Skip to content
AcquiredAcquired

ACQ Sessions: Jason Calacanis

We kick off ACQ Sessions with the-behind-the-scenes story of All-in, from the world’s greatest moderator himself Jason Calacanis. ACQ Sessions is our new, occasional “MTV Unplugged” version of Acquired: a great IRL guest, a bottle (or two) of wine, and no script. We talk about everything you’d imagine we would over wine with JCal — All-In, bestie relationships, money & politics in Silicon Valley, who his influences and mentors have been (one surprise — the great Fred Wilson of USV!), what motivates him to keep grinding and why, at age 50+ when he could easily be winding down he’s instead speeding up into the most productive phase of his entire career. Pour a beverage yourself, pull up a comfy seat and join us! If you want more Acquired, you can follow our public LP Show feed in the podcast player of your choice (including Spotify!): http://pod.link/acquiredlp Survey! Please take our 2022 Acquired Survey if you have a minute. It'd mean the world to us! http://acquired.fm/survey Sponsors: Thanks to Vanta for being our presenting sponsor for this special episode. Vanta is the leader in automated security compliance – making SOC 2, HIPAA, GDPR, and more a breeze for startups and organizations of all sizes. You might say they’re like the “AWS of security and compliance”! Everyone in the Acquired community can get 10% off using this link: https://bit.ly/acquiredvanta Thank you as well to Brex and to Tiny: https://bit.ly/acquiredbrex https://bit.ly/acquiredtiny Note: Acquired hosts and guests may hold assets discussed in this episode. This podcast is not investment advice, and is intended for informational and entertainment purposes only. You should do your own research and make your own independent decisions when considering any financial transactions.

David RosenthalhostBen GilberthostJason Calacanisguest
Oct 4, 20222h 23mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 0:09

    Intro

    1. DR

      [upbeat music]

  2. 0:09 – 1:19

    Cold open + what “Acquired Sessions” is (unscripted, in-person hang)

    1. DR

      So wait, it was a magazine when you started?

    2. BG

      Magazine, yeah.

    3. JC

      Magazine, that's how I started, yeah.

    4. DR

      You said-

    5. JC

      Magazines was, like, the original platform for-

    6. BG

      Wait, are we star- have we started?

    7. JC

      ... Silicon Alley.

    8. BG

      I guess we've started.

    9. DR

      This is, this is the trick, we've just been recording the whole time.

    10. BG

      We just started, yeah, the whole time. [chuckles]

    11. JC

      Yeah, but that, I don't know-

    12. DR

      Welcome to Acquired Sessions.

    13. BG

      All that stuff that you said beforehand-

    14. JC

      Yeah

    15. BG

      ... that, like, was really juicy, I don't think we should put that in.

    16. JC

      No, definitely not.

    17. BG

      [laughs]

    18. JC

      Definitely not. No, we don't wanna tell people where the bodies are buried. Well, cheers, boys.

    19. DR

      Cheers!

    20. JC

      Here we go. We're... This is the... Is this the first one, or- [glasses clink]

    21. DR

      This is the first-

    22. BG

      First one

    23. DR

      ... in real life.

    24. JC

      Wow, IRL.

    25. DR

      But I think this is our ninth, tenth together, something like that?

    26. JC

      A lot between the two pods, yeah, for sure. Great to know you, boys. [sighs]

    27. BG

      So this is the first Acquired Sessions.

    28. JC

      Acquired Sessions. I feel like I should get out a guitar here and just play some Dylan. [laughs]

    29. BG

      [laughs] This is, this is your baby. What is Acquired Sessions?

    30. DR

      Acquired Sessions is, normally on the show, we are, like, so scripted-

  3. 1:19 – 4:25

    Sponsor: Vanta and the evolution to Trust Reports

    1. BG

      Wait, where do you wanna start? We gotta thank Vanta.

    2. DR

      Oh, yes.

    3. JC

      Oh, Vanta! I'm an investor.

    4. DR

      We're investors, too.

    5. JC

      Well, great. They're an awesome company. Big, uh, supporter of podcasts, so yeah, go Vanta.

    6. BG

      We are huge fans of Vanta and their approach to the whole compliance process, SOC 2, HIPAA, GDPR, and more, and we've got CEO and co-founder Christina Cacioppo back with us today.

    7. DR

      Vanta was already the best place to check the box and get security compliance certified, but now you've just launched Vanta Trust Reports, which take things even further. Tell us about that, and how they can help companies deepen their relationships and trust with their customers and partners over time.

    8. SP

      Really excited about these. So actually, a bit of, uh, not yet told Vanta history, but something like Vanta Trust Reports, honestly, a much worse, much more poorly designed version by yours truly, uh, which I can say that, uh, were launched in the very early days of Vanta, when we wanted to help companies get secure and prove that security, but weren't yet convinced we wanted to or had to go all through the nuances of what a SOC 2 was. So we figured, "Hey, let's just make this report of the best security practices. Let's check companies against those practices all the time, and make this live and updating, visible and transparent. This should help these companies prove their security and grow their business, and it should also help them be more secure, because they've got this report, like, this kind of security status page out in the wild." So 2017, Vanta tried this and found out that no one really knew what a Vanta report was, and everyone wanted a SOC 2. So flash forward to 2022 [laughs] and it's actually really exciting. [laughs]

    9. DR

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

    10. SP

      A little bit, you know? And so honestly, like, lit- I mean, I'm joking, but I'm not. Like, literally the company strategy on that day sort of became, "Okay, use the existing standards to bolster yourself and build something better here." And so this launch of Trust Reports is really exciting. [chuckles] These are companies that, maybe it's before they've gotten a compliance certification, maybe in the process of getting one. For some, actually, it's they already have one, but then rather than keep going through their buyer's process, they're like, "Look, this is just constantly up to date and has all the information you need. You know, take a look at this instead, rather than my, you know, compliance PDF from months ago." So relative to a SOC 2, which is done once a year and kept up to date annually, a Vanta Trust report is kept up to date to the minute, basically, continuously. You always know what the company's practices are. So just really excited to, to get this out into the world and into folks' hands.

    11. BG

      Our thanks to Vanta, the leader in automated security and compliance software. If you are looking to join Vanta's 2,000, nay, 3,000 customers-

    12. DR

      That's right

    13. BG

      ... to get compliance certified in weeks instead of months, you can click the link in the show notes or go to vanta.com/acquired for a 10% discount.

  4. 4:25 – 7:31

    From Brooklyn adversity to computers, hustles, and early technical chops

    1. DR

      Thank you, Vanta. So in the juicy stuff earlier, you mentioned-

    2. JC

      Yeah

    3. DR

      ... Mahalo.

    4. JC

      Yeah.

    5. DR

      I don't re- Is, is that why you started the podcast?

    6. BG

      Could we just keep refer- like, referring to the juicy stuff as-

    7. DR

      Yeah, the juicy stuff

    8. BG

      ... anything that we actually want to say, but- [laughs]

    9. JC

      Yeah, no, we don't wanna talk about that stuff. [laughs]

    10. DR

      Yeah, yeah, yeah.

    11. JC

      Um-

    12. DR

      Is Mahalo why you started-

    13. JC

      Pod

    14. DR

      ... you went from print to print to-

    15. JC

      Well, when I... In the '90s, um, I, you know, I grew up in Brooklyn. Um, my dad had his bar, uh, seized by the feds, because he didn't pay his taxes during the 1987 crash. He became, like, he got behind, and, uh, the feds showed up one day, and this was the maybe six weeks before I was set to go to college. And he said, "Hey, son, I can't help you with college. Good luck. Uh, and, uh, I might be going to jail, so take care of your mom." So he was, like, really behind on his taxes, and, you know, state liquor authority, they kind of take it serious. So feds come, shotguns, the whole thing. They seize the place, they seize everything in it, and, uh, I was like, "Well, I guess I'm going to school at night, and I'm gonna work during the day." And I worked, uh, fixing laser printers, and, uh, that was, like, a really good racket. The HP had just come out, and-

    16. DR

      Were you set to go to college somewhere else?

    17. JC

      Well, that's another story, but I was set to go to Brooklyn College. I'd gotten into that. I had also taken the police exam to be a police officer. So my brother went into the force, and then I said, "You know what? I'm gonna see if I can go to college and make that work, so I'm gonna go to Brooklyn College." So I decided to work during the day, and then I went to school four nights a week, 6:00 to 9:00 PM, carried full credit, 16 credits a semester, and, uh, I would work fixing laser printers all day. I was a bad student. Uh, I was always that student who underperformed.... I didn't find great meaning in academics, but I had a computer when I was in high school, and I was more interested in playing with my 300 baud modem, which then became a 1,200 baud modem and my PC junior. So it kinda, you know, like many people of that era, we were sort of set on a path because we were the first generation to have a computer at home. Uh, I actually had an Atari 2600-

    18. BG

      Wow

    19. JC

      ... and it could play Tank, was the game that came with it, and Pong. And so my dad bought this for us when I was six or seven years old, 1976, 1977, and he had one of the first Pongs in Brooklyn in his bar.

    20. BG

      Oh!

    21. JC

      So-

    22. SP

      He, he must have cleaned up on that.

    23. JC

      Oh, my God, it was crazy. Um, and so we, uh... I, I just got exposure to video games and computers, and I was like: "Wow, this is incredible. Like, computers are gonna change everything." And then I happened to w- hack some software. We used to... I ran a lot of scams, uh, but, uh, [chuckles] we-

    24. SP

      You told us about the, the VHS.

    25. JC

      So VHS-

    26. SP

      Relay

    27. JC

      ... Jason's Hot Tapes was technically my first business.

    28. SP

      [chuckles]

    29. JC

      But there was a side job I had, which was cracking software. So we were- we would make copies of, like, Chess Master and stuff like that, and then sell them for 10 bucks. And then we started, like, hacking and doing what was called phone phreaking.

    30. BG

      Wh- when you were doing this stuff, like, it took you to be reasonably technical to do it. Not like the, you know, not like-

  5. 7:31 – 8:33

    Choosing media: zines → Cyber Surfer → Silicon Alley Reporter

    1. BG

      Did you ever think about... Like, did, did you consciously ever make a fork where you were, like, not tech media, and of course, media about tech-

    2. JC

      Yeah

    3. BG

      ... but you're like, "I'm not gonna be the guy doing the boards. I'm gonna be the guy writing about the people doing the boards?"

    4. JC

      It's a very good question. I used to go to Bleecker Street, and I used to hang out in the West Village or the East Village. It was, like, the cool places to hang out. And, um, like, a thing to do would be to go to Tower Records and look at the zine section.

    5. BG

      Yeah.

    6. JC

      So there was a concept of a zine, which was short for magazine, but a zine was something you wrote with your friends, you printed it yourself at a photocopy store.

    7. BG

      It's like blogs before blogs.

    8. JC

      Blogs before blogs, and I created a zine. I was like: "I'm gonna be a magazine publisher." So the first one I did was Cyber Surfer, which was about dial-up magazi- dial-up services and CD-ROMs.

    9. BG

      Yeah.

    10. JC

      And I did it with my friend Brian Alvey, uh, whom you might have heard of in my career.

    11. BG

      Yep.

    12. SP

      He did-

    13. JC

      We went to high school together.

    14. SP

      Weblogs?

    15. JC

      We did Weblogs together, yeah. So but in the early '90s, I did Cyber Surfer.

    16. BG

      Which was Engadget, TWiT-

    17. JC

      All of that stuff.

    18. BG

      Yeah.

    19. JC

      Journey to-

    20. BG

      Everything you sold to AOL.

  6. 8:33 – 12:31

    Accidental VC proximity: meeting Jerry Colonna & Fred Wilson and the GeoCities moment

    1. JC

      Thing I sold to AOL. Uh, but anyway, before that, I did this mag- I did that magazine, and then I had met Fre- I met Jerry Colonna at, uh, Internet World, the first one, and he... There was a booth.

    2. BG

      That's right, when Jerry was a VC, before he was, like, the-

    3. JC

      Before he was a VC

    4. BG

      ... whisperer of startup coaches

    5. JC

      ... he was consulting for Lycos, and I think CMGI.

    6. BG

      Oh, yes.

    7. JC

      And so there was a Lycos booth, and I had met this young lady at it, and we hit it off, and we're talking, and then she introduced me to Jerry Colonna. And then I met Jerry Colonna in a office no bigger than this room in, on, uh, Union Square, and he said, "Listen, I'm leaving Lycos, but I'm gonna start this Acme Ventures with my friend Fred. Um, I want you to come, um, read business plans for us." And so I met Fred Wilson, and I would go up to them, and they were doing... JP Morgan was gonna back them for their venture firm.

    8. BG

      Wow.

    9. JC

      This was 1994, '95.

    10. SP

      This became Flatiron.

    11. JC

      And it became Flatiron.

    12. BG

      JP Morgan-

    13. SP

      Which was the-

    14. BG

      ... the first big anchor of Flatiron?

    15. JC

      They were half of it, and Masayoshi Son, SoftBank, was the other half.

    16. BG

      No way!

    17. SP

      So they wanted-

    18. JC

      No shit

    19. SP

      ... you to come, like, be a VC associate.

    20. JC

      Not a VC, just to read business plans.

    21. BG

      [chuckles]

    22. JC

      So the deal was they would take me for sushi and pay me 1,000 bucks-

    23. BG

      Wait, what do VC associates do-

    24. JC

      To read business plans

    25. BG

      ... besides just read business plans?

    26. JC

      Exactly.

    27. BG

      [chuckles]

    28. JC

      Well, anyway, it was a thing. And so I had the magazine started, Silicon Alley Reporter, and they were paying me, and so I read, uh, about this, um, um, Beverly Hills internet company, which got rebranded as GeoCities.

    29. SP

      Oh.

    30. JC

      And I wrote a little coverage of it, and I said, "You should invest."

  7. 12:31 – 22:42

    All-In origin story: poker friendships, pandemic timing, and adding the “besties”

    1. SP

      Um, 'cause the last time we talked to you, you were just starting All-In.

    2. JC

      Hilarious, yeah.

    3. SP

      And, like, can we talk podcasting?

    4. JC

      Of course. I love it. Podcasting is, like, I think perhaps my greatest medium.

    5. SP

      What happened with All-In? How did, uh, I mean, it's-

    6. JC

      It's weird [laughs]

    7. SP

      ... It, has it surpassed your wildest expectations?

    8. JC

      Um, I thought it would be something Chamath and I would do 10 times.

    9. SP

      Yeah.

    10. JC

      So the, the origin story is pretty simple. Um, Chamath, uh, I knew because he was running ICQ.

    11. SP

      Chamath was running ICQ?

    12. JC

      At AOL, and I had sold my company to AOL, and-

    13. SP

      That's-

    14. JC

      Like, the revolving door of AOL

    15. SP

      I didn't know that was the lineage.

    16. JC

      There was like, Ted Leonsis had this March to a Billion, uh, my Greek brother and mentor, had this, like, March to a mil- a Billion, uh, offsite. And so I went to this, and I had just sold Weblogs Inc. to them-

    17. SP

      Like, a million AOL users?

    18. JC

      I was hot shit.

    19. SP

      That's the, the application?

    20. JC

      That was the idea, was that... Well, with Weblogs Inc.-

    21. SP

      Yeah

    22. JC

      ... and with, uh, AOL and other assets they wanted to buy, they were gonna march to a billion users.

    23. SP

      Yeah.

    24. JC

      It was, like, this crazy rallying cry, and we had these T-shirts, "March to a billion." So I go to that, and I see Chamath, and I was like, "Hey!" And he's like, "Hey." And, uh, we introduced each other, and we had known of each other, and I said, "What are you doing here?" He's like, "I'm running ICQ into the ground, you know, I'm just riding it down. Every month it loses a million members," [laughs] whatever. I said, "It's hilarious."

    25. SP

      [laughs]

    26. JC

      And he's like, "Yeah-

    27. SP

      Amazing

    28. JC

      ... "But I'm leaving. I'm gonna go, um, I'm gonna go to the West Coast. I'm gonna go work at this VC or whatever." I was like, "All right, nice seeing you." Um, and so then when he was there, I was in LA, uh, and-

    29. SP

      What VC did he go work? 'Cause he was at Facebook.

    30. SP

      Mayfield.

  8. 22:42 – 28:41

    Why All-In works: crossover audience, character-building, and moderating for “dentists”

    1. JC

      ... live your life. I- that's one of the things I love about San Francisco. But anyway, the pod's gotten very big.

    2. BG

      So you get the gang together and, like-

    3. JC

      Yeah.

    4. BG

      What, why do you think it works? Like, is it that you-

    5. JC

      Why do you think it works?

    6. BG

      It's, like, the number one-ish tech or business podcast.

    7. JC

      Well, in our, in our business, it's number one, of course, but it's num- it was number 28 last week-

    8. BG

      Like, in the world

    9. JC

      ... overall on iTunes.

    10. DR

      All- you guys have transcended. Like, this is more than just-

    11. JC

      It has nothing to do with tech anymore.

    12. DR

      Yeah.

    13. JC

      It has nothing to do with finance or tech anymore. It is-

    14. BG

      I think it works

    15. JC

      ... tipped over into colleges. I was at-

    16. BG

      Colleges

    17. JC

      ... I was at, you know, skiing in Tahoe, and I, you know, I was with my kids, and it's hard to get a table type situation.

    18. BG

      Right.

    19. JC

      I was like, "Hey, I hate to be a pest, but I see you're wrapping up. Are you... And no pressure, but are you gonna be leaving soon? 'Cause I'd love to camp out here and get your table."

    20. BG

      And they're like, "Stop busting my balls, Jason." [chuckles]

    21. JC

      And the woman looked at me, and she goes, "JCal?" And I was like-

    22. DR

      Holy crap

    23. JC

      ... "Have we met?" And she's like, "No, I listen to your pod twice a week." I'm like, "It's only out once a week." [chuckles]

    24. BG

      [chuckles]

    25. JC

      "I listen to it twice." And I was like, "Oh, my God, that's so nice." She's like... I was like, "C- are you in the industry?" She's like, "I'm a dentist."

    26. BG

      Wow.

    27. DR

      Holy crap.

    28. JC

      "Reno." And I'm like, "You're a dentist in Reno. So may I ask how you found out about..." She's like, "I don't know." Like, she-

    29. BG

      She's like, "I deeply care about San Francisco politics?" [chuckles]

    30. JC

      No. [laughing] It's like how she had found it-

  9. 28:41 – 34:47

    Politics, tribes, and the value of arguing with friends (center vs extremes)

    1. JC

      Being known, but yeah, you know, and I, I think part of the reason this works is Sachs... I think Sachs has probably taken the brunt of the hit of the pod-

    2. BG

      Yeah.

    3. DR

      Yeah

    4. JC

      ... because he is so passionate about, you know, a lot of topics that maybe are unpopular in the tech circle. So I do think, like, it's cost him deal flow on the margins probably.

    5. DR

      Mm.

    6. JC

      I think there's probably, uh-

    7. BG

      Ah, I don't... Really, margin? Like, I-

    8. JC

      I wonder. I wonder

    9. BG

      ... on balance, he-

    10. JC

      He, he said that jokingly on the show.

    11. BG

      No.

    12. JC

      I don't know. I'm just thinking, like, maybe there's somebody that-

    13. BG

      Sachs has ascended because he's done All-In, in a way, that-

    14. JC

      I guess. Yeah, sure.

    15. BG

      Uh-

    16. JC

      I'm trying to think if, like, would... Is there a founder, uh, I wonder, I don't know this, but is there a founder, who's a young founder, who would say, "I would never take money from Peter Thiel's venture firm, 'cause I'm so liberal"?

    17. BG

      For sure there are, and then-

    18. JC

      Okay, so then-

    19. BG

      ... those people feel that way about Kraft now, but for every one of those, there's 10 more who know about Kraft now.

    20. JC

      I, I kind of agree with your pers- yeah, I would agree with that. So anyway, I do think, like, he's joked that it's cost him deal flow. I don't know if it has. Um, I think surely the benefits are-

    21. DR

      Well, I think also, the pod, too, I think for peop- for people in America and people in tech, has moved, I think, a lot of people towards the center.

    22. JC

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

    23. DR

      Yeah.

    24. JC

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

    25. DR

      Yeah.

    26. JC

      You know, I've, I, I've been telling folks from the beginning, I'm an independent and a moderate. I voted probably Democratic three out of five times, four out of five times, but mostly that's a function of the fact that I've lived only in New York and California in my life, where you don't really get many Republicans or moderates. But I've voted for Bloomberg, Giuliani, when, where he was crazy, [laughing] and Pataki, who were all Republicans.

    27. BG

      It's insane to me that-

    28. DR

      Were you here during the Schwarzenegger era-

    29. BG

      ... that is the same as Giuliani

    30. DR

      ... or are we still New York?

  10. 34:47 – 50:56

    Money, meritocracy, and Founder University as a practical pathway

    1. SP

      On, on, on that, what- another thing that's really fascinating to me about All-In-

    2. JC

      Yeah

    3. SP

      ... and you guys is before All-In, and maybe, and still to a large extent, I feel like Silicon Valley has this weird relationship with money, like, super weird-

    4. JC

      Yeah

    5. SP

      ... relationship with money.

    6. JC

      Yeah.

    7. SP

      Like, you know, remember there's a whole thing about, like, Zuck drove, like, an Acura SB- SUV-

    8. JC

      Oh, my God, that all came from-

    9. SP

      And like-

    10. JC

      ... David Filo and, um, David Filo and Jerry Yang were driving their old cars to work-

    11. SP

      Right, like, the cool thing, like, you, you could, like, make money, build a company-

    12. JC

      Yeah, never have a fast car

    13. SP

      ... but, like, you never wanna, like, you never-

    14. JC

      Yeah.

    15. SP

      And-

    16. JC

      He understood it, yeah. It's not just-

    17. SP

      You guys, I think, are the first, like... Uh, like, you, you guys are like-

    18. JC

      Whatever

    19. SP

      ... "Fuck, like, we got a private jet. Like, that's fine." Like, you know?

    20. JC

      I mean, [exhales] listen, I, I, uh, uh, you know, yeah, I believe in capitalism. I think it's great if people create jobs and if they get rewards for doing so. Like, fine. I, uh, literally, the, the book I'm writing, my second book right now I'm writing is about wealth and money, and like... But not, like, in my regard, but in a sort of, like, big-picture, societal regard. So I've, like, literally been thinking about this topic a ton, and I think we worry a little bit too much about wealth creation, um, with, like, a small, like, outlier wealth creation, and we, and we don't think enough about inspiring people to create companies-

    21. SP

      Yeah

    22. JC

      ... and learn. And, like, the time I create the most controversy is when I'm like: "I believe anybody can do it." And people are like: "You're so wrong!" And I'm like: "Am I? Because I go on YouTube, and you could type in any topic that you want to learn, and you can learn it." And all the stuff that was at MIT, where I never got to go, and Stanford and Brown, is online for free, and I listen to macroeconomic classes and AI classes. When I'm, like, it's 10 o'clock at night and I'm doing my email, I'll just put one of those playlists on from MIT OpenCourseWare, and I'm like, "I can't believe I can take a course at MIT for free anytime I want."

    23. SP

      And then you, you know, flip it, you can build a business there. Like David Senra over at the Founders podcast, like MrBeast, MKBHD-

    24. JC

      The world has-

    25. SP

      Like, the-

    26. JC

      The world has never been this equitable.

    27. SP

      Nobody gave these guys permission. Yeah.

    28. JC

      ... but people want to spread a narrative that the world is unfair. And, like, I watched-

    29. BG

      Well, I think the world-

    30. JC

      -the world become so fair, and so just, and so much information and opportunity become available that I'm like, "Wait a second." We- I could never figure out how a term sheet worked, and nobody would share their term sheet, and now there are a thousand videos and blog posts on how to negotiate your term sheet.

  11. 50:56 – 59:30

    Bay Area critique: politics, regulation, and why founders leave (Austin/Miami pull)

    1. SP

      Um, Silicon Valley.

    2. JC

      Yeah.

    3. SP

      I feel like there... Especially, there's a lot of... Part of the, even the origins of All-In, there's a lot of, like, bashing on San Francisco politics and Calvin. Like, there's a lot of crap wrong here.

    4. JC

      Yeah.

    5. SP

      But you guys are all still here.

    6. JC

      For now.

    7. SP

      How are you guys feeling about that?

    8. JC

      For now.

    9. SP

      Yeah, how do you, how do you feel about that?

    10. JC

      Yeah.

    11. SP

      Like, what, what do you think of the Bay Area?

    12. JC

      I, um, you know, I lived in New York, Brooklyn, then Manhattan, and then I lived in LA, and then I lived here. And so I think my... I'm moving to places I enjoy less and less each time. [laughing]

    13. SP

      [laughing]

    14. JC

      Like, I enjoyed Brooklyn and Manhattan much more than LA. I enjoyed LA much more than San Francisco, so-

    15. SP

      Interesting

    16. JC

      ... I don't know where to go next, but I'm gonna go somewhere like [chuckles]

    17. SP

      Wait, so why are you still here then?

    18. JC

      Uh, well, I ca-

    19. SP

      There's no reason for you to be here.

    20. JC

      I came up here because I had a lot of friends up here.

    21. SP

      Yep.

    22. JC

      And I had done LA, and I was like, "I wonder how far..." You know, I'd been a Sequoia Scout, and then I was like, "My friends are telling me I can start a venture fund. You kind of need to be up there. I wonder how I would do if I was up there in the industry." And I was kind of this-

    23. SP

      'Cause if you wouldn't, you'd always wonder.

    24. JC

      Well, Mari- Michael Moritz used to call me the mouth from the South.

    25. SP

      [laughing]

    26. JC

      Uh, because I had, like, two investments in LA. He said, "Oh, the mouth from the South is here. [laughing] What have you got yourself into, JCal?"

    27. SP

      [laughing] I can imagine Sir Michael saying that.

    28. JC

      Uh, but I moved up here, and, yes, I love it up here. It's quite bucolic. My kids are loving it. Um, it's, it's quite nice. I would love to live in another city in my life, uh, or two. Uh, I could see myself in Austin or Miami. I like both of those cities. I think Austin's kind of the future. I think California-

    29. SP

      Hmm

    30. JC

      ... is gonna be, uh, damaged for a decade or two, so I think for the rest of our adult lives, this town-

  12. 59:30 – 1:05:49

    Act 3 energy: cutting drudge work, scaling teams, and “not for me” delegation

    1. DR

      We referenced this at the start of our conversation. You're working as hard or harder than you ever have. You said you've got a-

    2. JC

      Smarter

    3. DR

      ... a new well of energy.

    4. JC

      Yes.

    5. DR

      Tell us about it.

    6. JC

      Well, I find great purpose in what I do, and, uh, when my friend Tony Hsieh died, I really thought deeply about, like, what I wanted to get out of the rest of my life. And I realized, like, w- these are the things I really love doing, and these are things maybe not so much.

    7. DR

      Hmm.

    8. JC

      And I just realigned my life over the last two years. And-

    9. DR

      So what are the-

    10. BG

      What are those two buckets?

    11. JC

      Yeah, exactly. So I can tell you the things that just, to me, I'm just not gonna get any pleasure amount out of life.

    12. DR

      Yeah.

    13. JC

      Um, working, like, no offense to my incredible lawyers, but negotiating term sheets, and legal, and HR issues, and accounting, and operations, and tax, and, you know, that entire stack of things-

    14. DR

      Yep

    15. JC

      ... not fun to me. Not fun at all.

    16. BG

      And I'm sure you never viewed that as fun, but at least before you were like, "I'm willing to put up with it, 'cause it m- may- maybe it's a thing that-

    17. JC

      Absolutely

    18. BG

      ... creates value enough for me to do it."

    19. JC

      Absolutely. Um, doing my podcast every day, absolute joy.

    20. DR

      Hmm.

    21. JC

      Entertaining an audience, you know, thinking, uh, thinking about the world and having these conversations. I had Tobi from Shopify on today.

    22. BG

      Oh, wow.

    23. JC

      Like, I leave the Tobi interview... It's, like, his third or fourth time on the pod.

    24. DR

      That's awesome.

    25. BG

      Cool.

    26. JC

      And it's just like, instead of us having dinner or lunch, we just record a pod. The end. Um, and to me-

    27. BG

      Did you do it in person, or did he-

    28. JC

      No, just, you know-

    29. BG

      Zoom

    30. JC

      ... hopped on Zoom.

  13. 1:05:49 – 1:17:34

    Raising a fund in public + democratizing VC access (506(c), QPs, AngelList limits)

    1. BG

      Ooh, are you enjoying the LP fundraising?

    2. JC

      I am now, yeah. I, I'm, I'm kind of like, uh... Remember in Ax- I don't know if you watch Billions?

    3. BG

      Oh, yeah, every episode.

    4. JC

      Great. So you know, like, at some point, um, uh, he was like, "I'm gonna go raise money."

    5. BG

      Yeah, it's cap raise time.

    6. JC

      It's cap raise time, and, like, Wags is like... So I got my Wags. Mike Savino's my Wags-

    7. BG

      Yeah. [laughing]

    8. JC

      ... And I got my Wags, who just fixes everything.

    9. BG

      [laughing]

    10. JC

      And I'm like, "I'm gonna go raise money." And so literally was like, "We're doing 506 (c) ,", and they're like-

    11. DR

      And, and so you've talked about this now

    12. JC

      ... "Go do that."

    13. DR

      You're, you're now... You were in kind of this one bucket with your capital, and now you're going simultaneously in two directions of you want the public and you want the big institutions, right?

    14. JC

      We'll see. Um, I've had select institutions make small bets. The first one was 10, the next one was 11, and then the last one was 44 million. The first fund I deployed in five years, the second fund, two years, the third fund, two and a half.

    15. DR

      Five years? Wow!

    16. JC

      I was just- that was my first fund.

    17. DR

      Yeah.

    18. JC

      It was, you know, me-

    19. DR

      Right

    20. JC

      ... Bill Gurley, Dave Goldberg, rest in peace, Tony Hsieh, rest in peace, David Sacks, Chamath. Just a bunch of my friends put money in, and it was to see if I wanted to be a venture capitalist and do this as a career. And I was like, "Yeah, I just did it over five years." And the second one, I, I raised 11. Took me six months to a year to raise the first. It took me- the second one took three to six months. The... No, it took six months. The third one took me three months to six months, and in this one, I, I think I'll wind up raising in the first 10 days what I raised in the first... yeah, couple of funds.

    21. DR

      Wow!

    22. JC

      Like, I literally did-

    23. DR

      That's awesome

    24. JC

      ... two webinars. A couple of hundred people came to each show. For people who are listening, 506 (c) is you can raise in public, which means you just can tell people, "I'm raising a fund." And I was like, "Well, I'm doing All-In. It doesn't make any money. Uh, I have This Week in Startups," and I watched a bunch of these young, um, aspiring VCs raise, uh, publicly.

    25. DR

      Right.

    26. BG

      Yeah.

    27. JC

      Uh, you didn't raise publicly?

    28. DR

      No.

    29. JC

      You did private. Uh-

    30. DR

      I thought about it, but for a whole bunch of reasons...

  14. 1:17:34 – 1:28:52

    Real angel investing: Calm, pricing strategy, and Jason’s early-stage “nine factors”

    1. JC

      there with them and figured it out with them.

    2. DR

      Oh, man, we were talking about the legendary-

    3. JC

      That's the rush

    4. DR

      ... twist, Episode 180, with you and D- and Travis.

    5. JC

      Yeah. Yes.

    6. DR

      Like, man, that was-

    7. JC

      I mean, that was-

    8. BG

      That's the secret before the show stuff, David.

    9. DR

      Yeah, that is the secret.

    10. BG

      [laughing]

    11. DR

      But, but from the, from the juicy before the show.

    12. JC

      No, I mean, I'll talk about... I can talk about Travis.

    13. BG

      Mm.

    14. JC

      Yeah.

    15. DR

      Yeah, but that was like, you know, you know, Urban was such a baby company back then, and like, you know-

    16. JC

      Crazy. One city.

    17. DR

      One city.

    18. JC

      I mean, I invested, and I had an open angel for them where Sayan Bannerman and Chris Sralik from First Round, you know, invested in the company. I think they both met them there. Saka was there, too, but he already... He had a relationship with Travis, so I can't take any credit for that. And Kevin Systrom was watching, and I was gonna kick him out-

    19. DR

      [laughing]

    20. JC

      ... because he was at this co-working space called Dogpatch Labs.

    21. BG

      Oh, I- I worked there, too.

    22. JC

      Yeah, and it was-

    23. BG

      I worked at Cotweet.

    24. JC

      Yeah, so he was... Oh, Cotweet, I know that.

    25. BG

      Yeah.

    26. JC

      So he's sitting over there building Bourbon-

    27. BG

      Yep.

    28. DR

      That's right.

    29. JC

      And, and Saka's like, "Can Bourbon come in?" I'm like, "Fuck, no, this is, like, private shit."

    30. BG

      [laughing]

  15. 1:28:52 – 1:54:11

    Public markets mindset + M&A thinking: Adobe/Figma and why “overpaying” can be right

    1. JC

      Uh, well, depending on-

    2. DR

      We'll see. We'll see

    3. JC

      ... depending on entry price.

    4. DR

      We'll see.

    5. JC

      Yeah, I don't know what's gonna happen to these companies after, you know... Uh, like, flat is the new up, but I think, you know, 50% haircut is the new flat, so.

    6. DR

      Well, the public comps got hit 50-plus percent.

    7. BG

      Yeah.

    8. JC

      I mean-

    9. BG

      This week, they got hit harder again.

    10. JC

      Yeah, I mean, I, I'm buying equities right now. I've been doing it on-

    11. DR

      Day trading

    12. JC

      ... daytrading.com, and, um, I am gonna buy more, uh, in the fourth quarter.

    13. BG

      Sorry about all my picks a couple weeks ago.

    14. JC

      Which one?

    15. BG

      Uh, whatever I talked about.

    16. JC

      Oh, yeah, yeah. No, no-

    17. BG

      Certain one

    18. JC

      ... I, I actually love Taiwan Semiconductor, uh, and, uh-

    19. BG

      Oh, good one.

    20. DR

      And Stitch Fix was the other one.

    21. BG

      And Stitch Fix.

    22. JC

      No, Stitch Fix wasn't yours.

    23. BG

      No, Twilio.

    24. JC

      Twilio was yours, and I love that one, too. And I, I, I like Shopify as a pick. Um, I'm actually really enjoying it. It's really, I think-

    25. BG

      Not investment advice

    26. JC

      ... balancing out... Not investment advice, but, um, it's balancing out my, um, understanding of what public success is compared to private. And so for me-

    27. BG

      Yes

    28. JC

      ... it's just a way, like, am I going to fight with a blaster? No, I'm a Jedi. I use a lightsaber.

    29. BG

      [laughing]

    30. JC

      But, you know, I'll learn-

  16. 1:54:11 – 2:14:53

    Venture “Mount Rushmore” → the Venture Capital Hall of Fame idea (and debate over a16z)

    1. JC

      When you guys are having the conversation in 20 years, and I'm gone or I'm retired, and you're saying Mount Rushmore-

    2. DR

      It's hard to imagine you retiring.

    3. JC

      Pro- yeah, nothing's possible. Um, I met Don Valentine when they were like... You know, he was not an active investor, but when I pitched Mahalo, he was in the room. He came up.

    4. DR

      Yeah.

    5. JC

      I talked to him. It was pretty-

    6. BG

      He was... Oh, he was still hanging out there all the time.

    7. JC

      He was still hanging out.

    8. DR

      Yeah.

    9. JC

      It was awesome.

    10. DR

      Yeah.

    11. JC

      Um, yeah, like, why retire? Um, he was just awesome.

    12. DR

      Oh.

    13. JC

      Um, but, you know, if you had that conversation right now-

    14. BG

      Yeah

    15. JC

      ... about Mount Rushmore, like, you gotta... Okay, so-

    16. DR

      Who's, who's on your Mount Rushmore?

    17. JC

      Well, I mean, you've gotta have Don Valentine.

    18. BG

      Yeah.

    19. DR

      Right.

    20. JC

      Right? That's just not possible, but-

    21. BG

      And how are you scoping it? 'Cause you probably need Paul Graham, too.

    22. JC

      Well, yeah. I mean, you have Paul Graham is in the running for sure, but that's, like, a number of startups, but there's a lot of big ones in there. You have big impacts, so Paul Graham's definitely in the running. But okay, so do you go with-

    23. DR

      John Doerr.

    24. JC

      John Doerr's in there, along with... So if you're doing firms, it's a lot easier-

    25. DR

      Right

    26. JC

      ... 'cause you get Khosla, Doerr, and, um, Perkins, Tom Perkins. You get the three of them at once.

    27. DR

      Yeah. Yeah.

    28. JC

      You do Sequoia, you know, you got-

    29. DR

      Which all the... For, people forget-

    30. JC

      Yeah, because that's like-

Episode duration: 2:23:51

Install uListen for AI-powered chat & search across the full episode — Get Full Transcript

Transcript of episode kbKGlAJsPIE

Get more out of YouTube videos.

High quality summaries for YouTube videos. Accurate transcripts to search & find moments. Powered by ChatGPT & Claude AI.

iOSAndroidClaudeChrome