ACQ Sessions: Jason Calacanis

[0] So wait, it would have a magazine?

[1] Magazine, yeah.

[2] That's how I started, yeah.

[3] You said more?

[4] Magazines was like the original platform for...

[5] Wait, are we started?

[6] Silicon Alley...

[7] I guess we started.

[8] This is the trick.

[9] We've just been reporting the whole time.

[10] Yeah, but...

[11] Welcome to Acquired Sessions.

[12] All that stuff that you said beforehand, that, like, is really juicy.

[13] I don't think we should put that in.

[14] No, definitely not.

[15] Definitely not.

[16] We don't want to tell people where the bodies are buried.

[17] Well, cheers, boys.

[18] Here we go.

[19] This is the...

[20] Is this the first one or...

[21] This is the first in real life?

[22] Wow.

[23] I think this is our...

[24] Ninth, 10th, together, something like.

[25] like that.

[26] A lot between the two pods, yeah, for sure.

[27] Great to know you, boys.

[28] So this is the first Acquired Sessions.

[29] Acquired Sessions.

[30] I feel like I should get out of a guitar here and just play some Dillon.

[31] This is your baby.

[32] What is Acquired Sessions?

[33] Acquired Sessions is normally on the show, we are like so scripted.

[34] Yeah, you are.

[35] And we have a great time.

[36] We do four -hour episodes, you know, it's awesome.

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

[38] And just chop it up.

[39] And we just chop it up.

[40] And we just chop it up.

[41] David Rosenthal Unplugged.

[42] Wow, I love it, I love it.

[43] This is the literally MTV unplugged.

[44] Literally.

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

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

[47] 85 % of the Fortune 500 runs on them, and they have quickly joined the Microsoft's at the NVIDIAs as one of the most important enterprise technology vendors in the world.

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

[49] They're also a major partner of both Microsoft and Nvidia.

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

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

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

[53] 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.

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

[55] For example, smarter self -service for changing 401K contributions directly through AI -powered chat, or developers building apps faster with AI -powered.

[56] code generation, or service agents that can use AI to notify you of a product that needs replacement before people even chat with you.

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

[58] 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.

[59] So if you want to learn more about the ServiceNow platform and how it can turbocharge, the time to deploy AI for your business.

[60] Go over to servicenow .com slash acquired.

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

[62] Thanks, ServiceNow.

[63] That's great.

[64] So, well, we have no agenda, obviously, but, um, wait.

[65] Where do you want to start?

[66] We've got to think Vanta.

[67] Oh, yes.

[68] Oh, Vanta.

[69] I'm an investor.

[70] We're investors too.

[71] Well, great.

[72] They're an awesome company.

[73] Big supporter of podcast.

[74] So, yeah, go Vanta.

[75] We are huge fans of Vanta and their approach to the whole compliance.

[76] process, SOC2, HIPAA, GDPR, and more.

[77] And we've got CEO and co -founder Christina Cassiopo back with us today.

[78] Vanta was already the best place to check the box and get security compliance certified.

[79] But now you've just launched Vanta Trust Reports, which take things even further.

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

[81] Really excited about these.

[82] So actually a bit of not yet told Vanta history, but something like Vanta Trust Reports, honestly, a much worse, much more poorly designed version, but yours truly, which is why I can say that, we're launched in the very early days of Vanta when we wanted to help company get secure and prove that security, but weren't yet convinced we wanted to or had to go all through the nuances of what a SOC2 was.

[83] So we figured, hey, let's just make this report of the best security practices.

[84] Let's check companies against those practices all the time and make this live and updating visible and transparent.

[85] This should help these companies prove their security and grow their business.

[86] And it should also help them be more secure because they've got this report, like this kind of security status page out in the wild.

[87] So 2017, Vanta tried this and found out that no one really knew what a Vanta report was, and everyone wanted to sock too.

[88] So flash forward to 2022.

[89] And it's actually really exciting.

[90] Turns out creating standards is, you know, people have to know who you are before you can create your own standard.

[91] A little bit.

[92] You know, and so honestly, like, literally, I'm joking, but I'm not.

[93] Like literally the company strategy on that day sort of became, okay, use the existing standards to bolster yourself and build something better here.

[94] And so this launch of trust reports is really exciting.

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

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

[97] But then rather than keep going through their buyer's process, they're like, look, this is just constantly up to date and has all the information you need, you know, take a look at this instead, rather than my, you know, compliance PDF from months ago.

[98] So relative to a SOC 2, which is done once a year, and kept up to date annually, a Vanta trust report is kept up to date to the minute, basically, continuously.

[99] You always know what the company's practices are.

[100] So just really excited to get this out into the world and into folks' hands.

[101] Our thanks to Vanta, the leader in automated security and compliance software.

[102] If you are looking to join Vantas 2000, nay, 3 ,000 customers to get compliance certified in weeks instead of months.

[103] You can click the link in the show notes or go to vanta .com slash acquired for a 10 % discount.

[104] Thank you, Vanta.

[105] So in the juicy stuff earlier, you mentioned Mahalo.

[106] Yeah.

[107] I don't know, is that why you started the podcast?

[108] Can we just keep her like referring to the juicy stuff?

[109] the juicy stuff.

[110] Yeah, yeah, yeah.

[111] Is Mahalo why you started, you went from print to print to?

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

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

[114] He became like he got behind and the Fed showed up one day and this was the maybe six weeks before I was set to go to college and he said hey son I can't help you with college, good luck and I might be going to jail so take care of your mom.

[115] So he was like really behind on his taxes and you know a state liquor authority that kind of take it serious.

[116] So feds come.

[117] shotguns, the whole thing.

[118] They seize the place.

[119] They seize everything in it.

[120] And I was like, well, I guess I'm going to school at night.

[121] And I'm going to work during the day.

[122] And I worked fixing laser printers.

[123] And that was like a really good racket.

[124] The HP had just come out.

[125] Were you set to go to college somewhere else?

[126] Well, that's another story.

[127] But I was set to go to Brooklyn College.

[128] I got into that.

[129] I had also taken the police exam to be a police officer.

[130] So my brother went into the force.

[131] And then I said, you know what?

[132] I'm going to see if I can go to college.

[133] and make that work.

[134] So I'm going to go to Brooklyn College.

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

[136] And I would work fixing laser printers all day.

[137] I was a bad student.

[138] I was always that student who underperformed.

[139] I didn't find great meaning in academics, but I had a computer when I was in high school that I was more interested in playing with my 300 board modem, which then became a 1 ,200 Brow modem and my PC Jr. So it kind of, you know, like many people of that era, we were sort of set on a path because we were the first generation to have a computer at home.

[140] I actually had an Atari 2 ,600, and it could play Tank, was the game that came with it in Pong.

[141] And so my dad bought this for us when I was six or seven years old, 1976, 1977, and he had one of the first Pongs in Brooklyn in his bar.

[142] He must have cleaned up on that.

[143] Oh, my God, it was crazy.

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

[145] Like, computers are going to change everything.

[146] And then I happened to hack some software.

[147] We used to, I ran a lot of scams.

[148] You told us about the VHS.

[149] So VHS.

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

[151] So we were, we would make copies of like chess master and stuff like that and then sell them for $10.

[152] And then we started like hacking and doing what was called phone freaking.

[153] When you were doing this stuff, like it's, you'd be reasonably technical to do it.

[154] Not like the, the, You know, not like Wozniak technical, but like, you...

[155] We solder chips sometimes.

[156] We changed...

[157] Yeah.

[158] To put memory in at that time, you had to like take the memory chips and put them in and then bend them over and stick them in.

[159] Did you ever think about, like, did you consciously ever make a fork where you were like not tech media?

[160] And of course, media about tech, but you're like, I'm not going to be the guy doing the boards.

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

[162] It's a very good question.

[163] I used to go to Bleaker Street and I used to hang out in the West Village or the East Village It was like the cool places to hang out And like a thing to do would be to go to Tower Records And look at the zine section So there was a concept of a zine Which was short for magazine But a zine was something you wrote with your friends You printed it yourself at a photocopy store It's like blogs before blogs And I created a zine I was like I'm going to be a magazine publisher So the first one I did was Cyber Surfer which was about dial -up magazine dial -up services and cd -roms and i did it with my friend ryan alvey whom you might have heard of in my career we went to high school together weblogs we did weblogs together yeah so but in the early 90s i did which is and gadget twad all of that stuff yeah everything you sold aOL i think i sold a well but anyway before that i did this mag i did that magazine and then i had met fred i met jerry colonna at internet world the first one and he there was a booth.

[164] That's right.

[165] When Jerry was a VC before he was like the whisper of startup coaches.

[166] He was consulting for Likos and I think CMGI.

[167] And so there was a Lycos booth and I had met this young lady at it and we hit it off and we're talking and then she interested me to Jerry Colonna.

[168] And then I met Jerry Colonna in an office no bigger than this room in Union Square and he said, listen, I'm leaving Lycos but I'm going to start this hack me ventures with my friend Fred.

[169] I want you to come read business plans for us.

[170] And so I met Fred Wilson and I would go up to they were doing, J .P. Morgan was going to back them for their venture firms.

[171] This was 1994 -95.

[172] This became flat iron.

[173] It became flat iron.

[174] J .P. Morgan was the first big anchor of flat iron.

[175] They were half of it.

[176] And Masayoshi -San, SoftBank, was the other half.

[177] No way.

[178] So they wanted you to come, like, be a VC associate.

[179] Not a VC, just to read business plans.

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

[181] Wait, what do VCs associates do besides just read business plans?

[182] Exactly.

[183] Well, anyway, it was thing.

[184] And so I had the magazine started Silicon Island Reporter, and they were paying me. And so I read about this Beverly Hills internet company which got rebranded as Geo Cities and I wrote a little coverage of it and I said you should invest I'm 24 years old I don't even know what VC is that's where Flatiron made all their money Yeah they were gonna invest anyway The Flatiron became USV right Yeah square ventures Flatiron went with Jerry Colonna then when Jerry decided he wanted to move to Colorado and just chill Yeah he had made enough money I think And coach founders Coach founders I think Yeah maybe he had I think he's been pretty public about it like I don't want to say a nervous breakdown but a kind of like maybe a fork in the road like making a decision about what you want in your life kind of situation you know that great book about it yeah yeah and so jerry was a good mentor but fred actually became ultimately my my deep mentor at that time and uh fred said to me listen you're doing silicon eye reporter you're writing about us and the companies were investing in and um you're doing stuff which would you rather do and i think i'll do the magazine uh this was before now it's like i do both And now it's like I do both.

[185] Why choose?

[186] But just to back up to Tio Cities, that sold Yahoo for like $3 billion.

[187] And Flatiron was the main investor.

[188] Yeah, Flatiron maybe owned 5 or 10 % of it.

[189] It was like a huge win for them.

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

[191] They did pretty well.

[192] How did that happen, right?

[193] I mean, Silicon Valley was here, but they were in New York.

[194] Like, what was going on?

[195] Yeah, there was a lot of good companies brewing in New York.

[196] And my concept with Silicon Valley Reporter was, well, they have red herring.

[197] In the Bay area.

[198] Upside in the Bay.

[199] But I owned New York.

[200] And I had Silicon Island Reporter.

[201] And I started one called Digital Coast Reporter in L .A. So I had two magazines, two conferences, two email newsletters.

[202] That's kind of king of New York, right?

[203] I grew that business to $10 million in revenue off my credit cards.

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

[205] And I didn't know anything about how to run a magazine, how to run Ann Cells.

[206] I taught myself everything.

[207] What did your family think of this?

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

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

[210] It was like a finite set, and I was in publishing, but I was also in this new thing technology.

[211] And so everybody wanted in on that.

[212] It would be like the equivalent of crypto is today, like at its peak where like, and you were the equivalent of like Satoshi or something.

[213] Like it was crazy to be the New York Internet guy.

[214] Can I?

[215] So we talked about a lot of this when we did our like big Jason Cali, the Empire of Jason Calacanus episode with you.

[216] So I want to like put this on pause.

[217] So yeah, people can go listen to that.

[218] You should.

[219] It's great.

[220] We get like the detailed story of like weblogs ink and all that great stuff.

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

[222] Sure.

[223] Because the last time we talked to you, you were just starting all in.

[224] It's hilarious.

[225] And like, can we talk podcasting?

[226] Of course.

[227] I love it.

[228] Podcasting is like, I think, perhaps, my greatest medium.

[229] What happened with All In?

[230] How did...

[231] I mean, it's weird.

[232] Has it surpassed your wildest expectations?

[233] I thought it would be something Chimoth and I would do ten times.

[234] Yeah.

[235] So the origin story is pretty simple.

[236] Chimoth, I knew because he was running ICQ.

[237] Chimoth was running ICQ at AOL, and I had sold my company AOL, and I had sold my company AOL, And, like, the revolving door of AOL, it was like, Ted Leones just had this march to a billion.

[238] My Greek brother, a mentor, had this like March to a billion offsite.

[239] And so I went to this and I just sold Weblogs AOL users.

[240] Hot shit.

[241] That's the implication.

[242] That was that, well, with Weblogs, Inc. And with AOL and other assets they wanted to buy, they were going to march to a billion users.

[243] It was like this crazy rallying car.

[244] And we had these T -shirts, March to a billion.

[245] So I go to that and I see church.

[246] him off and I was like hey and he's like hey and we introduced each other and we had known of each other and so what are you doing here he's like I'm running ICQ into the ground you know I'm just riding it down every month that loses a million members whenever I said it's hilarious and he's like yeah but I'm leaving I'm gonna go um I'm gonna go to go to the West Coast I'm gonna go work at this VC or whatever I was all right nice seeing you um and so then when he was there I was in L .A and what VC did he go work because he was at Facebook Mayfield Mayfield for a year and then Sean Parker introduced him to Zuck And Zuck needed You know Like a Chimov He needed like somebody who would just Chimoth He built the growth He built the growth team And he was like I don't There is no equivalent of growth That was the idea of growth hacking Didn't exist as a term Until Chimov did what he did He said just find me the smartest people I'm hiring based on IQ And I'm hiring based on desire To make a lot of money and be a beast And he just went into beast mode Because you know he too was very hungry But you guys must have been like brothers from another mother.

[247] Yeah, for sure, for sure.

[248] We're definitely, you know, both outsiders in Silicon Valley.

[249] And, you know, I had Chimov come on the pod, this weekend startups, that is.

[250] We listened to it.

[251] It's fun to go back to that moment.

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

[253] He's not chimoth, you know, as gregarious or whatever.

[254] He doesn't have the loro on.

[255] No, loropian.

[256] Was he in great shape or?

[257] No. Not one of the teacher.

[258] He was like a dork, you know, like he, but he was...

[259] His Bezos pre - Yeah, it was like Bezos pre, yeah, whatever.

[260] You know, he always was a poker player.

[261] He was played in Atlantic City, so he was, you know, like myself, an outsider who wanted to take risk and wanted to win.

[262] And, you know, confident, you know, even maybe more confident than both of us should be.

[263] But, and so I kind of introduced Chamoth to the world by, you know, by, you know, convincing him to come on the pod, which he was, like, reluctant to do when he was at Facebook, but he did it after Facebook.

[264] So I kept asking him to come.

[265] He finally was in LA.

[266] He came on the pod.

[267] And then people, I was like, he's really good on stage.

[268] Like, he's funny, whatever.

[269] And so which at this point you had an eye for.

[270] Because you're like, of course.

[271] I mean, one of the things when I was a podcaster in those early days, you know, I'm talking about 12 years ago, whatever, is, you know, I introduced a lot of things to the world.

[272] I think like 14, right?

[273] Fourteen.

[274] I introduced people to the world.

[275] Yeah.

[276] Yeah, it was 2008, I guess, whatever.

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

[278] And then as now, too, like, you could be a great founder.

[279] You could be a great, you know, person in tech.

[280] But, like, that doesn't automatically make you a compelling podcast as we know.

[281] No, of course not.

[282] No, I mean, I have my own theories about what makes for a great guess.

[283] We'll put that on the side for now.

[284] But anyway, we start a friendship.

[285] We start playing cards together.

[286] We start hanging out, you know, trading notes kind of thing.

[287] And he's going to start his venture firm.

[288] I'm a scout at Sequoil, all that stuff.

[289] start playing and trading notes and we just become great friends but then he was coming out of cnbc one day and he's like oh my god you know just like we have such a good rapport when you interview me because he had done a bunch of interviews with me on stage and stuff like that on my events he's like i want to do a podcast with you i was like yeah you can come on this week anytime it's twice a week now and which it's now five times a week six six like sunday yeah plus i'm gonna go i may go back down to five next year it's a little much right now yeah dude you're i mean we'll come back to this but you're killing yourself right now and you're on act three.

[290] Yeah.

[291] I have more energy now than, I may have, I, just this, like, coming out of the pandemic might have as much energy as I did when I was in my 20s, but for different reasons, different type of energy.

[292] Anyway, Chimov calls me, you know, coming out of the studio, I don't know if he was in New York or he was in the one market one in San Francisco here, but he said, I want to just pot with you.

[293] I said, okay.

[294] And he said, I want to do a new pod with you.

[295] Just me and you, we talk.

[296] I was like, sure.

[297] He's like, what should be?

[298] call it with texting back and point i was like we should call it all in yeah it's like two years ago whatever and i said yeah we should call it all in like we should come with a poker name he's like yeah great like a raise or something i was like all in because you would you'd been referring to this poker game on air on twice yeah i would talk about it once in a while the poker game that doesn't exist and sky dayton and i had a poker game with brook hammerling the famous PR person at the code conference which was the all things d conference before that for 20 years then chumath had a poker game sacks i had hosted it floating and putting all that together.

[299] Yeah, I'd refer to it many times in the pod, but try to keep it from becoming public.

[300] But OSB, Bill Gurley, it's all public now.

[301] Mark Pinkus, right?

[302] Pinkus used to come to the code one.

[303] It was another funny story.

[304] And lots of funny stories in my life.

[305] But anyway, so then the pandemic happens, and we're like, well.

[306] Where are you going, just dropping these little red curls here?

[307] We've got to pick them up on the one.

[308] At some point, we've got to pick these up.

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

[310] Anyway, nine years, third book.

[311] Anyway, the, um, then we, we were, the pandemic starts to happen like, well, Sacks has some ideas about masks and then Freedberg, right?

[312] Sax and Friedberg weren't, there was no besties originally, right?

[313] No, no. And I mean, in truth, like, uh, Freeberg and I weren't besties before all in.

[314] I mean, we knew each other.

[315] We were friends, but not besties.

[316] I was besties with Sacks and Chimoth and now Freeberg is a bestie.

[317] And, but he played in the game, obviously, and we had just started to have a developer friendship.

[318] But anyway, that forcum kind of clicked, right, pretty quickly.

[319] And I think, you know, I was a really good interviewer.

[320] I studied interview techniques and really, you know, after doing whatever, I'd done at least a thousand episodes of Twist at that point.

[321] And I had had sacks on many times and Chamath.

[322] So I was very comfortable with that.

[323] And at the poker game, we break chops and I make jokes.

[324] and Chimaut's a great host and just very comfortable with each other and Freiburg kind of joined that group and it clicked and I think during the pandemic and I thought maybe this last 10, 20 episodes but during the pandemic I think people wanted information and I realized in perspective I mean I think that's a thing I'll tell you I never expected to be listening to David Sacks talk coming from from where he comes from politically and where I come from politically and going, yeah, that is a good point.

[325] And that perspective is so helpful in our polarized world today.

[326] Yeah, it's very unique.

[327] And around the poker table, we all listen to each other and we're friends, but the world does not want us to be friends in some ways.

[328] The world wants us to be enemies.

[329] And I kind of think about it like best of enemies kind of situation.

[330] Like we debate specific things, like Gore Vidal and who is his advert.

[331] Anyway, it's a great documentary about Gorvadol and William F. Buckley.

[332] They're just two public intellectuals.

[333] One was on the left, one was on the right.

[334] And there's this documentary, Best of Enemies.

[335] In the 60s, they started debating, like, different political conventions.

[336] It was, like, the most compelling thing on TV.

[337] But they were, like, Friends.

[338] Best of enemies.

[339] Best of enemies.

[340] They weren't besties, like Saxon, I are.

[341] But, you know, Gorvadol was just, he was gay, kind of closeted or quietly gay.

[342] and on the left and Buckley was like a serious conservative and they went to blow sometimes on the show like at one point Buckley I think he called him like a sissy or something like really like derogatory as a gay man and the world didn't understand he was exactly gay it was like sort of time period in the 60s where like maybe some adults understood like yeah that's a gay man but we don't say that's a gay man. When they got into town yesterday we were driving the castos right nearby and we saw a naked guy in the castor and I was like oh a naked guy in the cat And Ben was like, what is going to, like, dude, you got to understand in the castros.

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

[344] So he's like just all like slick down sweat.

[345] But did he have shoes on?

[346] Was he wearing combat boots?

[347] They usually wear boots.

[348] And then they usually carry a sarong.

[349] There was a big debate when I first moved up here because there was a number of folks who used to like to get a Starbucks.

[350] And they had to like negotiate.

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

[352] Because you're going to sit.

[353] Right.

[354] And for context, you know, I've explained this to Ben, but like, this is a thing in the Castro in San Francisco, it's a cult, it's like a, now it's like you see it's like, ah, this is like a relic of the 60s, 70s in San Francisco.

[355] Yeah, it actually was pretty awesome because David were like driving up and David goes, oh, a naked guy.

[356] It was the most like warm hearty.

[357] Yeah.

[358] I had to, um, yeah, adjust as well as a New Yorker because as a New Yorker, if somebody's naked, that's a sign that if there's about to be some crazy person in a fight and police and chaos.

[359] And here, it means, like, high fives and right -ons.

[360] But, you know, growing up in New York, like, if somebody takes their clothes off on a public transportation or in a cafe, like, people are getting a baseball bat and calling the police and, like, the shit's about to go down.

[361] Oh, my gosh.

[362] You know, and then here it's like, you know, high -five and live your life.

[363] That's one of the things I love about San Francisco.

[364] But anyway, the pod's gotten very big.

[365] So you get the gang together and, like, why do you think it works?

[366] Like, is it that it's like the number one -ish?

[367] Well, in our business is number one, of course.

[368] But it was number 28 last week in the world on IT.

[369] You guys have transcended.

[370] Like, this is more than just...

[371] It has nothing to do with tech anymore.

[372] It has nothing to do with finance or tech anymore.

[373] It is tipped over into colleges.

[374] I was at, you know, skiing in Tahoe.

[375] And I was with my kids.

[376] And it's hard to get a table type situation.

[377] I was like, hey, I hate to be a pest, but I see you're wrapping up.

[378] And no pressure, but are you going to be leaving soon?

[379] Because I'd love to camp out here and get your table.

[380] And they're like, stop busting.

[381] my balls chasing.

[382] And the woman looked at me and she goes, Jake Hal?

[383] And I was like, have we met?

[384] And she's like, no, I listen to your pod twice a week.

[385] I'm like, it's only on one.

[386] She's like, I listen to it twice.

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

[388] She's like, I was like, are you in the industry?

[389] She's like, I'm a dentist.

[390] Reno.

[391] And I'm like, you're a dentist in Reno's.

[392] Can I ask how you found out about?

[393] She's like, I don't know.

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

[395] No. It's not how she had found it.

[396] And this is, you know, during the pandemic situation.

[397] And then that's when I realized it had crossed over.

[398] Was there a moment for you, either euphoria or, or you, where you were like, whoa, this is...

[399] You know, I've been micro -famous, you know, micro -celebrity multiple times in my career.

[400] But this is different.

[401] Yeah, not for me, you know.

[402] And I got a lot of famous friends.

[403] You know, I'm used to getting recognized.

[404] I'm used to people taking pictures.

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

[406] now it's 20 you know or 10 and they want to take a selfie and it's you know just you're not podcasting is you guys get recognized and it creates a level of intimacy with people for sure if they're in the habit yes because you're hearing people every week and then people become characters and I try to make everybody I was you know in in a lot of show or in all honesty I did craft with all in I was very premeditated and creating some character I've never really talked about Yeah, yeah, yeah.

[407] But I crafted some character kind of arcs.

[408] The fights are all real.

[409] Trust me. There's nothing scripted about that.

[410] But I did say, like, I think I can, as the point guard here, kind of shape the conversation.

[411] And I literally created the character of the Sultan of Science.

[412] Right, as I was going to say.

[413] And, you know, Freeberg didn't even have a Twitter handle, zero followers.

[414] There's even a character of J -Cal on All In.

[415] Like there's the world's greatest moderator, sure.

[416] I think more like J -Cal, the guy who lets himself be the punching bag, because it plays for the show.

[417] A little bit.

[418] I would rather, if I'm being honest, I'd rather not be the punching bag.

[419] They're like, you're the poorest guy on the show.

[420] I'm like, do we need to point that out so often, guys?

[421] You're like, not by much.

[422] Like, I'm feeling really good about myself.

[423] You don't have to point out that you all have more money than me, and you two of you have planes and I don't.

[424] And it's okay with me. I could have a plane, I guess.

[425] I could get one, but.

[426] You care about the environment?

[427] well no it's also like i don't want to waste a ton of money and you know whatever reason but you do you do let yourself play that role of like like you have been enormously successful and you sort of let the role of j cal on the show be like that guy who one day wants to be like us maybe he'll maybe he'll make it i actually never wanted to play that actually no that was not that was just the boys breaking my chops maybe so maybe it's a little bit of like them wanting to uh you know maybe uh maybe uh Take the piss out of me a little bit, which is fine, because, you know, I give it as good as I can get it.

[428] But I think that's probably for them, you can ask them when they're on the pod.

[429] I think for them, that's kind of the dis, that's the one they can easily go to, as I'm the poorest guy on the show.

[430] But like, I've done okay.

[431] Maybe let's flip it.

[432] Like for them, before all in, I mean, Tamath had a little bit of a public business.

[433] No, they were not famous.

[434] They had no go to market.

[435] They're all, this is a new thing for each of them to hit this level of notary.

[436] It's not for me. What do you think for, I mean, we should ask them this.

[437] Sure.

[438] Like, if you were to speculate, caveat that it's speculation.

[439] What do you think for them all in has like done?

[440] Well, I mean, for Friedberg, nobody knew who he was except if you worked at Google or you were in VC.

[441] Like he's very connected in those circles.

[442] What's that?

[443] Or Monsanto.

[444] Or Monsanto.

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

[446] I think really by design he didn't have any desire to so I think it's probably the biggest adjustment for him the increase in profile has certainly been the highest for him and he's loved there was a moment when I like jokingly said to people during the Q &A session at Olin Summit you know just say who your favorite best he is and then direct question and it was like five in a row Sultan of Science and it was like oh my god what have I done now I've created this monster you know at the time like would barely show up for like he would show up for two out of three episodes he'd be busy.

[447] It wasn't a priority for him.

[448] Right.

[449] So I'd be like, all right, I'll put Brad Kersner in.

[450] If you can't make it, I'll try to get Bill Gurley to show up or whoever Draymond to fill in for him.

[451] You know, and it was always like, I wonder if Freyberg will show up, but he's actually really committed to the show now.

[452] For Sacks, he was high profile, but nobody really knew him as a Republican.

[453] So he kind of uncloked as a Republican on the show.

[454] Well, I feel like he was also like, he was almost even more so than any, you know, well, not you, but he was high profile if you knew about the PayPal Mafia money, but he was like the least kind of public of the PayPal Mafia.

[455] Of the PayPal Mafia, you would say Elon, Reid, Hoffman, Peter T .L., Max Levchin, Jeremy Stoppelman, Chad Hurley, Ruloff.

[456] Yeah.

[457] And I guess Sacks would be somewhere in that strata of like being known.

[458] But I feel like to be known.

[459] Being known.

[460] Yeah.

[461] Being known.

[462] But yeah, you know, I think part of the reason this works is Sacks, I think Sacks has probably taken the brunt of the head of the pod.

[463] Yeah.

[464] Because he is so passionate about, you know, a lot of topics that maybe are unpopular in the tech circles.

[465] So I do think, like, it's cost him deal flow on the margins, probably.

[466] I think there's probably, you know.

[467] I don't, really margin, like, I wonder.

[468] On balance, he said that jokingly on the show.

[469] I don't know.

[470] I'm just thinking, like, maybe there's somebody.

[471] Craft has ascended because he's done all in.

[472] I guess.

[473] Yeah, sure.

[474] I'm trying to think if, like, would.

[475] Is there a founder, I wonder, I don't know this, but is there a founder who's a young founder who would say, I would never take money from Peter Chil's venture firm?

[476] Because I'm so liberal.

[477] For sure there are.

[478] And those people feel that way about craft now.

[479] But for every one of those, there's 10 more who know about crafts now.

[480] I kind of agree with your position.

[481] Yeah, I would agree with that.

[482] So anyway, I do think, like, he's joked that it's cost him deal flow.

[483] I don't know if it has.

[484] I think truly the benefit.

[485] The pod, too, I think for people in America and people in tech, has moved, I think, a lot of people towards the center.

[486] I think a lot of people were moving towards the center and we codified it for people.

[487] We maybe made it okay to admit you're a moderate.

[488] Yeah.

[489] You know, I've been telling folks from the beginning, I'm an independent and a moderate.

[490] I voted probably Democratic three out of five times, four to five times.

[491] But mostly that's a function of the fact that I've lived only in New York and California in my life where you don't really get many Republicans or moderates.

[492] But I voted for Bloomberg, Giuliani, when it was crazy.

[493] And Pataki, who were all Republicans.

[494] It's insane to me. Were you here doing the sports Liger era?

[495] Or were you still in New York?

[496] No, I wasn't.

[497] But I would have voted for him.

[498] I like competent people.

[499] And I supported Bloomberg for president, which got me a lot of flak.

[500] Really?

[501] I don't understand why.

[502] People were very upset that I was for him instead of whoever.

[503] I think you guys talked about this on the pod that like, oh, what was the two by two quadrant of like, whatever it was?

[504] We all think we are here in Silicon Valley, which is like social, liberal, fiscal.

[505] conservative yeah we're like everybody should be that but we're the smallest of the four groups yes it is a small group i i um i think i believe in competence and staying out of people's lives so i you know it's very hard to know because and then even david i mean this is i think when david and i fight on the pod which some people love and i think some people probably turn the pot off when that happens and they don't like it um and certainly i the maga group is has no love loss for J -Gal.

[506] I'll tell you that.

[507] Like, my replies have been really crazy.

[508] I would get, like, brigaded the last couple weeks.

[509] It's nuts.

[510] It's funny, but it's also, like, on the margins.

[511] Like, they can get a little scary.

[512] Like, they'll docks me sometimes.

[513] And, you know, that's not fun.

[514] A handful of times has happened.

[515] But, you know, I had to tell David, like, David, I am not, like, I don't actually listen to MSNBC and Rachel Maddo to get my information.

[516] and by the way your pro -choice pro -gay marriage anti -war yeah he's the dove and I was like well okay if you if we want to play this game I'm gonna dub you David the dove and now you're making me into Jason the hawk like what are we talking about here like but anyway you know what just goes to show how silly the coalition building is like it's totally silly exactly the two -party system requires that if you feel very strongly about something then you're not allowed to think independently about anything else.

[517] It's so crazy.

[518] And I think what messes people up is the fact that I actually just think Donald Trump is a horrible human who you should do no business with, has no business being in any political office, and, you know, it is just horrible on any number of levels.

[519] But I believe that independent of his party, he's a Democrat, obviously.

[520] Obviously, yeah.

[521] And so, like, I would hate him as a Democrat or a Republican.

[522] So it's not personal, and I would love to.

[523] Or it is personal with him, but it's not.

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

[525] Now, I understand for some people, he represents change for some people.

[526] It's like the way the Republicans secure at office and that's all they care about is winning.

[527] I get it, whatever.

[528] And I think so much of the human condition is like being a part of a community.

[529] And he, for so many people, is a symbol that means, hey, all my friends and neighbors, we get to agree on something so that we all can find.

[530] togetherness in something and for some people that's the flat earth and for other people that's startups and for some people it's the tribe yeah we don't you know a lot of people don't practice religion anymore and so he's their religion and Hillary Clinton or Elizabeth Warren or Bernie Sanders might be other religions or the new iPhone like I found myself ordering this phone and I love it and it's the I414 Pro and it's magic and whatever but like it's not that different than my old phone but I got to participate in all the fun watching of the keynote and the tweeting and the nerding out.

[531] I'm like, let me look at the image quality versus the old one.

[532] I got to say it really is pretty.

[533] It is pretty.

[534] But like I got to be part of a tribe.

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

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

[537] When I say we, including you guys, but also specifically the besties, I want to be friends with people who I disagree with.

[538] I want to debate stuff, right?

[539] And then people are like this guy Dean Preston in, he's like one of these supervisors here.

[540] He's like super idiot, like guy in San Francisco who like won't let them build housing and stuff.

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

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

[543] He's like, you're a conservative billionaire.

[544] I'm like, wrong on both accounts.

[545] But thank you for the latter.

[546] My besties remind me on the ladder.

[547] Yeah, I'm working on it.

[548] Not trying to be a billionaire.

[549] Thank you.

[550] And on that, another thing that's really fascinating to me about All In and you guys is before All In, and maybe it's still to a large extent, I feel like Silicon Valley has this weird relationship with money.

[551] Like super weird relationship with money.

[552] Like, you know, remember there's a whole thing about, like, Zuck drove, like, an Accura SUV.

[553] That all came from David Philo and, um, David Philo and Jerry Yang were driving their old cars to work.

[554] Right.

[555] Like, the cool thing, like, you could, like, make money, build a company, but, like, you never want to, like, you never, and.

[556] Be understated.

[557] You guys, I think, are the first, like, like, you're, you guys, like, whatever.

[558] Like, we got a private jet.

[559] Like, that's fine.

[560] Like, you know.

[561] I mean, listen, I, I, uh, you know, I believe in capitalism.

[562] I think it's great if people create jobs and if they get rewards for doing so, like, fine.

[563] Literally the book I'm right, my second book right now I'm writing is about wealth and money.

[564] And like, but not like in my regard, but in a sort of like big picture of societal regard.

[565] So I'm like literally been thinking about this topic a ton.

[566] And I think we worry a little bit too much about wealth creation with like a small like outlier wealth creation.

[567] and we don't think enough about inspiring people to create companies and learn.

[568] And the time I create the most controversies when I'm like, I believe anybody can do it.

[569] And people are like, you're so wrong.

[570] And I'm like, am I?

[571] Because I go on YouTube and you could type in any topic that you want to learn and you can learn it.

[572] And all the stuff that was at MIT where I never got to go in Stanford and Brown is online for free.

[573] And I listen to macroeconomic classes and AI classes.

[574] When I'm like, it's 10 o 'clock at night and I'm doing my email, I'll just put one of those playlists on from MIT OpenCourseware.

[575] And I'm like, I can't believe I can take a course at MIT for free anytime I want.

[576] And then you, you know, flip it, you can build a business there.

[577] Like David Senra over the Founders podcast, like Mr. Beast, MKBHD.

[578] Like, nobody gave these guys permission.

[579] Yeah.

[580] But people want to.

[581] spread a narrative that the world is unfair and like I watched oh I think the world becomes so fair and so just and so much information opportunity become available that I'm like wait a second we I could never figure out how a term sheet worked and nobody would share their term sheet and now there are a thousand videos and blog posts on how to negotiate your term sheet the world is still unfair I think I very I think the key insight is like recognize that the world is unfair and actually what that is is a game on the field and figure out how to play the game on the field but I mean it's never been more fair so the world is unfair true statement and in America it's never been more fair you can learn Google has like five courses online I think it's called Grow with Google or something where they're teaching how to be a ux designer how to do this how to do that and it's free so that they can get more people to apply for jobs And the average job, entry salary for these things is like 80K.

[582] So I find that it's very weird in the world.

[583] I think there's like a group of people who want the world to be more unfair than it actually is because it makes them feel more virtual signaling goodness.

[584] Well, that's their community.

[585] That's how they find that there are other people who love that they tweet that the world is unfair.

[586] And they have to, and it typically like is a certain type of person.

[587] I'll just leave it at that.

[588] Okay, can I, so I'm going to leave about your question.

[589] I can teach Founder University now.

[590] I have a course where I teach people for 12 weeks, or I should say have a team that teaches it.

[591] And I'm going to actually teach it myself, this next cohort, where I just teach people how I start companies.

[592] All right, let's plug it.

[593] How can they find out?

[594] Founder .d. University, that's it.

[595] There you go.

[596] Yeah.

[597] I mean, it's basically it's free.

[598] The way I did it was you apply.

[599] If you want to build a company, you pay 700 bucks.

[600] If you go and you get to Week 12, we charge your strike back, the card back, the $700.

[601] If you don't come, or if you don't have an excused absence, if people, miss something because of their kids or whatever fine but we just try to get people to complete it over 90 % people complete it that's cool so and then we're investing 25k and some of those folks to help them start their companies like people don't know all the work i'm doing like quietly but like 200 people go to this course now maybe i'll have 400 in the next code the fourth cohort we'll see but you know like people can learn how to create companies and they're like no they can't and i'm like yes they can you have to have gone to stanford i'm like no i'm invested in 350 companies like maybe percent of the founders went to Stanford like no that's just not it's patently false like you know you have some confirmation bias you're dealing with a data set from 10 20 years ago I get it but I'm telling you like on the streets ground level truth we all meet with founders all day it's never been more diverse it's never been more open nobody cares where you went to school nobody cares where you live anymore nobody cares where you live they care about what you've built and your traction like it is post -pandemic all people care about it's like like show me your metrics, show me the product, show me your team, what are your skills?

[602] Great, let's go.

[603] What's your growth rate?

[604] It's basically become like as beautiful of a meritocracy as I've ever seen.

[605] You say the M word, it freaks people the fuck out.

[606] I'm like, why is this so scary for you that Silicon Valley is a meritocracy?

[607] And they're like, because it's not.

[608] And I'm like, it kind of is.

[609] Can I answer your question earlier of why I think all in works?

[610] Yes.

[611] All right.

[612] Go ahead.

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

[614] things.

[615] The first thing is...

[616] A lot of there is out there, by the way.

[617] Billioner porn.

[618] Most people, you're counter positioned.

[619] Most people who attain that level of wealth crawl into a quiet hole and make sure no one knows about the pride of jets.

[620] You're doing shows from boats and jets.

[621] Yeah.

[622] So there's like...

[623] I don't think we've done it from a jet, but yeah, there was definitely two boats in the last two years.

[624] That's true.

[625] Not my boat.

[626] In some peak moments of all in, it's like watching billions in real life.

[627] It's like you hear, you hear Chama.

[628] talk about this spread trade and you're like this guy's got a lot of money on that spread trade and like does he actually have a key insight here or is he like there's there's this interesting intrigue there so bucket one is like billionaire porn bucket two is uh by the research you guys do and and the folks that you each work with because there's definitely researchers that seem to be involved you bring things to the table there like brand new insights that aren't widely available yet so i feel like i was learning things about COVID -19 on All In that I wasn't getting through any other source.

[629] I'm like somehow this is not making it to me and this feels very like a lot of it proved out to be like this was good information before it was mass. All four of us are information junkies with a lot of research and teams that could inform us.

[630] How many people all in how many people touch an episode of All In?

[631] One producer Nick.

[632] No, I mean but like the research, I don't know I'm pretty sure.

[633] files open on people's computers when they're talking?

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

[635] Like I just read the four or five bullet points so people know it.

[636] So I do that with my team, the docket.

[637] But the docket is built from, you know, the five or six stories that people submit to our group chat and say, hey, put this on the docket.

[638] Right.

[639] And I think Sacks has some research help.

[640] I'm sure Friedberg and Chimov read the stories or they're well read.

[641] I mean, all of us read constantly.

[642] and we're in the information business of talking to people about the world.

[643] So you guys are investors.

[644] You know how it is.

[645] Like you do 20 meetings a week with founders.

[646] They're going to tell you everything about the world.

[647] Yeah.

[648] And you guys are young still, but imagine you do that for 20 years.

[649] Like you're going to get smart or you're a journalist for 20 years.

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

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

[652] Definitely.

[653] So, okay, that's number two.

[654] Yeah, we probably have a slight information edge.

[655] Yeah.

[656] Certainly a huge, I will say the information edge compared to journalists, having been, this is not a dig to my journalist friends, I was a journalist, I had 75 people at the magazine, we were always trying to figure out from the principles what was going on and tell that story.

[657] But we were only as good as our access to information, and we probably, I, now looking back on it, I think we had between 5 and 35 % of a story.

[658] And I know that's like probably triggering to a lot of journalists that they have that little.

[659] information?

[660] You weren't on the inside.

[661] But you weren't on the inside.

[662] So when you're in the inside, you have 100%, or even on the inside you might only have 50 % depending.

[663] You get enough to run with and you feel like, okay, now there's enough story here, let's do it.

[664] And like, that's clearly not the whole story, but it's enough to put the piece together.

[665] And then over time, process journalism, as some people have dubbed it, you know, maybe the six or seven stories will tell the full story.

[666] Yep.

[667] Yeah.

[668] Which a third component.

[669] You think makes it successful.

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

[671] Yes.

[672] Like people like having fun by listening to stuff.

[673] Sure.

[674] And so, like, if we can make history fun, then people are going to listen to four hours of us diving into stuff.

[675] You would never read in a book.

[676] And you guys do that in spades.

[677] Like, it's just so fun to like temporarily join your world.

[678] I mean, the fact that you as a podcaster who makes elite, content like top 1 % content find it compelling is just yeah that's very yeah listen every week don't miss it i can't literally walking the baby up and down the hills listening i mean i have people tell me they listen to it twice they take notes i'm like wow that's great you know i i don't take note maybe i should take notes well anyway i was very intentional with my role in it to step back uh and be like the point guard um but you know i'm a shooting guard too so sometimes i will want to shoot the ball, and I can do both.

[679] I'm a combo guard.

[680] How did the Freiburg host episode come about?

[681] So one week, you switched roles.

[682] Well, he was like, I think this could be done better, this could be better, and I was like, go ahead.

[683] And I just like, sure, I'll just shoot.

[684] You pass the rock and I'll.

[685] I was like, yeah, you want to be going to, go ahead, show us.

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

[687] It's not a point guard.

[688] It's not showtime, that's for sure.

[689] I don't think people are going to go to watch him play a point card I mean he did a serviceable job and put that on his tombstone no but he shines when I created science quarter for him to shine bring me a sign he's like oh you know I don't know if I want to talk about politics I was like listen Sax wants to talk about carnivist politics I'm giving him his red meat here's your kinwa come to me with the science story you know and we'll do this Kinwa corner kind of thing and I made him the Sultan of Science and so good you know it was it was a distinct effort.

[690] I really wanted to make him shine, you know, and it worked.

[691] You know, it worked because you see how engaged he is.

[692] And what used to happen was, and fans know this.

[693] I'm not speaking at a school here.

[694] You see it every episode.

[695] Sacks would disengage during science and Kinawa would disengage during politics.

[696] And what I've been trying to do is keep both of them involved when the other is doing stuff and Chimoth and I are involved.

[697] That's a hard job.

[698] That's a delicate.

[699] I studied the McLaughlin group.

[700] People don't know this, but I went back to look at McLaughlin, and I watched him moderate.

[701] So people, there's a big debate.

[702] Do I interrupt too much or not enough?

[703] Do my interruptions?

[704] I call them interjections.

[705] Do they help?

[706] And I actually looked at the interjections.

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

[708] So the McLaughlin group was like the best Sunday morning show.

[709] And like it was so good like S &L with parody, McLaughlin.

[710] it probably had a million people watching it but this guy McLaughlin was like pretty cantankerous and if he didn't like what people would say he'd be like wrong this is the answer you know like and it became so competitive that you wanted to watch it now what I didn't realize by adopting that would be that Sacks is the ultimate debater and will fight like a dog until he wins any debate and so I may have pushed Sacks into more of a debate situation where I'm trying to not have it be a debate.

[711] I'm trying to have it be a conversation.

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

[713] And then some people in the audience are like, you have to be the fact checker for sacks.

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

[715] I'm not real -time fact -checking sacks.

[716] And so that is a delicate balance of like, and then sometimes I'll ask questions, specifically because I know the audience doesn't know what, you know, fair market value when they hear an acronym means.

[717] So I'm like, explain that.

[718] And I'll stop somebody.

[719] Now, I mean, you're expanding the tim to dentists.

[720] Correct.

[721] Thank you.

[722] So people are like, oh, Jay Cowell's an idiot.

[723] He doesn't know that turn.

[724] Or I say to somebody, can you unpack that?

[725] Can you explain that?

[726] Obviously, you know that term.

[727] You were with a third or fourth investor in Uber?

[728] Yeah, like, exactly.

[729] Well played.

[730] I think he's been in Robin Hood, too.

[731] Oh, come too?

[732] Wow, who knows?

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

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

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

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

[737] They don't know what the spread trade is.

[738] Let me pause.

[739] Can you explain one more time or let me reflect back to you.

[740] Is this what a spread trade is?

[741] And he's like, almost.

[742] And that's what I think has brought in, to your point, a lot of the dentist crowd.

[743] And having an intimate sense of where your audience's edges are is a really important role there.

[744] Like when we have guests on, I'm always trying to catch where do they just go slightly too deep and I need to pull them up.

[745] And you know, podcasting is about going deep.

[746] So it is really an art. Like do you want to stop somebody when they're going down this like crazy rabbit hole?

[747] There's no clock in this room.

[748] Well, they're going down some rabbit hole that.

[749] has never existed in media before.

[750] Right.

[751] And you want to let them go, but you need to make sure they're taking the stairs.

[752] Because, like, if they just jump in, you're like, oh, God, no one has any context.

[753] They can't learn anything new because you're like, you're not connecting it to something they understand.

[754] They just jumped into brain surgery.

[755] Let's just explain to us what's going on here.

[756] How are we going to chop up this brain?

[757] Right.

[758] Like, yeah.

[759] It's a bit of an art. But, you know, I have to say, like, it's been a different muscle for me to flex.

[760] And it's been great fun for me. The other thing, like, I don't know if you think about it on this axes at all, but, like, I kind of think of there's, I used to think it is very binary.

[761] Like there's two categories of podcasts.

[762] There's candy and there's vegetables.

[763] And like I listen to the audio version of Straterey and that's my vegetables and it's not like deeply, it's enjoyable intellectually, but it's not like fun.

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

[765] I have to be like on a run and like sometimes even at home so I can take some notes or look something up I can be cleaning it's a pause type podcast you have pauses sometimes sometimes you're hit and rewind right let me make sure I'd get what he's saying here or I can listen to the talk show with John Gruber and it's just like if I missed out on 20 minutes because I was like brushing my teeth and then I left the room and I came back and I'm like oh I didn't actually miss anything because this has just been morning show it's comforting yeah it's like I love all the stuff he's talking about but like it's not must listen every time every minute every second concept and I'm not using hard parts of my brain to understand.

[766] But Al -LIN has become candied vegetables.

[767] It's both.

[768] It's both, yeah, for sure.

[769] Yeah, I try to do with this week's startups and Olin is try to have it be both.

[770] A little bit of personality, a little bit of entertainment, some fun hot takes.

[771] Right.

[772] I mean, related, but separate topic.

[773] Silicon Valley.

[774] Yeah.

[775] I feel like, especially there's a lot of, part of the origins of All -LIN, there's a lot of, like, bashing on San Francisco politics and California.

[776] Like, there's a lot of crap wrong here.

[777] Yeah.

[778] But you guys are all still here?

[779] How are you guys feeling about that?

[780] Yeah.

[781] How do you feel about that?

[782] Like what do you think of the Bay Area?

[783] You know, I lived in New York, Brooklyn and Manhattan, and then I lived in L .A., and then I lived here.

[784] And so I think my, I'm moving to places I enjoy less and less each time.

[785] Like I enjoyed Brooklyn and Manhattan much more than L .A. I enjoyed L .A. much more than San Francisco.

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

[787] Wait, so why are you still here then?

[788] Well, I can't...

[789] There's no reason for you to be here.

[790] I came up here because I had a lot of friends up here.

[791] And I had done L .A. And I was like, I wonder how far, you know, I had been a Sequoia Scout.

[792] And then I was like, my friends are telling me I could start a venture fund.

[793] You kind of need to be up there.

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

[795] And I was kind of this...

[796] Because if you wouldn't, you'd always wonder.

[797] Well, Michael Moritz used to call me the mouth from the South.

[798] Because they had like two investments in L .A. Oh, the mouth from the South is here.

[799] What have you had your stuff to, Jay Cow?

[800] Sir Michael saying that.

[801] But I moved up here.

[802] And yes, I love it up here.

[803] It's quite bucolic.

[804] My kids are loving it.

[805] It's quite nice.

[806] I would love to live in another city in my life or two.

[807] I could see myself in Austin or Miami.

[808] I like both of those cities.

[809] I think Austin's kind of the future.

[810] I think California is going to be damaged for a decade or two.

[811] So I think for the rest of our adult lives, this town.

[812] Because of the pandemic?

[813] I think the politics and not appreciating the politics, the regulation, and not appreciating the tech industry is really the problem.

[814] And then you look at this guy, D. All right, listeners, our sponsor is one of our favorite companies, Vanta, and we have something very new from them to share.

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[819] It's kind of wow.

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[837] I'm impressed in.

[838] He is dunking on the founder of Away and Stuart Butterer, Phil from Slack.

[839] They're a couple.

[840] And he's like, we got a million two out of them when they sold their homes.

[841] And I'm like, and you also lost two incredible founders who've created billions of tens of billions of dollars of wealth for San Francisco.

[842] You idiot.

[843] And like, at the same time, Francis Suarez in Miami is listing all of the venture capital and doing a tweet storm about all the companies that raise venture capital.

[844] So you have one guy Dean Prest and dunking on people saying, we have this 1%.

[845] So when they sold their $30 million house, we were able to extract a million two, that's why tech doesn't like when I was like, hey, dummy.

[846] Yeah, now all the future earnings are gone.

[847] Now, what's California marginal tax rate is 13 .3%.

[848] I mean, but just as they have an exit tax now for homes in San Francisco.

[849] So if your home costs over 10 million, when you sell it, I mean, I think it's just a sales tax.

[850] One point two million from them selling their home versus 13 % of their future earning stream.

[851] Literally the chef at Slack made a billion to, paid a billion to in taxes.

[852] from their RSUs.

[853] Like, are you such a...

[854] A million two.

[855] Probably.

[856] Like, the million two, the chef probably paid in taxes on their RSUs at Slack.

[857] You're absolute moron.

[858] Like, you're literally so upset about their mansion and dunking...

[859] And you're dunking on an individual's name.

[860] But anyway, the fact that we hate entrepreneurs who create jobs and wealth or certain people do, It's just insane It's just insane Like what I mean you could Go change the tax code It's fine like you know Raise the minimum wage Like Bernie Sanders and Elizabeth Warren Attacking Bezos Endlessly and then Amazon starts paying $22 an hour Gives you benefits And pays for your college And it's like okay hold on a second I know what Bezos just did He took the platform that you could never actually enact And he enacted it inside of Amazon If it's not perfectly clear what just happened, literally he's dunking on you.

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

[862] He gave it to Amazon employees.

[863] You wanted a $15 minimum wage.

[864] He made it $22.

[865] And you wanted everybody to have universal health care.

[866] And he gave universal health care.

[867] Like, that is literally what Bezos did to them.

[868] How embarrassing for that.

[869] Maybe you could argue that, like, them pushing it and pushed it.

[870] No, no. Definitely.

[871] It is literally him showing, like, as the Amazon crew showing, like, let the free market.

[872] market's work.

[873] Like the DoorDash, Uber, Amazon, Starbucks, absolute race and battle to just hire entry -level employees and make it delightful for them is what has driven, you know, and a lack of immigration is what has driven these salaries up, right?

[874] And the benefits up.

[875] It's extraordinary what's happened with the free market.

[876] There's competition.

[877] The wage is still $7 .00.

[878] Federal middle wage is seven and change still, right?

[879] And 15 here in the city.

[880] And New York is 15.

[881] Like, yeah, it's weird.

[882] All right, listeners, it is time to tell you about one of our favorite things now that Jason is out of the room temporarily.

[883] For all of us who have been paying attention in this crazy space, there are now a ton of options for picking a corporate card and expense management software.

[884] So how do you cut through the noise?

[885] What's the difference between all of these companies?

[886] Well, any founder or CFO who's expanding globally and is becoming really like an enterprise -grade company will tell you most are really not up to the job.

[887] Reimbursements take forever, issuing cards internationally.

[888] Huge, huge pain.

[889] And they basically never offer currency visibility.

[890] Totally.

[891] Well, this is why, so Brex was one of the first corporate cards as most folks know.

[892] The first like new innovative.

[893] First new innovative startup, corporate card for startups.

[894] That's how they started.

[895] But now they've added on a whole spend management.

[896] platform on top of the corporate card and it makes so much sense for it to all be together like the data being integrated lets them do really great stuff to like you want your employees to be compliant so it ensures 100 % compliance but also you need it to be easy for them so you can do cool stuff like have managers set budgets and then as long as people are spending within those budgets then they're just in policy everything's always approved all the time no receipt chasing so they're C -chasing, no approvals, no, it's all just done.

[897] It's all integrated.

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

[899] Yeah, like, globally, like how many companies these days, even startups employ people globally who are not just need to be paid but then are like spending buying things going to dinners, et cetera around the world like you need something that operates globally so it's awesome the like the remote work thing is here to stay they shared the stat with us more than half of the startups in the last YC batch are from outside the US and then there was another one Accenture said that workforce models with productivity anywhere are now used by 63 % of growth companies.

[900] So remote is not going away so you really do need to figure this out for people who live everywhere despite you and i and jason being together here in person today we are remote so many of you are we know too obviously uh the last thing that we want to tell you about with brex today is related to being remote in different time zones brex now has 24 -7 enterprise class enterprise grade support which is important because if something goes really wrong with your spend In a time zone, half the world away, when everybody in HQ is asleep, you really want somebody to be on that.

[901] So Brex now 24 -7 is able to take care of everything.

[902] Yep.

[903] If you have global enterprise ambitions, Brex is the answer.

[904] And of course, they have a great mobile app.

[905] They were like one of the first corporate card programs to have a delightful mobile app.

[906] And now that they're serving large, growing customers around the world, they can do everything from that mobile app too.

[907] Indeed, indeed.

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

[909] Thanks, Brex.

[910] We referenced this at the start of our conversation.

[911] You're working as hard or harder than you ever have.

[912] You said you've got a...

[913] Smarter.

[914] A new well of energy.

[915] Yes.

[916] Tell us about it.

[917] Well, I find great purpose in what I do.

[918] And when my friend Tony Shea died, I really thought deeply about, like, what I wanted to get out of the rest of my life.

[919] And I realized, like, these are the things I really love doing.

[920] And these are things maybe not so much.

[921] And I just realized my life over the last two years.

[922] So what are the buckets?

[923] Yeah, exactly.

[924] So I can tell you the things that, just to me, I'm just not going to get any pleasure about life.

[925] working like no offense to my incredible lawyers but negotiating term sheets and legal and HR issues and accounting and operations and tax and you know that entire stack of things not fun to me not fun at all and I'm sure you never viewed that as fun but at least before you were like I'm willing to put up with it because maybe it's a thing that creates value enough for me to do it um doing my podcast every day absolute joy entertaining an audience you know thinking uh thinking about the world and having these conversations.

[926] I had Toby from Shopify on today.

[927] Like, I leave the Toby interview.

[928] It's like his third or fourth time on the pod.

[929] That's awesome.

[930] And it's just like, instead of us having dinner or lunch, we just record a pod.

[931] The end.

[932] Did you do it in person or did he?

[933] No, just popped on Zoom.

[934] You know, he just started because he did that tweet about his compensation tool where, you know, here's your total comps, use a slider.

[935] I was like, that's brilliant.

[936] Come on the show.

[937] You want to come on the show and talk about?

[938] I was like, yeah, of course.

[939] And so like those conversations, I just looked at them and I'm like, my energy coming out of the show is on 11.

[940] Why am I not doing this every day?

[941] And I watched Howard Stern when I was a kid or Charlie Rose do it day in and day out.

[942] And I was like, I could be like those guys.

[943] They every day get on there and they seem to love it.

[944] And I do.

[945] And so I just committed to doing it every day.

[946] And I love it.

[947] Isn't it weird when there's something that takes a ton of work but somehow it doesn't drain?

[948] you?

[949] Not at all.

[950] To me, it's like going to the gym.

[951] It's like working out or having dinner.

[952] It's just something I do every day.

[953] That gives me great joy.

[954] And then that's, I recruited Molly.

[955] I was like, I need somebody to do this with me every day.

[956] Oh, yeah.

[957] Who I respect and who's awesome and bring something to table that I don't have.

[958] And having she's so great.

[959] Having someone to play off of, like, I feel like that's the thing that's kept acquired going.

[960] Yeah.

[961] Is that like you and I can like, I don't know how you did it alone for.

[962] I don't know.

[963] I'd have guests on.

[964] It was largely a guest -driven show.

[965] And then I would do the news roundtable once a week because it was once a week, then twice a week, then three times a week.

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

[967] And I enjoy meeting with founders when they fit a certain profile.

[968] But it's very hard to meet with a large number of founders, given how many are coming in.

[969] And it's hard to work with them when they're just talkers.

[970] Yeah.

[971] To me, that's a very hard part of the job, because it becomes very repetitive.

[972] So how have you excised that?

[973] Well, I created a platform founder.

[974] university where if you want to build something, I will talk myself to 200 people, you can build, and then whatever rises, as the performance and the product, you know, and as people move from talkers to the walkers to from, you know, when they actually start building stuff, that's when I get great joy.

[975] And so I'm like, bring me the people who have product velocity.

[976] So I told my team, listen, you're doing my team does six, people don't understand the scale of the business.

[977] I have.

[978] Nobody's really understands what I'm doing, and I kind of like it that way.

[979] But the Angel Syndicate is now the largest syndicate in the world.

[980] I've deployed like $185 million in my career as an angel investor.

[981] I'm doing $50 million a year now.

[982] That's awesome.

[983] I'm raising the fourth fund in public.

[984] Like 11 ,000 angels in the syndicate.

[985] This is going at a really significant velocity.

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

[987] and it's in really high -quality companies I'm getting better at there's 11, I have 22 people and 10 on the media side and 12 on the investment side and have the investment team like people don't understand they're like oh you're a solo GP I'm like you have 12 people those people are doing 60 introductory meetings per week 6 -0 and then we're doing maybe 15, 20 second meeting so there's it'll be 100 meetings a week shortly probably across 10 people or 12 people but you're not doing the I'm not doing them yeah and what happens is you had this line with it on If it was on Twist, I think.

[988] Not for me. That's a lot of work.

[989] People say that's a lot of work.

[990] But you're like, yeah, but now for me. That is the new philosophy.

[991] This is why my energy is really high.

[992] This is your, you're on lock.

[993] I have told everybody who comes to work for me, I work 60, 70 hours a week.

[994] Keep up.

[995] If you can't keep up, don't be here.

[996] I'm looking for a fixed 50, a solid 60 hours a week.

[997] You don't have to match me 67, 60 or 70 hours a week, but keep up.

[998] And are you looking in that team?

[999] Are you looking for like the next Jason Calacanis to be a part of that team?

[1000] or is it like someone who likes doing that part?

[1001] Well, let me ask it more directly.

[1002] Is it someone who's content with doing this or are you looking for people that are hungry enough to be the next Jason?

[1003] I'm open to all of it.

[1004] I'm open to all of it.

[1005] They don't need to want to have my, you know, absurd, unhealthy desire in my youth to be successful.

[1006] And if they did, they probably wouldn't come work for me, but maybe they would.

[1007] Actually, I would.

[1008] So, yeah, they probably would.

[1009] Not for very long ago.

[1010] Yeah, mine might be like three years.

[1011] You'd extract.

[1012] People come and they work for two, three, four years and they go start their own venture fund or whatever, muscle to have, that's great.

[1013] But what I told them was, you know, just find the great companies.

[1014] And I looked at investment team meetings, usually there Monday.

[1015] People do it for an hour or two, and then they go to lunch.

[1016] I said, I want to do it twice a week.

[1017] Tuesday and Thursdays, 2 to 4 p .m. Hit me with companies.

[1018] So that was another innovation I did.

[1019] And I also brought Mike Savino, who was my first boss, when I was in my 20s doing IT and I brought him on as president so this is like one of my lifelong best friends and I said run the company here's what I want to do the podcast meet with founders do the LP fundraising that's it you teach the course Are you enjoying the LP fundraising?

[1020] I am now yeah I'm kind of like remember an X I don't know if you watch Billions Oh yeah every episode great so you know like at some point he was like, I'm going to go raise money.

[1021] Yeah, it's cap raise time.

[1022] It's cap raise time.

[1023] And like wags is like, so I got my wags, Mike Savino's my wags.

[1024] Yeah.

[1025] And I got my wags who just fixes everything.

[1026] And I'm like, I'm going to go raise money.

[1027] And so literally was like, we're doing 506C.

[1028] And they're like, don't do that.

[1029] You're, you're now, you were in kind of this one bucket with your capital.

[1030] And now you're going simultaneously in two directions of you want the public and you want the big institutions, right?

[1031] We'll see.

[1032] I've had select institutions.

[1033] institutions make small bets.

[1034] The first fund was 10.

[1035] The next fund was 11.

[1036] And then the last fund was 44 million.

[1037] The first fund I deployed in five years, second fund two years, the third fund two and a half.

[1038] Five years.

[1039] I was just, that was my first fund.

[1040] It was, you know, me, Bill Gurley, Dave Goldberg, rest in peace, Tony Shea rest in peace, David Sachs, Chimov.

[1041] Just a bunch of my friends put money in.

[1042] And it was to see if I wanted to be a venture capitalist and do this as a career.

[1043] And I was like, yeah, I just did it over five years.

[1044] And the second one, I raised 11, took me six months to a year to raise the first it took me the second one took three to six months the no it took six months the third one took me three months to six months and in this one i think i'll wind up raising in the first 10 days what i raised in the first yeah a couple of funds wow i literally did two webinars a couple hundred people came to each so for people who are listening 506c is you can raise in public which means you just can tell people I'm raising a fund.

[1045] And I was like, well, I'm doing all in.

[1046] It doesn't make any money.

[1047] I have this week in startups.

[1048] And I watched a bunch of these young, inspiring VCs raise publicly.

[1049] Right.

[1050] You didn't raise publicly.

[1051] No. I thought about it, but for a whole bunch of reasons.

[1052] Well, it's kind of scary because people don't do it.

[1053] But if you have no track record and you want to raise, so like this guy Mac the VC, you did a great episode with him.

[1054] Yeah, it was great.

[1055] I had him on.

[1056] I had like, you know, first time found.

[1057] for a season of Angel, which is like a subsection of the This Week in Surrows podcast.

[1058] And I became an LPN's fund and he just told me like, I just did like hundreds of meetings.

[1059] I did like five meetings a day for a year.

[1060] And I raised my whatever $10 million.

[1061] And he's African -American.

[1062] And he's like, it's just a matter of how hard do you want to work?

[1063] And I'm like, well, careful saying that publicly because there's a group of people who do not want you saying that.

[1064] He's like, no, it's just all you have to do is like, you go to Angelish, you set it up.

[1065] And then you just start talking to other VCs.

[1066] You just have to be willing to take 50 meetings a week.

[1067] I'm like, dude, do not say that it's easy to raise a venture fund as a black man in Silicon Pally.

[1068] But that's his position is, it's not that it's easy, but that it's possible.

[1069] You find your people who believe that with you, and then they believe in you, and then they back you.

[1070] Correct.

[1071] Correct.

[1072] Correct.

[1073] And so the whole thing is, but what I noted when I was taking my notes watching him was so many times, people like, oh, you're, when's your next fund?

[1074] I'm like three years.

[1075] They're like, oh, let me know.

[1076] And I'm like, okay.

[1077] Right.

[1078] I'll put that right there in the place where I keep everyone who tells me. Yeah, three years from now what to do, yeah.

[1079] And so, you know, I mentioned it on All In.

[1080] I tweeted it and all of a sudden, you know, I had a thousand people sign out before.

[1081] Is there a limit to the number of LPs you're going to have with a five or six?

[1082] It's 250 accredited, up to 10 million, and then 2 ,000 QPs.

[1083] And so it's a lot more work.

[1084] And QPs.

[1085] Not for you.

[1086] But not for me. To catch everyone up.

[1087] Qualified purchasers.

[1088] People who have.

[1089] Look at you playing, Jason.

[1090] I know you know what a QP is.

[1091] I just want to dish the ball.

[1092] I think it's $5 million in investable.

[1093] assets, and then accredited now is 200 if you're an individual for the last two years, each of the last two years, and 300 if you're a couple, each of the last two years in income or a million dollars.

[1094] In net worth, outside of your primary residence.

[1095] So there's a whole, and these things are going to change over time, but I believe that we're going to have a test for accreditation, and you'll be able to be sophisticated if you take a course.

[1096] So I think that's coming in the coming year.

[1097] So just like I democratized Angel investing world, the book Angel was the first syndicate on Angel list, the most successful syndicate on Angel.

[1098] List, created my own, got the domain name, the syndicate, created the largest one, have done 265 syndicate deals by far, like, the largest amount of anybody, I think.

[1099] I don't know.

[1100] Which, I mean, now as a participant with the Fund on Angel List, like, these are, like, those are big numbers.

[1101] Like, we've done four SPPs on Angel List, and we have the fun, too, but like, you know, like, that's a lot.

[1102] You're hurting cats.

[1103] You need to have a lot of people.

[1104] But anyway, putting all that together, I think now is the time to democratize venture capital.

[1105] So that's what I'm attempting to do here.

[1106] I want more people who are accredited in qualified purchases who've never been in a venture fund to look at the asset class and just consider it.

[1107] It's high risk, it's high reward.

[1108] I'm in 20 venture funds myself, including yours.

[1109] Thank you.

[1110] But don't pitch, Jason.

[1111] I'm sure I will do yours.

[1112] No, I mean, I'm just going to pick them based on people I know or people I know online or put on a pod.

[1113] And, you know, I'll do one or two new ones a year.

[1114] Well, this is kind of to the conversation earlier.

[1115] Like, on the Internet, this is the democratizing.

[1116] thing.

[1117] Nobody's going to just give you, if you just, you know, nobody's going to just invest in your fund.

[1118] But if you go do stuff, yes.

[1119] And then people like, oh, Jason does stuff.

[1120] Great, I'm my back to Jason.

[1121] Ben does stuff.

[1122] Be of action.

[1123] Yeah.

[1124] And it doesn't mean you have to start our pockets.

[1125] You could be a blog.

[1126] You could do events.

[1127] You could create Founder University, whatever it is.

[1128] You can do any of those things.

[1129] You can have a track where you'd be an advisor to startups, whatever it is.

[1130] Do you like the idea?

[1131] I'm curious, as someone that's always raised from sort of individuals, do you, do you like the idea of having something?

[1132] institution be like can we invest 15 million dollars oh yeah of course i mean i've had five you know million dollar checks 10 million dollar checks in the fund from institute from you know fund to funds and institutions you know but i would very much at some point i don't need it but i would be meaningful for me uh both my parents are cancer survivors to have memorial sloan kettering's endowment or an endowment ucsf or something like yeah somebody like that you know if they wanted i would work you know, really hard to try to get them a great return.

[1133] I would find more, I would find even more meaning in what I do.

[1134] Yep.

[1135] And, you know, I got that from Sequoia.

[1136] Like, you know, they would have this Sequoia dinner every year for the founders and they would say, here are what the foundations, who are LPs are doing with the money you made for them with your companies.

[1137] Yeah.

[1138] Click, click, click.

[1139] Here's what Ford Foundation's doing.

[1140] Here's what this foundations are his way.

[1141] And you're And their conference rooms are named after their LPs are.

[1142] And this is real.

[1143] Powerful.

[1144] Like, I find we have like state pension funds and stuff like that and don't make you get in PSL Ventures and like you take it much more seriously.

[1145] You're like I am, because it's not just about the reward.

[1146] It's not like, oh, I'm so excited about what we're going to do for them.

[1147] It's like, this is really important to preserve and grow, but like preserve this capital.

[1148] Yeah, yeah.

[1149] Which the psychology of doing that while you're taking big swings with asymmetric upside, that I find to be a fascinating dance.

[1150] That was like one of the seasons of that of billions was he's like, I'm going to be a family office.

[1151] No, I'm going to raise my own phone.

[1152] And so there's just natural tension for acts like, which should it be?

[1153] And he decided, yeah, I like when I have other people's money because he seemed to perceive like.

[1154] I think he felt that he wasn't a somebody in his ecosystem, in his community without managing outside capital.

[1155] I think it's like playing, you know, in the bubble with nobody in the stands versus.

[1156] Right.

[1157] getting on the court at Madison Square Guard.

[1158] And there's people in the staves.

[1159] Your numbers don't mean anything unless you're putting them up for.

[1160] Dude, I'm doing this public, or I should say quasi -public.

[1161] People I still have to sign up to, you know, come to a webinar.

[1162] But I'm sharing with them like, here's my totality of my investments.

[1163] And here's what I've done.

[1164] And here's what I plan on doing with my team.

[1165] So, you know, I'm kind of enjoying it.

[1166] And if, you know, I've met with all the top endowments in the world over the years.

[1167] They're very kind to me, but it's always been like solo GP as a blocker, no track record.

[1168] Your fund is so small.

[1169] Small fun.

[1170] We're a $50 billion endowment.

[1171] Yeah, and you know, like, you know, at some point, like one of the ones who's the most rigorous, I wouldn't say exactly which one, was like, we have a lot of respect for you.

[1172] We know who you are.

[1173] People would like you to sign a book and take a selfie with you when you're here.

[1174] But I just want to be straight with you.

[1175] We don't add many funds.

[1176] And if you go through our process, it's going to take.

[1177] take a lot of your time and it's going to result in you not getting our money this time.

[1178] I don't want to put you through that, but I respect you.

[1179] And if you want to do it, we'll do it.

[1180] But maybe just put one more fund on the board and let's talk on the next one.

[1181] And I was like, let's do that.

[1182] I don't need the money.

[1183] Let's wait.

[1184] And I think what a lot of these funds are doing was that in the last fund cycle?

[1185] That was in the third fund cycle.

[1186] Yeah.

[1187] So now.

[1188] So I will contact them.

[1189] What I decided to do was, let's see what my syndicate members and the public want to do.

[1190] Let's see which QPs come out of the woodwork.

[1191] And literally, I did the second call this week, the first one last week.

[1192] I'm doing the third one next week.

[1193] And it's been so productive.

[1194] I added two more.

[1195] So I'm going to do five webinars this fall.

[1196] And then I'm going to go on the road and start meeting with folks.

[1197] Are there any downsides to doing the raising in public thing other than?

[1198] Not that I can see.

[1199] I mean, I guess you could fail in public to fail to raise the fund.

[1200] That doesn't seem like something you're scared of.

[1201] No. I could also, you know, the fraying thing, you know, is I looked at the model and I said, you know what I could do?

[1202] I could just invest my own money in each company and then syndicate them and never have another LP.

[1203] Right.

[1204] But then you're raising capital every single time you're making an investment.

[1205] Yeah.

[1206] And I'm getting deal by deal carry.

[1207] And I have 100 % of my investment, not 25 % carry on it.

[1208] and I don't ever have to talk to anybody.

[1209] I could just say, I'm placing this bet.

[1210] Would anybody like to join me?

[1211] And I don't have to have a fund.

[1212] I don't have to do audits.

[1213] I don't have to do any work.

[1214] So literally this, you know, it's so funny hearing you say this.

[1215] Myself, lots of our other friends in the ecosystem that are in similar positions, they're having this same question.

[1216] Like, on the one hand, I could do what you just said and do very little work, but have it all be pure.

[1217] On the other, I could go do.

[1218] what you are actually doing and, like, raise, have LPs be account of it.

[1219] Yeah.

[1220] How did you weigh these two?

[1221] I'm going into my second era, my second decade of investing.

[1222] And I, again, the last two years, a lot of like sort of post -pandemic and Tony's death thinking, huh, like, what's possible here?

[1223] Because I've won so much in my life.

[1224] I don't mean to be obnoxious about this.

[1225] I know it probably sounds that way.

[1226] But for a kid who's, you know, going to be a cop to be where I am, and this is why, like, when the guys break my chops on the pot, I'm like, guys, I don't aspire to be a billionaire.

[1227] It's not important to me. If it was, I would do a late stage fund.

[1228] I aspire to be happy and do what I love doing every day, which is the podcast, maybe get in 40 days of skiing, hang out with my kids, take them on the mountain, and then meet with, like, you know, early founders and be able to say, I helped that company at the earliest stages.

[1229] That, to me, is the rush.

[1230] I found him first.

[1231] I backed him first.

[1232] I sat there with them and figured it out with them.

[1233] We were talking about the legendary twist episode 180 with you and Travis.

[1234] Yes.

[1235] Like, man, that's the secret before the show stuff, David.

[1236] Yeah, that is.

[1237] But from the juicy before the show.

[1238] I can talk about Travis.

[1239] Yeah, but that was like, you know, Urbu was such a baby company back then.

[1240] And like, you know.

[1241] One city.

[1242] I mean, I invested, and I had an open angel for him where Siam Bannister and Chris Raleck from First Run, you know, invested in the company.

[1243] I think they both met them there.

[1244] Saka was there too, but he already, he had a relationship with Travis, so I can't take any credit for that.

[1245] And Kevin Sistram was watching, and I was going to kick him out because he was at this co -working space called Dogpatchez.

[1246] I worked there, too.

[1247] I worked as Co -Tweet.

[1248] Yeah, so he was, oh, Co -Tweet, I know that.

[1249] So he's sitting over there building bourbon.

[1250] And Saka's like, can bourbon come?

[1251] in i'm like fuck no this is like private shit and he's like but and i'm like just tell him to sit at his desk and i won't keep him out wait this open angel form was at dog patch labs here on the pier no way i think that three years then they shut down because it was going to collapse condemned yeah condemned um so that was there and uh navarre also did a bunch of like events there for angel i at the time noval and i were very friendly um not not friendly now but not we don't hang out or we but we used to hang um kind of bummed about that if i'm being honest.

[1252] I really respect him.

[1253] And he was doing something called venture hacks at the time.

[1254] So he would just send an email with, here are the five companies.

[1255] And I was doing it in person.

[1256] And he's like, I'm going to do this angel list.

[1257] I'm like, well, I'm just in person thing.

[1258] And he's like, great, let's just trade notes or whatever.

[1259] And then he set me the syndicate thing.

[1260] He's like, do you know about SPVs?

[1261] I was like, I don't explain it to me. He taught me what SPVs were.

[1262] He introduced me to a sure fund management, which I wound up investing in.

[1263] Did you buy that?

[1264] I didn't buy it.

[1265] I mean, I bought 5 % of the company.

[1266] I was listed in it.

[1267] But They back everybody, and they've done more SPVs.

[1268] It's like, I don't know if they're up to $10 ,000, $5 ,000.

[1269] I mean, they've done a ton of that.

[1270] Seriously, great group over there.

[1271] And so he taught me how to do syndicates.

[1272] And the first one I did was calm at $4 ,000 or $5 million.

[1273] That's nuts.

[1274] It's funny.

[1275] I was looking for your...

[1276] Like, literally, like, winning a championship the first time you step on the court.

[1277] I was looking at your track record, getting ready for this.

[1278] And I was telling David, like, I think the word that I used...

[1279] Because, like, obviously Uber is some ridiculous multiple on a return.

[1280] But then there's these other ones.

[1281] ones that are like promising but early and then there's other ones where it's been a less than uber multiple it's still good at uber multiple but you look at calm you just i looked at david and i was like he sharpshoetered that one like that one i could be even more proud of because i mean it was like ridiculously early and like a super low basis they had it was four million dollars we put 370a k and own 6 % and uh they didn't raise any money until it was a 250 million dollar violation so no dilution um and sharpshooter sharp shooter and And it's really like I might even cry like telling the story, but Alex too and I became very good friends.

[1282] And Michael Acton, you know, afterwards, because he wasn't actively running calm while Alex was.

[1283] Alex at some conference, I was interviewing him and doing a little victory lap for him and giving him his flowers.

[1284] And he said, I just want to stop and tell you, you don't actually know this story, but we were going to shut the company down.

[1285] And Mike and I had a conversation.

[1286] What?

[1287] Do we take your money?

[1288] But we're not sure about this, but you believed in us so much and you insisted on us taking the money, but we had just pitched 40 investors and they all said no. And we were trying to debate if we could in good conscience burn your money to do this.

[1289] And we probably, Com would not be here for you.

[1290] And they found product market fit while burning through your money.

[1291] I think so.

[1292] I think so because you're like, take more of my money.

[1293] No, no. But I mean, if they think about that as like a, that is not the case with Uber a Robin Hood.

[1294] I was along for the ride.

[1295] Let's be honest.

[1296] I did not change the trajectory of the company.

[1297] But like, but for Jason Calacanus, calm was not.

[1298] Well, he said, it's, they were going to shut it down, possibly.

[1299] I don't believe that they would, but I do think it was on the table.

[1300] That's, like, real angel investing.

[1301] That's real.

[1302] There's a lot of, like, individuals participating in venture rounds.

[1303] And, like, yeah.

[1304] No offense.

[1305] Oh, hey.

[1306] I don't take any offense.

[1307] So, like, call that angel investing, but, like, coming in when the company could die, needs 100k, 200k, 300k to get it to the stage where they...

[1308] I had $10 ,000 of revenue to date, I think, when I invested.

[1309] Like ever.

[1310] Yeah, because they were selling the app for $10.

[1311] Because remember, at the early stages, there was no subscription model.

[1312] Right.

[1313] In the App Store.

[1314] You just sold an app for $10, a person had it for life.

[1315] So the business model of apps was make a lighter for a dollar, then make lighter two, and charge $3, and then lighter four would come out.

[1316] And you were like, well, this doesn't make any sense.

[1317] It's like making Microsoft Word 1 .0, you're...

[1318] buy it, throw it away.

[1319] It's like, but we can just update it.

[1320] And it's like, yeah, but we need to make more money.

[1321] So shut the old one down.

[1322] So you'd buy Angry Birds and you buy Angry Birds, too, Angry Birds 3.

[1323] It was a really weird time.

[1324] And then they were like, they told me like, you know, because, you know, I was under NDA as well.

[1325] Hey, subscriptions are coming.

[1326] That's going to change everything.

[1327] And they were going to do $10 a year.

[1328] And I said, to Alex and Michael, how much does it cost to go to a meditation class?

[1329] It's donation based.

[1330] And there's only like 10 places you can go.

[1331] I'm like, well, what's a suggested donation?

[1332] It's like $20 in LA.

[1333] I said, you want to church $10 a year.

[1334] It's $20 a month.

[1335] How often do you have to do this to get value?

[1336] Yeah, $20 a visit.

[1337] I said, how often do you have to do this to get value?

[1338] It should be a daily practice.

[1339] We're like, how often do you have to go and learn?

[1340] I said, if you go weekly, that's good.

[1341] I said, if you go, that's $80 a month to go.

[1342] And we're charging $10 a year.

[1343] So that's like $1 ,000 a year versus $10.

[1344] What if it was $10 a month?

[1345] They're like, we've been thinking about that.

[1346] I was like, okay.

[1347] And they're like, okay, yeah, I think we're going to do that.

[1348] And then they went to $10 a month or whatever.

[1349] And they didn't wind up at $60 a year or whatever it was.

[1350] But we got a money printing machine pretty quickly.

[1351] So I've never made an investment at like pre -product market fit that's like now worth over, you know, a billion dollars.

[1352] Like that's a very early to very successful.

[1353] And I'm curious, like, did it feel any different when you were making that investment?

[1354] Were you like, there's something more special here?

[1355] Of course.

[1356] Than my normal investment.

[1357] Absolutely.

[1358] Really?

[1359] Absolutely.

[1360] And that's what I've basically.

[1361] turned into a playbook at launch and that I'm teaching these 12 people how to do is how to do that.

[1362] What do you think it was?

[1363] Like what was, when you look back and you're like...

[1364] Nine factors.

[1365] Nine.

[1366] Okay, all right.

[1367] Well, AngelDout University.

[1368] No, I don't even teach you an angel at university, but I'm training my team when they're meeting with those 60 companies and every time they pitch me one, they say this has three of the nine, this has four of the nine.

[1369] And then I'm creating the anti -list.

[1370] These are the things that kill companies.

[1371] So how many of the 15 things?

[1372] We have a long list of things that kill companies.

[1373] How many of the red flags does it have?

[1374] Reasons to not invest?

[1375] How many reasons to invest does it have?

[1376] And, you know, like one of them for me, and everybody's got the difference while, so I won't give all of them, but one of them is world -class design.

[1377] And so I'm trying to teach people what world -class design is.

[1378] And world -class design to me is if you were to look at all the companies in the space, this one would have the best design.

[1379] Or this would be one of the top 10%.

[1380] So if you were to look at something like Com or Robin Hood, okay, they're the best -looking app with the best U .S. of anybody in the category.

[1381] Right.

[1382] So Com was better than Headspace, Robin.

[1383] Who was better than E -Trade?

[1384] I mean, it doesn't take a rocket science to look at them.

[1385] But when I first explained this to my team, they would bring me companies and they'd say, world -class design.

[1386] And I'm like, I really like the design.

[1387] I'm like, pull it up.

[1388] And they pull it up.

[1389] And I'm like, that's a template from, you know, like a website builder.

[1390] And it's a stock photo.

[1391] But where's the actual design of the product?

[1392] And they're like, oh, that's on this product page.

[1393] And I was like, okay.

[1394] Again, that's just like the, I mean, if this was a bank's website, maybe, but that's not world class.

[1395] That's serviceable design.

[1396] That's utilitarian design.

[1397] That's okay design.

[1398] That's good design.

[1399] It's not world class.

[1400] So let's, if we're going to say world class, like a world class performance is different than a serviceable performance.

[1401] World class cinematography, world class script, world class dialogue.

[1402] That's different.

[1403] And that's, and then product velocity is the other one I like.

[1404] So, okay, we met with this company in June.

[1405] It's now July.

[1406] What's changed?

[1407] about the product.

[1408] And they're like, we don't know.

[1409] I'm like, okay, well, let's find out.

[1410] Where's their change log?

[1411] Where's their roadmap?

[1412] So in the earliest stages, you might have revenue traction or user traction, but you might be able to ask them for their product roadmap.

[1413] And somebody like Travis would be like, yeah, here, get on the phone with this guy and we'll walk you through it.

[1414] Here's what we're debating about on Sunday.

[1415] We're reprioritized.

[1416] And then a month later, they're like, check, check, check.

[1417] And then you go, like, if we're with Rowe, it's superhuman.

[1418] And I was investor in his company before that report of Rowe, like the change log at superhuman.

[1419] superhuman that people don't realize like the like bink bank new feature bank new feature oh boom we fix grammarly oh bink we have calendar boop oh we got a new calendar feature boop we got this feature and you're like hmm so here's an interesting question we should ask ruffle this we've had on the show three times now product genius like the the parallels between superhuman and figma are uncanny like design led founder like revolutionary design in the software rewriting the entire browser stack in order to get the performance and And I remember it being breakthrough when it came out, and then the only thing that I can recall being different between then and now is adding a calendar thing that I don't use and a mobile app, and iPad support.

[1420] And why?

[1421] Outlook support.

[1422] You just don't, you know, when you hit Command K, you probably know 50 % of the features.

[1423] Right.

[1424] Like, do you use remind me of this?

[1425] I do.

[1426] Okay, great.

[1427] Do you use labels?

[1428] Do you do snippets?

[1429] I do.

[1430] Okay.

[1431] Yeah.

[1432] Which it was all there when I started using it, three, four years ago.

[1433] I think a lot of those things have gotten better and better.

[1434] Yeah.

[1435] So it's just that like polish, polish, polish, polish.

[1436] I really like want them to make snippets multiplayer.

[1437] I want to share my snippets.

[1438] Oh, yeah.

[1439] Oh, it's team.

[1440] I love.

[1441] Yeah, so I want all of David's pass emails.

[1442] They're so nice.

[1443] I don't do email anymore.

[1444] Like, I do it on the phone?

[1445] No, no, I just don't do email.

[1446] I don't email.

[1447] I don't email.

[1448] I actually do pass emails from I've been literally creating a collection of how to pass with my team, and I'm standardizing that.

[1449] I'm trying to.

[1450] I don't know that I'll be successful.

[1451] This may be a mistake, but I'm trying to just not have, I don't end up having a conversation with the company if I'm not going to invest.

[1452] No, but you must say, hey, we are not going to invest.

[1453] You've took a pitch.

[1454] Oh, no, I get it.

[1455] I don't.

[1456] How do you say that?

[1457] You basically don't take a pitch unless you're going to invest.

[1458] It's the weirdest thing.

[1459] Oh, that's very weird.

[1460] So you do all your work up front.

[1461] You front load it, the DAC, everything?

[1462] We're in this unique position.

[1463] You are too.

[1464] But with Acquired, we're like, you know, we have every six months, we have six companies that we work with on the show as our sponsors and our partners.

[1465] And we get to know them really well.

[1466] It's modern treasury.

[1467] And I'm now an investor in just about all of those companies.

[1468] So it's not like they're pitching me. It's growth stage investing.

[1469] Yes.

[1470] It's like they're clearly the winner.

[1471] They're not yet priced as if they're the winner.

[1472] most of the time, but they're going to just keep compounding.

[1473] Yeah, good luck.

[1474] Yeah, pricing's going to be hard.

[1475] We'll see.

[1476] We'll see.

[1477] We'll see.

[1478] Yeah, I don't know what's going to happen to these companies after, you know, the flat is the new up, but I think, you know, 50 % haircut is the new flat.

[1479] Well, public comps got hit 50 plus percent.

[1480] Yeah, I mean, they got hit harder again.

[1481] Yeah, I mean, I'm buying equities right now.

[1482] I've been doing it at jatrading .com, and I am going to buy more.

[1483] Sorry about all I picks.

[1484] a couple weeks ago.

[1485] Which one?

[1486] Whatever I told you.

[1487] Oh, yeah, no, no. I actually love Taiwan Semiconductor.

[1488] And Stitchfakes was the other one.

[1489] No, I didn't know.

[1490] I didn't think Twilio.

[1491] Twilio was yours and I love that one too.

[1492] And I like Shopify as a pick.

[1493] I'm actually really enjoying it.

[1494] It's really balancing out, not investment advice, but it's balancing out my understanding of what public success is compared to private.

[1495] And so for me, it's just a way, like, am I going to fight with a black?

[1496] No, I'm a Jedi.

[1497] I use a lightsaber.

[1498] But, you know, I'll learn to use a blaster.

[1499] It's not as elegant.

[1500] It's helpful.

[1501] It's really helpful.

[1502] If you look at the very best people, the best GPs in venture over the past two decades, they all trade public stocks.

[1503] And they do it for this same reason.

[1504] They're going to fight with the saber.

[1505] Yeah.

[1506] But like they want to know how to also use a blaster.

[1507] Or how to fight in an X wing or something.

[1508] Like it's not what a Jedi does, but Jedi will do it.

[1509] It also keeps you really.

[1510] sensitive to the public cycles so that like it's not that you have to think about the public comps when you're investing but you have to be aware of how much those will change yeah and early stage investing it's almost silly to compare it to like my opinion is it's very silly to compare to public comps because the only thing you know for sure is we're going to be at a different place in the cycle by the time this company gets liquid so it's ridiculous but it's helpful to drive into you like how much variability there is when was the last time it was this different Yeah, I'm really enjoying understanding what the founders of those companies go through versus the founders of the private companies that go through, what the boards, decisions the board has to make of a public company versus the board of a private company.

[1511] So I'd like to join a public board at some point.

[1512] It's probably not a good idea for me to have said that because I might get an invite for one and that might be too much work.

[1513] But yeah, especially given the market right now, I'm very careful.

[1514] But you could also invite me to do that.

[1515] But it's just, it's been great.

[1516] through the show now.

[1517] You have relationships with public company founders.

[1518] Sure, of course.

[1519] If I really wanted to, I'm sure I could lobby 20 I know and get the spot.

[1520] You don't have to be on the board though.

[1521] You can have a great relationship with doing the analysis and I'm doing it anyway with Molly every day.

[1522] Okay, you know, Twilios or Adobe's come back.

[1523] I just bought Adobe this week when they bought Figmon.

[1524] So funny, so did I. Not investment advice.

[1525] Not investment advice.

[1526] But I was like They bought Figma tanked.

[1527] Okay, so here's my theory on this.

[1528] They bought Figma and tanked.

[1529] And I was like, why did people hate this?

[1530] And they're like, oh no, Adobe's admitting defeat.

[1531] And that like they can and evaded house or and to me i look at it like adobe has customer channel and it was foretold five plus years ago that they were not going to build the next figma like that would be a full rewrite of their entire software stack so buying the thing even though they paid a tremendous premium 50x revenue multiple because of the network effects that figma has and obviously all the product stuff but if they can get that through adobe's channel Like, I think that is an absolute win -win acquisition.

[1532] And all these people that are like, oh, they're going to ruin it.

[1533] They're going to kill Figma.

[1534] No, they're not.

[1535] That's why they paid $20 billion for it and have a gigantic bonus for Dillon to stay on board.

[1536] Yes.

[1537] They're taking a YouTube approach.

[1538] I think everybody in M &A knows now.

[1539] Yeah.

[1540] Like, WhatsApp.

[1541] WhatsApp.

[1542] Just leave it alone.

[1543] Don't screw it up.

[1544] And then, so I like your analysis.

[1545] I added to that analysis is if you're not going to, to win the war and you can build an alliance and then fight another war?

[1546] Like, they've just removed the downside of Figma creating Photoshop.

[1547] I'd be concerned for Adobe if they didn't buy Figma.

[1548] Correct.

[1549] So the fact that you're giving us a discount on the shares for them doing the right thing is like Christmas.

[1550] Like, thank you.

[1551] You just discounted the right move.

[1552] Fantastic.

[1553] It would be like, people are like, oh, you know, the Warriors signed Kevin D. Durant.

[1554] And you know what?

[1555] We're going to lower the...

[1556] The Vegas odds are going to.

[1557] We're lowering the cost of...

[1558] But they paid a lot to get them on the team, so...

[1559] Yeah, and oh, you know what?

[1560] We're going to lower the cost of the tickets.

[1561] It's like, okay, I'll buy courtside seats or, you know, or they're lowering the odds in Vegas.

[1562] It's like, wait, why are you lowering the odds?

[1563] Their odds increased.

[1564] I'll place that bed.

[1565] So it's just an obvious bet.

[1566] And then there's all that's left is Canva and Melanie's awesome.

[1567] Totally a different thing.

[1568] But, yeah, and they have a free Canva already.

[1569] And, you know, what if there's always the internal people who are penciling out that spreadsheet.

[1570] There's a group of MBAs who penciled out that spreadsheet with Figma, no offense to MBAs who are listening.

[1571] And they said, hey boss, if X, Y, if X, Y, Z and they said, you know, here's like five potential paths.

[1572] If we make Figma free for 10 users and whatever, or if we, you know, take whatever Figma costs and then we blend it with the Adobe suite, okay, we would get this many more Figma users.

[1573] But we know when we get Figma users, then we get non -designers to pay for it.

[1574] So right now, Adobe has a bunch of designers paying for it.

[1575] But they may not have all the non -designers in there.

[1576] Only designers pay Adobe.

[1577] Well, no, they have marketing cloud, but that's a totally different set of.

[1578] But when you look at Figma, like, I got a Figma account.

[1579] Like people who are doing, giving feedback on designs, the business.

[1580] The business side, the sales side can get into Figma.

[1581] Plus they got the whole creator class.

[1582] Exactly.

[1583] So I think you're opening up the aperture of who design software is for with Figma.

[1584] It's for BD.

[1585] It's for the CEO.

[1586] Sure, the CFO can come in and take a look at the product.

[1587] Oh, legal should come in and take a look at the product.

[1588] Yeah, buy them a seat.

[1589] So it's like, Slack is for the dev team.

[1590] And it's like, yeah, and the sales team.

[1591] And ops.

[1592] And anybody else might as well be on there, because that's where everybody is.

[1593] So that's what I think is going to have with Figma.

[1594] It's like everybody's going to have a Figma account in the future.

[1595] Just to watch the product team.

[1596] build the product and put a comment in.

[1597] And who cares if it's $100 a year?

[1598] It's cost to doing business.

[1599] Any company that has that kind of strong network effects inside an organization deserves a meaningful revenue multiple because their differentiator is literally the company's moat.

[1600] So like I tweeted this, but like if I have a castle and it has a moat around it that is much wider or deeper than your identical castle, shouldn't you pay more for my castle because it's more defendable?

[1601] 100 % like the virality of I think Sachs made this point on Allend two weeks ago which was like if they're paying 50x now and the company's growing they're paying 20x next year 25x who cares right you're seeing such a high growth company and then I was just thinking well somebody's got a theory there and when I sold weblogs to AOL people are like oh my god these people are idiots they gave $30 million dollars to you know for weblogs Inc they've only got 200K in revenue what they didn't realize was AOL autos AOL tech AOL lifestyle those were sold out at like a $90 RPM revenue per thousand pages.

[1602] The ads, different CPMs.

[1603] So then they would put an Engadget or an auto blog story or blogging baby or whatever other blog we had on the homepage of AOL.

[1604] And a half million people would flow through.

[1605] And then they would put those ads on our sites.

[1606] And then they would blow out $50 ,000 or $100 ,000 in ads a day on a blog.

[1607] And those people were like great because it was costing AOL to make content like $500 per piece of content, $3 ,000 per piece of content on AOL .com slash autos, whatever.

[1608] And we were doing it for, at the time, $5 a blog post because we said, well, people can write $4 an hour, so it's $20 an hour, and it's $6 minimum wage.

[1609] It means that's 50 years ago.

[1610] The internet media game has changed so much.

[1611] And then I was like, okay.

[1612] You guys were doing 200K annual revenue?

[1613] We had done 200K to date over the 18 months.

[1614] What is it?

[1615] I mean, now like the world we're in today.

[1616] Multiple, and they were like, Jake Cowles has robbed.

[1617] And I was like, okay, no. 30 million dollars sale?

[1618] I look like idiot.

[1619] What do you think?

[1620] Like, here's a, I look like an idiot five years later.

[1621] And that's the best, the best M &A is when you look like you robbed the bank.

[1622] Yeah.

[1623] And then five years later, it looks like you robbed the founder.

[1624] YouTube, Instagram.

[1625] Figma will be in this category.

[1626] Like, yeah, when they bought Instagram, they're like 30 people work at this company and they gave them a billion dollars.

[1627] You guys are morons.

[1628] And now it's a $150 company.

[1629] Here's a thought exercise question.

[1630] Obviously irrelevant because you don't monetize it.

[1631] What do you think the enterprise value of all in is?

[1632] Well, it would do $10 million in, when I was at the Code Conference, a lot of people have been trying to buy it or put it as part of their network, obviously.

[1633] Which would kill it.

[1634] Yeah.

[1635] My partners are right.

[1636] Let's not make money from it.

[1637] Part of the delightfulness of it is that we're not trying to monetize it.

[1638] Well, but you do get a huge economic value out of it.

[1639] Even with that's always been, Schmach pulled me aside at some point and was like, hey, Schmach, like, just we're friends.

[1640] Like, you're all, your next fun won't be bigger.

[1641] Hey, dumbass.

[1642] And I was like, you know, when you have a friend who can be like, hey, dumbass.

[1643] Yeah.

[1644] Like, that's a good friend.

[1645] So I appreciate Chmott saying that.

[1646] And he's right.

[1647] And it's playing out.

[1648] And we had a rule, no, no talking our books on the pod.

[1649] But we kind of talked about it.

[1650] And we're like, the pot is great when we talk about our bets.

[1651] Right.

[1652] So explaining our bets, not talking our book is the new philosophy.

[1653] So, like, Friedberg just started doing that.

[1654] fack, you know, I, in break call.

[1655] Yeah, he did.

[1656] He just, uh, found a target for it.

[1657] Chamaath talked about, um, the healthcare company.

[1658] The healthcare company, which is, I mean, we wanted to talk about that because Chimov and I both agree, like, maybe we're, I mean, maybe, like, we're definitely overprescribing these drugs to kids, like for ADHD and attention drugs and adults are taking too many.

[1659] I think that that's not disputable.

[1660] Uh, I think all the science is showing that.

[1661] Um, so, you know, to make software, that could help kids with ADHD is like noble.

[1662] But I think people want to hear us explain our bets.

[1663] So, you know, explaining our bets, I think is kind of a cool aspect of the show.

[1664] Talking your book is lame, but explaining your bets is cool.

[1665] So anyway, in the event, did a couple million dollars, had a small profit.

[1666] But it was the number one tech event of the year by far.

[1667] So, you know, I'm kind of bummed that, you know, Freeberg's a little bit of a blocker for it, but I might turn them around and we'll have a vote maybe in the fall.

[1668] I'm doing another one.

[1669] Well, I'm going to do another one.

[1670] The question is, am I doing it under the all -end brand, or do I have to create a new brand for it?

[1671] And so I told the guys, listen, I'm going to do it again.

[1672] Well, code conference is done.

[1673] So, like, there's a vacuum.

[1674] Code conference is done.

[1675] Yeah, they need a new host.

[1676] That's crazy that that can be done.

[1677] Like, it's such a valuable.

[1678] No, no, I talked to Bankoff about it, and he's been very public.

[1679] You know, Kara Swisher, I think, is going to do the pivot stuff and wants to do other stuff.

[1680] And, you know, I really respect what Kara has done, you know, in terms of like she does stuff and then she moves on to the next thing and tries like you know it's kind of my approach as well which is like Bob Dylan you know said like don't look back kind of thing and he always tried to make the next album and forget about the past one and much to the chagrin of people who loved him as a folk artist and didn't like you know like a Rolling Stone and when he went electric they booed him you know it's like really you're booing Bob Dylan because he's using an electric guitar are you guys dumb like did you hear all along the watchtower like this is incredible and so I think you know Carr -Swisher, like, moving on, but Jim said he's going to keep doing it.

[1681] And, you know, it's probably a small list of people who could actually host that credibly, you know, a very small list.

[1682] Which you're definitely on?

[1683] I am.

[1684] You think?

[1685] How could you not be on it?

[1686] I mean, I'm not even saying that to, like, make you feel like.

[1687] No, I'm joking.

[1688] I'm being a little bit of position.

[1689] Okay, okay.

[1690] You're joking about being humble.

[1691] But if it had that kind of prestige, it seems like Freedberg would want to do it.

[1692] It seemed more like the thing he was averse to is the like.

[1693] Yeah, I mean, whatever, the issue is.

[1694] found our issues.

[1695] We will all have issues.

[1696] But I think there's basically two possibilities for Olin Summit.

[1697] I'm going to present it to the boys and say, like, here's the plan.

[1698] Yes or no. And we agree, we'll put it to a vote.

[1699] So we put it to a vote.

[1700] If three of us want to do it, we'll do it.

[1701] And if two of us want to do it, then we can't.

[1702] And if I already, Freeburger already said, if you do it on your own with a different name, I'll come and support you and I'll show up to do a talk or do an interview.

[1703] whatever.

[1704] And I was like, great.

[1705] So I'll do it with a different name if they don't want to do it.

[1706] And the fans can decide if they want to come or not.

[1707] Partially in.

[1708] Partially in.

[1709] Exactly.

[1710] So, you know, it's up to the boys.

[1711] They want to do it, but it was like a pretty great success.

[1712] Colin.

[1713] Do you already have call -in?

[1714] Well, yeah.

[1715] And I started doing a, I started doing a call -in show called After All In for the last two episodes where I took calls about the last episode of just to support David because I don't think people remember how great that app is.

[1716] And it's really made great progress.

[1717] I want to be supportive of him.

[1718] And I have a small investment in it.

[1719] Do you, um, very meaningful, but.

[1720] On the one hand, this is ridiculous.

[1721] On the other hand, it might be ridiculously low.

[1722] Do you think?

[1723] It's worth 50 million to answer your question.

[1724] 50 to 100 million.

[1725] I mean, as a top, as a top 40 podcast, it's worth at least 50 million.

[1726] On its own, though.

[1727] But I mean, like, economic value that the four of you.

[1728] Oh, who knows?

[1729] Over the lifetime.

[1730] Like, if Chimoth or Sachs or I or Freedberg were to get, but one more deal out of it.

[1731] And it's an Uber.

[1732] The economic value is nine figures, possibly 10, you know, like, so, yeah, that's the thing.

[1733] Like, I think, like, man, weblogs, like, you were doing 200K of revenue.

[1734] You sold it for 30 million.

[1735] Pretty great.

[1736] Takeaway, yeah.

[1737] And now, look at this, like, you know.

[1738] Yeah, I mean, listen, I hope it keeps going.

[1739] I hope we can keep it on track.

[1740] And, you know, I love doing pods.

[1741] This weekend startups is a juggernaut as well, you know.

[1742] Yeah, that would have for 10 years and all in is.

[1743] What is that, like, quarter million listeners or something?

[1744] Yeah, some in that range.

[1745] Yeah.

[1746] I mean, it's hundreds of thousands per episode.

[1747] and, yeah, it's a very niche podcast.

[1748] You know, I'm not trying to make it all in.

[1749] I'm trying to make it for founders.

[1750] And so, you know, if in order to make it bigger, it'd have to be worse for founders.

[1751] Right.

[1752] And that's what we talk about.

[1753] It's like what we think about with ourselves.

[1754] I want founders and capital allocators to listen to it.

[1755] Our sponsor for this episode is a brand new one for us.

[1756] Statsig.

[1757] 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 a course.

[1758] Yeah.

[1759] For those of you who haven't listened, VJ's story is amazing.

[1760] Before founding Statsig, VJ 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.

[1761] He also had a front row seat to all of the incredible product engineering tools that let Facebook continuously experiment and roll out product features to billions of users around the world.

[1762] Yep.

[1763] So now Statsig is the modern version of that promise and available to all companies building great products.

[1764] Statscig is a feature management and experimentation platform that helps product teams ship faster, automate A -B testing, and see the impact every feature is having on the core business metrics.

[1765] The tool gives visualizations backed by a powerful stats engine unlocking real -time product observability.

[1766] So what does that actually mean?

[1767] It lets you tie a new feature that you just shipped to a core metric in your business and then instantly know if it made a difference or not in how your customers use your product.

[1768] It's super cool.

[1769] Statsig lets you make actual data -driven decisions about product changes, test them with different user groups around the world, and get statistically accurate reporting on the impact.

[1770] Customers include Notion, Brex, OpenAI, FlipCart, Figma, Microsoft, and Cruise Automation.

[1771] There are like so many more that we could name.

[1772] I mean, I'm looking at the list, Plex and Versel, friends of the show at Rec Room, Vanta.

[1773] They like literally have hundreds of customers now.

[1774] Also, Statsig is a great platform for rolling out and testing AI product features.

[1775] So for anyone who's used Notions' awesome generative AI features and watched how fast that product has evolved, all of that was managed with Statsig.

[1776] Yep.

[1777] If you're experimenting with new AI features for your product and you want to know if it's really making a difference, for your KPI's StatsSig is awesome for that.

[1778] They can now ingest data from data warehouses.

[1779] So it works with your company's data wherever it's stored.

[1780] So you can quickly get started no matter how your feature flagging is set up today.

[1781] You don't even have to migrate from any current solution you might have.

[1782] We're pumped to be working with them.

[1783] You can click the link in the show notes or go on over to stat sig .com to get started.

[1784] And when you do, just tell them that you heard about them from Ben and David here on Acquired.

[1785] I'm not trying to move up the rankings.

[1786] I don't mind, you know, hanging with, you know, all in being number one in tech and then hanging out with you guys at, you know, slumming it at six to 15 with you guys in the rankings.

[1787] It's like, that's where we belong.

[1788] Look, I got number one on lock.

[1789] But who's counting?

[1790] Whatever, you know, like that's where we belong with these things, right?

[1791] Like, it's like, it's a niche podcast by definition, right?

[1792] Like, it's not supposed to appeal to everybody.

[1793] And you try, if you want to appeal to everybody, like, read the Bible.

[1794] Like, that's, you go to that this is the beauty of the internet.

[1795] who reads Bible passages and he and huge it's like if you can literally true crime true crime religion read the Bible or Ben Shapiro dunking on lips the end that's like that's or do it or do it daily but Joe Rogan's out right he's on Spotify right right you know he's not in the other ranking so I mean we're I want a daily news program for 20 minutes like but that's not what I want to do I want to talk for an hour or three about deep topics in founders and capital out of be a fun acquired episode is Howard Stern.

[1796] I feel like it's underappreciated how much Howard Stern...

[1797] I copied my...

[1798] That's the playbook right there for me. That should be the next Taylor Swift type episode that we do.

[1799] Yeah, no for sure.

[1800] He wrote the playbook for all this.

[1801] I literally took notes for it.

[1802] King of all media.

[1803] Do you know him?

[1804] I have never met him.

[1805] I'd love to at some point.

[1806] I have a lot of respect for him.

[1807] I mean, obviously he did crazy stuff when he was young and that shock jock stuff.

[1808] But he, in his later years, became a great interview.

[1809] Great interview.

[1810] Great interview where he really refined his technique.

[1811] I really appreciate that about him.

[1812] And he created characters.

[1813] Sound familiar?

[1814] Yep.

[1815] He branded them.

[1816] Yep.

[1817] He showcased them, the whack pack, you know, all this stuff.

[1818] Did he ever do an event?

[1819] He used to do live events.

[1820] He did the U .S. Open Source, where, and then he would do Howard Stern's like New Year's Eve celebration.

[1821] So, yes, he did the equivalent of those in New York.

[1822] But it was a very New York thing.

[1823] So he, like, he played tennis against Baba Booie.

[1824] But, I mean, he got 10 ,000 people to show up and buy tickets to a tennis match that they pumped up, you know, like for whatever number of months.

[1825] I remember this for my childhood.

[1826] And then he did his books, which were phenomenal.

[1827] And he did a movie.

[1828] He did a movie.

[1829] He did TV shows.

[1830] So he's done a lot of stuff.

[1831] And I'm just starting the process of doing a reality show right now.

[1832] So I'm literally going to do like.

[1833] Are you really?

[1834] Yeah.

[1835] I mean, I had done.

[1836] Just you or the besties?

[1837] No, just me. The besties don't want to do it.

[1838] They don't have time for it.

[1839] I mean, there was talk of like maybe all in, you know, kind of going on to one of those services.

[1840] Like, people had reached out.

[1841] Like, hey, would this work?

[1842] You know.

[1843] That's a lot more work, though.

[1844] Well, you know.

[1845] we would have to show up in a location, we'd have to do it weekly, you know, there'd be some formats, some shiny floor, whatever.

[1846] It's a, it's a different beast.

[1847] I don't think they have the time for it, if I'm being honest.

[1848] But for me, I would like to do a reality show in the Gordon Ramsey kind of vein, you know, where I'm helping founders.

[1849] I think it would be great for reach.

[1850] So I'm, I had done a reality TV show with NBC.

[1851] And the Weinstein Corporation.

[1852] Oh, wow.

[1853] Yeah.

[1854] And it didn't make it on air, but I had.

[1855] have the...

[1856] You should be a Shark Tank judge.

[1857] I had been...

[1858] They had reached out before Mark Burnett had reached out early on when it was Dragons Den before when they were going to bring it here.

[1859] So when it was Dragons Den, they had reached out early, but I wasn't very successful back then.

[1860] I wish...

[1861] But, you know, I think now I think I would have the credibility and the advice to give that I could do a Gordon Ramsey -style show that would be very entertaining and educational and be completely different than, you know, the fundraising aspect and the pitch aspect of Shark Tank.

[1862] So I'm not going to do that, but I'm, you know, I've got, you know, the, I won't say which one, but a very major, the major, you know, reality TV folks reached out.

[1863] I think in part, was all that was doing so well.

[1864] Would you, do founders and companies feel comfortable?

[1865] Like, I feel like a really amazing window and insight would be the type of conversations that you have with a founder as they're building the company.

[1866] Would founders and companies be open to that?

[1867] Yeah, so the NBC show I had done the pilot for, which never made it on air.

[1868] what was really good was really about, you know, me incubating companies.

[1869] And they spent like $400 ,000 doing the pilot.

[1870] It was really good.

[1871] And it would have been a big hit.

[1872] Did it get canceled because of the Hartle -Loyne -Steen stuff?

[1873] Wow.

[1874] So they were just like anything that was in his company.

[1875] And all the IP is dead because he's a monster.

[1876] And so anything associated with it.

[1877] But you got to remember, he did Project Runway.

[1878] So he had done some of these giant shows.

[1879] People don't know that about that.

[1880] That's right.

[1881] I forgot.

[1882] Yeah, that had the TWC at the, beginning.

[1883] Exactly.

[1884] So, you know, NBC, you know, NBC bought the show in the room, loved it and did the pilot and it came close.

[1885] And Chmoth was on that episode, actually.

[1886] He did the pilot with me. Oh, my God.

[1887] He was like my VC friend who came in and it was, it's hilarious.

[1888] No, it's hilarious.

[1889] But I'm excited to do it.

[1890] If it works out, it works out.

[1891] If it doesn't, you know, no skin off my back.

[1892] But I like the media space.

[1893] And then, you know, I, this is the thing.

[1894] I'm choosing to do media because I get joy out of it.

[1895] I'm 51 now.

[1896] I'll be gone soon.

[1897] I want to enjoy.

[1898] I will not be gone soon.

[1899] Well, you know, you never know.

[1900] And, you know, I've been to your friends.

[1901] Yeah.

[1902] I have two friends.

[1903] Yeah.

[1904] I have two friends who died young and I'm just like, I, you know, I talk to my wife.

[1905] I was like, I don't know.

[1906] Like, what if I make it another year or make it 25 years?

[1907] But I want to make it count.

[1908] I'm not going for max dollars.

[1909] Like, and so when the guys break my chops about that, I'm like, guys, it's not my priority.

[1910] Like, literally maximizing money is like, well, also, like, you're probably going to.

[1911] It's not.

[1912] now we're like literally not in the top 10 what is more money going to do like you know literally you get a plan like you want to understand my life like it is ridiculous and charmed like I can do whatever I want I have enough money to do whatever my kids are fine I can have whatever I want I don't care about like a third home like it's I have a ski house I have my regular house it's good I'm good my kids have their college paid for I'm good 100 % I literally do not care about do you feel like that's a demon that you fight is like no any alert or No, I had it when I was younger.

[1913] I wanted to be powerful.

[1914] I wanted to be important.

[1915] I wanted to have money.

[1916] I wanted to be seen.

[1917] I wanted people to recognize my greatness like any person recognize me for what I do.

[1918] I got all that.

[1919] It literally does not even come up my radar.

[1920] To have more money is the last thing I'm thinking about.

[1921] I do want to have, I do want to be the greatest investor of all time.

[1922] Like to me that's meaningful or be one of the...

[1923] I want to be, like I know I'm Mount Rushmore for angels.

[1924] I want to be Mount Rushmore for all investors.

[1925] So when you guys do your thing, in 10, 20 years.

[1926] And it's like, okay, you know, here's Doug Leone and Moritz.

[1927] And, you know, here's, you know, John Dorr, here's Gurley.

[1928] Like, if we are making them out Rushmore, you want to be on that with them.

[1929] I would like to make it there, or at least be in the conversations.

[1930] All right, listeners, we kicked Jason out of the room again.

[1931] Because we have our next sponsor of the episode, our very good longtime friends over at, Tiny.

[1932] The Berkshire Hathaway of the Internet, if you'll recall.

[1933] Indeed, indeed.

[1934] There are so much so the Berkshire Hathaway of the Internet that, as we told you about a few seasons ago, they literally built a business on the Internet selling busts of Warren and Charlie that you can order.

[1935] Berkshirenerds .orgshirenerds.

[1936] That's not what we're here to talk to you about today, though.

[1937] They've got something new to share with us this season that we've been talking a little bit about, kind of from the founder angle, but we want to share with you from the VC angle.

[1938] Yeah.

[1939] So the core business of Tiny is, acquiring wonderful internet businesses.

[1940] These are businesses doing five million or more in revenue at 30 to 40 percent operating margins.

[1941] Well, and the DNA really comes from Andrew and his partners originally running MetaLab.

[1942] And of course, it was a very successful.

[1943] It is a very successful design agency.

[1944] That started spitting off cash.

[1945] What do you do with the extra cash?

[1946] Well, they know how to run a great internet business with MetaLab.

[1947] And so they started buying more and more and more businesses and so now with this awesome portfolio dribble pixel union creative market 8020 girl boss these are all tiny companies and so what are they doing differently now it's funny it's different in a sense but it really is the same tiny playbook that they've always been running to buy wonderful internet businesses but something changed in the last five years we were in this crazy go -go era where lots of businesses even ones that really aren't the shape of what venture capital should be funding, well, most venture capitalists were funding those businesses too.

[1948] And so you end up in this situation where you've got a lot of companies that have raised a lot of money that probably aren't tripling, quadrupling you over year or the way you would sort of expect a venture business to be doing to raise their next round of capital, especially in this environment.

[1949] And so if the business is growing, you know, 20, 30%, 40%, and it can get profitable or it is profitable, well, most of the time.

[1950] That doesn't really make sense in the context of a venture portfolio.

[1951] Right.

[1952] But the founders probably want to keep running that business.

[1953] They probably want to keep serving those customers doing their life's work.

[1954] Exactly.

[1955] And you end up with a lot of these companies in a portfolio that are like capable of being tiny like businesses, but are not going to provide a big exit that's going to move the needle for the venture portfolio.

[1956] Well, Tiny realized they can provide the perfect solution to this problem for the VCs on the boards of these companies, for the founders running these companies, and most importantly, for Tiny to then come in, partner with these founders and own these companies in perpetuity without looking for an exit.

[1957] So really, what Tiny can kind of do is come in, buy the company from the VCs, or a lot of the company from the VCs, get them money back, some or all the layback.

[1958] And most importantly, get their time back, get off the board.

[1959] So they've capacity to do new deals.

[1960] So it's great for founders to keep doing their life's work.

[1961] They can figure out a structure with Tiny.

[1962] Tiny is very good at figuring out structures that make sense to align interests.

[1963] It's really super cool.

[1964] Honestly, like I've talked with a bunch of folks varying different financial groups and institutions over the years who have had some version of this idea and it's never gotten off the ground and I'm so glad that Tiny is now doing it and they are the perfect ones to do it and this is the perfect time to do it.

[1965] So very excited for this to exist.

[1966] Yes.

[1967] Well, if you are running a business like that or you are invested in a business like that or your friend is invested in a business like that, you really should shoot a note to hi at tiny .com and just tell them that Ben and David sent you.

[1968] Don't tell him Jason sent you.

[1969] He's not here right now.

[1970] You can say Jason sent them too.

[1971] All right.

[1972] Our thanks to Tiny.

[1973] When you guys are having the conversation in 20 years and I'm gone or I'm retired, and you're saying Mount Rushmore...

[1974] It's hard to imagine you retiring.

[1975] Yeah, I think it was possible.

[1976] I met Don Valentine when they were like, you know, he was not active investment, but when I pitched Mahalo, he was in the room, he came up.

[1977] I talked to him.

[1978] He was, oh, he was still hanging out there all the time.

[1979] Yeah, yeah, like, why he retire?

[1980] He was just awesome.

[1981] But, you know, if you had that conversation right now about Mount Rushmore, like, you got to...

[1982] Who's on your Mount Rushmore?

[1983] Well, I mean, you got to have Don Valentine.

[1984] Yeah.

[1985] Right, that's just not possible.

[1986] And how are you scoping it?

[1987] because you probably need Paul Graham, too.

[1988] Well, yeah, I mean, you got Paul Graham is in the running, for sure.

[1989] But that's like a number of startups, but there's a lot of big ones in there.

[1990] You have big impact.

[1991] So Paul Graham's definitely running.

[1992] But, okay, so do you go with John Doors in there along with, so if you're doing firms, it's a lot easier because you get Kostla, Dorr, and Perkins, Tom Perkins.

[1993] You get the three of them at once.

[1994] Yeah, yeah.

[1995] Which people forget.

[1996] Vanne Cozla spent a decade at Kleiner Perkins with John Dorr.

[1997] Like, yeah, and you, and you had, yeah.

[1998] So, I mean, you look at that firm.

[1999] It's like, that's like the OKC with like James Hardin, you know, whatever.

[2000] But then you have Doug, Leonie, Mike Moritz, and Valentine.

[2001] Rule off.

[2002] Well, we've had all of them there active all the same time.

[2003] For those 30 years and it's like, well, that's Mount Rushmore, right?

[2004] So if it's a Mount Rushmore of Mount Rushmore's is kind of how you might look at it.

[2005] You know, you definitely have to have.

[2006] We just did Benchmark.

[2007] You got to have.

[2008] The Fab 4 era of the FAB 4 era of benchmark was truly something special.

[2009] It's kind of like, it kind of builds itself the Mount Rushmore right now, right?

[2010] It's going to be Sequoia Kleiner benchmark.

[2011] And then we're like, we're going to have a big debate on the fourth arm.

[2012] Like is it, well, it just depends how wide we're willing to scope it.

[2013] Is it like traditional Series A type venture firms?

[2014] I mean, is it Angelus, Naval?

[2015] Right.

[2016] That's had a huge impact.

[2017] Do you put YC in there?

[2018] Do you put YC or TechStars, both have a huge impact?

[2019] Do you put, um, you put, um, you know.

[2020] You know, who else can be in there?

[2021] That's just...

[2022] You can't say YC in TechStars.

[2023] Not yet, but Founder's fun.

[2024] It's a totally different thing.

[2025] Yeah, for sure.

[2026] I mean, three orders of magnitude, more significant.

[2027] They've done the same number of companies, I think, but just in terms of returns, yes.

[2028] But TechStars, I think, was a little before White Combinator.

[2029] But anyway, you definitely have Y Combinators, you know, and running for that four spot, I guess.

[2030] And then who else would you put in there?

[2031] Massa?

[2032] Oh, wow.

[2033] That's high beta.

[2034] Well, no, I mean, but Maybe founders fund Maybe, I mean, Excel, I don't know, Excel would be in the running, for sure.

[2035] It's Ron Comway.

[2036] I think the way you kind of have to define it, which is unfortunate because it means that it's going to be a long -ass time before your firm hits Mount Rushmore is three successful generational transitions where each of the generations would have been on Mount Rushmore.

[2037] All right, so then let's just do this.

[2038] Instead of Mount Rushmore, because we're talking firms, so for firms you do Mount Rushmore, right?

[2039] So I think if you were just going to say, the Hall of Fame.

[2040] Oh, yeah.

[2041] Just the Hall of Fame.

[2042] And the Hall of Fame has, let you say.

[2043] Oh, dude, we should open the Venture Capital Hall of Fame.

[2044] The Venture Capital Hall of Fame, Capital Hall of Fame, top 25.

[2045] I was trying to figure out when we were doing the Benchmark episode research, which will be out by the time this comes out.

[2046] 2480 Sand Hill Road is a very special building.

[2047] It was the Forthought PowerPoint.

[2048] The Quadris Complex.

[2049] Quadris Complex.

[2050] Yeah.

[2051] Then it was Microsoft Silicon Valley.

[2052] before the shit about this.

[2053] Oh, no. Three of us are so excited right now.

[2054] This is the internet.

[2055] This is like, wow.

[2056] We have aggregated all the other people who care about this.

[2057] Everybody else who cares about this.

[2058] It's us.

[2059] And like, Sebastian, who wrote the power on those.

[2060] Yeah, yeah, yeah.

[2061] You guys are taking this way too seriously.

[2062] It's not bad in.

[2063] But then we're like alone yelling in David's house.

[2064] TVI.

[2065] TVI.

[2066] Meryl Picker.

[2067] TVI.

[2068] That's a good.

[2069] August capital.

[2070] One on 20 on Microsoft.

[2071] Shasta Capital.

[2072] All in this same building.

[2073] And I think there's some.

[2074] space for rent in there.

[2075] I don't want to go live down there, but I think we've got to take out a lease just to put the museum, the Hall Fame.

[2076] A Venture Capital Hall Fame is something we could collaborate on.

[2077] We should just do it.

[2078] We'll just do it.

[2079] We'll just, we'll just do it like every year.

[2080] We'll induct somebody.

[2081] We'll get up there, the three of us and be like, this year we're inducting into the Venture Capital.

[2082] We should totally do this.

[2083] Kent, Ohio exists.

[2084] You know, Cooperstown.

[2085] There is a, what do you call it?

[2086] It'd be our Cooperstown.

[2087] Yeah, there is the computer history museum.

[2088] But it's not a. That's for the PC.

[2089] which is totally valid, but it's not for capital allocators.

[2090] It's not for people.

[2091] Like, yeah, there should be a Hall of Fame.

[2092] And do we, like, do we Midas List style ask people for the real hard truth numbers?

[2093] No, no, no, it's about impact.

[2094] You have to think.

[2095] The three of us, we decide.

[2096] It has to be impact on the game.

[2097] Does the NBCA have, like, a Lifetime Achievement Award?

[2098] Is that the closest thing?

[2099] It doesn't really exist anymore.

[2100] Yeah, no, it's about impact, legacy, like, the intent of the person.

[2101] Right.

[2102] This is why, like, Paul Graham would be, like, you know, first ballot.

[2103] This is why, you know.

[2104] Okay, who are the first ballot entrance?

[2105] It's so obvious.

[2106] We've already talked about it.

[2107] We already talked about it.

[2108] Those are all first ballot.

[2109] Do we have anybody who we haven't talked about or who's not obvious but would be a first ballot?

[2110] You can't, this is what I'd say.

[2111] If you're under 20 years, you're not, like, just like, let's wait to your 25 years in.

[2112] Yeah, just like the Sports Hall of Fame.

[2113] You got to have a, yeah, you got to be, you're not playing in the league anymore.

[2114] So Paul Graham's still playing in the league.

[2115] Does Jeff Bezos count?

[2116] Like, wow, I mean, how many investments has he made?

[2117] That Google investment is crazy.

[2118] So there's that, but there's also like, I think Amazon is the best venture firm of all time.

[2119] It just in terms of like, it's internal.

[2120] They're not separate companies.

[2121] So, yes, capital allocating, lowercase C, lowercase A. They've been great at placing bets.

[2122] But you're right.

[2123] Jeff Basis is probably the most successful angel of all time.

[2124] Yeah, I mean, if you just did it up dollar.

[2125] Yeah, and L .P. You got to put on, you know, when you're looking at it, I think you've got to look at impact.

[2126] Like impact on the game, legacy.

[2127] So is Carmelo Anthony, Hall of Fame.

[2128] Of course he is, but he didn't win a ring, but he, you know, he's Carmelo Anthony, right?

[2129] Like, or Charles Barkley, didn't win a ring, but...

[2130] Okay, so then we got, like, Arthur Rock.

[2131] Like, you got to look at, like, the founding father type.

[2132] Of course, of course, yeah, there's no doubt.

[2133] I mean, that's, like, going back to Bob Coosie or whatever, going back to, like, some really, like, you know, people who built the league kind of situation before it became the league, right?

[2134] So you got the league, and you have the people before the league, you know, people in the league.

[2135] Yeah.

[2136] You've been generational shit right here, you know, Patrick Ewing.

[2137] Yep.

[2138] You know, because I think, like, you look at Gurley, like, he's part of that Patrick Ewing generation, right?

[2139] Like, that Heim Elijah on Charles Barkley generation.

[2140] You start talking about Founders Fund or YC or Angelist.

[2141] Like, okay, now you're talking about more modern era.

[2142] Yeah.

[2143] Still going.

[2144] Modern era after 2000.

[2145] But if you started before 2000, it's a different group.

[2146] Do you notice we haven't talked about Andreessen and Horowitz in this conversation?

[2147] Oh, God.

[2148] Who cares?

[2149] No, impact on the game, they're in.

[2150] Both of them are in.

[2151] For sure.

[2152] No doubt.

[2153] No, they totally are.

[2154] Impact on the game?

[2155] They totally change the game.

[2156] I mean, I just feel like it's gratuitous.

[2157] It's just like raising $10 billion, three funds a year.

[2158] I want to see what happens with the crypto stuff I think they're just an index of venture I find it quite soulless if I'm being honest like I feel like it's a giant index on venture and I don't think that their hearts are super into it I do think they have interesting ambitions though I think this that's the problem it's more ambition It's more ambition than soulful But there should be a JP Morgan or Goldman Sachs of Silicon Valley And they are that for sure I don't know Yeah why is why does Goldman Sachs manage the money of entrepreneurs I just feel it's too Okay fine but I just feel like it's it's too premeditated and less soulful.

[2159] I feel like it's a soulful business where like your intentionality and your relationship with the founders really matters.

[2160] It's not the craft.

[2161] I mean it's like the literal antithesis of this.

[2162] It's industrialization.

[2163] It's the industrialization of it.

[2164] It's the factorization of it.

[2165] And listen, I'm sure it'll be very successful at the end of the day, all the returns will be great except for the crypto stuff.

[2166] Well, I mean, there'll be mean reversion because like when you get the law of large numbers you have mean reversion.

[2167] Exactly.

[2168] Exactly.

[2169] It will be mean reversion for sure.

[2170] I mean, that was, at some point, they leaked a lot of their returns, and they were like, eh, not fair.

[2171] That was the 2015 thing.

[2172] Well, they did, actually.

[2173] It was early.

[2174] So, yeah, that was stupid that the journalist didn't understand it.

[2175] But there were some older ones.

[2176] But it was like, during that time, like, you start comparing it to Sequoia or benchmark.

[2177] I think it's going to, I think in the arc, it will not be comparable to benchmark in Sequoia.

[2178] And we, I mean, made a lot of hay of the fact that they had, that they made $11 billion in profit on Coinbase.

[2179] And like, I do not think they sold out of that.

[2180] No, they did not make $11 billion in profit as a day.

[2181] Well, I mean, it's timing is everything.

[2182] We'll see.

[2183] It's interesting, too.

[2184] I mean, having just done this benchmark episode, like the benchmark fund seven, one of if not the best institutional size fund of all time, just like unreal.

[2185] But even that, like the fluctuation in the marks on that fund, and it'll probably end up between 15 -25x maybe.

[2186] But it fluctuates up and down so much.

[2187] Yeah, of course.

[2188] I mean, we live in a very volatile time.

[2189] I like the Hall of Fame idea.

[2190] It's kind of interesting.

[2191] I think that actually would be a fun thing.

[2192] We should get some space on Sand Hill and put up a...

[2193] No, we could just do it as like a dinner.

[2194] We just literally have...

[2195] We don't need a space.

[2196] We could just start in a restaurant, but you could get like a little hall and say we're going to induct into the Venture Capital Hall of Fame the following people and here they are.

[2197] And we just have three pictures, boom, boom, boom.

[2198] And you just drop it and these are three people and then people come up and say something about the person.

[2199] And I think like we could, do like the three who we would hope would be there and then we'll have we do it like the sports where you have the person who's being inducted chooses who inducts them sure that's fun yeah so rooloff does Doug yeah yeah whoever does Maritz yeah yeah but John Parker does Maritz Mike chooses who you know he can have Larry and Sergey come up he has Jason Calcanus come up and be like Larry and Sergey yeah yeah totally yeah uh John Dorwood uh ask Bezos.

[2200] It's a killer.

[2201] It's a killer idea.

[2202] I mean, we just do Bezos, Doug and Mike.

[2203] And then.

[2204] Who inducts you?

[2205] You do one in the memoriam.

[2206] Yes.

[2207] You would do one in memoriam.

[2208] Yes, exactly.

[2209] You know, whatever.

[2210] Because it would be anti -climactic if the only person, because we will induct on first, and if the only person that we inducted that year wasn't a living person who could attend.

[2211] Yeah, you do a combo.

[2212] You do a combo.

[2213] Maybe it's four people a year, you know.

[2214] You have to think, how do you want to get to 25, so maybe it's, It's, you want to get to 25 to 50 over 10, 20 years.

[2215] So, yeah, maybe it's three a year.

[2216] In order for this to, like, feel good, I think you're right that it has to be about impact, not about returns.

[2217] No, returns is like so, that would be like saying it's like album sold for the Rock and Hall Full of Fame.

[2218] Right.

[2219] There are people.

[2220] That'd be a very Andreessen Harrow's way to do it as well.

[2221] Yeah, Andrews is, but, oh, what's the total assets under management?

[2222] You know, and it's like, okay, dude, we get it.

[2223] Nickelback sold a lot of albums.

[2224] Yeah, they're the nickelback eventually.

[2225] No, I didn't mean that.

[2226] You said that.

[2227] You said it.

[2228] I wasn't talking about it, Andreessen.

[2229] Oh, God.

[2230] Oh, God.

[2231] Oh, God.

[2232] Like a million.

[2233] Now they've sold tons of albums.

[2234] Right.

[2235] I'm not saying that they're a million of, no, but they're just like, oh boy.

[2236] There's, you know, if you were to look at Ron Conway, does Ron Conway, who had a bigger impact?

[2237] Ron Conway or Andreessen?

[2238] Like, I think it's a conversation, you know?

[2239] And if you, because Ron Conway, when I came into the industry, like, there was at one point, I was at the Crunchies.

[2240] And Ron Conway, at one point, like somebody said, like, hey, can everybody stand up who said Ron Conway invest in?

[2241] in their company and a hundred people stood up and my mind was like oh whoa angel investing's cool i mean i wasn't an angel investor at the time i was you know long before i became a scout but that i always remember that moment when like a hundred people stood up that that like inspired partially inspired in the scout program is that what gave you the is that what like put you in business as an angel invest is what put me in business yeah what happened was i had was your uber investment you personally or was that's sequoia's money okay yeah and we were like rule off and i were trying to figure out, like, do we let people know we're doing this or not?

[2242] It was, like, a big controversy at the time.

[2243] Like, we want to keep this stealthy.

[2244] But, I mean, Travis knew, but, you know, it was, it was a pretty great deal, you know.

[2245] It was like, um, you know, at the time they carried 50 -50 at the time.

[2246] Yeah, they dropped it down after that.

[2247] Doug Fiong was, like, and they had 30 % carry at Sequoia at that point, I think.

[2248] Whereas you, I mean, if I were you, I'd be like, 50 % carry to them.

[2249] I can't believe it.

[2250] No, no, no, I mean, Doug had always, they're so classy.

[2251] Doug would always make a joke, would always make a joke.

[2252] I was like, 50 % carry.

[2253] Oh, God.

[2254] We get 30.

[2255] You get 50.

[2256] This is funny.

[2257] We get 30.

[2258] We get a lot of it.

[2259] Pretty funny.

[2260] We're very lucky.

[2261] I think if you look at what we do as capital allocators, I think it's a very special part of the, it's a very special function in the world.

[2262] I take it very seriously, as you do for the retirees you're investing on half of, but also I just think about humanity, and I don't mean to make it heady, but these companies do move the human species forward as...

[2263] Look at Elon.

[2264] Yeah, exactly.

[2265] So the human species getting moved forward by, as Steve Jobs would say, in those commercials, like this is the crazy ones.

[2266] They do need fuel.

[2267] They, you know, maybe don't have an idea of, you know, if they should even build this company.

[2268] And I think the capital allocators really come in and say, here's some fuel.

[2269] You know, here, go fight that war, you know.

[2270] It's fuel and its belief, too.

[2271] I mean, like, your story about com is not uncommon, I think.

[2272] think amongst founders.

[2273] I mean, look at, I mean, the stories about Don Valentine and Atari and other places where he was at Cisco, he's like, so we've got to get this thing back on the rails.

[2274] This thing's going to zero.

[2275] Yeah.

[2276] You know, like, there's a lot of existential moments where things go to zero and like.

[2277] So can I ask you as we start to like drift, drift toward the end of the episode here?

[2278] That's your line.

[2279] That's your favorite line.

[2280] Drift.

[2281] That's the Ben's signature line.

[2282] As we call us here for the end of the last.

[2283] Is this a good format?

[2284] Like, is this different enough from our normal show?

[2285] Should we do this?

[2286] Yeah, I think so.

[2287] Yeah, do you like this?

[2288] I think a casual glass of wine and just, you know, if you have friends of the pod and you want to go deep and talk about them and ever more casual, sure, yeah.

[2289] I mean, I think it's a great way to just have somebody on again, you know?

[2290] So if you profile somebody like, I forgot that I had, you had done like the first episode with me. And that was more about my career and more details.

[2291] And so I'm starting to tell stories over again.

[2292] It's like, well, let's talk about some other stuff, right?

[2293] Yeah.

[2294] So, I think it's like a different context.

[2295] Our audience was one -tenth of the size at that point.

[2296] Well, part of what we, you know, like Lex has done so great with his show.

[2297] Yeah.

[2298] But those type of conversation.

[2299] But I feel like that's more, what's the right word?

[2300] Our shows are about the business of tech.

[2301] Yeah, no, his is intellectual dark.

[2302] I don't know why he's in the tech vertical.

[2303] But I like the format.

[2304] And like Kevin Rose used to do the foundation series and like.

[2305] Yeah, I mean, long -for -wing interviews, like how, I mean, I think Joe Rogan, stole it from Howard and I think it's now Lex stole it from Joe or I want to see him say stole I think you know inspired by yeah so Lex is clearly inspired by Joe and Joe was Joe was in the running to replace Jackie Martling on the Howard Stern show people don't know this so really he was very enamored with Stern and he wanted to be Stern I think and he eventually has supplanted Stern yeah he did become yeah he did become stern and so good on him yeah right down to the you know serious Spotify like right down to it he well yeah doing a platform yeah doing a platform which is what stern did stern had multiple platform deals he did syndication first then he did the serious xm1 because it was a new platform and he built the platform right which is i think what uh yeah which this but actually to bring it all the way full circle back to charlie rose like that he was like a you know business i mean he did more than business but like he would have culture business anybody in new york Because New York, everybody in New York was pretty fucking interesting.

[2306] Yeah.

[2307] He could have somebody from Wall Street, a publisher, an author of somebody who does films, you know.

[2308] He would have like Spike Leon on it.

[2309] You know, he'd have Woody Allen on.

[2310] He would have, you know, any actress on who was doing something interesting, any novelist, Margaret Atwood, anybody was just coming through New York on a press tour.

[2311] You know, you would do your press tour and then you would just go chill with Charlie and you would get to do something long for it.

[2312] Yeah.

[2313] It was like a little like sort of more jazzy.

[2314] you know a little bit more like acoustic so i like this format for you guys do you listen to smart list at all do you know about that show i i have listened to one or two episodes it's bateman will arnett arnett and then somebody else yeah the guy from uh will and grace sean i don't know who that person is but they bring on a surprise guest each time and the other people don't know yes so they're not prepared yes and it's like it's like it's like katy perry it's like chris pratt yes become a big deal i kind of want to do that of tech but like because Wait, you and I don't know who the one of us is bringing somebody.

[2315] You guys are not good, you can't make, you got to know the person's background much better.

[2316] But they all seem to know.

[2317] Because the celebrities carry a certain charisma with them that our industry doesn't have.

[2318] But maybe it doesn't have to be the surprise as much as like, well that the other thing is that even though they have guests, the show is actually about them.

[2319] The guest is a prop.

[2320] In a way, yeah, I guess.

[2321] I've only listened to one or two.

[2322] You know, I see it in the rankings.

[2323] Like, it does incredibly well.

[2324] Like, it's a top 10 or top 25 podcast.

[2325] Is it part of a network?

[2326] Is it part of Spotify or something?

[2327] I don't think so.

[2328] I don't think so.

[2329] It's really weird that Spotify doesn't allow Joe Rogan and call her daddy on iTunes because the advertising would be huge.

[2330] So why not bake the ads in and put them over there?

[2331] There's some MBA that's run the numbers that says it's more valuable if it's driving new subscribers to Spotify.

[2332] I guess that's it.

[2333] I guess that's it.

[2334] Oh, guess you know what?

[2335] They want to be able to have.

[2336] those new subscribers so when they go renegotiate with the music.

[2337] I saw they're doing audio books too now.

[2338] That's the next piece.

[2339] Yeah, that is the next piece.

[2340] Yeah, they're doing audio books, one -off purchases.

[2341] Smart.

[2342] I mean, audio is great.

[2343] All right.

[2344] It's getting really hot in here.

[2345] It's getting so hot.

[2346] Yeah, we got it.

[2347] For those you know, we're in like a sauna.

[2348] A new, yeah, David's new house.

[2349] David just moved.

[2350] Dave's got a new empty house.

[2351] We, there's kind of like, it's sort of like the shining.

[2352] There's no furniture.

[2353] There's no furniture.

[2354] We just furnish this room.

[2355] We literally, this is all from Craigslist.

[2356] of it literally in the last like two days.

[2357] That explains the smell.

[2358] That, all right.

[2359] You could have, I mean, listen, you're rich, dude.

[2360] Just go on and buy some cream barrel.

[2361] We can't all be Jason Calacanus.

[2362] Oh, you're, no, come on man. I know those fees.

[2363] Oh, my God.

[2364] I have revenue.

[2365] Craigslist.

[2366] I love Craigslist.

[2367] I love it.

[2368] I love it.

[2369] All the time.

[2370] I do not buy any furniture.

[2371] All right.

[2372] I bought a temporary couch on Craigslist.

[2373] It was not.

[2374] No, no. You're going to get robbed.

[2375] Don't do it.

[2376] It's too crazy.

[2377] Craig Newmark.

[2378] I love you, but.

[2379] All right.

[2380] With that.

[2381] With that.

[2382] Our thank you.

[2383] To Vanta.

[2384] Oh, Vanta .com slash Acquired.

[2385] Oh, there you.

[2386] Vanta .com slash acquired.

[2387] Our thank you also, you don't know who the other sponsors are because we haven't, we don't afford them live with you because we felt very strongly that it was, you know, we wanted to make better use of your times.

[2388] I love reading bands.

[2389] You're kidding me?

[2390] Do you want to read our Brex ad?

[2391] They don't sponsor my Potson, no. Brex, maybe they have.

[2392] I don't know.

[2393] The Brex card.

[2394] You know about Brex car.

[2395] Brex, yeah.

[2396] I know a lot of people who use Brex.

[2397] I think we use Brex.

[2398] It is, one of my companies.

[2399] If you're enterprise, if you're global, by far the best corporate spend management.

[2400] It's much more than a card now.

[2401] Yeah, for expenses and everything like that, right?

[2402] And then they've kind of expanded behind that.

[2403] So you can give cars to each of your employees.

[2404] And then if they screw up, you can turn it off or something.

[2405] Yes, exactly.

[2406] If they jump the fence.

[2407] Yeah, you don't want people jump on the fence and they're going crazy.

[2408] All the listeners know, because they heard it like an hour ago.

[2409] They're very familiar.

[2410] Oh, because it's in here.

[2411] So, yeah.

[2412] So that's Brex.

[2413] Shout out Brex.

[2414] Shout out Brex.

[2415] And then.

[2416] Use the promo code twist.

[2417] We share.

[2418] We share this last sponsor.

[2419] These are great folks.

[2420] These are like dear friends and geniuses and raconteurs.

[2421] Masterworks?

[2422] No, no, no. Good guess, though.

[2423] Think smaller but bigger.

[2424] Literally small.

[2425] But secretly huge.

[2426] Tiny.

[2427] Oh, tiny, of course.

[2428] Yes, they're buying companies.

[2429] They're doing a good job.

[2430] Yes, they're creating like the Berkshire of the internet.

[2431] the internet and can you imagine a better time to get the monkey off your back of venture capital and sell your company let's look secure the bag listen to the pc telling you let's go favorite takeout line secure the bag let's go man trust me if you haven't secured the bag yet it's a wonderful experience man there's nothing like getting home with the bag you get that tiny you get that aOL weblogs exit oh man let me tell you something i'll tell you the story what did you do when you secured the bag i'll tell you what happened i got this a funny story i'm in my office and I got Bank of America and I got like low thousands of dollars in my bank of America and I got an American Express card with negative 10 on it and a visa with negative 5 or 10 on it and I'm sitting there and they're like oh wires are good you know the BD people are AOL and so I'm like hitting refresh yeah on the thing this is 2 ,0006 7 5 is 6 yeah I'm hitting refresh I'm hitting refresh and then bing pink pink you know all the numbers come in for the whole, you know, amount.

[2432] And you own most of weblogs, eh?

[2433] Brian and I were equal partners.

[2434] Then we had Peter Rojas had some ownership, and then Mark Cuban was our big investor.

[2435] And by big investor, he put 300K and for 5%.

[2436] So that was a great outcome for him.

[2437] Oh, wow.

[2438] Yeah.

[2439] Or more, maybe I won 10%.

[2440] I think I'm 10%.

[2441] Anyway, long story short, my wife comes in.

[2442] She said, you okay?

[2443] And I said, are you crying?

[2444] And I reached up, and I had a tear in my eye.

[2445] You're like, this is a new experience.

[2446] I've never had this before.

[2447] And she said, I said, why are you crying?

[2448] And I said, I'll never, my family will never have to worry about money again.

[2449] Because I spent my whole life worrying about money.

[2450] You know, my dad had lost the business.

[2451] It was a very cathartic thing for me. And I think people, you know, who are already rich, you know, or maybe who come from means, just they don't understand the concept of living with the fear of being broke and in debt all the time.

[2452] And then when you have the bag, you secure that tiny bag.

[2453] bag.

[2454] And it's a tiny bag, but it's filled with diamonds and cash.

[2455] And you just open it up and say, thank you, tiny.

[2456] Thank you, tiny for securing the bag.

[2457] Acquired .com .com slash tiny No, it's literally, they don't give us a thing.

[2458] Oh, we don't, we don't.

[2459] No, that's right.

[2460] Email, uh, is it high at tiny.

[2461] Uh, and tell them about it.

[2462] Whatever it is.

[2463] Like, just know that tiny.

[2464] Tell them that Ben David and Jason.

[2465] You can mention Jason.

[2466] Yeah.

[2467] You should.

[2468] I did buy a one touch express machine.

[2469] I bought a Jura.

[2470] One touch espresso machine which at the time was like two grand and I was like this is unbelievable that's the that I tried to buy a Ferrari oh they wouldn't sell it to me in Beverly house you were the refraff no new money or something what's yeah basically I went in there and they're like oh yeah what do you am I like to buy a Ferrari today in the 430 and they're like oh we don't have any available and I was like okay can I put myself in the wait list we're not taking names from the wait list so I said to this guy can I ask what do you do here he's like we sell Ferraris I'm like to who you don't know where This is part of their strategy.

[2471] It's part of the strategy.

[2472] It's part of the strategy was they have the Ferraris, but they don't sell the Ferraris to build your steed.

[2473] We're not at any point of your list.

[2474] I was like, well, how long is the wait list?

[2475] He's like, don't even bother getting on it.

[2476] I was like, okay.

[2477] I was like, I'm my cash buyer.

[2478] He's like, everybody's a cash buyer.

[2479] I'm like, okay.

[2480] Can I ask you a question then?

[2481] He's like, sure, come into my office with an espresso.

[2482] You want some Pellegrino?

[2483] I was like, no, I'm good.

[2484] You want some Pellegrino espresso.

[2485] And I was like, I said, I'd have the same one touch.

[2486] Sure.

[2487] And the Italian guy's like, I was like, I don't mean to be rude, but what do you do here all day?

[2488] He's like, well, we deliver the cars and we service them and we sell used cards, pre -owned, certified.

[2489] For more.

[2490] And I was like, oh, I was like, well, I would take a pre -owned one.

[2491] He's like, oh, well, the one you're looking at is pre -owned.

[2492] I was like, no, no, no, the one I'm looking at the 430, the red one out there.

[2493] That's the one I want.

[2494] That's got a sticker in the window.

[2495] He's like, yeah, yeah, we certify them.

[2496] We put the sticker on the window.

[2497] I was like, oh, well, that goes for $230 ,000 or whatever.

[2498] So, yeah, what do you want for?

[2499] He's like, 300.

[2500] And I was like, the sticker says, I was like, no, no, no. This is a potential.

[2501] He used one I was looking at.

[2502] He's like, yeah, you can't get these cars.

[2503] And I was like, so you pay over 70 ,000.

[2504] He's like, but it only has 2 ,000 miles on it.

[2505] And I was like, 2 ,000 miles, 70 ,000 more than new.

[2506] I said, why wouldn't I buy a new?

[2507] He's like, because you can't get them.

[2508] And I just, I'm such an idiot from Brooklyn who doesn't understand the concept that people would pay over the car.

[2509] And I'm just perplexed.

[2510] That would bother me too.

[2511] I was like, all right, well, let me think about it, and I left, and then I was with my friend, and I was like, and I had the Rob report, and it said, like, number one car was the Ferrari F30, and turn the page, it was Corvette C -6 was the number two car.

[2512] And the starting line was, make Ferrari buy two for half the price of a Ferrari and beat them off the line.

[2513] Or something like that.

[2514] And I was like, let's go to the Chevy store.

[2515] Let's go to the Chevy store.

[2516] I walk in, there's corvettes everywhere.

[2517] The guy that looks at me and he goes, you want to buy a Corvette.

[2518] I said, yeah.

[2519] He said, if you buy a Corvette today, I'll give you $5 ,000 off.

[2520] I was like, yeah.

[2521] So we go out in the 405 and we're driving the Corvette, and he's like, this is a Corvette son.

[2522] Like, you're going 70 miles an hour.

[2523] I said, I'm not selling this car to you unless you hit that gas much harder.

[2524] And I said, okay.

[2525] And I punch it to 100 miles per hour.

[2526] The guy's like, yeah, how does that feel?

[2527] I'm like, great.

[2528] We go back.

[2529] I come home with the Corvette.

[2530] I come home with a yellow convertible Corvette.

[2531] I was like, what happened to the Ferrari?

[2532] I was like, this thing only costs $65 ,000.

[2533] It's like $70, and I got $5 grand off.

[2534] And it's American, baby.

[2535] And it's American.

[2536] And that was the car that I famously was, according to Gawker, Robert Scob and myself and Elon, when Elon got the first P1 of the Roadster, he was like, I got it.

[2537] I was like, oh, let's meet in Brentwood.

[2538] And we were driving them at a...

[2539] You were racing.

[2540] We were driving them along Sunset Boulevard.

[2541] A spirited drive.

[2542] A spirited drive along.

[2543] Sunset Boulevard and we did it like five times and five out of five times the Tesla just destroyed the Corvette and I was like I'm doing something wrong and you know then we switch cars I mean and I was like nope electric just going to beat everything and this was the first one that you know first yeah that was it's amazing the prototype that's in space right now it's the cherry red well that's the one that's the one and there's a famous photo of me and Elon in front of the Corvette with that that one's it but there's a famous photo of the two of us uh you know in front of my corvette and his p1 uh and i remember that night like it was yesterday because we were this before the iphone you realize like robert scrob was recording this on his nukia you know yeah these are the memories right like this is the journey that you've been on yeah that's pretty great and this is the stuff you just will cherish forever my life is unbelievable i am so grateful for it and uh thanks for having me on the pod guys listeners thank you so much acquired at fm slash slack come join us we'd love your feedback this is This is a new schick.

[2544] Acquired .fm slash store.

[2545] You can buy cool shirts.

[2546] Shrag.

[2547] Slash jobs.

[2548] Find your next work career experience.

[2549] I just had a bunch of new ones.

[2550] That's right.

[2551] Fire.

[2552] dot FM slash David buys you some smelly furniture.

[2553] My God, it is hot in here.

[2554] All right.

[2555] Let's go eat some food.

[2556] Let's get some sushi or Mexico.

[2557] I don't know what we're going for here.

[2558] That was awesome.

[2559] Oh, so fun.

[2560] Thank you so much.

[2561] Of course.

[2562] All right, listeners.

[2563] We hope you enjoyed that very first acquired sessions with Jason Calacanis.

[2564] It's a new format we're playing with, we would love your thoughts.

[2565] Acquiredfm at gmail .com or tweeted us at Acquired FM.

[2566] I am curious what you liked, what you didn't like.

[2567] And on that note of feedback, we have something that we really, really want you to participate in.

[2568] No pressure or anything, but it would mean the world to us if you did.

[2569] We just launched the 2022 Acquired survey.

[2570] And we've had the wonderful problem of our audience growing a lot since the last time we did one of these and we no longer feel like we have a great handle on who all of you are.

[2571] And so we would be eternally grateful if you would spare the three minutes to participate.

[2572] Tell us a little bit about yourself.

[2573] One lucky winner will get second generation AirPods Pro, which I have been wearing all over the place and are indeed twice as noise canceling, whatever that means Apple, and has some, I think, better battery life too.

[2574] And David, for you, they have very tiny little ear tips, right?

[2575] Yes, for my tiny, tiny ear.

[2576] years.

[2577] I'm so excited about the extra small tips.

[2578] They finally fit in my ears.

[2579] It's awesome.

[2580] 10 other winners will get Acquired T -shirts from our fancy new merch store.

[2581] Again, three minutes to participate at Acquired .fm slash survey, or you can click the link in the show notes.

[2582] And thank you so much for helping us.

[2583] It really does help us run the show here at Acquired World HQ.

[2584] All right, well, with that, our huge thank you to our sponsors for this episode.

[2585] We've got Vanta.

[2586] brex and our friends over at tiny links for each of those are in the show notes and uh with that listeners we'll see you next time we'll see you next time