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Tim FerrissTim Ferriss

Jason Calacanis on Brooklyn Grit, Big Asks, The Magic of Thinking Big, and More

Brought to you by Eight Sleep’s Pod Cover sleeping solution for dynamic cooling and heating https://eightsleep.com/Tim and LinkedIn Jobs recruitment platform with 800M+ users https://linkedin.com/tim. Resources from the episode: https://tim.blog/2022/11/18/jason-calacanis/ Jason Calacanis (@jason) has invested in more than 300 startups in the past decade (Uber, Calm, Robinhood, and more), was Sequoia Capital’s first Scout, and is the author of the book ANGEL. He also hosts two podcasts, This Week in Startups and All-In. Please enjoy! [00:00] Start [00:52] Why is this only the first time Jason’s been on the show? [01:48] Never underestimate the power of checklists. [04:12] How Jason’s young life was steeped in blood and taxes. [07:21] How Jason entered the world of entrepreneurship. [24:06] What happened when Jason got fired from his own company. [28:51] Orchestrating a comeback the very next day. [32:28] The Mercury Club that never was. [36:20] The origin of “Calacanis.” [37:46] Building a blogging empire. [43:28] Finding blog writers. [47:37] Planning events and making memories. [53:30] Friendship, loyalty, and collaboration with close friends. [1:01:12] All-In: When a solo act gets tricked into joining a band. [1:09:02] Memorable times All-In has gone off the rails. [1:17:10] With greatly followed podcasts comes great responsibility. [1:23:14] Keeping All-In running smoothly with four very different personalities. [1:30:41] Talent-wrangling techniques. [1:35:26] Bill Maher’s moderation style. [1:36:42] Friendly rapport can be contagious. [1:38:23] Can you see your comfort zone from the Overton window? [1:41:50] Transfering skills, building popularity, and co-existing with jet blockers. [1:48:51] What happens when you catch the car? [1:51:54] Psychedelic therapy and a big win in Colorado. [1:58:25] Jason’s billboard and parting thoughts. About Tim Ferriss: Tim Ferriss is one of Fast Company’s “Most Innovative Business People” and an early-stage tech investor/advisor in Uber, Facebook, Twitter, Shopify, Duolingo, Alibaba, and 50+ other companies. He is also the author of five #1 New York Times and Wall Street Journal bestsellers: The 4-Hour Workweek, The 4-Hour Body, The 4-Hour Chef, Tools of Titans and Tribe of Mentors. The Observer and other media have named him “the Oprah of audio” due to the influence of his podcast, The Tim Ferriss Show, which has exceeded 800 million downloads and been selected for “Best of Apple Podcasts” three years running. Connect with Tim Ferriss: Sign up for "5-Bullet Friday" (Tim's free weekly email newsletter): https://go.tim.blog/5-bullet-friday-yt/ Visit the Tim Ferriss PODCAST: https://tim.blog/podcast/ Visit the Tim Ferriss BLOG: https://tim.blog/ Follow Tim Ferriss on TWITTER: https://twitter.com/tferriss/ Follow Tim Ferriss on INSTAGRAM: https://www.instagram.com/timferriss/ Like Tim Ferriss on FACEBOOK: https://www.facebook.com/TimFerriss/

Tim FerrisshostJason Calacanisguest
Nov 18, 20222h 6mWatch on YouTube ↗

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EVERY SPOKEN WORD

  1. 0:00 – 0:52

    Start

    1. TF

      [upbeat music] Hello, boys and girls, ladies and germs. This is Tim Ferriss. Welcome to another episode of The Tim Ferriss Show. We're getting close to 700 episodes. Crazy to think. And my guest today, long overdue, is Jason Calacanis. Calacanis, don't leave out the second A, folks. He has invested in more than 300 startups in the past decade, was Sequoia Capital's first scout, and is the author of the book Angel. He also hosts two podcasts we're gonna talk quite a bit about, This Week in Startups and All-In. You can find him online at Calacanis, that's C-A-L-A-C-A-N-I-S, .com, and on Twitter @jason, because he was an early bird on the

  2. 0:52 – 1:48

    Why is this only the first time Jason’s been on the show?

    1. TF

      Twitter platform. Jason, nice to see you, man.

    2. JC

      It's nice to see you, brother. You and I have random phone calls for, like, an hour or two, and I think this is the first time we're actually recording it, so.

    3. TF

      It's the first time. [laughs]

    4. JC

      I listen to, I would say, two out of three of your episodes.

    5. TF

      Thank you.

    6. JC

      You've had a lot of investors on.

    7. TF

      I have. I have.

    8. JC

      Somebody's like, "How come you haven't been on Tim Ferriss' podcast?" I'm like, "He's had so many investors on. What can I add," right? And, you know-

    9. TF

      Oh, there's-

    10. JC

      ... I'm sure at some point-

    11. TF

      There's a lot

    12. JC

      ... well, sure. I'm sure.

    13. TF

      [laughs]

    14. JC

      But, I mean, I, it is so great to see how well your podcast has done over the years.

    15. TF

      Oh, thanks, man.

    16. JC

      So I remember the first time I met you in Tahoe with, I guess, Sacca.

    17. TF

      Mm-hmm.

    18. JC

      And it was like, "Hey, this is the 4-Hour Workweek guy." And I was like, "You know how hard you're making my life?"

    19. TF

      [laughs]

    20. JC

      All [laughs] these founders I meet, now they think I work four hours.

    21. TF

      [laughs]

    22. JC

      I started breaking their chops. [laughs]

    23. TF

      [laughs] Oh, it's part of the charm. Yeah, it is, it's part of the charm.

    24. JC

      Good to see you.

    25. TF

      It is good to see

  3. 1:48 – 4:12

    Never underestimate the power of checklists.

    1. TF

      you. And so, I, you, I consider a master of podcasting. We're gonna come back to that, because I have some other questions maybe before that. But I wanted to give an example of a great piece of tactical advice, and you actually told me about this before we started recording.

    2. JC

      Mm.

    3. TF

      QuickTime. So we are both running backup QuickTime audio.

    4. JC

      Yes.

    5. TF

      So we have extra local copies in case something breaks, 'cause things often break.

    6. JC

      Yes.

    7. TF

      What was the, what was the tactic that you shared? 'Cause it's so smart.

    8. JC

      You load a QuickTime thing, and you're like, "Hey, can you start a QuickTime?" People go, "Oh yeah, my QuickTime's running." But then, one out of three times, at the end of the show, we're like, "Okay, can you upload the QuickTime?" They're like, "Oh, I didn't hit the record button."

    9. TF

      Yeah.

    10. JC

      So instead of asking, "Can you s- you know, record a QuickTime?" I say, "How many seconds is your QuickTime running?"

    11. TF

      Mm-hmm.

    12. JC

      And they say, "It's with 36 seconds." Now I know it's running.

    13. TF

      Mm-hmm.

    14. JC

      And, but the bigger piece is there's this book, uh, The Checklist Manifesto. You and I are obsessed with.

    15. TF

      Yeah.

    16. JC

      Probably part of our kinship.

    17. TF

      Atul Gawande.

    18. JC

      Yeah, we're both into, like, tools and optimization. And this book, I had heard Jack from Twitter would give it to every Square employee, give it to every Twitter employee, The Checklist Manifesto. And I make everybody read it. I'm obsessed with checklists. And so, you know, 'cause people forget.

    19. TF

      People forget.

    20. JC

      And all those great stories in the book about, like, surgeons and pilots were like-

    21. TF

      Oh, incredible

    22. JC

      ... "I don't need a checklist," and then everybody dies. [laughs]

    23. TF

      Yeah.

    24. JC

      And then a nurse comes along, and it's like, "Well, I could just make this little checklist for you, and we could just, you know, you say something, I say okay. You say something, I say okay." And then all of a sudden, you could have-

    25. TF

      Yeah

    26. JC

      ... a plane with four engines.

    27. TF

      Yeah.

    28. JC

      Because people had more discipline and, you know.

    29. TF

      And it's like, oh, I know you guys didn't need this checklist, but we have bacterial line infections down by 39% this year. Oh, go look at that. Yeah, it's, it's a great book.

    30. JC

      People would take a scalpel that was dirty, and they made this little device, right? These little life hacks, you know, that are, are so much a part of what you do. And by the way, super weird for you to tell me that I'm a podcast master, because I take notes on your podcast. [laughs]

  4. 4:12 – 7:21

    How Jason’s young life was steeped in blood and taxes.

    1. JC

      No bueno.

    2. TF

      Now, you can't believe everything you read on the internet, so please correct me if I'm getting any of this wrong, but-

    3. JC

      Yeah, sure

    4. TF

      ... you know, your mom was tending to people in the ER.

    5. JC

      Yeah.

    6. TF

      Your dad had a, had a bar, as I understand it.

    7. JC

      Yeah.

    8. TF

      There were times when you would be cleaning blood off the floor [laughs] from all the brawls and fights.

    9. JC

      For sure.

    10. TF

      And then, and then raided at one point, I think, by the, I don't know if it was the FBI, but with, like, the sh-

    11. JC

      Tax authorities

    12. TF

      ... tax authorities.

    13. JC

      Shotguns. Yeah, my dad got a little behind on the taxes. Uh, they-

    14. TF

      Yeah, the taxes, they sneak up on you.

    15. JC

      It turns out the Tax Authority, they're kind of humorless.

    16. TF

      [laughs]

    17. JC

      Like, pay your taxes or you go to jail. And so when I was 18 years old, growing up in Bay Ridge, Brooklyn, which is the last stop on the train, just to give you an idea of how far out there it is. This is in the '70s and '80s. In 1988, my dad's bar, after the stock market crashed, he went into basically debt, and it was really gnarly. And then one summer afternoon in July, the feds, basically, and the Tax Authority came and padlocked the place, took everything out of it. And, you know, this close to my dad going to jail. And had, you know, one of the great traumas of my life. And it's one of the things I really appreciate and respect about you is you shared your trauma on this podcast. It's like a gift to the world.

    18. TF

      Hmm.

    19. JC

      You know, that's a pretty scary thing when you're 17 years old and you're like, Dad says, "I'm sorry, son, I don't have money for college. I'm probably going to jail. I tried to make this business work. It didn't work."

    20. TF

      Hmm.

    21. JC

      "Take care of your mom." Like, whoa.

    22. TF

      That's rough.

    23. JC

      It's kind of like that scene when, y- uh, if you remember in The Empire Strikes Back, and, like, Han Solo comes over to Chewbacca. He's like-

    24. TF

      Hmm

    25. JC

      ... "Just take care of the princess. I'll be back."

    26. TF

      Yeah.

    27. JC

      You know? It was really intense. Really intense.

    28. TF

      Yeah. Yeah, I bet that's-

    29. JC

      It's crazy

    30. TF

      ... I bet that's an memory.

  5. 7:21 – 24:06

    How Jason entered the world of entrepreneurship.

    1. JC

      [laughs] I have to say.

    2. TF

      So if we flash forward a little bit, and we, we don't necessarily have to spend a ton of time on this, but Silicon Alley Reporter, in the beginning, I mean, you're photocopying it yourself, you're hand-delivering it-

    3. JC

      Yeah

    4. TF

      ... to coffee shops and other spots.

    5. JC

      Yeah.

    6. TF

      Did you know or decide you were going into business for yourself to be an entrepreneur? And I ask especially given what you saw happen to your dad, right? I can see-

    7. JC

      Yeah

    8. TF

      ... some people responding by going entirely in the opposite direction, getting the safest nine-to-five possible. So how did you end up an entrepreneur?

    9. JC

      So having a dad who was an entrepreneur, it kind of puts it in you.

    10. TF

      Yeah.

    11. JC

      And I, you know, had one or two jobs when I was in college. I went to college at night, so I was ... I would fix laser printers and build networks. This is before the internet existed. You would have to connect computers together with coaxial cables and create what's called a local area network. And I did a couple of those jobs and it was well-paying and it helped me pay for college, 'cause remember, my dad had no money, so I had to pay for all this on my own. Took me five years to go through school at night. But when I would ride the train in, I would look at people reading magazines, and then I would go to cafes, 'cause bef- you know, sort of pre the web and mobile phones, and we would go hang out in cafes, you know, in the Lower East Side, Bleecker Street, wherever, the Village. You know, when I was in college, we'd go play chess on Bleecker Street, or read magazines, or free m- newspapers. And I just looked at the people who were in the pictures, Tim, and I was like, "W- why are they in the, on the cover of the magazine? Why, why is this person on the cover of Spy magazine? Why is this person on the cover of Paper magazine? Why are people important?" All I knew was nurses, doctors, lawyers, cops, firefighters. That, that's all I was exposed to. I didn't understand there was other stuff in the world.

    12. TF

      Mm-hmm.

    13. JC

      Then I went to school in Manhattan at night, and I would work in Manhattan during the day, and I was looking around going, "Well, who's that person getting out of that, like, limousine to go into that big tall building? What's in that big tall... Oh, those are apartments?" Like, it was really weird, like being dropped on an alien planet-

    14. TF

      [laughs]

    15. JC

      ... 'cause Brooklyn was so different than Manhattan at the time.

    16. TF

      Yeah, for sure.

    17. JC

      Brooklyn was a bunch of blue collar people. Manhattan were rich people, uh, and powerful people. And so something just clicked in my brain and I said, "I wanna be powerful. I wanna be rich. I wanna be on the cover of a magazine." And I started looking at the magazines, and then I discovered the masthead.

    18. TF

      Mm-hmm.

    19. JC

      And I saw the masthead and I said, "Wait a second. What's the, who's the publisher and the editor-in-chief? Who has more power? Who, who is this editor-at-large? That sounds more important. But wait, it's in a smaller font and lower."

    20. TF

      [laughs]

    21. JC

      And then I started to meet people and I started asking them, like, "What's this? What's that?" And I was at a party. I ran into somebody at Barneys. Somebody had invited me to a party in the basement of Barneys. And I'm talking to this guy and I said, "What do you do?" And he says, "Uh, oh, I, I work at a magazine." I said, "What magazine do you work at?" I said-

    22. TF

      Let me pause for a second. Barneys sounds fancy. How did you get invited to the party?

    23. JC

      You know what? I just was hanging out in the downtown scene where a company called Voyager was making CD-ROMs, Blender was making CD-ROMs. A friend of mine, Josh Harris, was doing Pseudo, and he was doing-

    24. TF

      Mm-hmm

    25. JC

      ... online chat rooms with Prodigy. So I was just hanging around with the tech scene there, and it was probably 50 people who were in the tech scene, 'cause the only thing that existed were online services, dial-up, CompuServe, Prodigy, The Well. It was just a small set of dial-up services, and I knew how to use a modem and I knew about the internet, so I kind of started to meet those people. And then those people started to tip over into the media business in New York.

    26. TF

      Yeah.

    27. JC

      And because the media business was very attracted to, "Oh, you can dial up and read an article?" People started to put these connections together, magazines plus a dial-up service, music plus a dial-up service, booking a f- a ticket to a movie, a dial-up service. So it, and oh, a CD-ROM has a video on it, or it has a, an article, so you could make a CD-ROM with an article end. So this multimedia thing happened, and then I was at Sony setting up their computer networks when the internet happened. And then Sony was gonna build a website, and so I was on the website team.

    28. TF

      Mm-hmm.

    29. JC

      And the website was a picture of 10 Sony logos, Sony Music, Columbia Records.

    30. TF

      [laughs]

  6. 24:06 – 28:51

    What happened when Jason got fired from his own company.

    1. TF

      Yeah. So let's talk about another holy shit moment, and this is January of '99. You're offered 20 million, I believe.

    2. JC

      It's a true story.

    3. TF

      And the commerce business. So- I'm reading here, this is from Fast Company, and it talks about your interaction with Douglas Rushkoff.

    4. JC

      Oh, Doug Rushkoff. Yeah, my friend in New York.

    5. TF

      Yeah, yeah, yeah.

    6. JC

      That was another guy who taught me so much. I love Doug.

    7. TF

      So walk me through getting this offer, the conversations you had, the decision you made, and then what, if anything, you kind of take from that to this day. If you wouldn't mind.

    8. JC

      The magazine had gotten very big, and it became a color glossy. I had almost 100 people working for me. It was 300 pages, and it was during the dotcom boom. We're, we're talking about 1999 now, right?

    9. TF

      Yeah.

    10. JC

      So the magazine is doing, you know, six, seven, eight million a year. I had done an event or two. That started making two or three million. So now we're at, like, I got $11 million company I'd built off my credit cards. A- and I was making, just, you know, a couple years earlier, minimum wage to work in the computer room at, uh, Fordham, which was 3.50 an hour. And then I was fixing laser printers for $9 an hour, and then I got a job at Amnesty International doing their internal network for $12 an hour. So all this happens in a very short period of time. And, you know, again, for a poor kid from Brooklyn, I'm just trying to navigate it. And this guy, Alan Meckler, had internet.com. He took it public, it became worth a billion dollars, and he offered me 20 million bucks for Silicon Alley Reporter. But it was my identity.

    11. TF

      Yeah.

    12. JC

      And it was making 10 million, and I was like, "I don't want to give up my identity." But I had thought about it, and I said, "Well, if I can ma- if I can clear a million or $2 million a year off the magazine in profits, it'd be the same amount of money, so maybe I won't do it." And then the dotcom bust happens and I lose everything, and I wind up selling the scraps of the business to Dow Jones, and they give me two years of salary, and the magazine's dead, and I get two years at $300,000. Maybe like, five or $600,000 in, like, this employment agreement, and they paid off all the bills, 'cause I then had, like my dad, I was in arrears when the magazine collapsed. If you got a magazine about the internet and the internet collapses.

    13. TF

      [laughs] Tough business.

    14. JC

      Not only did I not have any money, all the money that was owed to me never showed up.

    15. TF

      Ugh.

    16. JC

      'Cause all the companies had gone out of business.

    17. TF

      Yeah.

    18. JC

      So I was like, "You owe me for three ads." They're like, " [laughs] The phone number didn't pick up." Like, "The company was shut down." Then I show up for work at Dow Jones and they say, "Hey, can we take you for a walk?" Like, manage- middle m- manager guy. And I'm like, "Sure. A walk? Okay. Sure. We'll go for a walk." He goes, "Hey, listen, you know, you're so talented. We don't think, you know, this is... We can, you know, you being here, and you're so talented." And I'm like, "Yeah?" And they're like-

    19. TF

      [laughs]

    20. JC

      ... "So, you know, like, you should go do something else." And I'm like, "Are you firing me?" And they're like, "Yeah, we don't need your services." I was like, "You just bought my company." And the 20, you know, I had like 20 people left, and they, I reassigned them to this other venture capital thing they were doing. I said, "You don't want me, Jason Calacanis, the Silicon Alley Reporter, to work here?" They said, "No." I said, "I just signed a contract with you for 600, you know, five or $600,000." They said, "Yeah." And he pulls out an envelope, and he hands me a check for $500,000.

    21. TF

      [laughs]

    22. JC

      He says, "We're paying out your contract."

    23. TF

      [laughs]

    24. JC

      Tim, you're the first person I've, I told these stories to in a while.

    25. TF

      Wow. Wow.

    26. JC

      This is, like, literally, like, the crazy life I've lived. And I am looking at a $500,000 check, which, which is a extraordinary amount of money, obviously.

    27. TF

      Yeah.

    28. JC

      And the only thing I can think is, "I wanna beat the shit out of this guy."

    29. TF

      Ugh.

    30. JC

      "Just fucking fired me."

  7. 28:51 – 32:28

    Orchestrating a comeback the very next day.

    1. JC

      The next day. I was like, literally got an office share in one of my friend's office. I said, "Can I get a desk?" And it was like, you know, it was like that blank sheet of paper in 2002, 2003. I gotta figure something out. What's next? And I just started making designs on whiteboards.

    2. TF

      Yeah. I was gonna ask, like, that day, how do you even begin with such a blue sky blank page?

    3. JC

      Yeah.

    4. TF

      How did you even start? Were you just pulling from random bits and pieces floating around? Did you have some approach?

    5. JC

      I started calling people up. I started calling people up, "What are you working on? What's happening?" And then, you know, like, this one person was making this photo sharing site, Flickr. Another person was doing a bookmarking site called Delicious. There was just this little underground of people who were building stuff for the web, 'cause the web had gotten advanced now in the second decade and the webpages could refresh themselves with Ajax, and there were kinda tables got, became more responsive, and there were all these, like, new technical things, and then editorial formats people were playing with. And I was like, "Huh. Who's doing anything?" And then there was this, like, one group doing, like, journaling on the web. There was another group that was, you know, trying to do, like, photo sharing and follow your friends. Just like, "Huh." And then I had somebody who had worked for me named Rafat Ali, and he had started like a blog-

    6. TF

      Now, let me interrupt for one second. So the reason you're calling these people is not because you want to work with- With them on what they're doing necessarily?

    7. JC

      Yeah.

    8. TF

      Or was it? Or w- or were you just l-

    9. JC

      No

    10. TF

      ... trying to get a read of the landscape

    11. JC

      ... it was more like hey, I was literally just trying to network with people-

    12. TF

      Mm-hmm

    13. JC

      ... who I had known, and I was literally asking people, like, "What's going on?"

    14. TF

      Mm-hmm.

    15. JC

      Like, what, is anybody doing anything cool?

    16. TF

      Yeah.

    17. JC

      And I just started looking for people doing cool projects, just to see w- what was gonna happen after the dotcom bust, 'cause everybody quit and everybody went and got jobs at-

    18. TF

      I get it

    19. JC

      ... good companies.

    20. TF

      So you're trying to get a read of the l- of the playing field to see where the puck-

    21. JC

      Yes

    22. TF

      ... might be going next.

    23. JC

      Exactly. Is there anything interesting in the world?

    24. TF

      I'm mixing my sports metaphors [laughs] but you get the idea.

    25. JC

      Yeah.

    26. TF

      I'm talking about field hockey, everybody. Yeah, yeah, okay. [laughs]

    27. JC

      Let's just say, like, Tim Ferriss, when he learns a sport, it's wild to watch.

    28. TF

      [laughs]

    29. JC

      Watching Tim Ferriss learn a sport-

    30. TF

      Oh, yeah

  8. 32:28 – 36:20

    The Mercury Club that never was.

    1. JC

      cafes and stuff. I was just, like, all kinds of crazy little ideas, and I started whiteboarding stuff. I started... Cosmo had gone out of business, the delivery service.

    2. TF

      Mm.

    3. JC

      So m- the first idea I had was for Mercury Club, and I was gonna get 100 New Yorkers and give them Mercury Club number 1, 2, 3, 4, 5, all the way to 100. I was gonna give one to Charlie Rose, one to Howard Stern. And my idea was to get a bunch of people on Vespas, 'cause I had gotten a Vespa, and I was driving around New York, and I realized, 'cause I had driven one in Barcelona, I was like, if you're in a city, a bike's too slow, a car's too slow, and a Vespa goes fast, 'cause you can just weave in and out of traffic. And I, I'd seen Cosmo had started experimenting with Vespas, and I said, "I'm gonna create a service where you pay $100 a month for rich people, and you get four hours of deliveries."

    4. TF

      Hmm.

    5. JC

      25 bucks an hour. This is when, you know, minimum wage was six or seven bucks, but this is only for rich people. And if you needed a bottle of wine or a pack of cigarettes, whatever, you would just call an 800 number, 'cause 800 numbers were another, like, platform. Like, they became zines for a while, 1-800-FLOWERS, 1-800-MATTRESS, 1-800-everything.

    6. TF

      Mm.

    7. JC

      And so I started looking into buying a 1-800 number. And 'cause I was just always very interested in mediums, right? 'Cause if you get to a medium first, you can exploit it.

    8. TF

      Yeah.

    9. JC

      Whether it's podcasting, like you and I did, or blogging, like I did, and you did, I think, or-

    10. TF

      Oh, yeah

    11. JC

      ... zines.

    12. TF

      Started in 2005, blog, yeah.

    13. JC

      Yeah. So, like, if you get to it first, you get to play with it first, you get a disproportionate amount of credit for being there first, just like, you know, if you go to Austin first or you go to-

    14. TF

      Yeah

    15. JC

      ... you know, Bed-Stuy, Brooklyn first. You get the cool loft that you bought for nothing, and then everybody else comes, and your loft goes up in value, right? So the value of the platform goes up as the people who tinker and create it get to play with it, right? So-

    16. TF

      Hmm

    17. JC

      ... I never really actually thought about it, but it is true.

    18. TF

      Yeah.

    19. JC

      And so I also got the 800 number, so like, yeah, 1-800-MERCURY, I said, trying to get a Mercury Club number. And my idea was, the reas- ... 'Cause I remember talking to the guy who had done Cosmo, 'cause I covered it in my magazine, and he said, "Yeah, I just, I should have just charged a delivery fee." 'Cause he, the last six months they started charging a delivery fee, and he said, "Yeah, the business worked in three of the nine cities."

    20. TF

      Yeah.

    21. JC

      "If I had only charged delivery fees." I was like, "Why didn't you?" He's like, "VCs told me not to. I just want it to grow."

    22. TF

      [laughs]

    23. JC

      "I'm trying to get public." This is literally the same lesson people are learning now.

    24. TF

      Yeah. [laughs]

    25. JC

      So I was like, well, wait. Instead of ch- charging a delivery fee, why don't I just make it, like ... 'Cause I knew bike messengers. Bike messenger culture was, like, a big thing in New York. So the bike messengers used to hang out outside where my loft was because it was business, commercial loft at the Starrett-Lehigh Building. In New York, it was, like, commercial and we were living there illegally. Me, DJ Spooge, a couple of our [laughs] artists were living in these illegal lofts. Anyway, the bike messengers were out there all the time. They were always smoking weed and just, it was like, it was like a very cool culture because they had figured out life. They would make, like, 10 bucks per run. They could do two runs an hour, and they got to just bomb these bikes all over Manhattan, and they got exercise, they were fit, they were smoking weed, listening to music.

    26. TF

      [laughs]

    27. JC

      It was, like, the coolest gig ever. I was like, these guys, they figured out life.

    28. TF

      Yeah, yeah.

    29. JC

      Like, you get to ride your bike all day, smoke dope, listen to cool music, joke with your friends, and you just drop off an envelope now and again, and, and you're making more money than the people you're dropping off the envelope to.

    30. TF

      [laughs]

  9. 36:20 – 37:46

    The origin of “Calacanis.”

    1. TF

      So Greek- Your name is Greek. What does your last name mean?

    2. JC

      Calacanis.

    3. TF

      Calacanis.

    4. JC

      Yeah. So Calacanis means to have done well.

    5. TF

      Uh-huh.

    6. JC

      Or good for you. So sometimes when I use my credit card and a Greek person does it, they're like, "Good for you," or, "You've done well. Oh, very nice." But it's with K's. So when my grandfather went through Ellis Island, God rest his soul, they were like, "Calacanis, here's your banana. Keep moving."

    7. TF

      [laughs]

    8. JC

      And he was like, "No, it's K's." And they were just like, "Fuck you, Calacanis."

    9. TF

      [laughs] Here's your banana.

    10. JC

      They used to give you a f- No, they used to give bananas at-

    11. TF

      What?

    12. JC

      ... Ellis Island, I understand.

    13. TF

      That's real?

    14. JC

      Yeah, it was like some weird thing-

    15. TF

      Fuck that

    16. JC

      ... where they just would give everybody who comes in, like, a banana 'cause they were hungry off the boats, and bananas were, a lot of bananas were coming in from South America to Ellis Island as well.

    17. TF

      Wow.

    18. JC

      So they're just like, "Here, have a banana. Keep moving." [laughs]

    19. TF

      Today I learned. Keep it moving.

    20. JC

      And then the crazy thing, Tim, is I, I was on, uh, the Ellis Island website.

    21. TF

      Uh-huh.

    22. JC

      And on the Ellis Island website, I searched for my last name, and they had archived everything, and Calacanis, my grandfather, went through, like, 12 times. And it turned out-

    23. TF

      Huh

    24. JC

      ... he was in the Merchant Marines. He was an engine captain, and, and I knew that. But every time he came back to America with human passengers-

    25. TF

      Huh

    26. JC

      ... he had to sign in again. And so he has gone through, like, 12 times.

    27. TF

      Wow. That's wild.

    28. JC

      Yeah. And I was like, wow, he's coming from Brazil. He's coming from Ireland. He's coming from Italy. He's coming from everywhere in the world. The cargo was humans. It was Americans.

    29. TF

      That's incredible.

    30. JC

      Pretty crazy, right?

  10. 37:46 – 43:28

    Building a blogging empire.

    1. JC

      So anyway, I'd watched the blog stuff happen, and two people who had worked for me, Shani Jardan was my event producer. Uh, she had been working for a famous law firm, Latham Watkins. They were a sponsor of one of my events. She did a great job at the event. I asked Latham, "Can I hire her? 'Cause she's awesome and rad," and I hired Shani to come work with me at Silicon Alley Reporter. She would produce my events. And then when everything shut down, she started working on this, like, Boing Boing thing.

    2. TF

      Yeah.

    3. JC

      And I'm like, "Boing Boing? What are you doing with your life?" She was like, "Yeah, we write blog posts." I'm like, "Blogs? Blogs?"

    4. TF

      [laughs]

    5. JC

      And I, I was like, like, Rafat Ali was doing, 'cause this kid who had worked for me, Rafat Ali, was doing a blog on the site called paidcontent.org. And, uh, somebody ratted him out when he was working at the magazine.

    6. TF

      Yeah.

    7. JC

      That he was moonlighting. Now, back in the day, you couldn't have a side hustle. That was, like, instant firing.

    8. TF

      Yeah.

    9. JC

      So I call him into my office. I'm like, "You got something to tell me, kid?" He's like, "No." I'm like, "You sure you don't have anything to tell me?" He's like, "Is it about PaidContent?" And I'm like, "Yeah." I'm like, "What, what are you doing?" He's like, "I'm just writing about people who are charging for content on the internet." I'm like, "Hey, kid, information wants to be free. Nobody's paying for content on the internet." He goes, "Actually, I think you're wrong." I'm like, I said, "Hold on, kid."

    10. TF

      [laughs]

    11. JC

      "Let me stop you. Number one, nobody's paying for content. The whole reason we started the internet is information wants to be free. Number two, you're not a great writer. I'm your editor. Who's your editor for paidcontent.org?" And he goes, "I don't have an editor. It's a blog." I're like, "No publication will ever work if there is not an editorial structure."

    12. TF

      [laughs]

    13. JC

      "It will fail because there'll be spelling errors. You're gonna write stupid headlines. You need an editor. That's how this works." He's like, "Am I fired?" I'm like, "No, just focus on work and stop doing stupid shit on the weekend. Back to your desk."

    14. TF

      [laughs]

    15. JC

      I just, like, admonished Rafat. Now I'm an investor in his company now, Skift.

    16. TF

      [laughs]

    17. JC

      But that incepted in me, because when we shut down, I had talked to Shani, and I talked to Rafat, and Raf was like, "Yeah, I'm making, like, four grand a month on ads." I'm like, "I was paying you 35K. You're, you're making 4K now? You're making $48,000... You're making $13,000 more than when you worked for me?" And then Shani's like, "I'm getting a 5K draw a month."

    18. TF

      Yeah.

    19. JC

      I'm like, "What?"

    20. TF

      [laughs]

    21. JC

      I'm like, "How, how many hours a day do you work?" She's like, "Like, I do, like, two hours in the morning, and then, like, at night I come home. I do, like, two or three hours." I was like, you know, this is before the 4-Hour Workweek revolution.

    22. TF

      [laughs]

    23. JC

      And this is during the 60-hour reality of being a workweek.

    24. TF

      [laughs]

    25. JC

      And I was like, "Blogs, huh?" And then I started reading blogs, and I was like, "You know? There's something here. Blogs are dope." Blogs, even though they have spelling errors in them, come out faster than magazines and newspaper articles. They're faster, and faster is always better. It's faster. I said, "And for the right writer, it's spicy." Like, ooh, Shani's spicy. And I remember, like, I wouldn't have let her, her write that. I would've stopped her. And then I was, then it j- you know, w- just like when I saw all the magazines and everybody had them, I just all of a sudden, the Terminator, everything clicked at once, Tim. I was like, "It's faster, and it's better. It's faster. It's better. It's cheaper. Faster, better, cheaper. Wait." I had heard Marvin Minsky and Kevin Kelly and all these guys at, like, a conference, like, a TED at some point, talking about faster, better, cheaper. I didn't understand what they meant, but literally was at, like, TED, and they were at, like, one of Brockman's dinners, and they were talking about faster, better, cheaper, whatever, pick two, and I don't, I, I didn't understand what they were talking about. But it, it ki- kind of another inception moment. I was like, "Wait a second. What if you had 100 of them?" So then I, I called Brian Alvey, who had worked with me on the magazines, and I said, "Let's go to the Knicks game." Went to the Knicks game, and I said, "What if we had weblogs?" They, blogs were originally called weblogs 'cause they were on the web, and they were logs, and then people dropped the W-E, and they became blogs. You remember all this, but a little history lesson for those listening. And so I was like, "What if we did weblogs for business? Nobody's ever done a business topic. So we'll do weblogs." And he goes, "Oh yeah, we should call it Weblogs Inc." And then he got the domain name, and then we started building them. And we did a weblog on Wi-Fi. We did a weblog on Apple. And then we started building all these ones. And in under, in 18 months, we had built 87 blogs. We had $200,000 in total revenue, and AOL bought it for $30 million.

    26. TF

      [laughs]

    27. JC

      And we had one investor, my friend Mark Cuban, had put $300,000 in. For 20% of the company or something, and I gave him 6 million back, and then Brian and I and, uh, Peter Rojas split the rest. And, uh, in 18 months after my $20 million offer had gone away, I got the $30 million offer. And-

    28. TF

      F- that's just insane. That's just insane

    29. JC

      ... so the, the berserker insane JCal, "I'm gonna prove it to the world," proved it. And then I was like, "Yeah," I just like looked at the sword, took the armor off, hung it up. And I was like, "Yep. I can do it. I can do it anytime I want."

    30. TF

      Mm.

  11. 43:28 – 47:37

    Finding blog writers.

    1. JC

      They weren't wrong. [laughs]

    2. TF

      They weren't wrong.

    3. JC

      They weren't wrong.

    4. TF

      They weren't wrong. Just a couple of maybe boring housekeeping questions.

    5. JC

      Yeah, sure.

    6. TF

      I'm thinking of the timing of building these weblogs.

    7. JC

      Yeah.

    8. TF

      How did you find the writers to do this?

    9. JC

      A great thing for people to understand right now in this moment of time, we're, we're taping this in 2022, the market crashed and, uh, f- Facebook laid off 11,000 people yesterday. Yeah, I don't wanna date this too much. I don't know when you're gonna run this.

    10. TF

      Oh, that's okay. It'll come out reasonably soon. I mean, but people, as, as a snapshot in time also, I mean, crypto's having a complete implosion. FTX is going through the meat grinder. People are probably gonna go to jail.

    11. JC

      Yeah, jail, $32 billion eviscerated. I actually wanted to talk to you about, like, people who commit fraud and lie, 'cause I was interested in your perspective on it. 'Cause I just can't imagine it, because the system is so easy to win.

    12. TF

      Yeah.

    13. JC

      And the system is set up for entrepreneurs to win in this country. Like, why on earth would you cheat if it's so easy-

    14. TF

      Yeah

    15. JC

      ... to just have a win by just working hard? Anyway.

    16. TF

      But I interrupted you, because you were, you were tying the weblogs and artists and so on.

    17. JC

      So it's very simple. Everybody was out of work.

    18. TF

      Ah.

    19. JC

      And so I just would ... When you hired a writer, you'd say, "Do you know anybody?" And the original deal was, we started going to people who were doing, like, live journal blogs.

    20. TF

      Mm-hmm.

    21. JC

      And, like, we'd find somebody who had written a blog about Apple. Sean Bonner.

    22. TF

      Yeah. Sean Bonner. Yeah.

    23. JC

      Yeah. And I said, "Hey, Sean, um, I'm doing this Weblogs Inc. thing. We're gonna try to sell ads on blogs." He's like, "Well, that's stupid." I'm like, "Yeah, but I think I can figure it out, 'cause I did a magazine." He's like, "All right, that's pretty smart." I was like, "Would you write ... I see you're writing some Apple blogs. Could we put them on our Apple blog? Uh, or if I gave you the login, would you post them?" 'Cause Brian Alvey, who's a genius, he's now running WordPress for, for Matt Mullenweg.

    24. TF

      Oh, no kidding.

    25. JC

      Uh, WordPress, like, pro VIP that you, like, people like you and I use.

    26. TF

      Yeah, yeah, yeah. At Automattic, yeah.

    27. JC

      At Automattic. And so anyway, he's, like, a great collaborator of my career. He's kind of my, uh, George Harrison or-

    28. TF

      Yeah, yeah

    29. JC

      ... Paul to my Lennon or vice versa. He had built the software that was better than everybody's. Better than Typeform, better than Blogger, better than everything. And, uh, I just gave Sean the login, and I was like, "Listen, I wanna pay you something, because I want to own the blog posts." He's like, "You wanna own a paragraph of me writing about a MacBook."

    30. TF

      [laughs]

  12. 47:37 – 53:30

    Planning events and making memories.

    1. JC

      era.

    2. TF

      I mean, 30 million today would still be a, a good chunk of change. So let me flash forward.

    3. JC

      Mm.

    4. TF

      And I wanna ask you specifically, because it came up already, about events. So you seem to love producing events, and you've produced a lot of events.

    5. JC

      Yeah.

    6. TF

      I have only produced one event.

    7. JC

      In Reno? Oh, Tahoe.

    8. TF

      It was in Napa.

    9. JC

      Oh, it was Napa.

    10. TF

      Long ago.

    11. JC

      I have a friend who went. She loved it.

    12. TF

      Yeah, it was a great event.

    13. JC

      People still talk about this event. Somebody brought it up last year.

    14. TF

      They do. They do. It was called Opening the Kimono, OTK. I actually have a wine bottle from that event over there, 'cause we made a ... We had a wine-making competition that the participants all engaged in, and then we took the winner and we bottled whatever it was, 200 bottles, and gave them to everybody. So it was incredibly elaborate, and I came out of that feeling like I had, had just finished a tour of duty. It was so hard. Why do you love doing events, and what is the smart way to do it? What is the JCal recipe?

    15. JC

      In the Myers-Briggs, I'm gonna say you're INTJ or INTP

    16. TF

      Nailed it. INTJ

    17. JC

      Yeah. But I could see you being a perceiver, but anyway, I'm ENTJ. And so you and I vibe until such time as I absolutely exhaust you and you need to go to your room [laughs]

    18. TF

      [laughs]

    19. JC

      and take a deep breath. That's the relationship between INTJs and ENTJs. Like, uh, this is, for people who don't know the Myers-Briggs, which is, uh, or, or as we call it, astrology for men.

    20. TF

      Yeah. [laughs] Yeah, that and the Enneagram. Astrology for men. [laughs] Yeah, that's basically it.

    21. JC

      Like, we don't believe in astrology, but we believe in this other thing where we answer questions and it tells us-

    22. TF

      [laughs]

    23. JC

      ... things we wanna hear about ourselves. But anyway, uh, I scored 86 and 100% on extroversion the two times I took it.

    24. TF

      Yeah.

    25. JC

      So I'm so extroverted that when I'm with an introvert like yourself, or like say Evan Williams, a friend of ours-

    26. TF

      Yeah

    27. JC

      ... like, I can burn people out. I'm just r-

    28. TF

      [laughs]

    29. JC

      I wanna talk for seven hours.

    30. TF

      [laughs]

  13. 53:30 – 1:01:12

    Friendship, loyalty, and collaboration with close friends.

    1. TF

      So let's talk about friendship, because there are a few things that come to mind when I think J Cal and friendship.

    2. JC

      Mm.

    3. TF

      I wanted to actually sidestep and just mention something that ties back to a few things you said that I was gonna bring up later, but I'm just gonna ... We'll, we'll bookmark this one, but this is a quote from October 2008 when a lot of shit was going down. People may or may not remember. If you weren't, uh-

    4. JC

      Yes

    5. TF

      ... aware of it, a lot of things were-

    6. JC

      Oof

    7. TF

      ... imploding, and your quote at the time in The Guardian is, "Everybody else is going to be depressed and drinking and not working, so it's a great time to be an entrepreneur." So that ties into [laughs] a lot of what you already said.

    8. JC

      Yeah.

    9. TF

      But on friends, I wanna say two things, uh, related to that. The first is, let me find this w- amazing quote. All right, so this is a quote from Douglas Rushkoff. Yes, exactly.

    10. JC

      Oh, this is a good one.

    11. TF

      Yeah, I think-

    12. JC

      I put this on the back of my book. [laughs]

    13. TF

      Yeah, yeah, yeah. "Jason would never stab you in the back. He might stab you in the face, though."

    14. JC

      [laughs]

    15. TF

      So I really admire you as a friend, and this is not just for me, this is related to other people, because you are one of the most loyal friends I have come across in my adult life, and I've seen you defend your friends in so many circumstances where- A, you don't have to, out of pure self-interest. B, there's a very good chance it's never gonna get back to the other person.

    16. JC

      Hmm.

    17. TF

      So I have a question for you, and, uh, maybe that'll be the first one about loyalty. The second question, because I do wanna talk about All-In, is going to be how you navigated starting a project with your very close friends.

    18. JC

      [laughs]

    19. TF

      And all the conflict that ensued, because I have always avoided working, by and large, with my friends.

    20. JC

      Yeah.

    21. TF

      So loyalty, where does that come from and why? And then, then the navigating starting a project with your close friends.

    22. JC

      Well, so much of what makes us who we are is, I think, formed in childhood. So when you're a kid, I think you have this, like, computer hard drive operating system, and things start getting written to it. And one of the things that my dad wrote into it is like, "Hey, you and your brothers, you're the Three Musketeers. You gotta be there for each other. Loyalty above everything else. You always have to have each other's back." And that wasn't just, like, his operating principle. It was, "You're gonna get in a fight on the way to school. We live in Brooklyn. This is a dog-eat-dog world. I wanna make sure that you two, you never leave your brothers behind." So that was, like, one of his rules. Like, if he saw two of us and one of your, "Where's your brother? Go get your brother." Doesn't matter if it's the oldest, the middle, I'm the middle, or the youngest, "You three have to be by each other's side all the time. Never leave one of your brothers behind. Never let anybody say anything to your brother. Always fight." It was, like, one of the great things my dad taught me, and it stayed with me. And over time, what I realized was one of my superpowers is being there for my friends and being a loyal friend. But I guess the Doug Rushkoff quote. [laughs]

    23. TF

      [laughs]

    24. JC

      You know, I might be full contact at times, where if I disagree with somebody or-

    25. TF

      [laughs] At times

    26. JC

      ... at times, I might be like, "I don't agree with you," or like, "That's stupid." Um, the-

    27. TF

      Timmy, that's the ugliest layup attempt I've ever seen. [laughs]

    28. JC

      Jesus. [laughs]

    29. TF

      What the fuck is wrong with you?

    30. JC

      What the fuck is wrong with you? [laughs]

  14. 1:01:12 – 1:09:02

    All-In: When a solo act gets tricked into joining a band.

    1. JC

      All-In-

    2. TF

      [laughs]

    3. JC

      ... i- it's a very interesting thing, because, uh, you and I are solo acts.

    4. TF

      Yeah.

    5. JC

      And, uh, you have one duet you do. It's my favorite part of what you do, is, uh, the Random Show with Kevin. Literally has had a profound impact on my life.

    6. TF

      Oh, wow.

    7. JC

      A big part of why I lost 30 pounds this year. You were telling me how good I looked.

    8. TF

      Mm-hmm.

    9. JC

      But I was in Italy a couple of summers ago, and you and Kevin were talking about Ozempic.

    10. TF

      Uh-huh.

    11. JC

      And you had taken Ozempic and puked. And I went to my doctor and I talked to them about Ozempic, like a TV commercial. And I haven't talked about this previously, 'cause I don't wanna influence people, but I did a couple of, you know, series of Ozempics, along with fasting that I learned about from you and Kevin, and using the Zero fasting app, which I learned about from the show. And then I, uh, obviously hear you talk about weightlifting and the impact that has. And so for the past year or so, I just did the Tim Ferriss Kevin Rose program. I did a couple cycles of Ozempic. I did the weightlifting, and I did the intermittent fasting using the Zero app. And, uh, yeah, dropped 30 pounds.

    12. TF

      Yeah. You look great, man.

    13. JC

      Thank you.

    14. TF

      I said it before we started recording. I was like, "You look really, really good. Well done."

    15. JC

      I'd like to get 5 or 10 more pounds of weight. Oh, you know, of, like, muscle.

    16. TF

      Yeah.

    17. JC

      Uh, and then be able to run a marathon again. So if I can get those two goals, that would be pretty happy.

    18. TF

      You can do it. You can definitely do it.

    19. JC

      I'm in the window.

    20. TF

      Yeah. So solo act suddenly decides, "Wait a minute, I wanna be in a rock band, but I, I may not be allowed-"

    21. JC

      Did not decide that, actually. [laughs]

    22. TF

      No. [laughs]

    23. JC

      Got kind of pushed into it.

    24. TF

      Okay. Well, all right.

    25. JC

      If I'm being honest.

    26. TF

      So tell the story.

    27. JC

      Yeah. What happened was, uh, Chamath-

    28. TF

      Yeah

    29. JC

      ... and I had become friends. Chamath Palihapitiya, and I had known-

    30. TF

      And you should explain, if people have no context, what is All-In? What is the premise of the podcast?

  15. 1:09:02 – 1:17:10

    Memorable times All-In has gone off the rails.

    1. JC

      have three partners, and all three of my partners on it have never had a boss.

    2. TF

      [laughs]

    3. JC

      So you've literally got four of the most opinionated friends who've never had a boss, who have four different directions they wanna take it, and it is a bit chaotic. And I'm the producer of it as well-

    4. TF

      Yeah

    5. JC

      ... and, you know, did all the work, came up with the format, et cetera. But objectively, you know, Chamath has his series of fans, Friedberg now has his stans, Sacks has the whole right wing. So it's like a super team has come together.

    6. TF

      Yeah, yeah.

    7. JC

      And it's very hard to keep a super team together for any period of time, and this thing has come off the rails famously, like, two or three times.

    8. TF

      Could you walk us through your favorite of those three times and how it was resolved?

    9. JC

      Well-

    10. TF

      [laughs]

    11. JC

      ... I wanted to do an event, 'cause you mentioned before I like events, and I was like, "Let's do this All-In Summit. I'll do all the work and, uh, you guys show up. I have a production team, and, you know, here's what it will be." And one of the four of us was in a complete panic, and complaining, and arguing incessantly, 'cause he thought I was going to ruin their reputation because what if it's not great? The thing comes out of the gate, people are comparing it to the TED Conference, saying this is better than Recode or better than TED, and it's the new TED and whatever, because we got the most incredible speakers in the world showed up for us. Just everybody. Uh, I invited you, you didn't make it, but I'll get you next year.

    12. TF

      [laughs]

    13. JC

      Maybe. I don't know if I can afford your speaking fee.

    14. TF

      [laughs]

    15. JC

      But, uh ... [laughs]

    16. TF

      If it makes you feel any better, I know, I remember this, and I have not done any speaking except for South by Southwest, I wanna say in three or four years. Yeah. So, but-

    17. JC

      No, there'll be some opportunity-

    18. TF

      What's on?

    19. JC

      ... where we'll, like, it'll be a fun thing for us to do.

    20. TF

      And in my own defense, I have been to events of yours before. I've gone to-

    21. JC

      Yeah

    22. TF

      ... I have spoken with you at, at events. So I couldn't make that one.

    23. JC

      Yes, you did one of mine.

    24. TF

      Yes. Okay. All right. So wait, where does the conflict come in?

    25. JC

      So the conflict came in that I just told him, like, "Hey, listen, I'm working over here."

    26. TF

      [laughs]

    27. JC

      "You need to shut the fuck up and let me just do my work, and stop being in a panic attack all the time." And he's like, "My reputation." He said, "Eh, what if it's bad? We pa- people paid $7,500 a ticket." I'm like, "Some people pay $7,500 ticket for every event. Like, it's not a big deal." And then I, um, gave half the tickets for scholarship for people. Anyway, we had this back and forth, and then I told the person, like, you know, Friedberg, I was like, "Friedberg, if you don't wanna be on the show and you're complaining so much, I got Brad Gerstner over here."

    28. TF

      I love how he was anonymous up until right now. [laughs]

    29. JC

      Whatever. The, the good news is, Friedberg and I, after this blowout, like many friendships, we actually are really enjoying our time together. But it was another one of these, like, stab you in the back, stab you in the face thing.

    30. TF

      [laughs]

  16. 1:17:10 – 1:23:14

    With greatly followed podcasts comes great responsibility.

    1. JC

      chaos. And because the podcast is so popular, Tim-

    2. TF

      Mm-hmm

    3. JC

      ... it's, it's like a lot of things, like people maybe give it a little too much credit.

    4. TF

      You start to have a very big responsibility.

    5. JC

      Now it's become a responsibility.

    6. TF

      Yeah.

    7. JC

      And that, exactly. You nailed it. That's what I was thinking.

    8. TF

      Yeah.

    9. JC

      Like, now people are calling me saying, "Hey, you gotta get Sax in line." And then people are calling Sax saying, "Oh, JCal hates Trump. He's got Trump derangement." I mean, everybody's projecting into this while we're just having a conversation. Like, hey, what gives you the right to have a conversation about Ukraine? What gives you a t- a right to have a conversation about affirmative action in this Harvard case, right? What gives you the right to talk about masks and COVID? And what I tell people is, when we talk about things in our wheelhouse, capital allocation, company formation in the markets, take notes. We're experts. Totally awesome. We've been at it for over a century combined. Great place for you to learn if you wanted to be a venture capitalist, entrepreneur, or bet on the markets. Totally get it. When we talk about anything else, COVID, Ukraine, politics, we're as informed as you, maybe a little more, maybe a little less. You're listening to four people have a conversation. Go do your own research. Go find your own truth. And what we found with COVID specifically, which was kind of ironically where this whole thing started and what caused it to start, Fannie, Farrah, and ProPublic, I don't know if you saw this, are like, "Yeah, we intercepted some communications. It looks like it was probably a lab leak."

    10. TF

      Yeah.

    11. JC

      And we were sitting here 18 months ago, and when different people on the podcast were saying, "Well, maybe it's a lab leak," they were like, "Well, we have to take that podcast down now."

    12. TF

      Yeah.

    13. JC

      It's like, we, we can't have that conversation that it's a lab leak? Like-

    14. TF

      Yeah

    15. JC

      ... there's two labs in the world that are studying the Wuhan virus, and one of them is where the leak happened? I mean, one of them is the, when the COVID happened, it happens to be in Wuhan. Like- There's 10,000 locations in the world. Like, pretty easy jump to make, but there's some weird thing going on right now where people expect Tim Ferriss, or Joe Rogan, or David Sacks can't have a conversation and talk about a topic because their shows are popular.

    16. TF

      Yeah. Yeah.

    17. JC

      And we have to work this out because you are allowed to have a conversation, and people need to come to their own truth.

    18. TF

      Yeah.

    19. JC

      And sometimes institutions do a great job, sometimes they fail us. But we should all debate these issues.

    20. TF

      If it's helpful, I can tell you my policy on this stuff.

    21. JC

      Please, tell me.

    22. TF

      Or I say my protocol. My protocol is if I'm gonna talk about something that I know is going to light people up, but that it is important and I feel like I have maybe access to an expert who can actually speak credibly-

    23. JC

      Mm-hmm

    24. TF

      ... then I'll add in very strong disclaimers, and then I will not look-

    25. JC

      Yes

    26. TF

      ... at Twitter for at least a week. [laughs]

    27. JC

      [laughs] Yes. Some self-care.

    28. TF

      It's very simple. It's like if you don't want the cock punches, don't go to where everyone's giving cock punches.

    29. JC

      Ouch my balls.

    30. TF

      Yeah. [laughs]

  17. 1:23:14 – 1:30:41

    Keeping All-In running smoothly with four very different personalities.

    1. TF

      question, since I did call you Podcast Master in the beginning.

    2. JC

      [laughs]

    3. TF

      And I wanna, I wanna put on a showcase for a moment. So you and I have, have offline talked, well, I guess probably online, but offline meaning non-publicly-

    4. JC

      Yeah

    5. TF

      ... talked about how you prepare privately. [laughs] Jesus. What am I? Am I a writer? I used to be.

    6. JC

      Yeah.

    7. TF

      Words. Use your words, Ferriss.

    8. JC

      [laughs]

    9. TF

      Privately. So-

    10. JC

      You're a great writer

    11. TF

      ... we've talked about your moderating.

    12. JC

      Yeah.

    13. TF

      I think you're one of the best moderators I've ever seen.

    14. JC

      Aw.

    15. TF

      Uh, it's true, and I ... That is absolutely, I would say that to anyone. I think, I'm actually pretty sure I have said it publicly.

    16. JC

      You have, actually. Thank you for that.

    17. TF

      Yeah.

    18. JC

      Yeah.

    19. TF

      And I'd like to look at the mechanics and the preparation that goes into that.

    20. JC

      Hmm.

    21. TF

      Because you've talked to me about this, and I remember one of the examples, again, which is hyper-specific, which is if you guys are on Zoom, which most people are not gonna see, like raising y- your hand-

    22. JC

      Yeah

    23. TF

      ... and using visual cues for things. So could you walk through what the preparation process looks like for a good episode?

    24. JC

      We build a docket every week for All-In. The docket I took from Red Scare, which is, like, this dirt bag left podcast of-

    25. TF

      Mm-hmm

    26. JC

      ... these two women who live in the Times Square in New York.

    27. TF

      All right.

    28. JC

      They're quite charming and hilarious. Uh, probably a little cutting edge for some people. But anyway, the Red Scare podcast is hilarious, and Dasha always says, "Oh, what's on the docket?" And they have a docket. Like, you know, these are the people [laughs] we're, we're gonna pass judgment on, like, b- be- before a judge. So we have a docket. I make a docket every week with my producer, Nick, and basically we're in a group chat, and whatever links we share that week, we put in there. And then we put bullet points.

    29. TF

      So the docket is a Google Doc?

    30. JC

      Yeah, a Google Doc of topics.

  18. 1:30:41 – 1:35:26

    Talent-wrangling techniques.

    1. JC

      right?

    2. TF

      May I give one example of why they're totally different? In a one-on-one conversation, you can have a guest who monologues. If you have a group of people, that can be a huge problem. How do you deal with that specifically?

    3. JC

      Yeah, it's two techniques.

    4. TF

      Yeah.

    5. JC

      Two techniques. Very good, so you and I like technique. So the two techniques I have. One of them is I say to people beforehand, "Great job on the show today. At this moment in time, you made four really great points It would've been better if you made your first one or two, and then said, "I'm really interested in what Sax thinks of that," or, "I'm curious, Sax, what you think." And then you have those two, just write them on a piece of paper there. There'll be time for those, too. We'll circle back around. But now it doesn't look like you're taking all the chips off the table. Because in a conversation with four smart people about a topic, there might be five good points to make. All four people might understand all five points or four of the points, and then if somebody comes in and they're just like, you know, ding, ding, ding, ding, ding, "I just took all the good points." [laughs]

    6. TF

      Yeah.

    7. JC

      There's nothing left for anybody else to do. And so you wanna share the ball a little bit. You took two good points. You let somebody else make a good point. Yeah, you could've made that point. It was an obvious one, but you let somebody else have it. It's a little bit generous as a performer.

    8. TF

      Yeah.

    9. JC

      So it'd be like, you know, you, you, you got some incredible guitar player, they come out and they just do a solo of six minutes.

    10. TF

      [laughs]

    11. JC

      And you're like, "Piano guy-"

    12. TF

      [laughs]

    13. JC

      "... could've done a solo for a minute. You could've done two. We could've given the drummer a minute, and then could've let the vocalist lead off the song with an a cappella, you know, moment," right?

    14. TF

      Yeah.

    15. JC

      And so I've really tried to be better at it, and specifically tried to be better at it because people have been critical of me-

    16. TF

      Mm

    17. JC

      ... for interrupting certain people.

    18. TF

      Huh.

    19. JC

      And so I had to actually adapt to that, because certain people, if you interrupt them, it's a trigger for them.

    20. TF

      Yeah.

    21. JC

      Or it can break their train of thought.

    22. TF

      I ran into this recently, and I was like, I was w- I wondered how, like how would Jason handle this? I was curious.

    23. JC

      So I came up with another one. I said, "I'm going to give you the circle." So if people aren't watching right now, I'm just taking my index finger and I'm just giving the wrap up sign, but I'm also nodding. So I'm saying-

    24. TF

      Yeah

    25. JC

      ... "Hmm, good stuff." You know, I'm giving you the good stuff, but like, "Hey, let's wrap that point." And then I'll just stop, and they finish their thought. And the other thing I do is I just use, "Okay." And I got that from Sam Harris. I was listening to the Sam's podcast. He gets people monologuing. These are some of the most brilliant academics in the world on his show, and you'll see sometimes he wants to break in. But I think in academia it's even more, like-

    26. TF

      [laughs]

    27. JC

      ... difficult to do that, and he just-

    28. TF

      Forboden, yeah. [laughs]

    29. JC

      Forboden, that's the word I was looking for.

    30. TF

      [laughs]

  19. 1:35:26 – 1:36:42

    Bill Maher’s moderation style.

    1. JC

      about the reps, yeah.

    2. TF

      Yeah, I wanted to ask you about moderators. So you mentioned the McLaughlin group earlier. Are there any people who stand out as good moderators to you?

    3. JC

      You know, there's not a big cohort of moderators.

    4. TF

      Yeah, there aren't that many.

    5. JC

      I mean, you might say, what's his name from Politically Incorrect? Bill Maher. So Bill Maher, you know, he can drop something funny into a moderated bit. So two people are talking and, uh, you know, I, I do a little comedy on the side, and will sometimes make jokes during the podcast.

    6. TF

      Mm-hmm.

    7. JC

      And I have seen him do this particularly well. He's watching two people spar, and he's kinda set that up, and he's leaning back. Then he just lets, like, a little funny thing out. So as a device for a moderator, it's getting super heated, and then you drop something funny, and you'll see me do this on All-In, it kinda just cracks the whole thing open. Everybody's like, "Okay, that was getting really serious, but we're all humans and we can laugh too about it."

    8. TF

      Yeah.

    9. JC

      So somebody's having some crazy debate about, like, Roe v. Wade, and then he makes some joke, you know, and you're just like, "Whoa, [laughs] that's a funny joke. Oh, I can laugh about Roe v. Wade and abortion? Oh my God, I'm not allowed to laugh about that?" Like-

    10. TF

      Yeah

    11. JC

      ... that's a dicey place to be. But that comedic interruption is, it works pretty well. But there aren't many people or shows that do it well.

  20. 1:36:42 – 1:38:23

    Friendly rapport can be contagious.

    1. TF

      Yeah.

    2. JC

      I think you, you could pull it off, I think with, you know, you have your great rapport with Kevin Rose.

    3. TF

      Yeah.

    4. JC

      And if you got one or two more, y- you could do your own little All-In McLaughlin group thing. It would be quite successful, I think.

    5. TF

      Yeah, I guess it comes down to the, the chemistry, like you, like you said. Because with Kevin it's like we just, it's like having a good improv comedy partner or something. It's like w- your styles-

    6. JC

      Yeah

    7. TF

      ... just work for s- for some reason.

    8. JC

      Yes.

    9. TF

      And then you can always improve the craft and work on it, but there is just this baseline of compatible chemistry.

    10. JC

      You know, when you look at your podcast player, if I see random show- That's just like, I snipe that immediately.

    11. TF

      [laughs]

    12. JC

      Like when The Random Show comes up in my feed. Because you know what? We're going back to friendship. We talked where we've-

    13. TF

      Yeah

    14. JC

      ... kind of spent a little time in this conversation. Friendship is so special, right? Like-

    15. TF

      Yeah

    16. JC

      ... it's like one of those very special things in the world that's unique. And when people see friendship, like true friendship, it's so, it's such a, like intoxicating thing-

    17. TF

      Yeah

    18. JC

      ... to know that you and Kevin are having a great time catching up.

    19. TF

      Yeah.

    20. JC

      And we get to be there for it. It's just to... And I, and, and I do think that is a big part of why people have become addicted to All-In. And we had like one or two weeks we took off, and man, I have never had people, "I'm so depressed, I'm so ... Oh, God, what's going on? What's..." And then when the show was gonna break up, "Oh my God, what's going on?"

    21. TF

      [laughs]

    22. JC

      "This just sucks, man." I've had people wrote me very long notes like, "You know, I really think you guys need to think about the fans and what the impact this is gonna have on us." And I was like-

    23. TF

      [laughs]

    24. JC

      ... "I feel like we're in Pink Floyd and like Roger Waters-

    25. TF

      [laughs]

    26. JC

      ... and Gilmore are like doing their separate tours," and they're like, "It's the same songs, folks." Like [laughs]

    27. TF

      [laughs]

    28. JC

      You could just listen to the old albums.

  21. 1:38:23 – 1:41:50

    Can you see your comfort zone from the Overton window?

    1. TF

      I think there's another piece which is right parallel to this, and that is with friendship, with friendship on display, you get to hear people also talking as humans without overly self-censoring in a world where that has become the norm. Do you know what I mean?

    2. JC

      Yeah. No. When we had our, just now in our conversation, when we were bringing up ouch my balls from The Office-

    3. TF

      [laughs]

    4. JC

      ... and I was like, "Oh, we're going there?"

    5. TF

      [laughs]

    6. JC

      Hmm. Oh, no. Are we gonna get canceled for liking a funny bit in a movie? [laughs]

    7. TF

      [laughs] Yeah. And, and, I mean, the fact of the matter is, as, uh, I don't think anyone will disagree, like if anyone listening to this podcast had their group chats publicly shared, everything would be over, right? It's just like their chats with their five closest friends.

    8. JC

      Oof.

    9. TF

      All of us would be unmasked-

    10. JC

      Yeah

    11. TF

      ... for the complete children that we all are.

    12. JC

      Yes.

    13. TF

      And, uh-

    14. JC

      Yes. Goofballs

    15. TF

      ... despite that, given the times, I think the majority of folks feel like they have to, have to put on a mask and stuff all of that so far down because the risk seems so high. So when you have a show where friends-

    16. JC

      Mm

    17. TF

      ... are having fun, they're not taking themselves or anything too seriously, even though they do take-

    18. JC

      Mm

    19. TF

      ... things seriously in life-

    20. JC

      Right

    21. TF

      ... it allows everyone to just exhale for a second.

    22. JC

      Yeah, chill out.

    23. TF

      Take off the-

    24. JC

      It's gonna be okay

    25. TF

      ... psychological corset that they strain to put on in the morning, you know?

    26. JC

      It's very weird like being a Gen X-er where like the Overton window was so much wider when we were young, and now the Overton window, people are like, "Close it tighter. Close it tighter." And I'm like, "Who cares? It's just a window." Like you could-

    27. TF

      Yeah

    28. JC

      ... pick how wide or open you want it to be. But people are really trying to like narrow the topics you can discuss in a way that I find kind of a bummer.

    29. TF

      Yeah.

    30. JC

      You know, 'cause all those conversations are still gonna occur, they're just gonna occur in private.

  22. 1:41:50 – 1:48:51

    Transfering skills, building popularity, and co-existing with jet blockers.

    1. TF

      it.

    2. JC

      Yeah.

    3. TF

      So you have this experience with these friends. You build this podcast.

    4. JC

      Yeah.

    5. TF

      Two questions that you can pick, either or both. The first is, you mentioned capturing lightning in a bottle, and I'd be curious how you would explain the success of this show. Because there must be, you were so deliberate, so deliberate. You, every example you've given, I think from at least your earlier career, shows how systematic and methodical you are. So I don't-

    6. JC

      Mm.

    7. TF

      I know it wasn't an accident. It may have, it may have coalesced in a way that couldn't have been predicted, but n- I don't think it was an accident. So how would you, how would you explain the popularity? Like what are the ingredients?

    8. JC

      Yeah.

    9. TF

      And then secondly, how do you now think about success for yourself?

    10. JC

      Mm.

    11. TF

      And you, you'd made that joke earlier about being separated from the, you know, the private jet. Your friend's standing in the way of this private jet.

    12. JC

      Jet blockers.

    13. TF

      Yeah, yeah. How do you think, [laughs] how do you think about success and/or power? Because that played such a role in your life up to this point. So the ingredients that made the podcast successful or that make it successful, and then the, the success power piece.

    14. JC

      I think there is something that comes from, you know, repetition and getting reps in. Uh, you and I are both big fans of that. And so I think having done, you know, whatever at the time, maybe 1,300 or 1,400 episodes of This Week in Startups and all those event interviews, I came into All-In with a 10-person podcasting team. I mean, that includes some salespeople, so whatever. But having had done so many podcasts, that I came in with so much knowledge and ability, and it was like, oh, my skillset, but a different playing field. It would be like somebody who plays ping pong, all of a sudden gets on a tennis court, which happened to me. I used to play ping pong as a kid. I bought a house that has a tennis court, quite embarrassingly. Like, it's like a mind-blowing thing for a kid from Brooklyn to have a tennis court on their property. You're like, "Wait, aren't there, like, two in, for 10,000 people in Brooklyn?"

    15. TF

      [laughs]

    16. JC

      And you have to wait, like, to get on it, and then I have one where I can just sit there and, like, l- let it go unused for a month. Like, ping pong and tennis is the same thing.

    17. TF

      Yeah.

    18. JC

      There's a, there's a net, there's a ball, there's, you put spin on it. And I started taking tennis lessons this year, and it was like, woo. You know, your brain kinda lights up.

    19. TF

      Yeah, yeah.

    20. JC

      Same thing, but different.

    21. TF

      Yeah.

    22. JC

      Same skill. So I think that, it was like all that preparation had led to this new thing that you actually keyed off on, and we talked about last year for like an hour during the winter, of like, "Hey, what happened there?" And so I think that's, that was the lightning in the bottle for me personally, was I, maybe th- I'm a better moderator than an interviewer. Maybe that actually was sitting there the whole time. Maybe I'm better su-

    23. TF

      Yeah

    24. JC

      ... better tennis player than a ping pong player. So that, for me, I think has opened up a lot of possibility, of what I-

    25. TF

      Yeah

    26. JC

      ... possibilities of what I could do with the last 10, 20, 30, 40 years, whatever I got left on this planet, uh-

    27. TF

      Yeah

    28. JC

      ... before the tears and the rain moment happens. And so it has opened my aperture a bit, and I am thinking about things differently, which dovetails with your second question, which is, after I made, you know, whatever amount of millions of dollars, I had a profound realization, like, when I go out to eat with a friend who's a billionaire, me, you, and Travis were sitting around, or me, you, and Matt Mullenweg were sitting around, and we took out our net worths and it was like, "Oh my God, like, you and I are down here. These two guys are up here."

    29. TF

      [laughs]

    30. JC

      We all go and have a steak. Steak tastes the same.

  23. 1:48:51 – 1:51:54

    What happens when you catch the car?

    1. JC

      that's the thing I'm writing in my new book about is, you know, my new book is about money and wealth.

    2. TF

      Mm-hmm.

    3. JC

      And, um-

    4. TF

      Can't wait to read it

    5. JC

      ... I wanna send you some early stuff and get your thoughts on it. But I'm writing about this paradox that you and I are talking about right now, which is what happens when you catch the car?

    6. TF

      Yeah.

    7. JC

      What happens, you know, it's a- it's, it's part how do you catch the car? But then once I get you on the hook for that, like how do you get the money, now what happens when you have caught the car?

    8. TF

      Yeah.

    9. JC

      And then now you have to look in the mirror. I caught the car. Okay, the adrenaline rush is over. Am I actually happy? Did I want to catch that car?

    10. TF

      Yeah.

    11. JC

      Did I want to be Tim Ferriss? Did I want to be J Cal? Did I want to be Travis? Did I want to be Matt Mullenweg?

    12. TF

      Yeah.

    13. JC

      Is this actually making me happy? What now?

    14. TF

      Yeah.

    15. JC

      And that's where, like, Buddhism and a lot of, like, soulfulness has hit me in my 50s or, you know, right before my 40s. Basically when my two friends died. Two of my poker buddies died, and it just, it just reprogrammed my brain in a major way.

    16. TF

      Yeah.

    17. JC

      You know? Uh, those two events. And it's actually been a gift, you know, in a way, because now I just look at the world differently. It's like a, it's a big gift.

    18. TF

      Puts things in perspective.

    19. JC

      Yeah. I mean, it does really. Yeah.

    20. TF

      And, you know, another pattern I've noticed just with respect to catching the car is that not everyone, but a lot of, a lot of achievers I know who have been driven enough and worked hard enough and focused long enough and sacrificed enough to make a lot of money, when they finally cross that threshold where they're, where they, they can't really rationalize the need to make more-

    21. JC

      Right

    22. TF

      ... which by the way, I mean [laughs] not to plug my own, I haven't done this, I haven't mentioned The 4-Hour Workweek in a long time, but if you actually read some of the basics, the fundamentals in that book, it outlines just how much self-deception goes into believing that you need 20, 30, 50, $100 million. It's mostly unjustifiable.

    23. JC

      Totally.

    24. TF

      And when, uh, you get enough money that you've won the game you always thought would answer your prayers and remove all the pain, anxiety, and depression, and it doesn't-

    25. JC

      Yeah

    26. TF

      ... that is a-

    27. JC

      Oh, boy

    28. TF

      ... terrifying moment.

    29. JC

      Yep.

    30. TF

      And oh, my God, do people, and I'll include myself in this group of people-

  24. 1:51:54 – 1:58:25

    Psychedelic therapy and a big win in Colorado.

    1. TF

      the car.

    2. JC

      Yeah. And this is where doing the work internally, and I really respect the fact that you've used, you know, some of the, the resources you've gathered to do what the work you're doing at Psychedelics.

    3. TF

      Yeah. Thank you.

    4. JC

      I've never publicly talked about the psychedelic work or psychedelics period 'cause I, you know, as a person who sometimes people follow what I do, you know, with a fan base, like-

    5. TF

      Yeah

    6. JC

      ... I, I talked about, like, actually taking Ozempic for the first time. I think there's things, there's suffering in the world that psychedelics are uniquely qualified, I suspect. And, uh-

    7. TF

      Mm-hmm

    8. JC

      ... you know, you would, you'd wanna talk to a doctor and a therapist and do these things in a very considered fashion. But the fact that you're, you know, uh, looking at psilocybin and other people are looking at ayahuasca or the ketamine or whatever, I think the research and the suffering that's happening, a lot of it is because people have not done enough of the work to look inside-

    9. TF

      Yeah

    10. JC

      ... and find out where that trauma is and maybe try and clear it, and maybe try to understand it. And that is, I think, the breakthrough that's gonna happen in our lifetime because of people like you and some other friends of ours who have dedicated significant resources towards the study of these. S- I don't know if you saw Colorado, I think, passed-

    11. TF

      I did. Yeah

    12. JC

      ... 122 yesterday.

    13. TF

      Yeah. That's big news. Very big news.

    14. JC

      Big news. Colorado is gonna allow therapists to do all these different psychedelics in really safe settings with really qualified people, for people who have PTSD, people who have trauma, people who have anxiety, people who've been to wars, people whose lives have been wars. And, uh, it's having a profound impact. And if people are out there and they're suffering, you know, I, I really, really encourage them to go to therapy and to, you know, maybe even research this stuff, uh, because again, you give these disclaimers all the time on this podcast, but there is help out there.

    15. TF

      Yeah.

    16. JC

      And you don't need to suffer alone. And sometimes people will mask their suffering and mask their problems with performance, and this is the show about performance.

    17. TF

      Yeah. Absolutely.

    18. JC

      And that's why people listen to it and people are drawn to it. But sometimes we're drawn to performance because we don't wanna face the pain or suffering that is driving that performance, the fuel, you know?

    19. TF

      Yeah.

    20. JC

      Like, a lot of times those hot coals that are burning, that's a lot of pain and suffering.

    21. TF

      Yep.

    22. JC

      And, uh, it fuels an engine, a mighty engine.

    23. TF

      Yeah.

    24. JC

      But, you know, then you get to the destination like we're talking about here, and then, "Hey, maybe this isn't serving me well anymore," right? And you want it to serve you well, you know?

    25. TF

      Yeah. Agreed. And I'll make just a couple recommendations for folks. One, this is, this is an extremely heavy podcast in terms of content, but if people are curious in the capacity of researching psychedelic therapies or psychedelic-assisted therapies, but also looking at alternatives to that, uh, I did do a podcast that people can find at tim.blog/trauma, which is a conversation between myself and Debbie Millman-

    26. JC

      It's incredible

    27. TF

      ... who suffered from, uh, horrible childhood abuse. And we took very different paths, but found solace, found support in very, very different ways. And there are re- a lot of resources associated with the blog post in the show notes that people can, can look at. The other, if people are interested in identifying at least some of the credible institutions and scientists doing research on, say, complex PTSD and MDMA-assisted psychotherapy, which is now I believe through phase three, and psilocybin for treatment-resistant depression, et cetera. Uh, if you go to saiseifoundation.org, that's, that's the foundation I started some time ago, which is S-A-I-S-E-I, which means rebirth in Japanese. Saiseifoundation.org. There's a projects page where you can see the various universities and a lot of the researchers.

    28. JC

      Ah, I've been looking for this to see where all the research is actually occurring. You actually made a page. I was telling somebody recently, like, there should just be a place people could go to see where the progress has been because people are not aware of how much pro- people, I think it's next year that MDMA will be available in therapy in some psychiatric settings, right? Uh, if I'm understanding the-

    29. TF

      Yeah, I'd have to check the latest and greatest.

    30. JC

      Mm.

  25. 1:58:25 – 2:06:13

    Jason’s billboard and parting thoughts.

    1. TF

      J Cal.

    2. JC

      Yeah.

    3. TF

      We're, uh, we're coming up on-

    4. JC

      So I didn't, I was like, oh wow, just a quick 75 minutes, 90 minutes-

    5. TF

      Yeah, yeah

    6. JC

      ... and look, we've done two hours.

    7. TF

      So it's two hours.

    8. JC

      [laughs] Here we are, two hours.

    9. TF

      Two hours, two hours plus. Is there anything that you would put just as, uh, winding this to a close-

    10. JC

      Yeah

    11. TF

      ... anything that you would put on a billboard, metaphorically speaking?

    12. JC

      Yeah.

    13. TF

      Like a m- message, a quote, a word, anything at all that if you were to get a message out to billions of people, assuming they would understand it, what might you put on the billboard? Anything at all.

    14. JC

      Anything on the billboard I wanted to, wow. There's part of me that wants to tell people, you know, to take chances and that they can do it.

    15. TF

      Yeah.

    16. JC

      Like, to give it a shot. Like, to just give it a shot.

    17. TF

      Mm-hmm.

    18. JC

      Right? Like, it, it might just work out, like, what if it works out?

    19. TF

      Mm.

    20. JC

      Give it a shot. What if it actually works out? That's my head speaking, and then my heart is just be kind to each other.

    21. TF

      Yeah.

    22. JC

      Especially in the face of when people are unkind.

    23. TF

      Mm-hmm.

    24. JC

      I just notice that, like, people, and this is coming from me, like a [laughs]

    25. TF

      [laughs]

    26. JC

      I'm a brawler. I mean, I'm known for arguing [laughs] and a brawler.

    27. TF

      [laughs]

    28. JC

      But I, I don't know what's in the air. I don't know if it's since Trump and, like, this whole polarization in the country, but I would really like to see people be kinder to each other and just have, like, really open-hearted discussions with each other. And I, you know, I think your podcast, to a lesser extent what I'm trying to do on All In, I, I think there are roadmaps here for people to have productive discussions with each other that move themselves, evolve themselves, and evolve humanity. I think that's why podcasting is such a special medium, and I think, you know, you really can have productive discussions with people you disagree with. You can have great relationships. You don't have to agree on everything. You could have great friendships. So have those productive discussions with a, with a big open heart and, uh, you know, develop those friendships. It really is the best part of life. So for me-

    29. TF

      Yeah

    30. JC

      ... I, I don't know, it's like I, the two best things I've done in my life is have great friends and build cool shit.

Episode duration: 2:06:34

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