Special Episode: Jason Calacanis

[0] Let me just make a little ad here.

[1] Yeah, please.

[2] Hi, this is Jason Calacanis for Acquired .com.

[3] Is that the domain?

[4] Acquired .com.

[5] That is it.

[6] Yeah.

[7] All right, listen.

[8] You're listening to this.

[9] You're either a founder, an aspiring founder, an investor, or an aspiring investor.

[10] For $100 a year, you're going to get hours of content that's not available to everybody else.

[11] That's also known as an edge.

[12] You are in a competition with other investors.

[13] You're in a competition with other founders.

[14] You need an edge.

[15] If I could tell you, you get one, two, three good insights a year, even one, would you pay $100 for an amazing insight that gave you an edge against your competitors?

[16] Of course, you would.

[17] You pay $10 ,000.

[18] So why wouldn't you pay $100?

[19] Because it's content?

[20] You're thinking about it the wrong way.

[21] The LP program at Acquired .fm is not, it's not content.

[22] It's an edge, and it's an underpriced edge.

[23] So buy it for $100 now before they raise the price to what it should be, which is $5 ,000 a year.

[24] This is Jason Kyle Cash for Acrequired .fm.

[25] See you in the Slack.

[26] How's that for an ad, huh?

[27] You can have that.

[28] Mike, can you actually take your mic?

[29] You can literally have my end.

[30] You can have my end.

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

[32] No, I just love doing ads.

[33] Thank you.

[34] Welcome to this special episode of Acquired, the podcast about great technology companies and the stories behind them.

[35] I'm Ben Gilbert.

[36] I'm David Rosenthal.

[37] And we are your hosts.

[38] Acquired is all.

[39] about stories.

[40] Ordinarily, we tell the story of a great technology company or a great leader or a great adaptation.

[41] Today, we are telling the story of someone who doesn't just have one story.

[42] He has a whole anthology across all of those categories, the one and only Jason Calicanus.

[43] So just to give our audience a small sampling of all of the enterprises that Jason has started and is involved with across his career.

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

[45] No. Jason has founded four companies by our account, Silicon Alley reporter, weblogs, Mahalo, and Inside .com.

[46] Do we miss any?

[47] No, those are them.

[48] Those are the four.

[49] And Inside .com is the same cap tab.

[50] It was just the pivot of Mahalo.

[51] So arguably one.

[52] Did not know that.

[53] People don't know that.

[54] We'll get into that.

[55] Three conferences, three podcasts.

[56] Angel, all in.

[57] And of course, this week in startups, which is now over a thousand episodes.

[58] The YouTube channel around all of those.

[59] you were the first Sequoia Scout.

[60] You were literally the prototype of the Sequoia Scout.

[61] Correct.

[62] And still the greatest returner.

[63] And still the greatest returner.

[64] But who's counting?

[65] It's not a competition, but I won.

[66] Maybe some time might have something.

[67] Well, we'll get into that.

[68] You've made over 200 angel investments in your career.

[69] You are a blogger.

[70] You're an author.

[71] You have a newsletter.

[72] You started the launch accelerator, the venture fund around that, the syndicate around that.

[73] You are the self -pervest.

[74] We have you on record as saying, are the either third or fourth best angel investor of all time.

[75] For sure, yeah.

[76] For sure, I'm out Rushmore.

[77] Chris Saka, Ron Conway, obviously ahead of me. And then there's a bunch of people.

[78] Nobody knows who did incredible angel investments, you know, in Google and Apple.

[79] But they don't have like, they don't feel the necessity to put it on the cover of a book like I did.

[80] Speaking of, quote that we want to wrap this up with from your book, most folks think I'm lucky.

[81] 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.

[82] I agree with all of them.

[83] Jason Calcanus, welcome to the show.

[84] A big fan of the show.

[85] Thanks for having me on.

[86] And David, thank you for doing that intro because your voice is so much better than Ben's.

[87] I mean, that is a radio voice you have, David.

[88] It's so soothing.

[89] And Ben and I are just like scratchy records.

[90] But Ben's got good insight.

[91] So I'm glad to be here.

[92] I'm a big fan of your podcast.

[93] Got to have something to rely on, Jason.

[94] Exactly the insights.

[95] thanks for joining him so okay today probably most people listen to subscribe to jason on one of these many channels we've talked about today we're going to talk about two sort of less discussed parts of jason's story one on the main show here is how jason has built his whole empire across all these properties and how it all ties together uh 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 so Empire, what Jason's secret master plan is, a la his friend Elon, and why it might represent a wholesale deconstruction of the entire startup ecosystem.

[96] So you can click the link in the show notes or go to glow .fm.

[97] slash acquired.

[98] I'm a member.

[99] I pay 100 bucks a year or something.

[100] Well, thank you.

[101] We appreciate it.

[102] It's worth it.

[103] The LP show is like the best parts.

[104] It's like you cut the nice like the rib eye and that's like the best part.

[105] It's like the New York strip of the podcast.

[106] It's great.

[107] Well, we hope that the whole podcast is good, but we appreciate the LB stuff is the tightest, I have to say.

[108] You guys put the most work into that, and people will just pay for it.

[109] You want good content to exist, pay for it.

[110] If only all of our guests were like you, Jason.

[111] Okay, listeners, now is a great time to thank one of our big partners here at Acquired, ServiceNow.

[112] Yes, Service Now is the AI platform for business transformation, helping automate processes, improve service delivery, and increase efficiency.

[113] 85 % of the Fortune 500 runs on them, and they have quickly joined, the Microsoft's at the NVIDIA's as one of the most important enterprise technology vendors in the world.

[114] And just like them, ServiceNow has AI baked in everywhere in their platform.

[115] They're also a major partner of both Microsoft and NVIDIA.

[116] I was at NVIDIA's GTC earlier this year and Jensen brought up ServiceNow and their partnership many times throughout the keynote.

[117] So why is Service Now so important to both Nvidia and Microsoft companies we've explored deeply in the last year on the show?

[118] Well, AI in the real world is only as good as the bedrock platform it's built into.

[119] So whether you're looking for AI to supercharge developers and IT, empower and streamline customer service, or enable HR to deliver better employee experiences, service now is the platform that can make it possible.

[120] Interestingly, employees can not only get answers to their questions, but they're offered actions that they can take immediately.

[121] For example, smarter self -service for changing 401K contributions.

[122] directly through AI -powered chat, or developers building apps faster with AI -powered code generation, or service agents that can use AI to notify you of a product that needs replacement before people even chat with you.

[123] With ServiceNow's platform, your business can put AI to work today.

[124] It's pretty incredible that ServiceNow built AI directly into their platform, so all the integration work to prepare for it that otherwise would have taken you years is already done.

[125] So, if you want to learn more about the ServiceNow platform and how it can turbocharge the time to deploy AI for your business, go over to servicenow .com slash acquired.

[126] And when you get in touch, just tell them Ben and David sent you.

[127] Thanks, ServiceNow.

[128] So, Jason, you've talked a lot about growing up your childhood.

[129] So we'll do that briefly here.

[130] You're born in New York, right?

[131] Brooklyn.

[132] Brooklyn.

[133] Yeah.

[134] You know, when you come from New York, you don't say New York.

[135] You say, not only do you say the borough, you say the borough.

[136] part of the bar.

[137] So I'm from Bay Ridge, which is literally the last stop on the train, on the train.

[138] Love it.

[139] Tell us a little bit about your family and what growing up was like for you.

[140] Yeah, I grew up in the 70s and 80s, which was a fantastically interesting time to grow up as a young person.

[141] We were free -range kids to the extreme.

[142] And Brooklyn and, you know, was not hipsters back then.

[143] It was, you know, working class and connected guys and the hell.

[144] angels and cops and bookies, and it was a little bit more rough and tumble.

[145] My dad owned a bar.

[146] He was essentially the mayor of Bay Ridge in a way, like people loved my dad, John the Beard, and they loved his bar.

[147] And I worked at his bar, my two brothers and I, my older brother, my younger brother, Jamie and Josh, from a very young age.

[148] My mom was a nurse, and she ran the emergency room in Brooklyn at Victory Memorial Hospital, and then later ran the ICU.

[149] She's a nurse practitioner.

[150] And she's got, I think, three graduate degrees.

[151] So I had this amazing hardworking mother doing three or four jobs, had this amazingly hardworking dad.

[152] And it was a blue collar lifestyle.

[153] We owned our house, but barely.

[154] We were always living month to month.

[155] But there was a lot of love and a lot of craziness.

[156] Growing up in a bar, I literally grew up in a bar and made espresso for mob bosses, made bake clams for Tony Bennett, would go get some.

[157] cigarettes for the Coke dealer would put bally's 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.

[158] It sounds like not just a bar.

[159] This is more like a pub.

[160] It was a pub, exactly.

[161] It was kind of like a pub.

[162] And the cops would come in anytime they wanted, but usually they come in between lunch and dinner.

[163] And my instructions were just give them whatever they want and just charge them bucks each.

[164] And they would proceed to drink four or five Irish coffees each.

[165] Did they order them as Irish coffees or?

[166] Yeah, no, there was the wink and then it was the wink.

[167] You know, they, they were in uniform, so they just wanted to have a cup of coffee.

[168] Hey, kid, give me a cup of coffee.

[169] And whenever I got the bookie, Artie Moreska, uh, or the, uh, the guy who dealt, uh, cocaine, uh, his pack of cigarettes or whatever, they would just say, here's 20 or here's a 50 sometimes, or sometimes even a hundred, go give me a pack, give me two packs of Marlore Lights.

[170] I go out, get two packs of Marlite.

[171] It was $2 or $1 .50 a pack, and they say, keep the change.

[172] This is like the Brooklyn version of Bob Iger's story with the chairman, Frank Sinatra, going out and getting their mouthwash.

[173] Exactly, exactly.

[174] 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.

[175] My first real job was a guy owed my dad like two grand he had lost playing backgammon to him.

[176] My dad used to have a backgammon in a poker game.

[177] When the bar closed at four, the fun began from four to seven or eight in the morning, they had after hours, which was mainly cops and Hells Angels and mafia guys and, you know, hippies.

[178] All playing together.

[179] Yeah, yeah, yeah.

[180] And I would come and I would do the porter work at 7 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, rest in peace.

[181] And we were the porters, a fancy way saying janitors and my dad would be there playing cards or whatever.

[182] Anyway, this guy got, he was in for two grand, too large to my dad, and he couldn't pay.

[183] And he needed a little time.

[184] So my dad was like, that's fine.

[185] He said, here, I know the kid likes the Star Wars.

[186] Here's the Empire Strikes Back.

[187] And Empire Strikes Back was in the theaters.

[188] And he handed my dad a VHS tape.

[189] And my dad had got a VHS player that had fallen off a truck.

[190] This is before Blockbuster, obviously.

[191] It was like 1984 or something, I don't know, 85, no, 83, 84, something like that.

[192] They were just starting to have video rental stores, but something like Star Wars would never be allowed there, maybe come five years later.

[193] Anyway, long story short, I was like, this is incredible.

[194] I have Empire Strikes Back, and I had my friend bring his VHS over and I made copies of it.

[195] And my first job was Jason's hot tapes.

[196] I would make copies of the Empire Strikes Back and sell them for $20.

[197] I thought you were going to say you started running screening.

[198] No, that would be a better idea, actually.

[199] But anyway, it was before Jason learned about marginal costs.

[200] Exactly.

[201] I was like, wait a second.

[202] How much has a VHS tape cost?

[203] My math teacher says, hey, Calcanus, stay after.

[204] I'm like, oh, God, I'm going to get pinched.

[205] And so he says, I know you're selling this tape.

[206] I said, yeah.

[207] Because you think that's an okay thing to do?

[208] And it's like, no, I probably shouldn't be doing it.

[209] He's like, do you have these tapes with you?

[210] And I said, yeah.

[211] He goes, how much are they?

[212] they.

[213] I said, they're 20 bucks.

[214] He said, okay, I'll take one.

[215] And I said, here, it's on the house.

[216] I gave him the tape.

[217] So it's literally, I mean, when I save my life, when I was watching Goodfellas, I was using this Chrome extension called Seiner that we invested in to watch Goodfellas with some fans of the show.

[218] And I just tweeted.

[219] It's like group viewing, you know, like there's Netflix party and there's a sceneer.

[220] So now that everybody's home, you can watch Netflix with your family, whatever, so I put on Goodfellas.

[221] And I was just, I just, like, group viewing.

[222] You know, like, there's watching this kid growing up and I was just having flashbacks.

[223] I mean, literally my life was like the first act of Goodfellas.

[224] Well, Jason, I'm going to deviate from our little outline here a little bit, but like I know you're a prolific poker player.

[225] Like, I don't know if semi -proes the right word, but you play with pros, your friends with pros.

[226] Yeah.

[227] A lot of your investing patterns sort of match poker patterns.

[228] Informed by, yep.

[229] Yeah.

[230] So did that start here?

[231] When was your early poker game?

[232] I didn't.

[233] I was exposed to gambling at a very young age.

[234] I didn't participate in it.

[235] My My exposure to poker came when I was in New York, a friend of mine, Nadea Ressie, who started the Founders Institute, just started a $20 -30 poker game.

[236] And myself, Scott Hiferman from Meetup .com, Nick Denton had come to a couple of games.

[237] Jeff Dodge is from Razorfish and now One Drop, which I'm an investor in.

[238] Just a bunch of like the Silicon Alley folks would play cards and I'd play cards with them.

[239] And it was like one of those card games where people said, what's better, a straight or a flush?

[240] And somebody had to look it up kind of thing.

[241] Yeah, you have the little card next to you on the table where you're sort of referencing it.

[242] Yeah, literally, that was like that.

[243] It was just an excuse.

[244] And we used to play down in a place called Forlini's, which is still down in Chinatown, which is like an Italian restaurant.

[245] I'll leave it at that.

[246] And we used to play in the back.

[247] But then I went when I moved to L .A. And I spent a decade in L .A., a lot of my friends, like Sky Dayton, was playing cards.

[248] And my friend Kevin Pollock, who I was friends with the actor, he was playing cards.

[249] And we just, you know, those games were $200 buy -in or $500 buy -in.

[250] You had to be a little more serious about it.

[251] And then I, you know, the stakes started going up.

[252] I tried to study the game.

[253] I was terrible at it.

[254] And then I started getting invited to this game.

[255] This woman Molly kept inviting me and she'd be like, oh, Toby really wants you to come to the Four Seasons.

[256] And Leo really wants to see you.

[257] And I was like, Toby and Leo want to see me lose 20 grand.

[258] Like, they don't want to see Jay's a Gal Gadda.

[259] So I never went to Molly's game, but she invited me frequently because I was a fish for a whale, as we say, in the business.

[260] But yeah, that's when I got exposed to it.

[261] And then one of the early D conferences, myself, Bill Gurley, Mark Pinkus, and Sky Dayton, we're all there.

[262] And we said, hey, you guys want to play cards.

[263] And we went up to, I think it was Mark Pinkett's room.

[264] We just took the folding table.

[265] We started playing cards.

[266] And then we started hosting this game at the D conference, which later became recode.

[267] It became very famous, this poker game.

[268] And then we have a weekly poker game that everybody knows about here in Silicon Valley.

[269] You know, that's just my best friends and Phil Helm.

[270] youth and Draymond from the Warriors, Chimov, obviously, and David Sacks, just a really good group of guys who get together.

[271] And we've been playing virtually now, which is kind of fun.

[272] And now you have a podcast around it.

[273] Well, Chimoth was just like, Chimoth was one of these guests on my podcast who, you just burned the building down.

[274] And nobody really knew who Chabh was until he came on my podcast.

[275] And, you know, we started having him at the events.

[276] And then CNBC got their hooks into him.

[277] And now he's just like throwing bombs for a, living.

[278] Well, I'm sure he gets like just incredible page views whenever he goes on CNBC and tries much traffic.

[279] 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.

[280] I'm like, I know you made your money and you're retired and running a family office now, Chimoth, but I'm raising funds right now.

[281] It doesn't really help me to have you on the podcast saying that this is a giant Ponzi scheme.

[282] And he's like literally pouring gasoline over himself, lighting himself on fire.

[283] and I got, like, step six feet back to burn the building down.

[284] This is great, because this is the perfect saying to the media business.

[285] Yeah.

[286] So when, so you go to Fordham.

[287] After, was it right after Fordham?

[288] At night.

[289] You start as a, at night, you start as a reporter.

[290] How, well, so what draws you into the media business?

[291] Because to my mind, this is the, this is the, well, obviously you're growing up years and everything, you know, with that shaped you then.

[292] But starting in the media business is the wedge that brings us all to the Calacanus Empire now.

[293] Yeah, so this is a very interesting thing.

[294] What happened was, you know, I would go into Manhattan.

[295] I was just in awe of the people in Manhattan and people who were rich or famous and who were powerful because I had no power growing up and I was in a very dangerous situation and I was watching people who were powerful and I was like, okay, the book is very powerful.

[296] The head of the hell's angels is very powerful.

[297] This cop is very powerful.

[298] I am not powerful.

[299] My dad is powerful.

[300] My dad is powerful.

[301] He's got all these people in his bar.

[302] And I was watching money go around, and I was just fascinated by these topics, probably too much.

[303] And I saw magazines, and magazines are how information was really transferred in the, you know, 80s and 90s.

[304] And so I just started subscribing to every possible magazine.

[305] In the 80s, I got all the PC magazines and bites and all that kind of stuff.

[306] And then I started, you know, this Esquire, this paper magazine, Timeout, New York.

[307] So you were kind of like geeky people back then.

[308] It wasn't just that you were like, you know, reading Esquire or like the source or whatever.

[309] Like you were, you were reading the tech plugs.

[310] I was reading all the tech stuff and I was really into technology.

[311] I had a PC junior computer that my dad had bought me with cash from the restaurant or Parker game.

[312] I was doing a little phone freaking, which is like getting phone codes.

[313] Anyway, I was involved in a bunch of scams.

[314] Yeah.

[315] Well, the phone freaking thing was kind of scary because the way Sprint worked in the early days is you just dialed an 800 number and then it asked you put it in like a five.

[316] or six -digit number, and then you either got a dial tone or it went, uh -uh -uh -uh -uh.

[317] It doesn't think 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.

[318] In the morning, you'd have two or three codes.

[319] So they started using somebody's code until it got turned off.

[320] And so we were doing all kinds of scams and stealing floppy disk and selling chessmaster.

[321] Anyway, I got out of all that, and I just went into IT.

[322] And so I worked in the computer lab at Fordham.

[323] I was making $2 .50 an hour, which was the minimum wage in 1987, I think.

[324] then I went to 350, then I got fired from that job because I had partitioned a hard drive and created a hidden hard drive where I put a bunch of video games and I was selling video games and WordPerfect.

[325] So you're entrepreneurial.

[326] Well, yeah, I was a criminal.

[327] I was selling WordPerfect out of the Fordham computer lab and I got busted.

[328] And then I started selling SPSSX or whatever that's called, like the 10 disk like $400 statistics package.

[329] And this is like.

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

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

[332] It's a little bit worse than the Star Wars.

[333] So I stopped all that and I realized I could just make six or seven bucks an hour.

[334] Then I went to work for Amnesty International.

[335] I started making $10, 12 bucks an hour doing IT.

[336] And IT just opened my eyes to like, whoa.

[337] And I saw the Internet early.

[338] I saw modems early.

[339] And it really opened my eyes.

[340] And then I thought maybe I'll write a book or whatever.

[341] And then I was watching this zine movement happened, Z -I -N -E.

[342] And so zines meant you published on photocopy page.

[343] 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.

[344] In 2 ,600, they would just self -print it, self -publish it, and it was just hacking stuff, right?

[345] Is that named after, like, 2 ,600 bod?

[346] Yeah, it hurts.

[347] Yeah, I think it was Hertz, which is, I think the, when Captain Crunch made the whistle, that would then give you dial tone.

[348] I think it was the 2600 Hertz.

[349] We can look it up online while we're here.

[350] But anyway, they used to always meet Manhattan in the city, the city bank building, in the lobby where the phones were.

[351] And there was a sort of culture in New York of hacking and media at the same time.

[352] 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.

[353] So I started Cyber Surfer magazine, which nobody knows about.

[354] And I got in a fight with the publisher after five issues.

[355] He sued me because I had trademarked the name.

[356] He didn't know I trademarked the name.

[357] I had no contract with him.

[358] was 23 years old, whole thing blew up.

[359] And then I was like, the Silicon Allie thing is going to become something.

[360] So I started Silicon Aller Reporter as a 16 -page photocopy.

[361] And Fred Wilson bought the first ad in it, along with Jeff Dachis from Razorfish.

[362] No way.

[363] He bought an ad for Flatiron?

[364] For Flatiron partners, $250.

[365] And he bought four ads at once, so he gave me $1 ,000.

[366] Wow.

[367] Advertising, like, their services as a venture capital.

[368] He just put the logo of Flatiron Partners.

[369] And this is 1995.

[370] I got two people to give me $1 ,000.

[371] I printed it up, it cost $2 ,000, and I just started handing it out of parties.

[372] 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.

[373] Because once I got like a thousand copies of this, I didn't have the money to ship it anywhere.

[374] So I would go to Razorfish's office.

[375] I would go to site specific.

[376] I would go to Eye Village.

[377] 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.

[378] So you're going to these early internet companies.

[379] Dropping it off.

[380] And they would say, oh, you're dropping it off.

[381] And I'd say, yeah, I'm the delivery boy.

[382] And they'd say, oh, that's very cool.

[383] I said, I'm also the editor.

[384] And there was a joke in the magazine.

[385] I put a CEO editor and delivery boy on the top.

[386] And what it was was it was quite charming to people that I believed in it so much that I would carry it with me. And then people also thought I was like, this is why when people say, like, they think I'm a hoaxter or a hype man or a fraud.

[387] People thought that back then because I would go to.

[388] parties with a stack of them in my hands.

[389] And I'd be handing them out to anybody who would take them because I just wanted to be famous.

[390] I just wanted to be powerful.

[391] I just wanted people to know my name.

[392] It's so interesting because it's so akin to the early days of blogging.

[393] I mean, it's just analog blogging where the, I'm sure any real publisher was looking at this like, oh, it's some kind of joke.

[394] I can't believe you're calling yourself a z. Like, it's not a magazine.

[395] You know, this is like literally what people said to me. And I said to them, no, I have a full page photo on the cover.

[396] That's what makes it a magazine.

[397] And they said, no, it's a newsletter.

[398] I said, no, newsletters have text on the cover of the magazine.

[399] This has a full -page photo.

[400] And then a guy named Carole Martesco emailed me because he saw the email in there.

[401] And he said, hey, I do this magazine I'll call Rez and I do this filmmaker magazine.

[402] He was doing filmmaker magazine, et cetera, and he knew how to do magazines.

[403] And he was like 10 years older than me. And he said, I can print this on real magazine paper for you.

[404] And I said, how much it costs?

[405] He said, it's going to cost $30 ,000.

[406] And I said, well, I have like $20 ,000 in ads now.

[407] This is by the fifth issue.

[408] And he said, don't worry about it.

[409] I can put it on my credit.

[410] I know the person.

[411] He printed it for me, just for free, just to do it for me. And then he's like, do you have the money?

[412] You have to pay the printer.

[413] And I was like, yeah, I've got to collect the money from the advertisers.

[414] And so then I went around and just asked people to give me the money, and I would bring them two or three grand.

[415] Thank you, Carol, Mortasco.

[416] Shout out.

[417] I was still friends to this day.

[418] And he basically mentored me on how to do that.

[419] And then at a certain point, my assistant, Linda Miller said, John Winter called And I said Okay, he's like, yeah, you know, from Rolling Stone And I was like, yeah, it's like year two of the magazine And I was like, okay, great And then I went to lunch and then she came back Did you call Yon Winter back?

[420] And I was like, no, I'll call him tomorrow I come back the next day and she goes, Did you call Yon Winter back?

[421] And I said, I don't want to do any press right now And she goes, no, no, he's not a journalist John Winter created Rolling Stone And I said, oh, he goes, He wants to meet with you.

[422] And so I went up, I met with Yon Wenner, and he had all my magazines on his table.

[423] And he said, hey, I want you to come work for me and do a magazine with me. I want to do, like, a digital version of Rolling Stone.

[424] And I said, no, I want to do my own thing.

[425] And it was up in his office, and he had marked all the pages.

[426] But Jets said, wouldn't that have made you famous?

[427] Like, why wouldn't you do that?

[428] I also realized, no, it realized that would be a number two.

[429] And I never wanted to be number two.

[430] So it's about the fame and the power, or it was in this era.

[431] All that.

[432] Fame power and money.

[433] That's all I wanted.

[434] I just wanted to have fame power and money, all of those things.

[435] And I just like, number two, no. And then all of a sudden, I became the king of New York because the internet hit.

[436] Magazine went to 75 full -time people, $12 million in revenue.

[437] I built it up my credit cards.

[438] I was on Charlie Rose.

[439] I was on the cover of the New York Times.

[440] And in three, four years, I went from being a nobody to writing for paper magazine.

[441] And when I would walk into any club or whatever, people knew what Silicon and I reporter was, and I could get into any party.

[442] And then I made a list of ranked the top 100 people in the industry.

[443] And I ranked it just to tweak people.

[444] And then people would beg me to move up 10 rankings.

[445] And I got everything I wanted.

[446] Power, the minus list is still doing that to this day.

[447] Yeah.

[448] And I did my first event in 1995 called Ready Set Pitch.

[449] And you can look it up in the New York Times.

[450] There's an article about it, Ready Set Pitch.

[451] And it was just I asked people to pitch their best idea for a startup.

[452] And Ted Leontes gave the keynote.

[453] So it's pretty funny.

[454] As you're getting all this power, what's going through your mind?

[455] Like, are you already starting to think about?

[456] More.

[457] Are you thinking about I parlay this in.

[458] to investing or I prior to X or like what's I wanted to be the next media mogul.

[459] I wanted to be Eisner.

[460] I wanted to be like Iger.

[461] I wanted to be Ovitz.

[462] I wanted to be somebody like that because media was the power back then.

[463] It wasn't really about the tech companies.

[464] The tech companies were kind of like this cute little thing on the side.

[465] This is Warner days.

[466] Yeah.

[467] You know, like that's what I wanted to be.

[468] I wanted to be one of those media executives and be the CEO of a giant media company, Barry Diller, someone like that.

[469] So you end up selling Silicon Alley Reporter to Dow Jones, right?

[470] Yeah, it kind of collapsed and we wound up selling, I got two years of salary.

[471] But the year before, Alan Mackler from internet .com, it offered me $20 million for it.

[472] And I owned like 85%, 90 % of the company.

[473] 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.

[474] Was it the dot com crash?

[475] Yeah, the dot com crash.

[476] And then 9 -11, and I was there for 9 -11.

[477] brother's a firefighter.

[478] We didn't know where he was.

[479] 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.

[480] Everybody thinks I'm a fraud.

[481] Everybody thinks I got lucky.

[482] You had all this power.

[483] And it was gone.

[484] It was gone.

[485] Did it disappear?

[486] Did it really disappear?

[487] 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.

[488] And then when you have the might as tough, and then you start touching stuff, and nothing changes, it really is humbly.

[489] It's literally like you go from feeling like you're Superman, and then you can't fly.

[490] And you're like, what's going on?

[491] Is it a kryptonite in my shoes or something?

[492] And it was a very humbling experience for me, and it made me really angry.

[493] I remember vividly.

[494] I just felt very angry at the world and at myself, or not taking that $20 million.

[495] So it wasn't just angry about what was happening.

[496] It was like you were specifically like angry about passing on that deal.

[497] I was angry at passing on that.

[498] I was angry that the market collapsed.

[499] I was angry about 9 -11.

[500] It was just angry about everything.

[501] But I also had skills at that points and confidence.

[502] 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.

[503] And I will show everybody that not only am I not a fraud, that I can do this again and I can do it quicker, faster, and better.

[504] And I started looking for an idea.

[505] And I was studying and studying and studying.

[506] And two people who worked for me after the whole thing collapsed had moved on and started blogs.

[507] and they were doing really well with their blogs and one of them was Rafad Ali who was doing this paid content .org and I had admonished him because he started it when he was working for me I was like, listen, kid.

[508] I didn't realize Rafat worked for you.

[509] Yeah, it was one of my writers.

[510] I think I was his second job.

[511] He had worked for inside .com and then for me. And he had own the inside .com domain at one point.

[512] So there's a whole sort of history there of who got to own inside .com at the end of the day.

[513] I can tell that story too at the end.

[514] But anyway, I was like, and then Cheney Jardin went to work at Boing Boing.

[515] And I found out they were both making like four or five grand.

[516] And I was like, wait a second.

[517] 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.

[518] Just on ads on their blogs.

[519] Exactly.

[520] So I was like, wait a second.

[521] These people are working in their underwear.

[522] They have no editor.

[523] And it dawned on me. The right writer and editor is a hindrance.

[524] they're taking out what's special about what the person said this is like taking out the production it's like Bob Dylan just on stage with the guitar it's better when it's not produced it's better when it's acoustic and there was that thing that it was going on MTV had unplugged and I said this is MTV Unplugged for journalism blogs it just clicked in my mind clear as day when you saw Kurt Cobain on MTV Unplugged you wanted to throw the other records away that was studio produced.

[525] And I said, blogging is going to be a thing.

[526] So I started looking for other blogs.

[527] And I knew this kid, Nick Tenton, who started First Tuesday, and he started Gawker.

[528] He said, hey, Nick, you know, want to have lunch?

[529] We went for lunch.

[530] I said, I'm thinking about doing a blogging thing.

[531] I think this could be big.

[532] If somebody did it for business, it would be huge.

[533] You're doing this Gawker gossip thing.

[534] I'm not interested in that.

[535] But if somebody did a business version, and then he wrote a blog post and he said, the worst thing that could ever happen to blogging is Jason Calacanis bringing his, unique brand of like whatever to it.

[536] Corporate sellouts.

[537] Well, that's what he said.

[538] Because I was like, you know, this would be an advertising juggernaut.

[539] Because think about it, you get rid of all of the, you get rid of like 80 % of the staff.

[540] You just have the one great writer and one great salesperson.

[541] Did ValleyWag exist at this time yet?

[542] No, no, no, no. Valley Wag he created much later.

[543] It was just Gawker.

[544] I mean, really, like I've worked at the Wall Street Journal.

[545] I mean, you did two for a while.

[546] Like, you know, it's a wonderful organization.

[547] There are a thousand people in that building.

[548] Yeah.

[549] Like, it's crazy.

[550] That to do this.

[551] No, you don't need a building.

[552] Yeah.

[553] You don't need middle management.

[554] I mean, you don't need anything.

[555] So I was really taken by, you know, Denton's vision for this.

[556] And I was like, are you going to do more?

[557] And he's like, yeah, we're doing this.

[558] We're going to do a political one, I think.

[559] And we're going to do this one on gadgets.

[560] Like, you know, like the fetish thing in Wired Magazine.

[561] We're going to just make that into a whole thing.

[562] And I was like, oh, that's interesting.

[563] So he writes his blog post, trashing me. And I was like, you monom.

[564] And so, you know, like, I'm a pretty aggressive guy.

[565] And I was like, so I, like, My partner Brian Alvey, who I convinced to do this with me, is 2003.

[566] None of us had any money.

[567] We're doing it all for free.

[568] The economy was flatlined.

[569] I said, I'm going to destroy him.

[570] Which it turns out you were not the last person to have that thought.

[571] No, no, no. I was not the first.

[572] I might have been the first, but not the last.

[573] I said, I have to destroy Nick Denton.

[574] How am I going to do this?

[575] And I said, oh, I know, talent.

[576] There's nothing worse than losing talent.

[577] Elizabeth Spears, she's writing Gawker.

[578] I'm going to make a run at her.

[579] And I had heard that he was paying the riders $1 ,500.

[580] And the MacBook Air had just come out.

[581] I contacted Elizabeth, and I said, let's have coffee, whatever.

[582] And she agreed to have coffee or something.

[583] And there's like a photo of it, actually, of me talking to her at a bar that somebody took in the early days.

[584] And she's looking at me like, I am the Antichrist.

[585] And I was like, you are a unique talent.

[586] Nick Denton will never give you equity.

[587] I will give you equity.

[588] You will become a millionaire.

[589] I'll give you a MacBook Air and I'll give you $2 ,000 a month, which is a 33 % more raise.

[590] She was like, yeah, no, I'm going to go work for New York Magazine.

[591] And I was like, that's the worst career movie you could ever make, Elizabeth.

[592] Magazines are going to die.

[593] Blogs are going to take over.

[594] There's no way magazines can ever keep up with blogs.

[595] Whatever they print is going to be old news, and you're already proving it.

[596] You're number one at blogging, and you're going to become number 500 at a magazine.

[597] So she wouldn't do it.

[598] And then, Shennie Jardin said to me, oh, you picked the wrong target.

[599] talking to her because I was trying to recruit her.

[600] She's like, no, no, I love this point -point thing.

[601] I don't want to do anything commercial.

[602] And I was like, all right, that's fair enough.

[603] I said, who should I target?

[604] She goes, oh, you pick the wrong target.

[605] I said, what do you mean?

[606] Oh, Nick's not making any money in Gawker.

[607] Gawker doesn't make any money.

[608] Luce his money.

[609] I was like, okay, tell me more.

[610] She goes, 100 % of the revenues coming from Gizmoda.

[611] I said, oh, okay.

[612] He goes, do you know Peter Rojas?

[613] I was like, yeah, I've heard of him.

[614] That's the one you want.

[615] So I went to Peter Rojas, and I called this guy I knew who was running Jewelbach.

[616] Koo, which was like a fancy sushi place in Luryside, and he was the owner and his wife, and it was like a pretty hot ticket.

[617] And I asked Peter to come have sushi with me. And his wife, Joe, or his girlfriend at the time, she said, can I bring my girlfriend?

[618] So, of course.

[619] We go there, and I'm prepared to, like, knock their socks off with his own macase.

[620] And I said, you guys have anything, you know, terms of, like, die and, like, we're vegans.

[621] I said, okay, yeah, that's no problem.

[622] I said, give me one second.

[623] I go up.

[624] back to the guy said, listen, I'm trying to close this deal.

[625] It's really important.

[626] Like, they're vegans.

[627] He's like, don't worry about him.

[628] We're right back.

[629] He runs to the Korean grocery on the store.

[630] He comes back with two big shopping bags full of things.

[631] And he makes them the most amazing omacasi with vegetables.

[632] Wow.

[633] And so I said to Peter, I said, Peter, you know, Nick Denton is a bad actor.

[634] And equity is what you need.

[635] And if you join me and you create a Gizmodo killer, I'll give you equity in the company.

[636] And you will become a, a millionaire and we'll be in it together.

[637] You'll be a partner.

[638] And he goes, well, Nick said he's going to give me equity.

[639] He said, he'll never give you equity.

[640] When did he tell you that?

[641] He told me that like six months ago.

[642] I was like, yeah, how's that going?

[643] 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.

[644] And he came back and he said, okay, I'll do it.

[645] I said, great.

[646] This is so great.

[647] By the way, at this point in time, this is, I'm probably 17, 18, 19 years old at this point.

[648] I'm reading Gizmodo every single day and I always wanted to know what happened how did Engadgett become I never knew yeah this is the story and he says oh my girlfriend Jill made a logo and Jill made the first Engadget logo I was like great he said can we pay her for it I was like sure we can and I was like what does she charge for Logan he's like 300 I was like give her 500 it's fine because Mark Cuban had given me $300 ,000 for 15 % of Weblogs Inc how did you get to know Mark?

[649] I had no mark because I had written broadcast .com is a billion dollars worth of hot air in Silicon Island Reporter, and he blew a gasket.

[650] And I said, well, your revenue is like 10 million.

[651] He's like, do you know what the revenue is next quarter?

[652] I was like, no, you're a publicly traded company.

[653] Of course, I don't.

[654] He's like, well, why don't you wait?

[655] And then revenue went from 10 to like 60, you know, like quarter over quarter.

[656] And I was like, okay, it's not a billion dollars in hot air.

[657] And I did a mea coppa kind of situation.

[658] And we became good friends, Mark and I for a long time.

[659] And he put 300K in.

[660] We started a blog Maverick for him.

[661] Brian Alvey came up with the name.

[662] Brian Ava came up with all the good names, the best collaborator ever had in my life.

[663] And Peter.

[664] And so Peter said, listen, you know, I just, I feel really bad about this stuff with Nick Denton.

[665] I was like, you shouldn't feel bad.

[666] This guy promised you equity and he gave you nothing.

[667] And you've given him this incredible brand.

[668] That's going to become worth millions of dollars.

[669] You should feel zero guilty.

[670] He robbed you of your vision and we're going to take it back.

[671] And he's like, yeah, yeah, yeah, maybe you're right.

[672] And I was like, yeah.

[673] Because listen, I've been in fights.

[674] And, you know, if somebody takes a swing at you, like somebody gets a, if somebody's sucker, punches you, you have to teach them a lesson so they don't do it again.

[675] Because if you don't teach them a lesson, what I learned is they will come back.

[676] It has to be such a beatdown.

[677] It has to be so painful that the person says, I should have never punched that, I should never sucker punch that guy.

[678] That's how powerful the beat down has to be.

[679] It can't just be retribution of one for one.

[680] If they punch you, you have to annihilate them.

[681] this is what I learned about violence when I was growing up.

[682] And I've since disavowed this, but this is literally what I saw on the streets of Brooklyn in the 70s and 80s.

[683] So I said, when are you going to tell Nick?

[684] And he said, well, he's, you know, he's been working so hard for like a year or half or whatever.

[685] And he's just burnt out.

[686] He's been working seven days a week on this.

[687] And he said, he's going to take his first vacation.

[688] I said, oh, really?

[689] He's like, yeah, yeah.

[690] And he's going down to Brazil or whatever.

[691] And all these famous people are going.

[692] I was like, when is he going?

[693] He's like, he's going Sunday.

[694] I was like, oh, what time is he leaving?

[695] I don't know what time he's leaving I said okay I looked up online like flights to Brazil whatever I couldn't kind of figure it out I was like 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 his vacation he landed with his people going Gizmodo has no blogger we have all these advertisers and there's a competitor oh my god and that was the approach I used to take to competition I don't do that anymore but well by the way and the postscript to that is Denton and I became very good friends after that for a long time and still are.

[696] And I consider him one of the, just the great publishers.

[697] But you can't raise over that.

[698] So how does that happen?

[699] Oh, he reached out.

[700] He reached out afterwards.

[701] He wrote a blog post actually saying, you know, Jason really stuck it to me, but we're going to be great competitors.

[702] And then I launched joystick, and then he launched Kotaku.

[703] Then I launched Autoblog.

[704] Then he launched Jolopnik.

[705] And when we were head -to -head, we always had three, four, or five times the traffic as him.

[706] But it created this rivalry that everybody followed.

[707] It became Coke Pepsi, it became, you know, oh, yeah.

[708] Pick Media Company versus Media Company.

[709] And everybody was following this great competition between this Brash Brooklyn Kid and this aloof, you know, quietly.

[710] Well, it probably made you both better, right?

[711] Oh, I mean, it's incredibly much better.

[712] But, you know, it was like literally this like quietly gay, you know, very understated Brit versus this brash Brooklyn Bulldog.

[713] And it just played really well in the press.

[714] And you can, if you type Dent and Calacanacanacin to Google and look at some of the posts from back then.

[715] It's hilarious.

[716] And it was just a good time.

[717] But he reached out to me and he said, listen, I think we should have a, Jason, respect for what you did there.

[718] I understand, you know, Peter, best of luck with Peter.

[719] And, you know, we went for a coffee, whatever.

[720] And we're sitting there.

[721] And he said, I have a proposal for you.

[722] And I said, yes.

[723] I think that, you know, if we're going to have this spirited competition, that's great.

[724] You know, good for the game and all that.

[725] you're a worthy competitor, and obviously you've been able to...

[726] You're just waiting for the knife to come out.

[727] Well, yeah, and I'm just like, okay, this could escalate.

[728] Yeah.

[729] And he said, I'm proposing a no -poach agreement.

[730] And I said, what does it mean?

[731] He goes, well, we just, you know, there's no need.

[732] There's so many writers out there.

[733] We're not enemies.

[734] What we're fighting against is the magazines and the newspapers.

[735] You know, we're up against the New York Times and that's enough competition for us.

[736] And I said, you know, that makes a lot of sense.

[737] So we will We agreed to not poach each other's writers Well Jason I gotta 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 Atwa 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 web blog 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 Steve always realized the power of the media well yes I mean Steve was the master and I had spoken to Steve in person two or three times and over email you know half dozen times during the Engadget time Peter much more he really loved Peter and Steve was really great and anyway they had some sort of problem with it and they said you can't use Apple in the name And I said, okay, and I just said, you know, it's back when you could buy domain names.

[738] And I said, the unofficial Apple weblog.

[739] I said, this should make an acronym, twa.

[740] And then just build a logo.

[741] And I think Jill Ferenbacher, you know, Peter's now wife, mother of his kids, I think she built that one as well.

[742] Took the little leaf of the apple and just threw it above the twas and called it a day.

[743] Well, that was kind of, I think that was Brian Alvey's joke.

[744] It's like, it sounds like it's French.

[745] So let's put it as like an accent de grove on top of the day.

[746] And I was like, sure, let's troll them.

[747] And we do, it's just like a lot of crazy stories like that.

[748] And long story short, that company lasted 18 months.

[749] We sold it for $30 million to AOL.

[750] This is all of weblogs, Inc. This is all of the weblogs, Inc. We had $100 ,000 in revenue to date and probably $200 ,000 looking forward.

[751] So depending on how you count that, they paid three.

[752] They played a big multiple.

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

[754] Of course.

[755] Yeah.

[756] I mean, if you, that gave me the money to become dangerous and it gave me that foundation, you know, when you get that, you know, the first 10 million is the hardest.

[757] And once you get that under your belt, you're dangerous.

[758] Nobody can stop you.

[759] I mean, I was already dangerous because I didn't care.

[760] But once you get the cash, then you really have the ability to not care.

[761] Right.

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

[763] I mean, listen, here's the joke.

[764] Denton wound up selling, I think, for 150.

[765] 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 Thiel and then some amount got left over.

[766] I think we wound up netting about the same.

[767] It just took him 12 years and it took me 18 months.

[768] But you know, what I was...

[769] But for you, you got to start writing your next chapter.

[770] Exactly.

[771] You know the thing is I had, the great thing about Silicon Alley reporter crashing and burning was I learned very early on that I was more than the brand because the brand Silicon Air Reporter had gotten so big and I was so identified with it that I started, people would call me the Silicon Allie Reporter.

[772] That was like what people would refer to me as.

[773] And because it crashed and burned, I was forced to disconnect myself from that.

[774] And I, Bob Dylan was always my favorite artist.

[775] 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.

[776] And then he started collaborating with Mark Knopfler of Dioch Straits and did Empire Bolesk and, you know, all these other really infidels and these very interesting albums.

[777] And I seen Bob Dylan maybe 20 times, you know, in person.

[778] And he was, you know, always my favorite.

[779] And I was like, don't look back.

[780] And I just told myself, you cannot look back.

[781] And I never look at my press.

[782] The amount of press I got in the 90s, between being on Charlie Rose, being on 60 minutes, all that stuff.

[783] I knew that I was never going to top that.

[784] You know, like that was a moment in time.

[785] And I didn't want to top it.

[786] Who cares?

[787] Like, I put all that press in boxes.

[788] I taped it up, and it's literally in my brother's garage in New York still.

[789] I don't want to ever look at those clips.

[790] Don't look back.

[791] Only forward.

[792] Next brand, next brand, next brand, next brand.

[793] Don't worry about the last brand.

[794] And that's how I looked at myself at that point.

[795] I looked at myself and I said, you know what?

[796] Kurosawa did all those samurai films.

[797] and then he went into noir, and the noir stuff was better.

[798] And nobody even knows about the noir, you know, the film noir stuff he did.

[799] High and Low, Shre Dog, you know all this kind of stuff.

[800] Is it after then the next chapter, you get money, you're back in the game after weblogs.

[801] I'm in the game, baby.

[802] Is that when you moved to L .A.?

[803] I had been living in L .A. when we start, right after we started Weblogs Inc. Yeah.

[804] And at this point, do you still want to be, be famous?

[805] Once you've adopted this mentality of don't look back, are you still fame driven?

[806] No, fame wasn't.

[807] I really wanted to build things.

[808] I had gotten into the mode of building not necessarily empire building.

[809] Was that from hanging out with like Silicon Valley types?

[810] I think it was.

[811] I think also when you get the win under your belt, it takes the edge off.

[812] And I always tell that to young founders.

[813] Like, you know, winning really takes the edge off.

[814] And you will be successful.

[815] It may take two or three companies.

[816] You know, have 60, 70 % of these things fall.

[817] Don't worry just start 304, you're going to have a hit.

[818] And nobody remembers, like, we're sitting here.

[819] When people meet me, they don't know what Mahalo is.

[820] They don't know what Silicon Air Reporter is.

[821] They don't even know any of this stuff.

[822] Nobody has any sense of history.

[823] But people are all caught up in their own history.

[824] I for sure had a Mahalo account.

[825] Yeah.

[826] I mean, Mahalo did really well.

[827] I mean, that's a whole other story.

[828] But, yeah.

[829] That's another one, right?

[830] Well, you just, you build a brand that becomes so big, and you kind of get associated with it.

[831] And then you have a big flame out.

[832] And it's like, who cares?

[833] just move on next one we'll get there but i do want to talk about the mahalo pounce twitter that sort of tumbler like yeah let let's let me put a pin in that and david keep running with your your line here well okay so this is this is a diversion but we side track but we got to cover it when you're in l a how do you meet travis callanick well i when i was doing silicon i reporter we had started a um an edition called digital coast reporter and i had interviewed Travis when he was doing scour, which was his first company.

[834] Oh, wow, yeah.

[835] And he got sued and all that stuff, and he told the famous story.

[836] And that was the night, allegedly, when Michael Ovitz's people came and were in the audience at my event.

[837] I used to do a CEO interview, and I interviewed him.

[838] So that was that famous story.

[839] And then he did Red Suuition.

[840] We'd always been friends and we'd always liked each other.

[841] And that's how I wound up investing in Uber, because when he was raising money for it, he wasn't going to be the CEO.

[842] He was like, hey, I'm doing this company.

[843] It was like, you know, Ryan and him.

[844] And Ryan was CEO?

[845] 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.

[846] I said, what happened with Ryan?

[847] I was like, oh, this is a little shaky or whatever, and then I just made it as the first scout bet, and I introduced, I think first round and definitely Cyan, we're at the Open Angel Forum, the little event I used to start where I matched angels.

[848] So at this point, you're running Mahalo at this point?

[849] Yep.

[850] So I didn't actually really, was Uber the very first scout investment?

[851] I think it was the third.

[852] I think I had, in the first seven, there were three unicorns.

[853] And this is Sequoia Scout.

[854] As is Sequoia Scout, I had in the first seven, Uber, thumbtack, and data stacks.

[855] So three companies, three unicorns, one of them public, decalcorn.

[856] We'll see about the other two, but I think the two got a chance to go in public too.

[857] And so our listeners understand here, and we didn't list all the companies that you've Angel invested in, but we're going to keep touching on them as we go.

[858] So, like, so when you're investing as a scout, that's not your own money.

[859] So how did the economics work on that?

[860] No. It was 50 -50.

[861] So it's 50 -50 basically splitting the carry, the profits off that investment.

[862] Yeah, it's crazy.

[863] They since dropped it, I think, to 35 or 30, like a normally high carry.

[864] How did this happen, though?

[865] Like, what?

[866] Well, Rulov call me. Did you go to Ruloff or did RulaF come to you?

[867] I had lobbied Sequoia.

[868] I had emailed Sequoia and lobby them to invest in my friend's poker game.

[869] Zinga poker I'm sorry what is that The poker game My friend created a virtual poker game Mark Pink is called Zinga And our dog just to play it Never heard of it And I invested I said hey you should invest in this And they couldn't get there But my other friend Fred Wilson You were a portfolio entrepreneurial I was a portfolio company And I said hey you know This Twitter thing's gonna be big And this Zinga 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 Zinga deals.

[870] These are very important companies.

[871] And then my friend Fred Wilson, what did they say?

[872] They, they, I said they went the next day actually and tried to close Twitter, but they couldn't get their head around the valuations or whatever it was at the time.

[873] I'm not sure their exact objections.

[874] Both 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.

[875] And I was a Sequoia CEO.

[876] 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 for Mahalo before launching the product six months after I had raised my Series A. And I went from an $11 million valuation to $100 million valuation.

[877] Wow.

[878] And this is in 2006?

[879] Yeah.

[880] And 2006, yeah.

[881] And Mark Pinkis and Evan were like, how did you go from $11 million to $100 million before the product launched in six months?

[882] I was like, I don't know.

[883] And they were going for like $30 or $40 million, I think, each.

[884] And they were further along and their products were launched.

[885] I said, listen, Fred Wilson's East Coast, he's awesome.

[886] He's, like, one of my best friends for a long time.

[887] He helped me get in business.

[888] His wife, Joanne, worked with me at Silicon Air Porter as the salesperson.

[889] And also Joanne Wilson, his wife, worked with me at Silicon Air Reporter.

[890] And the reason it was so successful is she was the salesperson.

[891] And she was, like, I mean, it was two bulldogs.

[892] Like, she's a tiger.

[893] And she's now a great angel investor herself.

[894] Absolutely, yes.

[895] And just one of the great collaborators I've ever had in my career.

[896] And anyway, long story short, I said, listen, you know, your pay.

[897] between Fred, who's like the up -and -coming hustler, who will work hard.

[898] But, you know, he's East Coast.

[899] And a lot of people, you know, are, you know, Fred thinks Sequoia is the gold standard.

[900] Fred would tell you to take Sequoia's money.

[901] But I think Fred is great too.

[902] So I actually think it's a coin to us.

[903] You can't lose.

[904] And they were both struggling to take, which, who would take that deal?

[905] I think that gave me the credibility with Sequoia that they said, Jason keeps sending us these great deals.

[906] there's many more companies now.

[907] Jason has this collaboration with Arrington for TechCrunch 50 and they broke up and now he's doing this launch festival on his own.

[908] Rulov came up this idea.

[909] What if we raised like a $3 million, $2, a $3 million fund and we just gave everybody the ability to make $25 ,000, $50K checks?

[910] 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.

[911] That was the end of your company because you were then.

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

[913] Well, that works, too.

[914] But, you know, the idea is, like, you would, if your venture fund did not follow on, you were damaged goods.

[915] And nobody else would.

[916] And the higher profile of the fund, the higher profile of the signaling risk.

[917] So Sequoia was acutely aware of this.

[918] So they just said, the Scouts program, we won't announce, it'll be on the DL.

[919] You can tell people what it is when you make the check.

[920] You don't have to, you can.

[921] We just weren't sure what to do.

[922] And so I just went around town and I said, okay, I started this thing, Open Angel Forum.

[923] And I tried to kill something called Koretzu for him, which was charging people $5 ,000.

[924] So I went to war with them, and they got really upset and called Michael Moritz on the phone and told him, like, who is this employee of yours?

[925] He's like, not employee of ours.

[926] Well, he said he's going to kill the, he's going to kill the Koretsu for him.

[927] And he's like, why would he say that?

[928] And Maritz called me. And he said, did you, Jason, did you tell them you were going to murder them?

[929] I was like, yeah.

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

[931] No, no, Michael Maritz was not angry.

[932] He's like, well, why would you?

[933] You probably loved him.

[934] I'm just curious.

[935] And Moritz is cool as I's.

[936] He's the greatest.

[937] And I said, well, they're charging founders $5 ,000 to meet Angel investors.

[938] He goes, oh, that's terrible.

[939] I said, yeah, so I want to kill them.

[940] He's like, oh, okay, carry on.

[941] That was the end of the phone call.

[942] It was great.

[943] So great.

[944] Oh, so great.

[945] So anyway, I started Open Angel for him.

[946] And I just started, you know, thumbtack, style seat, data stacks, all these signposts, all these great companies just came.

[947] And Uber actually.

[948] And Uber came.

[949] And Uber came.

[950] Yeah.

[951] And Uber came, yeah, and on the spot myself.

[952] Saka was there, but Saka knew Travis before.

[953] And Sion Bannister invested in them.

[954] I introduced Siam Bannister to Thumbtack and Uber.

[955] She's always been very gracious about giving me credit for that.

[956] And 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.

[957] Who knows?

[958] You know, like a success has a million.

[959] A million father.

[960] Father, failures, an orphan.

[961] Okay, so all this is go, what's going through your head as this is happening?

[962] Like, you're running Mahalo.

[963] Mahalo is super high.

[964] Yeah, I mean, they had no. You know, Sequoia anointed me. Now I became dangerous because now I wasn't just East Coast anointing.

[965] I was West Coast anointed.

[966] You understand?

[967] Yep.

[968] And nobody really had ever done that.

[969] That was a very unique thing.

[970] And I knew it.

[971] I think a lot of our audience probably has not ever heard of Mahalo.

[972] So fill us in real quick on that.

[973] So anyway, I had this idea.

[974] I emailed Michael Moritz, John Doer, and Mark Cuban.

[975] And I said, I have an idea for my next company.

[976] I didn't know any venture capitalists.

[977] Even through all of this, I really didn't know any of the West Coast Venture Capitals.

[978] But I knew John Doer and Michael Moritz were the number one and number two, probably in reverse order.

[979] Michael Moritz and John Doer.

[980] But anyway, there's an argument about that.

[981] I had run into Moritz one time at like a conference.

[982] He wouldn't remember me. But I emailed Michael Moritz and I said, I have my next idea for a company.

[983] I sold my last company to AOL for $30 million, $18 months after I started it.

[984] Would love to get your advice.

[985] Shortest email possible with a little microphone dropping it.

[986] And Moritz called both of my phone numbers and email me and his assistant called me all within one hour.

[987] hour of me sending me. I was going to ask how many minutes did it take to respond?

[988] John Doer, somebody on his team, got me the next day.

[989] I was in both their offices next week.

[990] And also Mark Cuban said, because I think when we sold, we turned his 150 into five or six million.

[991] So he said, put me down for a million or whatever you want, Jason.

[992] I think there was actually a second payment coming.

[993] And he just seized his attorney and said, whatever the second payment is for the AOL thing, it was like a million bucks.

[994] He said, just throw it into Jason's next thing, which is, you know, very Mark Cuban thing to do.

[995] Okay.

[996] So here's the question.

[997] Did you actually have the idea or did you just send me an email?

[998] And my idea was I had gone to Wikipedia was like the thing at that point in time.

[999] And I went to Wikimania, which was like their conference up in Boston.

[1000] And I studied the wikis software.

[1001] I started playing with it.

[1002] And I made a little proof of concept where Google was dealing with web spam at the time.

[1003] And the order of the links weren't very good.

[1004] My wife's Korean.

[1005] And I had heard about Daum, d -a -um .net, and comprehensive search in Korea.

[1006] And in Korea, Dowell owned the blogging company and the picture hosting company.

[1007] And they, when you did a search, they would show pictures, they would show links, pictures, and blog posts on one page.

[1008] And so I made this comprehensive search and I said it's going to be called 20 .com, the top 20 links for any keyword.

[1009] And I went into the meeting and I put three pieces of paper on the table.

[1010] And I don't think I've ever told this story.

[1011] And I said, iPod, look at these 10 blue links.

[1012] These are the search results.

[1013] One's Yahoo, one's 20 .com, and one is Google.

[1014] Which one do you like best?

[1015] And Moritz and Roloff pointed to the one, and they turned it over.

[1016] I said, turn it over.

[1017] And it's 20 .com.

[1018] I said, turn the over to over.

[1019] I did it again.

[1020] I said, Kauai vacation.

[1021] And they picked mine again.

[1022] And they said, why is yours the best?

[1023] And I said, I had a human look at the Google result and make a Wikipedia page.

[1024] And they said, that's great.

[1025] And I said, that's great idea.

[1026] What are you looking to do?

[1027] I was like, I want $3 million for 25 % of the company.

[1028] And he said, okay, work with Roloff.

[1029] And he walked out.

[1030] And he was on the board of Google.

[1031] He's like, I can't be on the, I can't do this, but Roloff can.

[1032] And it's not competitive with Google.

[1033] It's, you know, it's a wiki, whatever.

[1034] That was the start of it.

[1035] And then my friend Elon put some money in.

[1036] He was just casual.

[1037] Working a rocket company.

[1038] He just called me. He's like, I think you're smart.

[1039] I'll put some money in.

[1040] And then Rupert Murdoch put some money in.

[1041] CBS puts the money and just a bunch of people.

[1042] And, you know, whatever.

[1043] I was on the top of my game, got the company a $10 million in Google AdSense revenue.

[1044] And then Matt Cuts felt like we were getting too big and EHOW was getting too big.

[1045] There was also Cosmix, right?

[1046] Yeah, Cosmix, WikiHow, there was a whole cohort of us making content.

[1047] And let's pause for a minute just to catch everyone up on Matt Cuts.

[1048] So Matt solved a really hard problem for Google over the course of a decade, which was basically link spam.

[1049] 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?

[1050] Yeah.

[1051] And I think Matt actually is leading a really important initiative now in the federal government at the U .S. Digital Service.

[1052] Well, what would happen is our pages were so good that Kauai Vacation would rank in the top five and people would blog about it, link to it and ask us to update the links.

[1053] And then we started putting content on the pages.

[1054] So we had content on the pages.

[1055] So basically Google, this was all on their roadmap, but I created was on Google's roadmap five years, ten years before they got there.

[1056] Because if you Google, go quiet vacation on Google.

[1057] You get that now.

[1058] So I was five or ten years ahead of them, and they were going to do it machines that Marissa said, I don't think Jason's right.

[1059] We had this like debate at a conference at one point.

[1060] Somebody asked her about Mahalo.

[1061] I don't think humans can scale.

[1062] We're going to do with robots.

[1063] Anyway, then they basically took 90 % of our traffic away.

[1064] And the punchline was they took 90 % of their own revenue way because the way we were monies.

[1065] was with their tools and then I said to Matt and I called up Sergey Brin and I called up everybody I knew there and I was like what are you guys doing you just killed my site?

[1066] I have to lay off 100 people and we got in this big public spat and they're like yeah you know we don't know and I was like well we're partners and Matt Cutts was like we don't have partners and I was like I forwarded him the email from the AdSense team that said partner meeting and that they you know 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.

[1067] And this is why I think, you know, Google will face antitrust action like they did in Europe, maybe here eventually.

[1068] And I think Yelp's right.

[1069] What they did to Yelp.

[1070] Yeah.

[1071] It was the same thing.

[1072] It was equally bad.

[1073] I mean, they basically studied us, copied us, killed us.

[1074] But I mean, I learned a really important lesson there, which is, like, don't have a dependency.

[1075] But the problem was, you know, just the thing grew so quick.

[1076] I was like, we're making, we're not a $10 million runway.

[1077] We're making just a lot of money every day at the peak in AdSense and this is all hunky door.

[1078] I was like, they'll never shut us off.

[1079] We're sending, we're giving 30 cents of every dollar to them.

[1080] Yeah.

[1081] And I was wrong.

[1082] You know, they had a long game.

[1083] They just didn't want Mahalo .com and other things to exist.

[1084] So they killed us.

[1085] And then I pivoted it to inside.

[1086] And it's still going today, 12 years later.

[1087] And, you know, it's actually doing really well for email newsletters.

[1088] Wow.

[1089] What's old is new again.

[1090] Exactly.

[1091] So what's going through your head at this point in time about like, okay, what is your, next act like like well the scouts thing i didn't take too seriously i just thought it was a fun diversion um and then they got about i don't know halfway through the program and roloff said to me you know nobody else is making investments i think like sam did stripe or something you did uber and you did four and sam did two sam walton had done stripe and uh they said you know this fund we might not do another scouts thing so you know you got like a million left in the fund and i was like oh you don't have to tell me the buffet's over the fund is uber Stripe, thumbtack, data stacks.

[1092] Data stacks.

[1093] I mean, that fund is the greatest fund in Sequoia's history on a percentage return basis, I believe.

[1094] I don't know that for sure.

[1095] And they're saying to you...

[1096] Not on cash, though.

[1097] Not on cash.

[1098] On multiple on cash.

[1099] On multiple cash, it's definitely in their top five, I would think.

[1100] And they're saying to you, we don't know if we're going to do this again.

[1101] Well, it was very early days.

[1102] We didn't know.

[1103] And they're like, we still have all this money left in the fund.

[1104] So, Rolf was like, if you want to make some more.

[1105] So I did 19 investments.

[1106] I put 700 to work.

[1107] It became worth over $100 million in.

[1108] total, largely due to an Uber.

[1109] And then my friend Naval had been coming to the Open Angel Forum because he was doing venture hacks and he was an angel investor.

[1110] And he said, listen, I'm going to start this thing angelist.

[1111] And it's kind of competitive.

[1112] And I was like, no, this is, you're doing online.

[1113] Online is dumb.

[1114] You know, like, nobody's going to invest online.

[1115] It's all in person.

[1116] And he's like, yeah, I disagree.

[1117] And I was like, yeah, I don't know, Naval.

[1118] I don't think, I don't see anybody investing blindly online.

[1119] He said, well, this is new thing, SPVs and syndicates.

[1120] I was like, explain that to me. And he explained it to me. And I was like, I don't understand it.

[1121] Explain it to me again, explain it to me again.

[1122] And then he sent me a link and it was, you know, angel.

[1123] dot co slash Jason South Syndicate.

[1124] And it said, you know, set up your syndicate here.

[1125] And I filled out the stuff and I tweeted it.

[1126] And then he called me in the front.

[1127] What are you doing?

[1128] And I said, what are you not supposed to tweet it?

[1129] I said, it says on the page, tweet your syndicate.

[1130] He could say, I didn't launch it yet.

[1131] It's launching on Monday.

[1132] And I said, oh, I'm sorry.

[1133] You want me to take that?

[1134] And it's like, no, don't worry about it.

[1135] TechCrunch got the embargo, but they're upset.

[1136] Nobody's on Twitter.

[1137] And it's also so interesting that, like, in your head, you're like, this is, I don't, I don't get it.

[1138] Why would people sort of like invest alongside another person without ever meeting the company in person?

[1139] And that's what Sequoia was doing with you.

[1140] They were giving you money and saying, yeah, no, I'm, listen, Ben, I'm not saying I'm the smartest guy in the class, all right?

[1141] I never said that.

[1142] That's not my claimant.

[1143] I'm a hustler.

[1144] 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.

[1145] I'm not a complete fraud I'm kind of me being self -deprecating but you know I'm definitely been lucky and I'm definitely good at hyping things so I mean that's why Naval sent me the link anyway a bunch of people join Tim Ferriss launches his I don't think we should glaze over this like the set of people you've already talked about clearly there's something special about the way you build relationships I mean you're I'm fun to spot yourself like 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?

[1146] Like helping them, knowing that over the next 10 years, that's going to be a good bet.

[1147] I think enthusiasm is contagious.

[1148] So I've always been very enthusiastic at what I do.

[1149] And I always pick up the check.

[1150] And I always set up dinners with a lot of people.

[1151] And I always introduce people to other people with no intent of capitalizing on that.

[1152] Like Tim O 'Reilly invited me to a food camp early on where Larry Page came in his helicopter and landed it outside of food camp.

[1153] And I was like, Larry, what are you doing?

[1154] Like, you realize how douchey it is to land your own helicopter?

[1155] He's like, do you think so?

[1156] I was like, dude, come on, man. Just land it at the airport.

[1157] I mean, we know you're rich.

[1158] Like, you don't have to fly your helicopter from Palo Alto.

[1159] He's like, you're probably right, Jason.

[1160] I totally admonished Larry Page.

[1161] It was pretty funny.

[1162] But he did literally have them clear the field so he could land his helicopter.

[1163] He was taking helicopter lessons at the time at Foo.

[1164] So I'm not speaking out of school.

[1165] He literally landed his helicopter there.

[1166] Anyway.

[1167] Tim O 'Reilly said something about, like, I can't remember the exact phrase, you'll find it put in the notes, but he said something about like, if you extract very little from the network you're building, you do really well.

[1168] You don't need to attract all the value.

[1169] Yeah, it's like the Bill Gates platform quote.

[1170] Something like that, yeah.

[1171] But he evolved, he said it better.

[1172] We'll come to, but this is sort of thing about networks.

[1173] Anyway, so I was always just introducing people to everybody.

[1174] In fact, I remember when I was at the top of my game within Gaggett, I was at Sundance.

[1175] And my friend David Sacks was producing a movie there called Thank You for Smoking.

[1176] So we were all there.

[1177] I just saw Weblogs, Inc. Elon, myself, Sachs were all hanging out, my wife and his wife for the time, and Sachs' new girlfriend, who's now his wife.

[1178] And Walt Mossberg is there, and he says, hey, let's have lunch.

[1179] Because he knew I was there.

[1180] I was like, yeah, sure.

[1181] And I was like, hey, you know, let's meet over here.

[1182] I'm going to bring my friend Elon.

[1183] He's like, who?

[1184] I'm like, Elon Musk.

[1185] He's doing this thing or whatever.

[1186] And, you know, Walt Mossberg was very big there.

[1187] And he's like, he wrote me this in Monarch.

[1188] punishing email.

[1189] I agreed to have lunch with you, not Elon Musk.

[1190] You forcing me to have lunch with this person like is just unfair, like our friendship, whatever.

[1191] I was just like, okay, I won't bring him.

[1192] You know, Walt was very sensitive at the time.

[1193] Every was trying to get to Walt.

[1194] And so he felt like I was trying to put Elon in front of him.

[1195] And Elon didn't even know.

[1196] I was just like, Elon's here.

[1197] Elon wasn't running Tesla at time.

[1198] He was just an investor and he was doing the space like stuff.

[1199] I was like, you should make my friend Elon.

[1200] So you're good at?

[1201] I was always good at just connecting people and meeting people together and just hanging out with people.

[1202] Like, my book agent John Brockman had introduced me to Sam Harris.

[1203] You know, Sam was on my podcast, and he did like an AMA from a hollow.

[1204] They said, how do you do podcasting?

[1205] I was like, you know, you're built for podcasts.

[1206] He said, you think I should do a podcast?

[1207] I was like, absolutely, you're built for it.

[1208] He's like, what do I need?

[1209] I'm like, a guest in a microphone.

[1210] He's like, oh, I was like, you can use my studio.

[1211] Anyway, I convinced him to do a podcast, and now, like, the rest is history.

[1212] And I introduced Sam to Elon.

[1213] And then we all started talking about AI.

[1214] and Elon introduced Sam to the concept of AI and all this AI stuff going on in the book Super Intelligence and all that.

[1215] And then the people who write Westworld, Christopher Nolan and Lisa Joy, then met Elon and Sam.

[1216] And if you, like literally the entire season this year, I'm watching it.

[1217] I'm like, this is a conversation I had with the four of these people.

[1218] Like three or four years ago.

[1219] It's pretty surreal.

[1220] I always picked up the check and I always brought everybody to dinner.

[1221] That's why I guess.

[1222] how good at this and I'm you know we're not doing playbook this episode but this is the little that's your mini playbook just always buy dinner okay so I got to ask though that that playbook that mindset that wanting power and connecting people yeah as Mahalo is you know post panda going on the panda is the update that Google did yeah why do you not go join a venture capital firm and become a traditional venture capitalist Self -awareness, yeah.

[1223] I mean, I do.

[1224] You can't have to be a VC, as we all know.

[1225] Well, here's the thing.

[1226] It's called the venture partnership, and that's not what I do, right?

[1227] Like, I like to make my own decision, and I'm, like, the solo artist.

[1228] Like, you put somebody like me in a band, the band will break up.

[1229] Like, not a good idea.

[1230] Right.

[1231] Your hero is Bob Dylan, not like Eddie better.

[1232] Yeah.

[1233] You know, like, I could play, you know, I could play with Tom Petty and the Heartbreakers.

[1234] but I'm going to write my own albums.

[1235] I want to do my own thing.

[1236] I don't want to, I want to keep it small and authentic and true to what I want to do.

[1237] 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.

[1238] You know, it would be a pretty good feeder.

[1239] You could plug what I'm doing into something bigger.

[1240] If you were a billion -dollar late -stage fund, imagine having, you know, the only real viable Y Combinator competitor out there as the top of your funnel, the only real angelist co -existor competitor.

[1241] These things are not really competitors when you think of them.

[1242] They're really co -existors, but we're the number one largest syndicate in the world, and Angelist is the largest collection of syndicates.

[1243] But if you took the top two or three syndicates together, they would be smaller than ours on Angelist.

[1244] And then you look at our program, like, we're really only people who compete with Angelist head, with a Y Combinator heads up.

[1245] Like, the only reason we've had people pick us over Y Combinator and people pick Y Combinator over us or go to Y Combinator and then come to us.

[1246] Like, we're really the only, I think, accelerator who can say that.

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[1266] Jason, I want to tee this up in this direction.

[1267] So you want to be a solo artist, not join a band.

[1268] I am a solo artist.

[1269] Not join a band.

[1270] Or I'm sorry, at this point in time, I'm just playing through what's in your head.

[1271] Yeah, yeah.

[1272] You want to be a solo barrage, but you also deeply understand returns to scale.

[1273] As you're thinking through this weekend 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?

[1274] Yeah.

[1275] 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.

[1276] And I did it with Ron Conway, and I did it with Ev Williams.

[1277] because my friend Dave Weiner had started, who created RSS, said, hey, Jason, check this out.

[1278] You can attach a file to an RSS feed.

[1279] I was like, oh, you could put a PDF in there?

[1280] It's like, yeah, you could put a PDF in there, but that's the same thing.

[1281] And I was like, oh, yeah, again, I'm not the smartest kid in the class.

[1282] He's like, check this out.

[1283] And it was an RSS feed with MP3s.

[1284] And I said, oh, he's like, now check this out.

[1285] And he sent me a little script.

[1286] And it took the RSS feed, and then it wrote the MP3 files as an out.

[1287] album into your iPod.

[1288] And the reason it's called podcasting is because you could sync your iPod on your Mac to an RSS feed that then put it there.

[1289] So the idea was you would plug your iPod in at night to sync and to charge to your Mac and also it podcast.

[1290] It would download at night, all those things.

[1291] And when you got on your commute, you'd have a couple podcasts on there.

[1292] And I was like, wow.

[1293] And then they convinced Steve Jobs to add it to iTunes.

[1294] to iTunes.

[1295] And there's a famous clip of me talking with...

[1296] 2006 or seven.

[1297] Yeah, and there's a famous clip of me talking to Steve at the D conference and asking him a question about it.

[1298] And I asked him about making money if we'd ever sell advertising on podcasts or whatever.

[1299] And he said, you know, it's a really good idea.

[1300] You should just email me, Jason.

[1301] And I said, yeah, the email I always email you at.

[1302] And he said, yeah.

[1303] And the whole audience left.

[1304] But I just said it as a joke like, you know, because I did talk to him on email.

[1305] And so I thought it would be funny to say, you know, like the email we always talk on.

[1306] I mean, although he cracks up, it's a very funny clip.

[1307] But anyway, I did the podcast because I just thought it would be fun.

[1308] And to me, it was just a fun way to promote my friends.

[1309] And so, you know, I had Brian Alvey on my longtime collaborates as a first guest.

[1310] David Sachs came on early.

[1311] Just, you know, Jason Azar was starting a company, just having people on when I was in L .A. And then Bing was going to launch it.

[1312] Somebody from Microsoft called me and like, hey, we love this podcast thing you're doing.

[1313] We want to tell you about something secret.

[1314] And I was like, what is it?

[1315] He was like, we're starting a surgeon.

[1316] And I was like, everybody knows.

[1317] He's like, yeah, it's called Bing.

[1318] I'm like, well, that's a terrible name.

[1319] And he's like, well, anyway, we want to advertise on your podcast.

[1320] This is 11 years ago.

[1321] And I was like, okay.

[1322] You hadn't thought about, you hadn't put two and two together.

[1323] There was no advertising in podcasts.

[1324] It was just like blogs.

[1325] It was just a thing.

[1326] But of course, it was just like when you're starting Silicon Allie reporter, web, like it's the same thing.

[1327] Anytime a new medium comes out, I assume it's going to work.

[1328] This is my big trick in life.

[1329] Whatever something comes out, I just assume it is going to reach critical mass. and I behave as such.

[1330] So when blogs came out, I was like, okay, I assume it's going to work.

[1331] I'm going to go full bore as if it's going to.

[1332] When podcasting came out, I want to full bore.

[1333] Whatever everything comes out, I just, if I'm interested in it, Twitter, the same thing.

[1334] I just want full bore on Twitter.

[1335] When has that not worked?

[1336] Oh, God, probably more times than I can count, but I mean, it's...

[1337] But it doesn't matter when it doesn't work.

[1338] Yeah, I mean, I have a Tumblr, you know, there's a bunch of path .com, friend feed.

[1339] There was a bunch of other things.

[1340] But if you take the Robert Schoble, relentless enthusiasm, like spastic, like, oh my God, this is going to change everything.

[1341] Google Buzz.

[1342] Google Plus.

[1343] You know, like I was all in on their services, too, and that was all wasted time.

[1344] But, you know, when it does hit, people remember the hits.

[1345] Like, it's just the same thing about it that you guys know that you guys know about investing.

[1346] And asymmetric returns, yeah.

[1347] Yes, asymmetric returns.

[1348] Correct.

[1349] If you get in early and you have the, you know, you're baking in whatever that service is and you got there early, you're going to, you're going to have a head start on everybody else.

[1350] So then it just worked from.

[1351] me. And then they bought, they were like, how much of the ads?

[1352] And I was like, um, uh, $3 ,000.

[1353] And they're like, uh, per ad.

[1354] I was like, yeah, but you have to buy 10.

[1355] And they're like, okay, $30 ,000.

[1356] And you just sent me $30 ,000.

[1357] And they're like, they're like, what is the ad?

[1358] I was like, I'll just talk about Bing.

[1359] And so they literally would just pull up Bing and I'd like, hey, check out this feature.

[1360] Check out that feature.

[1361] Thanks, Bing, Bing, Bing, Bing, and then then we'd be the end of the end.

[1362] It's pretty funny.

[1363] Um, so great.

[1364] Yeah, we just goofed off.

[1365] And we'd have puppets on the show.

[1366] We just, it was just this like vaudeville kind of approach to it.

[1367] 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.

[1368] You know how this stuff goes, 200 ,000, 300 ,000, all of a sudden it becomes a thing.

[1369] And what's the listenership on this week in startups now just to give people sense?

[1370] Over 200 ,000 per episode, yeah.

[1371] Yeah.

[1372] So you guys are right on my tails.

[1373] It's a niche podcast by design.

[1374] Like I could make it get bigger by dumbing it down or going shorter or having post -production on it.

[1375] But I just told everybody I'm not interested in that.

[1376] And, you know, Joe Rogan has taken the same approach, the same, you know, Howard Sterling, like approach, as you put the recorders on, as long as it's as interesting you go.

[1377] And we have three ad slots, and we sell them out every year.

[1378] And it does, you know, a couple million bucks.

[1379] And that's enough to pay for a seven, eight person team that works in the podcast now.

[1380] That's awesome.

[1381] And how does that play into your angel investing?

[1382] So to take us back.

[1383] Well, it's very simple.

[1384] Yeah.

[1385] I mean, I would say on the podcast, hey, you know, here's a company I invested and I'm having them on the podcast.

[1386] Or in the case ofcom .com, somebody had told me Alex was like a genius.

[1387] And I was like, why?

[1388] And he's like, well, did the million dollar homepage.

[1389] I was like, oh, that was genius.

[1390] He said, yeah, I was doing a meditation.

[1391] I looked at it.

[1392] It was a web page where you went and I just played a meditation in a loop.

[1393] And I was like, yeah, I'll have them on the podcast.

[1394] I need a guest.

[1395] You know, back then it was just like, can we get any guess?

[1396] And so Alex came on and so on the episode.

[1397] I said, hey, can I put 25K in, you know, for like 1 % or 2 % or whatever?

[1398] And he said, yeah, we talked about it.

[1399] You did this live on the episode.

[1400] I did it live on the episode.

[1401] And, you know, I was always trying to get somebody to do that and nobody would do it.

[1402] But I thought it was funny.

[1403] It was entertaining for me. Anyway, long story short, he, you know, I put 50K in for my fund and this Angelist thing had just come out and I made it the first deal on Angelist and my expectation was maybe another 25K would come in or 50K because they had like, you know, 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.

[1404] We had a 6 % or 7 % position.

[1405] That company's worth $1 .4 billion now.

[1406] It's the most successful syndicate in the history of syndicates.

[1407] In fact, it's probably the top three syndicates combined would be smaller than the composition.

[1408] And for people that have never used Angelus, how does that work where you're like, hey, I'm in for 50?

[1409] How is it that, like, well, the original deal was Angelus would take 5 % of the carry.

[1410] I would get 15%.

[1411] I subsequently negotiated an 18 and 2 deal, which led to a lot of animosity.

[1412] Eventually, Angelus and I broke up.

[1413] That's another sort of tale.

[1414] But, you know, Naval and I are friends still, but we were just a little too big for it.

[1415] And that's, you know, like, back to being very clear about, like, I'm not the bull you want in your China shop.

[1416] 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?

[1417] The answer is no. Because I'm going to do what I want and it's going to knock shit over inside your place, right?

[1418] Like, it's not good for you.

[1419] It's not good for your partnership.

[1420] 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, to me, would be purgatory.

[1421] That's your nightmare.

[1422] It's literally my nightmare.

[1423] Like I want to make an investment because I look at the founder's eyes and I push the chips in.

[1424] 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.

[1425] That's the opposite of what should happen in an early stage investment.

[1426] The second you debate it is the second you lose the outliers.

[1427] Because the outliers make no freaking sense.

[1428] So anyway, consensus equals death in the early stage.

[1429] Consensus at later stage equals protecting down.

[1430] at risk and due diligence and all that stuff.

[1431] It's very important.

[1432] I get it.

[1433] Can we digress for a minute before we pick back up with the story of your empire?

[1434] 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.

[1435] Yeah.

[1436] So here's the thing.

[1437] Imagine a poker table existed in the world where you would buy in for $10 ,000.

[1438] And there were 10 players.

[1439] So it's $100 ,000 on the table.

[1440] But every 100 hands, you could win a million dollars or $10 million.

[1441] So there was uncapped upside.

[1442] Somebody just gifted $900 ,000 extra dollars or $9 .9 million extra dollars to that table.

[1443] It would change the way people played.

[1444] It would change the game.

[1445] And that's called the World Series of Poker, by the way, for pros.

[1446] 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.

[1447] It's like for the pros, for Phil Helm Youth, 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.

[1448] It's the only way to get asymmetric upside in poker.

[1449] Correct.

[1450] I mean, there are ways, but yes, asymmetric for sure.

[1451] So anyway, once you realize that, that frees you from.

[1452] you trying to understand if the idea is going to win or not.

[1453] That's what Trips early stage investors up, which is why I wrote my book, is because I felt I had figured something out and wanted to share it with the world, which was, this is the greatest casino in the world, in my opinion.

[1454] 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.

[1455] And why is that?

[1456] 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, surrey sisters, ex -boyfriend's brother, and because you're going to build an Instagram competitor that has links in the comments.

[1457] Because Instagram doesn't support links in the comments.

[1458] Like, that's the reason, like, they're going to exist.

[1459] And they put the 250 in.

[1460] The product never gets released.

[1461] They give that 250 to Dev Shop in Estonia, that never finished.

[1462] They asked for another $250, they give the other $250 ,000.

[1463] The product comes out, nobody cares.

[1464] They shut it down.

[1465] Those people go work at Boston Consulting Group or whatever.

[1466] And they made one bet, so it was literally like walking up to blackjack and putting your entire sack on one hand.

[1467] Like, it's just not enough of...

[1468] Or like in poker league betting, you go in all in before the flop.

[1469] Yeah, before you look at the cards.

[1470] You're just like, I'm going to sit at this table and put it all in on the first hand.

[1471] Which I know some people who do that for fun.

[1472] 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, you know, 12, 15, 20 company portfolio, it's mathematically the same thing.

[1473] You're taking way too concentrated on a bet.

[1474] Really, and you need to really hit 20 or 30 or 40 in what I've seen in angel investors who succeeded.

[1475] And you have to be investing in a certain pool of entrepreneurs.

[1476] 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.

[1477] If you're reading scripts in Hollywood as a first -time director and the script got to you, that means every pretty director has passed on it and never got to the good director.

[1478] So just understand that.

[1479] Okay, so this is what I want to go deeper on.

[1480] Because I think there's a really important insight here.

[1481] How do you square what you said a minute ago about consensus, at the early stage consensus kills because you want the crazy stuff you can't predict.

[1482] right with this aspect of you need the high quality like what is the signal and the quality yeah so what i teach we have a course called angel university that goes along with angel the book and in that course i explain to people that when you make your first 20 or 30 bets make as small a bet as possible which means using syndicates is a good idea forget about mine just sign up for everyone because it's free to read the deal memos and you learn but if you do that you're playing at the lowest stakes poker table while you learn.

[1483] Like literally, if you could play $1 blackjack, if you want to learn blackjack, sit at the $1 blackjack table instead of the $100 a hand.

[1484] Because you're going to lose a minimum, and it doesn't matter if you lose, it's just the education, it's like paying for an educational course.

[1485] 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.

[1486] you've now eliminated, as you guys know, 90 % of the failure rate.

[1487] 90 % of the Trishian in startups comes from, they never ship the product.

[1488] Then you get down to that 10 % of that, 90 % of those never get a paying customer.

[1489] So if you were as you're a starting angel investor to only invest in companies with some amount of revenue, even as little as 2 to 10 ,000 a month, you probably have eliminated 80, 90 % of the risk.

[1490] So start there while you're learning.

[1491] And then as you get more sophisticated, just like in poker, if you want to play, under the gun with Phil helmet at the table and you want to play 9, 10 suited?

[1492] Okay, maybe if you've been playing for 10 years.

[1493] 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.

[1494] There's five times you could have invested in calm, maybe three, four, five times a calm, three or five times in Robin Hood.

[1495] Even these outliers, Airbnb, you probably have four or five chances to invest in Airbnb as an angel investor.

[1496] It's a misnomer that you're going to miss the deal.

[1497] Like what Y Combinator does to angel investors and telling them, if you don't invest quickly, Within these 48 period, the deal's closed and you miss them forever.

[1498] It's like just literally not true.

[1499] It's literally they try to create a false sense of urgency.

[1500] They train the founders to do this.

[1501] And it's nonsense.

[1502] Not only is that round not closing immediately, there's going to be four rounds after that you can get into.

[1503] No great investor invests at demo day.

[1504] Well, especially now with safes and not price rounds.

[1505] Like, it's rolling.

[1506] I mean, it's not.

[1507] It's rolling.

[1508] Super rolling.

[1509] There's one thing you said that I think is really insightful.

[1510] 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.

[1511] And then once you get better and better and better and you become Jason Calacanus, you can invest in calm.

[1512] Why are you comfortable at the level you're at investing in a no -revenue meditation website?

[1513] Why was that okay?

[1514] Yeah, so I can take you to the background.

[1515] It was very simple.

[1516] I had known Sam Harris.

[1517] I had done positive visualizations.

[1518] I had heard that term, and I used that in sports because I was a psychology major.

[1519] I had done positive visualizations to get through the New York City Marathon, which I did 11 of.

[1520] I didn't know it was called meditation, but I just positively visualized myself along the route.

[1521] 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.

[1522] Then when I saw calm, I talked to Sam Harris about it because he was studying, you know, he was doing cat scans of brains and he was a meditator and into psychedelics and all this stuff.

[1523] And he put me in touch when I was doing my research on com with a woman who ran the mindfulness center at UCLA.

[1524] And I found out that Phil Jackson, who I'd known when I was in L .A., when he was coaching the Lakers, I had become friends with him.

[1525] And he had Kobe and Shaquille O 'Neal meditating.

[1526] And I just, it clicked for me. Wait a second.

[1527] Phil Jackson, innovator, Sam Harris, innovator.

[1528] There's something at UCLA around the corner for me in Brentwood.

[1529] They're studying it.

[1530] they have a program, they're teaching people this.

[1531] Oh, they're studying it on PTSD soldiers.

[1532] This is the future.

[1533] But unlike yoga, which also started in Santa Monica, this can be delivered through your ears.

[1534] Wait a second.

[1535] Yoga you have to do in person, and yoga's everywhere.

[1536] But meditation is delivering your ears.

[1537] If this does work and it becomes as popular as yoga, there could be 100 ,000 people paying for this.

[1538] It'd be like a $10 million a year business.

[1539] companies were $4 million.

[1540] This could be like the future.

[1541] And that's when it all clicked for me. And it was like an easy bet for me to make.

[1542] And then the subscription service came out and Apple allowed subscriptions.

[1543] And when I think we invested in, when we invested in common, I think they had done $10 ,000 in revenue, you know, selling a month doing $10.

[1544] Okay, so it was a post revenue startup.

[1545] They had post revenue.

[1546] Yeah, yeah, they did.

[1547] But with Robin Hood, they didn't.

[1548] Robin Hood hadn't launched yet.

[1549] 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.

[1550] I'm not saying you can't do this, but if you want to reduce the amount of pain you're going to go through and you want to have a less painful junior year, like your junior year as an angel investor when you hit the J curve is so painful because you think you're an idiot.

[1551] You've deployed all your money, nothing's breakout yet, and you don't have any, you can't keep investing.

[1552] Oh, and half your portfolio can't raise money and it's shutting down.

[1553] And the other half can barely raise money and they're begging you for a bridge.

[1554] like literally the junior year everything tells you to quit and then all of a sudden you're four or five or six you know Travis calls up and he's in six cities and he's closing around with menlo at 300 million and you're like wait a second five million times 60 and holy that's a lot of money you know you start saying oh whoa this could work and that's when you once you hit one of those unicorn type investments then all of a sudden it clicks in your brain brain, your brain chemistry changes.

[1555] You have to have the brain chemistry change from being risk averse and outlier averse to outlier obsessed.

[1556] I am outlier obsessed.

[1557] I do not care about losses.

[1558] I literally, and that took me a long time because remember I was such a rabid competitor.

[1559] The idea of being fine with losing all the time, like imagine losing 29 nights in a row at poker.

[1560] But on the 30th night, you hit a 5 ,000 X or a 200 X. Right.

[1561] 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.

[1562] Correct.

[1563] 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.

[1564] And like, as you're making these angel investments, keeping them very small and thinking of them as experiments that like to me that seemed as like a really good mental trick to be like it's not a loss it's a failed experiment 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 oh six or seven companies great I'll just copy that seven companies and Paul was the draw right and now it's the legacy's the draw Paul Graham's not the draw it's the legacy so I said okay well if Paul was the draw I know I'm a draw So let's see if it works.

[1565] And I just said 7 % of, 6 % of preferred for 100K, which is a $1 .7 million implied valuation.

[1566] So, we'll go with that.

[1567] We'll just start accepting seven people at a time and deploying 700K at a time.

[1568] But then I added something, which was, you know, YC, imagine if YC an Angelliss got married or merged.

[1569] What would that look like?

[1570] Well, that's what I had.

[1571] and I had left Angel List and I had started the syndicate .com and it took me a while to get that domain name, but I got it.

[1572] Coveted to that one.

[1573] I'm a domain name coveter.

[1574] I'm a brander.

[1575] Anyway, the point is I started saying to people, I'll put in 50K for, the original deal was like 50K for 5%.

[1576] I'll put in 25K for 5%.

[1577] Then I'll put 25K at whatever your recent round is and then I'll syndicate it.

[1578] And then it was too hard to just syndicate all of them because not all of them wanted to do the syndicate.

[1579] So then I just said, okay, we'll put in 100K.

[1580] It's the same deal as Y Combinare at the time.

[1581] So then we're betting on these for a 1 .7, you know, rounded up to $2 million valuation.

[1582] And 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.

[1583] And then, like, two of the best companies raised rounds.

[1584] And the founder was like, well, we have no room for you.

[1585] I'm like, what?

[1586] I was like, I introduce you.

[1587] So I called up those people who were doing the rounds, and I read them the Riot Act.

[1588] I said, I introduce this company.

[1589] How dare you try to muscle me?

[1590] I said, you're swinging an elbow at me?

[1591] I said, I'm the point guard.

[1592] I passed you the ball.

[1593] And now you're not passing the ball back when you're triple team.

[1594] Like, pass the ball, move for the rock.

[1595] And I got both of those people to give me allocations.

[1596] And then I was like, well, this is not how power is supposed to work.

[1597] Like, if I'm the point guard, I have the power.

[1598] I have the power to freeze you.

[1599] So then I said, okay.

[1600] now the freezing will be in.

[1601] So I wrote into our documents that we have the right to do half the next round.

[1602] It's a hefty pro rata, my friend.

[1603] Not if you're Jason Calcanus.

[1604] And not if you're the founders.

[1605] It's a feature, not a bug.

[1606] Yeah.

[1607] It's a feature for the founders who we work with because they can start their fundraising with me as an anchor.

[1608] And they do.

[1609] And do you?

[1610] So do you pick winners?

[1611] Do you say, hey, you three, you guys are getting half the round from me?

[1612] Yeah, we've evolved it over time.

[1613] 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%.

[1614] And we've done that.

[1615] And then we'll let other people invest in it, but we'll actually price the round and put it in 500k or 250k and get them started.

[1616] 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.

[1617] When you get your term sheet, give it to us, we'll have five business days or something to make a decision and we'll let you know what allocation we want to take.

[1618] But we'll usually do it in a day or two, which is actually what Y Combinator announced they're doing now.

[1619] That they're doing now, yep.

[1620] Yeah, so they switched to my position.

[1621] And because I think they were experiencing the same thing, which was they were getting boxed out of their winners.

[1622] And so now we just say, give us the term sheet.

[1623] And if it's a reasonable term sheet.

[1624] It's not like something outrageous or non -traditional.

[1625] Like, we had one of our successful companies do a deal for common shares at a ridiculous price with some non -traditional private equity firm, and we passed.

[1626] We said, we'll just stick with our 6%.

[1627] But other times, we'll put in 500K.

[1628] And so for a company like FitBod, a major breakout for us, they came to us with just $2 ,000 a month in revenue, I think, or maybe $1 ,000.

[1629] And they've been public about, you know, hitting eight figures in revenue.

[1630] They were public about that at the launch festival.

[1631] They gave a keynote.

[1632] And I offered them live on stage, $2 million out of 50 million posts.

[1633] But anyway, we wound up putting more money in a couple of times.

[1634] You know, we built our position up to, you know, over 10%.

[1635] So that's what I'm trying to do now is just get to 10, 15, 20%.

[1636] And eventually, you know, with our fund, the syndicate, you know, and the accelerator, we can make three or four bets in the company.

[1637] and get to know the founder.

[1638] And if we can do this three or four bet thing, we'll be the first people to combine Y Combinator, Angelist, slash seed invest, slash republic, whatever crowdfunding, you know, syndicate you like, with a seed fund, like homebrew or pear or whatever.

[1639] So that's what I'm constructing right now.

[1640] We don't have a proper series A because we don't need to because the fund plus syndicate kind of hits the one, two million dollar number.

[1641] But, you know, the next fund, perhaps, we'll be able to do a full A, like a $5 million A. But I don't need to do that.

[1642] I kind of like being in the early stage.

[1643] It gets less interesting for me to go and do the, you know, big checks.

[1644] And there's so many specialized people at that.

[1645] I'd rather hand it off to Sacks or Chimoth or Bill Gurley or, you know, Rulhoff or somebody like that.

[1646] Our sponsor for this episode is a brand new one for us.

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[1648] So many of you reached out to them after hearing their CEO, Vijay, on ACQ2, that we are partnering with them as a sponsor of Acquired.

[1649] Yeah, for those of you who haven't listened, Vijay's story is amazing.

[1650] Before founding Statsig, Vijay spent 10 years at Facebook where he led the development of their mobile app ad product, which, as you all know, went on to become a huge part of their business.

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[1660] Customers include Notion, Brex, OpenAI, Flipkart, Figma, Microsoft, and cruise automation.

[1661] There are like so many more that we could name.

[1662] I mean, I'm looking at the list, Plex and Versel, friends of the show at Rec Room, Vanta.

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[1664] Also, Statsig is a great platform for rolling out and testing AI product features.

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[1672] You can click the link in the show notes or go on over to statsig .com to get started.

[1673] And when you do, just tell them that you heard about them from Ben and David here on Acquired.

[1674] Well, Jason, this has been, like, so fun.

[1675] We've got to do this more often because it's incredibly fun to riff with you.

[1676] I think this is a good place to call it for the main show here.

[1677] 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, you know, winning the deal, helping, and then future access to capital.

[1678] It's really interesting what you're doing.

[1679] And I also want to discuss the way that all these things tie.

[1680] together and how you sort of view the flywheel or the funnel or how you how you sort of visualize it.

[1681] And then I know you've got some good insider stories.

[1682] Good insider stories for sure the couple you brought up.

[1683] And also like frankly, the way you see the world.

[1684] Yeah.

[1685] I'm sure there's a hot take in there.

[1686] I got a hot take post -corona.

[1687] Yeah.

[1688] Yeah.

[1689] Yeah.

[1690] So.

[1691] All right.

[1692] Listeners, thanks so much for going on the journey with us here.

[1693] LPs.

[1694] Spend the hundred.

[1695] Spend the hundred bucks become an LP member like me. All right.

[1696] Listeners, thanks.

[1697] LPs will see you on the other side.

[1698] Thank you.