 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. Uh, you teach the course.

Are you enjoying the LP fundraising?

I am now. Yeah. I am.

I'm kind of like, uh, remember an X.

I don't know if you watch billions.

Oh yeah. Every episode.

Great. So, you know, like at some point, um, uh, he was like, I'm going to 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 and just fixes everything.

And I'm like, I'm going to go raise money.

And so literally was like, we're doing 506 C and they're like, wait, 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. Um, I've had select institutions make small bets.

The first one was 10.

The next one was 11.

And then the last one was 44 million.

The first one I deployed in five years, second fund, two years, the third fund to, you know, five years.

I was just, that was my first fund.

It was, you know, me, Bill Gurley, Dave Goldberg, rest in peace, Tony Shea, rest in peace, David Sachs, Chamoth, just a bunch of my friends put money in and it was to see if I wanted to be a venture capitalist and do this as a career.

And I was like, yeah, I just did it over five years.

And the second one I raised 11 took me six months to a year to raise the first.

It took me, the second one took three to six months.

The, 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.

I literally did two webinars, a couple of 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, inspiring VCs raise on publicly.

You didn't raise publicly.

No, you should have thought about it, but for a whole bunch of reasons.

Well, it's kind of scary because people don't do it.

But if you have no track record and you want to raise, so like this guy, Mac, the VC, yeah, you did a great episode with it.

Yeah, it was great.

I had him on and like, you know, first time founders for a season of angel.

Um, it's like a subsection of the, this week in service podcast.

And I became an LPN is funded.

And you just saw me like, I just did like hundreds of meetings.

I did like five meetings a day for a year.

And I raised my whatever, $10 million 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 angel issue, set it up.

And then you just start talking to other VCs.

You talk to them and you just, you just have to be willing to take 50 meetings a week.

And I'm like, dude, do not say that it's easy to raise a venture fund as a black man in Silicon Valley.

But that's what this shit is.

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

You find your people who believe that with you and then they believe in you and then they back you and that's the whole thing.

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, you're, when's your next fund?

I'm like three years.

They're like, oh, let me know.

And I'm like, okay.

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

Yeah. Three years from now what you 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 for.

Is there a limit to the number of LPs you're going to have?

Of course, 250 accredited, up to 10 million and then 2000 QPs.

And so it's a lot more work and QPs, not for me, to catch everyone.

Qualified purchasers.

Look at you playing Jason, I know you know what a QP is.

I just want to ditch the ball.

I think it's 5 million in investible assets.

Like, uh, and then, uh, accredited now is 200, if you're an individual for the last two year, 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.

That's not every 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 year.

So. Just like I democratized angel investing, was the book angel was the first syndicate on angel list, the most successful syndicate on angel list, created my own, got the domain name, the syndicate created the largest one, have done 265 syndicate deals by far, like the largest amount of anybody, I

think, I don't know.

I mean now as a participant of a fund on angel list, like I didn't, these are like, those are big numbers.

Like do something consistently for SPPs on Angel list and we have the fun too, but like, you know, yeah, like there's a lot, you're hurting cats.

You need to have a lot of people.

Um, but anyway, putting all that together, I think now's the time to democratize venture capital.

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

Um, it's high risk, it's high reward.

I'm in 20 venture funds myself, including yours.

Um, and I'm sure, but don't, but don't pitch Jason, do yours.

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

And, um, well, this is kind of to the conversation earlier, like on the internet, this is the democratizing thing.

Nobody's going to just give you, if you just, you know, nobody's going to just invest in your fund, but if you go do stuff and then people like, oh, Jason does stuff, great, I'm a back Jason then does stuff like be of action.

Yeah. And it doesn't mean you have to start our pockets.

You could be a blog, you can do a, whatever.

You could create founder university, whatever it is.

You can do any of those things.

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

Do you like the idea?

I'm, I'm curious as someone that's always raised, uh, from sort of individuals.

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

Oh yeah, of course.

I mean, I, I've had five, you know, million dollar checks, $10 million 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 were cancer survivors to have memorial Sloan Kettering's endowment or an endowment.

UCF or something like that.

Somebody like that, you know, if they wanted, I would work, you know, really hard to try to get them a great return.

I would find more, I would find even more meaning in what I do.

Uh, and I, you know, I got that from Sequoia like, you know, you, they would have this Sequoia dinner every year for the founders and they would say, here are what the foundations who are LPs 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 and your, Yeah, their, their conference rooms are named after their, and this is really powerful.

Like I find we have like state pension funds and stuff like that.

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

It's cause it's not just about the rewards.

I'm like, oh, I, I'm so excited about what we're going to do for them.

It's like, this is really important to preserve and grow, but like preserve this capital.

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

That was like one of the seasons of that of Billions was he's like, I'm going to be a family office.

No, I'm going to raise my own phone.

Right. And so there's this natural tension for acts like, what should it be?

And he decided, yeah, I like when I have other people's money because he, he seemed to perceive like, I think he felt that he wasn't a somebody in his ecosystem in his community without managing outside.

I think it's like playing, you know, in the bubble with nobody in the stands versus getting on the court at Madison square.

It's like, and there's people in the states, your numbers don't mean anything unless you're putting them up for dude.

I'm doing this public.

I should say quasi public people.

I still have to sign up to, you know, come to a webinar.

Um, but I'm sharing with them, like, here's my, the totality of my investments and here's what I've done.

And here's what I plan on doing with my team.

Um, so, you know, I'm kind of enjoying it.

Um, and if you, I've met with all the top endowments in the world over the years, and they're very kind to me, but it's always been like solo GPS, a blocker, no track record.

Your fund is so small.

We're at $50 billion endowment.

And you know, like, you know, um, at some point, like one of the ones who's the most rigorous, I wouldn't say exactly which one was like, we have a lot of respect for you.

We know who you are.

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

But I just want to be straight with you.

We don't add many funds.

And if you go through our process, it's going to take a lot of your time and it's going to result in you not getting our money this time.

I don't want to put you through that, but I respect you.

And if you want to do it, we'll do it.

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

And I was like, let's do that.

I don't need the money.

Let's wait. And I think what a lot of these funds are doing.

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 placing this bet.

Would anybody like to join me?

And I don't have to have a fund.

I don't have to do audits.

I don't have to do any work.

What is this? 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 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, uh, and this is why I like, when the guys break my chops on the pot, I'm like, guys.

I don't aspire to be a billionaire.

I, it's not important to me.

If it was, I would do a late stage fund.

I aspire to be happy and do what I love doing every day, which is the podcast, maybe get in 40 days of skiing, hang out with my kids, take them on the mountain, and then meet with like, you know, early founders and be able to say I helped that company at the earliest stages.

That to me is the rush.

I found them first.

I backed them first.

I sat there with them and figured out with them.

We were talking about the legendary twist episode 180 with you and Travis.

Like, I mean, that was the secret before the show stuff, David.

Yeah. That is this, but from the juicy before the show.

And yeah. Yeah. But that was like, you know, you know, her boo was such a baby company back then and like, you know, one city, one city invested.

And I had an open angel for him where.

Sayan Bannisher and Chris for Alec from first run, you know, invested in the company.

I think they both met them there.

Socko was there too, but he already had a relationship with Travis.

So I can't take any credit for that.

And Kevin Systrom was watching and I was going to kick him out because he was at this coworking space called dog patch.

I worked there too.

I worked as co -tweet.

Yeah. So he was, oh, co -tweet.

I know that. Yeah. So he's sitting over there building bourbon.

And Socko is like, can bourbon come in?

I'm like, fuck no. This is like private shit.

He's like, but, and I'm like, just tell him to sit at his desk and I won't give him an album.

Wait, this open angel form was at dog patch labs.

Here on the pier. No way.

Then they shut down because it was going to collapse.

Condemned. So that was there.

And, uh, No, so did a bunch of like events there for angel.

I, at the time, no, Val 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, 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 an in person and he's like, I'm going to 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 SPV?

So I was like, I don't explain it to me.

He taught me what SPVs were.

He introduced me to a shore 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 listed in it, but they back everybody and, uh, they've done more SPV is like, look, like, I don't know if they're up to 10 ,000, 5 ,000.

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

Seriously great group over there.

Um, and so he taught me how to do syndicates.

And the first one I did was calm at four or $5 million.

It's funny. I was, I was looking for you're literally like winning a championship.

The first time you step on the court, I was looking at your track record, getting ready for this.

And I was telling David, like, I think the word that I used, cause like, obviously Uber is some ridiculous multiple on a return.

Um, but then there's these other ones that are like promising but early.

And then there's other ones where it's been a less than Uber multiple, still good Uber multiple, but you look at calm.

You just, I looked at David and I was like, he sharpshooter that one.

I could be even more proud of because it was like ridiculously early and like a super low basis.

They had, it was $4 million.

We put 378 K and owned 6 % and they didn't raise any money until it was a $250 million valuation.

So no dimension. Um, and sharp shooter, sharp shooter.

And I couldn't even cry like telling the story, but, um, Alex too and I became very good friends at Michael act.

And you know, afterwards, um, cause he wasn't actively running calm while Alex was, um, Alex at some conference, I was interviewing him and doing a little victory lap for him and, um, giving him his flowers and he said, yeah, I just want to stop and tell you, uh, you don't actually know this story,

but we were going to shut the company down and we had Mike and I had a conversation.

What do we take your money?

But we're not sure about this, but you believed in us so much and you insisted on us taking the money, but we had just pitched 40 investors.

And they all said no.

And we were trying to debate if we could in good conscience, burn your money to do this and we probably calm would not be here for, and they found the product market fit while burning through your money.

I think so. I think so.

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

No, no. But I mean, you think about that as like a, that is not the case with Uber or Robinhood.

I was along for the ride.

Let's be honest. Uh, they, I did not change the trajectory of the company, but for Jason Calacanus, calm is not where 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.

Like there's, there's a lot of like individuals participating in venture rounds and like, no offense.

Oh, hey, so like all that angel investing, but like coming in when the company could die needs a hundred K 200 K 300 K to get it to the stage where they, I mean you to date, I think when I invested.

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 and had it for life.

So the business model of apps was make a lighter for a dollar, 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 and it's like, well, we can just update it.

And it's like, yeah, but we need to make more money.

So shut the old one down.

So you buy angry birds and you buy other birds too.

Angry birds three. And you know, it was a really weird time.

And then they were like, yeah, we're doing, they told me like, you know, um, cause you know, I was under NDA as well and you know, Hey, subscriptions are coming.

That's going to change everything.

And they were going to do $10 a year.

And I said to Alex and Michael, how much does it cost to go to a meditation class?

This is donation based and there's only like 10 places you can go.

I'm like, well, what if, what's the suggested donations at $20 in.

I said, you want to church $10 a year.

It's $20 a month. How often do you have to do this to get it out?

Yeah, I 20 hours of visit.

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

And so it should be a daily practice or like, well, how often do you have to go and learn?

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

I was like, so it's $80 a month to go and we're charging $10 a year.

So that's like a thousand dollars a year versus $10.

What if it was $10 a month?

They're like, we've been thinking about that.

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

Then they went to $10 a month or whatever.

And they didn't wind up at $60 a year, whatever it was, but we got money printing machine pretty quickly.

So I've never made an investment at like pre product market fit.

That's like now worth over, you know, a billion dollars.

Like that's a, that's a very early to very successful.

And I'm curious, like, did it feel any different when you were making that investment where you like, there's something more special here than my normal investment?

Absolutely. Really.

Absolutely. And that's what I've basically turned into a playbook at launch and that I'm teaching these 12 people how to do is how to do that.

What do you think it was?

Like what was when you look back and you're like nine factors?

Nine factors. All right.

Well, angel angel that university university.

I'm training my team when they're meeting with those 60 companies and every time they pitched 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 the 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 Robin hood, okay.

They're the best looking app with the best UX of all of everybody in the category.

So calm was better than headspace, Robin, who was better than E -Trade.

I mean, it's 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 was like, I'm like, like, I really like the design.

I'm like, pull it up.

And they pull it up and I'm like, that's a template from, you know, like a website builder and it's a stock photo, but where's the actual design of the product?

And they're like, oh, that's on this product page.

And my product page.

I was like, okay. Again, that's just like the, I mean, if this was a bank's website, maybe, but that's not world -class that's serviceable design.

That's utilitarian design.

That's okay design.

That's good design.

It's not world -class.

So let's, if we're going to say world -class.

Like a world -class performance is different than a serviceable performance.

World -class cinematography, world -class script, world -class dialogue.

That's different. And that's, and then product philosophy is the other one I like.

So, okay, we met with this company in June.

It's now July. What's changed about the product?

And they're like, we don't know.

I'm like, okay, well, let's find out.

Where's their change log?

Where's their roadmap?

So in the earliest stages, you might have revenue traction or user traction, but you might be able to ask them for their product roadmap and somebody like Travis would be like, yeah, here, I'll get on the phone with this guy and we'll walk you through it.

Here's what we're debating about on Sunday.

We're reprioritizing.

And then a month later they play check, check, check, check, check.

And then you go like, if we're with Raul with Superhuman and I was investing in this company before that report of Raul like the change log at Superhuman.

Dude, Superhuman. That 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 quote.

We should ask Raul 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.

Yeah. You probably know 50 % of the features.

Right. Like, do you use remind me of this?

I do. Okay, great. Do you use labels?

Do you do snippets?

I do. Okay. Yeah. So it was all there when I started using it for three, four years ago.

I think a lot of those things have gotten better and better.

Yeah. So it's just that like, polish, polish, polish, polish.

Um, I really like want them to make snippets multiplayer.

I want to share my snippets with your team.

I love, yeah. So like, I want to have David's pass emails.

They're so nice. I don't pass email anymore.

Like you do it on the phone.

No, no, I just don't do email.

I just don't email anybody.

You know, when you pass my company, I'm 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.

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 pick.

Oh no. I get it. I don't, I don't, I don't, I basically don't take a pick 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, because as you are too, but with acquired, where like, you know, we have every six months, we have six companies that we work with on the show as our sponsors and our partners and we get to know them really well.

It's modern treasury, and I'm now an investor in just about all of those companies.

So it's not like they're pitching me.

It's growth stage investing.

Yes, they're not the winner.

Yeah. They're not priced as if they're the winner most of the time.

Yeah, exactly. They're gonna just keep compounding.

Good luck. Yeah, pricing is going to be hard.

Well, we'll see. Depending on entry price.

We'll see. Yeah, I don't know what's going to happen to these companies after, you know, the flat is the new up, but I think, you know, 50 % haircut is the new flat.

Well, public comps got hit 50 plus percent.

Yeah, I mean, they got hit harder again.

Yeah, I mean, I'm buying equities right now.

I've been doing it at Jtrading .com and I am going to buy more.

Sorry about all my picks a couple of weeks ago.

Which one? Whatever I thought, it was a certain while ago.

I actually love Taiwan Semiconductor.

Stitch fakes was the other one.

No, Stitch Fakes wasn't yours.

Twilio was yours and I love that one too.

And I like Shopify as a pick.

I'm actually really enjoying it.

It's really not investing advice, but it's balancing out my understanding of what public success is compared to private.

And so for me, it's just the way like, am I going to fight with a blast or no, I'm a Jedi, I use a lightsaber.

But I'll learn if you look at the very best, it's not as elegant.

It's helpful. It's really helpful.

If you look at the very best people, the best GPs, in venture over the past two decades, they all trade public stocks and they do it for the same reason.

They're going to fight with the saber, but like they want to know how to also use a blast or how to fight 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.

And early stage investing, it's almost silly to compare it 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?

Yeah, I'm really enjoying understanding what the founders of those companies go through versus the founders of the private companies that go through it.

What the board's decisions the board has to make of a public company versus the board of a private company.

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

But yeah, especially given the market right now, be careful.

But you could you could also find me to do that.

But it's just it's been through the show.

Now you have relationships with public company founders.

Sure, of course. You can.

If I really wanted to, I'm sure I could lobby.

Oh, you don't have to be on the board, though.

You can have a relationship doing the analysis and I'm doing it anyway with Molly every day.

OK, you know, Twilio's or Adobe's.

I just bought Adobe this week when they bought figs.

So funny, so did I.

Not investment advice, not investment advice.

But I was like, they bought Figma tanked.

OK, so here's my theory on this.

They bought Figma tanked and I was like, why did why do people hate this?

And they're like, oh, no, Adobe is admitting defeat and that like they can 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 50 X revenue multiple because of the network effects that Figma has and obviously all the product stuff.

But if they can get that through Adobe's channel, like I think that is an absolute win win acquisition and all these people that are like, oh, they're going to ruin it.

They're going to kill Figma.

No, they're not. That's why they paid 20 billion dollars for it and have a gigantic bonus for Dylan to stay on board.

Yes, they're taking a YouTube approach.

I think everybody in M &A knows now like or it's 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.

Yeah, you just discounted the right move.

Fantastic. We'll be like people are like, oh, you know, the Warriors signed Kevin Durant.

And you know, we're going to lower the biggest odds of 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 lower the cost of the tickets.

OK, I'll buy courtside seats or, you know, or they're lowering the odds.

I was in Vegas. It's like, wait, why are you lowering the odds?

Their odds increased.

I'll place that bad.

So it's just an obvious bet.

And then there's all that's left is Canva and Melanie is awesome.

Totally different thing.

But yeah, and they have a free Canva already.

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

Yeah. There's a group of MBAs who penciled out that spreadsheet with Figma.

No offense to MBAs who are listening.

And they said, hey, boss, if X, Y, if X, Y, Z.

And they said, 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 cost and then we blend it with the Adobe suite, OK, 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. But they may not have all the non -designers.

Only designers pay Adobe.

Right. Well, they have marketing cloud, but that's a totally different set of...

But when you look at Figma, like I got a Figma account, like people who are doing giving feedback on designs, the business side, the sales side can get into Figma.

Plus they got the whole creator class.

Exactly. So I think that you're opening up the aperture of who design software is for with Figma.

It's for BD. It's for the CEO.

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

Oh, legal should come in and take a look at the product.

Yeah, buy them a seat.

So it's like Slack is for the dev team.

And it's like, yeah, and the sales team and ops and anybody else might as well be on there.

Because that's where everybody is.

So that's one of the things you have with Figma.

It's like everybody's gonna have a Figma account in the future.

Just watch the product team build the product and put a comment in.

And who cares if it's a hundred bucks a year?

It's a cost to do in business.

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

So like I tweeted this, but like if I have a castle and it has a moat around it that is much wider or deeper than your identical castle, shouldn't you pay more for my castle?

It's more defendable.

Hundred percent. Like the virality of, I think Saks made this point on all end two weeks ago, which was like if they're paying 50 X now and the company's growing and they're paying 20 X next year, 25 X who cares?

It's such a high growth company.

And then I was just thinking, well, somebody's got a theory there.

And when I sold web logs to AOL, people are like, oh my God, these people are idiots.

They gave $30 million to, you know, for web logs, Inc.

They want a 200 K in revenue.

What they didn't realize was AOL, autos, AOL, tech, AOL lifestyle, those were sold out at like a 90 dollar RPM revenue per thousand pages, the ads, different CPMs.

So then they would put in a gadget or an auto blog 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 or $100 ,000 in ads a day on a blog.

And those people were like, great, because it was costing AOL to make content like $500 per piece of content, $3 ,000 per piece of content on AOL .com slash autos, whatever.

And we were doing it for at the time, five bucks a blog, $5 a blog post.

Because we said, well, people can write for an hour.

So it's 20 bucks an hour and it's $6 minimum wage.

It means that's 50 years.

The immediate game has changed so much.

I was like, you guys were doing 200 K annual revenue.

We had done 200 K to date.

Holy crap. Over the 18 months.

What is it? I mean, now like the world we're in today, like.

People looked at the multiple and they were like, J Cow just robbed.

And I was like, okay.

$30 million sale. But now I know.

I look like an idiot.

What do you think? Like here's a.

I look like an idiot at five years old.

And that's the best, the best M &A is when you look like you rob the bank.

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

You too. Figma will be in this category.

Like, yeah, when they bought Instagram, they're like 30 people work with this company and they gave him a billion dollars.

You guys are morons and now it's a hundred.

Here's a thought exercise question.

Obviously irrelevant because you don't monetize it.

What do you think the enterprise value of all in is?

Well, it would do $10 million in.

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

Shemak pulled me aside at some point and was like, Hey, Shemak, like just, we're friends.

Like you're all, your next fund won't be bigger than the rest.

Now it's like, you know, when you have a friend who can be like, Hey, dumbass.

Yeah. Like that's a good friend.

So I appreciate you not saying that.

And he's right. And it's playing out.

Um, and we had a rule, no, um, no talking our books on the pod, but we kind of talked about it and we're like, the pod is great when we talk about our bets.

So explaining our bets, not talking our book is the new philosophy.

So like, you guys just started doing that about his stack.

You know, um, I break that.

Yeah, you did. He just found a target for it.

Shemak talked about, um, the, uh, healthcare company, the healthcare company, which is, I mean, we wanted to talk about that because Shemak and I both agree.

Like maybe we're, I mean, maybe, like we're definitely overprescribing these drugs to kids, like for ADHD and attention drugs and adults are taking too many, I think that that's not disputable.

Uh, I think all the science is showing that.

Um, so, you know, to make software that could help kids with ADHD is like noble.

Um, but I think people want to hear us explain our bets.

So, you know, explaining our bets, I think is kind of a cool aspect of the show.

Talking your book is lame, but explaining your bets is cool.

So anyway, um, in the event did a couple million dollars, had a small profit.

Um, but it was the number one tech event of the year by far.

Right. So, you know, I'm kind of bummed that, you know, Freeburg's a little bit of a blocker for it, but I might turn them around and we'll have a vote maybe on the Well, I'm going to do another one.

The question is, am I doing it under the all in brand or do I have to create a new brand for it?

And so I told the guys, listen, I'm going to do it again.

Well, co -conference is done.

So like, there's a vacuum.

Co -conference is done.

Yeah. They need a new host.

Um, that's crazy, like it's such a value.

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, um, in terms of like, she does stuff and then she moves on to the next thing and tries like, you know, it's kind of my approach as well, which is like, Bob Dylan, you know, said like, don't look back kind of thing.

And he always tried to make the next album and forget about the past one.

And much to the chagrin of people who loved him as a folk artist and didn't like, 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 electric guitar.

Are you guys dumb? Like, did you hear all along the watchtower?

Like this is incredible.

Um, and so I think, you know, Kara Swisher like moving on, but Jim said he's going to keep doing it.

And you know, it's probably a small list of people who could actually host that credibly, you know, which is small list.

Um, and so, which you're definitely on.

I am. You think, how can you not be on work?

I'm not even saying that to like, make you feel like, yeah, I'm pushing a little bit.

Okay. You're, you're joking about being humble.

But if it had that kind of prestige, it seems like Friedberg would want to do it.

It seemed more like the thing he was averse to as the like.

Yeah. I mean, whatever the issue is, like, we found our issues.

We will have issues.

Um, but, um, I think the, there's basically two possibilities for all in summit.

Um, I'm going to present it to the boys, uh, and say like, here's the plan.

Yes or no. And we agreed.

We'll put it to a vote.

So we put it to a vote.

If three of us want to do it, we'll do it.

And if two of us want to do it.

Then we can't. Uh, and if I already, Friedberg 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.

Um, and the fans can decide if they want to come or not.

And partially in. Exactly.

So, you know, it's up to the boys.

Um, so I want to do it, but it was like a pretty great success.

Call it. Do you already have call ins?

Yeah. Well, yeah. And I started doing, um, I started doing a call in.

Show called after all info last two episodes where I took calls about the last episode of all just to support David, because I don't think people remember how great that app is and it's really made great progress.

So I want to be supportive of him and I have a small investment in it.

And do you, um, very meaningful, but on the one hand this is ridiculous.

Say on the other hand, it might be ridiculously low.

Do you think 50 million to answer your question?

50 to a hundred million.

I mean, as a top 40 podcast, it's worth at least 50 million on its own though.

But I mean, like economic value that the four of you.

Oh, who knows. Over the lifetime.

If Chamath or Saks 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, possibly 10.

You know, like, so yeah.

That's the thing. Like I think like, man, web blogs, like you were doing 200 K of revenue.

You sold it for 30 million.

Pretty great takeaway.

And now look at this like, you know, yeah, I mean, listen, I hope it keeps going.

And I hope we can keep it on track.

And, um, you know, I, I love doing pods.

This weekend startups is a juggernaut as well.

You know, it's been sold out for 10 years and all in is, what is that?

Like two quarter million listeners or something.

Yeah, something that range.

Yeah. I mean, it's hundreds of thousands per episode and yeah, it's very niche podcast.

You know, I'm not trying to make it all in, um, I'm trying to make it for founders.

And so, you know, if in order to make it bigger, it'd have to be worse for founders and I want founders and capital allocators to listen to it.

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I'm not trying to move up the rankings.

I don't mind, you know, hanging with, you know, all in being number one in tech and then hanging out with you guys that, you know, slumming it at six to 15 with you guys and the rankings it's like, that's where we belong.

Like I got number one on one, but who's counting?

Whatever, you know, like that's where we belong with these things, right?

Like it's, like it's a niche podcast by definition, right?

Like it's not supposed to appeal to everybody.

And you try, if you want to appeal to everybody, like read the Bible.

Like that's right. If you go to that, this is the, like reads Bible passages and he, and huge, it's like literally true crime, true crime religion, read the Bible or Ben Shapiro dunking on libs the end.

That's like, that's how you get or do a daily, but Joe Rogan's out, right?

He's on Spotify. You know, he's not in the other ranking.

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 capital would be a fun acquired episode is a Howard Stern.

I feel like it's underappreciated how much Howard Stern.

That's the playbook.

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

Enough for sure. He wrote the playbook for all of us.

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 shocked jock stuff, but he in his later years became a great interview, great interview, a great interview where he really refined his technique.

I really appreciate that about him.

And he created characters.

Sound familiar? Yup.

He branded them. Yup.

He showcased them, the whack pack, you know, all this stuff.

Did he ever do a event?

He used to do live events.

He did the US open sores where, and then he would do Howard Stern's like New Year's Eve celebration.

So yes, he did the equivalent of those in New York, but it was a very New York thing.

So he like, he played tennis against Baba buoy.

And, but I mean, he got 10 ,000 people to show up and buy tickets to a tennis match that they pumped up, you know, like for whatever number of months.

I remember this from my childhood and then he did his books, which were phenomenal.

He did a movie. He did a movie.

He did TV shows. So he's done a lot of stuff and I, I'm just starting the process of doing a reality show right now.

So literally going to do it.

Are you really? Yeah.

I mean, I had you or the besties or just me 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, you know, we would have to show up in a location.

We'd have to do it weekly.

You know, there'd be some format, some shiny floor, whatever it's, it's a, 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 Ramsey kind of vein, you know, where I'm helping founders.

I think it would be great for reach.

So I'm, 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 shark tank judge.

I had been, they had reached out before Mark Burnett had reached out early on when it was dragons then, um, right before when they were going to bring it here.

So when it was dragons, then they had reached out early, but I wasn't very successful back then.

Um, I wish, but you know, I think now I think I would have the credibility and the advice to give that I could do a Gordon Ramsey style show that would be very entertaining and educational and be completely different than, you know, the fundraising aspect and the pitch aspect of shark tank.

So I'm not going to do that, but I'm, you know, I've got, you know, the, I won't say which one, but a very major.

The major, you know, a reality TV folks reached out.

I think in part, founders and companies feel comfortable.

Like I feel like a really amazing window and insight would be the type of conversations that you have with a founder as they're building the company.

So they would have found companies be open to that.

Yeah. So the NBC show I had done the pilot for, which never made it on air.

Um, um, what was really good was really about, you know, me incubating companies and, uh, they spent like four or $500 ,000 doing the pilot.

It was really good.

And it would have been a big hit.

Did it get canceled because of the hardwood scene stuff?

Yeah. Wow. So they were just like anything that was in his company.

And all the IP is dead because he's a monster.

And so anything associated with it.

But you got to remember he did project runway.

So he had done some of these giant shows.

People don't know that about that.

And so that's why I forgot that had the TWC at the beginning.

So, you know, I just NBC, you know, I NBC bought the show in the room, loved it and did the pilot and came close.

And Shemaat was on that episode.

Actually he did the pilot.

Oh my God. Oh, he was like, he was like my VC friend who came in and it was hilarious.

It's no, it's hilarious.

Um, but, uh, yeah, I'm, I'm excited to do it.

If it works out, it works out.

If it doesn't, you know, no skin off my back.

Uh, but I like the media space.

And then, you know, I, this is the thing I'm choosing to do media because I get joy out of it.

I'm 51 now I'll be gone soon.

Like, how would you enjoy?

And I'll be gone soon.

Well, you know, you never know.

And, uh, you know, I've had two friends.

Yeah. I have two friends who died young and I'm just like, I, you know, I talked to my mom.

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 then so when the guys break my chops about that, I'm like, guys, it's not my priority.

Like literally maximizing money is like, well, also like you're probably at a point now where like, literally not in the top 10, what is more money going to do, like, you know, you guys understand my life.

Like it is ridiculous and charmed.

Like I can do whatever I want.

Have enough money to do it.

I'm out. My kids are fine.

I can have whatever I want.

I don't care about like a third home.

Like it's I have a ski house.

I have my regular house.

It's good. I'm, I'm good.

My kids have their college paid for.

Like a hundred percent.

I literally do not care about my mind.

Do you feel like that's a demon that you fight is like, no, any alert 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 want it to be seen.

I wanted people to recognize my greatness.

Like any person recognize me for what I do.

I got all that. It literally does not even come up my radar to have more money is the last thing I'm thinking about.

What are you want to have?

I do want to 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.

I want to be Mount Rushmore for all investors.

So when you guys do your thing and 10, 20 years and it's like, okay, you know, here's Doug Leone and Moritz and you know, uh, here's, you know, John door here's Gurley.

Like it would, if we are making them out, rush more, you want to be on that with them, I would like to make it there or at least be in the conversation.

All right. Listeners, we kicked Jason out of the room again, because we have our next sponsor of the episode are very good longtime friends over at tiny.

The Berkshire Hathaway of the internet.

If you'll recall. Indeed.

So there so much so the Berkshire Hathaway of the internet that as we told you about a few seasons ago, they literally built a business on the internet, selling bus of Warren and Charlie that you can order for sure nerds.

Sure. Nerds. That's not what we're here to talk to you about today.

They've got something new to share with us this season that we've been talking a little bit about, uh, kind of from the founder angle, but we want to share with you from the VC angle.

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 Medallab 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 Medallab.

And so they started buying more and more and more businesses.

And so now with this awesome portfolio dribble pixel union, creative market, 80, 20 girl boss, 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 you over a 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%, uh, and it can get profitable or it is profitable.

Well, most of the time it makes 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 like 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 by the company from the VCs or a lot of the company from the VCs, the VCs get them some or all the way back, get their time back, get off the board.

So they have capacities 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 or tiny is very good at figuring out structures that make sense to align interest.

Yes. It's really super cool.

Like I honestly like I've talked with a bunch of folks of varying different financial groups and institutions over the years who have had some version of this idea and it's never gotten off the ground.

And I'm so glad that tiny is now doing it and they are the perfect ones to do it.

And this is the perfect time to do it.

So very excited for this to exist.

Yes. Well, if you are running a business like that, or you are invested in a business like that, or your friend is invested in a business like that, you really should shoot a note too high at tiny .com and just tell them that Ben and David sent you.

Don't tell him Jason sent you.

He's not here right now.

You can say Jason sent.

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 Rockmore.

Try to imagine you're retiring.

Yeah, I think it's possible.

I met Don Valentine when they were like, you know, he was not an 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. 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 on your Mount Rushmore?

Well, I mean, you got to have Don Valentine, right?

That's just not possible, but how are you scoping it?

Cause 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 okay.

So do you go with John doors in there along with, so if you're doing firms, it's a lot easier cause you get close law door and, um, Perkins, Tom Perkins.

You get the three of them at once you do.

So you know, which people forget the new postal spent a decade at Kleiner Perkins with John door, like, yeah.

And you, and you had, yeah.

So, I mean, you, you look at that firm, it's like, that's like the OKC with like James Harden, you know, whatever, but then you have Doug, Leonie, uh, Mike Moritz and time rule off.

Yeah, but all of them, they're active all 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 is kind of how you might look at it.

You know, you definitely have to have.

We just did. You got to have the fab for era of the fab for era benchmark was truly something special.

So I mean, it's kind of like it kind of builds itself the Mount Rushmore right now.

Right. It's going to be Sequoia Kleiner benchmark.

And then we're like, we're going to have a big debate on the fourth arm.

Right. Like, is it what just depends how wide we're willing to scope it?

Is it like traditional series?

A type venture firms or angelous?

And of all that's had a huge impact.

You put my C in there.

Do you put why? See your tech stars both have a huge impact.

Do you put, um, you know, uh, what else could be in there?

That's just, are you for founders fun?

You can say YC and I had stars.

It's completely different thing 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 returns.

Yeah. But tech stars, I think it was a little before white combinator.

But anyway, you definitely white commentators, you know, in running for that four spot, I guess, and then who else would you put in there?

Masa. Oh, well, no, I mean, but that may be the impact on the industry.

Maybe, I mean, not found a try.

Yeah, I don't know.

Depending on Excel would be in the running.

It's for sure. It's Ron Conway.

I think the way you kind of have to define it, which is unfortunate because it means that it's going to be a long ass time before your firm hits Mount Rushmore is three successful generational transitions where each of the generations would have been on Mount Rushmore.

So then let's just do this instead of Mount Rushmore because you're, we're talking firms.

So for firms to do Mount Rushmore, right?

So I think if you were just going to say the hall of fame, yeah.

Oh yeah. Just the hall of fame.

And the hall of fame has let you say, oh dude, we should open the venture capital hall of fame.

The venture capital hall of fame.

Capital allocator hall of fame, top 25.

I was trying to figure out when we were doing the benchmark episode research, which will be out by the time this comes out.

2480 Sand Hill Road is a very special building.

It was the forethought PowerPoint.

The Quadras complex.

Quadras complex office.

Then it was Microsoft Silicon Valley.

Oh, no. I'm so excited right now.

It's like, wow, we're aggregated all the other people.

Everybody else who cares about this is listening right now.

And like Sebastian who wrote The Parallel said, yeah, yeah, yeah.

You guys are taking this way too seriously.

It's not that important.

But then we're like alone yelling David's house about a fictional hall of fame.

TVI, Meryl Pickard.

TVI. That's a good, wow.

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 like I think we got to take out at least just to put the museum, the whole thing.

A whole thing is something that we should go right on.

We should just do it.

If we'll just do it like, yeah, yeah.

We'll just do it like every year we induct somebody.

We'll get up there.

The three of us and be like, yeah, yeah, yeah.

This year we're inducting.

This should totally be a whole thing.

We should totally do this.

In Ohio exists. Hilarious.

You know, Cooperstown, although there is a what do you call it?

There, it would be our Cooperstown.

Yeah, there is a computer history museum, but it's not for the PC, which is totally valid for capital allocators.

It's not for people like there should be a Hall of Fame.

And do we like, do we Midas list style ask people for the real hard truth?

No, no, no, it's about impact.

You know, we decide the three of us.

We decide it has to be impact on the game.

Does the NDC have like a Lifetime Achievement Award?

Is that the closest thing?

It does exist anymore.

No, it's about impact.

Legacy, like the intent of the person.

Right. This is why like Paul Graham would be like, you know, first ballot.

This is why. Yeah. Okay.

Who are the first ballot interests?

So obvious. We've already talked about it.

We already talked about those are all first ballot.

Do we have anybody who we haven't talked about or who is non obvious, but would be a first.

Well, you can't write 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 sports Hall of Fame.

So you got to have a yeah, you gotta be you're not playing in the league anymore.

So Paul Graham 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, yeah. Separate companies.

But like yes, capital allocated lowercase, lowercase, they've been great at placing bets.

Yeah. But you're right.

But we have to face.

This is probably the most successful angel of all time.

Yeah. I mean, if you just did it on you know, when you're when you're looking at it, I think you'll look at impact.

Like impact on a game legacy, like so is Carmelo Anthony Hall of Fame?

Of course he is, but he didn't win a ring.

But you know, just Carmelo Anthony, right?

Like or Charles Barkley didn't win a ring.

But okay, so then we got like Arthur Rock.

Like 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 Koozie or whatever.

They're 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 to leave and you have people for the league.

You have people in the league.

Yeah. You can generational shit right here.

You know, Patrick Ewing.

Yeah. You know, I think like you look at girly, like he's part of that Patrick Ewing generation, right?

Like that Kim Elijah on Charles Barkley generation.

You start talking about Founders Fund or YC or Angel List.

Like, okay, now you're talking about more modern era.

Yep. Still going modern era after 2000.

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

Do you know as we haven't talked about entries in our what's in this conversation?

Oh, who cares? No, impact on the game.

They're in. Both of them are in.

For sure. I know. No doubt.

They totally are. I guess.

Impact on the game.

They totally changed that.

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 adventure.

I find it quite soulless if I'm being honest.

Like, I feel like it's a giant index on venture and I don't think that their hearts are super into it.

Well, I do think they have interesting ambitions though.

I think this like that's the problem.

It's more ambition than soulful.

But there should be a JP Morgan or Goldman Sachs of Silicon Valley.

For sure. Yeah. Why is it?

Why does Goldman Sachs manage the money a bunch?

I just feel it's too...

Okay. Fine. But I just feel like it's too premeditated and less soulful.

I feel like it's a soulful business where like your intentionality and your relationship with the founders really matter.

It's not the craft.

I mean, it's like the literal antithesis of it.

It's an industrialization.

Yes. It's the industrialization of it.

It's the factorization of it.

And listen, I'm sure it'll be very successful at the end of the day.

All the returns will be great except for the crypto stuff.

Well, I mean, it'll be an email version.

Because like when you get the law of large numbers, you have mean reversion.

Exactly. It will be mean reversion for sure.

I mean, that was at some point they leaked a lot of their returns and they were like, Eh, not fair.

That was the 2015 thing.

Well, they did actually.

It was early. So yeah, that was stupid that the journalist 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 or Sequoia.

And we, I mean, made a lot of hay on the fact that they had, that they made 11 billion dollars in profit on Coinbase.

And like, I do not think they sold out of that.

So they did not make 11 billion dollars in profit.

Yeah, fair enough. Well, I mean, it's timing is everything.

We'll see. I mean, crypto.

It's interesting too.

I mean, having just done this Benchmark episode, like the Benchmark Fund 7, one of if not the best institutional sized fund of all time, just like unreal.

20 to 25 bucks. Even that, like, the fluctuation in the marks on that fund and it'll probably end up between 15 and 25x, maybe, but like, but it fluctuates up and down.

Of course. I mean, we live in a very volatile, volatile time right now.

So 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.

No, I just, we could just do it as like a dinner.

We just literally have...

We don't need a space.

Every year we get a, we get, 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 posters.

We do it like the sports where you have the person who's being inducted chooses who inducts them.

Sure. That's fun. So Rulof does Doug or whoever does Moritz.

Yeah. But John Parker does Moritz.

Mike chooses who, you know.

Yeah, go. He can have Larry Sergey come up.

He can have Larry and Sergey come up.

Totally. John Doar would ask Bezos.

I mean, it's killer.

It's a killer idea.

I mean, we just do Bezos, Doug and Mike.

Yep. And then who inducts who would that film?

If we could do one in Memorial.

Yes, exactly. You know, whatever.

Yes. On time. 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 want to get to 25.

So maybe it's you want to get to 25 to 50 over 10, 20 years.

So 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 hole full of fame.

Right. There are people that be a very interesting Horowitz way to do it.

What's the total assets under management?

You know, and it's like, okay, dude, we get it.

Nickelback sold a lot of albums.

Yeah. There was a Nickelback.

No, I didn't read that.

You said that. You said it.

I wasn't talking about it.

Oh God. Oh God. I'm not saying that they're not.

No, 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 Andreessen?

Like, I think it's a conversation, you know, and if you, because Ron Conway, when I came into the industry, like there was at one point, I was at the crunchies and Ron Conway at one point, like somebody said like, Hey, can everybody stand up?

Who said Ron Conway invest in their company and a hundred people stood up.

And my mind was like, Oh, Whoa.

Angel investing is cool.

I mean, I wasn't an angel investor at the time.

It was, you know, long before I became a scout.

But that, I always remember that moment when like a hundred people stood up.

That inspired, partially inspired.

The scout program was that would give you the, is that what like put you in business as an angel investor?

What happened was I had, was your Uber investment you personally, or was that Sequoia's money?

That was Sequoia's money.

And we were like, Rulof and I were trying to figure out like, do we let people know we're doing this or not?

It was like a big controversy at the time.

Like we want to keep the stealthy, but I mean, Travis knew.

But you know, it was, it was a pretty great deal.

You know, it was like, you know, at the time they carry 50, 50 at the time.

They dropped it down after that.

Yeah, I bet. Every time I'd see Doug Mioni, he's like 50 % carry.

And they had 30 % carry at Sequoia at that point, I think.

Yes. And if I were you, I'd be like 50 % carry to them.

I can't believe it.

No, no, Doug always, they're so classy.

Doug always made a joke, would always make a joke.

I was like, 50 % carry?

Oh, God, we get 30, you get 50.

Which is funny. We get 30.

We get 11. A lot of it.

It's pretty funny. Pretty funny to turn that.

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 in 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.

Like a deal on. Exactly.

So the human species getting moved forward by, as Steve Jobs would say in those commercials, like this is the crazy ones.

They do need fuel. They maybe don't have an idea of if they should even build this company.

And I think the capital allocators really come in and say, here's some fuel.

Here, go fight that war.

It's fuel and it's belief too.

I mean, wait, your story about Com is not uncommon, I think, amongst founders.

Oh my God. I mean, look at, I mean, 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.

Yeah. There's a lot of existential moments where things go to zero and like...

So can I ask you as we start to like drift toward the end of the episode here?

That's your line. That's your favorite line.

That's the Ben's signature line.

A glass here toward the end of the episode.

The drift towards the end of the episode.

Is this a good format?

Is our time together?

Is this different enough from our normal show?

Should we do this? Yeah, I think so.

What should we change?

Yeah, do you like this?

I think a casual glass of wine and just, you know, if you have friends of the pod and you want to go deep and talk about them and ever more casually, sure.

Yeah. I mean, I think it's a great way to just have somebody on again.

You know, so if you profile somebody like, I forgot that I had, you had done like the first episode with me and that was more about my career and more details and so I'm starting to tell stories over again.

It's like, well, let's talk about some other stuff.

So I think it's a different.

I mean, our audience was...

I like this format.

Well, part of what we, you know, like Lex has done so great with his show.

Yeah. 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.

It's not about that.

I don't know why he's in the tech vertical.

But I like the format and like Kevin Rose used to do with the foundation series and like...

I mean, long -form interviews like Howard.

I mean, I think Joe Rogan stole it from Howard.

Yeah. And I think it's now Lex stole it from Joe or I want to 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 he wanted to be Stern, I think.

And he eventually has some planted Stern in a way.

He did become Stern.

Yeah, he did become Stern.

And so good on him.

Right down to the serious Spotify.

Like right down to it.

He'd be doing Stern.

Like doing a platform.

Yeah, doing a platform.

Which is what Stern did.

Stern had multiple platform deals.

He did syndication first.

Then he did the Sirius XM1 because it was a new platform and he built the platform.

He used his number one show to build their platform.

Which is, I think, what...

Which is... But actually, to bring it all the way full circle back to Charlie Rose.

He was like a... I mean, he did more than business but like he would have...

He did culture, business.

Anybody in New York, because New York, everybody in New York was pretty fucking interesting.

He could have somebody from Wall Street, a publisher, an author, somebody who does films.

He would have Spike Lee on it.

He'd have Woody Allen on.

He would have any actress on who was doing something interesting.

Any novelist. Margaret Atwood.

Anybody who 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 -form.

It was like a little more jazzy.

A little bit more acoustic.

I like this format for you guys.

Yeah, sure. 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 kinda want to do that of tech.

But like... You and I don't know who the one of us is bringing somebody.

No, that's not your racket.

You guys are not getting...

You can't make... You gotta know the person's background much better.

But they all seem to carry a certain charisma with them that our industry doesn't have.

But maybe it doesn't have to be the surprise as much as like...

Yeah, it's true. Well, the other thing is that 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.

It does incredibly well.

It's a top 10 or top 25 podcast.

Is it part of a network?

Is it part of Spotify or something?

I don't think so because I see it on iTunes very high.

I don't think so. It's really weird that like Spotify doesn't allow Joe Rogan and call her daddy on iTunes because the advertising would be huge.

So why not bake the ads in and put them over there?

There's some MBA that's run the numbers that says it's more valuable if it's driving new subscribers to Spotify.

I guess that's it. I guess that's it.

Oh, I guess they want to be able to have those new subscribers so when they go renegotiate with the music.

So they're doing audiobooks too now.

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, let's get really hot in here.

It's getting so hot.

For those of you who don't know, we're in like a sauna, a new ...

Yeah, it's David's new house.

David just moved. David's got a new empty house.

There's no way of convincing.

It's sort of like the shining.

There's no furniture.

We just furnished this room.

This is all from Craigslist, all of it, literally in the last two days.

That explains the smell.

All right. Listen, you're a rich dude.

Just go on and buy some Craig's barrel.

You can't all be Jason Callicatus.

No, come on, man. I know those fees.

Oh, my God. I love Craig's list.

I love Craig's list.

I love it. You buy used furniture on Craig's list?

All the time. I do not buy new furniture.

All right, let's kind of stop.

I bought a temporary couch on Craig's list.

It's the thrill of the market.

You're gonna get robbed.

Don't do that. It's too crazy.

Craig Newmark, I love you.

All right, with that, our thank you to Vanta.

Oh, 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 heard them live with you because we felt very strongly that it was, we wanted to make better use of your time.

I love reading the ads.

Are you kidding me?

Do you want to read our Brex ad?

They don't sponsor my Pots and No.

Maybe they have. I don't know.

There's also a lot of ad -libbing in there.

Brex. I know a lot of people who use Brex.

I think we use Brex.

It is one of my companies.

If you're enterprise, if you're global, by far the best corporate spend management.

It's much more than a card now.

Yeah, for expenses and everything like that, right?

And then they've kind of expanded behind that.

You can give cars to each of your employees and then if they screw up, you can turn it off or something.

Yes, exactly. They jump through some budgets.

Yeah, you don't want people to jump on the fence and go crazy.

All the listeners know because they heard it like an hour ago.

They're very familiar.

Oh, that's in here.

So anyway, thanks, but shout out Brex.

So that's Brex. Shout out Brex.

Use the promo code twist.

We share... Use the promo code twist.

We share this last sponsor.

These are great folks.

These are like dear friends and geniuses and raccontours.

Masterworks? No, no, no.

Good guess, though.

Think smaller but bigger.

Literally small. Oh, gosh, I can't believe it.

But secretly huge. Tiny.

Oh, tiny. Of course.

Yes, they're buying companies.

Yeah, 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 and sell your company.

Secure the bag. Secure the bag.

Let's go. That's my favorite takeout line.

Secure the bag. Let's go, man.

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

It's not like getting home with the bag.

You get that tiny bag.

You get that AOL web blog exit.

They call it... Oh, man.

Let me tell you something.

I'll tell you the story.

What did you do when you secured the bag?

I'll tell you what happened.

I got... It's a funny story.

I'm in my office and I got Bank of America and I got like low thousands of dollars in my bank account.

I got an American Express card with negative 10 on it and a Visa with negative five or 10 on it.

And I'm sitting there and they're like, oh, wires are good.

You know, the BD people are AOL.

And so I'm like hitting refresh on the thing.

This is 2000... Five is six.

I'm hitting refresh.

And then bing, bing, bing, bing, bing.

All the numbers come in for the whole amount.

And you own most of web blogs.

Bryan and I were equal partners.

Then Peter Rojas had some ownership and then Mark Cuban was our big investor.

And by big investor, he put 300K in for 5%.

So that was a great outcome for him.

Oh, wow. Yeah. Or more.

Maybe on 10%. I think on 10%.

Anyway, long story short.

My wife comes in. She said, you OK?

And I said, what? She said, are you crying?

And I reached out 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.

You know, my dad had lost the business.

It was a very cathartic thing for me.

And I think people, you know, who are already rich, you know, or maybe who come for 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.

It's a tiny bag. But it's filled with diamonds and cash.

You just open it up and say, thank you, tiny.

Thank you, tiny. You secured the bag.

Acquired .fm slash tiny.

No, it's not. They don't give us a thing.

Oh, no, we don't. No, it's right.

And now time will sign up.

You secured the bag.

Is it the Hyatt tiny?

And tell them that David said you.

Whatever it is, just know that tiny one.

Tell them that Ben David had Jason.

You can mention Jason, yeah.

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.

That I tried to buy a Ferrari.

They wouldn't sell it to me in Beverly Hills.

You were the riffraff?

No new money or something?

Yeah, basically. I went in there and they're like, oh, yeah.

I like to buy a Ferrari today and the 430 and they're like, oh, we don't have any available.

And I was like, OK, can I put myself on the waitlist?

We're not taking the actual waitlist.

So I said, can I ask what do you do here?

He's like, we sell Ferraris.

I'm like, to who? No, this is part of their strategy.

It's part of the strategy.

Part of the strategy was they have the Ferraris, but they don't sell the Ferraris to build a steel.

We're not adding any parts of the list.

I was like, well, how long is the waitlist?

He's like, don't even bother getting on it.

I was like, OK. I'm a cash buyer.

He's like, everybody's a cash buyer.

I'm like, OK. Can I ask you a question then?

He's like, sure. Come into my office with an espresso.

Want some Pellegrino?

I was like, no, I'm good.

You want some Pellegrino?

They let me offer me Pellegrino espresso.

And I was like, I have the same one touch.

And this Italian guy is like, I don't mean to be rude, but what do you do here all day?

He's like, well, we deliver the cars and we service them and we sell used cards.

He's a pre -owned, certified.

For more. And I was like, oh.

I was like, well, I would take a pre -owned one.

He's like, oh, well, the one you're looking at is pre -owned.

I was like, no, no, no.

The one I'm looking at, the four of the red one out there, that's the one I want.

That's got a sticker in the window.

He's like, yeah, we certify them.

We put the sticker on the window.

I was like, oh, well, that goes for $230 ,000 or whatever.

And so, yeah, what do you want for it?

He's like, 300. You're like, the sticker says it's good.

No, no, no. It's a potentially payback.

I said, the used one I was looking at, he's like, you can't get these cars.

And I was like, ah.

So you pay over 70 ,000.

He's like, but it only has 2 ,000 miles on it.

And I was like, 2 ,000 miles, 70 ,000 more than new.

I said, why wouldn't I buy a new?

He said, because you can't get them.

And I just, I'm such an idiot from Brooklyn who doesn't understand the concept that people would pay over the car.

And I'm just perplexing.

That would bother me too.

I was like, all right, well, let me think about it.

And I left. And then I was with my friend and I was like, um, and I had the rob report and it said like number one car was the Ferrari F30.

And they turned the page.

It was Corvette. C6 was the number two car.

And the starting line was make Ferrari buy two for half the price of a Ferrari and beat them off the line or something like that.

And I was like, let's go to the court.

Let's go to Chevy. So I walk in, there's Corvette everywhere.

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 $5 ,000 off.

I was like, yeah. So we go out on the 405 and we're driving the Corvette.

And he's like, it's a Corvette.

It's like you're going 70 miles an hour.

I said, I'm not, he says, I'm not selling this car to you unless you hit that gas much harder.

And I said, okay. And I punch it to a hundred miles per hour.

I said, yeah. How does that feel?

I'm like, great. I come home with the Corvette.

I come over the 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.

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.

Erasing. 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 that Tesla just destroyed.

Wow. The Corvette. And I was like, I'm doing something wrong.

And you know, then we switched cars.

I mean, and I was like, no electric.

Just going to be everything.

And this was the first one.

That, you know, first.

Yeah. That's amazing.

The prototype that's in space right now is the cherry red one.

That's the one. And there's a famous photo of me and Elon in front of the.

With his face. With that, that one's it.

But there's a famous photo of the two of us, you know, in front of my Corvette and his P1.

And I remember that night like it was yesterday.

Because we were. This is before the iPhone.

You realize like Robert Scoble was recording this on his Nokia, you know.

These are the memories, right?

Like crazy. This is the journey that you've been on.

Yeah, pretty crazy.

This is the stuff you just will cherish forever.

My life is unbelievable.

I am so grateful for it.

And thanks for having me on the podcast.

Thank you so much. Acquired .fm slash Slack.

Come join us. We'd love your feedback.

This is a new schtick.

Acquired .fm slash store.

You can buy cool shirts.

Swag. Slash Jobs. Find your next career experience.

You can get a couch.

That's right. Acquired .fm slash David buys you some smelly furniture.

My God, it is hot in here.

Let's go eat some food.

Let's have some sushi or Mexican.

I don't know what we're going for here.

So fun. Thank you so much.

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.

Acquired .fm at gmail .com.

Or tweet at us at Acquired .fm.

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've 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.

Awesome. Ten other winners will get Acquired t -shirts from our fancy new merch store, again, three minutes to participate at Acquired .fm slash survey or you can click the link in the show notes and thank you so much for helping us.

It really does help us run the show here at Acquired World HQ.

All right. Well, with that, our huge thank you to our sponsors for this episode.

We've got Vanta, Brex, and our friends over at Tiny.

Links for each of those are in the show notes.

And with that, listeners, we'll see you next time.

We'll see you next time.

[David Rosenthal Unplugged: A Candid Conversation with Jason Calacanis]-[ACQ Sessions: Jason Calacanis]

📋 Summary

The Unscripted Evolution of a Tech Veteran

From 'Silicon Eye' to Podcast Powerhouse

The Art of the 'Besties' and Moderation

Meritocracy and the Modern Founder’s Journey

Wealth, Purpose, and the Future

Conclusion: The New Media Model

🎯Key Sentences

📝Key Phrases

📖 Transcript