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ACQ Sessions: Jason Calacanis

ACQ2 Episode

October 4, 2022
October 4, 2022

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

If you want more Acquired, you can follow our public LP Show feed here in the podcast player of your choice (including Spotify!).



We finally did it. After five years and over 100 episodes, we decided to formalize the answer to Acquired’s most frequently asked question: “what are the best acquisitions of all time?” Here it is: The Acquired Top Ten. You can listen to the full episode (above, which includes honorable mentions), or read our quick blog post below.

Note: we ranked the list by our estimate of absolute dollar return to the acquirer. We could have used ROI multiple or annualized return, but we decided the ultimate yardstick of success should be the absolute dollar amount added to the parent company’s enterprise value. Afterall, you can’t eat IRR! For more on our methodology, please see the notes at the end of this post. And for all our trademark Acquired editorial and discussion tune in to the full episode above!

10. Marvel

Purchase Price: $4.2 billion, 2009

Estimated Current Contribution to Market Cap: $20.5 billion

Absolute Dollar Return: $16.3 billion

Back in 2009, Marvel Studios was recently formed, most of its movie rights were leased out, and the prevailing wisdom was that Marvel was just some old comic book IP company that only nerds cared about. Since then, Marvel Cinematic Universe films have grossed $22.5b in total box office receipts (including the single biggest movie of all-time), for an average of $2.2b annually. Disney earns about two dollars in parks and merchandise revenue for every one dollar earned from films (discussed on our Disney, Plus episode). Therefore we estimate Marvel generates about $6.75b in annual revenue for Disney, or nearly 10% of all the company’s revenue. Not bad for a set of nerdy comic book franchises…

Season 1, Episode 26
LP Show
October 4, 2022

9. Google Maps (Where2, Keyhole, ZipDash)

Total Purchase Price: $70 million (estimated), 2004

Estimated Current Contribution to Market Cap: $16.9 billion

Absolute Dollar Return: $16.8 billion

Morgan Stanley estimated that Google Maps generated $2.95b in revenue in 2019. Although that’s small compared to Google’s overall revenue of $160b+, it still accounts for over $16b in market cap by our calculations. Ironically the majority of Maps’ usage (and presumably revenue) comes from mobile, which grew out of by far the smallest of the 3 acquisitions, ZipDash. Tiny yet mighty!

Google Maps
Season 5, Episode 3
LP Show
October 4, 2022


Total Purchase Price: $188 million (by ABC), 1984

Estimated Current Contribution to Market Cap: $31.2 billion

Absolute Dollar Return: $31.0 billion

ABC’s 1984 acquisition of ESPN is heavyweight champion and still undisputed G.O.A.T. of media acquisitions.With an estimated $10.3B in 2018 revenue, ESPN’s value has compounded annually within ABC/Disney at >15% for an astounding THIRTY-FIVE YEARS. Single-handedly responsible for one of the greatest business model innovations in history with the advent of cable carriage fees, ESPN proves Albert Einstein’s famous statement that “Compound interest is the eighth wonder of the world.”

Season 4, Episode 1
LP Show
October 4, 2022

7. PayPal

Total Purchase Price: $1.5 billion, 2002

Value Realized at Spinoff: $47.1 billion

Absolute Dollar Return: $45.6 billion

Who would have thought facilitating payments for Beanie Baby trades could be so lucrative? The only acquisition on our list whose value we can precisely measure, eBay spun off PayPal into a stand-alone public company in July 2015. Its value at the time? A cool 31x what eBay paid in 2002.

Season 1, Episode 11
LP Show
October 4, 2022

6. Booking.com

Total Purchase Price: $135 million, 2005

Estimated Current Contribution to Market Cap: $49.9 billion

Absolute Dollar Return: $49.8 billion

Remember the Priceline Negotiator? Boy did he get himself a screaming deal on this one. This purchase might have ranked even higher if Booking Holdings’ stock (Priceline even renamed the whole company after this acquisition!) weren’t down ~20% due to COVID-19 fears when we did the analysis. We also took a conservative approach, using only the (massive) $10.8b in annual revenue from the company’s “Agency Revenues” segment as Booking.com’s contribution — there is likely more revenue in other segments that’s also attributable to Booking.com, though we can’t be sure how much.

Booking.com (with Jetsetter & Room 77 CEO Drew Patterson)
Season 1, Episode 41
LP Show
October 4, 2022

5. NeXT

Total Purchase Price: $429 million, 1997

Estimated Current Contribution to Market Cap: $63.0 billion

Absolute Dollar Return: $62.6 billion

How do you put a value on Steve Jobs? Turns out we didn’t have to! NeXTSTEP, NeXT’s operating system, underpins all of Apple’s modern operating systems today: MacOS, iOS, WatchOS, and beyond. Literally every dollar of Apple’s $260b in annual revenue comes from NeXT roots, and from Steve wiping the product slate clean upon his return. With the acquisition being necessary but not sufficient to create Apple’s $1.4 trillion market cap today, we conservatively attributed 5% of Apple to this purchase.

Season 1, Episode 23
LP Show
October 4, 2022

4. Android

Total Purchase Price: $50 million, 2005

Estimated Current Contribution to Market Cap: $72 billion

Absolute Dollar Return: $72 billion

Speaking of operating system acquisitions, NeXT was great, but on a pure value basis Android beats it. We took Google Play Store revenues (where Google’s 30% cut is worth about $7.7b) and added the dollar amount we estimate Google saves in Traffic Acquisition Costs by owning default search on Android ($4.8b), to reach an estimated annual revenue contribution to Google of $12.5b from the diminutive robot OS. Android also takes the award for largest ROI multiple: >1400x. Yep, you can’t eat IRR, but that’s a figure VCs only dream of.

Season 1, Episode 20
LP Show
October 4, 2022

3. YouTube

Total Purchase Price: $1.65 billion, 2006

Estimated Current Contribution to Market Cap: $86.2 billion

Absolute Dollar Return: $84.5 billion

We admit it, we screwed up on our first episode covering YouTube: there’s no way this deal was a “C”.  With Google recently reporting YouTube revenues for the first time ($15b — almost 10% of Google’s revenue!), it’s clear this acquisition was a juggernaut. It’s past-time for an Acquired revisit.

That said, while YouTube as the world’s second-highest-traffic search engine (second-only to their parent company!) grosses $15b, much of that revenue (over 50%?) gets paid out to creators, and YouTube’s hosting and bandwidth costs are significant. But we’ll leave the debate over the division’s profitability to the podcast.

Season 1, Episode 7
LP Show
October 4, 2022

2. DoubleClick

Total Purchase Price: $3.1 billion, 2007

Estimated Current Contribution to Market Cap: $126.4 billion

Absolute Dollar Return: $123.3 billion

A dark horse rides into second place! The only acquisition on this list not-yet covered on Acquired (to be remedied very soon), this deal was far, far more important than most people realize. Effectively extending Google’s advertising reach from just its own properties to the entire internet, DoubleClick and its associated products generated over $20b in revenue within Google last year. Given what we now know about the nature of competition in internet advertising services, it’s unlikely governments and antitrust authorities would allow another deal like this again, much like #1 on our list...

1. Instagram

Purchase Price: $1 billion, 2012

Estimated Current Contribution to Market Cap: $153 billion

Absolute Dollar Return: $152 billion

Source: SportsNation

When it comes to G.O.A.T. status, if ESPN is M&A’s Lebron, Insta is its MJ. No offense to ESPN/Lebron, but we’ll probably never see another acquisition that’s so unquestionably dominant across every dimension of the M&A game as Facebook’s 2012 purchase of Instagram. Reported by Bloomberg to be doing $20B of revenue annually now within Facebook (up from ~$0 just eight years ago), Instagram takes the Acquired crown by a mile. And unlike YouTube, Facebook keeps nearly all of that $20b for itself! At risk of stretching the MJ analogy too far, given the circumstances at the time of the deal — Facebook’s “missing” of mobile and existential questions surrounding its ill-fated IPO — buying Instagram was Facebook’s equivalent of Jordan’s Game 6. Whether this deal was ultimately good or bad for the world at-large is another question, but there’s no doubt Instagram goes down in history as the greatest acquisition of all-time.

Season 1, Episode 2
LP Show
October 4, 2022

The Acquired Top Ten data, in full.

Methodology and Notes:

  • In order to count for our list, acquisitions must be at least a majority stake in the target company (otherwise it’s just an investment). Naspers’ investment in Tencent and Softbank/Yahoo’s investment in Alibaba are disqualified for this reason.
  • We considered all historical acquisitions — not just technology companies — but may have overlooked some in areas that we know less well. If you have any examples you think we missed ping us on Slack or email at: acquiredfm@gmail.com
  • We used revenue multiples to estimate the current value of the acquired company, multiplying its current estimated revenue by the market cap-to-revenue multiple of the parent company’s stock. We recognize this analysis is flawed (cashflow/profit multiples are better, at least for mature companies), but given the opacity of most companies’ business unit reporting, this was the only way to apply a consistent and straightforward approach to each deal.
  • All underlying assumptions are based on public financial disclosures unless stated otherwise. If we made an assumption not disclosed by the parent company, we linked to the source of the reported assumption.
  • This ranking represents a point in time in history, March 2, 2020. It is obviously subject to change going forward from both future and past acquisition performance, as well as fluctuating stock prices.
  • We have five honorable mentions that didn’t make our Top Ten list. Tune into the full episode to hear them!


  • Thanks to Silicon Valley Bank for being our banner sponsor for Acquired Season 6. You can learn more about SVB here: https://www.svb.com/next
  • Thank you as well to Wilson Sonsini - You can learn more about WSGR at: https://www.wsgr.com/

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Transcript: (disclaimer: may contain unintentionally confusing, inaccurate and/or amusing transcription errors)

Jason: It was a magazine.

Ben: Magazine was like the original platform. Have we started?

David: This is the trick. We've just been reading the whole time. Welcome to Acquired Sessions.

Ben: Yeah. All that stuff that you said beforehand is really juicy. I don't think we should put that.

Jason: No, definitely not. Definitely not. We don't want to tell people where the bodies are buried.

Ben: Well, Cheers, boys. Here we go. Is this the first one or?

David: This is the first in real life? Well, I think this is our ninth or tenth together, something like that.

Jason: A lot between the two pods. Yeah, for sure. Great to know your bliss.

Ben: This is the first time Acquired Sessions.

David: Acquired Sessions.

Jason: I feel like I should get out with guitar here and just play some Dylan.

Ben: This is your baby. What is Acquired Sessions?

David: Acquired Sessions is normally on the show, we are so scripted.

Jason: Yeah, you are.

David: We have a great time. We do four-hour episodes. It's awesome. But really, for folks like you who we know really well, what happens if we throw out the script and we just chop it up?

Ben: David Rosenthal Unplugged.

Jason: Literally MTV Unplugged.

David: Literally. We have no agenda, obviously.

Jason: But wait, where do you want to start?

Ben: We got to thank Vanta.

David: Oh, yes.

Jason: Oh, Vanta. I'm an investor.

David: We're investors too.

Jason: Well, great. They're an awesome company. Big supporter of podcasts. So yeah, go Vanta.

Ben: We are huge fans of Vanta and their approach to the whole compliance process—SOC 2, HIPAA, GDPR, and more. We've got CEO and co-founder Christina Cacioppo back with us today.

David: 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.

Christina: I'm really excited about this actually bit of not yet told Vanta history. But something like the antitrust reports honestly a much worse, much more poorly designed version by yours truly, which is why I can tell you that, were launched in the very early days of Vanta when we wanted to help companies get secure and prove that security, but weren't yet convinced we wanted to or had to go all through the nuances of what a SOC 2 was.

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. It should also help them be more secure because they've got this report, this security status page out in the wild.

In 2017, Vanta tried this and found out that no one really knew what a Vanta report was, and everyone wanted SOC 2. So flash forward to 2022, it's actually really exciting.

David: Turns out creating standards, people have to know who you are before you can create your own standard.

Christina: A little bit. Honestly, literally, I'm joking, but I'm not. Literally, the company's strategy on that day became okay, use the existing standards to bolster, sell, and build something better here. This launch of trust reports is really exciting. These are companies that maybe it's before they've gotten a Compliance Certification, maybe they're in the process of getting one.

For some, actually, they already have one, but then rather than keep going through their buyers process, they're like, look, this is just constantly up to date and has all the information you need, 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.

Ben: Our thanks to Vanta, the leader in automated security and compliance software. If you are looking to join Vanta's 2000, neigh, 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/acquired for a 10% discount.

David: Thank you, Vanta. So in the juicy stuff earlier you mentioned Mahalo. Is that where you started?

Ben: Can we just refer to the juicy stuff as—?

David: Is Mahalo why you started? You started from print to print.

Jason: Well, in the '90s, 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 got behind and the Fed showed up one day and this was maybe six weeks before I was set to go to college. He said, hey, son, I can't help you with college. Good luck. I might be going to jail so take care of your mom.

So he was like, really behind on his taxes and the State Authority takes it seriously. So Feds come, shotguns, the whole thing, they seize the place. They seize everything in it. I was like, wow, I guess I'm going to school at night. I'm going to work during the day and I worked fixing laser printers. That was like a really good racket. HP had just come out.

David: Were you set to go to college somewhere else?

Jason: 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. Then I said, you know what, I'm going to see if I can go to college and make that work. I'm going to Brooklyn College. So I decided to work during the day. Then I went to school four nights a week, 6:00 to 9:00 PM. I carried full credits, 16 credits a semester.

I would work fixing laser printers all day. I was a bad student. I was always that student who underperformed. I didn't find great meaning in academics. But I had a computer when I was in high school and I was more interested in playing with my 300 baud modem, which then became a 1200 baud modem on my PCjr.

Like many people of that era, we were 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. It was the game that came with it and Pong. So my dad bought this for us when I was six or seven years old in 1976–1977. He had one of the first Pongs in Brooklyn in his bar.

David: So he must have cleaned up on that.

Jason: Oh my God, it was crazy. I just got exposure to video games and computers. I was like, wow, this is incredible. Like computers are going to change everything. Then I happened to hack some software. We used to run a lot of scams.

David: You told us about the VHS.

Jason: VHS cases. Hot tapes was technically my first business but that was a side job I had which was cracking software. So we would make copies of Chess Master and stuff like that and then sell it for $10. Then we started hacking and doing what was called phone free games.

Ben: When you were doing this stuff, it's for you to be reasonably technical to do it. Not like Wozniak technical but like—

Jason: We soldered chips sometimes. To put memory in at that time, you had to take the memory chips, put them in, then bend them over, and stick them in.

Ben: Did you consciously ever make a fork where you were like not tech media, of course media about tech, but you're like, I'm not going to be that guy doing the boards. I'm going to be the guy writing about the people doing the boards.

Jason: It's a very good question. I used to go to Bleecker Street. I used to hang out in the West Village or the East Village. It was like a cool place to hang out. A thing to do would be to go to Tower Records and look at the zine section. 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.

Ben: It's like blogs before blogs.

Jason: Blogs before blogs, and I created a zine. I was like, I'm going to be a magazine publisher. So the first one I did was Cyber Surfer, which was about dial up services and CD ROMs. I did it with my friend, Brian Alvey, who you might have heard of in my career. We went to high school together.

David: With Weblogs.

Jason: We did Weblogs together. Yeah, but in the early '90s, I did Cyber Surfer.

Ben: Which is Engadget, [...].

Jason: All that stuff, yeah.

Ben: Which everything you sold to AOL.

Jason: They got sold to AOL. But anyway, before that, I did that magazine. Then I met Jerry Colonna at Internet World, the first one. There was a booth.

Ben: That's right. When Jerry was a VC before he was the whisperer of [...].

Jason: Before he was a VC, he was [...] for Lycos and I think CMGI. So there was a Lycos booth, and I had met this young lady at it, we hit it off, and we're talking. Then she introduced me to Jerry Colonna. I met Jerry Colonna in an office no bigger than this room in Union Square and he said, listen, I'm leaving Lycos, but I'm going to start this hack me ventures with my friend Fred. I want you to come read business plans for us. So I met Fred Wilson and I would go up to them and JP Morgan was going to back them for their venture firms. This was 1994–1995.

David: This became Flatiron.

Jason: It became Flatiron.

Ben: JP Morgan was the first big anchor of Flatiron?

Jason: They were half of it and Masayoshi Son's. SoftBank was the other half.

Ben: No way.

David: They wanted you to come be a VC associate?

Jason: Not a VC. Just to read business plans. So the deal was they would take me for sushi and pay me $1000.

Ben: Wait, what do VCs do besides just read business plans?

Jason: Exactly. I had the magazine started, Silicon Alley Reporter, and they were paying me. 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.

David: That's where Flatiron made all their money.

Jason: Yeah, they were going to invest anyway.

Ben: Flatiron became USV, right?

Jason: Yeah. Flatiron went with Jerry Colonna then when Jerry wanted to move to Colorado and just chill. He had made enough money I think.

Ben: Coach founders.

Jason: Coach founders. Yeah. I think he's been pretty public about it. I don't want to say a nervous breakdown, but maybe a fork in the road, like making a decision about what you want in your life situation.

David: Wrote a great book about him.

Jason: Yeah. So Jerry was a good mentor. But Fred actually became ultimately my deep mentor at that time. Fred said to me, listen, you're doing Silicon Alley Reporter. You're writing about us and the companies we're investing in, and you're doing stuff. Which would you rather do? I said, I think I'll do the magazine.

David: This was before. Now it's like…

Jason: Now it's like I do both. Why choose?

David: Just to back up to GeoCities, that sold to Yahoo for like—

Jason: Five billion.

David. Flatiron was the main investor.

Jason: Yeah. Flatiron maybe own 5 or 10% of it. It was like a huge win for them. I mean, Fred was on fire for a New York VC and Jerry, they did pretty well.

David: How did that happen, right? I mean, Silicon Valley was here. But they're in New York. What was going on?

Jason: There were a lot of good companies brewing in New York. My concept with Silicon Alley Reporter was, well, they have red herring outside in the bay, but I own New York and I had Silicon Alley Reporter. Then I started one called Digital Coast Reporter in LA. So I had two magazines, two conferences, two email newsletters. I was kind of the king in New York.

I grew that business to $10 million in revenue off my credit cards, and had 75–100 people working for me when I was 27 years old. I didn't know anything about how to run a magazine or how to run ad sales. I taught myself everything.

David: What would your family think of this?

Jason: It was pretty heavy 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 8000 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, finance, or art publishing. It was like a finite set.

I was in publishing, but I was also in this new thing, technology. So everybody wanted in on that. It would be like the equivalent of crypto is today like at its peak and you were the equivalent of Satoshi or something. It was crazy to be the New York internet guy.

Ben: So we talked about a lot of this when we did our big empire of Jason Calacanis episode with you. So I want to put this on pause.

Jason: Yeah, sure.

Ben: People can go listen to that. You should. It's great. We get the detailed story of Weblogs, Inc. and all that great stuff. Take us from you're only as good as your greatest, your newest thing. Because the last time we talked to you, you were just starting all in and can we talk podcasting?

Jason: Of course, I love it. Podcasting is, I think, perhaps my greatest medium.

Ben: What happened with All-In? I mean, has it surpassed your wildest expectations?

Jason: I thought it would be something Chamath and I would do 10 times. The origin story is pretty simple. Chamath I knew because he was running ICQ.

Ben: Chamath was running ICQ?

Jason: At AOL. I had sold my company to AOL. The revolving door at AOL. It was like Ted Leonsis had this march to a billion. My Greek brother and mentor had this march to a billion off site. So I went to this and I had just sold Weblogs, Inc.

Ben: But a million AOL users watch it.

Jason: That was the [...] with Weblogs, Inc. and with AOL and other assets they wanted to buy. They were going to march to a billion users. It was like this crazy rallying cry, and we had these T-shirts, march to a billion. So I go to that and I see Chamath. I was like, hey, and he's like, hey. We introduced each other, and we had known each other. I said, what are you doing here?

He's like, I'm running ICQ into the ground. I'm just riding it down every month that loses a million members. That's hilarious. He's like, yeah, but I'm leaving. I'm going to go. I'm going to go to the West Coast. I'm going to go work at this VC or whatever. All right, nice seeing you. So then when he was there, I was in LA.

Ben: What VC did go work?

David: Mayfield.

Jason: Mayfield for a year, then Sean Parker introduced him to Zuck and Zuck needed a Chamath. He needed somebody who would just [...]. He built the growth team. He was like, there is no equivalent of growth. The idea of growth hacking didn't exist as a term until Chamath did what he did. He said, just find me the smartest people. I'm hiring based on IQ. I'm hiring based on desire to make a lot of money and be a beast. He just went into beast mode because he too was very hungry.

David: You guys must have been like brothers from another mother.

Jason: Yeah, for sure. We're definitely both outsiders in Silicon Valley. I had Chamath come on the pod, This Week in Startups.

David: We listened to it. It's fun to go back.

Jason: It's hilarious to go back. You can see how he's not polished. He's not Chamath or whatever.

David: He didn't have the [...] on?

Jason: No [...].

Ben: Was he in great shape?

Jason: No. He was like a dork.

David: He's Bezos pretty...

Jason: He was like Bezos, pretty, yeah, whatever. He was always a poker player. He was playing Atlantic City. He was, like myself, an outsider who wanted to take risks and wanted to win—confident, even maybe more confident than both of us should be. I kind of introduced Chamath to the world by convincing him to come on the pod, which he was reluctant to do when he was on Facebook, but he did it after Facebook. So I kept asking him to come. Finally he was in LA, he came on the pod. Then people said he was really good on stage. He's funny, whatever.

Ben: Which at this point, you had an eye for.

Jason: Of course. I mean, one of the things when I was a podcaster in those early days, from 12 years ago, I introduced a lot of people to the world. Yeah, it was like 2008, I guess, whatever. So I introduced a lot of people who were in tech, and it was only a couple thousand people.

David: And then as now too, you could be a great founder, you could be a great person in tech, but that doesn't automatically make you a compelling podcaster.

Jason: No, of course not. I mean, I have my own theories about what makes for a great guest. We'll put that on the side for now. But anyway, we started a friendship. We started playing cards together. We started hanging out, trading notes kind of thing. He's going to start his venture firm. I'm a scout at Sequoia, all that stuff. We started planning and trading notes, and we just became great friends.

But then he was coming out of CNBC one day, and he's like, Oh my God, we have such a good rapport when you interviewed me because we had done a bunch of interviews with me on stage and stuff like that on my events. He's like, I want to do a podcast with you. Okay, come on This Week in Startups anytime. It's twice a week now.

Ben: Which is now five times a week?

Jason: Six. I may go back down to five next year. It's a little much right now.

David: We'll come back to this because you're killing yourself right now and you're on act three.

Jason: Yeah, I have more energy now. Just coming out of the pandemic, I might have as much energy as I did when I was in my 20s. But for different reasons, different type of energy. Anyway, Chamath calls me coming out of the studio. I don't know if he was in New York or he was in One Market in San Francisco here. He said, I want to make a new pod with you. Just me and you, we talk. I was like, sure. It's like, what should we call it? I was texting him back and I was like, we should call it All-In.

Ben: That was 2020?

Jason: Yeah, it's like two years ago, and I said, yeah, we should call it All-In. We should come with a poker name. He's like, yeah, great. A rage where someone's like all in.

Ben: Because you'd been referring to this poker game on air.

Jason: Yeah, I talk about it once in a while. The poker game that doesn't exist. Sky Dayton and I had a poker game with Brook Hammerling, the famous PR person at the Code Conference, which was the AllThingsD Conference before 20 years ago. Then Chamath had a poker game with Sacks. I had hosted at floating.

Putting all that together, I'd referred to it many times in the pod, but tried to keep it from becoming public. But it was me, Bill Gurley—it's all public now.

Ben: Marc Pincus, right?

Jason: Pincus used to come to the Code one. There's another funny story. Lots of funny stories in my life. But anyway, so then, the pandemic happens.

David: Where would you go in just dropping these little breadcrumbs here.

Jason: We got to pick them up.

David: We got to pick these up anyway.

Jason: At some point, I'll write a biography. Anyway, nine years, third book. Anyway, the pandemic starts to happen. Sacks has some ideas about masks, then Friedberg.

David: Sacks and Friedberg weren't—they were no besties originally.

Jason: No, no. 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 Sacks and Chamath. Now, Friedberg is the bestie. But he played in the game, obviously. We had just started to develop a friendship. But anyway, that foursome clicked pretty quickly.

I think I was a really good interviewer. I had studied interview techniques, and really after doing whatever, I'd done at least 1000 episodes of Twist at that point. I had had Sacks on many times, and Chamath, so I was very comfortable with that. At the poker game, we break chops and I make jokes. Chamath is a great host, and he's very comfortable with each other. Friedberg joined that group and it clicked. I thought maybe this would last 10–20 episodes, but during the pandemic, I think people wanted information.

Ben: In perspective, I think, that's the 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 going, that is a good point. That perspective is so helpful in our polarized world today.

Jason: Yeah. It's very unique. Around the poker table, we all listen to each other and we're friends, but the world does not want us to be friends. In some ways, the world wants us to be enemies. I think about it like the Best of Enemies situation. We debate specific things like Gore Vidal, and who was his adversary?

Anyway, there's a great documentary about Gore Vidal and William F. Buckley. They're just two public intellectuals. One was on the left, one was on the right. There's this documentary, Best of Enemies in the '60s. They started debating different political conventions. It was like the most compelling thing on TV.

David: But they were like friends.

Jason: Best of enemies. They weren't besties like Sacks and I are, but Gore Vidal, he was gay. 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. At one point Buckley, I think he called him like a sissy or something like really derogatory as a gay man and the world didn't understand. He was exactly gay. It was like time period in the '60s where maybe some adults understood like that's a gay man but we don't say that's a gay man.

David: When [...] got into town yesterday, we were driving by the Castros nearby and we saw a naked guy by the Castros.

Ben: Huge, jacked dude walking around and super sunny. So he's like, just all like butt lick down.

Jason: Does he have shoes on? Was he wearing combat boots?

David: I don't know.

Jason: They used to wear boots. Then they usually carry a sarong. There was a big debate when I first moved up here because there were a number of folks who used to like to go to Starbucks and they had to negotiate. They were like, how about a sarong Starbucks because you're going to sit bare assed.

David: For context, I've explained this to Ben, but this is a thing in the Castro in San Francisco. It's a cult. It's like a relic of the '60s–'70s.

Ben: I think it was pretty awesome because David was driving up and David goes, oh, a naked guy. It was the most warm hearted.

Jason: Yeah, I had to adjust as well as a New Yorker because as a New Yorker, if somebody's naked, that's a sign that there's about to be some crazy person, a fight, police, and chaos. Here, it means like high fives and ride ons. But growing up in New York, if somebody takes their clothes off on a public transportation or in a cafe, people are getting a baseball bat, calling the police, and like this shit's about to go down. Then here, it's like high five and live your life. That's one of the things I love about San Francisco. Anyway, the pod's gotten very big.

Ben: So you get the gang together and why do you think it works? You think it's like the number one-ish in tech or business podcasts?

Jason: In our business, it's number one, of course, but it was number 28 last week in the world.

David: You guys have transcended.

Jason: Yeah, it has nothing to do with finance or tech anymore. It has tipped over into colleges. I was skiing in Tahoe. I was with my kids. 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. No pressure, but are you going to be leaving soon? Because I'd love to camp out here and get your table. She looked at me and she goes, "JCal?"

I was like, have we met? And she's like, no. I listen to your pod twice a week. I'm like, it's only on Wednesdays. I listen to it twice. I was like, oh my God, that's so nice. I was like, are you in the industry? She's like, I'm a dentist in Reno. And I'm like, you're a dentist in Reno, may I ask how you found out about it? She's like, I don't know.

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

Jason: No. Somehow she had found it, and this is during the pandemic situation, and that's when I realized it had crossed over.

David: Was there a moment, either you for or you, where you were like, whoa, this is…?

Jason: I've been a micro famous, micro celebrity multiple times in my career.

David: But this is different.

Jason: Not for me, and I got a lot of famous friends. I'm used to getting recognized. I'm used to people taking pictures. What I'll say is like, where it used to be, if I go to Austin or New York, people would say, I would have three people stop me on the street a day. If I was walking around in New York. Now it's 20 or 10 and they want to take a selfie. You know how 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 then people become characters. In all honesty, I did craft with All-In. I was very premeditated in creating some character. I never really talked about it. I crafted some character arcs. The fights are all real. Trust me, there's nothing scripted about that. But I did say like, I think I can, as the point guard here, shape the conversation and literally created the character of the Sultan of Science. Friedberg didn't even have a Twitter handle.

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

Jason: JCal, the world's greatest moderator, sure.

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

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

David: You care about the environment.

Jason: Well, no, it's also like I don't want to waste a ton of money and whatever reason.

Ben: But you do let yourself play that role. You have been enormously successful. 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 make it.

Jason: I actually never wanted to play that, actually. That was not just the boys breaking my chops. Maybe it's a little bit like them wanting to take the piss out of me a little bit, which is fine because I give it as good as I can get it. But I think that's probably for them. You can ask them when they're on the pod. I think for them, that's the diss. That's the one they can easily go to is I'm the poorest guy on the show, but I'm doing okay.

David: Maybe let's flip it. For them, before All-In, Chamath had a little bit of a public presence.

Jason: They were not famous. This is a new thing for each of them to hit this level of notoriety. It's not for me.

David: I mean, we should ask them this, but if you were to speculate—caveat that it's speculation—what do you think for them All-In has done?

Jason: Well, I mean, for Friedberg, nobody knew who he was except if you worked at Google or you were in VC. He is very connected in those circles.

Ben: Or Monsanto.

Jason: Or Monsanto. He's very connected in those circles, but he was an under the radar guy. I think, really, by design, he didn't have any desire to. I think it's probably the biggest adjustment for him. The increase in profile has certainly been the highest for him. He's loved. There was a moment when I jokingly said to people during the Q&A session in All-In Summit, just say who your favorite bestie is and then direct the question. It was like five in a row, Sultan of Science.

Oh my God, what have I done now? I've created this monster. At the time, he would barely show up. He would show up for two out of three episodes. He'd be busy. It wasn't a priority for him. I'd be like, all right, I'll put Brad Kirschner if you can't make it. I'll try to get Bill Gurley to show up or Draymond to fill in for him. It was always like, I wonder if Friedberg would show up. But he's actually really committed to the show now.

For Sacks, he was high profile, but nobody really knew him as a Republican. He unclothed as a Republican on the show.

David: Well, I feel like he was almost even more so than any of you, but he was high profile. If you knew about the PayPal Mafia money. But he was like the least public of the PayPal Mafia crew.

Ben: For PayPal Mafia, you would say, Elon, Reid Hoffman, Peter Thiel, Max Levchin, Jeremy Stoppelman, Chad Hurley, Roelof. I guess Sacks would be somewhere in that shrauta of being known. But not success, being known.

David: Being known, yeah.

Jason: I think part of the reason this works with Sacks, I think Sacks has probably taken the brunt of the hit of the pod because he is so passionate about a lot of topics that maybe are unpopular in the tech circles. I do think it's caused him deal flow on the margins, probably.

Ben: Really, margin?

Jason: I wonder. He said that jokingly on the show. I don't know. I'm just thinking, maybe there's—

Ben: Craft has ascended because he's done All-In.

Jason: Yeah, sure. I'm trying to think. I wonder, I don't know this. But is there a founder who is a young founder who would say I would never take money from Peter Thiel's venture firm because I'm so liberal?

Ben: For sure there are.

Jason: Okay.

Ben: Those people feel that way about Craft now, but for every one of those there's ten more who know about Craft now.

Jason: I would agree with that. So anyway, I do think he's joked that it's caused him deal flow. I don't know if it has.

David: The pod too, for people in America and people in tech, has moved a lot of people towards the center.

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

Ben: It's insane to me that that was the same Pataki.

David: Were you [...] or were you still in New York?

Jason: I wasn't, but I would have voted for him. I like competent people. I supported Bloomberg for President, which got me a lot of flack. I don't understand why. People were very upset that I was for him instead of whoever.

David: I think you guys talked about this on the pod. What was the 2x2 quadrant of whatever it was. 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.

Jason: Yes, it is a small group. I think I believe in competence and staying out of people's lives. It's very hard to know because then even David. 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. Certainly the MAGA group has no love loss for JCal, I can tell you that. My replies have been really crazy. We get brigaded the last couple of weeks. It's nuts.

It's funny, but it's also on the margins, they can get a little scary. They'll dox sometimes and that's not fun. A handful of times it happened. But, I had to tell David, I don't actually listen to MSNBC and Rachel Maddow to get my information. By the way, you're pro-choice, pro-gay marriage, anti-war.

David: Yeah, he's the dove.

Jason: I was like, well, okay, if you were going to play this game on, I'll dub you David the dove, and now you're making me into Jason the hawk. What are we talking about here?

Ben: It just goes to show how silly the coalition building is.

Jason: It's totally silly.

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

Jason: It's so crazy. I think what messes people up is the fact that I actually just think Donald Trump is a horrible human who you should do no business with, has no business being in any political office, and is just horrible on any number of levels. But I believe that independent of his party, he's a Democrat, obviously.

David: Obviously.

Jason: Yeah. I would hate him as a Democrat or a Republican, so it's not personal.

David: Or it is personal with him, but it's not personal with the party.

Jason: It's very personal with him. I just think he's just a horrible human being in every way. Now, I understand for some people he represents change. For some people, it's like the way the Republicans secured office, and that's all they care about is winning. I get it, whatever.

Ben: I think so much of the human condition is like being a part of a community. He, for so many people, is a symbol, that means hey, all my friends and neighbors, we get to agree on something so that we all can find togetherness in something. For some people, that's the flat earth and for other people, that's startups. For some people, it's the tribe.

Jason: Yeah. A lot of people don't practice religion anymore. He's their religion, Hillary Clinton, Elizabeth Warren, or Bernie Sanders might be other religions.

Ben: Or the new iPhone. I found myself ordering this phone and I love it. It's the iPhone 14 Pro, it's magic, and whatever. But it's not that different from my old phone. But I got to participate in all the fun, watching the keynote, the tweeting and the nerding out. I'm like, let me look at the image quality versus the old one.

David: It really is pretty.

Ben: It is pretty, but I got to be part of a tribe. That is a thing that no matter what your tribe is, that is so fun to be there on tribe day and tribe week.

Jason: I will say the thing I'm proud about the show, I think, is that through a lot of the trials and tribulations shown, you can be friends, disagree, learn from each other, and have a vibrant debate, which is how we all grew up. When I say we, including you guys, but also especially the besties. I want to be friends with people who I disagree with. I want to debate stuff.

Like this guy Dean Preston, he's like one of the supervisors here. Super idiot guy in San Francisco. Let them build housing and stuff. He's like, you're just a conservative, blah, blah, blah. I was like, you don't actually understand who I am. He's like, you're a conservative billionaire. I'm like, you're wrong on both accounts. [...] the latter.

David: My besties remind me of the latter.

Jason: I'm miling on it. I'm not trying to be a billionaire, thank you.

David: Another thing that's really fascinating to me about All-In and you guys is before All-In—and still to a large extent—Silicon Valley has this weird relationship with money, like a super weird relationship with money. Remember there's a whole thing about Zuck drove an Acura SUV.

Jason: That all came from David Filo and Jerry Yang were driving their old cars to work.

David: You could make money, build a company... You guys are like the first, whatever, we got a private. That's fine.

Jason: I mean, listen. I believe in capitalism. I think it's great if people create jobs and if they get rewards for doing so. Fine. Literally, The second book I'm writing right now is about wealth and money. But not in my regard, but in a big picture societal regard. So I'm literally been thinking about this topic a ton. I think we worry a little bit too much about wealth creation with a small outlier wealth creation.

We don't think enough about inspiring people to create companies and learn. The time I create the most controversy is when I believe anybody can do it. People are like, you're so wrong. I'm like, am I? Because I go on YouTube. You could type in any topic that you want to learn and you can learn it. All the stuff that was at MIT where I never got to go, Stanford, and Brown is online for free.

I listened to macro economic classes and AI classes. When it's 10:00 PM and I'm doing my email, I'll just put one of those playlists on from MIT OpenCourseWare. I'm like, I can't believe I can take a course at MIT for free anytime I want.

David: Then you flip it, you can build a business there. David Senra with the Founders podcast, Mr. Beast, MKBHD. Nobody gave these guys permission.

Jason: The world has never been this equitable. But people want to spread a narrative that the world is unfair. I watched why the world becomes so fair, so just, and so much information and opportunity become available that I'm like, wait a second, I could never figure out how a term sheet worked. Nobody would share their term sheet. Now there are a thousand videos and blog posts on how to negotiate your term sheet.

Ben: The world is still unfair. I think the key insight is to recognize that the world is unfair. Actually what that is, is a game on the field and figure out how to play the game on the field.

Jason: Sure. But I mean, it's never been more fair. The world is unfair, true statement. And in America, it's never been more fair. Google has 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.

The average job entry salary for these things is like $80,000. I find this 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 good.

Ben: That's their community. That's how they find that there are other people who love that they tweet that the world is unfair.

Jason: And it typically is like a certain type of person, I'll just leave it at that. 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. I'm going to actually teach it myself this next cohort where I just teach people how to start companies.

Ben: All right, let's plug it. How can they find out?

Jason: Founder.university. That's it.

Ben: And that's very good.

Jason: Yeah. I mean, basically it's free. The way I did it was you apply, if you want to build a company, you pay $700. If you go and you get to week 12, we charge your Stripe back, the card back the $700. If you don't come or if you don't have an excused absence, if people miss something because of their kids or whatever, fine. But we just try to get people to complete it. Over 90% of people complete it.

Ben: That's cool.

Jason: And then we're investing $25,000 in some of those folks to help them start their companies. People don't know all the work I'm doing quietly, but 200 people go to this course now. Or maybe about 400 in the fourth cohort, we'll see. But people can learn how to create companies. They're like, no, they can't and I'm like, yes they can. You will have to have gone to Stanford. I'm like, no, I'm invested in 350 companies, maybe 5% of the founders went to Stanford.

No, that's just not. It's patently false. You have some confirmation bias. You're dealing with a data set from 10, 20 years ago. I get it. But I'm telling you, on the streets, ground level truth, we all meet with founders all day. It's never been more diverse. It's never been more open. Nobody cares where you went to school.

David: Nobody cares where you live anymore.

Jason: Nobody cares where you live. They care about what you've built and your traction. 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 as beautiful of a meritocracy as I've ever seen and you say the M word, it freaks people the fuck out. I'm like, why is it so scary for you that Silicon Valley is a meritocracy? And no, because it's not. I'm like, it kind of is.

Ben: Can I answer your question earlier of why I think All-In works?

Jason:Yes, go ahead.

Ben: All right. Thank you. You've got the perfect storm of three things. The first thing is billionaire Warren. You're counter positioned. Most people who attain that level of wealth crawl into a quiet hole and make sure no one knows.

David: You're doing shows from boats and jets.

Jason: I've never done it from a jet. But yeah, there were definitely two boats in the last two years. That's true.

Ben: In some peak moments of All-In, it's like watching billions in real life. It's like you hear Chamath talk about this spread trade and you're like, this guy's got a lot of money on that spread trade. Does he actually have a key insight here? There's this interesting intrigue there. So bucket one is like billionaire porn.

Bucket two is by the research you guys do and the folks that you each work with, because there are definitely researchers that seem to be involved, you bring things to the table that are brand new insights that aren't widely available yet. I feel like I was learning things about COVID-19 on All-In that I wasn't getting through any other source. Somehow this is not making it to me. This feels very, a lot of it proved out to be like this was good information before it was masked.

Jason: All four of us are information junkies with a lot of research and teams.

David: How many people touch an episode of All-In?

Jason: One. Producer Nick, that's it.

David: I mean a bit like the research stuff like that.

Ben: There are text files open on people's computers when they're talking.

Jason: We have a docket with the notes, but that's mainly for me to queue it up. I just read the four or five bullet points so people know it. I do that with my team, the docket, but the docket is built from the five or six stories that people submit to our group chat and say, hey, put this on the docket. I think Sacks has some research help. Friedberg and Chamath read the stories or they're well read. All of us read constantly.

We're in the information business of talking to people about the world. So you guys are investors, you know how it is. You do 20 meetings a week with founders, they're going to tell you everything about the world. You guys are still young. But imagine you do that for 20 years, you're going to get smarter. You're a journalist for 20 years, you get pretty—I wouldn't say smart, but you'll be informed.

Ben: If you're hearing the right pitches, you actually are getting cutting edge information before it's widely available.

Jason: Definitely. So okay, that's number two. Yeah, we probably have a slight information edge. I will say the information edge compared to journalists—this is not a dig to my journalist friends. I was a journalist. I had 75 people at the magazine. We were always trying to figure out from the principles what was going on and tell that story. But we were only as good as our access to information. Now looking back on it, I think we had between 5 and 35% of the story. I know that's probably triggering to a lot of journalists that they have that little information.

David: You weren't on the inside.

Jason: But you weren't on the inside. So when you're on the inside, you have 100% or even on the inside, you might only have 50% depending.

Ben: You get enough to run with and you feel like okay, now there's enough story here. Let's do it. That's clearly not the whole story, but it's enough to put the piece together.

Jason: And then over time, process journalism, as some people have dubbed it, maybe the six or seven stories will tell the full story. Which is the third component that makes it successful?

Ben: It's the thing that David and I took forever to realize works about Acquired which is relationship and charisma. People like having fun by listening to stuff. If we can make history fun, then people are going to listen to four hours of us diving into stuff you would never read in a book. You guys do that in spades. It's just so fun to temporarily join your world.

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

David: Listen every week. Don't miss it. Literally walking the baby up and down the hills listening to it.

Jason: People tell me they listen to it twice and they take notes. I'm like wow, that's great. I was very intentional with my role in it to step back and be like the point guard. 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.

David: How did the Friedberg host episode come about? One week you switched roles.

Jason: Well, he was like, I think this can be done better. This could be better. I was like, go ahead. Sure, I'll just shoot.

David: You pass the rock.

Jason: He did a solid job. But let's be honest.

Ben: He's not a point guard.

Jason: It's not showtime, that's for sure. I don't think people are going to go to watch him play point guard. I mean, he did a serviceable job.

Ben: Put that on his tombstone.

Jason: No, but he shines when I created a science quarter for him to shine. Bring me a sign. He's like, I don't know if I want to talk about politics. Listen, Sacks wants to talk about coronavirus politics. I'm giving him his red meat. Here's your quinoa. Come to me with the science story now and we'll do this quinoa corner thing. I've made him the Sultan of Science.

It was a distinct effort. I really wanted to make him shine, and it worked. It worked because you see how engaged he is. What used to happen was, and fans notice—I'm not speaking at a school here, you see it every episode—Sacks would disengage during science and quinoa. Friedberg would disengage during politics. 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.

Ben: That's a hard job.

Jason: 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? My interruptions—I call them interjections—do they help? I actually looked at the interjections. If you look at McLaughlin—you guys did not grow up with Mclaughlin.

Ben: Super unfamiliar.

Jason: So The McLaughlin Group was the best Sunday morning show. It was so good like SNL would parody McLaughlin. It probably had a million people watching it because Scott McLaughlin was pretty cantankerous. If he didn't like what people would say, he'd be like, wrong. This is the answer. 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. I may have pushed 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.

Some people in the audience are like, you have to be the fact checker for Sacks. I'm like, no, that's not my job. I'm not real time fact checking Sacks. That is a delicate balance. Then sometimes I'll ask questions, specifically because I know the audience doesn't know what fair market value and the [...] acronym means. So I'm like, explain that. I'll stop somebody.

Ben: I mean, you're expanding the TAM to dentists.

Jason: Correct. Thank you. People are like, oh, JCal's an idiot. He doesn't know that term. Or I say to somebody, can you unpack that? Can you explain that?

David: Obviously, you know that term. You were the third or fourth investor in Uber.

Jason: Yeah, exactly. Well played.

Ben: I think he's been at Robinhood too.

Jason: I'm like, dude. I'm asking that question on behalf of the audience. When I'm moderating, as opposed to being an interviewer or as opposed to when I'm working with Molly and we're chopping up the news, when I am the shooter, and she's maybe playing point guard a little bit. I'm shooting, then sometimes I'll pass it to her, and she shoots. I can travel between those roles and in that role, I'm acting on behalf of the audience.

I get the sense like, Chamath's going too much. 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? He's like, almost. That's what I think has brought in, to your point, a lot of the dentist growth.

Ben: Having an intimate sense of where your audience's edges are, is a really important role there.

Jason: It's an art.

Ben: When we have guests on, I'm always trying to catch where they just go slightly too deep, and I need to pull them up.

Jason: Podcasting is about going deep. It is really an art. Do you want to stop somebody when they're going down this crazy rabbit hole? They're going down some rabbit hole that has never existed in the media before.

Ben: You want to let them go, but you need to make sure they're taking the stairs. Because if they just jump in, you're like, oh God, no one has any context. They can't learn anything new because you're like, you're not contributing it to something they understand.

Jason: They just jumped into brain surgery. Let's just explain to us. How are we going to chop up this brain? It's a bit of an art. But I have to say, it's been a different muscle for me to flex and it's been great fun for me.

Ben: The other thing—I don't know if you think about it on this axis at all, but I used to think it was very binary. Like there are two categories of podcasts. There's candy and there's vegetables. I listen to the audio version of Stratechery, and that's my vegetables. It's enjoyable intellectually, but it's not fun. I certainly can't be doing anything else with the language center in my brain while I'm listening to that. I have to be on a run. Sometimes even at home so I can take some notes or look something up. I can be cleaning.

Jason: It's a pause-type podcast. Sometimes you're hitting rewind. Let me make sure I get what he's saying here.

Ben: Or I can listen to the talk show with John Gruber and it's just like, if I missed out on 20 minutes because I was brushing my teeth, then I left the room and I came back and I'm like, oh, I didn't actually miss anything. It's comforting. It's like I love all the stuff he's talking about, but it's not a must listen every time, every minute, every second concept, and I'm not using hard parts of my brain to understand.

David: All-In has become candy and vegetables.

Ben: It's both.

Jason: Yeah, for sure. I tried to do with This Week in Startups and All-In. I try to have it be both a little bit of personality, a little bit of entertainment. Some fun hot takes.

David: Related but separate topic. Silicon Valley. Part of the origins of All-In, there's a lot of bashing on San Francisco politics going on. There's a lot of crap wrong here, but you guys are all still here. How are you guys feeling about it? How do you feel about that? What do you think of the Bay Area?

Jason: I lived in New York, Brooklyn and Manhattan. Then I lived in LA. Then I lived here. I think I'm moving to places I enjoy less and less each time. I enjoyed Brooklyn and Manhattan much more than LA. I enjoyed LA much more than San Francisco. I don't know where to go next, but I'm going to go somewhere.

David: Why are you still here then? There's no reason for you to be, is there?

Jason: I came up here because I have a lot of friends up here. I had done LA. I was like, I'd been a Sequoia scout. Then I was like, my friends are telling me I can start a venture fund. You need to be up there. I wonder how I would do if I was up there in the industry.

Ben: Because if you wouldn't, you'd always wonder.

Jason: Michael Moritz used to call me the mouth from the south. Because I had two investments in LA. Oh, the mouth from the south is here.

David: I can just imagine Michael saying that.

Jason: But I moved up here and I love it up here. It's quite bucolic. My kids are loving it. It's quite nice. I would love to live in another city in my life or two. I could see myself in Austin or Miami. I like both of those cities. I think Austin's the future. California is going to be damaged for a decade or two. So I think for the rest of our adult lives—

David: Because of the pandemic?

Jason: I think the politics, regulation, and not appreciating the tech industry is really a problem. Then you look at this guy, Dean Preston, he is dunking on the founder of Away and Stewart Butterfield from Slack. They're a couple. He's like, we got a $1.2 million out of them when they sold their homes. I'm like, and you also lost to incredible founders who have created tens of billions of dollars of wealth for San Francisco, you idiot.

At the same time, Francis Suarez in Miami is listing all of the venture capital and doing a tweet storm about all the companies that raise venture capital. So you have one guy, Dean Preston, dunking on people saying, we have this 1% so when they sold their $30 million house, we were able to extract $1.2 million. That's why tech doesn't like me. I was like, hey, dummy.

David: Yeah, now that all the future earnings are gone. Your marginal tax rate is 13.3%.

Jason: But they just have an exit tax now for homes in San Francisco. So if your home costs over $10 million when you sell it, I think it's just sales tax.

David: $1.2 million from them selling their home versus 13% of their future earnings stream—

Jason: Literally, the chef at Slack paid $1.2 billion in taxes from their RSUs. Where do you think? The $1.2 million chef probably paid in taxes on their RSUs at Slack. You absolute moron. You're literally so upset about their mansion 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. You could change the tax code. It's fine. Raise the minimum wage like Bernie Sanders and Elizabeth Warren attacking Bezos endlessly. Then Amazon starts paying $22 an hour, gives you benefits, and pays for your college.

It's like, okay, hold on a second. I know what Bezos just did. He took the platform that you could never actually enact and he enacted it inside of Amazon. If it's not perfectly clear what just happened, literally, he's dunking on you. You wanted free college and couldn't get it done. He gave it to Amazon employees. You wanted a $15 minimum wage, he made it $22. 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 for them.

David: Maybe you could argue that them pushing him and pushed it.

Jason: No, no. Definitely it is literally him showing as the Amazon cruise showing let the free markets work like the DoorDash, Uber, Amazon, Starbucks absolute race and battle to just hire entry level employees and make it delightful for them and a lack of immigration is what has driven these salaries and the benefits up. It's extraordinary what's happened with the free market. Minimum wage is still $7. Federal minimum wage is $7 and change, and $15 here in the city and New York is $15. That's weird.

Ben: 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. They basically never offer currency visibility.

David: Totally. Brex was one of the first corporate cards.

Ben: No, the first new, innovative.

David: First new, innovative credit 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. It makes so much sense for it to all be together.

Ben: The data being integrated lets them do really great stuff. You want your employees to be compliant so it ensures 100% compliance. But also, you need it to be easy for them so you can do cool stuff like have managers set budgets. 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.

David: No receipt chasing, no approvals. No, it's all just done and all integrated.

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

David: Yeah. Globally, how many companies these days, even startups, employ people globally who do not just need to be paid, but then are spending, buying things, going to dinners, et cetera around the world? You need something that operates globally. It's awesome.

Ben: Plus, the remote work thing is here to stay. They shared the stat with us. More than half of the startups in the last YC batch are from outside the US. Then there was another one. Accenture said that workforce models with productivity anywhere are now used by 63% of growth companies. Remote is not going away. So you really do need to figure this out for people who live everywhere.

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

Ben: Yup. If you have global enterprise ambitions, Brex is the answer. Of course, they have a great mobile app. They were like one of the first corporate card programs to have a delightful mobile app. Now that they're serving large growing customers around the world, they can do everything from that mobile app too.

David: Indeed. If you want to learn more about Brex cards, spend management, and why both of those together are loved by teams all over the world, go visit brex.com/acquired or click the link in the show notes.

Ben: Thanks, Brex.

David: We referenced this at the start of our conversation. You're working as hard or harder than you ever have.

Jason: Smarter.

David: You said you've got a new well of energy.

Jason: Yes.

David: Tell us about it.

Jason: Well, I find great purpose in what I do. When my friend, Tony Hsieh, died, I really thought deeply about what I wanted to get out of the rest of my life. I realized these are the things I really love doing and these things maybe not so much. I just realigned my life over the last few years.

David: What are the two buckets?

Jason: Yeah. Exactly. I can tell you things that are just to me I'm not going to get pleasure about in life. Working, no offense to my incredible lawyers, but negotiating term sheets, legal and HR issues, accounting, operations, and tax, that entire stack of things is not fun to me. Not fun at all.

Ben: I'm sure you never viewed that as fun, but at least before you were like I'm willing to put up with it because maybe it's a thing that creates enough value for me to do it.

Jason: Doing my podcast everyday, an absolute joy. Entertaining an audience, thinking about the world, and having these conversations. I had Toby from Shopify today. I leave the Toby interview, it's like his third or fourth time on the podcast. Instead of us having dinner or lunch, we just record a podcast. The end.

Ben: In person or did he?

Jason: No, we just hopped on Zoom. It started because he did that tweet about his compensation tool where here's your total comps, you can move the slider. I was like that's brilliant. Come on the show. You want to go on the show and talk about it? He said yeah, of course.

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? I watched Howard Stern when I was a kid or Charlie Rose do it day in and day out and I was like I could be like those guys. They get on there every day and seem to love it and I do. I just committed to doing it every day and I love it.

Ben: Isn't it weird when there's something that takes a ton of work but somehow doesn't drain you?

Jason: 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. Then I recruited Molly. I was like, I need somebody to do this with me every day who I respect, who's awesome, and brings something to the table that I don't have and having,

David: She's so great.

Ben: Having someone to play off of, I feel like that's the thing that's kept Acquired going.

David: I don't know how you did it alone for a decade.

Jason: I'd have guests on. It was largely a guest-driven show and then I would do the news round table once a week because it was once a week, then twice a week, then three times a week. Then I was like how many [...] are out, I'll do it five or six days a week.

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

David: Have you exercised?

Jason: Well, I created a platform, Founder University, where if you want to build something, I will talk to 200 people that you can build. Then whatever rises as the performance and the product and as people move from talkers to the walkers, when they actually start building stuff, that's when I get great joy. Bring me the people who have product velocity.

People don't understand the scale of the business. Nobody really understands what I'm doing and I kind of like it that way. The angel syndicate is now the largest syndicate in the world. I've deployed $185 million in my career as an angel investor doing $50 million a year now.

David: That's awesome.

Jason: I'm raising the fourth fund in public, 11,000 angels in the syndicate. This is going at a really significant velocity. If you were to look at the slope, it's not quite a hockey stick, but it's hockey stick-esque in terms of the total capital I've deployed and it's in really high quality companies. I'm getting better at it. There are 11. I have 22 people, 10 on the media side and 12 on the investment side.

On the investment team, people don't understand. They're like you're a solo GP. I'm like yeah, with 12 people. Those people are doing 60 introductory meetings per week. Then we're doing maybe 15 or 20 second meetings. It'll be a hundred meetings a week shortly, probably.

Ben: Across 10 people or 12 people.

David: But you're not doing them?

Jason: I'm not doing them.

David: You had this line. It was on Twist, I think?

Jason: Not for me.

David: People say that's a lot of work, but you're like yeah, but not for me.

Jason: That is the new philosophy. This is why my energy is really high. I have told everybody who comes to work for me, I work 60–70 hours a week, keep up. If you can't keep up, don't be here. I'm looking for a fixed 50, a solid 60 hours a week. You don't have to match me 60 or 70 hours a week, but keep up.

Ben: In that team, are you looking for the next Jason Calacanis to be part of that team, or is it like someone who likes doing that part? Let me ask it more directly. Is it someone who's content with doing this, or are you looking for people that are hungry enough to be the next Jason?

Jason: I'm open to all of it. They don't need to want to have my absurd unhealthy desire in my youth to be successful. If they did, they probably wouldn't come to work for me, but maybe they would. Actually, I would. So yeah, they probably would.

David: Not for very long though.

Jason: Yeah, five or two. People come and they work for two, three, or four years and they go start their own venture fund. Mazel tov, that's great. What I told them was just find great companies. I looked at investment team meetings, usually they're Monday. People do it for an hour or two and then they go to lunch.

I said I want to do it twice a week, Tuesday and Thursdays, 2:00 PM to 4:00 PM. Hit me with companies. That was another innovation I did. 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. This is like one of my lifelong best friends. I said run the company. Here's what I want to do: the podcast, meet with the founders, and do the LP fundraising. That's it. Teach a course.

Ben: Are you enjoying the LP fundraising?

Jason: I am now. I'm kind of like Axe, I don't know if you watch Billions?

Ben: Yeah, every episode. It's so great.

Jason: You know at some point, he was like I'm going to raise money.

Ben: It's cap raise time.

Jason: It's cap raise time, and Wags. I got my Wags. Mike Savino is my Wags. I got my Wags who just fixes everything, and I'm like I'm going to go raise money. We're doing 506(c).

David: You were in 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.

Jason: We'll see. I've had select institutions make small bets. The first one was $10 million, the next one was $11 million, and then the last one was $44 million. The first fund I deployed in five years. Second fund, two years. The third fund, two and a half.

David: Five years, wow.

Jason: That was my first fund. It was me, Bill Gurley, Dave Goldberg, rest in peace, Tony Hseih, rest in peace. David Sacks, Chamath, just a bunch of my friends put money in. It was to see if I wanted to be a venture capitalist and do this as a career. I was like, yeah, I just did it over five years.

The second one, I raised $11 million. It took me six months to a year to raise the first. The second one took three to six months. The third one took me three months to six months. In this one, I think I'll wind up raising in the first 10 days what I raised in the first couple of funds. I literally did like two webinars. A couple hundred people came to each.

For people who are listening, 506(c) is something you can raise in public, which means you just can tell people I'm raising a fund. I was like, I'm doing All-In. It doesn't make any money. I have This Week in Startups, and I watched a bunch of these young aspiring VCs raise publicly. You didn't raise publicly?

David: No.

Jason: You did it privately.

David: I've thought about it, but for a whole bunch of reasons.

Jason: It's kind of scary because people don't do it, but if you have no track record and you want to raise, like this guy [...] the VC.

David: You did a great episode with him.

Jason: Yeah, it was great. I had him on first time founders for a season of Angel, which is a subsection of This Week in Startups podcast and I became an LP in his fund and he just saw me. I did like hundreds of meetings, I did five meetings a day for a year. I raised $10 million.

He's African American and he's just like it's just a matter of how hard do you want to work. I'm like, be careful saying that publicly because there's a group of people who do not want you saying that. He's like, no, all you have to do is you go to AngelList, just set it up, and then you just start talking to other VCs. You talk to them and you just have to be willing to take 50 meetings a week. I'm like dude, do not say that it's easy to raise a venture fund as a black man in Silicon Valley. It's not that it's easy, but that it's possible.

David: On the internet too, you find people who believe that too, and then they believe in you and then they back you.

Jason: Correct, the whole thing. What I noted when I was taking my notes watching him was so many times people were like when's your next fund? I'm like three years. They're like oh, let me know. I'm like okay.

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

Jason: Three years from now. I mentioned it on All-In, I tweeted it, and all of a sudden I had a thousand people sign up for it.

David: Is there a limit to the number of LPs you can have in 506(c)?

Jason: Of course, 250 accredited up to $10 million and then 2000 QPs. It's a lot more work.

Ben: QPs are?

David: Not for you.

Jason: Not for me. Qualified purchasers.

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

Jason: I think it's $5 million investable assets and then accredited now is $200,000 if you're an individual for the last two year and $300,000 if you are a couple and you have two years in income, or a million dollars in net worth outside of your primary residence.

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. I think that's coming in the coming years. Just like I democratized, angel investing, wrote the book Angel, was the first syndicate on AngelList, the most successful syndicate on AngelList, created my own, got the domain name the syndicate, created the largest one, and have done 265 syndicate deals by far the largest amount of anybody, I think.

David: Now as a participant of a fund on AngelList, those are big numbers.

Jason: You do something consistently.

David: You've done four SPVs on AngelList and we have the fund too, but that's a lot.

Jason: You're hurting cats. You need to have a lot of people. Putting all that together, I think now's the time to democratize venture capital. That's what I'm attempting to do here. I want more people who are accrediting qualified purchases who've never been in a venture fund to look at the asset class and just consider it. It's high risk. It's a high reward. I'm in 20 venture funds myself, including yours.

David: Thank you.

Ben: But don't pitch Jason.

Jason: I'm sure I'm going to do yours. I'm just going to pick them based on people I know or people I know online or people on the pod. I'll do one or two new ones a year.

David: This is kind of like the conversation earlier, like on the internet, this is the democratizing thing. Nobody's going to just invest in your fund, but if you go do stuff, and then people are like oh, Jason does stuff. Great, I'm going to back Jason.

Jason: Be of action. It doesn't mean you have to start a podcast. You could be a blog, you could do whatever. You could create a founder university, whatever it is. You can do any of those things. You could have a track where you could be an advisor to startups, whatever it is.

Ben: I'm curious, as someone that's always raised from sort of individuals, do you like the idea of having some institution be like can we invest $15 million?

Jason: Yeah, of course. I've had $5 million checks, $10 million checks in the fund from fund to funds and institutions. I would very much, at some point—I don't need it, but it would be meaningful for me, both my parents are cancer survivors, to have Memorial Sloan Kettering endowment.

David: UCSF or something like that.

Jason: Somebody like that, if they wanted, I would work really hard to try to get them a great return. I would find even more meaning in what I do. I got that from Sequoia. They would have this Sequoia dinner every year for the founders and they would say here are what the foundations, who are LPs, are doing with the money you made for them with your companies. Yo go click, click. Here's what before the foundation is doing, here's what this foundation is doing.

David: Their conference rooms are named after their LPs, right?

Jason: Their conference rooms are [...].

Ben: This is real. I find we have state pension funds and stuff like that in PSL ventures. You take it much more seriously because it's not just about the reward. I'm like, I'm so excited for what we're going to do for them. This is really important to preserve this capital. The psychology of doing that while you're taking big swings with asymmetric upside, that I find to be a fascinating dance.

Jason: That was like one of the seasons of Billions where he's like, I'm going to be a family office. No, I'm going to raise my own fund. There's this natural tension for Axe of what should it be? He decided I like when I have other people's money because he seemed to perceive.

Ben: I think he felt that he wasn't as somebody in his ecosystem, in his community, without maybe managing outside capital.

Jason: Maybe. I think it's like playing in the bubble with nobody in the stands versus getting on the court at Madison Square Garden and there's people in the stands.

Ben: Your numbers don't mean anything unless you're putting them up for—

Jason: I'm doing this quasi public. People still have to sign up to come to a webinar, but I'm sharing with them like here's the totality of my investments, here's what I've done, and here's what I plan on doing with my team. I'm kind of enjoying it. I've met with all the top endowments in the world over the years, and they're very kind to me, but it's always been like solo GP is a blocker, no track record.

David: Your fund is so small. We're a $50 billion endowment.

Jason: At some point, one of the ones who's the most rigorous, I wouldn't say exactly which one was like, we have a lot of respect for you. We know who you are. People would like you to sign a book and take a selfie with you when you're here, but I just want to be straight with you. We don't add many funds. And if you go through our process, it's going to take a lot of your time and it's going to result in you not getting our money this time.

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

David: Was that in the last fund cycle?

Jason: That was in the third fund cycle. 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. 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.

Ben: Are there any downsides to doing the raising in public other than?

Jason: Not that I can see. I guess you could fail in public, fail to raise the fund.

David: That doesn't seem like something you're scared of.

Jason: No. The freeing thing 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.

Ben: Right, but then you're raising capital every single time you're making an investment.

Jason: Yeah, and I'm getting deal by deal carry and I have a 100% of my investment, not 25% carry on it. I don't ever have to talk to anybody. I could just say, I'm placing this bet. Would anybody like to join me? I don't have to have a fund, I don't have to do audits. I don't have to do any work raising.

David: 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. On the one hand, I could do what you just said and do very little work, but have it all be pure. On the other hand, I could go do what you are actually doing, raise, and have LPs, be accountable. How did you weigh these two?

Jason: I'm going into my second era, my second decade of investing. Again, the last two years, a lot like sort of post pandemic and Tony's death thinking what's possible here? Because I've won so much in my life.

I didn't mean to be obnoxious about this. I know it probably sounds that way, but for a kid who's going to be a cop to be where I am, and this is why like when the guys break my chops on the pod. I'm like guys, I don't aspire to be a billionaire. It's not important to me. If it was, I would do a late stage fund.

I aspire to be happy and do what I love doing every day, which is the podcast. Maybe get in 40 days of skiing, hang out with my kids, take them on the mountain, and then meet with early founders and be able to say, I help that company at the earliest stages. That, to me, is the rush. I found him first. I backed him first. I sat there with them and figured it out with them. That's the rush.

David: We were talking about the Legendary Twist episode 180 with you and Travis.

Ben: That's the secret before the show stuff, David.

David: Yeah, that is the secret.

Jason: I could talk about Travis.

David: Yeah, but Uber was such a baby company back then.

Jason: One city. I invested and I had an open angel for him with Cyan Banister and Chris Fralic from First Round invested in the company. I think they both met them there. Sacca was there too, but he had a relationship with Travis, so I can't take any credit for that. Kevin [...] was watching and I was going to kick him out because he was at this co-working space called Dogpatch Labs.

Ben: I worked there too.

Jason: He was sitting over there building Bourbon and Sacca was like, can Bourbon come in? I'm like [...], no. This is private [...]. Just tell him to sit at his desk and I won't kick him out.

Ben: Wait, this open angle forum was at Dogpatch Labs?

Jason: Here on the pier.

Ben: No way.

Jason: I think that year, they shut down because it was going to collapse.

Ben: Naval also did a bunch of like events there for Angel Labs.

Jason: At the time, Naval and I were very friendly. Not friendly now, we don't hang out, but we used to hang. I'm kind of bummed about that, if I'm being honest. I really respect him and he was doing something called Venture Hacks at the time. He would just send an email with, here are the five companies.

I was doing it in person and he's like, I'm going to do this in AngelList and I'm like I'm doing this in person. It's like great, let's just trade notes or whatever. Then he sent me the syndicate thing. He's like, do you know about SPVs? I was like, I don't. Explain it to me. He taught me what SPVs were. He introduced me to a sure fund management, which I wound up investing in.

Ben: Did you buy that?

Jason: I didn't buy it. I bought 5% of the company. I invested in it, but they back everybody and they've done more SPVs. I don't know if they're up to 10,000 or 5000. They've done a ton. Seriously great groups over there.

He taught me how to do syndicates, and the first one I did was Calm at $4 million or $5 million. Literally like winning a championship the first time you step on the court.

Ben: I was looking at your track record getting ready for this and I was telling David, I think the word that I used because obviously Uber's some ridiculous multiple on a return. But then there's these other ones that are promising but early, and then there's other ones where it's been less than Uber multiple. It's still a good Uber multiple. You look at Calm and I looked at David and I was like, he sharp shootered that one.

Jason: That one, I could be even more proud of because AOI.

Ben: It was ridiculously early and a super low basis.

Jason: It was $4 million. We put $378,000 on 6%. They didn't raise any money until it was a $250 million evaluation so no dilution.

Ben: Sharp shooter.

David: It's like Vanta. Vanta is the same story.

Jason: I could even cry telling the story. Alex and I became really good friends and Michael Acton afterward because he wasn't actively running Calm while Alex was. Alex had some conference. I was interviewing him, doing a little victory lap for him, and giving him flowers. He said I just want to stop and tell you you don't actually know this story but we were going to shut the company down and Mike and I had a conversation.

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. We had just pitched 40 investors and they all said no. We were trying to debate if we could, in good conscience, burn your money to do this. Probably Calm will not be here if it weren't for you.

Ben: They found product market fit while burning through your money.

Jason: Yes, I think so.

David: You're like take more of my money.

Jason: They think about that. That is not the case with Uber or Robinhood. I was along for the ride. Let's be honest. I did not change the trajectory of the company.

Ben: But for Jason Calacanis, Calm would not…

Jason: That's what they said. He said they were going to shut it down possibly. I don't believe that they would, but I do think it was on the table.

Ben: That's like real angel investing. There's a lot of like individuals participating in venture rounds and no offense.

David: I don't take any offense.

Ben: They call that angel investing, but coming in when the company could die, needs $100,000, $200,000, and $300,000 to get it to the stage where they—

Jason: They had $10,000 revenue to date when I invested. They were selling the app for $10. Remember, at the early stage, there was no subscription model.

David: Right, in the app store.

Jason: You sold it for $10 and you had it for life. The business model of apps was make a lighter for $1, and then make lighter two and charge $3, and then lighter four will come out. You're like, this doesn't make sense. Making Microsoft Word 1.0, you buy it and throw it away. You're like but we can just update it. Yeah, but we need to make more money so shut the 1.0 down.

You'd buy Angry Birds, buy Angry Birds 2, Angry Birds 3. It was a really weird time. They told me, because it was also under NDA as well, subscriptions are coming, it's going to change everything. They were going to do $10 a year. I said to Alex and Michael, how much does it cost to go to a meditation class? It's donation based and there's only like 10 places you can go. I'm like what's the suggested donation? It's like $20. I said you want to charge $10 a year versus $20 a month.

David: It's $20 a visit.

Jason: I said, how often do you have to do this to get value? I said it should be a daily practice. How often do you have to go and learn? I said if you go weekly, that's good. It's $80 a month to go and we're charging $10 a year. That's like $1000 a year versus $10. What if it was $10 a month?

They're like, We've been thinking about that. I was like okay. They were like, okay, I think we're going to do that. Then they went to $10 a month or whatever. They wound up at $60 a year, whatever it was, but it became a money printing machine pretty quickly.

Ben: I've never made an investment pre-product market fit that's now worth over a billion dollars. That's very early to successful. I'm curious, did it feel any different when you were making that investment? Were you like, is there something more special here than my normal investment?

Jason: Absolutely. That's what I've basically turned into a playbook at Launch and that I'm teaching these 12 people how to do that.

Ben: What do you think it was?

Jason: Nine factors.

David: Okay.

Ben: Angel.university.

Jason: No, I don't teach at angel.university, but I'm training my team when they're meeting with those 60 companies. And every time they pitch me one, they say this has three of the nine, this has four of the nine. Then I'm creating the anti-list. These are the things that kill companies.

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? One of them for me, and everybody's got their different ones, so I won't give all of them, but one of them is world class design.

I'm trying to teach people what world class design is. 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%. If you were to look at something like Calm or Robinhood. Okay, they're the best looking app with the best UX of anybody in the category.

Calm was better than Headspace, Robinhood was better than E-Trade. It doesn't take a rocket scientist to look at them. When I first explained this to my team, they would bring me companies and they'd say world class design. I really like the design. I'm like, pull it up and they pull it up.

I'm like that's a template from a website builder and it's a stock photo, but where's the actual design of the product? They're like that's on this product page. On the product page, I was like okay, again, 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 a good design. It's not world class.

If we're going to say a world class, a world class performance is different than a serviceable performance. World class cinematography, world class script, world class dialogue, that's different.

Then product velocity is the other one I like. We met with this company in June. It's now July. What's changed about the product? 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?

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 prioritizing this.

David: Then at one point, they're like check, check, check.

Jason: Then you go like if we're with Rahul with Superhuman, and I was an investor in his company before that report of Rahul changelog at Superhuman. Bank new feature, bank new feature. Oh boom, we fixed Grammarly. Oh, bank, we have a calendar. Boop, we got a new calendar feature. Boop, we got this feature and you're like hmm.

Ben: Here's an interesting question. We should ask Rahul because we've had him on the show three times now.

Jason: A product genius.

Ben: The parallels between Superhuman and Figma are uncanny. Design led founder, revolutionary design in the software, rewriting the entire browser stack in order to get the performance. 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. Why?

Jason: Outlook support. When you hit command K, you probably know 50% of the features. Do you use remind me of this?

Ben: I do.

Jason: Okay, great. Do you use labels? Do you do snippets?

Ben: I do, which was all there when I started using it three or four years ago.

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

Ben: It's just like polish, polish, polish.

Jason: I really want them to make snippets multiplayer. I want to share my snippets.

David: With your team?

Ben: I want all of David's past emails. They're so nice.

David: I don't do email anymore.

Jason: You do it on the phone?

David: No, I just don't do email. I don't email anybody.

Ben: David doesn't respond to emails.

Jason: I'm literally creating a collection of how to pass with my team and I'm standardizing that.

David: I don't know that I'll be successful, and this may be a mistake, but I'm trying to just not end up having a conversation with the company if I'm not going to invest.

Jason: No, but you must say, hey, we are not going to invest. You've taken a pitch. How do you say that?

Ben: You basically don't take a pitch unless you're going to invest. It's the weirdest thing.

Jason: Oh, that's very weird. You do all your work upfront? You front load it, the deck, everything?

David: We're in this unique position, as you are too. With Acquired, 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.

Ben: It's Vanta, Modern Treasury, and Vouch.

David: I'm now an investor in just about all of those companies.

Jason: Okay, fair enough. Got it.

Ben: It's growth stage investing. They're not well priced as if they're the winner. Most of them, they're going to just keep compounding.

Jason: Good luck. Pricing is going to be hard.

David: We'll see.

Jason: I don't know what's going to happen to this company. Flat is the new up, but I think 50% haircut is the new flat.

David: Public coms got hit 50% plus.

Ben: This week they got hit harder again.

Jason: I'm buying equities right now. I've been doing it at daytrading.com and I'm going to buy more.

Ben: Sorry about all the picks a couple of weeks ago.

David: [...] was the other one.

Jason: I actually love Taiwan Semiconductor. Twilio was yours and I love the one too. I like Shopify as a pick. I'm actually really enjoying it. It's really not investment advice, but it's balancing out my understanding of what public success is compared to private. For me, it's just a way of me going to fight with a blast or no, I'm a Jedi and I use a lightsaber.

David: If you look at the very best [...].

Ben: It's helpful. It's really helpful.

David: If you look at the best people, the best GPs in venture over the past two decades, they all trade public stocks. They do it for the same reason. They will fight with a saber, but they want to know how to use a blaster.

Jason: They had a fight on the next wing or something. It's not what a jedi does, but jedi will do it.

Ben: It also keeps you really sensitive to the public cycles. It's not that you have to think about the public comps when you're investing, but you have to be aware of how much those will change. Early stage investing, it's almost silly to compare. My opinion is it's very silly to compare to public comps because the only thing you know for sure is we're going to be at a different place in the cycle by the time this company gets liquid. It's ridiculous, but it's helpful to drive into how much variability there is, when was the last time it was this different?

Jason: Yeah. I'm really enjoying understanding what the founders of those companies go through versus the founders of the private companies that go through. What decisions the board has to make of a public company versus the board of a private company.

I'd like to join a public board at some point. It's probably not a good idea for me to have said that, because I might get an invite for one, and that might be too much work. Especially given the market right now, you better be careful. Some of them invite me to do that, but it's been great.

David: Especially through the show now, you have relationships with public company founders.

Jason: Sure, of course. If I really wanted to, I'm sure I could lobby.

David: You don't have to be on the board though.

Jason: Yeah. I'm just enjoying the analysis. I'm doing it anyway with Molly every day. Okay, Twilio's or Adobe's. I just bought Adobe this week when they bought Figma.

Ben: It's so funny, so did I. Not investment advice.

Jason: Yeah, not investment advice.

Ben: Okay, here's my theory on this. They bought Figma and tanked. I was like, why do people hate this? They're like, oh, no, Adobe is admitting defeat. They can't innovate in-house. To me, I look at it like Adobe has customer channel. It was foretold five-plus years ago that they were not going to build the next Figma. That would be a full rewrite of their entire software stack.

Even though they paid a tremendous premium, 50x revenue multiple because of the network effects that Figma has and obviously all the product stuff, but if they can get that through Adobe's channel, I think that is an absolute win-win acquisition. 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.

Jason: They're taking a YouTube approach. I think everybody in M&A knows now like let it be.

Ben: Or WhatsApp.

Jason: WhatsApp. Just leave it alone, don't screw it up. I like your analysis. I added to that analysis is if you're not going to win the war, you can build an alliance, and then fight another war. They've just removed the downside of Figma creating Photoshop.

Ben: I'd be concerned for Adobe if they didn't buy Figma.

Jason: Correct. The fact that you're giving us a discount on the shares for them doing the right thing is like Christmas, like thank you. You just discounted the right move. Fantastic. People are like, oh, the Warriors signed Kevin Durant.

David: They think the odds will go down.

Ben: But they paid a lot to get him on the team.

Jason: Yeah. And oh, you know what, we're going to lower the cost of the tickets. Okay, I'll buy courtside seats, or they're lowering the odds in Vegas. It's like, wait, why are you lowering the odds? Their odds increased. I'll place that bet, which is an obvious bet. And then all that's left is Canva, and Melanie's awesome.

Ben: Totally different thing.

Jason: Yeah. They have a free Canva already. There's always the internal people who are penciling out that spreadsheet. There is a group of MBAs who penciled out that spreadsheet with Figma. No offense to MBAs who are listening. And they said, hey, boss, if XYZ, and they said, here are five potential paths.

If we make Figma free for 10 users and whatever, or if we take whatever Figma costs and then we blend it with the Adobe Suite, okay, we would get this many more Figma users. But we know when we get Figma users, then we get non-designers to pay for it. Right now, Adobe has a bunch of designers paying, but they may not have all the non-designers.

David: Right, only designers pay Adobe.

Ben: They have marketing cloud, but that's a totally different set of.

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

David: Plus they got the whole creator class.

Jason: Exactly. I think you're opening up the aperture of who designed softwares for with Figma. It's for BD, it's where 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.

Slack is for the dev team, the sales team, and ops. Anybody else might as well be on it because that's where everybody is. That's one of the things that's going to happen to Figma. Everyone's going to have a Figma account in the future. Just watch the product team build the product and put a comment in. Who cares if it's $100 a year? It's the cost of doing business.

Ben: Any company that has that kind of strong network effects inside an organization deserves a meaningful revenue multiple because their differentiator is literally the company's moat. I tweeted this, but if I have a castle and it has a moat around it that is much wider or deeper than your identical castle, shouldn't you pay more for my castle that is more defendable?

Jason: Hundred percent. I think Sacks made this point on All-In two weeks ago, which was, if they're paying 50x now and the company is growing, okay, they're paying 20x next year or 25x. Who cares? It seems such a high growth company. And then I was just thinking, somebody's got a theory there.

When I sold Weblogs to AOL, people were like, oh my God, these people are idiots. They gave $30 million for Weblogs, Inc. They only got $200,000 in revenue. What they didn't realize was AOL Autos, AOL Tech, AOL Lifestyle, those were sold out at like a $90 RPM, revenue per 1000 pages. The ads were different CPMs.

They would put an Engadget or an Autoblog story, a 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. They would blow out $50,000 or $100,000 in ads a day on a blog.

Those people were like, great, because it was costing AOL to make content like $500 per piece of content, $3000 per piece of content on aol.com/autos, whatever. We were doing it at the time, $5 a blog post. We said, people can write for an hour, so it's $20 an hour and it's $6 minimum wage. It makes sense.

David: The media game has changed so much. You guys were $200,000 annual revenue?

Jason: We had done $200,000 to date over the 18 months.

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

Jason: People looked at the multiple and they were like, JCal just robbed AOL. I was like, okay, no. I looked like an idiot five years later. The best M&A is when you look like you robbed the bank and then five years later, it looks like you robbed the founder. YouTube.

Ben: Instagram.

Jason: Figma will be in this category. When they bought Instagram, 30 people work in this company and they gave them a billion dollars. You guys are morons. Now it's $150 billion company.

David: Yeah. Okay, 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?

Jason: It would do $10 million. When I was at the Code Conference, a lot of people have been trying to buy it or put it as part of their network, obviously.

Ben: Which would kill it.

Jason: Yeah. My partners are right. Let's not make money from it. Part of the delightfulness of it is that we're not trying to monetize it.

David: But you do get huge economic value out of it even without monetizing.

Jason: Chamath pulled me aside at some point. It was like, hey, schmuck, we're friends. Your next fund will be bigger in revenue.

David: Hey, dumbass.

Jason: Now, when you have a friend who can be like, hey, dumbass, that's a good friend, so I appreciate Chamath saying that. He's right. It's playing out. We had a rule. No talking our books on the pod, but we kind of talk about it and we're like, the pod is great when we talk about our bets. Explaining our bets, not talking our books is the new philosophy. Friedberg just talked about his SPAC.

Ben: Friedberg is still in SPAC.

Jason: Yeah, he did. He just found a target for it.

David: Chamath talked about the healthcare company.

Jason: The healthcare company. We wanted to talk about that because Chamath and I both agree, we're definitely over prescribing these drugs to kids for ADHD, attention drugs, and adults are taking too many. I think that that's not disputable. I think all the science is showing that.

To make software that could help kids with ADHD is noble. But I think people want to hear us explain our bets. 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.

Anyway, in the event, we did a couple million dollars and had a small profit, but it was the number one tech event of the year by far. I'm kind of bummed that Friedberg's a little bit of a blocker for it, but I might turn him around. We'll have a vote maybe in the fall.

David: You're doing another one?

Jason: 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? I told the guys, I'm going to do it again.

David: Code conference is done, so there's a vacuum.

Jason: Code conference is done. They need a new host.

Ben: That's crazy what they've done. It's such valuable.

Jason: I talked to Bankoff about it and he's been very public. Kara Swisher I think is going to do the pivot stuff and wants to do other stuff. I really respect what Kara has done. She does stuff, and then she moves on to the next thing and tries. It's kind of my approach as well, which is Bob Dylan said, don't look back kind of thing.

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, like Rolling Stone when he went electric, they booed him. I was like, really? You're booing Bob Dylan because he's using an electric guitar? Are you guys dumb? Did you hear All Along the Watchtower? This is incredible.

I think Kara Swisher is moving on, but Jim said he's going to keep doing it. It's probably a small list of people who could actually host that credibly. With very small list.

David: Which you're definitely on.

Jason: I am, you think?

David: How can you not be on it? I'm not even saying that to make you feel…

Jason: No, I'm joking.

David: Yeah, okay. You're joking about being humble.

Ben: But if it had that kind of prestige, it seems like Friedberg would want to do it. It seemed more like the thing he was averse to is the...

Jason: Yeah, whatever. We've had our issues. We all have issues. There are basically two possibilities for All-In Summit. I'm going to present it to the boys and say, here's the plan. Yes or no? And we agree, we'll put it to a vote, so we put it to a vote. If three of us want to do it, we'll do it. And if two of us want to do it, then we can't.

Friedberg already said, if you do it on your own with a different name, I'll come and support you. I'll show up to do a talk, do an interview, or whatever. I was like, great. I'll do it with a different name. If they don't want to do it and the fans can decide if they want to come or not.

Ben: Partially in.

Jason: Yeah, exactly. It's up to the boys if they want to do it, but it was a pretty great success.

David: You already have call-ins.

Jason: Yeah. I started doing a call-in show called After All-In for the last two episodes where I took calls about the last episode of All-In. This is for David because I don't think people remember how great that app is. It really made great progress. I want to be supportive of him. I have a small investment in it and it's very meaningful.

David: On the one hand, this is ridiculous to say. On the other hand it might be ridiculously low.

Jason: It's worth $50 million to answer your question, $50–$100 million. As a top 40 podcast, it's worth at least $50 million.

David: On its own though, but I mean economic value that the four of you—

Jason: Who knows. If Chamath, Sacks, I, or Friedberg were to get but one more deal out of it, and it's an Uber, the economic value is 9 figures, possibly 10. Yes, of course.

David: Man, Weblogs, you were doing $200,000 of revenue and you sold it for $30 million.

Jason: Pretty great takeaway.

David: Now look at this.

Jason: Yeah, I hope it keeps going. I hope we can keep it on track. I love doing pods. This Week in Startups is a juggernaut as well. It's been sold out for 10 years.

Ben: What is that, a quarter million listeners or something?

Jason: Yeah, something of that range. It's hundreds of thousands per episode. It's a very niche podcast. I'm not trying to make it All-In. I'm trying to make it for founders. In order to make it bigger, it has to be worse for founders.

David: It's like what we think about our show.

Jason: I want capital allocators to listen to it. I'm not trying to move up the rankings. I don't mind hanging with All-In being number one in tech and then hanging out with you guys at slumming it at 6-15 with you guys in the rankings. That's where we belong.

David: I got number one on [...].

Ben: Four to six, but who's counting?

Jason: Whatever. That's where we belong with these things. It's a niche podcast by definition. It's not supposed to appeal to everybody. If you want to appeal to everybody, read the Bible.

David: This is the beauty of the internet.

Jason: Literally, this guy who reads Bible passages. True Crime, read the Bible, or Ben Shapiro dunking on Libs. The end. That's how you get it or do it daily, but Joe Rogan's out. He's on Spotify. He's not in the other rankings. Do it daily, news program for 20 minutes, but that's not what I want to do. I want to talk for an hour or three about deep topics in founders and [...] with Molly.

David: You know what would be a fun Acquired episode is Howard Stern. I feel like it's underappreciated how much Howard Stern is—

Jason: That's the playbook.

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

David: He wrote the playbook for all of us.

Jason: I literally took notes for it, king of all media.

Ben: Do you know him?

Jason: I have never met him. I'd love to at some point. I have a lot of respect for him. Obviously, he did crazy stuff when he was young, that shock jock stuff. But he in his later years became a great interviewer. He really refined his technique. I really appreciate that about him. He created characters. sound familiar?

David: Yup.

Jason: He branded them. He showcased them, the Wack Pack and all this stuff.

David: Did he ever do an event?

Jason: He used to do live events. He did the US Open Sore, and then he would do Howard Stern's New Year's Eve Celebration. Yes, he did the equivalent of those in New York, but it was a very New York thing.

He played tennis against Baba Booey. He got 10,000 people to show up and buy tickets to a tennis match that they pumped up for whatever number of months. I remember this from my childhood. Then he did his books, which were phenomenal.

David: He did a movie, Private Parts.

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

Ben: Are you really?

Jason: Yeah.

David: Just you or the besties?

Jason: Just me. The besties don't want to do it. They don't have time for it. There was talk of maybe All-In kind of going on to one of those services. People have reached out like, hey, would this work?

David: It's a lot more work though.

Jason: We'd have to show up in a location. We'd have to do it weekly. There'd be some format, some shiny floor, or whatever. It's a different beast. I don't think they have the time for it if I'm being honest.

For me, I would like to do a reality show in the Gordon Ramsay kind of vein where I'm helping founders. I think it'd be great for reach. I had done a reality TV show with NBC, The Weinstein Corporation. It didn't make it on air.

Ben: You should be a Shark Tank judge.

Jason: They had reached out before. Mark Burnett had reached out early on when it was Dragon's Den before when they were going to bring it here. When it was Dragon's Den, they had reached out early, but I wasn't very successful back then.

Now I think I would have the credibility and the advice to give that I could do a Gordon Ramsay style show that would be very entertaining and educational. It'd be completely different than the fundraising aspect and the pitch aspect of Shark Tank, so I'm not going to do that. I've got, I won't say which one, but the very major reality TV folks reached out I think, in part—

David: Would founders and companies feel comfortable? I feel like a really amazing window and insight would be the type of conversations that you have with a founder as they're building the company. Would founders and companies be open to that?

Jason: Yeah. The NBC show I had done the pilot for, which never made it on air. What was really good was really about me incubating companies. They spent like $400,000 or $500,000 doing the pilot. It was really good, and it would have been a big hit.

Ben: Did it get canceled because of the Harvey Weinstein stuff?

Jason: Yeah.

Ben: Wow, so they were just like anything that was in his company.

Jason: All the IP is dead because he's a monster, so anything associated with it. But you got to remember, he did Project Runway. He had done some of these giant shows. People don't know about that.

David: That's why I forgot. Yeah, that had the TWC at the beginning.

Jason: Exactly. NBC bought the show in the room, loved it, and did the pilot. It came close. Chamath was on that episode. Actually, he did the pilot.

Ben: Oh my God.

David: No way.

Jason: He was my VC friend who came in. It's hilarious, but I'm excited to do it. If it works out, it works out. If it doesn't, no skin off my back. But I like the media space. 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. I want to enjoy.

Ben: You will not be gone soon.

Jason: You never know.

David: [...] your friends, yeah.

Jason: I have two friends who died young. I talked about it and I was like, I don't know, what if I make it another year or make it 25 years? But I want to make it count. I'm not going for max dollars. When the guys break my chops about that, I'm like, guys, it's not my priority. Literally, maximizing money is number—it's literally not in the top 10.

David: What is more money going to do?

Jason: You guys understand my life. It is ridiculous and charmed. I can do whatever I want. I have enough money, my kids are fine. I can have whatever I want. I don't care about a third home. I have a ski house, I have my regular house. It's good, I'm good. My kids have their college paid for, I'm good 100%. I literally do not care about more money.

Ben: Do you feel like that's a demon that you fight?

Jason: No, I had it when I was younger. I wanted to be powerful, I wanted to be important, I wanted to have money, I wanted to be seen. I wanted people to recognize my greatness like any person recognize me for what I do. I got all that. It literally does not even come up my radar. To have more money is the last thing I'm thinking about.

I do want to be the greatest investor of all time. To me, that's meaningful. I know Mount Rushmore for angels. I want to be Mount Rushmore for all investors. When you guys do your thing in 10, 20 years, it's like, okay, here's Doug Leone and Moritz. Here's John Doerr, here's Gurley. If we are making a Mount Rushmore, I would like to make it there or at least be in the conversation.

David: All right, listeners, we kicked Jason out of the room again because we have our next sponsor of the episode, our very good longtime friends over at Tiny.

Ben: The Berkshire Hathaway of the internet, if you recall.

David: Indeed. They're so much so the Berkshire Hathaway of the internet that as we told you about a few seasons ago, they literally built a business on the internet selling busts of Warren and Charlie that you can order.

Ben: Berkshirenerds.store.

David: Berkshirenerds.store. That's not what we're here to talk to you about toda, though.

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

David: Yeah. The core business of Tiny is acquiring wonderful internet businesses. These are businesses doing 5 million or more in revenue 30–40% operating margins.

Ben: The DNA really comes from Andrew and his partners originally running Metalab. Of course, it was very successful and is a very successful design agency that started spitting off cash. What do you do with the extra cash? They know how to run a great internet business with Metalab, so they started buying more and more and more businesses.

David: Companies like Dribbble, Pixel Union, Creative Market, 8020, Girlboss, these are all Tiny companies.

Ben: 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 are 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. Most venture capitalists were funding those businesses too.

You end up in this situation where you've got a lot of companies that have raised a lot of money that probably aren't tripling, quadrupling year over year the way you would expect a venture business to be doing to raise their next round of capital, especially in this environment. If the business is growing 20%, 30%, 40%, and it can get profitable or it is profitable—

David: It doesn't really make sense in the context of a venture portfolio.

Ben: Right, but the founders probably want to keep running that business. They probably want to keep serving those customers doing their life's work.

David: Exactly. You end up with a lot of these companies in a portfolio that are capable of being Tiny-like businesses, but are not going to provide a big exit that's going to move the needle for the venture portfolio. 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.

Ben: Really, what Tiny can do is come in, buy the company from the VCs or a lot of the company from the VCs—

David: The VCs get their money back, and most importantly, get their time back, get off the board so they have capacity to do new deals.

Ben: It's great for founders to keep doing their life's work. They can figure out a structure with Tiny.

David: Tiny's very good at figuring out structures that makes sense to align it to yours. It's really super cool. Honestly, I've talked with a bunch of folks varying different financial groups and institutions over the years who have had some version of this idea, and it's never gotten off the ground. I'm so glad that Tiny is now doing it. They are the perfect ones to do it, and this is the perfect time to do it. I'm very excited for this to exist.

Ben: Yes. If you are running a business like that, you are invested in a business like that, or your friend is invested in a business like that, you really should shoot a note to hi@tiny.com. Just tell them that Ben and David sent you.

David: Don't tell them Jason sent you.

Ben: He's not here right now.

David: You can say Jason sent them too.

Ben: All right. Our thanks to Tiny.

Jason: When you guys are having the conversation in 20 years and I'm gone or I'm retired...

David: It's hard to imagine you retiring.

Jason: Yeah, I know it's possible. I met Don Valentine when he was not active investable. When I pitched Mahalo, he was in the room. He came up, I talked to him.

David: He used to hang out there all the time.

Jason: He used to hang out, it's awesome. Yeah. Why retire? He was just awesome. But if you had that conversation right now about Mount Rushmore...

David: Who's on your Mount Rushmore?

Jason: You got to have Don Valentine.

Ben: How are you scoping? You probably need Paul Graham too.

Jason: Yeah. Paul Graham is in the running, for sure. That's a number of startups, but there's a lot of big ones in there. You have big impacts so Paul Graham is definitely running.

David: John Doerr?

Jason: John Doerr's in there. If you're doing firms, it's a lot easier because you get Khosla, Doerr, and Tom Perkins. You get the three of them at once. You do Sequoia—

David: People forget, Vinod Khosla spent a decade at Kleiner Perkins with John Doerr.

Jason: Exactly. Yeah. You look at that firm, that's like the OKC with James Harden, whatever. But then you have Doug Leone, Mike Moritz, and Valentine. If you put those three together for those 30 years and it's like, that's Mount Rushmore. It's a Mount Rushmore of Mount Rushmore's is kind of how you might look at it. You definitely have to have Sequoia and Kleiner.

David: We just did Benchmark.

Jason: You got to have Bill Gurley.

Ben: The Fab Four era of Benchmark.

David: The Fab Four era of Benchmark was truly something special.

Jason: It kind of builds itself, the Mount Rushmore right now. It's going to be Sequoia, Kleiner, Benchmark. And then we're going to have a big debate on the fourth arm.

Ben: It just depends how wide we're willing to scope it. Is it a traditional Series A type venture firm?

Jason: Is it AngelList? Naval? That had a huge impact.

David: Do you put YC in there?

Jason: YC or Techstars, both have a huge impact. What else can be in there?

David: You could argue for Founders Fund.

Jason: You can say YC in that. The Founders Fund is on the way.

Ben: YC is three orders of magnitude more significant.

Jason: For sure. They've done the same number of companies, I think, but just in terms of returns, yes. But TechStars I think was a little before Y Combinator. Anyway, definitely, Y Combinator is running for that four-spot, I guess. And then who else would you put in there, Masa?

Jason: No, but maybe the impact on the industry, no Founders Fund yet. Excel would be in the run for sure, Ron Conway.

Ben: 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 time before your firm hits Mount Rushmore is three successful generational transitions where each of the generations would have been on Mount Rushmore.

Jason: Right, so then let's just do this. Instead of Mount Rushmore because we're talking firms. For firms, you do Mount Rushmore. I think if you were just going to say the hall of fame, just the hall of fame.

Ben: Dude, we should open the venture capital hall of fame.

Jason: The capital allocator hall of fame top 25.

David: 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.

Ben: The Cuadrus Complex.

David: The Cuadrus Complex office, then it was Microsoft, Silicon Valley.

Ben: This is the internet.

David: Everybody else who cares about this is listening right now.

Jason: Sebastian who wrote the Parallel is like, you guys are taking this way too seriously. It's not that important.

David: TVI, Merrill Pickard, August Capital, Benchmark Capital, Shasta Capital, all in the same building. I think there is some space for rent in there. I don't want to go live down there, but I think we got to take out a lease just to put the museum. The hall of fame should go right there.

Jason: Venture capital hall of fame is something we should collaborate on. We should just do it. We'll do it every year. We induct somebody. We'll get up there, the three of us, and be like, this year we're inducting the venture capital hall of fame.

Ben: We should totally do this.

David: I know it exists. Cooperstown?

Jason: It'd be our Cooperstown. There is the computer history museum, but it's not for the PC, which is totally valid, but it's not for capital allocators.

David: It's not for people. Yeah, there should be a hall of fame.

Ben: Do we minus list style and ask people for the real hard truth members?

Jason: No, it's about impact.

David: No, we decide. The three of us, we decide.

Jason: It has to be impact on the game.

Ben: Does the NVCA have a Lifetime Achievement Award? Is that the closest thing?

David: It barely exists anymore.

Jason: No, it's about impact, legacy, the intent of the person. This is why Paul Graham would be first ballot. This is why...

David: Yeah. Okay, who's the first ballot entrance?

Jason: It's so obvious.

Ben: We've already talked about it.

Jason: We've already talked about. Those are all first ballot.

David: Do we have anybody who we haven't talked about or who is non-obvious, but would be a first ballot?

Jason: If you're under 20 years, let's wait until you're 25 years in.

David: Yeah. Just like the Sports hall of fames.

Jason: Yeah. You're not playing in the league anymore. Paul Graham is still playing in the league.

Ben: Does Jeff Bezos count?

Jason: How many investments has he made? That Google investment is crazy.

Ben: There's that, but I think Amazon is the best venture firm of all time just in terms of its internal. They're not separate companies.

Jason: Yes, capital allocating lowercase c, lowercase a. They've been great at placing bets.

Ben: You're right, Jeff Bezos is probably the most successful angel of all time, and LP.

Jason: When you're looking at it, I think you got to look at impact. Impact to the game, let's see. So is Carmelo Anthony Hall of Fame? Of course, he is. He didn't win a ring, he's Carmelo Anthony. Or Charles Barkley didn't win a ring.

Ben: Okay, so then we got like Arthur Rock. You got to look at the founding father type.

Jason: Of course, yeah. There's no doubt. That's like going back to Bob Cousy or whatever. We're going back to some people who built the league kind of situation before it became the league. You got the league, you have the people before the league, and you have people in the league. You can generational [...] right here, Patrick Ewing.

If you look at Gurley, he's part of that Patrick Ewing generation, that Hakeem Olajuwon, Charles Barkley generation. If you start talking about Founders Fund, YC, or AngelList, okay, now you're talking about more modern era. It's still going, modern era after 2000. But if you started before 2000, it's a different group.

Ben: Do you notice we haven't talked about Andreessen Horowitz in this conversation?

David: Impact on the game, they're in. Both of them are in, for sure. No doubt, first ballot.

Ben: They totally are.

Jason: I guess.

David: Impact on the game?

Ben: They totally changed the game.

Jason: I just feel like it's fortuitous. It's just raising $10 billion, three funds a year. I want to see what happens with the crypto stuff. I think they're just an index adventure. I find it quite soulless, if I'm being honest. I feel like it's a giant index on venture. I don't think that their hearts are super into it.

David: I do think they have interesting ambitions though.

Jason: That's the problem. It's more ambition than soulfulness.

David: Yeah, but there should be a JP Morgan or Goldman Sachs of Silicon Valley.

Ben: In The Bay? For sure.

Jason: I don't know.

David: Yeah. Why does Goldman Sachs manage the money of entrepreneurs?

Jason: Okay, fine, but I just feel like it's too premeditated and less soulful. I feel like it's a soulful business where your intentionality and your relationship with the founders really matter.

Ben: It's not the craft. It's literally the antithesis of its fund.

David: It's industrialization.

Jason: Yes, it's the industrialization of it. It's the factorization of it. I'm sure they'll be very successful. At the end of the day, all the returns be great, except for the crypto stuff.

Ben: There will be mean reversion. It's just like when you get the law of large numbers, you have mean reversion.

Jason: Exactly. It will be mean reversion for sure. At some point, they leaked a lot of their returns and they were like, eh.

Ben: Not fair. That was the 2015 thing.

Jason: What they did actually was early. Yeah, that was stupid that the journalist said it, but there were some older ones. During that time, you start comparing it to Sequoia or Benchmark. I think in the ark, it will not be comparable to Benchmark and Sequoia.

Ben: We made a lot of hay at the fact that they made $11 billion in profit on Coinbase. I do not think they sold out of that, so they did not make $11 billion in profit as of today.

Jason: Timing is everything. We'll see.

David: It's interesting too. Having just done this Benchmark episode, the Benchmark fund seven, one of if not the best institutional size fund of all time. It's just unreal. But even that, the fluctuation and the marks on that fund, it'll probably end up between 15x and 25x. Maybe, but it fluctuates up and down so much.

Jason: Yeah, of course. We live in a very volatile time right now. I like the Hall of Fame idea. It's kind of interesting.

Ben: Actually, it would be a fun thing.

David: We should get some space on Sand Hill.

Jason: No, I think we could just do it as like a dinner. Every year, we could just start in a restaurant, but you could get like a little hall. Say we're going to induct into the venture capital Hall of Fame the following people, and here they are. We just have three pictures, boom, boom, boom. You just drop it and you say here's three people, and then people come up and say something about the person.

Ben: I think we could do the three who we would hope would be there.

David: We do it like the sports where the person who's being inducted chooses who inducts them.

Ben: Sure, that's fun.

Jason: Roelof does Doug or whoever does Moritz. Sean Parker does Moritz.

David: Mike chooses.

Jason: Yeah, no, he can have Larry or Sergey come up.

David: He has Jason Calacanis come up and be like—

Jason: No, he can have Larry and Sergey.

David: Yeah, totally.

Jason: John Doerr would ask Bezos. It's a killer idea. We would just do Bezos, Doug, and Mike. We do one in memoriam. You do whatever, Don Valentine, Perkins.

Ben: It would be anticlimactic because we will induct on first. If the only person that we inducted that year wasn't a living person who could attend...

Jason: Yeah, you do a combo. Maybe it's four people a year. You have to think, how do you want to get to 25? You want to get to 25-50 over 10, 20 years, so maybe it's three a year.

Ben: In order for this to feel good, I think you're right that it has to be about impact, not about returns.

Jason: No, returns, that would be like saying it's like album sold for the Rock and Roll Hall of Fame.

Ben: To be a very Andreessen Horowitz way to do, it's what you're saying.

Jason: Yeah. What's the total assets under management? It's like, okay, dude, we got it. Yeah.

David: Nickelback sold a lot of albums.

Jason: Yeah, they're the Nickelback of venture.

David: No, I didn't mean that Andreessen.

Jason: You said that, you said it.

David: I wasn't talking about Andreessen. Oh, God.

Jason: The Milli Vanilli sold tons of albums. If you were to look at Ron Conway, who had a bigger impact, Ron Conway or Andreessen? I think it's a conversation.

Ron Conway, when I came into the industry, there was at one point I was at the Crunchies. At one point, somebody said, hey, can everybody stand up who said Ron Conway invest in their company? And 100 people stood up. My mind was like, oh, whoa, angel investing is cool. I wasn't an angel investor at the time long before I became a scout, but I always remember that moment when a 100 stood up.

Ben: That inspired?

David: Is that what put you in business as an angel investor?

Jason: The scout is what put me in business.

Ben: Was your Uber investment you personally or was that Sequoia's money?

Jason: That was Sequoia's money. Roelof and I were trying to figure out, do we let people know we're doing this or not? It was a big controversy at the time. We want to keep this stealthy, but Travis knew. It was a pretty great deal.

Ben: You split the carry 50/50?

Jason: 50/50 at the time, yeah. They dropped it down after that. Every time I see Doug Leone, it's like, 50/50 carry.

Ben: And they had 30% carry at Sequoia at that point, I think.

David: If I were you, I'd be 50% carry to them. I can't believe it.

Jason: They're so classy. Doug always make a joke. He was, was it 50% carry? Oh, God, we get 30, you get 50. It was just funny.

David: I love it.

Jason: We're very lucky, I think. If you look at what we do as capital allocators, I think it's a very special function in the world. I take it very seriously as you do for the retirees you're investing on behalf of, but also just think about humanity. I don't mean to make it heavy, but these companies do move the human species forward as—

David: Look at Elon.

Jason: Exactly. The human species getting moved forward by. As Steve Jobs would say in those commercials, this is the crazy ones. They do need fuel. They maybe don't have an idea if they should even build this company. I think the capital allocators really come in and say, here's some fuel. Here, go fight that war.

David: It's fuel and it's belief too. Your story about Calm is not uncommon, I think, amongst founders.

Jason: The stories about Don Valentine and Atari and other places where he was at Cisco, was like, we got to get this thing back on rails. This thing's going to zero. There's a lot of existential moments where things go to zero.

Ben: Can I ask you? As we start to drift toward the end of the episode here.

David: That's your favorite line. That's the Ben signature line.

Ben: Is this different enough from our normal show? What should we change?

David: Do you like this?

Jason: Yeah, I think so. I think a casual glass of wine. If you have friends of the pod and you want to go deep and talk about them in a more casual way, sure. I think it's a great way to just have somebody on again. If you profile somebody like, I forgot that you had done the first episode with me, and that was more about my career and more details, so I'm starting to tell stories over again. It's like, well, let's talk about some other stuff.

David: It's in a different context.

Jason: I like this format.

David: Lex has done so great with his show. Our shows are about the business of tech.

Jason: His is intellectual [...]. I don't know why he's in the tech vertical.

David: But I liked the format. Kevin Rose used to do foundation series.

Jason: Yeah, long form interviews. I think Joe Rogan stole it from Howard. I think it's now Lex stole it from Joe. I don't want to even say stole, I think, inspired by.

Lex is clearly inspired by Joe. Joe was in the running to replace Jackie Martling on The Howard Stern Show. People don't know this. He was very enamored with Stern. He wanted to be Stern, I think. He eventually has [...] in a way.

David: Yeah, he indeed become Stern.

Jason: Yeah, he did become Stern, so good on him. Yeah.

David: Break down to the do serious Spotify. Right down to it, he became Stern.

Jason: Yeah, doing a platform bet.

David: You're doing a platform bet.

Jason: Which is what Stern did. Stern had multiple platforms. He did syndication first, then he did the SiriusXM one, because it was a new platform. He used his number one show to build their platform.

David: But actually, to bring it all the way full circle back to Charlie Rose, he was more than business, but he would have—

Jason: He did culture business. Anybody in New York, because everybody in New York is pretty fucking interesting. He could have somebody from Wall Street, a publisher, an author of somebody who does films. He would have Spike Lee on. He'd have Woody Allen on.

He would have any actress on who was doing something interesting, any novelists, Margaret Atwood, anybody, which is coming from New York on a press tour. You would do your press tour, then you would just go chill with Charlie, and you would get to do something long form. It was a little sort of more jazzy, a little bit more like acoustic. I like this format for you, guys

Ben: Do you listen to SmartLess at all? Do you know about that show?

Jason: I have listened to one or two episodes. It's Bateman, Will Arnett, and then somebody else.

Ben: Yeah, the guy from Will & Grace, Sean.

Jason: I don't know who that person is, but they bring on a surprise guest each time, and the other people don't know. They're not prepared.

Ben: Yes. It's like Katy Perry, it's like Chris Pratt.

Jason: Yes. It's become a big deal.

Ben: I kind of want to do that of tech.

David: Wait, you and I don't know who one of us is bringing somebody. No.

Jason: You got to know the person's background much better. Because a celebrity just carry a certain charisma with them that our industry doesn't have.

Ben: It's true. It doesn't have to be a surprise. The other thing is, even though they have guests, the show is actually about them. The guest is a prop

Jason: In a way. Yeah, I guess. I've only listened to one or two. 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.

Ben: I don't think so.

Jason: It's really weird that Spotify doesn't allow Joe Rogan and call her daddy on iTunes because the advertising would be huge. Why not take the ads in and put them over there?

Ben: There's some [...] that's running the numbers that says it's more valuable if it's driving new subscribers for Spotify.

Jason: I guess that's it. I guess, you know what, they want to be able to have those new subscribers when they go renegotiate with the music. They're doing audiobooks too now, that's the next piece.

David: Yeah, that is the next piece.

Jason: Yeah, they're doing the audiobooks, one off purchases. It's smart. Audio is great.

David: All right, it's getting really hot in there.

Jason: For those of you who don't know, we're in—

Ben: A sauna.

Jason: Yeah, it's David's new house.

Ben: David just moved.

Jason: David's got a new empty house. It's sort of like The Shining.

Ben: There's no furniture. We just furnished this room.

David: Literally, this is all from Craigslist, all of it literally in the last two days.

Ben: That explains the smell.

Jason: Listen, you're rich, dude. Just go on and buy some at Crane & Barrel.

Ben: We can't all be Jason Calacanis.

Jason: No. Come on, man. I know those fees. Oh my God, and the ad revenue.

David: I love Craigslist. I love it.

Jason: You buy used furniture on Craigslist?

David: All the time. I do not buy new furniture.

Jason: That's going to stop, come on.

Ben: I bought a temporary couch on Craigslist.

David: It's the thrill of the market.

Jason: No, you're going to get robbed. Don't do it, it's too crazy. Craig Newmark, I love you, but no.

Ben: All right, with that, our thank you to Vanta.

Jason: Vanta.com/acquired.

Ben: You don't know who the other sponsors are because we haven't talked them live with you because we wanted to make better use of your time.

Jason: I love reading ads.

Ben: Do you want to read our Brex ad?

Jason: They don't sponsor my pod, so no. Maybe they have, I don't know. We're talking about Brex part. I know people who use Brex. I think we use Brex in one of my companies.

Ben: If you're enterprise, if your global, by far the best corporate spend management.

David: It's much more than a card now.

Jason: Yeah, for expenses and everything like that, and then they've kind of expanded behind that. You can give cards to each of your employees. Then if they screw up, you can turn it off or something.

Ben: Pre-approve some budgets.

Jason: Yeah. You don't want people jumping the fence. It's crazy.

Ben: All listeners know because they heard it an hour ago. They're very familiar with it.

Jason: Because I didn't hear you. Anyway, shoutout, Brex.

Ben: We share this last sponsor.

David: These are great folks.

Ben: These are our dear friends, geniuses, and rock on tours.

Jason: Masterworks?

Ben: No.

David: No. Good guess, though.

Ben: Think smaller but bigger.

David: Literally small.

Ben: But secretly huge.

David: Tiny.

Jason: Oh, Tiny, of course. Yes, they're buying companies.

Ben: They're buying companies.

Jason: They're doing a good job. Yes, they're creating like the Berkshire of the internet.

Ben: Can you imagine a better time to get the monkey off your back of venture capital?

Jason: Yes, sell your company. Secure the bag.

David: That's my favorite JCal line. Secure the bag.

Jason: Let's go, man. Trust me. If you haven't secured the bag yet, it's a wonderful experience, man. There's nothing like getting home with a bag. You get that Tiny bag.

David: You get that AOL, Weblogs exit.

Jason: Man, let me tell you something. I'll tell you the story.

David: What did you do when you secured the bag?

Jason: I'll tell you what happened. I got this a funny story. I'm in my office. I got Bank of America. I got low thousands of dollars in my Bank of America account. I got an American Express card with -10 on it and a visa with -5 or -10 on it. I'm sitting there and they're like, oh, wires are good. The BD people or AOL. I'm hitting refresh on the thing, refresh.

Ben: This is 2006, 2007.

Jason: 2005, 2006, yeah. I'm hitting refresh, I'm hitting refresh, and then bink, bink, bink, bink, bink. All the numbers come in for the whole amount.

Ben: And you own most of Weblogs, Inc., right?

Jason: Brian and I were equal partners. We had Peter Rojas had some ownership, and then Mark Cuban was our big investor. By big investor, he put $300,000 in for 5%. That was a great outcome for him or more. Maybe like 10%, I think he owns 10%.

Anyway, long story short, my wife comes in. She's like, you okay? And I said, what? She said, are you crying? And I reached out and I had a tear in my eye.

David: You're like, this is a new experience. I've never had this before.

Jason: She said, why are you crying? And I said, my family will never have to worry about money again because I spent my whole life worrying about money. My dad had lost the business. It was a very cathartic thing for me.

I think people who are already rich or maybe who come from means, they don't understand the concept of living with the fear of being broke and in debt all the time. 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, for securing the bag.

David: Acquired.fm/tiny.

Ben: They only gave us a thing.

David: Tell them that Ben, David, and Jason sent you.

Ben: You can mention Jason.

Jason: But I did buy a one touch espresso machine. I bought a JURA one touch espresso machine, which at the time was like $2000. I was like, this is unbelievable. Then I tried to buy a Ferrari. They wouldn't sell it to me in Beverly Hills.

Ben: What, like, no new money or something?

Jason: Yeah, basically. I went in there and they're like, oh, yeah. I'm like, I want to buy a Ferrari today in 430 and they're like, oh, we don't have any available. I was like, okay, can I put myself on the waitlist? They're like, we're not taking into the waitlist. I said, okay, can I ask what do you do here? He's like, we sell Ferraris. I'm like, to who?

David: This is part of their strategy though.

Jason: It's part of the strategy.

David: It's part of the strategy. They have the Ferraris, but they don't sell the Ferraris to build mystic.

Jason: We're not putting in anybody on the list. I was like, well, how long is the waitlist? I was like, okay, I'm a cash buyer. He's like, everybody's a cash buyer. I'm like, okay.

Can I ask you a question then? He's like, sure. Come into my office, we're going to have espresso. You want some Pellegrino? I was like, no, I'm good. Literally, offering me Pellegrino espresso. I was like, I have the same one touch. Sure.

This Italian guy is like, I don't mean to be rude, but what do you do here all day? He said, well, we deliver the cars, we service them, and we sell used cars, a pre-owned certified. I was like, well, I would take a pre-owned one. He said, oh, well, the one you're looking at is pre-owned. I was like, no, no, no, the one I'm looking at, the 430, red one out there, that's the one I want.

That's got a sticker in the window. He said, yeah, we certify them. We put the sticker on the window. I said, oh, well, that goes for $230,000 or whatever. Yeah, what do you want for? He's like, $300. It's the used one I was looking at. He's like, hey, you can't get these cars. I was like, ah.

You pay over $70,000. He's like, there's only 2000 miles on it. I was like 2000 miles, it's $70,000 more than new. I said, why wouldn't I buy a new? He said, because you can't get them. I'm such an idiot from Brooklyn who doesn't understand the concept that people would pay over for the car. I'm just perplexed.

Ben: That would bother me too.

Jason: I said, all right, well, let me think about it. I left. I was with my friend. I had the Robb Report and it said the number one car was the Ferrari F30. Then I turned the page, it was Corvette C6 was the number two car. The starting line was buy two for half the price of a Ferrari and beat them off the line or something like that. I was like, let's go to the Chevy store.

I walk in, there are Corvettes everywhere. The guy looks at me and he goes, you want to buy a Corvette? I said, yeah. He said, if you buy a Corvette today, I'll give you $5000 off. I was like, yeah.

We go out on the 405 and we're driving the Corvette. He's like, is a Corvette sound like you're going 70 miles an hour? He said, I'm not selling this car to you unless you hit that gas much harder. I said, okay, and I punch it to 100 miles per hour. The guy's like, yeah, how does that feel? I'm like, great.

We go back. I come home with a Corvette. I come home with a yellow convertible Corvette. My wife's like, what happened to the Ferrari? I was like, this thing only cost $65,000. It's $70,000 and I got $5000 off.

Ben: And it's American, baby.

Jason: And it's American. 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 racing.

We were driving them along Sunset Boulevard. A spirited drive along Sunset Boulevard, and we did it five times. Five out of five times, the Tesla just destroyed the Corvette. I was like, I'm doing something wrong. Then we switch cars and I was like, no, electric is going to beat everything. This was the first one, the prototype. That's in space right now. It's the cherry red one that's in space.

David: Oh, that's the one that's in space.

Jason: There's a famous photo of me and Elon in front of the Corvette.

Ben: With the spaceman?

Jason: That was it. There's a famous photo of the two of us in front of my Corvette and his P1. I remember that night like it was yesterday because this was before the iPhone, you realize like Robert Scoble was recording this on his Nokia smartphone.

Ben: These are the memories. This is the journey that you've been on. This is the stuff you will cherish forever.

Jason: My life is unbelievable. I'm so grateful for it. Thanks for having me on the podcast.

Ben: Listeners, thank you so much. Acquired.fm/slack. Come join us, we'd love your feedback. This is a new schtick. Acquired.fm/store, you can buy cool shirts. Acquired.fm/jobs, find your next work experience. I just done a bunch of new ones.

David: It's so fun. Thank you so much.

Jason: Of course.

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

I am curious what you liked, what you didn't like. 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. We've had the wonderful problem of our audience growing a lot since the last time we did one of these. We no longer feel like we have a great handle on who all of you are.

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 a 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 have some I think better battery life too. David, for you, they have very tiny little ear tips, right?

David: Yes, for my tiny, tiny ears. I'm so excited about the extra small tips. They finally fit in my ears

Ben: It's awesome. Ten other winners will get acquired t-shirts from our fancy new merch store. Again, three minutes to participate at acquired.fm/survey or you can click the link in the show notes. Thank you so much for helping us. It really does help us run the show here at Acquired world HQ.

All right. 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. With that, listeners, we'll see you next time.

David: We'll see you next time.

Note: Acquired hosts and guests may hold assets discussed in this episode. This podcast is not investment advice, and is intended for informational and entertainment purposes only. You should do your own research and make your own independent decisions when considering any financial transactions.

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