EP 39: All-In’s Jason Calacanis Joins, Breaking Into Media, Tech in Journalism and the Kanye Controversy

All-In’s Jason Calacanis joins to talk about how he broke into media and how it impacted his success as an entrepreneur. Plus the origins of blogs and the early internet, tech in journalism today, his own experiences as a podcaster and interview, and finally the Kanye controversy. (0:00) Welcome Rashad (2:25) Kanye Controversy (9:32) Elon buys Twitter (13:58) Welcome Jason Calacanis (15:00) NYC and Silicon Alley (18:32) Getting into media (28:52) Web 1.0 to Web 2.0 (34:02) Tech and journalism (44:09) This week in startups (49:48) Palmer Luckey interview (56:56) Kanye on Lex Friedman (59:35) Responsibility as a public figure (1:02:53) All-In and Cartoon Avatars (1:09:23) Capturing lightning in a bottle (1:16:19) Being in the public spotlight (1:22:30) Wrap up Mixed and edited: Justin Hrabovsky Produced: Andrew Nadeau and Rashad Assir Executive Producer: Josh Machiz Music: Griff Lawson 🎙 Listen to the show Apple Podcasts: https://podcasts.apple.com/us/podcast/three-cartoon-avatars/id1606770839 Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1 Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg Follow on Socials 📸 Instagram - https://instagram.com/cartoonavatars 🐦 Twitter - https://twitter.com/cartoonavatars 🎬 Clips on TikTok - https://www.tiktok.com/@cartoonavatars About the Show A Saturday morning podcast hosted by Logan Bartlett (Partner and Managing Director at Redpoint Ventures) covering the tech news with his friends and other people with industry expertise. Executive Producer: Rashad Assir Producer: Leah Clapper Mixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow 📱 X - https://twitter.com/loganbartshow 🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the Show Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member. Tap follow and enable notifications to stay ahead of the game.

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

• 0:05Logan Bartlett?

  Welcome to the 39th episode of Cartoon Avatars. I'm your host, Logan Bartlett, joined today by producer Rashad Assir, as well as, I guess what you're gonna hear on this episode, at least on the back half, is a conversation I had earlier this week with Jason Calacanis. And so, yeah, fun conversation. Jason and I have been going back and forth on this for a while. So, trust people will enjoy that. We talk about a bunch of different things, including his relationship with Palmer Lucky, how All In came to be, a bunch of other, a bunch of other interesting stuff. Jason is, is nothing if not a, a, someone

• 0:47Logan Bartlett?

  that people have opinions about, and he certainly himself in the, in the public square.

• 0:52Speaker 01

  Had you guys met before?

• 0:54Logan Bartlett?

  No. We had got, he invited me on This Week in Startups in the middle of the pandemic. And I actually said no. We were kind of in the middle of fundraising, as well as, I actually didn't know really who he was, and didn't, it was pre-All In, and I, all I saw was him like, sort of, at times, causing just a shitstorm on social media, like going back and forth with Taylor Ruins, and it just seemed very messy in a bunch of different ways. And so, I was fairly new at Redpoint, and was like, hey, I don't want to get involved in, in all that. And then, since then, obviously, I've gotten to know him a little bit. We've

• 1:37Logan Bartlett?

  gone back and forth on podcasts and things like that. And he's been supportive of what we're doing here, pretty publicly at times. And so, yeah, I mean, he, we, I wouldn't say we have any relationship at all, other than we send messages back and forth occasionally about stuff.

• 1:56Speaker 01

  Makes sense. I hadn't realized how long he's been covering tech for, and like, he's like a OG media guy.

• 2:01Logan Bartlett?

  It's wild. It's like, actually, I mean, he was, he talks about it, but he was on the cover of New York Times, like in 94 or something, right? So, he's very used to being in the public eye, and I think really enjoys it, versus the other people within All In, I think it's a little bit new to them. And so, he likes this like pseudo-celebrity thing, for sure.

• 2:25Speaker 01

  That's awesome. What else happened? So the, I guess the big things that happened this week are, well Kanye's just been all over my feed.

• 2:34Logan Bartlett?

  Yeah.

• 2:35Speaker 01

  Any take there?

• 2:36Logan Bartlett?

  How much have you been keeping up with, with all that stuff? Jason and I actually talk about it a little bit.

• 2:41Speaker 01

  Why? He like deletes all of his Instagrams periodically and then like posts a bunch of stuff. So I think I've seen the most recent version of whatever's on his Instagram feed.

• 2:49Logan Bartlett?

  I think, uh, I mean, just to give people a quick context, I assume most people are following this, but like two weeks ago, he wore a, or three weeks ago now, I guess at this point, he wore a white lives matter shirt to a, uh, Paris week fashion show. Um, he went on Tucker Carlson and made comments about Lizzo's weight. Uh, he, uh, discussed wearing a white lives matter shirt. Um, Adidas said that they were going to review their, their relationship. Then he got locked out of, uh, then he got locked out of Instagram. Um, and was posting a, a bunch of anti semitic things, um, on Instagram. He, uh, yeah, then

• 3:30Logan Bartlett?

  he made the decision to buy Parler, which is a right wing friendly social network. Um, he went on Piers Morgan and said, there's nobody that could judge more than straight white men. Balenciaga decided to cut ties with him. Uh, ultimately Adidas decided to cut ties with him. Kim Kardashian had to come out and make a, a statement about, um, all of, all of the anti semitic comments. Uh, then Adidas, Adidas ultimately, uh, publicly came out and, and cut ties as well. He went on Lex Friedman's podcast, um, and talked about some of this stuff as, as well. But, um, yeah, it's, it's sad. The whole thing

• 4:11Logan Bartlett?

  is like super sad. Um, obviously what he's saying is deplorable, right? Uh, and I, someone with that platform saying the things he's saying is, uh, troubling because he can reach a lot of people and even, um, small numbers of people that he can influence, right? Uh, can have catastrophic implications with it.

• 4:35Speaker 01

  I saw that, that poster that folks were holding up on the bridge or something that was like, we support what Kanye says about white lives matter. I don't know if Justin, you can pull it up, but like, yeah. Obviously, yeah, troubling.

• 4:48Logan Bartlett?

  Yeah, and then, so the antisemitism is just like, I mean, it's deplorable, it's disgusting, like, it doesn't have any place in the world, it's, um, yeah, uh, and then it's also, and so everything that's happening, I think he deserves, uh, like, all the sponsorship cuts and, and all of that, and so, um, I, I think he's getting what, what's coming to him in that regard, but then, it's also sad to see someone that, uh, clearly has mental health issues, right, and has been open about being bipolar and manic, I think, uh, as well, um, just clearly going through, I, I think, I don't want to speculate, uh, overly, I certainly am not, um, qualified for this, but someone that's clearly going through

• 5:32Logan Bartlett?

  something, right, and, uh, with a history of mental health issues, um, and, so that's a shame, and then it's a bummer, people are giving him a platform to, to talk about all these things, right, it sort of feels inappropriate, and then, at, at a personal level, like, I'm just, um, he was one of the people I grew up, like, he, probably the concert, I, I've probably been to more Kanye West concerts than any other artist, right, and I have more, like, pop art and, uh, just random, like, you know, tickets from concerts, and, and so in some ways, it's almost like, I, I, I'm almost mourning the loss of, like, uh, and, and it's been happening over time, right, like, some of the MAGA stuff, and, uh, you

• 6:15Logan Bartlett?

  know, this has been trending in some direction for a little while now, but it feels like, uh, this is like, the, the biggest culmination of it all, and so, it, it's almost like, uh, someone that you don't, that you looked up to is dying, or has died, right, it's like, the, the character of this person that I've been following since I was, like, uh, in middle school, right, um, is no longer the person I thought it was, and I remember going to, uh, the Watch the Throne Tour, I think I went to three shows, My Beautiful Dark Tissus Fantasy, I went to three shows, uh, Yeezus, I went to three shows, uh, Life of Pablo, I went to three shows, Graduation, I went to two, so, like, all these different tours, I went to so many shows.

• 6:56Logan Bartlett?

  It was one of those things, I think, at Life of Pablo, I remember going to the show and being like, gosh, this is such a moment in time where I'm seeing greatness. Maybe it was My Beautiful Dark Twisted Fantasy, but I'm seeing greatness in a moment and I should appreciate this. But then he just kept producing more and more content. And so it seemed like he was just going to keep going, right? And then, yeah, I mean, you sort of have to appreciate these people when they're at the peak of their powers and doing what they're doing.

• 7:26Speaker 01

  Yeah, his music took a weird turn at some point, the Poop Diddy Scoop release, whatever that was.

• 7:33Logan Bartlett?

  Yeah, you could see it kind of go like, I absolutely, I mean, My Beautiful Dark Twisted Fantasy is one of my all time favorites. And then Yeezus, I think, might be the best of his albums. And then after that, you know, Life of Pablo was very, very good, probably not quite at that level. And then, and then he came out with, what was it, Yay? Or the one that he, it was in front of the mountain that he filmed in Jackson Hole or whatever it was. And like, that was not very good, but there were still a handful of songs that you're like, oh, okay, I see this. And then just totally after that, it was like, all right, this is gone, right? So, I don't know, I, I, I, it's, it's, it's just sad. I don't even, it's terrible, it's sad, it's all that stuff.

• 8:16Speaker 01

  I never followed him that, that closely, but I remember we were at a bar in the East Village the other day. And you forget sometimes how many bangers he's got, like the DJ was playing Kanye songs for, I think, like 15 consecutive minutes, maybe 20 minutes, like back to back to back, little one minute snippets. And the whole place was just going crazy the whole time. Everyone's rapping the lyrics like to the word. It's, he's a special artist.

• 8:42Logan Bartlett?

  Yeah. And so I, I, I hope he gets the help he needs. I mean, I've, I've certainly appreciated as, as someone that, you know, has had people in their family with different levels of mental illness. Have, have had different bouts of depression myself over time. Like, I certainly appreciated him being public about all this stuff. And, but now it sort of feels like we're at the point of him just needing help, right? Him just needing to like. And hopefully the people around, hopefully he has a group of people around him that can like rein him in a little bit, or whenever this manic episode or whatever it is passes

• 9:24Logan Bartlett?

  by, hopefully, yeah, hopefully he'll, he'll get the treatment and support and medication and all that stuff that he needs.

• 9:32Speaker 01

  So I guess in, in other news, um, we've covered Elon and the Twitter story quite a bit on this podcast. That seems like it's coming to a conclusion, although every time we think it is, maybe it's not, but I saw the sync video and so.

• 9:48Logan Bartlett?

  Well, it's coming to a new, new chapter, right? Like now he, the, the, the acquisition story is coming to a conclusion, right? Uh, the actual, uh, the actual side of what's gonna happen is like just getting going, right? Like, uh, this is, this is, I don't know, this is probably the first third of the book when it gets written, right?

• 10:12Speaker 01

  Yeah.

• 10:12Logan Bartlett?

  We still have the other two thirds of what the fuck's actually gonna happen.

• 10:15Speaker 01

  Do you think he's serious about laying off, what was it, like 75% of the workforce?

• 10:21Logan Bartlett?

  I don't know. It's hilarious that he's like walking in with smiles and like, you know, I saw something the CMO was encouraging people to go over and like say hi to Elon, uh, the CMO of Twitter. And it's like, yeah, yeah, that guy that just like casually joked about laying off, you know, three quarters of you. Go, go say what's up.

• 10:37Speaker 01

  The issue with that statement is you don't know which 75%. It's not like he was like, I'm gonna lay off this 75%. And so the other 25% could feel comfort. When you say it's with 75%, 100% of the workforce is probably paranoid.

• 10:51Logan Bartlett?

  Oh, yeah, yeah, for sure. Yeah. I mean, 100% of people are like, yeah, I bet if you went, LinkedIn probably has amazing data, but if you went and like saw who has pristine LinkedIn profiles from people on Twitter, it's gonna be a very high number. Like every person that has a job, to have a job at Twitter is to have a very good and up to date LinkedIn profile right now. Uh, and so I think, I think 100% of the people there are, are at least prepared for this. I, I wouldn't be surprised. I mean, we've talked about content and all that, like this. This could have a full-time podcast. Tesla has a full-time podcast that ranks pretty high and Twitter now under Elon probably should have at least a weekly podcast dedicated to all the machinations of what's going on and the news of it. I mean, certainly a

• 11:32Logan Bartlett?

  big enough platform to support it and there's going to be enough news going on here with some of the stuff that they're doing, right? And then if I were a reporter, there's certainly going to be enough people with incentive to leak information here and tell you like Clean's house, right? So yeah, I never thought we would end up at this point when it first got going. And then I only thought we would end up at this point over the last like six weeks. And so it's interesting to see us actually like get to the finish line on all this. And it seems like the banks are all going to commit. I guess Elon's a good enough client for them that they're going to just take the loss and figure it out. All the equity

• 12:16Logan Bartlett?

  partners seem like they're going to commit. I know Sequoia's come through and said they were going to. I think Andreessen Horowitz has. I think the Binance CEO was indicating that he was going to as well. So feels like they're going to be able to like

• 12:30Speaker 01

  Larry Ellison?

• 12:31Logan Bartlett?

  I haven't heard if Ellison's going to do it. But at this point, it seems like enough people. I don't know. I mean, we're recording this on Thursday midday, right? And it's supposed to close tomorrow afternoon. And so my assumption is with 99.99999% like tomorrow afternoon, it's going to be done. So

• 12:49Speaker 01

  Well, it's been interesting to follow along all the leaked tweets and the stories and it'll be it'll be cool to see what happens next.

• 12:57Logan Bartlett?

  Yeah, never a shortage of content or information. So at some point, we might get tired of talking about it, but never a shortage of stuff going on there.

• 13:07Speaker 01

  Yeah, the Larry Ellison exchange that got me was when he was like, Again, I don't know much about how these things actually work, but he was asking for money, essentially from his rich friends. And then he reaches out to Larry Ellison and he's like, "Hey, it's oversubscribed. I need to kick some people out. How many, how much do you want to go in for?" And Larry Ellison is like, "A billion or whatever. Trust you." Like said something to that. In fact, I probably got it wrong, but like, just casually like, "Yeah, like a billion or whatever." Whatever you need.

• 13:39Logan Bartlett?

  What's a billion among friends, right? Anyway, so, yeah. Well, never a dull moment around there. So, uh, yeah, well, uh, everyone's gonna, I think, enjoy this episode with Jason Calacanis. Thank you to him for coming on. And, uh, yeah, look forward to hearing it now. Jake Al, how you doing?

• 14:00Speaker 02

  I'm good. I'm good.

• 14:01Logan Bartlett?

  Thanks for doing this.

• 14:02Speaker 02

  Oh, my pleasure. Long overdue. Long overdue. Big fan of the pod.

• 14:05Logan Bartlett?

  A long overdue. You would think, you would think, uh, I would have like my list of questions already and, uh, given how long I bugged you to do this, but I have a feeling the amount of, uh, the amount of overlap we have and the amount of stuff we can, we can talk about. We might need to shoot from the hip a little bit here.

• 14:24Speaker 02

  I think, uh, I'm qualified to do that. And it seems like you're very qualified to do that as well.

• 14:31Logan Bartlett?

  Marginally so. Where in the world are you?

• 14:33Speaker 02

  Uh, I, I live in, uh, the Bay Area.

• 14:36Logan Bartlett?

  Yeah, yeah. I know it.

• 14:37Speaker 02

  Yeah, it's quite nice. It's like, uh, I lived in the city for a couple of years. I lived in LA for 10 years and then before that, Brooklyn and New York City. Where are you?

• 14:44Logan Bartlett?

  I am actually in our San Francisco office on Maiden Lane, which is why you're seeing this interesting wallpaper. Uh, normally I'm not set up, uh, like this, but, uh, yeah. And then I, I'm, I'm on the Lower East Side. So I, uh, we can, we can rap New York. I would love to hear at some point.

• 15:00Speaker 02

  You got a lot of New York stories. Good ones, too.

• 15:02Logan Bartlett?

  Yeah, I mean, we can dive right into it. You were at the peak of the original Silicon Alley, right? Back in the day.

• 15:08Speaker 02

  Yeah.

• 15:09Logan Bartlett?

  And now it feels like there's a energy right now, uh, that, I don't know. I don't know what it was like back then, but have you been back to New York recently?

• 15:19Speaker 02

  I come back a couple of times a year. My family's all there. Uh, in the nineties, New York City was awesome because you had a number of different, uh, industries emerge.

• 15:33Speaker 02

  CD-ROMs, online services, eventually the internet, media, and really the startup culture of the day was something called zines.

• 15:40Logan Bartlett?

  Oh, yeah.

• 15:41Speaker 02

  Which was short for magazines.

• 15:42Logan Bartlett?

  Magazines.

• 15:43Speaker 02

  And so I had started two zines in my, when I was 22 and 24. And the second one, the first one was called Cyber Surfer, and that was about online services. This is before the internet, before the web browser really existed. And then I did a magazine called Silicon Valley Reporter, which started as a 16-page photocopy newsletter, and then eventually grew to a 300-page glossy, going out to 100,000 people with 12 million a year in revenue and 100 employees, and did that all on my credit cards. And I did New York to a degree that was, you know, intense. I was on Charlie Rose and the cover of the New York Times, you know, had a New Yorker feature, you know, like, I did it.

• 16:27Logan Bartlett?

  What was the cover? I mean, you've had, you've had like, how many different acts have you had at this point of like, being famous for different things? Because, I mean, that was you and Marc Andreessen being barefoot on the cover of Time. I feel like that was the, you know, that was the original internet back then. So what was the context of being on the New York Times?

• 16:46Speaker 02

  They basically did a story about a conf, they did, I was on twice in the early days of the internet. And one was for a conference I did called Ready, Set, Pitch. And so in 1996, I had Ted Leonsis from AOL come to a loft that my friend Josh Harris had for a company called pseudo.com, which was an online radio.

• 17:04Logan Bartlett?

  Is this Josh Harris of Apollo?

• 17:06Speaker 02

  Josh Harris of We Live in Public, which was a, an art project he did. You know, the internet and like Andy Warhol's factory and all that kind of converged in Lower Manhattan, a house and street and like Broadway. And on 600 Broadway, a guy named Josh Harris, who had created Jupiter Communications, which was Jupiter Research, it was like a research company, started something called pseudo-online radio. And he started a radio network on the internet. Now, this is during the dial-up era, but he had done something very interesting. He, he had online chat rooms on Prodigy. This is when Prodigy was maybe five bucks an hour. And then he rented Time on WEVD over on Esther Place. And I would go on, and he would have me read the top 10 websites on the internet.

• 17:51Speaker 02

  And it was Cyber Surfer's top 10 websites. I was completely nervous, like, and I would be reading out a URL, you know, this is like harvard.edu slash tilde, you know, L Barrett, you know, blah, blah, blah, uh, Marlet, da, da, da, da. And I would be giving these long URLs and just talking about the internet. And that was like a very special time because nobody was doing it for money. It was all because we thought it was fascinating. We wanted to see what web browsers and online services could do. Of course broadband happened, money happened and all that stuff. But I had done this like very interesting event where I had seven people pitch companies to Microsoft AOL, et cetera. And so that's when I realized like I was really interested in media.

• 18:32Logan Bartlett?

  Did you fall into that? Uh, because I mean, you, uh, you grew up in New York. Once upon a time you were going to go be a police officer. And so like, how did you go from police officer to New York Times? Can you link those two things together?

• 18:47Speaker 02

  Yeah, I think some people in the industry would have preferred if I had become a cop.

• 18:51Logan Bartlett?

  You know, I mean, there's still time.

• 18:53Speaker 02

  There's still time. Uh, well, what happened was I, I grew up in Brooklyn. My dad owned a bar and was a bartender and my mom was a nurse. And, uh, I, uh, was going to school at night at Fordham University at Lincoln Center, but I, I couldn't afford to pay for it because my dad, uh, through a series of events, had his bar seized from him during the 1987 market crash because he couldn't pay his bills. And then he got in arrears for tax debt. And so he said to me in my senior year of high school, hey, listen, I'm sorry. I got no cash. I'm probably going to jail, um, or might be going to jail. Take care of your mom and, uh, good luck in college, son. And so this is six weeks before the semester started. So instead of going to Fordham during the day, I went at night. And then I fixed laser printers during the day.

• 19:36Speaker 02

  But when I would take the train into Manhattan over the Manhattan Bridge, I'd take the B train, uh, from Bear Ridge, the R train to the B train, I would, uh, always see people reading magazines. And then I wondered like, how do people get on the cover of a magazine? And then I looked at the masthead and I was like, what's an editor in chief? What's a publisher? What's an editor at large? I kind of became obsessed with it.

• 19:55Logan Bartlett?

  What year is this?

• 19:56Speaker 02

  This is 1992, 93. And I was going to school at night, like I said, and fixing laser printers. And then the internet happened and I, through a series of events, having worked at Fordham's computer room, I had been on BitNet and ARPANET and, you know, all the precursors to the commercial internet. So I had just seen like the send command and gopher and news groups and all this stuff. And then the browser happened and it was like, well, this is interesting. And the browser didn't even support images. Long story short, I started this magazine, this zine called Cyber Surfer. That lasted five issues and then I started this Silicon Valley reporter because I had a couple of friends who were starting internet companies and I had met a guy named Jerry Colonna, who's partners with a guy named Fred Wilson.

• 20:39Speaker 02

  And they were starting Acme Ventures and they had me reading business plans for them while I was doing the zine. And I read like the business plan for Beverly Hills internet, which became GeoCities, which was a big hit for them. And I had a choice to either go venture or keep doing my magazine. I chose the magazine, probably not the most economically sound thing to do. I could have been a VC, maybe at 23 or 24. But I loved it. I loved being in media and I, and I built that company.

• 21:03Logan Bartlett?

  Being tied to Fred Wilson, I think, I think that would have worked out and Jerry as well, I guess, but I, I think that would have worked out for you.

• 21:08Speaker 02

  Could have been okay.

• 21:09Logan Bartlett?

  All roads lead back to VC eventually.

• 21:11Speaker 02

  Yeah, basically.

• 21:12Logan Bartlett?

  I'm fascinated by that moment in time. Did you know like this was actually something uniquely special? I guess it's hard to have sort of historical context when you're whatever, 22, 23, 24. You knew that it was something.

• 21:22Speaker 02

  Absolutely.

• 21:22Logan Bartlett?

  Do you, do you equate it to, I mean, people always draw the analogy to Bitcoin and crypto today, like actually trying to be as prescriptive about those two things. Does it, does that actually feel similar? Does that fall apart when you actually think about it from your perspective?

• 21:35Speaker 02

  If we're talking about like the early days of Bitcoin, when nobody cared about money, there were no ICOs, there was no grifting or, you know, bag holding.

• 21:42Logan Bartlett?

  Yeah, 10 years ago.

• 21:43Speaker 02

  Yeah, yeah, 10 years ago, sure. It felt like people were tinkering with a technology to just see what it could do. Of course, everything gets corrupted by money. And so, you know, the fact that, you know, if the browser had money built into it, of course, you know, and securities built into it, you, you could have had the internet get corrupted in that 1.0 era, but it did get corrupted by, you know, these IPOs of companies that had no revenue. So in that way, it was very analogous that a bunch of grifters came in, IPO'd a bunch of, you know, bad products and then you had the dot com bust. So that, that arc was correct in the same way crypto is. Of course. You know, crypto hasn't really proven much value outside of, and I know it's a reoccurring theme here on cartoon avatars.

• 22:25Speaker 02

  But crypto needs to prove some use case and value other than I can sell 100 million in tokens to the retail investors and pretend it's not a security while I cash out.

• 22:35Logan Bartlett?

  Yeah.

• 22:35Speaker 02

  Not that I have strong feelings on it.

• 22:37Logan Bartlett?

  Yeah, yeah, exactly. No, that's one of the things that, I mean, the use cases, if you go back and look, like, people could at least project what the exact use cases seem to have been. If you go read probably your zine back in the day for the internet, right?

• 22:51Speaker 02

  Community is what we used to call it. And then social media became what community was. So we just envisioned community as message boards or virtual spaces like something called the palace, which was like 2D avatars walking around with little bubble chat bubbles over their head or virtual places. So we saw community, we saw social networking early, we saw e-commerce early.

• 23:10Logan Bartlett?

  That was the metaverse back then, those little bubbles over your head. Gosh.

• 23:13Speaker 02

  So much better than sucks.

• 23:15Logan Bartlett?

  Yeah, I know. History rhymes altogether. Comes back around on all that stuff. Now, what was the path into media? Did you have some innate, I mean, I guess VC was such a cottage industry at that point, and especially doing into New York, probably felt a little unusual. But was there some gravitational pull that existed there? Do you feel like it was more natural to you?

• 23:34Speaker 02

  I knew nothing about it. I'm self-taught. And so I taught myself how to do page maker to lay stuff out. I taught myself how to write. I taught myself how to take pictures. And it really informed me as an entrepreneur and enforced my investing as an entrepreneur. I think a big part of being an entrepreneur is being fearless about adding skills and being able to break down what skills it takes to build a product. And in that case, a magazine took writing, it took selling ads, it took taking pictures and laying its stuff out, and then eventually distribution. And so I just tried to master all of those things. And I did it over, you know, six or seven years. And none of them were too hard. And I believe you can get to 60 or 70% proficiency in any Discipline, if you just put your mind to it. That doesn't mean you're going to become

• 24:18Speaker 02

  great at it, but you only really need 60, 70% to be able to figure out who has the 80 or 90% that you could hire. And so I did everything in the first couple of issues when it was a zine, quickly learned it. And most of all, just learned the power of media, exactly how media can make you very powerful and influential very quickly. Because I went from being an outsider and a nobody to having all the Harvard, HBS kids who were raising venture capital and who wanted to be on the cover of the magazine, you know, basically trying to lobby us to get into the magazine. And it was quite deliberate in that I created something called the Silicon Alley 100. And I was like, oh, okay, these folks don't accept me. I'm just going to rank them. So I'm going to create that Silicon Alley 100.

• 25:02Speaker 02

  And people were like, okay, create the 100. And then I told my team, okay, now tell me who's number one, who's number two. And like, we shouldn't rank, it's too divisive and people are going to be really upset. And I was like, great, let's start the ranking process. And I basically just, you know, put everybody in their place by taking the number one company, which was DoubleClick. That was the consensus pick because they'd raised the most money. And then I put Esther Dyson as number one, who had kind of led the industry before DoubleClick even was there. And I said, this is going to make everybody lose their mind. Because they would say, how is one angel investor more important than DoubleClick, the most important company? And I just came up with a justification. She was here before them, and she set the stage, and she laid the foundation. And then I learned that lists are completely not important, and they're made just to tweak people. So

• 25:47Speaker 02

  when founders I invested now are like, can you write my recommendation to get on the 30 under 30, 40 under 40, 50 over 50, whatever bullshit. I'm just like, sure. It's meaningless. Get back to work. None of this matters.

• 26:00Logan Bartlett?

  So you did all that. You sold, do you sell a company to AOL?

• 26:02Speaker 02

  So after that, I did a company called Weblogs Inc. So after Silicon Alley crashed and burned, I sold the company to Dow Jones. I got two years of salary. And then I watched blogging occur because two of my employees had gone on to do blogs. Shani Jordan worked for Silicon Alley Reporter doing events, and then she did Boing Boing. And then Rafat Ali went and did paid content. And I thought, these blogs are stupid. Like, there's no editor. There's no office. You're just doing this at home in your underwear. But then I found out they were making like 10 grand a month each off of the advertising. And I was like, well, that's more than I paid them. And they own these properties. Blogs are going to be a thing. And I had an acquaintance named Nick Denton, who had started a blog called Gocker.

• 26:45Logan Bartlett?

  Yeah, he's made news for himself since then.

• 26:47Speaker 02

  Yeah. And I was like, Hey, Nick, can I talk to you about blogs? I want to start business to business blogs. And I started business to business blogs.

• 26:53Logan Bartlett?

  When was this?

• 26:54Speaker 02

  Uh, this 2003, maybe.

• 26:56Logan Bartlett?

  Okay.

• 26:56Speaker 02

  Uh, time period, you know, right after the dot com bust, nine 11, and New York was a pretty dark place. Uh, you know, it's really like a trial in the industry. It's actually kind of starting to feel like that to me now, where people are giving up and throwing in their, throwing the cards and kind of giving up. But I mean, it was everybody in the industry gave up, like 98, I mentioned 98% of people just stopping doing any entrepreneurial stuff. That's what happened after the dot com bust, which is distinctly different than now. But it's, it's similar in some ways to the way people feel like this will never come back. But what was interesting about that time was, you know, we, we had a discussion about it. And then he wrote like, some blog post that I was like, gonna be the worst thing that ever happened to blogs, because I'm going to commercialize them and put advertising on them. Now, that was a very controversial thing to do, to build multiple blogs. And

• 27:41Speaker 02

  I said, Well, I'm going to be like a B to B publisher. I'll do like 100 of them. I told him, I think I can do like 100 of these in all these different niches. And so I was like, oh, so Nick attacked me publicly. And so then I just, yeah.

• 27:53Logan Bartlett?

  So you had a private conversation with Denton, and then he?

• 27:57Speaker 02

  He wrote a blog post.

• 27:58Logan Bartlett?

  Attacked me, published?

• 27:59Speaker 02

  Yeah.

• 28:00Logan Bartlett?

  Gosh, man, that guy.

• 28:02Speaker 02

  Yeah. Nick is sharp, Nick is sharp elbow, but I appreciate that about him. We remain frenemies. I really think like as publisher to publisher, he's extraordinarily talented. But yeah, that was a, that was a like, you know, you're walking out of the restaurant and the person just hits you with the bat in the back, you know, like you get jumped in the alley kind of situation.

• 28:19Logan Bartlett?

  Yes.

• 28:20Speaker 02

  So I was like, okay.

• 28:21Logan Bartlett?

  For people that don't know, Nick Denton founded Gocker and was ultimately bankrupted from Gocker because of, I guess, a serendipitous set of events.

• 28:33Speaker 02

  Peter Thiel.

• 28:33Logan Bartlett?

  That involved Peter Thiel and Hulk Hogan and Bubba the Love Sponge as well, and

• 28:38Speaker 02

  And a sex tape. Everything. I was pretty.

• 28:40Logan Bartlett?

  Sex tape and it makes her a great story.

• 28:42Speaker 02

  Pretty extraordinary. It would make for a great season of secession.

• 28:46Logan Bartlett?

  That's right. Yeah, I think that's coming. Bubba the Love Sponge is season five. So, so that that's fascinating. So you started doing B to B blogs and what is B to B blogs? I mean, I realize this is hard to contextualize today. Blogs even sounds like such a dated term.

• 29:00Speaker 02

  Well, blogs at the time were personal web logs. So it meant a webpage with a log file on it. So you'd make a web log. So I called, we called it Web Logs Inc. And we started one on wifi, this new technology that people were installing. So we did wifi dot weblogsinc. We did apple dot weblogsinc. So I said, these subdomains would be a cool way to do it. I was very influenced by about.com. That's Scott Kernan had created and became a very large website in web 1.0. So I started building these and then I was like, you know, I gotta get my revenge on Nick Denton. And so I tried to hire Elizabeth Spears or Spires, who was running Gawker. And so I said, hey, can I buy you a drink?

• 29:41Speaker 02

  And I said, I know he's paying you like two grand a month. He said, no, more like a thousand or something. And I said, okay, I'll pay you two grand and I'll buy you a MacBook Air because the MacBook Air had just come out or something. And she's like, yeah, no, I'm gonna go work for New York Magazine. I was like, hey, listen, kid, like you're in blogs. That's the future. You're gonna go work at New York Magazine. You'll be like the 150th most important person. She was still enamored with magazines. So she went and she had left Gawker for that. And then a friend of mine said, hey, you know, you picked the wrong target. All the money at Gawker is being made by their second blog. I said, what's the second blog? I didn't know the second blog. They said it's called Gizmodo. I said, okay, who's running that? They said Peter Rojas. I said, okay, can you introduce me? You introduce me. I take Peter out to dinner at Jewel Baku, a famous little sushi place on the Lower East Side back in the day.

• 30:26Speaker 02

  And I said, I'll pay you double. I'll give you the MacBook Air. Come work for me. I'll give you equity. He said, yeah, Nick said he would give me equity. He never gave me equity.

• 30:34Logan Bartlett?

  Yep.

• 30:34Speaker 02

  So anyway, I hired Peter Rojas and we created Engadget, which became much larger, like 10 times larger than Gizmodo. And Peter, when we sold that, Mark Cuban was my only investor in the company. And when we sold the company, Peter made millions of bucks and my partner and I, Brian, made millions of bucks. And that was my first big win that I got on the board. And yeah, that was my second act, I guess, as it were, after Silicon Valley butter.

• 31:00Logan Bartlett?

  When did you sell it?

• 31:01Speaker 02

  2006, maybe? We sold it for 30 billion bucks 18 months after we started it AOL, which to Ted Leonsis and Jim Bankoff. Jim Bankoff was like Ted Leonsis' right-hand man. Then Jim Bankoff took the team from Engadget, etc., and the playbook and did Vox and Verge and bought a bunch of blog assets that are now Vox. And so, he made me my first money, and then he took the playbook and built and even picked the company now.

• 31:28Logan Bartlett?

  Yeah.

• 31:29Speaker 02

  With the Verge and everything else.

• 31:30Logan Bartlett?

  Were you quasi, what's the new term now? I think Taylor Lorenz termed it like niche internet micro, NIMBY or whatever, niche internet micro influencer?

• 31:43Speaker 02

  Celebrity?

• 31:43Logan Bartlett?

  Yeah.

• 31:44Speaker 02

  You know, before influencer, sure, yeah. I mean, in New York, I was known for the magazine. If you had a magazine, that would be the equivalent in the 90s of being an influencer, right? But also entrepreneur. So it was like kind of having a startup and being an influencer. Blogs were the equivalent of that in Web 2.0, as we called it. And then today, probably podcasting is the third part.

• 32:05Logan Bartlett?

  Did you call it Web 2.0 at the time?

• 32:07Speaker 02

  Yeah, yeah, everybody called it Web 2.0, yeah. And it was a good moniker, because the web became more advanced, like Ajax and refreshing of webpages, and cloud computing started to happen. So building websites, as you know from the history of venture, we went from having to rack and stack servers, and if you raised money, you spent your first half million or million on an office, and another half million or million on servers, to I can get an office share and a green desk or whatever, and just put up a cloud. I could rent space in a co-location facility, which eventually became cloud computing. So yeah, just changed the economics.

• 32:46Logan Bartlett?

  Numbering anything, I mean, it's great. It's smart what the Web 3 guys have done. Like, anything being the next number makes the prior, it's kind of pejorative to the prior one. So it seems like you were on the cutting edge of that way back when. Now, when did the, this week in startups, when did you start podcasting and do it all? Because this was starting to get going. Podcasts really started in earnest, what, 2007?

• 33:11Speaker 02

  I think, actually. And so there's a guy named Dave Weiner in New York who created the RSS standard, which then became the backbone of Twitter and blogging. And Evan Williams, if you remember from Twitter, did blogger.com previously. So we were all kind of hanging out together. And this standard, at some point, he said, Well, we can put an attachment on it. And why would you do that? And so your RSS feed catcher, dedicated software, you had to download the blog posts, and you could read them on planes or when you were offline, could then have an attachment. And then the attachment would then get stored on your hard drive. And then somebody was like, Well, what if you stored it in the iTunes place? And then you had your podcast download the MP3 file. And that connection that people

• 33:53Speaker 02

  made became podcasting. And the term pod comes from the iPod. And there's that famous video of me at the All Things D conference, asking Steve Jobs that you've probably seen that's gone viral a couple of times.

• 34:02Logan Bartlett?

  We could probably splice it in right here as well. It's a great video.

• 34:06Speaker 02

  One other thing, will you be able to add any RSS feed to the or any podcasts RSS feed to iTunes? Or is it only through the store? Oh, you'll be able to add anything you want, completely open. We're just working with the open standards out there. Yeah. And will you help companies like ours sell podcasts, you know, be an audible? So if we wanted to sell a podcast through your service, would you help us do the fulfillment? You know, we're planning on having all the podcasts be free at first. But zing me an email with what you've got in mind, and we're open to anything. Same email I always send it to you? Yep. Okay.

• 34:41Speaker 02

  The funny thing about that is, I did have Steve's email. And I did trade emails with Steve, because Engadget frequently got into hot water with Steve, especially with the iPhone 4 gate, when the antenna gate happened. He was not pleased. So he sent me a couple flame emails. Yeah.

• 34:56Logan Bartlett?

  That's good. Yeah.

• 34:57Speaker 02

  Yeah, funny times.

• 34:58Logan Bartlett?

  I appreciate people that are that rich and powerful, still holding grudges, you know, and being like petty about the slights that journalists take at them. It's something I I hold near and dear to my heart, just when people don't let things go like that.

• 35:11Speaker 02

  He was full contact, you know, who's going to let you know his opinion. And he didn't. Shy away from talking to people. It wasn't like these new CEOs that hide, you know, and then never talk to the press. Like there's, he was just loved talking to the press in a way that most founders just don't want to engage with them. And then, at that time, the press was a little more, you know, collegial with the subjects because tech was like a very niche thing. It was like people who were into iPods and computers were like this small subset. You know, the general public wasn't really into computers. They might use one at work, but it wasn't like today where everybody had a computer in their pocket and it was impacting society and elections and whatever, you know?

• 35:51Logan Bartlett?

  The influence of tech, it was like this, this nerdy sort of cottage industry that maybe you dealt with at work, right? You went, I mean, and to some extent, like Jobs and Gates and Michael Dell, and there are a handful of those like whiz kids that got a ton of coverage, even Andreessen, right? But it wasn't 100%, there wasn't the level of cynicism that there is now, it feels like, where in the last five years, it feels like the tone of assuming best intent has like totally gone out the window. And now it's like assuming worst intent from a lot of news sources about founders and intentions. And, you know, in some cases, rightfully so, I guess.

• 36:29Speaker 02

  In some cases, rightfully so. In some cases, it's just because it's a popular thing to do is to beat up on capitalism or entrepreneurship. In a lot of cases, it's unfair, you know, like, and the percentage of coverage of very cool things being built, you can just look at your portfolio. Whatever company makes a mistake in your portfolio is going to get 100 stories. And then the other 99 companies in your portfolio that do amazing work in the world make no mistakes are going to get zero coverage. And you're going to say to some journalists, hey, would you cover this? And they're like, you know, why would I cover that when I could cover the latest missteps of Uber? You know, like, that's, that's going to get more clicks. And so, you know, the, the press moved from being really interested, and I was a member of the press, just really interested in the innovations. And you still have some real press that do that, but I would

• 37:12Speaker 02

  say by and large, people are very cynical and the, the impact of tech just hits everywhere. And it's, it's just a different world today when you have Tech impacting employment the way it does, elections the way it does, news and the truth, you know, and then really, if you look at it deeply, the press got hollowed out by the tech industry and there is a longstanding grudge there. And most people don't realize that, but having been through it and been on the other side of watching tech do it, watching America Online, you know, take away access to users, then watching Google take away all your advertising, watching Facebook take away all your advertising, eBay and Craigslist take away the marketplace, you know, and as classifieds, you just watched

• 37:56Speaker 02

  your entire business get gutted out. And people will say like, well, that's nonsense. But yeah, I think there's a like in a very intrinsic grudge between the tech industry and what they were able to accomplish and what they did in terms of gutting out the media business. And it still exists to this day.

• 38:11Logan Bartlett?

  You think that's where the resentment resides versus just like the, the power and the money and influence that comes with all these algorithms and, and all the dollars accumulating to a handful of people? Or do you think it's some of both?

• 38:24Speaker 02

  I think that was like the second piece that kind of tweaked people. The first piece was like, hey, these guys just ate our lunch and, you know, Rupert Murdoch's like, why would we index our stuff in Google? And why does Google get to give you these snippets of our stories? And then people don't actually click through? Or why is Apple mitigating our subscriptions and we don't get the subscription information when they sell an app? We don't have the person's contact information. So there's this longstanding kind of who controls the pipes to the customer. And, you know, subscriptions in New York Times, some people have done a good job of maybe mitigating against that eventually.

• 38:56Logan Bartlett?

  Yeah.

• 38:56Speaker 02

  But it's been hollowed out, you know, same thing happened in the music business. And so it took a little while for that equilibrium. And I think that equilibrium is happening right now with Substack and podcasts. I think some of the traditional press still are, you know, if you were to look at the New York Times, probably four out of five stories are extremely negative on tech. And then you look at podcasts, you find a, even the New York Times podcast, you might find in podcasting, a more nuanced, more accurate, I would say, approach, you know, these. Pieces where they attacked the away founder, you remember that one in the New York Times?

• 39:28Logan Bartlett?

  Steph's a friend and I was the first, maybe institutional, if not first actual investor in a way. So I remember it very well.

• 39:38Speaker 02

  Well, I mean, you look at that instance and it's like, okay, she told the customer support team, we need to work hard during Christmas because that's when our customers need us and that's what pays our salary and everybody needs to buck up and work hard. CEO that I've invested in says that, I give them a high five, right? Good job. You read them the rally cry. You tell them, hey, get serious. If you're not serious, get out of here. Like this is why we're here. And then all of a sudden she's a racist. Like they painted her as being a racist or being like a B word, you know, like all these things they do to women. And it's like, this is completely unfair and it's not true. It's obviously not true. You're making this shit up.

• 40:15Logan Bartlett?

  That's one that's like the nearest and dearest, I guess, to me just because I knew her before she started the company. We were just friends in New York when we were like 22, 23 year olds, right? And like, you know, I was in finance. She was working at Warby Parker at the time, right? She ended up marrying a buddy of mine as well. And watching someone go through that was like, that, when you see someone hit like that, just so unnecessarily, it really makes you cynical to the power that other people have, right? And we're seeing these democratization of platforms and distribution of information that have really negative effects when people are debating fundamental truths in some cases,

• 41:00Logan Bartlett?

  right? About elections and whatever. But then how many of these instances, like just careers and lives ruined because of misrepresentation in some way, shape or form by the media, by the press or whatever? So.

• 41:15Speaker 02

  Yeah, it just seemed really unfair. It seemed like a double standard. And it felt like, you know, all these anonymous sources, we weren't in the, in the early days of journalism, you know, and I was coming up, they would be like, yeah, you can't use anonymous sources. You got to get two people on the record, three people on the record. And now it's like, ah, yeah, we got a couple anonymous sources, but they're scared of the ramifications, therefore we can print this. So I think there needs to be some rethinking of this. And then, you know, people are just not going to let themselves be canceled anymore. I think if the away thing happened today, I think maybe the board or, you know, the shareholders around that and the company might stand behind her.

• 41:50Logan Bartlett?

  Yeah.

• 41:50Speaker 02

  And be like, you know what? Who cares what the New York Times says like and you've seen that since like people have tried to do hit pieces on you know different founders and they're like yeah whatever you know

• 42:01Logan Bartlett?

  People just move on yeah

• 42:03Speaker 02

  Just move on it doesn't matter like it's sure okay and even if it was true even if I you know berated five people on my team like you're not doing a good job you guys are idiots which I've done in my career you know earlier my days like this is I've told people like this is terrible work you're gonna ruin the magazine like I literally kicked somebody out of my office I was like go home I'm disgusted by this effort like if I did that today I would probably be a headline story but in the 90s if you told somebody like listen you're this is not the quality of work we expect here you're fired like that's what you expect if you did a bad job so I don't I don't know what's going on with the sort of benchmark of this but that one seemed profoundly unfair and it's it's continued but and when there's a reaction to that which is people now are tuning

• 42:48Speaker 02

  into podcasts to get their information and a lot of the podcasts are by the subjects now I'm unique in that I'm a journalist who turn who was an entrepreneur

• 42:55Logan Bartlett?

  Yeah what do you consider yourself by the way are you investor or journalist?

• 42:59Speaker 02

  Sure whatever you like yeah I mean I was one of the first folks to say like what does it matter like I'm a journalist turned entrepreneur I'm I was an entrepreneur journalist I was an entrepreneur who learned how to be a journalist who did media and then started angel investing so you know pick whatever you want but it's become quite a playbook now from what I understand this media plus investing thing

• 43:18Logan Bartlett?

  Yeah yeah listen I I it's an interesting I mean you were obviously were on the forefront of doing a lot of this stuff and the podcasting thing is interesting where it's still the tools as we've seen from cutting out here once already to give people a little bit of the sausage making the tools are still in their infancy and I've gone back and forth with your nephew Nick about about some of the stuff you guys do and use for all in and this weekend startups and all that and like no one's really packaged it together and like a fully integrated way that's like one and I realize it's a very hard problem especially as video gets introduced as well you know these different files and recording and internet speeds and all that like I don't mean to make it an easy problem but

• 44:02Logan Bartlett?

  I mean, when you were getting going back in the day, you were recording locally on like Skype calls or something, I assume with with people.

• 44:09Speaker 02

  Yeah, we did Skype. It was basically I had a Tricaster. So I invested in a $20,000 media video switcher that they would use at like churches and stuff like that to make videos. And so, yeah, I had done something called Calacanis Cast for like 30 episodes and then changed it to This Week in Startups after being on Leo's This Week in Tech. And I became like a head on that podcast. Well, he was a video show. So before podcasts, there were video shows like Dignation. And after Dignation and This Week in Tech, podcasting came out and people were like, okay, we can put those shows over here. But video was something people didn't really want to do because it added maybe 100 times the complication and 50 times the cost.

• 44:46Logan Bartlett?

  Totally.

• 44:47Speaker 02

  As you quickly learned, you know, the time to get an audio podcast out is like hours. Time to get a video podcast out is like days, depending on how many full-time people you have. So it's getting there, though. I mean, the tools that are out here now, like Restream, or, you know, all of these different tools, they're getting pretty robust, right? And so it's close.

• 45:09Logan Bartlett?

  When did This Week in Startups or Calacanis Cam, which sounds far dirtier than it is?

• 45:14Speaker 02

  No, no, Calacanis Cast.

• 45:16Logan Bartlett?

  Cast. Good. Calacanis Cam sounds like something that I don't want to see. Calacanis Cast sounds great.

• 45:20Speaker 02

  Yeah, I don't think anybody needs to see Calacanis Cam.

• 45:24Logan Bartlett?

  That's our own private, private feed that we have. So, so that was, that was going on.

• 45:30Speaker 02

  Uh, yeah, I think Brian Alvey was the first guest on This Week in Startups.

• 45:34Logan Bartlett?

  In 2000?

• 45:36Speaker 02

  2010.

• 45:37Logan Bartlett?

  Okay.

• 45:37Speaker 02

  2010. So 12 years ago. And it was weekly. And then it went to twice a week, three times a week. And then the last two years, I told my team, if you sell out the ads, I'll do a fourth episode if you get to like three to six months sold out. And I enjoyed doing it so much that I just did a fourth day a week, a fifth day a week, and then a sixth day a week. And then I hired Molly Wood to join me.

• 45:57Logan Bartlett?

  When did Molly, Molly came on? When?

• 45:59Speaker 02

  January 1st of this year.

• 46:00Logan Bartlett?

  Okay.

• 46:00Speaker 02

  Yeah.

• 46:01Logan Bartlett?

  So you were doing once a week, which is where I am right now, which I can only ima- I'm probably 12 years behind you in all of this stuff.

• 46:09Speaker 02

  You're doing great. I listen to most episodes. The crypto ones are a little bit intense.

• 46:14Logan Bartlett?

  Yeah.

• 46:15Speaker 02

  The same one.

• 46:16Logan Bartlett?

  I'm glad you got off the crypto thing. That was getting a little much.

• 46:20Speaker 02

  We jumped off.

• 46:21Logan Bartlett?

  Good move. Good move. It's hard because you get the audience that you create, right? And so if like people are coming for cable news style, crypto dunking and fighting, then that's the group that you're going to have, right? And you can't really switch up off of that. So.

• 46:37Speaker 02

  It was a good move to detour off of it. Yes.

• 46:39Logan Bartlett?

  Yes. Yeah. Well, I was going to blow my brains out. So, yeah.

• 46:43Speaker 02

  Good pivot.

• 46:44Logan Bartlett?

  But so you were doing it once a week and, and then just kept ramping it up. And was it just something that had been a steady growth for you over time and kind of evolving the format? Or how much of a business was it versus your own personal enjoyment?

• 46:59Speaker 02

  Yeah, it was my own personal enjoyment. I had grown up on Charlie Rose and Howard Stern. You know, in the, in the eighties and nineties and they were on every day. And I would listen to Howard and well, he was in the afternoons to start, then the morning on like terrestrial radio. And then eventually went to Sirius and then Charlie was on at night. So I really was obsessing over those two and I liked Mike Wallace and Oprah and some other folks who I thought were really good at interviewing people. And I was like, wow, that'd be a cool job. And then I was on Charlie Rose eventually. I never been on Howard Stern, but.

• 47:29Speaker 02

  And I actually became friends with Charlie and I did a conference with him back in the nineties when he was getting into tech. Yeah, it was kind of cool at the time. It's kind of tragic what happened and horrible. But he was a real institution in New York and I studied them and then I was always like, wow, you know, I, I would have loved to do a radio show every day. Seems like the most fun you could ever have. And sure enough, for me it is. It's not for everybody, but every day I wake up, I can't wait to get on air. I read some stories and then in terms of for my day job, investing in companies. My Lord, is it, as you've learned, you know, people didn't know who you were, maybe a little bit from the comedic Twitter stuff you did. And that was a good start, but I think now people know you from the pod and I've had two or three people say like. You know, hey, this pod's really good.

• 48:12Logan Bartlett?

  Yeah, it's a much more like the depth of getting someone to listen to a pod is obviously a pretty intimate relationship that you're developing with someone, right? Versus looking at 140 characters, you're only able to be one dimensional for the most part, especially if you're fucking around like I was.

• 48:26Speaker 02

  Yeah.

• 48:26Logan Bartlett?

  And so it's, um, yeah, it's definitely had a more holistic element of like getting to know me and the depth of, uh, of relationship.

• 48:35Speaker 02

  I feel you're like almost fully 2D now.

• 48:37Logan Bartlett?

  Yeah, that's good.

• 48:39Speaker 02

  You're almost there to a full avatar. That's all I have at this point, you know, 2.3, you'll be there.

• 48:47Logan Bartlett?

  Being able to hold people their interest and have opinions and be interesting consistently, especially five days a week as you're talking about stuff. I mean, I see people do it all the time on politics and sports. Our world is, it's interesting because you have a leg in both sides of, of this, right? You can bring an investor perspective, you can bring an entrepreneur's perspective, and then you can also be a proverbial talking head about some of these things and you're able to give like a little bit of an inside lens. You're also willing to, uh, mix it up a little bit. I think you got your, um, you got, people got their punches in and you got very comfortable in your own skin, I feel like in the nineties, right? Your first go around of all this stuff.

• 49:30Speaker 02

  Yeah, it's not my, not my first go around. So if somebody gets upset by something I say to the point at which they dunk at me on my own conference and then can't get over it for a year and go on 10 podcasts to talk about it, I'm like, dude, take a deep breath, like, take a deep breath, Palmer.

• 49:48Logan Bartlett?

  Me and, me and Palmer, we, uh, we did not.

• 49:51Speaker 02

  That was a great interview.

• 49:52Logan Bartlett?

  I, thank you. I, uh, I, uh, I did not go the J Cal, uh, route on the, uh, on the interview session just because I, I felt like that there was so much, uh, embroiled in that, that even touching the stove on it felt like.

• 50:05Speaker 02

  Well, no, no, I thought you did a good job of getting him to finally talk about why he was fired, right? And, um, you know, when I had him on the All In stage, uh, which, you know, for people who don't know, he. I had said on my podcast, if we want to rehash it, you know, somebody was like, hey, listen, he backed this thing, you know, that was kind of like shitposting on Reddit and, you know, during the Hillary Clinton-Trump, you know, kind of debates and everything. And I was like, you know, if you're the CEO of a company, it's a really dumb thing to do anonymously. If you're going to do it, you should do it like with your name on it. And if you're not doing it with your name on it, it's kind of dumb because that should tell you, like, you probably shouldn't be doing it.

• 50:41Speaker 03

  He was supporting, like, I don't want to say violent trolling, but extreme trolling would be the way to do it.

• 50:50Speaker 01

  That's right. And his comment about it was really insensitive, kind of that it was, it was almost maybe not super ideologically driven as much as it was like fun for him.

• 51:01Speaker 02

  What an idiot.

• 51:03Speaker 03

  Well, it actually lost, it lost them a fair amount of business. There were about three or four game studios that said, right, we're no longer developing for the Oculus on this one. Because he came out and said basically, well, to overturn a trench to leak, then you need to be able to fund it and, and, and fight back. And you're like, that's not, you're, you're not a revolutionary. This is just HIT posting about politicians. This is not constructive dialogue. This is not an attempt to get, reform the American political scene. This is just, oh, let's be a troll. Yeah. If you want to see like a person's true character, give them a pile of money or a bunch of power, and then you will see.

• 51:36Speaker 02

  And like, think about your family, think about the people who work for you, think about their families. If they find out you're doing this, like, posting or whatever, and you know, it's these kind of dank memes from Reddit, that's going to blow up in your face and it's going to cause your family all these problems. So it's just idiotic. And he really took that personal. And I was like, dude, listen, I, I based this on a story that was in like, you know, 10 newspapers. If they're wrong, I'm totally fine saying I, my commentary on that is wrong. But, you know, he took it real personal. I understand.

• 52:05Speaker 04

  I talked earlier about NPC thinking that prioritizes popularity over principles. What I'm about to do is in very, very bad taste, but I'm going to do it anyway.

• 52:15Speaker 04

  Yeah, we'll see.

• 52:20Speaker 04

  One of the people who I think embodies this type of NPC thinking of going with what's popular and not being willing to ever reverse their position even when they're proven wrong is Jason Calacanis. Let me read about some of the things he's said about me over the years. Just a small sampling. Palmer Lucky, hideous. What an idiot. A moron. This guy Parker Lucky, a complete and utter moron. Jesus, this kid is an idiot.

• 52:54Logan Bartlett?

  I love Palmer as an authentic person and it was one of the more enjoyable conversations I had and we talked a little bit about this offline and it was interesting, I think what he was most, he actually was most upset at the reporting of other people, right? And their willingness to not go back to the source, but you mean it, it wasn't so much as, hey, I have all the facts of how this played out. You were saying a CEO that does this.

• 53:28Speaker 02

  It's an unforced error, right? Like it's not something, you know, you should do as a leader because if it does blow up in your face, the collateral damage is large. Now, I did listen to it and I was like, oh, that's a little spicy, you know, even for me when I said it. And, you know, sometimes you say things are spicy and if it's based on false stuff, you know, of course, like tell me what's wrong. And that's what I did live. I was like, hey, why were you fired and what was the background here? And he didn't want to talk about that. I get it. But I told him, I said, listen, I don't take it personal. Like, you know, you just, the way I said it was a little rough. Okay, fine. I apologize. But tell me what the, what's the real story here, you know? And he's never really, I think he's not legally allowed to talk about the real story if I'm being honest.

• 54:07Logan Bartlett?

  That's right. Although I think I got most of it out of him, which I don't know exactly how those two things worked out. But also I, I think the, the salt in the wound of it that at least what I gathered was that, well, the delay, which I think had nothing to do with this specifically. I think it was just kind of the hype and all the stuff all in was going through at the time, I think. I don't know. I don't want to speak for you. And then, and then, so the delay led to some consternation and then the addendum was like, okay, well, you're going to get the last word here. And then whatever back and forth you guys had made it seem almost like.

• 54:46Logan Bartlett?

  It wasn't the apology that he wanted, right? In all of it.

• 54:49Speaker 02

  Yeah, I mean, I think the apology is, I said it in a very spicy way, sorry. It wasn't meant as personal, it was meant more like, you know, hey, the behavior here, if it is accurate, like, so if I could do it over again, the way I would say it is, if all this is accurate, like.

• 55:05Logan Bartlett?

  Which it wasn't, or at least as far as I know.

• 55:07Speaker 02

  Some percentage of it was accurate, some percentage was not, like, as we just talked about the press. So if I had made this commentary on, let's say, Stephanie, is she the away CEO?

• 55:15Logan Bartlett?

  Yeah, Steph.

• 55:15Speaker 02

  You know, if, if somebody made the commentary on Steph and it turns out was false, which it seems to be, or largely false, or largely over, you know, over dramatized, yeah, you would probably feel bad if you had dunked on her. So I did dunk on him, I apologize for that.

• 55:30Speaker 02

  And, yeah, he probably could have, if he could get a do-over, he would do something different, right? Like, he wouldn't have done it, I don't think.

• 55:36Logan Bartlett?

  I think he said that, actually. So, so either on the podcast or not, he was like, listen, my life is now defined by $9,000, and I don't mean to sound like a rich guy, but like, I always fucking have to talk about these $9,000. And so in the grand scheme of things, would I prefer that my legacy be tied to Oculus or Androld more than this $9,000? Yes, right? So he was very.

• 55:58Speaker 02

  Which was my point, which was my point.

• 56:01Logan Bartlett?

  Which actually brings it back to why.

• 56:04Speaker 02

  I will say this, I am glad he's on our side.

• 56:07Logan Bartlett?

  Oh, my God.

• 56:07Speaker 02

  Thank God he's making weapons for us, because he's supremely talented, like, in the, in the entrepreneurial Hall of Fame, like, I'll barely, you know, be admitted, you know, on the last day, and, and he'll be up there on lights, you know, two unicorn companies, you know, by the time he's 30 years old, I mean, this guy's amazing. And, which is what I told him, I was like, dude, what, what do you care about what I, and I say on my stupid podcast?

• 56:31Logan Bartlett?

  And you know what? He's so, he's authentically himself, and like, allowing that, you know, what he said, thin-skinned, insecure billionaire, he's like, yes, I am. But I will say, it is, it is interesting, the platform that you have with this week in startups now, and also, I mean, All In is just such a beast. In and of itself, right? Every week I look and it's you guys and Lex Friedman on number one, right? Uh, just week after week on tech. And now Lex is having Kanye West on his show, which I uh, kind of disappointing in my, my view.

• 57:10Speaker 02

  I talked about that in the last all in.

• 57:12Logan Bartlett?

  Did you?

• 57:12Speaker 02

  I said like this.

• 57:13Logan Bartlett?

  I missed.

• 57:13Speaker 02

  Yeah, I was like, listen, it's a mistake to platform somebody who's going through mental illness. And I saw Trevor Noah had a similar take, which is if somebody's obviously public about their mental health struggles, says I'm off my meds, which he's apparently he said in a couple of his interviews, and he's acting manic, and he's saying crazy stuff that's very hurtful and could cause, you know, real world harm. This is very dangerous. I get death threats once in a while, you know, every couple of years, somebody jumps the fence and says something crazy. I have to deal with security issues. Uh, it's, it's more polarized now as the number of viewers go up. Can you imagine with like somebody like Kanye West, like if 1% of his audience is suffering from mental illness and/or is racist, right? That seems like a reasonable number. Well, that's a million people. So

• 57:58Speaker 02

  it's a, you know, it's a small percentage. Even if it was point oh, oh, 1%, it would be 10,000 crazy people slash mentally disturbed, like psychotic and/or racist horrible humans, which is two different groups, right?

• 58:10Logan Bartlett?

  Yeah.

• 58:10Speaker 02

  We feel bad for the mentally ill and we could feel no sympathy for the racist pieces of garbage. But he's got them in that audience, law of big numbers. There's 10,000 of them, you know, one of those goes off and, you know, does something horrible. I don't want to say what specifically, but we've all seen bad things happen at places of worship, et cetera. Like he's got blood on his hands. And then for you to platform him, and I understand, I like Lex, and I understand what Lex is trying to do. He's got a relationship with him. So he was trying to stand up to Kanye and talk sense to him. You're not going to talk sense to somebody who's going through a psychotic episode or whatever his episode is that he has. And Kim Kardashian learned that, right? She divorced him and couldn't, had to get off that train, apparently. Um, and it's just really sad. So don't, and I don't blame Lex. Exactly, but I do blame like other folks who maybe like Yeah, I don't know.

• 58:55Speaker 02

  Platform him. It's just really dangerous thing to do.

• 58:58Logan Bartlett?

  I look up to Lex stylistically in a lot of the things he does where he he just has conversations with people and is so thoughtful about like the work he does in advance and coming in and wanting to have like these authentic conversations that they aren't going to have anywhere else. And so I but I was I was bummed. That and I realized the I didn't listen to the entirety of it, so I don't want to speak totally out of school about how it actually played out, but it it's it's unfortunate that that that someone that's clearly going through something is getting that platform to to espouse some of these some of these views. How do you think about your obligation or

• 59:39Logan Bartlett?

  your responsibility with All In Now? Like, as you guys have veered into politi I mean, we talked about the Palmer thing, which obviously had some real world implications for him specifically, but that I assume the listenership of of This Week in Startup, certainly five years ago or six years ago when you were doing it was

• 59:57Speaker 02

  Nothing compared to All In.

• 59:58Logan Bartlett?

  Fraction compared to All In today. How do you feel about your obligation? I mean, to some extent, you're you're shaping some of the discourse, right? Be it within tech, be it within politics, be it within like, do you do you all have an appreciation for that going into each episode? Because it's evolved beyond buddies shooting the shit and just recording it with at least the implications.

• 1:00:20Speaker 02

  Yeah, I think this is not my first time at the rodeo, having, you know, been in the media for a while, but for the other three besties, it's definitely a new thing.

• 1:00:30Speaker 02

  You know, to different to varying degrees, and it has gotten bigger than anybody anticipated. It wasn't supposed to be like, I think last week we're number 26 or 27 on the charts like overall. So that's kind of bonkers. And it really has like with This Week in Startups in San Francisco, I would get asked to take a selfie, you know, if I was out for the day with my kids, you know, once or twice. Now it might be 10 or 20 times. So and if I, you know, it's it's a much bigger number in terms of the reach and

• 1:00:56Speaker 02

  I encourage people when we are talking about markets or startups or venture. Or I'm talking about media. Sure, consider us experts. Sure. You know, we, we have an area of expertise. That expertise is in capital allocation, startup, company formation, technology, markets. Okay, great. And between the three of us, it's over a hundred years, a hundred years of experience in those things. But when it comes to other things, politics, you know, we're probably very similar to a lot of the audience. And there's probably a lot of the audience has more experience than us. But I think one of the things that's interesting is we live in this age of who gets to talk about something. Right? Who gets to have commentary on something? Who gets to talk about whether we wear a mask or don't, whether you take the vaccine or you don't?

• 1:01:37Speaker 02

  Whether, you know, the, the election was rigged or not, you know, like, are we not allowed to discuss these things? Well, I think everybody should discuss these things. And I think what we try to do on the show, I can't speak for them, but for me, I try to have a really healthy dialogue about hard issues. And people are going to have strong feelings about different ones. And David and I, David Sacks, you know, we, we disagree fundamentally about a lot of things. Yeah. But we're still like very close friends when people think that we're at each other's throat. Like we, our families hang out together, go on vacations together, like we're besties, like for real. But like you might have in your family or friend circle, you might disagree, you know, dramatically over certain things.

• 1:02:20Speaker 02

  And we try to let that play out a little bit on the podcast. And then hopefully people learn that you can disagree and still be friends and maybe make forward progress. But, you know, I've caught lightning in a bottle, you know, a half dozen times in my career. And I can tell you, like, you really don't know, like Silicon Valley Reporter became a hit, Engadget became a hit. This week in startups, All In became hits. But then you don't see the 20 other projects I've done that didn't become hits, right? And so this one's a hit and it's quite, you know, interesting how big it's become. And people get a lot of value. And I, as I said, I, I give you a lot of credit, like. You, you, uh, when you started your podcast, we're like, hey, listen, I, I really admire what,

• 1:03:03Speaker 02

  what this, what these guys have done. And I want to try some podcasting and a lot of people copy the format or, you know, got inspired by it and just never gave it any credit. I was, I told you personally, like, wow, that's incredibly nice of you to, to say such nice things about us and the influence it had on you and your show is different and great, you know?

• 1:03:19Logan Bartlett?

  I mean, listen, I would not have thought about, uh, getting behind a microphone and doing this without you guys having done it, right? And, um, I, I think we wanted to rip off the form factor with different style, uh, and approach and people that were not as established in their career or well off financially or whatever it was. And I'll tell you, I mean, uh, how well you've been able to, as a group, stay together and keep doing this when, when you, you guys don't have to, right?

• 1:03:54Speaker 02

  Yeah.

• 1:03:54Logan Bartlett?

  From a financial standpoint or from a even name recognition standpoint and driving the motivations that each person has individually towards a collective, uh, output that is this. I mean, uh, I've, I've shared this, but to some extent Nikita went to go build his, uh, his app, which is now number one in the app store and it's been, uh, it's been wild to see that. And then with, uh, with Zach, there were, General Catalyst is a bigger firm and they have, uh, some, uh, compliance considerations that made it onerous on me, uh, to just like get the product out every week.

• 1:04:29Speaker 02

  Sure.

• 1:04:29Logan Bartlett?

  But we, we had to evolve the, the format and, uh, it's, it's, that was even with like two people that don't have, or three people that don't have kids and none of us are married and are early in our careers and have every reason to make a name for ourselves, right? Versus what you guys have of all the different egos and personalities and dollars and, uh, families and incentives that like keeping everyone rowing in the same, in any direction, let alone the same direction is, uh, yeah, I know it's not been easy along the way, but it's impressive.

• 1:05:06Speaker 02

  It's, you know, when you look at the four individuals, none of us have had a boss. In some cases in our entire career, certainly for me in my entire career, I only had one boss.

• 1:05:15Logan Bartlett?

  By the way, that's the best quadrant is, is people that have opinions and don't have bosses. That's like what I look for, for someone that I want to talk to. It's, they, they, they have stuff to say and don't care who hears it, right? And

• 1:05:29Speaker 02

  They don't answer to anybody, right?

• 1:05:30Logan Bartlett?

  Yeah, it's a great, great quadrant to be in.

• 1:05:32Speaker 02

  It's also a dangerous one to be in, you know, and it has caused downstream effects, I think for all of us in, in negative ways at times. And then overall very positive. So I'm raising my fourth fund right now. And the only reason I can say that is I did 506C, like the public raising of a fund.

• 1:05:48Logan Bartlett?

  Yeah, yeah, public raising.

• 1:05:49Speaker 02

  And I was like, you know, for my fourth fund, I wonder if I mentioned it on all and if I mentioned it on this week in startups that I'm raising a fund, if I'll meet new LPs. And sure enough, got a lot of, you know, emails from folks and I did a couple of webinars. And the last fund was 44 million and then I had 40 million in commits after doing five hours of webinars. Without ever going on the road and pitching any of my existing LPs or new ones, just doing a couple of webinars. So the impact on our businesses has been extraordinary in that when any of us meet with an LP or a founder, it starts with a discussion about all in.

• 1:06:27Speaker 02

  Whatever the topic we're supposed to discuss, take a pitch from a founder. And then maybe end with a selfie or some more discussion about all in. Or I had one, two founders who said, I'll, uh, we're oversubscribed, but we'll let you in if you can get us two tickets to the all in summit. And I was like, well, the all in summit is sold out. And they're like, yeah, that's why we want you to give us two tickets to it. And we're sold out too. And I said, wow.

• 1:06:51Logan Bartlett?

  Yeah, yeah, it's amazing.

• 1:06:53Speaker 02

  You guys are good. I was like, okay, you get two of my, you, two of my 15 tickets I've been allotted as a bestie, you will get two of them. And I gave two of them tickets and Molly and I got the deal with this company.

• 1:07:04Logan Bartlett?

  No, that's awesome. Yeah.

• 1:07:05Speaker 02

  Pretty happy about.

• 1:07:07Logan Bartlett?

  It's an amazing platform. And I will say, coming in every week, coming up with a list of stuff, and then being willing to talk about those things that you might not be an expert, especially, I mean, Sacks is such a good debater and being the foil to him when he has, you know, an entire political party's oppo research backing him up, like your, your ability to, to debate someone that, that, that has all of that stuff. It's, you know, I mean,

• 1:07:32Speaker 02

  Well, and, you know, with Sacks, it's like, you know, I've had to, you know, being a media guy, you know, and being the point guard of this, I've had to work with each of them on what it means to be on, you know, what I tell them is like, let's play like the Warriors. Let's pass the ball, you know, the basketball team Warriors.

• 1:07:48Logan Bartlett?

  Yeah.

• 1:07:48Speaker 02

  Let's pass the ball. Let's be selfless. And you'll notice in each of their performances, a lot of evolution from the first episodes. And somebody was doing this like all in stats, where they were tracking how many minutes and monologues we each did with like some AI or whatever. And you saw a lot of monologuing. And now you hear Chamath saying, hey, you know, I was really interested in what Freeberg said. I want to build on that. Sacks, I'm curious what you think about this. So you see that crisp passing of the ball. And, you know, I created kind of a science corner for Freeberg, because he would zone out during politics. Sacks would zone out during science. And so, you know, trying to get everybody their touches, has been a new experience for me, because usually I'm either the subject or I'm doing a solo dolo, one on one interview, or doing the news with Molly, you know, two

• 1:08:33Speaker 02

  person game, pick and roll. This is different. And so I based this, and the show's format on the McLaughlin Group, which most people are now too old, too young to remember. But the McLaughlin Group was a Sunday show. We had this very cantankerous guy, McLaughlin, who would kind of mix it up with people who were obviously very smart and friendly, but they could get into it. Right. And so, there's a moment where like getting into it gets too heated, and it kind of takes away from the experience. And then there's a moment where like just enough heat makes it interesting, and progress gets made. But it's been a great joy for me to do it. I can't believe we got to 100. I didn't think it was going to make it to 100, if I'm being honest.

• 1:09:09Logan Bartlett?

  Yeah, listen, I, I think a lot of people didn't for a minute there. I can't believe you came on here to talk about the text messages, Jason. And I uh it's

• 1:09:18Speaker 02

  Yeah, it was just not right now. Just give me a couple of weeks on that one.

• 1:09:23Logan Bartlett?

  What what was the uh what do you think the lightning in the bottle of it is as you think about like what's been successful for obviously you're all you're all independently successful you all have opinions you all uh are have relationships that I think people gravitate to and kind of operate in different corners or domains of expertise um.

• 1:09:44Speaker 02

  What do you think it is? I wonder.

• 1:09:47Logan Bartlett?

  I I think I think there's a uh palace intrigue in tech in general right now uh that I'm trying to tap into to some extent that if you can if you can help people for how influential tech is how rich these executives are meme stocks crypto Elon Dogecoin all this stuff if you can help people demystify some of that I think that there's just big picture there's something there right and people care about that and so I think that was something that you guys hit well and then I think there's also the the billions element of just like hey people are interested in the Kardashians life and this is just there there's elements of being on boats or being on planes or you know different level of cashmere sweaters and stuff

• 1:10:30Logan Bartlett?

  that people tend to enjoy um and then I think there's that element of like opinions no bosses and then I think there was covid as like a big beneficiary uh of you know podcasts and YouTube and people kind of changing their behaviors and habits of listening to things uh so I think those are some of them and then also I think there's probably just this people I I put it in two buckets people want to be it's like edutainment or like entertainment and education is sort of what we talk about and like uh I know you talked about this with the acquired guys as well but you're able to touch on some of that where you make fun

• 1:11:09Logan Bartlett?

  of each other and also uh people walk away feeling like they weren't empty calories that they just got right and so I don't know I feel like there's some petri dish of all that stuff but I'd be interested in what you think.

• 1:11:22Speaker 02

  I think that's what most that what you just uh sort of analyzes what most people say the camaraderie of the four of us and being friends uh and you know the laughs and the bits and the you know uh breaking each other's chops on the margins like well that's kind of funny and and and You know, not mean spirited, but but funny. And yeah, you learn something, obviously, hopefully. And people are probably struggling with some of these issues in their own life. And, you know, trying to understand them like markets or COVID or whatever it is, meme stocks, crypto. And so if we can help people understand the world a little bit better, yeah, that's that's great as well. You know, sometimes I think it's just the exceptional moderation of it.

• 1:12:01Logan Bartlett?

  Yeah. The world. What is it? The world's greatest moderator or the world's?

• 1:12:05Speaker 02

  Well, I just started doing that to Troll Sax's army of bots, because, you know, this big thing like, don't interrupt Sax. And I'm like, well, you know, Sax goes for three minutes. And, you know, he goes into his debate mode. At some point, I've got to like, you know, he gets kind of worked up, as you've seen. And so we came up with a couple of devices. Like, one of them is, you may not see this on camera, but I'm doing this sometimes to Sax, which gets edited out. Or anybody who's going on for a while. But this is like, hey, kind of wrap it up. Like, I have a good sense when somebody's gone on a little bit, and they're running out of steam. And the audience is like, okay, I get it. You know, you don't like Biden, or, you know, you really love, you know, synthetic proteins, whatever.

• 1:12:43Logan Bartlett?

  You and Sax have a safe word together.

• 1:12:45Speaker 02

  Basically.

• 1:12:45Logan Bartlett?

  Yeah, exactly.

• 1:12:46Speaker 02

  So I just, I just, I just twirl my finger like a wrap it up kind of situation. And then I try to pass the ball to another person and get people involved.

• 1:12:53Logan Bartlett?

  Moderating isn't, you know, I had the Sam Lessin, Zach Weinberg thing.

• 1:12:59Speaker 02

  Yeah, that was a hot one.

• 1:13:00Logan Bartlett?

  I kind of forgot my job in, in like, was to be a moderator. And I was just kind of sitting there like being entertained by the whole thing. And I realized.

• 1:13:11Speaker 02

  You forgot. I gotta referee this.

• 1:13:12Logan Bartlett?

  I, so I kind of look like a doofus, because I'm just like, sitting there being like, man, they are really mad at each other, right? And I'm like.

• 1:13:19Speaker 02

  You're like watching Mike Tyson and Holyfield go at it. And you're like, you're supposed to ring the bell, dude. This person's getting pummeled.

• 1:13:26Logan Bartlett?

  I went back and listened, and people are like, I was like, oh, that wasn't, that's, this isn't going to come off well for me. My, my, this is not going to show well. And so I increasingly will listen for your moderation style. It's much easier when it's an interview. Because there's not a need for, it's just, it's just two people. And so stylistically, you don't need to go back and forth in, in the same way. But actually moderating, especially across a bunch of different people, is a very different and skill that, yeah, I've had to learn a little bit.

• 1:14:01Speaker 02

  I was getting brigaded awfully bad by like the MAGA folks and the crypto folks. So I had to like change my Twitter settings to only my people I follow can reply for a little bit. Cause they were being pretty vicious and you know, they think that me asking a question of Saks and saying, hey, so do you think Biden's responsible? For Putin invading? I just want to be clear here. Like you don't think Biden is responsible for Putin invading Ukraine? And he's like, no, no, of course I don't think that. So what I'm trying to do here is actually round out maybe some people's positions at times, but I think the audience sometimes, or at least people who are very fervent on one side or the other, might think I'm taking the other position and I'm like, hey schmuck, like I'm trying to clarify a position that maybe is going to be misinterpreted. So I look at my role as to get the best out of the other besties,

• 1:14:47Speaker 02

  to make sure their positions and what they're saying is crisp and make sure that the audience understands it. And a lot of times I'm asking questions because I want to make sure the audience understands an acronym where I want to make sure.

• 1:14:57Logan Bartlett?

  You have to go up and down to different altitudes, right? And like your listener, you know, you probably have an archetype of person that you think about to some extent of like who's gonna, what level of depth to go to or sophistication on different topics, right? And maybe you don't explicitly think that way, but like you at least know, hey, if we're really in the weeds of this, this thing with Freeburg, like I need to pull him back up a little bit about where this is going to operate. And it's funny, I, I had one the other day that someone got really mad at me. I asked, uh, I asked if, if we thought we were at the end of, uh, of like podcasts and that we were reaching kind of a saturation point of the number of podcasts that can exist out there and like that people actually have time for.

• 1:15:40Speaker 02

  Yeah.

• 1:15:40Logan Bartlett?

  And like, obviously I don't actually believe like, of course, the extent people want to talk is the same as the people extent people want to blog, the same extent as people want to fucking post on TikTok.

• 1:15:49Speaker 02

  You weren't pulling the ladder up behind you and saying, nobody else can join the party. But people will interpret it that way.

• 1:15:55Logan Bartlett?

  People got, they're like.

• 1:15:55Speaker 02

  This is the end.

• 1:15:56Logan Bartlett?

  They're like, you, you think that UGC content has a finite, and I'm like, no, I don't, I don't think that. I was just asking the question to like, get a response. So it is funny how, how in being a moderator or, or being an interviewer, people project onto some of these things for you. So what now, what has, give me the weirdest before we go, what's the weirdest part of all in success now for you? I mean, you've been in the public spotlight for a while now. And so the selfies, I'm sure have gone up.

• 1:16:25Speaker 02

  I love it. I can't take enough selfies. I love the fans. If anybody sees me out in public, you know, even if I'm with my kids, just be normal. Tell me you love the show. We can take a selfie, you know, high fives, whatever. You know, and so I'm kind of built for it. I'm on the Myers-Briggs, like, I took the test twice. I think I was 96 and 100% extroverted. So if I talk to people, I come on your show, I feel great energy for the rest, you know, for the next six hours. So I have no problem with like, the micro celebrity nature of this. And people recognizing me, and as long as everybody's kind of normal. And I think that's one of the problems in Silicon Valley is sometimes people get famous or rich or whatever, and they stop acting normal. So my advice to people is always stay normal. Just be a normal person. Like, you

• 1:17:07Speaker 02

  know, none of us are George Clooney here, or, you know, whatever, Gwyneth Paltrow. So just chill. But it's, it's been great that people have told us, it's helped them have better discussions in their life, and felt them feel, made them feel more informed about the world. So it's very rewarding. There's a great paradox to it that, you know, one of the greatest successes of my careers is this non-commercial, you know, weird thing that I have to share with three other people who have three other opinions of which direction to take it. And we had to have like, sort of a rules of the road. Hey, listen, let's just do the podcast every week. Forget about the summits, forget about the meetups, forget about any brand extensions. We'll just do that one thing.

• 1:17:51Speaker 02

  Let's try to get 100 episodes out, 50 episodes out a year, 100 every two years, whatever it is. And just, you know, do a high quality show. And, you know, it's, it's had a rollover effect on my other businesses. So you can't buy ads on All In, but you can buy ads on this week's startups. Oh, you know, All In's not going to invest in your startup, but you know, Chamath or Sax or I could invest in your startups. And, you know, you can't invest in All In, but you know, you could be an LPMI fund or whatever. So it's had a great impact, otherwise, just, you know, in terms of meeting people, like, some serious people listen to the pod. It's kind of weird. Um, like we'll have senators or like Gwyneth Paltrow wrote about it in her Goop newsletter. Like, it's very weird. Like, it just lands some places. And I was at a party this weekend and

• 1:18:34Speaker 02

  somebody came up to me and people were dancing at a party and I'm dancing with my wife and they're just like, I just wanted to tell you I listen to all that, but I don't want to disturb you while you're on the dance floor. And I was like, disturb me? What are you talking about? You know, like, it's great.

• 1:18:46Logan Bartlett?

  You're like, this turns me on more than dancing does. Like, I, it's dirty talk.

• 1:18:50Speaker 02

  Yeah, it's great. Let's go. So I mean, I love it. And, you know, I feel so grateful for my life. Like I said, as we started the conversation, kid from Brooklyn, you know, who went to night school, didn't go to Stanford, has no business being in venture capital, to be able to invest in 100 companies a year and to do these podcasts every day, to me is a dream come true. And I pinch myself every day. And I'm just trying to squeeze every drop out of this amazing orange that fell in my lap, if I'm being honest.

• 1:19:17Logan Bartlett?

  Well, listen, I, I, I mean, without, I guess I didn't realize that starting or doing podcasts were possible. And I did no advertising, certainly the style of it originally. But like, I, I've, I've turned down all advertising on it because it's like, I, you know, I have my own business that pays pretty well. I don't know if you, you, you, you, you all have heard about this, but venture capital is a pretty good business on its own. And so

• 1:19:43Speaker 02

  It works out. Yeah.

• 1:19:45Logan Bartlett?

  Yeah, it's, it's, it's good.

• 1:19:47Speaker 02

  Has it increased your deal flow, actually? Have you, have you?

• 1:19:49Logan Bartlett?

  Yeah, well, I can't point demonstrably to like, hey, this deal came because of it. My response rate, I joked that like, when I got in the industry 2013, 2014, to, to, to like, 2021, my response rate on emails stayed constant because while I got more senior, the industry got more competitive, right? And so like, there was just more competition to break through the noise. And since I've started doing this, the response rate is demonstrably higher than it is before. And the access is just much higher. And people implicitly associate you with the people that they see you talking to, even in small part, right? And so I'm sure after I had this conversation, someone will be like, oh, can you send this to?

• 1:20:33Logan Bartlett?

  The, you know, Jason on XYZ thing. And I think it just elevates the stature or the perceived stature of, of me as kind of a white liberal arts school, business major, career finance person. Like I, I've, I've, I now am something that's like a little more familiar to people than that. And so, I don't know. I, I, I think it has, but it's hard to say like, this deal wouldn't have happened without it, right?

• 1:21:01Speaker 02

  Well, you know, there's a, there's a big difference in the industry. When you move from having to fight to get into deals, to deals that are oversubscribed, fighting to get you into the deal.

• 1:21:12Logan Bartlett?

  Yes.

• 1:21:13Speaker 02

  Uh, because they perceive some value in it. And I think when you get to year two or three of this, and you're very good at it, by the way, I've listened to most episodes.

• 1:21:19Logan Bartlett?

  Thank you.

• 1:21:20Speaker 02

  Um, and getting better. Actually, I could see you getting better. Um, and I told you like it's, it's, it really is about consistency. If you can do a hundred episodes, like you'll all of a sudden be like, okay, I feel like I can just do this. Like playing basketball, playing poker, it just becomes second nature. Yeah.

• 1:21:35Logan Bartlett?

  It's a fucking slog, man. I will tell you, uh, it is getting through. I said originally, we were gonna do, uh, we were gonna do, uh, a month, then three months, then six months, then now I'm at 12 months. And I think I'm at the point of just plowing ahead now. Uh, but it's, uh, it's been fun and it's been even, even getting episodes out every week, getting people to talk to every week. Uh, you know, all this, all this stuff, just the anxiety around getting something out there is, uh, is, uh, it's definitely added stress to my life, but it's been fun. I've obviously enjoyed it quite a bit and learned a lot from it.

• 1:22:14Logan Bartlett?

  So, um, yeah, I mean, I guess I, I thank you and, uh, and all the other guys for, uh, for showing that, um, you know, white men that are business oriented, finance people actually can have podcasts, uh, after all. Who, who would have thought?

• 1:22:30Speaker 02

  Well, it's been great to be here. Hopefully, maybe I'll come on next year again when you hit your 100th episode.

• 1:22:35Logan Bartlett?

  Listen, I think there's some text messages we need to talk about at some point. So you said we would do it.

• 1:22:41Speaker 02

  Yes, this not right now. Just give me a couple of weeks on that one.

• 1:22:45Logan Bartlett?

  Well, thanks. Thanks for doing this.

• 1:22:47Speaker 02

  Yeah, a couple of weeks.

• 1:22:48Logan Bartlett?

  Last one, Knicks this year, Jason. What do we do? Playoff?

• 1:22:51Speaker 02

  Knicks, 40, 43 wins. We're going to sneak into the playoffs. Yeah, but look for a major trade sometime before the before the trade deadline.

• 1:22:59Logan Bartlett?

  Brunson looks good. Go Knicks. See you, Jason.

• 1:23:02Speaker 02

  My pleasure. Thanks, Logan.

• 1:23:09Logan Bartlett?

  All right. So that will do it for the 39th episode of Cartoon Avatars. Thank you to Jason Calacanis, as well as Rashad and Justin and the whole team that works on this, Cartoon Avatars. Next week, we have a guest that I have long admired, long wanted to have on. This has been on my list since I started doing this, someone that I really look up to and it's a really good conversation. So trust you'll enjoy it and I look forward to seeing everyone next week. Have a good weekend, everyone.