Acquired - Special Episode- Jason Calacanis

0:00Let me just make a little add here. Yeah, please. Hi, this is Jason Callicanas for acquired.fm. Is that the domain of where? That is it. Yeah. All right. Listen, you're listening to this. You're either a founder and aspiring founder and 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.

0:29If I could tell you you get one, two, three good insights a year, even one, which pay $100 for an amazing insight, that gave you an edge against your competitors. Of course, you would you 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 required out of them is not. It's not content. It's an edge. And it's an underpriced edge. So buy for 100 now before they raise the price to what it should be.

0:56which is 5,000 in here, this is Jason Calcass, for required.fm. See you in the Slack. How's that for an ad, huh? You can have that. You can actually take your mic out. You can literally have my ad. You can have my ad. I swear we did not ask him to do that every one of you. No, I just love it. Let's do it. Let's do it. Let's do it. Let's do it. Let's do it. Let's do it. Let's do it. Let's do it. Let's do it. Let's do it. Let's do it. Let's do it. Let's do it. Let's do it. Let's do it. Let's do it. Let's do it. Let's do it. Let's do it. Let's do it. Let's do it. Let's do it. Let's do it. Let's do it. Let's do it. Let's do it. Let's do it. Let's do it.

1:35Acquired 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 Callichannis. So just to give our audience a small sampling of all of the enterprises that Jason has started and has involved with.

2:02across his career. Yeah, David, I bet you can't do this all in one breath. Oh, no, no. Jason has founded four companies by our account, Silicon Valley reporter, Weblogs, Mahalo, and Inside.com. Do we miss any? No, those are them. Those are the four. And Inside.com is the same captive, which is the pivot of Mahalo. So arguably one did not know people don't know that. Three conferences, three podcasts, Angel All-In, and of course, this week in startups, which is now over a thousand episodes.

2:32the YouTube channel around all of those. You were the first Sequoia Scout. You were literally the prototype of the Sequoia Scout. Correct. And still the greatest returner. And still the greatest returner. But who's counting? It's not a competition. But I won. Maybe some time might have something to do. Well, anyway, we'll get into that. You've made over 200 angel investments in your career. You are a blogger. You're an author. You have a newsletter. You started the launch accelerator. The venture fund around that. The syndicate around that.

3:01You are the self-provests. We have you on record as saying you are the either third or fourth best angel investor of all time for sure. Yeah, for sure. I'm out rush more. Chris Saka or on Conway obviously ahead of me and then there's a bunch of people we nobody knows who did incredible angel investments. You know in Google and Apple but they don't have like the they don't feel the necessity to put it on the cover of a book like I did. Speaking of quote that we want to wrap this up.

3:30with, 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 Calcana is welcome to the show. 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 then it's got good insight. So I'm glad to be here. I'm a big fan of your podcast. Gotta have something to rely on Jason. Exactly the insights. Thanks for joining me. 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

4:23ties 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 set 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 slash acquired. I'm a member. I pay 100 bucks a year or something.

4:51Well, 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. It's great. We hope that the whole podcast is good, but we The LP stuff is the tightest I have to say you guys put the most work into that and people will just pay for it. You want good content to exist pay for it if only all of our guests were like you Jason All right listeners Now is a great time to talk about a new partner of ours here on Acquired. LaGora, the agentic operating system that is redefining how the world's best legal teams work. Yup, 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. LaGora took that insight and asked the question, what if you really built something with that power from the ground up for the legal industry?

5:45So 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. And that's how you get features that customers love, like tabular review where you.

6:04drop in a folder of hundreds of contracts and it pulls every key term into a grid a lawyer can actually work with. Lagores Bed 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.

6:24And they recently launched LaGora 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. And LaGora works where you already work. You can use it within Microsoft Word while redlining or drafting. The early LaGora numbers essentially speak for themselves when they have a head-to-head pilot with their top competitor they win 70% of the time LaGora now has over a hundred thousand lawyers on the platform from 1200 legal teams in 50 countries and crazily they went from one million to a hundred million in ARR in about 18 months truly insane numbers and that is the real test

7:16Plenty 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 logora.com slash acquired and just tell them that Ben and David sent you. So Jason, you've talked a lot about growing up your childhood. So we'll do that briefly here.

7:45You're born in New York, right? Brooklyn. Brooklyn. 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. Love it. Tell us a little bit about your family and what growing up was like for you. Yeah, I grew up in the 70s and 80s, which was a fantastically interesting time to grow up as a young person. We were free range kids to the extreme.

8:15And Brooklyn was not hipsters back then. It was working class and connected guys and the hell's angels and cops and bookies. 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. People loved my dad John the beard and they loved his bar. And I worked at his bar, my two brothers and I'm older brother, my younger brother, Jamie and Josh.

8:45From a very young age, my mom was a nurse and she ran the emergency room in Brooklyn at Victory Memorial Hospital and then later ran the ICU. She's a nurse practitioner. 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 owned our house, but barely. We were always living month to month. But there was a lot of love and a lot of craziness growing up in a bar. I literally grew up in a bar.

9:14and made espresso for mob bosses, made bay clams for Tony Bennett, would go get cigarettes for the Coke dealer, would put balees in cappuccinos for police officers in uniform, coming in at two or three o'clock to have a steak or burger, because my dad would let them come in at any time.

9:37Sounds like not just a bar. There's more like a pub. It was a pub. Exactly. It was kind of like a pub. And the cops would come in anytime they want it, but usually they come in between lunch and dinner. And my instructions were just given whatever they want and just charge them ten bucks each. And they would proceed to drink four or five Irish coffees each.

9:59Did they order them as iris coffees or yeah, no there was the wink and then there was the wink, you know they they we were in uniform so they just wanted to have a cup of coffee hey cake and a cup of coffee and whenever I got the bookie already mereska or the the guy who dealt cocaine His pack of cigarettes or whatever they would just say here's 20 or here's a 50 sometimes or sometimes even a hundred could give me a pack give me two packs of marble lights I go out and get two packs of marble lights was two two dollars or a dollar fifty a pack and they say keep the change This is like the Brooklyn version of Bob Eiger's story with the chairman, Frank Sinatra, going out and getting him mouthwash. Exactly, exactly. And so, you know, 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 in a poker game when the bar closed at four.

10:57the fun began from four to seven or eight in the morning there had after hours, which was mainly cops and hell's angels and mafia guys and, you know, hippies. All playing together. Yeah. Yeah. Yeah. And I would come and I would do the Porter work at seven a.m. So I would come and sweep up the place on Saturday and Sundays when I was 10, 11 years old, with my grandfather, Reston piece. And we were the Porter's offense way saying janitors. And my dad would be there playing cards or whatever. Anyway, this guy got, he was in for two grand too large to my dad.

11:25And 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 was like 1984 or something. I don't know, no, 83, 84 or something like that. They were just ready to have video rental stores, but something like Star Wars would never be allowed there, maybe become five years later. Anyway, long story short.

11:55I 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. That's you. I thought you were going to say you started running screenings. No, that would be a better idea actually. But anyway, before Jason learned about marginal costs. Exactly. I was like, wait a second. How much is a VHS tape cost? My math teacher says a Calcanist stay after.

12:24I'm like, God, I'm gonna get pinched. And so he says, I know you're selling this tape. I said, yeah, because you think that's an okay thing to do? And it's like, no, I probably shouldn't be doing it. And he's like, 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. It's literally, I mean, When I saved my life, when I was watching Goodfellas, I was using this chromic extension called Siener that we invested in to watch Goodfellas with some fans of the show and I just tweeted and it was like group viewing, you know, like there's Netflix party and this is Siener. So now that I've reached home, you can watch Netflix with your family, whatever, so put on Goodfellas and...

13:11I was just watching this gig growing up and I was just having flashbacks. I mean, literally my life was like the first act of Goodfellas. Well, Jason, I'm going to deviate from our little outline here a little bit, but I know you're a prolific poker player. I don't know if semi-pro is the right word, but you play with pros, your friends with pros. A lot of you're investing patterns, sort of match poker patterns. Informed by? Yeah, so.

13:34Did that start here? What was your early approach? 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 a day, a Ressie who started the Founders Institute, just started a $20, $30 poker game. And myself, Scott Heiferman from Meetup.com, Nick Denton had come to a couple of games, Jeff Dodgers from Razor Fish, 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.

14:03No, it was like one of those card games where people said, what's better, a straight or a flush? And somebody had to look it up kind of thing. Yeah, you have the little card next to you on the table or you're sort of referencing it. Yeah, literally. That was like that. It was just an excuse. And we used to play down at a place called Forlinies, 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 Skydatin, was playing cards.

14:31my friend Kevin Pollack 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 want 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 I want to see Jason Gallagher.

15:00So I never went to Molly's game which he 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 deconferences myself bill girly mark pinkus and Sky date and we're all there and we say hey you guys want to play cards and we went up to I think was mark pinkus's room when we just took the folding tape we started playing cards and then we started hosting this game at the deconference which later became recode it became very famous is poker game and then we have a weekly poker game that everybody knows about here in Silicon Valley. You're just my best friends and Phil Helmuth and Dremond from the Warriors, Chimoff 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. And now you have a podcast around it. Well, Chimoff was just like, Chimoff was one of these guests on my podcast who...

15:56He just burned the building down and he nobody really knew who Chihuahua was until he came on my podcast and You know we started having them at the events and then CNBC got their hooks into him and now he's just like throwing bombs for a living Well, he gets like just incredible page views whenever he goes on CNBC and 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. Not your mouth. But I'm raising funds right now. 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 got to like step six feet back. The building down. Great. Cause this is the perfect thing to you.

16:45the media business. So when you go to Fordham, right after Fordham, you start as a reporter. So what draws you into the media business? Because to my mind, obviously you're growing up years and everything with that shape to you then. But starting in the media business is the wedge that brings us all to the Cali-Canis empire now. Yeah, so this is a very interesting thing. What happened was, I would go into Manhattan.

17:13I 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 hell's 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.

17:43probably too much. And I saw magazines, and 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 in New York. So you were kind of making me back then. Like 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 blog. 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 a parker game. I was doing a little phone freaking, which is like getting phone codes. Anyway, I was involved in a bunch of scams. Yeah. Well, the phone freaking thing was kind of scary because the waste sprint worked in the early days is you just dialed an 800 number and then it asked you put in like a five or six digit number and then you either got a dial tone or it went.

18:41It doesn't make 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 these are 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 before I was making 250 an hour, which was the minimum wage in 1987. I think then I went to 350. Then I got fired from that job because I had partitioned a hard drive.

19:09and created a hidden hard drive where I put a bunch of video games and I was selling video games and more entrepreneurial. Well, yeah, I was, I was a, I was a criminal. Um, I was selling word perfect out of the Fordham computer lab and I got busted. And then I started selling SPSS X or whatever that's called, like the 10 disc, like $400 statistics package. And this is like, yeah.

19:34Yeah, this is like a really bad idea because now I'm 17, 18. It's starting to get worse than Star Wars tapes. 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 happened. Z-I-N-E. And so zines meant you published,

20:02on photocopy paper and you called it a magazine and in tower records they had a section for zines and I used to go there and look at these crazy zines and 2,600 was one of them. In 2,600 they would just self print it, self publish it and it was just hacking stuff right. Is that named after like 2,600 BOD? Yeah it hurts. Yeah I think it was hurts which is I think the...

20:23When 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 and the city the city bank building and 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 Cybersurfer 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, holding blew up. And then I was like, the Silicon Valley thing's going to become something. So I started Silicon Valley reporter as a 16 page photo copy. And Fred Wilson bought the first ad in it, along with Jeff Dodgers from Race and Fish. No way. He bought an ad for Flatiron.

21:16for flat iron partners $250 and he bought four ads at once so he gave me a thousand dollars Wow advertising like their services as if you just put the logo flat iron partners and this is 1995 I got two people to give me a thousand dollars I printed it out because two thousand dollars and I just started handing it out of parties and I didn't understand how silly I looked walking around town with a luggage cart 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 razorfishers office I would go to site specific I would go to I village 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 So you're going to these early internet companies dropping it off and they would say oh you're dropping it off and I tell you I'm the delivery boy

22:07And 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 a CEO, editor, and delivery boy on the top. Because, and what it was, it was like, quite charming to people that I believed in. It's 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 hawkster or a hype man or a fraud, people bought 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.

22:34Because I just wanted to be famous. I just wanted to be powerful. I just wanted people to know my name. It's so interesting because it's so akin to the early days of blogging. I mean, it's just analog blogging where 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 literally what photocopy paper. 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.

23:03This is a full page photo. And then a guy named Carole Martesco emailed me because he 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, et cetera. 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. That's how much of a cost. He says, of course, $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, 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, Kerr, Omar Tesco, shout out. I was still friends with this day. And he basically mentored me on how to do that. And then at a certain point, my assistant, Linda Miller said, John Winter called. And I said, okay, yeah, you know, from Rolling Stone. And I was like, yeah, it's like you're two of the magazine. And I was like, okay, great.

24:03And then I went to lunch and then she came back and she called me on the back and I was like, no, I thought I'll come tomorrow. I come back the next day and she goes, did you call you on the back? And I said, I don't want to do any press right now. And she goes, no, no, he's not a journalist. You're on the back of a creative Rolling Stone. And I said, oh, he wants to meet with you. And so I went out by a metal young winner and he had all my magazines on his table and said, hey, I want you to come work for me and do a magazine with me. I wanted to do like a digital version of Rolling Stone. And I said, no, I don't want to do my own thing.

24:32I was up in his office and he had marked what that made you famous like why wouldn't you do that? I also realized I know it realized that would be a number two and I never wanted to be number two So it's about the fame and the power or I might it was 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 up my credit cards. I was on Charlie Rose 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 I reporter was. And I could get into any party. And then I made a list of 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.

25:23Power. The money list is still doing that to this day. 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 the Oats just gave the key notes. So it's pretty funny. As you get in all this power, what's going through your minds? Like are you are you already starting to think about more?

25:49Are you thinking about, I partly, this into investing or I part of the exit. Like, what's... I wanted to be the next media mogul. I wanted to be Eisner. I wanted to be... Like, Eiger. I wanted to be... Oh, it's... 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... This is a little thing on the side. ...the Warner days, this is... 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.

26:19Barry Diller, something like that. So you end up selling Silicon Valley reporter to Dad Jones, right? Yeah, it kind of collapsed and we wound up selling, I got two years of salary, but the year before Alan McClure from internet.com, it offered me 20 million dollars for it. And I owned like 85% 90% of the company, so it was like one of the most difficult times of my life because I had my chance to be rich and then I was poor again. Was it?

26:43The dot com crash the 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 the 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 you had all this power And it was gone. It was gone. Did it disappear? Did it really disappear? Well, you know, it really was trying for me because everything I had done had gone up into the right and everything I touched turned to gold. And then when you have them, I just 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 it a kryptonite in my shoes or something? And it was a very humbling experience for me and it made me really angry.

27:35I remember vividly, I just felt very angry at the world and at myself, we're not taking that 20 million. So it wasn't just angry about what was happening. It was like, you were specifically angry about passing on that. I was angry at passing on that. I was angry that the market collapsed. I was angry about 9-11. It 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 and I'm going to dunk on everybody.

27:59And 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 Rafad Ali.

28:22Who's doing was doing this paid content that will work and I had admonished him because he started it when he was working for me I was like listen kid. I didn't realize her father worked for you Yeah, it was one of my writers. I think I was a second job. He had he had worked for inside.com and then for me and he had only Inside.com domain at one point so there's a whole sort of history there of who got to own inside.com at the end of the day I could tell that story to you at the end but anyway, I was like and then shenny jardan 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 and add on their blogs exactly so i was like wait a second these people are working in their underwear they have no editor and don't on me the right writer and editor is uh hindrance they're taking out what's special about what the person said

29:15This is like taking out the production. It's like Bob Dylan just on stage with the guitar It's better when it's not produced It's better when it's acoustic and there was that thing that I 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 want to throw the other records away that was studio produced And I said, blogging is gonna be a thing. So I started looking for other blogs, and this, I knew this kid, Nick Tenton, who started first Tuesday, and he started Glocker. I said, hey, Nick, you know, when I have lunch, when I'm for lunch, I said, think about doing a blogging thing. I think this could be big. If somebody did it for business, it would be huge.

30:01You're doing this gocker, gosh something, 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 Calacana is bringing his unique brand of like whatever to it. Corporate sellouts. Well, that's what he said, because I was like, you know, this would be an advertising juggernaut, because 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 Valleywag exist at this time yet? No, no, no, Valleywag created much later. It was just gocker.

30:30I mean, I've worked at the Wall Street Journal. I mean, you did too for a while. It's a wonderful organization. There are a thousand people in that building. It's crazy. 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 Denton's vision for this. And I was like, are you going to do more? And he's like, yeah, we're doing this. We're going to do a political one, I think. And we're going to do this one on gadgets. It's like, you know, like the fetish thing in wire magazine. We're going to just make that into a whole thing. And I was like, oh, that's interesting.

30:59So he writes his blog post, trashing me. And I was like, you know, I'm a pretty aggressive guy. And I was like, so my partner, Brian Alvy, who I convinced to do this with me, is 2003. None of us had any money. We're doing it all for free. The economy was flatlined. I said, I'm going to destroy him.

31:22Which it turns out you were not the last person to have that. No, no, no, I was not the first. I was the might've been the first, but not the last. I said, I have to destroy Nick Denton. How am I going to do this? And I said, oh, I know talent. Nothing worse than losing talent. Elizabeth Spears. She's writing, she's writing Galker. I'm going to make a run at her. And I had heard that he was paying the riders $1,500. And the MacBook Air had just come out.

31:52I 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 to par that somebody took in the early days and she's looking at me like, I am the anti-Christ. And I was like, you are a unique talent. Nick Tentable never give you equity. I will give you equity. You will become a millionaire. I'll 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 movie you could ever make, Elizabeth.

32:20magazines are going to die blogs are going to take over. There's no way magazines can ever keep up with blogs. Whatever they print is going to be old news. And you're already proving it. You're number one at blogging and you're going to become number 500 out of magazine. So she wouldn't do it. And then shenny shardans 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 point. I don't want to do anything commercial. And I was like, all right, that's fair enough. I said, who should I target? She goes, oh, you picked the wrong target. I said, what do you mean?

32:49Nick's not making anyone in Glocker. Glocker doesn't make anyone lose his money. I was like, okay, tell me more. She goes, 100% of the revenue is 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 he 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's like a pretty hot ticket. And I asked Peter to come have sushi with me.

33:20and his wife, Joe, or his girlfriend at the time. Can I bring my girlfriend? Of course. We go there, and I'm prepared to knock their socks off with his omokase, and I said, you guys have anything in terms of die and we're vegans. I said, okay, yeah, that's no problem. I said, give me a second. I go back to the guy, I said, listen, I'm trying to close this deal. It's really important. They're vegans. He's like, don't worry about it. I'm right back.

33:45He runs to the Korean grocery on the store. He comes back with two big shopping bags full of things. And he makes them the most amazing Omokasai with vegetables. 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.

34:14and he goes, well Nick said he's gonna give me acquities and he'll never give you equity. When did he tell you that? He said, it 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. That's great. He said, but, you know. This is so great, because by the way, at this point in time, this is, I'm probably 17, 18, 19 years old at this point. I'm reading his moto every single day. And I always wanted to know, What happened? How did Engage have become better? I never knew. This is the story. And he says, oh, my girlfriend, Jill made a logo and Jill made the first Engage logo. I was like, great. He's like, can we pay her for it? I was like, sure we can. And I was like, what is she charged 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 in. How'd you get to know Mark? I had no mark because I had written broadcast.com is a billion dollars worth of hot air and looking at a reporter.

35:13He reached out to you. He 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 don't. And he's like, well, why don't you wait? And then revenue went from 10 to like 60, you know, like quarter of a quarter. And I was like, okay, it's not a billion dollars in hot air. And I did a me a cope with kind of situation. Anyway, we became good friends, Mark and I for a long time. And he put 300K in. We started a blog maverick for him. Brian Alvy came up with the name.

35:37Brian Ava came up with all the good names. The best collaborator I've ever had in my life. And, uh, and Peter. And, uh, and, uh, so Peter said, listen, you know, I just, I feel really bad about the stuff with Nick Dunton. 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 guilty. He robbed you over your vision. And we're going to take it back. And he said, yeah, yeah, you're maybe you're right. And I was like, yeah, because I said, I, I've been in fights.

36:03And, you know, if somebody takes a swing and you know, like somebody gets a, if somebody's soccer punch is you, uh, you have to teach them a lesson, um, so they don't do it again. Cause if you don't teach them a lesson, what I learned is there 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 soccer punch that guy. That's how powerful the beat down has to be. It can't just be retribution of one for one.

36:33If 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, but this is literally what I saw on the streets of Brooklyn in the 70s and 80s. So I said, when are you gonna tell Nick? And he said, well, he's been working so hard for like a year or 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 gonna take his first vacation. I said, oh really? He's like, yeah, he's going down to Brazil or whatever. And all these famous people are going, I said, when is he going? He's like, it's going Sunday.

37:03I was like, oh, what time is he leaving? I don't know what time is leaving. I said, okay. We looked up online, like flights to Brazil, whatever. Couldn't kind of figure it out. I was like, all right, well, listen, I want you to write a blog post about this. We're launching the site at 2 p.m. on Sunday. And we literally launched the site the first day of its vacation. He landed with his people going, his motto has no blogger. We have all these advertisers and this is a competitor. Oh my God. And that was the approach I used to take to competition. I don't do that anymore.

37:34Well, by the way, and the post script to that is dented. 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. You can't praise over that. So how 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.

37:57Kotaku, then I launched auto blog, then he launched Jolopnik. And when we were ahead to head, we always had three, four or five times the traffic is him. But it created this rivalry that everybody followed. We can cook Pepsi. It became, you know, oh yeah, pick media company versus media company. And everybody was following this great competition between this brush, Brooklyn kid, and this aloof, you know, quite probably made you get made you both better. Oh, I mean, it's incredibly much better. But you know, it was like literally this like quietly gay, you know, very understated.

38:27Brit versus this brash Brooklyn Bulldog, and it just played really well in the pressing. You can, if you type Denton, Cali-Cannison to Google and look at some of the posts from Backman, it's hilarious. And it was just a good time. But you can reach out to me, and he said, listen, I think we shouldn't have a, you know, Jason, respect, respect for what you did there. I understand, you know, Peter, past of luck with Peter, and we went for a cup of coffee, whatever. And we're sitting there, and he said, I have a proposal for you. And I said, yes, yes.

38:57I think that if we're going to have this spirited competition, that's great. Good for the game and all that, and you're a worthy competitor, and obviously you've been able to... You're just waiting for the knife to come out. Well, yeah, I'm just like, okay, this could escalate. Yeah. And he said on proposing a no-poach agreement.

39:18And I said, what does it mean? He goes, well, just, you know, there's no need for so many writers out there. We're not enemies. What we're fighting against is the magazines and the newspapers. You know, we're up against the New York Times and that's enough competition for us. And I said, you know, that makes a lot of sense. So we will, we agree to not post each other's writers. 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.

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41:24Well, Jason, I got to tell you just a quick personal note and this will surprise zero long time 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. Oh, two, T-U-A-W. Yep. There's an interesting story to that. We called it the Apple Weblog and Steve got upset. No way. 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 us people to call we had a pretty close relationship with Steve or at least Peter did and you know Steve responded to our emails always realize the power of the media Well, yes, I mean Steve was the master and I I'd spoken to Steve in person two or three times and over email You know half a dozen times during the in gadget 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

42:22You 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, TWA. And then just build a logo and I think Jill Farronbacher, you know, Peter's now wife and 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 TWA and called it a day.

42:40Well, that was kind of I think that was Brian Alvie's joke is like it sounds like it's French so let's put it as like an accent to grove on top of it And I was like sure let's troll them and we do it's just like a lot of crazy stories like that and Long story short that company lasted 18 months. We got sold it for 30 million dollars It's a well and this is all of web-logs ink. This is all the web-logs ink. We had a hundred thousand dollars in revenue to date and probably two hundred thousand looking forward So depending on how you count that they paid three They played a big multiple. But the real question though is like looking back now, was that actually a good idea to sell? 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 millions to artist and once you get that under your about, you're dangerous. Nobody can stop you. I mean, I was already dangerous because I didn't care. But once you get the cash,

43:34then you really have the ability to not get. Right. So it's like, if you hadn't sold and that we're still in independent company, that would be worth a lot more money. 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 it in the bridge financing and then some amount went to Hulk Hogan and Peter T.L. and then some amount got left over. I think we wound up netting about the same. It just took him 12 years and it took me 18 months. Right. But you know, you know, what I was...

44:04You got to start writing your next chapter. Exactly. The great thing about Silicon Valley reporter crashing and burning was I learned very early on that I was more than the brand because the brand still can report against so big and I was so identified with it that I started people would call me the Silicon Valley reporter that was like what people would refer to me as.

44:28Because of 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 to Gospel and this Yeah, he just kept reiterating and then he started collaborating with Mark Knopfler of Dire Straits and did Empire of Alaska and You know, all these other really infidels in these very interesting albums. And I had seen Bob Dylan maybe 20 times, 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 never look at my prescripts, the amount of press I got in the 90s 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,

45:23I put all that press in boxes. I taped it up 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 looked at myself and I said, you know what? Kurosawa did all those samurai films and then he went into noir. And then noir stuff was better. And nobody even knows about the noir. You know, the film noir stuff he did. Hi, hello, Shredog.

45:53You know all this kind of stuff. Is it after then the next chapter you get you get money? You're back in the game after. I'm in the game, baby. Is that when you moved to LA? I had been living in LA when we start right after we started weblogs thing. Yeah. 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? No, fame wasn't. I really wanted to build things. I had gotten into the mode of building.

46:23Not to say empire building out with like Silicon Valley types. 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, 60, 70% of these things fail. Don't worry about just start 304. You're going to have a head. 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 Island reporter is. They don't even know anything to stuff. Nobody has any sense of history, but people are all caught up in their own history. I for sure had a Mahalo account. Yeah. I mean, Mahalo did really well. I mean, that's a whole nother story, but yeah. That's another one, right? Well, 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.

47:12It's like, who cares? Just move on, next one. We'll get there, but I do want to talk about the Mahalo Pounce Twitter, that sort of Tumblr. Let me put a pin in that and David, keep running with your line here. Okay, so this is a diversion, but we sidetracked, but we got to cover it. When you're in LA, how do you meet Travis Kalanick? Well, when I was doing Silicon I reporter, we had started an edition called Digital Coast Reporter.

47:40And I had interviewed Travis when he was doing scour, which was his first company. And he got sued and all that stuff and he told the famous story. And that was the night allegedly when Michael Overtz's people came and we're 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 tuition. We'd always been friends and we'd always liked each other. And that's how I wound up investing in Uber because he was raising money for it. He wasn't going to be the CEO.

48:07He was like, hey, I'm doing this company. It was like a, you know, Ryan and him and Ryan was CEO. Ryan was going to be CEO and then I was going to invest a little bit of money and I was helping Ryan raise money and then he said, you know what, I'm going to be the CEO. I said, what happened with Ryan? I was like, oh, it's just a little shaky, whatever. And then I just made it as the first gap at and I introduced. I think first round and definitely Cyan were at the open angel forum. The little event I used to start where I matched angels and. So at this point, you're running Mahalo at this point. Yep.

48:36So I actually didn't really was Uber the very first scout investment. I think it was the third. I think I had in the first seven There were three unicorns and this is some type of scout as was a coil scout I had the first seven Uber thumbtack and data stacks so three Companies three unicorns one of them public deck of corn We'll see about the other two, but I didn't know the two got a chance to go in public too And so 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 look on that? It was 50, 50. So it's 50, 50, basically splitting the carry, the profit. Yeah, put the car in. But the profits, yeah. Yeah, it's crazy. They since dropped it, I think to 35, we're 30, like a normally high carry. How did this happen though? Like what did you go to rule offer? Did rule offer? I had, I had,

49:32lobbied Sequoia. I had emailed Sequoia and lobbied them to invest in my friend's poker game. Zingapoker. Sorry, what is that? My friend created a virtual poker game called Zingap. And our dog, that kind of thing. And I invested, I said, hey, you should invest in this and they couldn't get there.

49:54but my other friend, Fred Wilson. You were a portfolio entrepreneur. I was a portfolio company and I said, hey, you know, this Twitter thing's gonna be big and this thing's gonna be big and I was pushing rule off and I have an email where I told Michael Moritz and you have to get the Twitter deal. You have to get the Zingadiels. These are very important companies. And then my friend, Fred Wilson. What did they say? 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 they're exact objections.

50:24Both of those cases, Fred Wilson had invested and actually introduced me to Mark Pinkis and Mark Pinkis 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 about $11 million valuation to $100 million valuation. Wow.

50:49And this is in 2006? Yeah. And Mark Pinkerson and Evan were like, how did you go from 11 million to 100 million before the product lunch 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 helped me get in business. His wife, Joanne, worked with me at Silicon, our border.

51:18And, you know, and also Joanne Wilson, his wife, worked with me at Silicon Valley, and the reason it was so successful is she was the salesperson and she was, I mean, it was two bulldogs, like she's a tiger. And she's now a great angel investor herself. Absolutely, yes. And just one of the great collaborators I've ever had in my career. And anyway, long story short, I said, listen, you know, you're picking between Fred, who's like the up-and-coming hustler, who will work hard. And, but, you know, he's a East Coast. And a lot of people, you know, are, Fred thinks Sequoia's the goal center. Fred would tell you to take Sequoia's money. But I think Fred is great too. So I actually think it's a coin to us. 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 broke up and now he's doing this launch festival on his own.

52:17and rule off came off this idea, what if we raised like a three million, two three million dollar fund and we just gave everybody the ability to make 2550K 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. Obviously the trick is do what you did and just raise your next round before anything even happened. Well that works too, but you know the idea is like if your venture fund did not follow on, you were damaged goods.

52:46and nobody else would. And the higher profile, the fund, the higher profile, the signaling risk. So Sequoia was acutely aware of this. So they just said, the Scouts program, we wouldn't announce, you know, beyond 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 Koretsu forum, which was charging people $500. So I went to work with them. And they got really upset and called Michael Moritz on the phone and told them like,

53:14Who is this employee of yours? He's like, not an employee of ours. Well, he said he's gonna kill the, he's gonna kill the Karatsu 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, you really love these situations where you, you take a mild mannered Brit and you really angry in a way where they have to have a talk. No, no, Michael Maritz was not angry. He's like, well, why would you tell him? I loved him. I'm just curious.

53:39Moritz is cool as I use 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. That was the end of the book. Oh, it's great. So great. So anyway, I started open angel forum and I just started, you know, thumbtack, style seed, data stacks, all these signposts, all these great companies just came. And Uber came. And Uber came on the spot myself.

54:09Sokko is there, but Sokko knew Travis before, and Siam Bannister invested in them. I introduced Siam Bannister to them, Taken Uber, she's always been very gracious about giving me credit for that. And I'm at 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?

54:26A success has a million. Millions of it. Five. Okay, so all this is going, what's going through your head is this is happening. You're running Mahalo. Mahalo's super high. Yeah, I mean, they anointed me. Sequoia anointed me. Now I became dangerous, because now I wasn't just East Coast anoint, I was West Coast anointed. You understand? Yep. And nobody really had ever done that. That was a very unique thing. And I knew it. I think a lot of our audience probably has not ever heard of Mahalo, so fill us in real quick on. So anyway, I had this idea.

54:56I 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, it's a argument about that.

55:14I had run into Moritz one time at like a conference. He wouldn't remember me. But I emailed Mike 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. I was gonna ask how many minutes to take to rest. John Doer, somebody on his team got me the next day.

55:41I was in both their offices next week, and also Mark Cuban said, because I think when we sold, we turned just 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 see it as 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...

56:01You know, very more Cuban thing to do. Oh, because here's the question. Did you actually have the idea or did you just say that? 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 down daum.net and comprehensive search in Korea and in Korea down on the blogging company and The picture hosting company and they when you did a search they would show pictures There's your links pictures and blog posts on one page and so I made this comprehensive search and I said it's gonna be called 20.com The top 20 links for any keyword and I went into the meeting and I put three pieces of paper on the table

56:56And I don't think I've ever told the 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 Maritson rule off pointed to them one and they turned it over. I said, turn it over. It's a 20.com. I said, turn the over to over. Well, I did it again. I said, coivocation.

57:21And they picked mine again. And I said, they said, 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. Am I going to say, oh, that's a great idea. What are you looking to do? I was like, I want $3 million for 25% of the company. And he said, OK, work with Rolloff. And he walked out. And he was on the board of Google. And he's like, I can't do this, but Rolloff can. And it's not a competitive with Google. It's a wiki, whatever. And that was the start of it. And then my friend Elon put some money in.

57:51Uh, he was just casual working a rocket company. He just called me. So I think you're smart. I'll put some money in it. And then uh, Rupert Murdock 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 at $10 million in Google Adsense revenue. And then Matt cuts, uh, felt like we were getting too big and eHow was getting too big.

58:15There was also Cosmix, right? Yeah, Cosmix, Wikihau. There was a whole cohort of us making content. And let's pause for a minute, 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 Lynxbam. 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 US Digital Service. Well, what would happen is, our pages were so good, that coi 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 our Google's roadmap five years, 10 years before they got there. Because if you Google coi vacation on Google, you get that now. So I was five or 10 years ahead of them, and they were going to do it machines that

59:12Marissa said, I don't think Jason's right. We had this like debate at a conference at one point. Somebody asked her about my college. I don't think humans can scale. We're going to do with robots. Anyway, then they basically took 90% of our traffic away. And the punch line 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 Brinn, 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 this big public spat.

59:39And they're like, yeah, you know, we don't know. And I was like, well, we're partners. And Matt Cuts is like, we don't have partners. And I was like, I forwarded him the email from the EdSense team that said partner meeting. And that they, you know, partner lunch and partner this and part of that. 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 he helps write what they did to Yelp.

1:00:08It was the same thing. It 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 not $10 million runway. We're making just a lot of money every day at the peak in AdSense. And this is all hunky-dora. I was like, they'll never shut us off. We're sending, we're giving 30 cents of every dollar to them. Yeah.

1:00:33And I was wrong, you know, they had a long game. They just didn't want mahala.com and other things to exist. So they killed us. And then I pivoted to Insight. And it's still going today, 12 years later. And you know, it's actually doing really well for email newsletters. What's old is new again. Exactly. So what's going through your head at this point time about like, okay, what is your next act like? Well, the scout thing I didn't take too seriously. I just thought it was a fun diversion. And then they got about a, I don't know, halfway through the program and rule offset to me. 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 fun, we might not do another scouts thing. So, you know, you got like a million left in the fund. And I was like, oh, hey, you're up to tell me the buffet zone. The fund is Uber Stripe Thumbtack. Data stacks. Data stacks. I mean, that fund is the greatest fund.

1:01:30in Sequoia's history on a percentage return basis, I believe. I don't know that for sure. Not a cash though. Not a cash. On multiple cash. On multiple cash. On multiple cash, it's definitely in their top five, I would think. And they're saying, we don't know for you to do this again. 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 we were obviously, if you want to make some more. So I did 19 investments, I put 700 to work and became more of over 100 million in total, largely due to an Uber. And then my friend Neval 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. I, you know, like, nobody's going to invest online. It's all in person. And he's like, yeah, I just agree. And I was like, yeah, I don't, I don't know Neval. 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. You explained it to me. And I was like, I don't understand it. Explain it to me again. Explain it to me again.

1:02:28And then he sent me a link and it was, you know, angel.co slash Jason says syndicate and it said, you know, send it your syndicate here and I filled out the stuff and I tweeted it. And then he called me 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 said, I didn't want you yet. It's launching on Monday. And I said, oh, I'm sorry, you want me to take that? And I said, no, don't worry about it.

1:02:49It's not crunched, got the embargo, but they're upset. I was like, nobody's gonna see. It's on Twitter, nobody's on Twitter. And it's also so interesting that like in your head, you're like, this is, 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. I'm not saying I'm the smartest guy in the class. I never said that. That's not my clue.

1:03:13I'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'm definitely been lucky and I'm definitely going to hyping things. So, I mean, that's why the Vals sent me the link. Anyway, a bunch of people joined Tim Ferris launches him. I don't think we should glaze over this.

1:03:35The set of people you've already talked about clearly, there's something special about the way you build relationships. I mean, you're fun to spot yourself as a hustler, as someone that works hard, as someone that is extremely driven, but lost. And 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. I think enthusiasm is contagious.

1:04:03So I've always been very enthusiastic about 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 Moreilie 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, do she? It is the Land Room helicopters. Like, do you think so?

1:04:25It's 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 helicopter from Palo Alto. He's like, you're probably right, Jason. I totally acknowledge the library. He was pretty funny, but he didn't literally have them clear the field. So he could land his helicopter. He was taking helicopter lessons at the time of food. So I'm not speaking out of school. He literally landed his helicopter there. Anyway, Tim Morales 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,

1:04:55If you tracked very little from the network you're building, you do really well. You don't need to extract all the value. Yeah, it's like the Bill Gates platform quote. Something like that. Yeah. But he evolved. He said it better. We'll come to it. 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 with in gadget, I was at Sundance. And my friend, David Sachs, was producing a movie there called Thank You for Smoking. So we were all there. I just saw Weblogs Inc. Elon.

1:05:25myself sacks or hanging out my wife and his wife at the time and sacks his new girlfriend is now his wife and what Mossberg is there and he says hey let's have lunch because he knew I was there I was like yeah sure and I was like hey you know let's meet over here I'm gonna bring my friend Elon he's like who I'm like Elon Musk he's doing this like thing whatever and you know what Mossberg was very big there 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 them. You know, what was very sensitive at the time I 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 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 make my friend Elon. So you're good at, I was always good at just connecting people and meeting people together and just hanging out with people. Like my bookage in John Brockman had introduced me to Sam Harris.

1:06:23Sam was on my podcast and he did like a AMA from a hollow. And they say, how do you do podcasting? I was like, you know, you're a bill for podcasts. I was like, absolutely, you're a bill for it. He's like, what do I need? I'm like, a guest and a microphone. He's like, oh, I was like, he used my studio. Anyway, I convinced him to do a podcast and now look at the rest of his history. And I introduced Sam to Elon. And then we all started talking about AI. And Elon is your Sam to the concept of AI. And while this AI stuff going on, the book's super intelligence and all that.

1:06:53And then the people who write Westworld, Christopher Nolan, 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. 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, we're not doing playbook this episode, but this is the little That's the feature many playbook just always by dinner. Okay, so I got to ask the that playbook that mindset that wanting power and Connecting people yeah as mahalo is you know post panda Yeah, the panda is the update that Google that yeah Why do you not go join a venture capital firm and become a traditional venture capitalist self-awareness? Yeah, I mean I can't have to be a VC as we all know well

1:07:52Here's the thing. It's called the 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 gonna be- Right, right here, it was about Dylan, not like Eddie better. 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 want to keep it small and authentic and true to what I want to do. And 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.

1:08:42as the top ear funnel, the only real angel list co-existor competitor. These things are not really competitors, we think of them as really co-existors, but you know, we're the number one largest syndicate in the world and Angelist is the largest collection of syndicates. But if you took the top two or three syndicates together, they would be smaller than ours on Angelist. And then you look at our program, like really only people who compete with Angelist had, with a Y-combinator heads up, like the only reason...

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1:10:53So 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 slash acquired and 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, I am not joined a band or I'm sorry, at this point in time, I'm just playing through what's in your head. You want to be a solo artist, but you also deeply understand returns to scale as you're thinking through.

1:11:20this 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? 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 said, Hey, Jason, check this out. You can attach a file.

1:11:50to 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 sink your iPod on your Mac to an RSS feed that then put it there. So the idea was you would plug your iPod in a night to sink and to charge to your Mac and also in podcast you would download at night all those things and when you got on your commute, you'd have a couple podcasts on there. And I was like, wow. And then they could invent Steve Jobs to add it to iTunes to iTunes. And there's a famous clip of me talking with six or seven. Yeah, and there's a famous clip of me.

1:12:46talking to Steve at the de-conference and asking him a question about it and I asked him about making money if he'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 left. But I just said it as a joke like, you know, why is this? You know, because I did talk to a money email. And so I thought it'd be funny to say, you know, like the email we always talk about. I mean, the whole audience cracks up. It's a very funny clip. But anyway, I did the podcast because

1:13:15I just thought it would be fun. And to me, it was just a fun way to promote my friends. And so, you know, I had Brian Alvion, my longtime collaborator as a first guest. David Sachs came on earlier, 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 they're like, hey, we love this podcast thing you're doing. We want to tell you about something secret. And I was like, what is it? 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.

1:13:43And he's like, well, anyway, we want to advertise on your podcast. This is 11 years ago. And I was like, okay. You hadn't thought about, you hadn't put two and two together. There was no advertising in podcast. It was just like, it was just a thing. But of course it was just like when you're starting Silicon Valley reporter, web library, it's the same thing. Anytime a new medium comes out, I assume it's going to work. This is my big trick in life. Whatever 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 gonna work. I'm gonna go full-bore as if it's going to. When podcasting him out, I want a full-bore. Whatever everything comes out, if I'm interested in it, Twitter, the same thing, I just want a full-bore on Twitter. When does that not work? Oh, God, probably more times than I can count, but I mean, it's... But it doesn't matter when it doesn't work. Yeah, I mean, I have a Tumblr, you know.

1:14:34There's a bunch of sir path comm friend feed there was a bunch of other things but if you take the Robert's global relentless enthusiasm like spastic like oh my god, this is gonna change every Google buzz Google plus you know like I was all in on their 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 and asymmetric returns yeah 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, you got there early, you're gonna have a head start on everybody else. And then it just worked for me. And then they bought, they were like, how much of the ads? And I was like, um, uh, $3,000. And I'm like, okay.

1:15:16I was like, yeah, but you have to back 10 and they're like, okay, $30,000. You just sent me $30,000. They're like, what is the ad? I was like, I'll just talk about Bing. And so they literally just pull up Bing and I'm like, hey, check out this feature. Check out that feature. Thanks Bing. Bing, Bing, Bing. And then we'd have to the end of the ad. They're pretty fun. They're very fabulous. So great. Yeah, we just goofed off. And we'd have puppets on the show. We just...

1:15:36It 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. And what's the listenership on this weekend startups now just to give people over 200,000 per episode? Yeah.

1:15:52Yeah, so you guys are running my tails. It's a niche podcast by design. 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 Joe Rogan has taken the same approach, the same Howard Sterling-like approach as you put the record on, as long as it's interesting you go. And we have three ads slots, and we sell them out every year, and it does a couple of million bucks, and that's enough to pay for a seven-eight-person team that works on the podcast now.

1:16:18That's awesome. And how does that play into your angel investing? So take a sample. Yeah, I mean, yeah, I would say on the podcast, hey, you know, here's a company I invested in I'm having them on the podcast or in the case of calm.com somebody had told me Alex was like a genius and I was like, why? And he's like, well, it did the million dollar homepage. I was like, Oh, that was genius. He's like, yeah, he's doing meditation app. I looked at it. It was a webpage where you went and I just played a meditation in a loop.

1:16:43And I was like, yeah, I'll have them 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 on the episode, he said, hey, can I put 25K in, you know, for like 1% or 2% or whatever. He said, yeah, we talked about it. I did live on the episode. 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.

1:17:11My expectation was maybe another 25k would come in or 50k because they have like, I don't know, like, I don't know, 100, 200 people had signed up, so I was like, yeah, and $328,000 came in. And the company was worth 4 million or 5 million at the time. We had a six or seven percent 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 composition.

1:17:38And 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 calorie. 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 sort of tale, 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.

1:18:04very 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. 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... That's your nightmare. It's literally my nightmare.

1:18:33I want to make an investment because I look at 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 freaking sense. So anyway, consensus equals death in the early stage. Consensus that later stage equals protecting downside risk and due diligence and all that stuff is very important. I get it.

1:19:01Certainly. 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. 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.

1:19:32But every one hundred hands you could win a million dollars or ten million dollars So there was uncapped upside somebody just gifted nine hundred thousand extra dollars or nine point nine 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 the world dead money. People who are easy to pick off. It's like for the pros for Phil Helmuth, it's literally like, if you started the NBA finals and the Warriors had to play against the high school team, we're like, well, we're just going to win a lot of games here. It's the only way to get asymmetric upside and poker. 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.

1:20:32investors, 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. And they had $500,000 in their bankroll, and they gave 250,000 of it to their daughters, sonoray sisters, boy for ex-boyfriends, 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. That's the reason they're going to exist. And they put the $250,000 and the product never gets released. They give that $250,000 to Devshop in Estonia that never finished.

1:21:24They asked 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 We're like in poker like betting me to go and all in before the flop Yeah, before you look at the cards, you're just like, I'm gonna sit at this table and put it all in on the first hand, which I know some people who do that for fun. For people that are not professional investors, it sounds ridiculous to dumb it down this far, but even if you're only making five, six, seven angel bets and you're not really creating a 12, 15, 20 company portfolio, it's mathematically the same thing. You're taking way too concentrated of a bet.

1:22:07You need to really hit 20 or 30 or 40 in what I've seen in angel investors are 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 is being 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.

1:22:36Okay, so this is what I want to I want to go deeper on yeah, because I think this is a really important insight here How do you square the what you said a minute ago about Consent set the early stage consensus kills because you want the crazy stuff you can't predict right with this aspect of you need the high quality like what is the signal in the quality? Yeah, so would I?

1:23:00teach, 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 now, most of you 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 want to learn a blackjack, sit at the $1 blackjack table instead of the $100 I hand.

1:23:30because you 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 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.

1:23:5190% of the Trishian in startups comes from 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 two 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, how many at the table and you want to play 910 suited? Okay, maybe. If you've been playing for 10 years, but you don't want to take those kind 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, five times a calm, three, four, five times in Robinhood. Even these outliers, Airbnb, you probably have four or five chances to invest in Airbnb as an angel investor.

1:24:41It'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 periods, the deals close 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.

1:25:08Well, especially now with safes and not price rounds, like, it's rolling. It's not. It's super rolling. There's one thing you said that I think is really insightful when you're not Phil Helm youth 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 that? Yeah, so I can take it to the background. It was very simple.

1:25:37I 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 didn't love enough. 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.

1:26:02Then 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 and I found out that.

1:26:21Phil Jackson, who I'd 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 for me in Brentwood. They're studying. They have a program. They're teaching people this. Oh, they're studying it on PTSD soldiers. This is the future.

1:26:49But unlike yoga, which also started in Santa Monica, this could be delivered through your ears. Wait a second. Yoga, you have to do in person and yoga is everywhere. But meditation is delivering your ears. If this does work, and it becomes as popular as yoga, there could be 100,000 people paying for this. It could be like a $10 million a year business. It comes with $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.

1:27:19and Apple allowed subscriptions. And when I think we invested in, when we invested in comedy, I think they had done 10,000 in revenue, you know, something a month doing. Okay, so it was a post revenue startup. They had post revenue. Yeah, yeah, they did. But with Robinhood, they didn't. Robinhood 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 has an angel investor when you hit the J curve. It's so painful because you think you're an idiot. You've deployed all your money. Nothing's breakout yet. And you don't have any. You can't keep investing. Oh, and half your portfolio can't raise money and 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.

1:28:15Travis calls up and he's in six cities and he's closing around with men low at 300 million. And you're like, wait a second, 5 million times 60 and holy. That's a lot of money. You start, you start, oh, whoa, this could work. And that's when you, 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.

1:28:44from being risk averse and outlier averse 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.

1:29:0429 nights in a row at poker, but on the 30th night, you hit a 5,000 X or a 200 X. 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. Correct, Amundo. 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. To me, that seemed as like a really good mental trick to be like, it's not a loss. It's a failed experiment. Correct. And this is why I started the launch accelerator three years ago. We have a hundred companies I've gone through. And I basically was like, what was Paul Graham's original idea?

1:29:51Oh, six or seven companies. Great. I'll just copy that, seven companies. And Paul was the draw, right? And now it's the legacies, the draw, programs, 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 seven percent of a six percent of preferred for a hundred K, which is a $1.7 million implied valuation. So we'll go with that.

1:30:17We'll just start accepting seven people at a time and deploying 700K at a time. But then I added something which was, you know, YC, imagine if YC and Angelless got married or merged. What would that look like? Well, that's what I had. And I had left Angelless and I had started the syndicate.com and I took me a while to get that domain name but I got it. Covered it that one. I'm a domain name coverer. I'm a brander. Anyway.

1:30:44The point is, I started saying to people, I'll put in 50K, the original deal was like 50K for 5%, I'll put in 25K, for 5%, that 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 as Y-commoner at the time. So then we're betting on these for 1.7, you know, rather up to $2 million valuation.

1:31:12And then one of the companies raised around 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, yeah. What? I was like, I introduced you. So I called up those people who are doing the rounds and I read them the riot act. I said, I introduced you to the company. How dare you try to muscle me? I said, you're swinging elbow at me? I said, I'm the point guard.

1:31:41I passed you the ball. And now you're, you're, you're not passing the ball back when you're 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. 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. It's a hefty pro rat on my friend.

1:32:11Not if you're Jason Calcana's. And not if you're the founders. It's a feature, not a bug. Yeah. It's a feature for the founders who we work with because they can start their fundraising with me as an anchor. And they do. And do you, so do you pick winners? Do you say, hey, you three, you guys are getting the half the round for me. 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 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, we're tripling revenue, you know, every six months or something during the program, just go ahead and 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.

1:33:10And 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 what why combinator announced they're doing now that they're doing now. 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 nontraditional. Like we had one of our successful companies do a deal for common shares at a ridiculous price with some nontraditional private equity firm. And we passed.

1:33:40We 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, you know, hitting...

1:33:55eight figures in revenue. They were public about that at the launch festival. They gave a keynote. We offer, and I offer them live on stage, two million out of 50 million posts. But anyway, we wanted to put more money in a couple of times. You know, we built our position up to, you know, over 10%. So that's what I'm trying to do now is just get to 10, 15, 20%. And eventually, you know, with our fund, the syndicate, you know, and the accelerator, we can make three or four bets in the company.

1:34:23and 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, Angelist, Slash Seed Investors, Republic, whatever crowdfunding, you know, Syndicate you like, with a seed fund, like Homebrew, or...

1:34:43pair or 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 fun plus syndicate kind of hits the one two million dollar number. But you know, the next fund perhaps will be able to do a full A like a five 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 do go and do the big checks. And there's so many specialized people at that. I'd rather hand it off to Sachs, work some off or Bill Gurley or you know, rule off for somebody like that. All right, listeners. Now is a great time to talk about one of our favorite companies, Statsig. 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. Yep. In the

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1:36:17Well Jason. This has been 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 main show here. And for the LP show, I think we're going to do is we're going to dive into your investing, the way that you're sort of, frankly, deconstructing the jobs of a VC firm, sourcing, evaluating, 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 view the flywheel or the fun ol' or how you sort of visualize it. And then I know you've got some good insider stories. Good insider stories for sure, the couple you brought up. And also like frankly, the way you see the world. Yeah, I'm sure there's a hot take in there. I got a hot take post corona. Yeah, yeah, yeah. All right. Listeners, thanks so much for going on the journey with us here. I'll spend the 100 bucks. You coming LP member like me. All right. Listeners, thanks. LP's we'll see you on the other side.