Special: Jason Calacanis

We're joined by the one and only Jason Calacanis for this very special episode, wherein we chronicle Jason's journey from a kid porter in the barrooms of Brooklyn to building the largest independent media business in tech, becoming the "3rd or 4th greatest seed investor of all-time" (and the original Sequoia Scout), launching one of the top accelerators in the world, and constructing a one-man empire that may just disrupt the entire capital stack in our industry. We dive into how it all ties together, and where the money and power is shifting in the ever changing sands of Silicon Valley... Sponsors: Vanta: https://bit.ly/acquiredvantaServiceNow: https://bit.ly/acquiredservicenow26Legora: https://bit.ly/acquiredlegoraStatsig: https://bit.ly/acquiredstatsig26 More Acquired! Get email updates https://www.acquired.fm/email with hints on next episode and follow-ups from recent episodesJoin the Slack http://acquired.fm/slackSubscribe to ACQ2 https://pod.link/acquiredlpMerch Store https://www.acquired.fm/store! © Copyright 2015-2026 ACQ, LLC

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  Let me just make a little ad here.

• 0:01Ben Gilbert?

  Yeah, please.

• 0:01Speaker 00

  Hi, this is Jason Calacanis for acquired.fm. Is that the domain?

• 0:05Ben Gilbert?

  Acquired.fm?

• 0:06Speaker 00

  That is it.

• 0:06Ben Gilbert?

  Yeah.

• 0:07Speaker 00

  All right, listen, you're listening to this, you're either a founder, an aspiring founder, an investor, or an aspiring investor. For $100 a year, you're going to get hours of content that's not available to everybody else. That's also known as an edge. You are in a competition with other investors, you're in a competition with other founders. You need an edge. If I could tell you, you get one, two, three good insights a year, even one, would you pay $100 for an amazing insight that gave you an edge against your competitors? Of course you would. You'd pay $10,000. So why wouldn't you pay 100? Because it's content? You're thinking about it the wrong way. The LP program at acquired.fm is not, it's not content, it's an edge,

• 0:50Speaker 00

  and it's an underpriced edge. So buy it for 100 now, before they raise the price to what it should be, which is 5,000 a year. This is Jason Calacanis for acquired.fm. See you in the Slack.

• 1:01Ben Gilbert?

  How's that for an ad, huh?

• 1:03David Rosenthal?

  You can have that. Mic guy, can you actually take your mic out? You can literally have my ad.

• 1:07Ben Gilbert?

  You can have my ad.

• 1:08Speaker 00

  I swear, we did not ask him to do that, everyone.

• 1:10David Rosenthal?

  No, I just love doing ads.

• 1:11Speaker 00

  Thank you.

• 1:23Ben Gilbert?

  Welcome to this special episode of Acquired, the podcast about great technology companies and the stories behind them. I'm Ben Gilbert.

• 1:32David Rosenthal?

  I'm David Rosenthal.

• 1:33Ben Gilbert?

  And we are your hosts.

• 1:35David Rosenthal?

  Acquired is all about stories. Ordinarily, we tell the story of a great technology company, or a great leader, or a great adaptation. Today, we are telling the story of someone who doesn't just have one story, he has a whole anthology across all of those categories, the one and only Jason Calacanis. So just to give our audience a small sampling of all of the enterprises that Jason has started and is involved with across his career.

• 2:03Ben Gilbert?

  Yeah, David, I bet you can't do this all in one breath.

• 2:05David Rosenthal?

  Oh, no, no. Jason has founded four companies, by our count, Silicon Alley Reporter, Weblogs Mahalo, and Inside.com. Do we miss any?

• 2:16Speaker 00

  No, those are them. Those are the four. And Inside.com is the same cap tab, which is the pivot of Mahalo. So arguably one.

• 2:22David Rosenthal?

  Did not know that.

• 2:22Speaker 00

  People don't know that.

• 2:23David Rosenthal?

  We'll get into that. Three conferences, three podcasts, Angel, All In, and of course, This Week in Startups, which is now over 1,000 episodes, the YouTube channel around all of those. You were the first Sequoia Scout. You were literally the prototype of the Sequoia Scout.

• 2:38Speaker 00

  Correct. And still the greatest returner.

• 2:41David Rosenthal?

  And still the greatest returner.

• 2:42Speaker 00

  But who's counting? It's not a competition, but I won.

• 2:45David Rosenthal?

  Maybe some time might have something to do with it. Well, anyway, we'll get into that. You've made over 200 angel investments in your career. You're a blogger. You're an author. You have a newsletter. You started the Launch Accelerator, the venture fund around that, the syndicate around that. You are the self-provest. We have you on record as saying you are the either third or fourth best angel investor of all time.

• 3:07Speaker 00

  For sure. Yeah. For sure. Mount Rushmore.

• 3:11Speaker 00

  Chris Saka, Ron Conway, obviously ahead of me. And then there's a bunch of people. Nobody knows who did incredible angel investments, you know, in Google and Apple, but they don't have like, they don't feel the necessity to put it on the cover of a book like I did.

• 3:26David Rosenthal?

  Speaking of, quote that we want to wrap this up with from your book, "Most folks think I'm lucky. Some say I'm a complete fraud and a handful think I'm a brilliant hype man. I don't agree with any of them. I agree with all of them." Jason Calacanis, welcome to the show.

• 3:41Speaker 00

  Big fan of the show. Thanks for having me on. And David, thank you for doing that intro because your voice is so much better than Ben's. I mean, that is a radio voice you have, David. It's so soothing. And Ben and I are just like, scratchy records. But Ben's got good insights. So I'm glad to be here. I'm a big fan of your podcast.

• 3:59Ben Gilbert?

  Got to have something to rely on, Jason.

• 4:01Speaker 00

  Exactly. The insights.

• 4:03David Rosenthal?

  Thanks for joining. So, okay, today, probably most people listen to, subscribe to Jason on one of these many channels we've talked about. Today, we're going to talk about two sort of less discussed parts of Jason's story. One, on the main show here is how Jason has built his whole empire across all these properties and how it all ties together in his mind. And then two, right after this on the LP show, we're going to talk about what the bigger picture is behind said empire, what Jason's secret master plan is, Allah, his friend Elon, and why it might represent a wholesale deconstruction of the entire startup ecosystem. So you can click the link in the show notes or go to glow.fm/ acquired.

• 4:47Speaker 00

  I'm a member. I pay a hundred bucks a year or something. Well, thank you. We appreciate it. It's worth it. The LP show is like the best parts. It's like you cut the nice, like the rib eye and that's like the best part. It's like the New York strip of the podcast.

• 5:02Ben Gilbert?

  It's great. Well, we hope that the whole podcast is good, but we appreciate.

• 5:05Speaker 00

  The LP stuff is the tightest, I have to say. You guys put the most work into that and people just pay for it. You want good content to exist, pay for it.

• 5:12Ben Gilbert?

  If only all of our guests were like you, Jason. All right, listeners. Now is a great time to tell you about a longtime friend of the show, Vanta. AI has scrambled the whole security picture. It used to be that you proved that you were secure once a year on audit or a static PDF, then everyone would nod and you're done. But in an AI-first world, that doesn't hold up anymore.

• 5:34David Rosenthal?

  Yep. Your risk surface changes every week now. A vendor turns on an AI feature or someone writes in a new model without telling IT and your posture is different than it was last week, let alone at your last audit. Vanta's own research found that around 70% of companies have this quote unquote shadow AI running with no security review at all.

• 5:55Ben Gilbert?

  Right. And that's where Vanta comes in. They're the leading agentic trust platform, meaning they've built the thing that closes the gap. And the way that they close that gap is Vanta Agent. Think of it as a GRC engineer, that's governance, risk and compliance, except that it's software and it doesn't sleep. It finds the issues, drafts the fixes and cuts the time that you'd spend on vendor assessments in half.

• 6:16David Rosenthal?

  In half? Which is exactly why more than 16,000 companies today run on Vanta. Companies like Ramp, Cursor and Snowflake all stay audit ready and catch the risks that crop up between audits across every vendor, every AI tool, the whole environment.

• 6:35Ben Gilbert?

  And that's the real value. Trust has to be continuous now, which is why Vanta automates your security, your compliance and the work to earn and prove trust. We're huge fans of Vanta over here and literally hundreds of acquired listeners have become Vanta customers at their companies over the years. So you can get $1,000 off Vanta at vanta.com/acquired. That's V A N T A dot com slash acquired for $1,000 off and just tell them that Ben and David sent you.

• 7:02David Rosenthal?

  So Jason, you've talked a lot about growing up, your childhood. So we'll do that briefly here. You're born in New York, right?

• 7:11Speaker 00

  Brooklyn.

• 7:12David Rosenthal?

  Brooklyn.

• 7:12Speaker 00

  Yeah. You know, when you come from New York, you don't say New York, you say, not only do you say the borough, you say the part of the borough. So I'm from Bay Ridge, which is literally the last stop on the train, on the train.

• 7:25David Rosenthal?

  Love it. Tell us a little bit about your family and what growing up was like for you.

• 7:30Speaker 00

  Yeah, I grew up in the seventies and eighties, which was a fantastically interesting time to grow up as a young person. We were free range kids to the extreme and Brooklyn and, you know, was not hipsters back then. It was, you know, working class and connected guys and the Hells Angels and cops and bookies. And it was, it was a little bit more rough and tumble. My dad owned a bar. He was essentially the mayor of Bay Ridge in a way, like people loved my dad, John the Beard, and they loved his bar. And I worked at his bar, my brother, my two brothers and I, my older brother, my younger brother, Jamie and Josh, from a very young age. My mom was a nurse and she ran the emergency room in Brooklyn at

• 8:14Speaker 00

  Victory Memorial Hospital and then later ran the ICU. She's a nurse practitioner and she's got, I think, three graduate degrees. So I had this amazing, hardworking mother doing three or four jobs, had this amazingly hardworking dad and it was a blue collar. Lifestyle, we're, you know, we owned our house, but barely. Um, we were always living month to month. But there was a lot of love and a lot of craziness, uh, growing up in a bar. I literally grew up in a bar and made espresso for mob bosses, made baked clams for Tony Bennett. Uh, would go get cigarettes for the coke dealer, would put ballys in cappuccinos for police officers in uniform, coming in at two or three o'clock to have a steak or burger.

• 8:59Speaker 00

  Cause my dad would let them come in at any time.

• 9:02David Rosenthal?

  It sounds like not just a bar, this is more like a pub.

• 9:05Speaker 00

  It was a pub, exactly. It was kind of like a pub, uh, and the cops would come in anytime they wanted, but usually they come in between lunch and dinner. And, uh, my instructions were just give them whatever they want and just charge them 10 bucks each. And they would proceed to drink four or five Irish coffees each.

• 9:24David Rosenthal?

  Did they order them as Irish coffees or?

• 9:26Speaker 00

  Yeah, no, there was the wink and then it was the wink, you know, they, they, we were in uniform. So they just wanted to have a cup of coffee. Hey kid, get me a cup of coffee. And whenever I got the bookie, Artie Mareska, uh, or the, uh, the guy who dealt cocaine, uh, his pack of cigarettes or whatever, they would just say, here's 20 or here's a 50 sometimes, or sometimes even a hundred. Go give me a pack, give me two packs of Marlboro Lights. I go out and get two packs of Marlboro Lights. It was two, $2 or a dollar 50 a pack. And they'd say, keep the change.

• 9:53David Rosenthal?

  This is like the Brooklyn version of, uh, Bob Iger's story with, um, with the chairman, Frank Sinatra going out and getting him mouthwash.

• 9:59Speaker 00

  Exactly, exactly. And, uh, so, you know, I, I basically got exposed to commerce at a very young age and I became very interested in power and money. Perhaps too interested in it. My first real job was a guy owed my dad like two grand. He had lost playing backgammon to him. My dad used to have a backgammon and a poker game. And when the bar closed at four, the fun began from four till seven or eight in the morning. They had after hours, uh, which was mainly cops and Hells Angels, mafia guys and, you know, hippies.

• 10:30David Rosenthal?

  Playing together.

• 10:30Speaker 00

  Yeah, yeah, yeah. And I would come and I would do the porter work at 7:00 AM. So I would come and sweep up the place on Saturdays and Sundays when I was 10, 11 years old, uh, with my grandfather, rest in peace. And we were the porters, fancy way of saying janitors and, um, my dad would be there playing cards or whatever. Anyway, this guy got, he was in for two grand, too large to my dad and, uh, he couldn't pay. And he needed a little time. So my dad was like, that's fine. He said, here, I know the kid likes the Star Wars. Here's the Empire Strikes Back. And Empire Strikes Back was in the theaters. And he handed my dad a VHS tape. And my dad had gotten a VHS player that had fallen off a truck. This is before Blockbuster, obviously. This is like 1984 or something. I don't know, 85, no, 83, 84, something like that. They were just starting to have video rental stores,

• 11:15Speaker 00

  but something like Star Wars would never be allowed there. It may become five years later. Anyway, long story short, I was like, this is incredible. I have Empire Strikes Back. And I had my friend bring his VHS over and I made copies of it. And my first job was Jason's Hot Tapes. I would make copies of the Empire Strikes Back and sell them for 20 bucks.

• 11:32David Rosenthal?

  That's, I thought you were gonna say you started running screenings.

• 11:34Speaker 00

  No, that would be a better idea, actually. But anyway, it was before Jason learned about marginal costs. Exactly. I was like, wait a second, how much does a VHS tape cost? My math teacher says, hey, Calacanis, stay after. I'm like, oh, God, I'm gonna get pinched. And so he says, I know you're selling this tape. I said, yeah. He goes, you think that's an okay thing to do? And I was like, no, I probably shouldn't be doing this. Do you have these tapes with you? And I said, yeah. He goes, how much are they? I said, they're 20 bucks. He said, okay, I'll take one. And I said, here, it's on the house. I gave him the tape.

• 12:16Speaker 00

  It was literally, I mean, when I saved my life, I was watching Goodfellas. I was using this Chrome extension called Seener that we invested in to watch Goodfellas with some fans of the show. And I had just tweeted, it's like group viewing. You know, like there's Netflix party and this is Seener. So now that everybody's home, you can watch Netflix with your family, whatever. So I put on Goodfellas and I was just watching this kid growing up and I was just having flashbacks. I mean, literally, my life was like the first act of Goodfellas.

• 12:42Ben Gilbert?

  Well, Jason, I'm going to deviate from our little outline here a little bit, but like, I know you're a prolific poker player. Like, I don't know if semi-pro is the right word, but you play with pros, you're friends with pros.

• 12:52Speaker 00

  Yeah.

• 12:52Ben Gilbert?

  A lot of your investing patterns sort of match poker patterns.

• 12:56Speaker 00

  Informed by, yep.

• 12:57Ben Gilbert?

  Yeah, so did that start here? When was your early poker game?

• 13:02Speaker 00

  It didn't. I was exposed to gambling at a very young age. I didn't participate in it. My exposure to poker came when I was in New York. A friend of mine, Adele Resi, who started the Founders Institute, just started a $20, $30 poker game. And myself, Scott Hyferman from Meetup.com, Nick Denton had come to a couple of games, Jeff Dotch is from Razorfish, and now One Drop, which I'm an investor in. Just a bunch of like the Silicon Alley folks would play cards, and I'd play cards with them. And nobody, it was like one of those card games where people said, what's better, a straight or a flush? And somebody had to like, look it up, kind of thing.

• 13:35Ben Gilbert?

  Yeah, you have the little card next to you on the table, or you're sort of referencing it.

• 13:38Speaker 00

  Yeah, literally. That was like that. It was just an excuse. And we used to play down in a place called Forlini's, which is still down in Chinatown, which is like an Italian restaurant. I'll leave it at that. And we used to play in the back. But then I went, when I moved to LA, and I spent a decade in LA, a lot of my friends, like Sky Dayton was playing cards, and my friend Kevin Pollak, who I was friends with, the actor, he was playing cards. And we just, you know, those games were $200 buy-in or $500 buy-in. So you had to be a little more serious about it. And then I, you know, the stakes started going up. I tried to study the game. I was terrible at it. And then I started getting invited to this game. This woman, Molly, kept inviting me, and she'd be like, oh, Toby really wants you to come to the Four Seasons, and Leo really wants to see you. And I was like, Toby and Leo want to see me lose 20 grand. Like, they

• 14:23Speaker 00

  don't want to see Jason Galgadis. So I never went to Molly's game, but she invited me frequently, because I was a fish or a well, as we say in the business. But yeah, that's when I got exposed to it. And then one of the, in the early D-conferences, myself, Bill Gurley, Mark Pincus. And Sky Dayton, we're all there and we say, hey, you guys want to play cards? And we went up to, I think it was Mark Pincus's room. We just took the folding table. We started playing cards and then we started hosting this game at the D Conference, which later became Recode. It became very famous, this poker game. And then we have a weekly poker game that everybody knows about here in Silicon Valley. You know, it's just my best friends and Phil Hellmuth and Draymond from the Warriors,

• 15:05Speaker 00

  Chamath, obviously, and David Sacks. Just a really good group of guys who get together and we've been playing virtually now, which is kind of fun.

• 15:14David Rosenthal?

  And now you have a podcast around it.

• 15:16Speaker 00

  Well, Chamath was just like, Chamath was one of these guests on my podcast who he just burned the building down and he, nobody really knew who Chamath was until he came on my podcast and, you know, we started having him at the events and then CNBC got their hooks into him and now he's just like throwing bombs for a living.

• 15:33Ben Gilbert?

  Well, I'm sure he gets like just incredible page views whenever he goes on CNBC and drives through traffic.

• 15:39Speaker 00

  Yeah, it's just a problem for me though, because he's like, let me come on your podcast and just say, everybody's a fraud in venture capital. I'm like, I know you made your money and you're retired and running a family office now, Chamath, but I'm raising funds right now.

• 15:53David Rosenthal?

  Yeah.

• 15:54Speaker 00

  Doesn't really help me to have you on the podcast saying that this is a giant Ponzi scheme. And he's like literally pouring gasoline over himself, lighting himself on fire and I gotta like step six feet back to burn the building down.

• 16:06David Rosenthal?

  This is great because this is the perfect segue into the media business.

• 16:11Speaker 00

  Yeah.

• 16:12David Rosenthal?

  So when, so you go to Fordham.

• 16:13Speaker 00

  Yep.

• 16:14David Rosenthal?

  After Ford, was it right after Fordham?

• 16:15Speaker 00

  At night.

• 16:16David Rosenthal?

  You start as a, at night, you start as a reporter. How, so what draws you into the media business? Because to my mind, this is the, this is the, well, obviously you're growing up years and everything, you know, that shaped you then, but starting in the media business is the wedge that brings us all to the Calacanis empire now.

• 16:32Speaker 00

  Yeah, so this was a very interesting thing. What happened was, you know, I would go into Manhattan. I was just in awe of the people in Manhattan and people who were rich or famous and who were powerful, because I had no power growing up and I was in a very dangerous situation and I was watching people who were powerful and I was like, okay, the book is very powerful. The head of the Hells Angels is very powerful. This cop is very powerful. I am not powerful. My dad is powerful. He's got all these people in his bar. And I was watching money go around and I was just fascinated by these topics, probably too much. And I saw magazines and

• 17:12Speaker 00

  magazines are how information was really transferred in the 80s and 90s. And so I just started subscribing to every possible magazine. In the 80s, I got all the PC magazines and Bytes and all that kind of stuff. And then I started, you know, this Esquire, this paper magazine, Time Out New York.

• 17:29David Rosenthal?

  So you were kind of a geek even back then?

• 17:31Speaker 00

  Yes.

• 17:32David Rosenthal?

  It wasn't just that you were like, you know, reading Esquire or like The Source or whatever, like you were, you're reading the tech plugs.

• 17:39Speaker 00

  I was reading all the tech stuff and I was really into technology. I had a PC Junior computer that my dad had bought me with cash from the restaurant or poker game. I was doing a little phone freaking, which is like getting phone codes. Anyway, I was involved in a bunch of scams.

• 17:51David Rosenthal?

  You and Steve Vosniak.

• 17:52Speaker 00

  Yeah. Well, the phone freaking thing was kind of scary because the way Sprint worked in the early days is you just dialed an 800 number and then it asked you to put in like a five or six digit number and then you either got a dial tone or it went eh eh eh eh eh. It doesn't take a genius to figure out if you put up a war dialer, which is just a random dialer on your modem that dialed all these different random numbers. In the morning, you'd have two or three codes. So you start using somebody's code until it got turned off. And so we were doing all kinds of scams and stealing floppy disk and selling chess master. Anyway, I got out of all that and I just went into IT. And so I worked in the computer lab at Fordham. I was making $2.50 an hour, which was the minimum wage in 1987, I think. Then I went to $3.50. Then I got fired from that job because I had partitioned a hard drive and created a hidden hard drive where I put a bunch of video games and I

• 18:36Speaker 00

  was selling video games and WordPerfect.

• 18:39David Rosenthal?

  So you're entrepreneurial.

• 18:40Speaker 00

  Well, yeah, I was, I was, I was a criminal. I was selling WordPerfect out of the Fordham computer lab and I got busted. And I, then I started selling SPSSX, or whatever that's called, like the 10-disc, like $400 statistics package. And this is like,

• 18:58David Rosenthal?

  Yeah.

• 18:58Speaker 00

  Yeah, this is like a really bad idea because now I'm 17, 18.

• 19:01Ben Gilbert?

  It's starting to get worse than Star Wars tapes.

• 19:03Speaker 00

  It's a little bit worse than the Star Wars. So I stopped all that and I realized I could just make six or seven bucks an hour. Then I went to work for Amnesty International. I started making 10, 12 bucks an hour doing IT. And IT just opened my eyes to like, whoa. And I saw the internet early. I saw modems early. And it really opened my eyes. And then I thought, maybe I'll write a book or whatever. And then I was watching this, this zine movement had, happened. Z-I-N-E. And so zines meant you published on photocopy paper, and you called it a magazine. And in Tower Records, they had a section for zines. And I used to go there, look at these crazy zines. And 2600 was one of them. In 2600, they would just self-print it, self-publish it. And it was just hacking stuff, right?

• 19:41Ben Gilbert?

  Is that named after like 2600 baud?

• 19:44Speaker 00

  Yeah, Hertz. Yeah, I think it was Hertz, which is, I think, the, when Captain Crunch made the whistle, that would then give you dial tone. I think it was the 2600 Hertz. We can look it up online while we're here. But anyway, they used to always meet in Manhattan in the city, the Citibank building in the lobby where the phones were. And there was this sort of culture in New York of hacking and media at the same time. And I started a magazine called Cyber Surfer about dial-up, because somebody had told me that Starlog and Fangora, that magazine, wanted to create a magazine about CD-ROMs and dial-up. So I started Cyber Surfer magazine, which nobody knows about. And I got in a fight with the publisher after five issues. He sued me because I had trademarked the name. He didn't know I trademarked the name. I had no contract with him. I was 23 years old. Whole thing

• 20:27Speaker 00

  blew up. And then I was like, the Silicon Valley thing is going to become something. So I started Silicon Valley Reporter as a 16-page photocopy. And Fred Wilson bought the first ad in it, along with Jeff Dodges from Razorfish.

• 20:38David Rosenthal?

  No way. For, he bought an ad for Flatiron?

• 20:41Speaker 00

  For Flatiron Partners, $250. And he bought four ads at once. So he gave me $1,000.

• 20:47David Rosenthal?

  Wow. Advertising like their services as a

• 20:49Speaker 00

  He just put the logo, Flatiron Partners. And this is 1995. I got two people to give me $1,000. I printed it out. It cost $2,000. And I just started handing it out at parties. And I didn't understand how silly I looked, walking around town with a luggage cart.

• 21:06Speaker 00

  Like I was like a street salesman with a stack of photocopies and I would drop them off at everybody's offices because once I got like a thousand copies of this, I didn't have the money to ship it anywhere. So I would go to Razorfish's office. I would go to Site Specific. I would go to iVillage. I would go to all these places and ask them if I could put 20 copies in the reception area and they'd say, sure.

• 21:24David Rosenthal?

  So you're going to these early internet companies?

• 21:26Speaker 00

  Dropping it off. And they would say, oh, you're dropping it off. And I'd say, yeah, I'm the delivery boy. And they'd say, oh, that's very cool. I said, I'm also the editor. And there was a joke in the magazine. I put CEO, editor, and delivery boy on the top. And what it was, was it was like quite charming to people that I believed in it so much that I would carry it with me. And then people also thought I was like, this is why when people say like they think I'm a huckster or a hype man or a fraud. People thought that back then because I would go to parties with a stack of them in my hands. And I'd be handing them out to anybody who would take them. Because I just wanted to be famous. I just wanted to be powerful. I just wanted people to know my name.

• 22:03Ben Gilbert?

  It's so interesting because it's so akin to the early days of blogging. I mean, it's just analog blogging where the, I'm sure any real publisher was looking at this like, oh, it's some kind of joke. I can't believe you're calling yourself a zine. Like, it's not a magazine. You know, this is like

• 22:16Speaker 00

  This is literally what people said to me. And I said to them, no, I have a full page photo on the cover. That's what makes it a magazine. And they said, no, it's a newsletter. I said, no, newsletters have text on the cover of the magazine. This has a full page photo. And then a guy named Carol Martesco emailed me, because you saw the email in there. And he said, hey, I do this magazine called Res and I do this filmmaker magazine. He was doing filmmaker magazine, etc. And he knew how to do magazines. And he was like 10 years older than me. And he said, I can print this on real magazine paper for you. And I said, how much will it cost? He says, it's going to cost $30,000. And I said, well, I have like 20,000 in ads now. It's by the fifth issue. And he said, don't worry about it. I can put it on my credit. I know the person. He printed it for me. Just for free,

• 23:00Speaker 00

  just to do it for me. And then he's like, do you have the money? You have to pay the printer. And I was like, yeah, I got to collect the money from the advertisers. And so then I went around and just asked people to give me the money. And I would bring them two or three grand. Thank you, Carol Martesco. Shout out. I was still friends to this day. And he basically mentored me on how to do that. And then, at a certain point, my assistant, Linda Miller, said, Jan Wenner called.

• 23:22Speaker 00

  And I said, okay, so yeah, you know, from Rolling Stone. And I was like, yeah, it's like year two of the magazine. And I was like, okay, great. And then I went to lunch and then she came back. Did you call Jan Wenner back? And I was like, no. And I was like, I'll call him tomorrow. I come back the next day and she goes, did you call Jan Wenner back? And I said, I don't want to do any press right now. And she goes, no, no, he's not a journalist. Jan Wenner created Rolling Stone. And I said, oh, he wants to meet with you. And so I went up, I met with Jan Wenner, and he had all my magazines on his table. And he said, hey, I want you to come work for me and do a magazine with me. I want to do like a digital version of Rolling Stone. And I said, no, I want to do my own thing. And I was up in his office, and he had marked all the pages.

• 23:59Ben Gilbert?

  But Jason, wouldn't that have made you famous? Like, why wouldn't you do that?

• 24:02Speaker 00

  I also realized, I know, realized I would be a number two. And I never wanted to be number two.

• 24:08Ben Gilbert?

  So it's about the fame and the power, or it was in this era?

• 24:11Speaker 00

  All that. Fame, power, money. Fame, power, money. That's all I wanted. I just wanted to have fame, power, money. All of those things. And I just like, number two? No. And then all of a sudden, I became the king of New York, because the internet hit. Magazine went to 75 full-time people, $12 million in revenue. I built it off my credit cards. I was on Charlie Rosen, I was on the cover of the New York Times. And in three, four years, I went from being a nobody, to writing for Paper Magazine. And when I would walk into any club or whatever, people knew what Silicon Eye Reporter was. And I could get into any party. And then I made a list and ranked the top 100 people in the industry, and I ranked it, just to tweak people. And then people would beg me to move up 10 rankings. And I got everything I wanted.

• 24:48Ben Gilbert?

  Power, the money. The list is still doing that to this day.

• 24:51Speaker 00

  Yeah. And I did my first event in 1995 called Ready, Set, Pitch. And you can look it up in the New York Times, there's an article about it, Ready, Set, Pitch. And it was just, I asked people to pitch their best idea for a startup. And Ted Leonsis gave the keynote. So it was pretty funny.

• 25:06David Rosenthal?

  As you're getting all this, this power, what's going through your mind? Like, are you, are you already starting to think about?

• 25:13Speaker 00

  More.

• 25:14David Rosenthal?

  Are you thinking about, I probably lay this into investing, or I probably X, or like, what's?

• 25:19Speaker 00

  I want it to be the next media mogul. I wanted to be Eisner. I wanted to be like Iger. I wanted to be

• 25:26David Rosenthal?

  Ovitz.

• 25:27Speaker 00

  Ovitz. I wanted to be somebody like that because media was the power back then. It wasn't really about the tech companies. The tech companies were kind of like

• 25:35David Rosenthal?

  This is AOL. This is Time Warner days. This is

• 25:37Speaker 00

  Yeah, you know, like, that's what I wanted to be. I wanted to be one of those media executives and be the CEO of a giant media company. Barry Diller, someone like that.

• 25:46David Rosenthal?

  So you end up selling Silicon Valley Reporter to Dow Jones, right?

• 25:49Speaker 00

  Yeah, it kind of collapsed and we wound up selling. I got two years of salary, but the year before Alan Mackler from internet.com had offered me $20 million for it. And I owned like 85%, 90% of the company. So it was like the one of the most difficult times of my life because I had my chance to be rich and then I was poor again.

• 26:07David Rosenthal?

  Was it the dot com crash?

• 26:09Speaker 00

  Yeah, the dot com crash and then 9/11 and I was there for 9/11. My brother's a firefighter. We didn't know where he was. That was his second fire he ever returned to. So it was a very scary day for me. You know, after 9/11, I was kind of left with this, oh, everything is a fraud. Everybody thinks I'm a fraud. Everybody thinks I got lucky.

• 26:28David Rosenthal?

  You had all this power.

• 26:30Speaker 00

  And it was gone. It was gone.

• 26:31David Rosenthal?

  Did it disappear? Did it really disappear?

• 26:33Speaker 00

  Well, you know, it really was trying for me because everything I had done had gone up and to the right and everything I touched turned to gold. And then when you have the Midas touch and then you start touching stuff and nothing changes, it really is humbling. It's literally like you go from feeling like you're Superman and then you can't fly. And you're like, what's going on? Is there kryptonite in my shoes or something? And it was a very humbling experience for me and it made me really angry. I remember vividly, I just felt very angry at the world and at myself for not taking that 20 million.

• 27:06David Rosenthal?

  So it wasn't just angry about what was happening. It was like you were specifically like angry about passing on that deal.

• 27:11Speaker 00

  I was angry at passing on that. I was angry that the market collapsed. I was angry about 9/11. I was just angry about everything. But I also had skills at that point and confidence. And so I said to myself, I am coming back and I'm going to come back. I'm going to dunk on everybody. And I will show everybody that not only am I not a fraud, that I can do this again and I can do it quicker, faster and better. And I started looking for an idea and I was studying and studying and studying and two people who worked for me after the whole thing collapsed had moved on and started blogs. And they were doing really well with their blogs. And one of them was Rafat Ali, who's doing, who's doing this paidcontent.org. And I had admonished him because he started it when he was working for me. I was like, listen, kid.

• 27:52David Rosenthal?

  I didn't realize Rafat worked for you.

• 27:54Speaker 00

  Yeah, he was one of my writers. I think that was his second job. He had, he had worked for Inside.com and then for me. And he had owned the Inside.com domain at one point. So there's a whole story of history there of who got to own Inside.com at the end of the day. I can tell that story too at the end, but anyway, I was like, and then Shenny Jardine went to work at Boing Boing. And I found out they were both making like four or five grand. And I was like, wait a second. That's like, kind of what I, that's more than, I think that's more than what I was paying you. Per month, per month.

• 28:21David Rosenthal?

  Just on ads on their blogs.

• 28:24Speaker 00

  Exactly. So I was like, wait a second, these people are working in their underwear. They have no editor and it dawned on me, the right writer and editor is a hindrance. They're taking out what's special about what the person said. This is like taking out the production. It's like Bob Dylan just on stage with a guitar. It's better when it's not produced. It's better when it's acoustic. And there was that thing that was going on. MTV had Unplugged. And I said, this is MTV Unplugged for journalism, blogs. It just clicked in my mind, clear as day. When you saw Kurt Cobain on MTV Unplugged, you wanted to throw the other records away that were studio produced.

• 29:09Speaker 00

  And I said, blogging is going to be a thing. So I started looking for other blogs and this, I knew this kid Nick Denton, who had started First Tuesday. And he started Gawker. I said, hey, Nick, you know, want to have lunch? Went for lunch. I said, I'm thinking about doing a blogging thing. I think this could be big. If somebody did it for business, it would be huge. You're doing this Gawker gossip thing. I'm not interested in that, but if somebody did a business version. And then he wrote a blog post and he said, the worst thing that could ever happen to blogging is Jason Calacanis bringing his unique brand of like whatever to it.

• 29:37David Rosenthal?

  Corporate sellouts.

• 29:38Speaker 00

  Well, that's what he said. Cause I was like, you know, this would be an advertising juggernaut. Cause think about it, you get rid of all of the, you get rid of like 80% of the staff. You just have the one great writer and one great salesperson. Did Valley Wag exist at this time yet? No, no, no, no, no. Valley Wag he created much later. It was just Gawker.

• 29:54David Rosenthal?

  I mean, like I've worked at the Wall Street Journal. I mean, you did too for a while, like there, you know, it's a wonderful organization. There are a thousand people in that building.

• 30:01Speaker 00

  Yeah.

• 30:02David Rosenthal?

  Like, you don't need that to.

• 30:04Speaker 00

  No, you don't need a building. Yeah, you don't need middle management. I mean, you don't need anything. So I was really taken by, you know, Denton's vision for this. And I was like, are you gonna do more? And he's like, yeah, we're doing this. We're gonna do a political one, I think. And we're gonna do this one on gadgets. Like, you know, like the fetish thing in Wired magazine. We're gonna just make that into a whole thing. And I was like, oh, that's interesting. So he writes his blog post trashing me. And I was like, you... And so, you know, like, I'm a pretty aggressive guy. And I was like, so my partner, Brian Alvey, who I convinced to do this with me, this 2003, none of us had any money. We're doing it all for free. The economy was flatlined. I said, I'm gonna destroy him.

• 30:46Ben Gilbert?

  Which it turns out, you were not the last person to have that thought.

• 30:49Speaker 00

  No, no, no. I was not the first. I was, it might have been the first, but not the last. I said, I have to destroy Nick Denton. How am I gonna do this? And I said, oh, I know, talent. There's nothing worse than losing talent. Elizabeth Spears, she's writing Gawker. I'm gonna make a run at her. And I had heard that he was paying the writers $1,500. And the MacBook Air had just come out. I contacted Elizabeth and I said, let's have coffee, whatever. And she agreed to have coffee or something. And there's like a photo of it, actually, of me talking to her at a bar that somebody took in the early days. And she's looking at me like I am the Antichrist. And I was like, you are a unique talent. Nick Denton will never give you equity. I will give you equity. You will become a millionaire. I'll

• 31:34Speaker 00

  give you a MacBook Air, and I'll give you two grand a month, which is a 33% more raise. She was like, yeah, no, I'm gonna go work for New York Magazine. And I was like, that's the worst career move you could ever make, Elizabeth. Magazines are gonna die. Blogs are gonna take over. There's no way magazines can ever keep up with blogs. Whatever they print is gonna be old news. And you're already proving it. You're number one at blogging, and you're gonna become number 500 out of magazine. So she wouldn't do it. And then Shenny Jardin said to me, oh, you picked the wrong target. I was talking to her, because I was trying to recruit her. And she's like, no, no, I love this boing boing thing. I don't want to do anything commercial. And I was like, all right, that's fair enough. I was like, who should I target? She goes, oh, you picked the wrong target. I said, what do you mean? She goes, oh, Nick's not making any money on Gawker. Gawker doesn't make

• 32:16Speaker 00

  any money. It loses money. I was like, okay, tell me more. She goes, 100% of the revenue's coming from Gizmodo. I said, oh, okay. He goes, do you know Peter Rojas? I was like, yeah, I've heard of him. That's the one you want. So I went to Peter Rojas and I called this guy I knew was running Jewel Baku, which was like a fancy sushi place in Lower East Side. And he was the owner and his wife and it was like a pretty hot ticket. And I asked Peter to come have sushi with me. And his wife, Jo, or his girlfriend at the time, she says, can I bring my girlfriend? I said, of course. We go there and I'm prepared to like knock their socks off with this omakase. And I said, you guys have anything, you know, terms of like Thai? And they're like, well, we're vegans.

• 33:02Speaker 00

  I said, okay, yeah, that's no problem. I said, give me one second. I go back to the guy. I said, listen, I'm trying to close this deal. It's really important. Like they're vegans. He's like, don't worry about it. I'm right back. He runs to the Korean grocery in the store. He comes back with two big shopping bags full of things and he makes them the most amazing omakase with vegetables.

• 33:17David Rosenthal?

  Wow.

• 33:18Speaker 00

  And so I said to Peter, I said, Peter, you know, Nick Denton is a bad actor and equity is what you need. And if you join me and you create a Gizmodo killer, I'll give you equity in the company and you will become a millionaire and we'll be in it together. You'll be a partner. And he goes, well, Nick said he's going to give me equity. I said, he'll never give you equity. When did he tell you that? He said, he told me that like six months ago. I was like, yeah, how's that going? I said, I will give you equity on day one, fully vested, everything, just like me. And he said, okay, let me think about it. And he came back and he said, okay, I'll do it. I said, great. He said, but you know,

• 33:56David Rosenthal?

  This is so great. Because by the way, at this point in time, this is, I'm probably seventeen, eighteen, nineteen years old at this point. I'm reading Gizmodo every single day and I always wanted to know what happened. How did Engadget become? But I never knew. Like,

• 34:11Speaker 00

  Yeah.

• 34:11David Rosenthal?

  This is the story.

• 34:11Speaker 00

  And he says, oh, my girlfriend, Jo, made a logo and Jo made the first Engadget logo. I was like, great. He said, can we pay her for it? I was like, sure we can. And I was like, what does she charge for a logo? And he's like, 300. I was like, give her 500. It's fine. Because Mark Cuban had given me $300,000 for 15% of Weblogs Inc.

• 34:29David Rosenthal?

  How'd you get to know Mark?

• 34:30Speaker 00

  I had no Mark because I had written Broadcast.com is a billion dollars worth of hot air and so I can hire a reporter and he

• 34:37David Rosenthal?

  He reached out to you.

• 34:38Speaker 00

  Blew a gasket. And I said, well, your revenue is like 10 million. He's like, do you know what the revenue is next quarter? I was like, no, you're a publicly traded company. Of course I know. And he's like, well, why don't you wait? And then revenue went from 10 to like 60, you know, like quarter over quarter. And I was like, okay, it's not a billion dollars in hot air. And I did a Mia Koopa kind of situation. And we became good friends, Mark and I, for a long time. And he put 300K in. We started Blog Maverick for him. Brian Alvey came up with the name. Brian Alvey came up with all the good names. The best collaborator I've ever had in my life. And Peter. And so Peter said, listen, you know, I just, I feel really bad about the stuff with Nick Denton. I was like, you shouldn't feel bad. This guy promised you equity and he gave you nothing. And you've given him this incredible brand that's going to become worth millions of dollars. You should feel zero guilt. He robbed you of your vision. And we're going to take it back. And he's like, yeah, yeah, maybe

• 35:23Speaker 00

  you're right. And I was like, yeah, because listen, I've been in fights. And, you know, if somebody takes a swing at you, like somebody gets a, if somebody sucker punches you, you have to teach them a lesson. So they don't do it again. Because if you don't teach them a lesson, what I learned is they will come back. It has to be such a beat down. It has to be so painful that the person says, I should have never punched that, I should never sucker punch that guy. That's how powerful the beat down has to be. It can't just be retribution of one for one. If they punch you, you have to annihilate them. This is what I learned about violence when I was growing up. And I've since disavowed this.

• 36:06Speaker 00

  But this is literally what I saw on the streets of Brooklyn in the 70s and 80s. So I said, when are you going to tell Nick? And he said, well, he's, you know, he's been working so hard for like a year and a half or whatever. And he's just burnt out. He's been working seven days a week on this. And he said, he's going to take his first vacation. I said, oh, really? He's like, yeah, yeah. And he's going down to Brazil or whatever. And all these famous people are going. I was like, when is he going? He's like, he's going Sunday. I was like, oh, what time is he leaving? He's, I don't know what time he's leaving. I said, okay. And I looked up online, like flights to Brazil, whatever. Couldn't kind of figure it out. And I was like, all right, well, listen, I want you to write a blog post about this. We're launching the site at 2pm on Sunday. And we literally launched the site the first day of his vacation. He landed with his people going Gizmodo has no blogger. We have all these advertisers and this is a competitor.

• 36:55Speaker 00

  And that was the approach I used to take to competition. I don't do that anymore. But, well, by the way, and the postscript to that is Denton and I became very good friends after that for a long time and still are. And I consider him one of the, just the great publishers. But you can't graze over that. So how?

• 37:08David Rosenthal?

  Yeah, yeah.

• 37:09Speaker 00

  How do you become friends with someone after that? Oh, he reached out. He reached out afterwards. He wrote a blog post actually saying, you know, Jason really stuck it to me, but we're, we're going to be great competitors. And then I launched Joystick and then he launched Kotaku. Then I launched Autoblog. Then he launched Jalopnik. And when we were head to head, we always had three, four, or five times the traffic is him. But it created this rivalry that everybody followed. It became Coke Pepsi. It became, you know. Oh, yeah. Pick media company versus media company. And, and everybody was following this great competition between this brash Brooklyn kid and this aloof, you know, quietly-

• 37:43David Rosenthal?

  It probably made you, made you both better, right?

• 37:45Speaker 00

  Oh, it made us incredibly much better. But, you know, it was like, literally this like quietly gay, you know, very understated Brit versus this brash Brooklyn bulldog. And it just played really well in the press. And you can, if you type Denton Calacanis into Google and look at some of the posts from back then, it's hilarious. And it was just a good time. But he reached out to me and he said, listen, I think we should have a, you know, Jason, respect, respect for what you did there. I understand, you know, Peter, best of luck with Peter. And, you know, we went for, have coffee, whatever. And we're sitting there and he said, I have a proposal for you. And I said, yes. He goes, I think that, you know, if we're going to have this spirited competition, that's great. You know,

• 38:27Speaker 00

  good for the game and all that. And you're, you're a worthy competitor. And obviously you've been able to-

• 38:33David Rosenthal?

  You're just waiting for the knife to come out, right?

• 38:35Speaker 00

  Well, yeah. And I'm just like, okay, this could escalate. Yeah. And he said, I'm proposing a no poach agreement. And I said, what does it mean? He goes, well, just, you know, there's no need, there's so many writers out there. We're, we're not enemies. What we're fighting against is the magazines and the newspapers. You know, we're, we're up against the New York Times and, you know, that's enough competition for us. And I, and I said, you know, that, that makes a lot of sense. So we will, we agreed to not poach each other's writers.

• 39:01Ben Gilbert?

  All right, listeners. Now is a great time to thank our longtime friend of the show, ServiceNow. If you are running a large enterprise, AI agents are likely spread across every team and deploying them is no longer the hard part.

• 39:15David Rosenthal?

  Yeah, the hard part is knowing what permissions they have, what employees are using them for, or what decisions AI is making. AI security for an enterprise at scale is not a small concern. Like, the risks are real.

• 39:29Ben Gilbert?

  Exactly. And the challenge with AI is governing it, securing it, measuring it, and making sure that it actually delivers value. That is why ServiceNow built the AI Control Tower.

• 39:39David Rosenthal?

  Yep. AI Control Tower gives enterprises a single place to see, manage, govern, and optimize AI across the entire business. And it works with any AI, not just theirs. Every device on your network, every permission across every system, every AI agent visible and secure in one place.

• 39:57Ben Gilbert?

  And ServiceNow can do this because they've spent more than 20 years building the operational backbone of the enterprise. The workflows, governance, approvals, security controls, and institutional knowledge that power how work actually gets done across IT, HR, customer service, finance, and security.

• 40:13David Rosenthal?

  ServiceNow already runs more than 100 billion workflows annually and trillions of transactions for more than 85% of the Fortune 500. So when companies need a place to govern AI at enterprise scale, they're building on a platform at the center of how their business already operates.

• 40:30Ben Gilbert?

  And in a future that isn't going to be one AI, it's going to be thousands of AI agents working across every function of the company. But the question is, who's managing them all?

• 40:39David Rosenthal?

  So if you're trying to turn AI ambition into real business outcomes and make it work safely, securely at scale, go check out servicenow.com/acquired and tell them that Ben and David sent you.

• 40:50Ben Gilbert?

  Well, Jason, I got to tell you, just a quick personal note, and this will surprise zero longtime listeners of the show. Like, I think the number one website that I checked every single day at high school was the unofficial Apple weblog.

• 41:00Speaker 00

  Tuaw.

• 41:02Ben Gilbert?

  Yep.

• 41:03Speaker 00

  There's an interesting story to that. We called it the Apple weblog and Steve got upset.

• 41:09David Rosenthal?

  No way.

• 41:11Speaker 00

  Yeah. And we got a phone call and I said, okay. We actually had called it the unofficial Apple weblog and Apple called. Steve told his people to call. We had a pretty close relationship with Steve, or at least Peter did. And, you know, Steve responded to our emails.

• 41:26David Rosenthal?

  Steve always realized the power of the media.

• 41:28Speaker 00

  Well, yes. I mean, Steve was the master and I'd spoken to Steve in person two or three times and over email. You know, half dozen times during the Engadget time. Peter, much more. He really loved Peter. And Steve was really great. And anyway, they had some sort of problem with it and they said, you can't use Apple in the name. And I said, okay. And I just said, you know, it's back when you could buy domain names. And I said, the unofficial Apple weblog. I said, this should make it an acronym, TOA, and then just build a logo. And I think Jill Fahrenbacher, you know, Peter's now wife, mother of his kids. I think she built that one as well. Took the little leaf of the apple and just threw it above the TOA and called it a day. Well, that was kind of, I think that was Brian Alvey's joke is like, it sounds like it's French. So let's put it as like an accent de grave on top of it.

• 42:12Speaker 00

  And I was like, sure, let's troll them. And we just like a lot of crazy stories like that. And long story short, that company lasted 18 months. We got, we sold it for $30 million to AOL. This is all of Weblogs Inc. This is all these. All of Weblogs Inc. We had $100,000 in revenue to date and probably 200,000 looking forward. So depending on how you count that, they paid three, they played a big multiple.

• 42:36David Rosenthal?

  But, but the real question though is like, looking back now, was that actually a good idea to sell?

• 42:42Speaker 00

  Of course. Yeah. I mean, if you, that gave me the money to become dangerous and it gave me that foundation, you know, when you get that, you know, the first 10 million is the hardest. And once you get that on your belt, you're dangerous. Nobody can stop you. I mean, I was already dangerous because I didn't care, but once you get the cash, then you really have the ability to not care.

• 43:01David Rosenthal?

  Right. So it's like, if you hadn't sold and now we're still an independent company, that would be worth a lot more money.

• 43:07Speaker 00

  I mean, listen, here's the joke. Denton wound up selling, I think for 150 or something like that. And then half of it went to this new company that had put in the bridge financing and then some amount went to Hulk Hogan and Peter Thiel. And then some amount got left over. I think we wound up netting about the same. It just took him 12 years. It took me 18 months.

• 43:26David Rosenthal?

  Right.

• 43:27Speaker 00

  But, you know, you know, what I was.

• 43:29David Rosenthal?

  You got to start writing your next chapter.

• 43:31Speaker 00

  Exactly.

• 43:31David Rosenthal?

  And you're back in the game.

• 43:32Speaker 00

  The thing is, I had what the, the, the great thing about Silicon Alley Reporter crashing and burning was I learned very early on that I was more than the brand. Cause the brand Silicon Alley Reporter had gotten so big and I was so identified with it. That I started, people would call me the Silicon Alley Reporter. That was like what people would refer to me as. And because it crashed and burned, I was forced to disconnect myself from that. And I, Bob Dylan was always my favorite artist. And I had always studied and been obsessed with how he went from like folk to electric and rock

• 44:09Speaker 00

  to gospel and this, yeah, he just kept reiterating. And then he started collaborating with Mark Knopfler of Dire Straits. And did Empire Balesk and, you know, all these other really infidels and these very interesting albums. And I'd seen Bob Dylan maybe 20 times, um, you know, in person and he was, you know, always my favorite. And I was like, don't look back. And I just told myself, you cannot look back. And I, I never look at my press clips, the amount of press I got in the nineties. Between being on Charlie Rose, being on 60 Minutes, all that stuff. I knew that I was never going to top that. You know, like that was a moment in time and I didn't want to top it. Who cares? Like I, I put all that press in boxes. I taped it up.

• 44:50Speaker 00

  And it's literally in my brother's garage in New York still. I don't want to ever look at those clips. Don't look back. Only forward, next brand, next brand, next brand. Don't worry about the last brand. Yeah. And that's how I looked at myself at that point. I, I looked at myself and I said, you know what? Kurosawa did all those Samurai films and then he went into noir and the noir stuff was better. And nobody even knows about the noir, you know, the film noir stuff he did, High and Low, Shrey Dog, you know, all this kind of stuff.

• 45:19David Rosenthal?

  Is it after then, the next chapter, you get, you get money, you're back in the game after?

• 45:26Speaker 00

  I'm in the game, baby.

• 45:28David Rosenthal?

  Is that when you moved to LA?

• 45:30Speaker 00

  I had been living in LA when we start, uh, right after we started Weblogs Inc. Yeah.

• 45:36Ben Gilbert?

  And at this point, do you still want to be famous? Like, once you've adopted this mentality of don't look back, are you still fame driven?

• 45:43Speaker 00

  No, fame wasn't. I really wanted to build things. I had gotten into the mode of building. Not necessarily empire building.

• 45:51David Rosenthal?

  Hanging out with like Silicon Valley types?

• 45:54Speaker 00

  I think it was. I think also when you get the win under your belt, it takes the edge off. And I always tell that to young founders, like, you know, winning really takes the edge off. And you will be successful. It may take two or three companies. You know, if 60, 70% of these things fail, don't worry about it. Just start three or four, you're going to have a hit. And nobody remembers. Like, we're sitting here, when people meet me, they don't know what Mahalo is. They don't know what Silicon Eye Reporter is. They don't even know any of this stuff. Nobody has any sense of history. But people are all caught up in their own history.

• 46:22Ben Gilbert?

  I for sure had a Mahalo account.

• 46:24Speaker 00

  Yeah, I mean, Mahalo did really well. I mean, that's a whole nother story, but yeah. Now, that's another one, right? Where you just, you build a brand that becomes so big and you kind of get associated with it. And then you have a big flame out and it's like, who cares? Just move on, next one.

• 46:39Ben Gilbert?

  We'll get there, but I do want to talk about the Mahalo pounce Twitter, that sort of Tumblr. Like, let me put a pin in that. And David, keep running with your line here.

• 46:50David Rosenthal?

  Well, okay, so this is, this is a diversion, but we sidetracked, but we got to cover it. When you're in LA, how do you meet Travis Kalanick?

• 46:59Speaker 00

  Well, I, when I was doing Silicon Eye Reporter, we had started an addition called Digital Coast Reporter. And I had interviewed Travis when he was doing Scour, which was his first company.

• 47:09David Rosenthal?

  Oh, wow, yeah. Which was sued and...

• 47:11Speaker 00

  And he got sued and all that stuff. And he told a famous story. And that was the night, allegedly, when Michael Ovitz's people came and were in the audience at my event. I used to do a CEO interview and I interviewed him. So that was that famous story. And then he did Red Switch. We'd always been friends and we'd always liked each other. And that's how I wound up investing in Uber, because when he was raising money for it, he wasn't going to be the CEO. Uh, he was like, hey, I'm doing this company. It was like a, you know, Ryan and him and

• 47:36Ben Gilbert?

  And Ryan was CEO?

• 47:38Speaker 00

  Ryan was gonna be CEO and then I was gonna invest a little bit of money and I was helping Ryan raise money. And then he said, you know what? I'm gonna be the CEO. I said, what happened with Ryan? And I was like, oh, this is a little shaky, whatever. And then I just made it as the first scout bet and I introduced, I think, First Round and definitely Cyan. We're at the Open Angel Forum, the little event I used to start where I matched angels and

• 47:58David Rosenthal?

  So at this point, you're, you're running Mahalo at this point?

• 48:00Speaker 00

  Yep.

• 48:01David Rosenthal?

  So I didn't, I didn't really, was Uber the very first scout investment?

• 48:05Speaker 00

  I think it was the third. I think I had, I had, in the first seven, there were three unicorns.

• 48:11Ben Gilbert?

  And this is Sequoia Scout?

• 48:12Speaker 00

  As a Sequoia Scout, I, I had, in the first seven, Uber, Thumbtack and Data Snacks. So three companies, three unicorns, one of them public, Decacorn. We'll see about the other two, but I think the other two got a chance to go in public too.

• 48:27Ben Gilbert?

  And so our, our listeners understand here, and we didn't list all the companies that you've angel invested in, but we're gonna keep touching on them as we go. Like, so when you're investing as a scout, that's not your own money. So how did the economics work on that?

• 48:38Speaker 00

  It was 50/50.

• 48:40Ben Gilbert?

  So it's 50/50, basically splitting the carry, the profits off that investment?

• 48:44Speaker 00

  Yeah, split the profits, yeah. Yeah, it's crazy. They since dropped it, I think to 35 or 30, like a normally high carry.

• 48:52David Rosenthal?

  How did this happen though? Like what?

• 48:54Speaker 00

  Well, Ruloff called me.

• 48:55David Rosenthal?

  Did you go to Ruloff or did Ruloff come to you?

• 48:56Speaker 00

  I had lobbied Sequoia, I had emailed Sequoia and lobbied them to invest in my friend's poker game, Zynga Poker.

• 49:05David Rosenthal?

  Wait, wait, wait, you invested in the poker game?

• 49:07Speaker 00

  My friend created a virtual poker game, Mark Pankas, called Zynga. And our dog used to play that kind of game. And I invested, I said, hey, you should invest in this and they, they couldn't get there. But my, but my other friend, Fred Wilson

• 49:21David Rosenthal?

  You were a portfolio entrepreneur.

• 49:23Speaker 00

  I was a portfolio company and I said, hey, you know, this Twitter thing's gonna be big and this Zynga thing's gonna be big. And I was pushing Ruloff and I have an email where I told Michael Moritz and you have to get the Twitter deal. You have to get the Zynga deals. These are very important companies.

• 49:38Speaker 00

  And then my friend Fred Wilson

• 49:39David Rosenthal?

  What did they say?

• 49:40Speaker 00

  They, they, I said, they went the next day actually and tried to close Twitter, but they couldn't get their head around the valuations or whatever it was at the time. I'm not sure their exact objections. Both of those cases, Fred Wilson had invested and actually introduced me to Mark Pankas. And Mark Pankas and Evan Williams and I were talking Sequoia or Fred Wilson. And I was a Sequoia CEO and I said, listen, when you are a Sequoia CEO, your phone rings off the hook, everybody wants to do your Series B. I raised my Series B from a hollow before launching the product, six months after I had raised my Series A. And I went from an $11 million valuation to $100 million valuation.

• 50:14David Rosenthal?

  Wow. And this is in 2006?

• 50:17Speaker 00

  Yeah, 2006, yeah. And Mark Pincus and Evan were like, how did you go from $11 million to $100 million before the product launched in six months? I was like, I don't know. And they were going for like 30 or 40 million, I think each. And they were further along and their products were launched. I said, listen, Fred Wilson's East Coast, he's awesome. He's like one of my best friends for a long time. He got me, helped me get in business. His wife, Joanne, worked with me at Silicon Reporter as a salesperson. And, you know, and also Joanne Wilson, his wife, worked with me at Silicon Reporter. And the reason it was so successful is she was the salesperson and she was, like, I mean, it was, it was two Bulldogs. Like, she's a tiger.

• 50:53Ben Gilbert?

  And she's now a great angel investor herself.

• 50:56Speaker 00

  Absolutely, yes. And, and just one of the great collaborators I've ever had in my career. And anyway, long story short, I said, listen, you're picking between Fred, who's like the up and coming hustler, who will work hard, and, but, you know, he's, he's East Coast. And a lot of people, you know, are, you know, Fred thinks Sequoia is the gold standard. Fred would tell you to take Sequoia's money. But I think Fred is great too. So I actually think it's a coin toss. You can't lose. And they were both struggling to take, which, who would take that deal? I think that gave me the credibility with Sequoia, that they said, Jason keeps sending us these great deals. There's many more companies now. Jason has this collaboration with Arrington for TechCrunch50 and they

• 51:39Speaker 00

  broke up and now he's doing this launch festival on his own. Ruloff came up this idea, what if we raised like a 3 million, $2 or $3 million fund and we just gave everybody the ability to make 25, 50K checks? And there was this issue of signaling in the industry back then, where if Sequoia gave you money and they didn't give you the next round, your company was dead. That was the end of your company because you were then-

• 52:00David Rosenthal?

  Obviously, the trick is do what you did and just raise your next round before anything even happens.

• 52:03Speaker 00

  Well, that works too. But you know, the idea is like you would, if your venture fund did not follow on, you were damaged goods and nobody else would. And the higher profile of the fund, the higher profile of the signaling risk. So Sequoia was acutely aware of this. So they just said, the Scott's program, we won't announce, it'll be on the DL. You can tell people what it is when you make the check. You don't have to, you can. We just weren't sure what to do. And so I just went around town and I said, okay. I started this thing, Open Angel Forum, and I tried to kill something called Kretzsch for him, which was charging people $5,000.

• 52:32David Rosenthal?

  Yeah, I remember.

• 52:33Speaker 00

  So I went to war with them and they got really upset and called Michael Maritz on the phone and told him like, who is this employee of yours? He's like, not employee of ours. Well, he said, he's going to kill the, he's going to kill the Kretsch for him. And he's like, why would he say that? And Maritz called me and he said, did you, Jason, did you tell them you were going to murder them? I was like, yeah.

• 52:53Ben Gilbert?

  You really love these situations where you take a mild mannered Brit and you really anger them in a way where they have to have a talking to.

• 53:00Speaker 00

  No, no, Michael Maritz was not angry. He's like, why would you tell them?

• 53:03David Rosenthal?

  He probably loved him.

• 53:03Speaker 00

  Just curious. And Maritz is cool as eyes. He's the greatest. And I said, well, they're charging founders $5,000 to meet angel investors. He goes, oh, that's terrible. I said, yeah. So I want to kill them. He's like, oh, okay, carry on. So that was the end of the phone call. It was great.

• 53:18David Rosenthal?

  So great.

• 53:19Speaker 00

  Oh, so great. So anyway, I started Open Angel Forum and I just started, you know, Thumbtack, StyleSeat, DataStax, all these signposts, all these great companies just came.

• 53:29David Rosenthal?

  And Uber actually pitched to Open Angel.

• 53:31Speaker 00

  And Uber came, yeah. And on the spot, myself. Saka was there, but Saka knew Travis before. And Cyan Banister invested in them. I introduced Cyan Banister to Thumbtack and Uber. She's always been very gracious about giving me credit for that. And in the first round, I think I introduced them, but I think that maybe they claim I didn't, or maybe somebody else in the firm had heard about it as well. Who knows? You know, like, success has a million-

• 53:53David Rosenthal?

  A million fathers.

• 53:54Speaker 00

  Fathers, failures and orphans.

• 53:55David Rosenthal?

  Okay. So all this is go, what's going through your head as this is happening? Like, you're running Mahalo. Mahalo's super high.

• 54:00Speaker 00

  Yeah. I mean, they anointed me. You know, Sequoia anointed me. Now I became dangerous because now I wasn't just East Coast anointed, I was West Coast anointed. You understand?

• 54:09David Rosenthal?

  Yep.

• 54:10Speaker 00

  And nobody really had ever done that. That was a very unique thing. And I knew it.

• 54:15Ben Gilbert?

  I think a lot of our audience probably has not ever heard of Mahalo. So fill us in real quick on that.

• 54:20Speaker 00

  So anyway, I had this idea. I emailed Michael Moritz, John Doerr and Mark Cuban. And I said, I have an idea for my next company. I didn't know any venture capitalists, even through all of this. I really didn't know any of the West Coast venture capitalists. But I knew John Doerr and Michael Moritz were the number one and number two, probably in reverse order. Michael Moritz and John Doerr. But anyways, there's an argument about that. I had run into Moritz one time at like a conference. He wouldn't remember me, but I emailed Michael Moritz and I said, I have my next idea for a company. I sold my last company to AOL for $30 million, 18 months after I started it. Would love to get your advice. Shortest email possible with a little microphone drop in it. And Moritz called both of my phone numbers and emailed me and his assistant called me all within one hour of me sending the email.

• 55:00David Rosenthal?

  I was gonna, I was gonna ask, how many minutes did it take to respond?

• 55:03Speaker 00

  John Doerr, somebody on his team, got me the next day. I was in both their offices next week. And also Mark Cuban said, because I think when we sold, we turned this 150 into five or six million. So he said, put me down for a million or whatever you want, Jason. I think there was actually a second payment coming and he just CC'd his attorney and said, whatever the second payment is for the AOL thing. It was like a million bucks. He said, just throw it into Jason's next thing, which is, you know, very Mark Cuban thing to do.

• 55:28David Rosenthal?

  Okay, so here's the question. Did you actually have the idea or did you just send the email?

• 55:31Speaker 00

  I did, I did have the idea. And my idea was I had gone to, Wikipedia was like the thing at that point in time. And I went to Wikimania, which was like their conference up in Boston. And I studied the Wiki software. I started playing with it and I made a little proof of concept where Google was dealing with web spam at the time. And the order of the links weren't very good. My wife's Korean and I had heard about DAUM, D-A-U-M dot net and comprehensive search in Korea. And in Korea, DAUM owned the blogging company and the picture hosting company. And they, when you did a search, they would show pictures, they show links, pictures and blog posts on one page. And so I made this comprehensive search and I said, it's going to be called 20.com.

• 56:15Speaker 00

  The top 20 links for any keyword. And I went into the meeting and I put three pieces of paper on the table. And I don't think I've ever told this story. And I said, iPod, look at these 10 blue links. These are the search results. One's Yahoo, one's 20.com and one is Google. Which one do you like best? And Maritz and Rulov pointed to the one and they turned it over. I said, turn it over. It's a 20.com. I said, turn the over to over. I did it again. I said, Kawai Vacation. And they picked mine again. And I said, they said, how did you, why is yours the best? And I said, I had a human look at the Google result and make a Wikipedia page. And they said, that's great. And Michael Maritz said, oh, that's a great idea.

• 56:56Speaker 00

  What are you looking to do? I was like, I want $3 million for 25% of the company. And he said, okay, work with Rulov. And he walked out. And he was on the board of Google. And he's like, I can't be on the, I can't do this, but Rulov can. And it's not competitive with Google. It's, you know, whatever. It's a wiki, whatever. That was the start of it. And then my friend Elon put some money in. He was Just casual. Working a rocket company. He just called me. He's like, I think you're smart. I'll put some money in.

• 57:22David Rosenthal?

  You want to diversify out of hardware.

• 57:23Speaker 00

  Rupert Murdoch put some money in. CBS put some money in. Just a bunch of people. And, you know, whatever. I was, I was on the top of my game. Got the company a $10 million in Google AdSense revenue. And then Matt Cutts felt like we were getting too big and eHow was getting too big.

• 57:41David Rosenthal?

  There was also Cosmex, right?

• 57:43Speaker 00

  Yeah, Cosmex, WikiHow. Just, there was a whole cohort of us making content.

• 57:46Ben Gilbert?

  And let's, let's pause for a minute, just, just to catch everyone up on Matt Cutts. So Matt solved a really hard problem for Google over the course of a decade, which was basically link spam. It's how do we stop people who are gaming Google and getting too high in the rankings and getting too much traffic? And abusing us. Yeah. And I think Matt actually is leading a really important initiative now in the federal government at the, um, the US Digital Service.

• 58:08Speaker 00

  Well, what would happen is our pages were so good that Kawai Vacation would rank in the top five. And people would blog about it, link to it, and ask us to update the links. And then we started putting content on the pages. So we had content on the pages. So basically, Google, this was all on their roadmap, but I created was on Google's roadmap five years, 10 years before they got there.

• 58:29David Rosenthal?

  Because if you Google Kawai Vacation on Google.

• 58:32Speaker 00

  You get that now. So I was five or 10 years ahead of them. And they were going to do it machines. Marissa said, I don't think Jason's right. We had this like debate at the, at a conference at one point. Somebody asked her about Mahalo. She said, I don't think humans can scale. What we're going to do with robots. Anyway, then they basically took 90% of our traffic away. And the punchline was they took 90% of their own revenue away because the way we're monetizing was with their tools. And then I said to Matt, and I called up Sergey Brin, and I called up everybody I knew there. And I was like, what are you guys doing? You just killed my site. I have to lay off 100 people. And we got in this big public spat. And they're like, yeah, you know, we don't know. And I was like, well, we're partners. And Matt Cutts was like, we don't have partners. And I was like, I forwarded him the email from the AdSense team that said, partner meeting. And that they, you know, and partner lunch and partner this and partner that.

• 59:17Speaker 00

  And he's like, yeah, that's a different group. I'm like, but you're still Google. And they literally took everybody who would eventually become competitive with them. And they just neutered us. And this is why I think, you know, Google will face antitrust action like they did in Europe. Maybe here eventually. And I think Yelp's right. What they did to Yelp.

• 59:32David Rosenthal?

  Yeah, it's the same thing.

• 59:34Speaker 00

  Was equally bad. I mean, they basically studied us, copied us, killed us. But I mean, I learned a really important lesson there, which is like, don't have a dependency. But the problem was, you know, just think we're so quick. I was like, we're making, we're on, we're on a $10 million runway. We're making just a lot of money every day at the peak in AdSense. And this is all hunky dory. I was like, they'll never shut us off. We're, we're sending, we're giving 30 cents of every dollar to them.

• 59:58David Rosenthal?

  Yeah.

• 59:58Speaker 00

  And I was wrong. You know, they had a long game. They just didn't want mahalo.com and other things to exist. So they killed us. And then I pivoted to Inside. And it's still going today, 12 years later. And, you know, it's, it's actually doing really well for email newsletters. What's old is new again. Exactly.

• 1:00:14David Rosenthal?

  So what's, what's going through your head at this point in time about like, okay, what is your next act? Like, like.

• 1:00:21Speaker 00

  Well, the Scouts thing, I didn't take too seriously. I just thought it was a fun diversion. And then they got about, I don't know, halfway through the program and Ruloff said to me, you know, nobody else is making investments. I think like Sam did Stripe or something. You did Uber and you did four and Sam did two. Sam Altman had done Stripe. And they said, you know, this fund, we might not do another Scouts thing. So, you know, you've got like a million left in the fund. And I was like, oh, you don't have to tell me the buffet zone.

• 1:00:47David Rosenthal?

  Is Uber, Stripe, Thumbtack.

• 1:00:51Speaker 00

  Data Stacks.

• 1:00:51David Rosenthal?

  Data Stacks.

• 1:00:52Speaker 00

  I mean, that fund is the greatest fund in Sequoia's history on a percentage return basis, I believe. I don't know that for sure. $30 million. Not on cash though, not on cash, on multiple on cash.

• 1:01:03David Rosenthal?

  On multiple.

• 1:01:03Speaker 00

  On multiple cash, it's definitely in their top five, I would think.

• 1:01:06David Rosenthal?

  But they're saying to you, we don't know if we're going to do this again.

• 1:01:09Speaker 00

  Well, it was very early days. We didn't know. And they're like, we still have all this money left in the fund. So Ruloff was like, if you want to make some more. So I did 19 investments. I put 700 to work. It became worth over 100 million in total, largely due to what, an Uber. And then my friend Naval had been coming to. The Open Angel Forum, because he was doing venture hacks and he was an angel investor. And he said, listen, I'm going to start this thing Angel List. And it's kind of competitive. So I was like, no, this is, you're doing online. Online is dumb. You know, like, nobody's going to invest online. It's all in person. And he's like, yeah, I disagree. And I was like, yeah, I don't, I don't know, Naval. I don't think, I don't see anybody investing blindly online. He said, well, this is new thing, SPVs and syndicates. And I was like, explain that to me. And he explained it to me. And I was like, I don't understand it. Explained it to me again, explained it to me again.

• 1:01:53Speaker 00

  And then he sent me a link and it was, you know, angel.co/jasonssyndicate. And it said, you know, set up your syndicate here. And I filled out the stuff and I tweeted it. And then he called me in the phone and said, what are you doing? And I said, what? And he said, you're not supposed to tweet it. I said, it says on the page, tweet your syndicate. He goes, I didn't launch it yet. It's launching on Monday. And I said, oh, I'm sorry. You want me to take that? And he's like, no, don't worry about it. TechCrunch got the embargo, but they're upset. I was like, nobody's going to see it. It's on Twitter. Nobody's on Twitter.

• 1:02:19Ben Gilbert?

  And it's also so interesting that like, in your head, you're like, this is, I don't, I don't get it. Why would people sort of like, invest alongside another person without ever meeting the company in person? And that's what Sequoia was doing with you. They were giving you money.

• 1:02:31Speaker 00

  Yeah, no, I'm, listen, Ben, I'm not saying I'm the smartest guy in the class. All right. I never said that. That's not my claim. I'm a hustler. All right. That's why I made that self-deprecating joke in the book that you were so nice to read. You know, like, I am a hype guy. I'm not a complete fraud. That's kind of me being self-deprecating. But, you know, I've definitely been lucky and I'm definitely good at hyping things. So, I mean, that's why Naval sent me the link. Anyway, a bunch of people joined. Tim Ferriss launches his.

• 1:02:58Ben Gilbert?

  I don't think we should glaze over this. Like, the set of people you've already talked about, clearly there's something special about the way you build relationships. I mean, you're, you're

• 1:03:06Speaker 00

  I'm fun.

• 1:03:07Ben Gilbert?

  keen to spot yourself like as a hustler, as someone that works hard, as someone that is extremely driven. But lost in, I think, the way that you think about this is, oh, my God, are you good at building relationships? And Making it so people want to help you, like helping them, knowing that over the next 10 years, that's going to be a good bet.

• 1:03:25Speaker 00

  Um, I think enthusiasm is contagious. Um, so I've always been very enthusiastic at what I do and I always pick up the check and I always set up dinners with a lot of people and I always introduce people to other people with no intent of capitalizing on that. Like Tim O'Reilly invited me to a food camp early on where Larry Page came in his helicopter and landed it outside of food camp. And I was like, Larry, what are you doing? Like, you realize how douchey it is to land from a helicopter? He's like, you think so? I was like, dude, come on, man. Just land it at the airport. I mean, we know you're rich. Like, you don't have to fly your goddamn helicopter from Palo Alto. He's like, you're probably right, Jason. I totally admonished Larry Page. Uh, he was pretty funny, but he did literally have them clear the field so he could land his helicopter. He was taking

• 1:04:09Speaker 00

  helicopter lessons at the time at food. So I'm not speaking out of school. He literally landed his helicopter there. Um, anyway, um, Tim O'Reilly said something about like, I can't remember the exact phrase. You'll find it put in the notes, but he said something about like, the, if you extract very little from the network you're building, you do really well. Like, you don't need to extract all the value.

• 1:04:26Ben Gilbert?

  Yeah. It's like the Bill Gates platform quote.

• 1:04:28Speaker 00

  Something like that. Yeah. But he evolved. He said it better. Uh, we'll come to, but this is sort of thing about networks. Anyway, so I was always just introducing people to everybody. In fact, I remember when I was at the top of my game within Gadget, I was at Sundance and my friend David Sacks was producing a movie there called Thank You For Smoking. So we were all there. I just saw Weblogs Inc. Elon, myself, Sacks, we're all hanging out. My wife and his wife at the time and Sacks' new girlfriend is now his wife. And, um, Walt Mossberg is there and he says, hey, let's have lunch. Uh, cause he knew I was there. I was like, yeah, sure. Um, and I was like, hey, you know, let's meet over here. I'm going to bring my friend Elon. He's like, who? I'm like Elon Musk. He's doing this like thing or whatever. And, you know, Walt Mossberg was very big there.

• 1:05:12Speaker 00

  And he's like, he wrote me this admonishing email. I agreed to have lunch with you, not Elon Musk. You forcing me to have lunch with this person like is just unfair, like our friendship, whatever. I was just like, oh, okay. I won't bring him.

• 1:05:24Ben Gilbert?

  I was trying to help you out.

• 1:05:25Speaker 00

  You know, Walt was very sensitive at the time. Everyone was trying to get to Walt. And so he felt like I was trying to put Elon in front of him and Elon didn't even know. I was, I was just like Elon's here. Elon wasn't running Tesla at the time. He was just an investor and he was doing the SpaceX stuff. I was like, you should meet my friend Elon.

• 1:05:38Ben Gilbert?

  So you're good at, at.

• 1:05:40Speaker 00

  I was always good at just connecting people and meeting people together and just hanging out with people. Like my book agent, John Brockman, had introduced me to Sam Harris. You know, Sam was on my podcast and he did like AMA from a hollow. And he said, how do you do podcasting? I was like, you know, you're built for podcasts. He's like, you think I should do a podcast? I was like, absolutely. You're built for it. He's like, what do I need? I'm like, a guest and a microphone. He's like, oh, I was like, you can use my studio. Anyway, I convinced him to do a podcast and now like the rest is history. Um, and I introduced Sam to Elon and then we all started talking about AI. And Elon introduced Sam to the concept of AI and all this AI stuff going on, the book, Super Intelligence and all that. And then the people who write Westworld, Christopher Nolan.

• 1:06:23Ben Gilbert?

  Yeah, and Lisa.

• 1:06:23Speaker 00

  And Lisa Joy then met Elon and Sam. And if you like, literally the entire season this year, I'm watching it. I'm like, this is a conversation I had with the four of these people.

• 1:06:34Ben Gilbert?

  Oh, my God.

• 1:06:35Speaker 00

  Like 34 years ago. It's pretty surreal. I always picked up the check and I always brought everybody to dinner. That's why I got good at this and I'm, you know, that's how.

• 1:06:45Ben Gilbert?

  We're not doing playbook this episode, but this is the little.

• 1:06:48Speaker 00

  That's your mini playbook. Just always buy dinner.

• 1:06:50David Rosenthal?

  Okay. So I gotta ask though, that playbook, that mindset, that wanting power and connecting people.

• 1:06:59Speaker 00

  Yeah.

• 1:07:00David Rosenthal?

  As Mahalo is, you know, post panda going on.

• 1:07:03Speaker 00

  The panda is the update that Google did, yeah.

• 1:07:06David Rosenthal?

  Why do you not go join a venture capital firm and become a traditional venture capitalist?

• 1:07:11Speaker 00

  Self-awareness. Yeah. I mean.

• 1:07:14David Rosenthal?

  Which you can't have to be a VC, as we all know.

• 1:07:17Speaker 00

  Well, here's the thing. It's called a venture partnership. And that's not what I do, right? Like I like to make my own decision and I'm like the solo artist. Like you put somebody like me in a band, the band will break up. Like not a good idea.

• 1:07:32David Rosenthal?

  Dylan, not like Eddie better.

• 1:07:34Speaker 00

  Yeah, you know, like I could play, you know, I could play with Tom Petty and the Heartbreakers, but I'm going to write my own albums. I want to do my own thing. I don't want to, I want to keep it small and authentic and true to what I want to do. And I'm, I did have a bunch of venture firms over the year make runs at me and then maybe want to incorporate my little empire into their empires. You know, it'd be a pretty good feeder. You could plug what I'm doing into something bigger. If you were a billion dollar late-stage fund, imagine having, you know, the only real viable Y Combinator competitor out there as the top of your funnel, the only real Angel List co-exister competitor. These things are not really competitors when you think of them, they're really co-existors. But, you know, we're the number one largest syndicate in the world and Angel List is

• 1:08:18Speaker 00

  the largest collection of syndicates. But if you took the top two or three syndicates together, they would be smaller than ours on Angel List. And then you look at our program, like really the only people who compete with Angel List with Y Combinator heads up. Like, the only reason, we've had people pick us over Y Combinator and people pick Y Combinator over us or go to Y Combinator and then come to us. Like, we're really the only, I think, accelerator who can say that.

• 1:08:41Ben Gilbert?

  All right, listeners. Now is a great time to talk about a new partner of ours here on Acquired, Logora, the agentic operating system that is redefining how the world's best legal teams work.

• 1:08:54David Rosenthal?

  Yep. It's sort of obvious that AI is going to completely change the legal industry. I bet most of you listening have dropped a contract into some sort of AI chatbot out there. Logora took that insight and asked the question, what if you really built something with that power from the ground up for the legal industry?

• 1:09:11Ben Gilbert?

  So the founders did exactly what great founders do, operate with obsessive customer focus. They embedded inside a massive law firm for months. They sat with the lawyers just watching how the work really gets done.

• 1:09:26David Rosenthal?

  And that's how you get features that customers love, like tabular review, where you drop in a folder of hundreds of contracts and it pulls every key term into a grid a lawyer can actually work with. Legora's bet here is interesting. Since it lets each lawyer handle more complexity, any given person can increase the quality of their work and do higher value work. And this means that the pie can grow even as each individual task takes less time.

• 1:09:50Ben Gilbert?

  And they recently launched Legora Agent, offering greater intelligence and performance. The agent lets lawyers set an objective, then it can handle the planning and the execution and delivery of the final product. Legal teams get to maintain full control and transparency since they're still involved where judgment is required.

• 1:10:09David Rosenthal?

  And Legora works where you already work. You can use it within Microsoft Word while redlining or drafting. The early Legora numbers essentially speak for themselves. When they have a head-to-head pilot with their top competitor, they win 70% of the time. Legora now has over 100,000 lawyers on the platform from 1,200 legal teams in 50 countries. And crazily, they went from 1 million to 100 million in ARR in about 18 months.

• 1:10:39Ben Gilbert?

  Truly insane numbers. And that is the real test. Plenty of things demo well, but the question is whether a busy associate actually reaches for it during crunch time, or whether a partner trusts it before going into a conversation with a major client. If your legal team wants to check it out, whether you're a law firm or you're in-house at a company, you can learn more at legora.com/acquired and just tell them that Ben and David sent you. Jason, I want to tee this up in this direction. So you want to be a solo artist, not

• 1:11:09Speaker 00

  I am a solo artist.

• 1:11:10Ben Gilbert?

  not join a band. Or, I'm sorry, at this point in time, I'm just playing through what's in your head.

• 1:11:13Speaker 00

  Yeah, yeah.

• 1:11:14Ben Gilbert?

  You want to be a solo artist, but you also deeply understand returns to scale. As you're thinking through this week in startups, the syndicate, which I want to really understand mechanically how that formed and how that works, how are you thinking about scaling what is working for you?

• 1:11:30Speaker 00

  Yeah. So I had started the podcast as Calacanis Cast, and we did 40 episodes or so of that, just on an open microphone in a room. And I did it with Ron Conway and I did it with Ev Williams because my friend Dave Weiner had started, who created RSS.

• 1:11:46Speaker 00

  Said, hey, Jason, check this out. You can attach a file to an RSS feed. I was like, oh, you could put a PDF in there? It's like, yeah, you could put a PDF in there, but that's the same thing. And I was like, oh, yeah, again, I'm not the smartest kid in the class. He's like, check this out. And it was an RSS feed with MP3s. And I said, oh, he's like, now check this out. And he sent me a little script. And it took the RSS feed and then it wrote the MP3 files as an album into your iPod. And the reason it's called podcasting is because you could sync your iPod on your Mac to an RSS feed that then put it there. So, the idea was you would plug your iPod in at night to sync and to charge to your Mac. And also it podcatch, it would download at night, all those things. And when you got

• 1:12:31Speaker 00

  on your commute, you'd have a couple podcasts on there. And I was like, wow. And then they convinced Steve Jobs to add it. To iTunes. To iTunes. And there's a famous clip of me talking with- Two thousand and six or seven. Yeah. And there's a famous clip of me talking to Steve at the D conference and asking him a question about it. And I asked him about making money, if we'd ever sell advertising on podcasts or whatever. And he said, you know, it's a really good idea. You should just email me, Jason. And I said, yeah, the email I always email you at. And he said, yeah. And the whole audience laughed. But I just said it as a joke, like, be the wise ass. You know, because I did talk to him on email. And so I thought it'd be funny to say, you know, like the email we always talk on. I mean, the whole audience cracks up. It's a very funny clip. But anyway, I did the podcast because I just thought it'd be

• 1:13:15Speaker 00

  fun. And to me, it was just a fun way to promote my friends. And so, you know, I had Brian Alvey on, my longtime collaborator, the first guest, David Sacks came on early, just, you know, Jason Nizar was starting a company, just having people on when I was in LA. And then Bing was going to launch it. Somebody from Microsoft called me and like, hey, we love this like podcast thing you're doing. We want to tell you about something secret. And I was like, what is it? He's like, we're starting a surgeon. I was like, everybody knows. He's like, yeah, it's called Bing. I'm like, well, that's a terrible name. And he's like, well, anyway, we want to advertise on your podcast. This is 11 years ago. And I was like, okay.

• 1:13:48David Rosenthal?

  You hadn't thought about, you hadn't put two and two together.

• 1:13:50Speaker 00

  There was no advertising in podcasts. It was just like blogs. It was just a thing.

• 1:13:54David Rosenthal?

  But of course, it was just like when you're starting Silicon Valley Reporter, Weblog, like, it's the same thing.

• 1:13:58Speaker 00

  Anytime a new medium comes out, I assume it's going to work. This is my big trick in life. Whenever something comes out, I just assume it is going to reach critical mass and I behave as such. So when blogs came out, I was like, okay, I assume it's going to work. I'm going to go full bore as if it's going to. When podcasting came out, I went full bore. Whenever everything comes out, I just, if I, if I'm interested in it, Twitter, the same thing. I just went full bore on Twitter.

• 1:14:22Ben Gilbert?

  When has that not worked?

• 1:14:24Speaker 00

  Oh, God, probably more times than I can count, but I mean, it's.

• 1:14:28David Rosenthal?

  But, but it doesn't matter when it doesn't work.

• 1:14:30Speaker 00

  Yeah, I mean, I have a Tumblr, uh, you know, there's a bunch of, uh, path.com, uh, friend feed. There was a bunch of other things. But if you take the Robert Scoble relentless enthusiasm, like Spastic, like, oh, my God, this is going to change everything. Google Buzz, Google Plus, you know, like, I was all in on those services too. And that was all wasted time. But, you know, when it does hit, people remember the hits. Like, it's just the same thing about it that you guys know about investing.

• 1:14:55Ben Gilbert?

  And asymmetric returns, yeah.

• 1:14:57Speaker 00

  Yes, asymmetric returns. Correct. If you, if you get in early and you have the, the, you know, you're baking in whatever that service is, and you got there early, you're gonna, you're gonna have a head start on everybody else. So then it just worked for me. And then they bought, they were like, how much are the ads? And I was like, um, uh, $3,000. And like, okay, uh, per ad. I was like, yeah, but you have to buy 10. And they're like, okay, $30,000. And you just sent me $30,000. And they're like, I was like, they're like, what is the ad? I was like, I'll just talk about Bing. And so I literally would just pull up Bing. And I'd be like, hey, check out this feature. Check out that feature. Thanks, Bing. Bing, Bing, Bing. And then we, that'd be the end of the ad. They're pretty funny.

• 1:15:30David Rosenthal?

  Remember those. So great.

• 1:15:32Speaker 00

  Yeah, we just goofed off. And we'd have puppets on the show. We just, it was just this like vaudeville kind of approach to it. But then it started getting a little, you know, went from like, you know, 500 to 1,000 people would see it to 10,000, 20,000. You know how this stuff goes. 200,000, 300,000. All of a sudden, it becomes a thing.

• 1:15:47Ben Gilbert?

  And what's the listenership on This Week in Startups now, just to give people a sense?

• 1:15:50Speaker 00

  Over 200,000 per episode. Yeah. Yeah. So you guys are right on my tails. It's a niche podcast by design. Like, I could make it get bigger by dumbing it down, or going shorter, or having post-production on it. But I just told everybody, I'm not interested in that. And, and, you know, Joe Rogan has taken the same approach, the same, you know, Howard Stern-like approach. As you put the recorders on, as long as it's interesting, you go. And we have three ad slots, and we sell them out every year. And it does, you know, a couple million bucks. And that's enough to pay for a seven, eight person team that works on the podcast now. That's awesome. And how does that play into your angel investing? So to take us back- Well, it's very simple. Yeah, I mean, I would say on the podcast, hey, you know, here's a company I invested in. I'm having him on the podcast. Or in the case of com.com, somebody had told me Alex was like a genius.

• 1:16:34Speaker 00

  And I was like, why? And he's like, well, he did the million dollar homepage. I was like, oh, that was genius. He's like, yeah, I do a meditation app. I looked at it. It was a webpage where you went and it just played a meditation in a loop. And I was like, yeah, I'll have him on the podcast. I need a guest. You know, back then it was just like, can we get any guests? And so Alex came on and so on the episode, I said, hey, can I put 25K in, you know, for like 1% or 2% or whatever? And he's like, yo, we talked about it-

• 1:16:54David Rosenthal?

  You did this live on the episode?

• 1:16:55Speaker 00

  I did it live on the episode. And you know, I was always trying to get somebody to do that and nobody would do it. But I thought it was funny. It was entertaining for me. Anyway, long story short, he, you know, I put 50K in for my fund. And this Angelist thing had just come out and I made it the first deal on Angelist. And my expectation was maybe another 25K would come in or 50K because I had like, you know, I don't know, like, I don't know, 100, 200 people had signed up. So I was like, ah, and $328,000 came in. And the company was worth 4 million or 5 million at the time. We had a 6% or 7% position. And that company's worth 1.4 billion now. It's the most successful syndicate in the history of syndicates. In fact, it's probably the top three syndicates combined would be smaller than the com position.

• 1:17:38Speaker 00

  And for people that have never used Angelist, how does that work where you're like, hey, I'm in for 50? How is it that like- Well, the original deal was Angelist would take 5% of the carry. I would get 15%. I subsequently negotiated an 18 and 2 deal, which led to a lot of animosity. Eventually Angelist and I broke up. That's another story to tell. But you know, Naval and I are friends still. But we were just a little too big for it. And that's, you know, like back to being very clear about like, I'm not the bull you want in your china shop. Like, I know that some people think like, wouldn't it be great to buy Jason's company? And put it as part of this big venture firm? The answer is no, because I'm going to do what I want. And it's going to knock it over inside your place, right? Like, it's not good for you.

• 1:18:19Speaker 00

  It's not good for your partnership. If you're trying to build a partnership and you want five or six people to sit there and have like a really good conversation and dialogue about an investment, that is the, that to me would be purgatory.

• 1:18:30David Rosenthal?

  That's your nightmare.

• 1:18:31Speaker 00

  It's literally my nightmare. Like, I want to make an investment because I look in the founder's eyes and I push the chips in. I do not want to have five people sitting in my seat while we discuss if I should go all in on this poker hand. That's the opposite of what should happen in early-stage investment. The second you debate it is the second you lose the outliers, because the outliers make no frickin' sense. So, anyway, consensus equals death in the early stage. Consensus at later stage equals protecting downside risk and due diligence and all that stuff is very important. I get it. Certainly.

• 1:19:01David Rosenthal?

  Can we digress for a minute before we pick back up with the story of your empire? But talk to us a little bit about your philosophy, because I think it's super, it's super incisive about the difference between bets and like informed by poker, shaping your bets, experiments versus investing.

• 1:19:17Speaker 00

  Yeah. So, here's the thing. Imagine a poker table existed in the world where you would buy in for $10,000, and there were 10 players. So, it's $100,000 on the table. But every 100 hands, you could win $1 million or $10 million. So, there was uncapped upside. Somebody just gifted $900,000 extra dollars or $9.9 million extra dollars to that table. It would change the way people played. It would change the game. There would be, and that's called the World Series of Poker, by the way, for pros, because the World Series of Poker, when they have that series of like 50, 60 games, all these amateurs come from

• 1:20:02Speaker 00

  the world, dead money, people who are easy to pick off. It's like for the pros, for Phil Hellmuth, it's literally like if you started the NBA Finals and the Warriors had to play against the high school team. We'd be like, well, we're just going to win a lot of games here.

• 1:20:16Ben Gilbert?

  It's the only way to get asymmetric upside in poker.

• 1:20:18Speaker 00

  Correct. I mean, there are ways, but yes, asymmetric, for sure. So, anyway, once you realize that, that frees you from you trying to understand if the idea is going to win or not. That's what trips early-stage investors up, which is why I wrote my book, is because I felt I had figured something out and I wanted to share it with the world, which was, this is the greatest casino in the world, in my opinion. And nobody knows about it. And the people who do know about it do not want to talk about it. And then another group of people think it's the stupidest thing in the world and a scam. And why is that? Well, most people come into angel investing, who I meet, who think it's stupid.

• 1:20:58Speaker 00

  And they had $500,000 in their bankroll and they gave 250,000 of it to their daughter's, sorority sister's, ex-boyfriend's brother. And because they're going to build an Instagram competitor that has links in the comments. Because Instagram doesn't support links in the comments. Like, that's the reason, like, they're going to exist. And they put the 250 in. The product never gets released. They give that 250 to Dev Shop in Estonia that never finished. They ask for another 250. They give the other 250. The product comes out, nobody cares. They shut it down. Those people go work at Boston Consulting Group or whatever. And they made one bet. So it was literally like walking up to blackjack and putting your entire stack on one hand. Like, it's just not enough.

• 1:21:39David Rosenthal?

  Or like in poker, like betting, you're going all in before the flop.

• 1:21:43Speaker 00

  Yeah, before you look at the cards. You're just like, I'm going to sit at this table and put it all in on the first hand. Which I know some people who do that for fun.

• 1:21:50Ben Gilbert?

  For people that are not professional investors, it sounds ridiculous to dumb it down this far, but like, even if you're only making five, six, seven angel bets and you're not really creating a, you know, 12, 15, 20 company portfolio, it's mathematically the same thing. You're taking way too concentrated of a bet.

• 1:22:05Speaker 00

  Really, and you need to really hit 20 or 30 or 40 in what I've seen in angel investors who succeeded. And you have to be investing in a certain pool of entrepreneurs. If you're a nobody who starts out, any deal flow that gets to you, by definition, has been picked over by all the qualified people. If you're reading scripts in Hollywood as a first-time director, and the script got to you, that means every director has passed on it and never got to the good director. So just understand that.

• 1:22:36David Rosenthal?

  Okay, so this is what I want to, I want to go deeper on. Because I think this is, there's a really important insight here.

• 1:22:43David Rosenthal?

  How do you square the, what you said a minute ago about consensus, at the early stage consensus kills because you want the crazy stuff, you can't predict.

• 1:22:53Speaker 00

  Right.

• 1:22:53David Rosenthal?

  With this aspect of you need the high qual, like what is the signal in the quality?

• 1:22:58Speaker 00

  Yeah, so what I teach, we have a course called Angel University that goes along with Angel, the book. And in that course, I explain to people that when you make your first 20 or 30 bets, make as small a bet as possible, which means using syndicates is a good idea. Forget about mine. Just sign up for everyone because it's free to read the deal memos and you'll learn. But if you do that, you're playing at the lowest stakes poker table while you learn. Like literally, if you could play $1 blackjack, if you wanted to learn blackjack, sit at the $1 blackjack table instead of the $100 a hand. Because you're going to lose a minimum and it doesn't matter if you lose, it's just the education, it's like paying for an educational course. And I tell people, only invest in companies, startups that have

• 1:23:40Speaker 00

  gotten their product to market and have some customers. Hopefully paying customers, but if not, customers who are using the free product that you can at least talk to. You've now eliminated, as you guys know, 90% of the failure rate. 90% of the tritium in startups comes from-

• 1:23:53David Rosenthal?

  Just don't ship a product.

• 1:23:54Speaker 00

  They never ship the product. Then you get down to that 10%, of that, 90% of those never get a paying customer. So if you were as you're a starting angel investor, to only invest in companies with some amount of revenue, even as little as 2,000 to 10,000 a month, you probably have eliminated 80, 90% of the risk. So start there while you're learning. And then as you get more sophisticated, just like in poker, if you want to play under the gun with Phil Hellman at the table, and you want to play nine, 10 suited, okay, maybe. If you've been playing for 10 years. But you don't want to take those kinds of risks and bet on a meditation app, or a couch serving app when you're just getting started. There's five times you could have invested in Calm, maybe three, four, or five times in Calm, three, four, or five times in Robinhood. Even these outliers, Airbnb, you probably

• 1:24:37Speaker 00

  have four or five chances to invest in Airbnb as an angel investor. It's a misnomer that you're going to miss the deal. Like what Y Combinator does to angel investors and telling them, if you don't invest quickly, within these 48 period, the deal's closed and you miss them forever. It's like, just literally not true. It's literally, they try to create a false sense of urgency. They train the founders to do this and it's nonsense. Not only is that round not closing immediately, there's going to be four rounds after that you can get into. No great investor invests at demo day.

• 1:25:07Ben Gilbert?

  Well, especially now with safes and not price rounds. Like it's rolling.

• 1:25:11Speaker 00

  It's rolling.

• 1:25:12Ben Gilbert?

  Yeah.

• 1:25:12Speaker 00

  Super rolling.

• 1:25:13Ben Gilbert?

  There's one thing you said that I think is really insightful. When you're not Phil Hellmuth and you're playing poker for the first time, like just invest in things that have shipped and have revenue. And then, once you get better and better and better and you become Jason Calacanis, you can invest in Calm. Why are you comfortable at the level you're at, investing in a no revenue meditation website? Why was, why was that okay?

• 1:25:34Speaker 00

  Yeah, so I can take you through the background. It was very simple. I had known Sam Harris. I had done positive visualizations. I had heard that term and I used that in sports because I was a psychology major. I had done positive visualizations to get through the New York City Marathon, which I did 11 of. I didn't know it was called meditation, but I just positively visualized myself along the route. And then, when I did the run, I had had that in my mind, how good I was going to feel at each part and how the Bronx and the wall was going to be difficult. Then, when I saw Calm, I talked to Sam Harris about it because he was studying, you know, he was doing CAT scans of brains and he was a meditator and into psychedelics and all this stuff. And he put me in touch, when I was doing my research on Calm, with a woman who ran the mindfulness center at UCLA.

• 1:26:19Speaker 00

  And I found out that Phil Jackson, who I had known when I was in LA, when he was coaching the Lakers, I had become friends with him. And he had Kobe and Shaquille O'Neal meditating and I just, it clicked for me. Wait a second. Phil Jackson, innovator, Sam Harris, innovator. There's something at UCLA around the corner from me in Brentwood. They're studying it? They have a program? They're teaching people this? Oh, they're studying it on PTSD soldiers? This is the future. But unlike yoga, which also started in Santa Monica, this can be delivered through your ears. Wait a second. Yoga, you have to do in person and yoga's everywhere. But meditation is delivered in your ears.

• 1:27:02Speaker 00

  If this does work and it becomes as popular as yoga, there could be 100,000 people paying for this.

• 1:27:09Speaker 00

  It could be like a $10 million a year business. Companies worth $4 million, this could be like the future. And that's when it all clicked for me. And it was like an easy bet for me to make. And then the subscription service came out and Apple allowed subscriptions. And when I think we invested in, when we invested in Com, I think they had done 10,000 in revenue, you know, selling a month.

• 1:27:27Ben Gilbert?

  Okay, so it was a post-revenue startup.

• 1:27:30Speaker 00

  They had post-revenue, yeah, yeah, they did. But with Robin Hood, they didn't. Robin Hood hadn't launched yet. So that was another one where I just, you know, I saw them and it made sense to me. So, you know, you can get signaling. I'm not saying you can't do this, but if you want to reduce the amount of pain you're going to go through and you want to have a less painful junior year, like your junior year as an angel investor, when you hit the J curve, is so painful because you think you're an idiot.

• 1:27:56Ben Gilbert?

  You've deployed all your money, nothing's breakout yet, and you don't have any, you can't keep investing.

• 1:28:01Speaker 00

  Oh, and half your portfolio can't raise money and is shutting down, and the other half can barely raise money and they're begging you for a bridge. Like, literally the junior year, everything tells you to quit. And then all of a sudden, you're four, five, or six, you know, Travis calls up and he's in six cities and he's closing around with Menlo at 300 million. And you're like, wait a second, 5 million times 60, and holy, that's a lot of money. You know, you start saying, oh, whoa, this could work. And that's when you, when, once you hit one of those unicorn-type investments, then all of a sudden, it clicks in your brain, your brain chemistry changes. You have to have the brain chemistry change from being risk averse and outlier averse

• 1:28:46Speaker 00

  to outlier obsessed. I am outlier obsessed. I do not care about losses. I literally, and that took me a long time, because remember, I was such a rabid competitor? The idea of being fine with losing all the time, like imagine losing 29 nights in a row at poker, but on the 30th night, you hit a 5,000 X or a 200 X.

• 1:29:09Ben Gilbert?

  Right. It's because you're playing in this very special poker table right now where the losses don't matter, supposing that you actually are fishing in the right pond where you do find those magical ones.

• 1:29:19Speaker 00

  Correct, Amando.

• 1:29:20David Rosenthal?

  I think there's one more layer, though, that I don't think we've touched on yet that I've heard you speak about before, which is shaping your bets into this. And like, as you're making these angel investments, keeping them very small and thinking of them as experiments, that like, to me, that seemed as like a really good mental trick to be like, it's not a loss, it's a failed experiment.

• 1:29:41Speaker 00

  Correct. And this is why I started the Launch Accelerator three years ago. We have 100 companies I've gone through. And I basically was like, what was Paul Graham's original idea? Oh, six or seven companies? Great. I'll just copy that. Seven companies. And Paul was the draw, right? And now it's the legacy's the draw. Paul Graham's not the draw, it's the legacy. So I said, okay, well, if Paul was the draw, I know I'm a draw, so let's see if it works. And I just said 7% of, 6% of preferred for 100K, which is a $1.7 million implied valuation. So fuck it, we'll go with that. We'll just start accepting seven people at a time and deploying 700K at a time. But then I added something,

• 1:30:22Speaker 00

  which was, you know, YC, imagine if YC and Angel List got married or merged. What would that look like? Well, that's what I had. And I had left Angel List and I had started thesyndicate.com. It took me a while to get that domain name, but I got it. Coveted that one. I'm a domain name coveter. I'm a brander. Anyway, the point is, I started saying to people, I'll put in 50K for, the original deal was like 50K for 5%. I'll put in 25K for 5%. Then I'll put 25K, whatever your recent round is, and then I'll syndicate it. And then it was too hard to just syndicate all of them because not all of them wanted to do the syndicate. So then I just said, okay, we'll put in 100K. It's the same deal

• 1:31:04Speaker 00

  as YCombinator at the time. So then we're betting on these for 1.7, you know, rounded up to $2 million valuation. And then one of the companies raised a round, and I was like, I always told myself, we'll put more money in, in the seed round, and we'll try to get to 10% ownership. And then like two of the best companies raised rounds and the founder was like, well, we have no room for you. I'm like, what? I was like, I introduce you. So I called up those people who are doing the rounds and I read them the riot act. I said, introduce this company. How dare you try to muscle me? I said, you're swinging an elbow at me? I said, I'm the point guard. I passed you the ball and now you're, you're, you're, you're not passing the ball back when you're

• 1:31:45Speaker 00

  triple team. Like pass the ball, move the rock. And I got both of those people to give me allocations. And then I was like, well, this is not how power is supposed to work.

• 1:31:56Speaker 00

  Like if I'm the point guard, I have the power. I have the power to freeze you. So then I said, okay, now the freezing will begin. So I wrote into our documents that we have the right to do half the next round.

• 1:32:08Ben Gilbert?

  It's a hefty pro rata, my friend.

• 1:32:10Speaker 00

  Not if you're Jason Calacanis. And not if you're the founders. It's a feature, not a bug.

• 1:32:16Ben Gilbert?

  Yeah.

• 1:32:16Speaker 00

  It's a feature for the founders who we work with because they can start their fundraising with me as an anchor. And, and, and they do.

• 1:32:24Ben Gilbert?

  And do you? So, so do you pick winners? Do you say, hey, you three, you guys are getting the half the round from me?

• 1:32:30Speaker 00

  Yeah, we've evolved it over time. So in order to make it more fair to everybody, what I say to them is if you're tripling revenue, if you're doubling revenue six months, we're likely to just preemptively make you an offer if your performance is in the top like 5%. And we've done that. And then we'll let other people invest in it, but we'll actually price it around and put it in 500K or 250K and get them started. I said, for everybody else, if you're not like just crazy outlier, where you're tripling revenue, you know, every six months or something during the program, just go ahead and, but we'll still leave room for other people. When you get your term sheet, give it to us. We'll have five business days or something to make a decision and we'll let you know what our, what allocation we want to take. But we'll usually do it in a day or two, which is actually

• 1:33:15Speaker 00

  what Y Combinator announced they're doing now.

• 1:33:16Ben Gilbert?

  That they're doing now, yep.

• 1:33:17Speaker 00

  Yeah. So they switched to my position. And because I think they were experiencing the same thing, which was they were getting boxed out of their winners. And so now we just say, give us the term sheet. And if it's a reasonable term sheet, it's not like something outrageous or non-traditional. Like we had one of our successful companies do a deal for Common. Shares at a ridiculous price with some non-traditional private equity firm and we passed. We said, we'll just stick with our 6%. But other times we'll put in 500K. And so for a company like Fitbot, a major breakout for us, they came to us with just $2,000 a month in revenue, I think, or maybe 1,000. And they've been public about hitting eight figures in revenue. They were public about that at the launch festival. They gave

• 1:33:59Speaker 00

  a keynote. And I offered them live on stage, 2 million out of 50 million posts. But anyway, we wound up putting more money in a couple of times. We built our position up to over 10%. So that's what I'm trying to do now is just get to 10, 15, 20%. And eventually, with our fund, the syndicate, and the accelerator, we can make three or four bets in the company and get to know the founder. And if we can do this three or four bet thing, we'll be the first people to combine Y Combinator, Angel List slash Seed Invest slash Republic, whatever crowdfunding syndicate you like, with a seed fund, like Homebrew or Pair or

• 1:34:43Speaker 00

  whatever. So that's what I'm constructing right now. We don't have a proper Series A because we don't need to, because the fund plus syndicate kind of hits the 1, 2 million dollar number. But the next fund, perhaps, we'll be able to do a full A, like a 5 million dollar A. But I don't need to do that. I kind of like being in the early stage. It gets less interesting for me to go and do the big checks. And there's so many specialized people at that. I'd rather hand it off to Sacks, or Chamath, or Bill Gurley, or Ruloff, or somebody like that.

• 1:35:16David Rosenthal?

  All right, listeners. Now is a great time to talk about one of our favorite companies, Statsig.

• 1:35:22Ben Gilbert?

  Yes. There is a reason why the best product teams rely on Statsig, whether they are iterating on their core product features or shipping AI-powered experiences at scale.

• 1:35:33David Rosenthal?

  Yep. In the crazy speed of today's AI world, shipping fast is just table stakes now. It's basically trivial to build and deploy your app constantly. The real advantage is how Quickly you learn what changes actually created value for customers and how fast you can use that signal to guide what you ship next.

• 1:35:53Ben Gilbert?

  This is where Statsig comes in. It brings experimentation, feature flags and product analytics into one unified system. So teams can ship safely, test rigorously and directly link what they changed to how users actually behaved.

• 1:36:06David Rosenthal?

  So if you want to make learning your competitive advantage, whether you're building new AI experiences or just evolving your existing core product, go to statsig.com/acquired to get started.

• 1:36:17Ben Gilbert?

  Well, Jason, this has been like so fun. We got to do this more often because it's incredibly fun to riff with you. I think this is a good place to call it for the the main show here. And for the LP show, I think what we're going to do is we're going to dive into your investing, the the way that you're sort of frankly, deconstructing the the jobs of a VC firm, sourcing, evaluating, you know, winning the deal, helping and then future access to capital. It's really interesting what you're doing. And I also want to discuss the way that all these things tie together and how you sort of view the flywheel or the funnel or how you how you sort of visualize it. And then I know you've got some.

• 1:36:52Speaker 00

  Good insider stories.

• 1:36:53Ben Gilbert?

  Good insider stories for sure, the couple you brought up. And also, like frankly, the way you see the world.

• 1:36:58Speaker 00

  Yeah.

• 1:36:59Ben Gilbert?

  I'm sure there's a hot take in there.

• 1:37:01Speaker 00

  I got a hot take post Corona.

• 1:37:02Ben Gilbert?

  Yeah, yeah, yeah. So.

• 1:37:04David Rosenthal?

  All right.

• 1:37:05Ben Gilbert?

  Listeners, thanks so much for going on the journey with us here.

• 1:37:07Speaker 00

  Spend the hundred, spend the hundred bucks, become an LP member like me.

• 1:37:11Ben Gilbert?

  All right, listeners, thanks. LPs will see you on the other side.