#635: Jason Calacanis on Brooklyn Grit, Big Asks, Angel Investing (Uber, Calm, Robinhood, and more), The Magic of Thinking Big, and St*bbing People in the Face but Never in the Back

Brought to you by Eight Sleep’s Pod Cover http://eightsleep.com/Tim sleeping solution for dynamic cooling and heating, House of Macadamias https://www.houseofmacadamias.com/tim delicious and nutritious nuts, and LinkedIn Jobs http://linkedin.com/tim recruitment platform with 800M+ users. Jason Calacanis (@jason https://twitter.com/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 https://www.amazon.com/Angel-Invest-Technology-Startups-Timeless-Investor/dp/0062560700/?tag=offsitoftimfe-20. He also hosts two podcasts, This Week in Startups http://thisweekinstartups.com/ and All-In https://www.allinpodcast.co/. Please enjoy! This episode is brought to you by LinkedIn Jobs https://linkedin.com/Tim. Whether you are looking to hire now for a critical role or thinking about needs that you may have in the future, LinkedIn Jobs https://linkedin.com/Tim can help. LinkedIn screens candidates for the hard and soft skills you’re looking for and puts your job in front of candidates looking for job opportunities that match what you have to offer. Using LinkedIn’s active community of more than 800 million professionals worldwide, LinkedIn Jobs https://linkedin.com/Tim can help you find and hire the right person faster. When your business is ready to make that next hire, find the right person with LinkedIn Jobs. And now, you can post a job for free. Just visit LinkedIn.com/Tim https://linkedin.com/Tim. * This episode is also brought to you by House of Macadamias https://www.houseofmacadamias.com/tim delicious and nutritious nuts! I love macadamia nuts and have been enjoying them often since keto expert Dr. Dominic D’Agostino recommended them on the podcast in 2015. They taste great, and with more healthy, monounsaturated fat than both olive oil and avocados, 27% fewer carbs than almonds, and more than 50% fewer carbs than cashews, they’re the perfect low-carb, keto-friendly, nutty snack. In fact, I just ate a handful of lightly white-chocolate-covered macadamias about an hour ago to keep me going through the afternoon until dinner. And I will say this: ​House of Macadamias https://www.houseofmacadamias.com/tim produces the best-tasting macadamia nuts I’ve ever eaten… by far. Listeners of The Tim Ferriss Show can use code TIM20 to get 20% off all orders, plus free two-day shipping across the US, UK, and African continent with the purchase of two or more boxes! Visit HouseOfMacadamias.com/Tim https://www.houseofmacadamias.com/tim to discover some of the most delicious and nutritious nuts on the planet. * This episode is also brought to you by Eight Sleep http://eightsleep.com/Tim! Eight Sleep’s Pod Cover http://eightsleep.com/Tim is the easiest and fastest way to sleep at the perfect temperature. It pairs dynamic cooling and heating with biometric tracking to offer the most advanced (and user-friendly) solution on the market. Simply add the Pod Cover http://eightsleep.com/Tim to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. It also splits your bed in half, so your partner can choose a totally different temperature. For a limited time, Eight Sleep is offering my listeners up to $450 off their Sleep Fit Holiday Bundle, which includes my personal favorite, the Pod 3 Cover. Go to EightSleep.com/Tim http://eightsleep.com/tim to get the exclusive holiday savings. Eight Sleep currently ships within the USA, Canada, the UK, select countries in the EU, and Australia. That’s EightSleep.com/Tim http://EightSleep.com/Tim * [05:39] Why is this only the first time Jason’s been on the show? [06:37] Never underestimate the power of checklists. [08:56] How Jason’s young life was steeped in blood and taxes. [11:57] How Jason entered the world of entrepreneurship. [29:32] What happened when Jason got fired from his own company. [34:05] Orchestrating a comeback the very next day. [37:49] The Mercury Club that never was. [41:37] The origin of “Calacanis.” [43:01] Building a blogging empire. [48:36] Finding blog writers. [52:51] Planning events and making memories. [58:39] Friendship, loyalty, and collaboration with close friends. [1:06:00] All-In: When a solo act gets tricked into joining a band. [1:13:39] Memorable times All-In has gone off the rails. [1:21:49] With greatly followed podcasts comes great responsibility. [1:27:38] KeepingAll-In running smoothly with four very different personalities. [1:34:53] Talent-wrangling techniques. [1:39:30] Bill Maher’s moderation style. [1:40:47] Friendly rapport can be contagious. [1:42:26] Can you see your comfort zone from the Overton window? [1:45:44] Transfering skills, building popularity, and co-existing with jet blockers. [1:52:16] What happens when you catch the car? [1:55:15] Psychedelic therapy and a big win in Colorado. [2:01:28] Jason’s billboard and parting thoughts. * For show notes and past guests on The Tim Ferriss Show http://tim.blog/podcast, please visit tim.blog/podcast https://tim.blog/podcast/?utm_source=podcast&utm_medium=podcast&utm_campaign=podcast-description. For deals from sponsors of The Tim Ferriss Show http://tim.blog/podcast, please visit tim.blog/podcast-sponsors http://tim.blog/podcast-sponsors Sign up for Tim’s email newsletter (5-Bullet Friday) at tim.blog/friday https://go.tim.blog/5-bullet-friday-1/. For transcripts of episodes, go to tim.blog/transcripts http://tim.blog/transcripts. Discover Tim’s books: tim.blog/books http://tim.blog/books. Follow Tim: Twitter: twitter.com/tferriss https://twitter.com/tferriss Instagram: instagram.com/timferriss https://instagram.com/timferriss/ YouTube: youtube.com/timferriss https://www.youtube.com/timferriss Facebook: facebook.com/timferriss https://www.facebook.com/TimFerriss/ LinkedIn: linkedin.com/in/timferriss http://linkedin.com/in/timferriss Past guests on The Tim Ferriss Show http://tim.blog/podcast include Jerry Seinfeld https://tim.blog/2020/12/08/jerry-seinfeld/, Hugh Jackman https://tim.blog/2020/06/26/hugh-jackman/, Dr. Jane Goodall https://tim.blog/2020/04/16/jane-goodall/, LeBron James https://tim.blog/2018/11/27/lebron-james-mike-mancias/, Kevin Hart https://tim.blog/2020/05/20/kevin-hart/, Doris Kearns Goodwin https://tim.blog/2018/09/07/doris-kearns-goodwin-leadership/, Jamie Foxx https://tim.blog/2015/12/06/jamie-foxx/, Matthew McConaughey https://tim.blog/2020/10/19/matthew-mcconaughey/, Esther Perel https://tim.blog/2017/05/21/esther-perel/, Elizabeth Gilbert https://tim.blog/2020/05/08/elizabeth-gilbert/, Terry Crews https://tim.blog/2017/12/20/terry-crews-how-to-have-do-and-be-all-you-want/, Sia https://tim.blog/2020/08/12/sia/, Yuval Noah Harari https://tim.blog/2020/10/27/yuval-noah-harari/, Malcolm Gladwell https://tim.blog/2016/06/21/malcolm-gladwell/, Madeleine Albright https://tim.blog/2020/05/27/secretary-madeleine-albright/, Cheryl Strayed https://tim.blog/2017/03/30/cheryl-strayed/, Jim Collins https://tim.blog/2019/02/18/jim-collins/, Mary Karr, https://tim.blog/2020/11/11/mary-karr/ Maria Popova https://tim.blog/2014/10/21/brain-pickings/, Sam Harris https://tim.blog/2020/05/15/sam-harris-2/, Michael Phelps https://tim.blog/2021/01/21/michael-phelps-grant-hackett/, Bob Iger https://tim.blog/2020/01/16/bob-iger/, Edward Norton https://tim.blog/2019/10/31/edward-norton-motherless-brooklyn/, Arnold Schwarzenegger https://tim.blog/2015/02/02/arnold-schwarzenegger/, Neil Strauss https://tim.blog/2014/06/24/neil-strauss/, Ken Burns https://tim.blog/2019/09/12/ken-burns/, Maria Sharapova https://tim.blog/2017/08/26/maria-sharapova/, Marc Andreessen https://tim.blog/2016/05/29/marc-andreessen/, Neil Gaiman https://tim.blog/2019/03/28/neil-gaiman/, Neil de Grasse Tyson https://tim.blog/2019/10/03/neil-degrasse-tyson/, Jocko Willink https://tim.blog/2016/09/21/jocko-willink-on-discipline-leadership-and-overcoming-doubt/, Daniel Ek https://tim.blog/2020/12/03/daniel-ek/, Kelly Slater https://tim.blog/2020/09/08/kelly-slater/, Dr. Peter Attia https://tim.blog/2019/11/27/peter-attia-fasting-metformin-longevity/, Seth Godin https://tim.blog/2016/02/10/seth-godin/, Howard Marks https://tim.blog/2018/09/25/howard-marks/, Dr. Brené Brown https://tim.blog/2020/02/06/brene-brown-striving-self-acceptance-saving-marriages/, Eric Schmidt https://tim.blog/2019/04/09/eric-schmidt/, Michael Lewis https://tim.blog/2020/05/01/michael-lewis/, Joe Gebbia https://tim.blog/2018/03/08/joe-gebbia-co-founder-of-airbnb/, Michael Pollan https://tim.blog/2018/05/06/michael-pollan-how-to-change-your-mind/, Dr. Jordan Peterson https://tim.blog/2021/03/01/jordan-peterson/, Vince Vaughn https://tim.blog/2017/05/31/vince-vaughn/, Brian Koppelman https://tim.blog/2020/04/23/brian-koppelman/, Ramit Sethi https://tim.blog/2019/05/07/ramit-sethi/, Dax Shepard https://tim.blog/2020/11/18/dax-shepard/, Tony Robbins https://tim.blog/2014/10/15/money-master-the-game/, Jim Dethmer https://tim.blog/2020/05/18/jim-dethmer/, Dan Harris https://tim.blog/2020/11/19/dan-harris/, Ray Dalio https://tim.blog/2017/09/13/ray-dalio/, Naval Ravikant https://tim.blog/2015/08/18/the-evolutionary-angel-naval-ravikant/, Vitalik Buterin https://tim.blog/2021/03/08/vitalik-buterin-naval-ravikant/, Elizabeth Lesser https://tim.blog/2021/03/16/elizabeth-lesser/, Amanda Palmer https://tim.blog/2019/04/18/amanda-palmer-2/, Katie Haun https://tim.blog/2021/02/18/katie-haun/, Sir Richard Branson https://tim.blog/2017/10/09/richard-branson/, Chuck Palahniuk https://tim.blog/2020/09/02/chuck-palahniuk/, Arianna Huffington https://tim.blog/2017/10/18/arianna-huffington/, Reid Hoffman https://tim.blog/2015/08/31/the-oracle-of-silicon-valley-reid-hoffman-plus-michael-mccullough/, Bill Burr https://tim.blog/2017/09/17/bill-burr/, Whitney Cummings https://tim.blog/2015/06/26/whitney-cummings/, Rick Rubin https://tim.blog/2015/05/15/rick-rubin/, Dr. Vivek Murthy https://tim.blog/2020/03/26/vivek-murthy/, Darren Aronofsky https://tim.blog/2017/09/09/darren-aronofsky/, Margaret Atwood https://tim.blog/2022/02/22/margaret-atwood/, Mark Zuckerberg https://tim.blog/2022/03/24/mark-zuckerberg/, Peter Thiel https://tim.blog/2014/09/09/peter-thiel/, Dr. Gabor Maté https://tim.blog/2018/02/20/gabor-mate/, Anne Lamott https://tim.blog/2021/07/09/anne-lamott/, Sarah Silverman https://tim.blog/2022/01/12/sarah-silverman/, Dr. Andrew Huberman https://tim.blog/2021/07/06/andrew-huberman/, and many more. 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Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Tim Ferriss?

  This episode is brought to you by House of Macadamias delicious and nutritious nuts. Holy hell, folks, I tell you, these things are delicious. I've been gobbling them all day. Anyway, I love macadamia nuts and have been enjoying them often since keto expert Dr. Dominic Agostino recommended them way back on the podcast in 2015. They taste great and they have more healthy mono unsaturated fat than both olive oil and avocados, 27% fewer grams of carbs than almonds, and more than 50% fewer grams of carbs than cashews. They're the perfect low carb keto-friendly nutty snack. In fact, I just ate a handful of lightly white chocolate dusted, dare I say, macadamias about an hour ago to keep me going through the afternoon until dinner. It is the perfect snack for me. And I will

• 0:45Tim Ferriss?

  say this, House of Macadamias produces the best tasting macadamia nuts I've ever eaten, that I've ever had by far. That's due in part to their location in the Mpumalanga Province of South Africa, which provides the ideal temperature, altitude, soil composition, rainwater, and pristine mountain water for growing, you guessed it, macadamias. House of Macadamias have partnered with the largest macadamia producer in the world comprising 94 independent farmers in South Africa, which gets them first pick of the highest quality macadamia nuts in the region to make their one-of-a-kind snacks, like their vegan paleo and keto-friendly chocolate dipped macadamias. They really took their time to get all of this right, and they've done more than two years of flavor testing,

• 1:27Tim Ferriss?

  and you can taste that in each packet you consume. And I've had two of those today. Listeners of the Tim Ferriss Show can use code TIM20, that's T-I-M-2-0, to get 20% off of all orders, plus free two-day shipping across the US, UK, and African continent with the purchase of two or more boxes. Visit houseofmacadamias.com/tim to discover some of the most delicious and nutritious nuts on the planet. Again, one more time, that's houseofmacadamias.com/tim code TIM20.

• 2:02Tim Ferriss?

  This episode is brought to you by Eight Sleep. My God, am I in love with Eight Sleep. Good sleep is the ultimate game changer. More than 30% of Americans struggle with sleep, and I'm a member of that sad group. Temperature is one of the main causes of poor sleep, and heat has always been my nemesis. I've suffered for decades tossing and turning, throwing blankets off, putting them back on, and repeating ad nauseam. But now, I am falling asleep in record time, faster than ever. Why? Because I'm using a simple device called the Pod Pro Cover by Eight Sleep. It's the easiest and fastest way to sleep at the perfect temperature. It pairs dynamic cooling and heating with biometric tracking to offer the most advanced, but most user-friendly solution on the market.

• 2:47Tim Ferriss?

  I polled all of you guys on social media about the best tools for sleep, enhancing sleep, and Eight Sleep was by far and away the crowd favorite. I mean, people were just raving fans of this. So, I used it, and here we are. Add the Pod Pro Cover to your current mattress and start sleeping as cool as 55 degrees Fahrenheit or as hot as 110 degrees Fahrenheit. It also splits your bed in half, so your partner can choose a totally different temperature. My girlfriend runs hot all the time. She doesn't need cooling. She loves the heat, and we can have our own bespoke temperatures on either side, which is exactly what we're doing. Now, for me, and for many people, the result: Eight Sleep users fall asleep up to 32% faster,

• 3:30Tim Ferriss?

  reduce sleep interruptions by up to 40%, and get more restful sleep overall. I can personally attest to this because I track it in all sorts of ways. It's the total solution for enhanced recovery, so you can take on the next day feeling refreshed. And good news: Eight Sleep has launched the next generation of the Pod. The new Pod 3 enables more accurate sleep and health tracking with twice the number of sensors. It's just a smoother, better experience that delivers you the best sleep on earth. At least, that has been true for me. Simply add this to your existing mattress, and you're all set. It is not magic, but sometimes it does feel like it. It just works. For a limited time, Eight Sleep is

• 4:10Tim Ferriss?

  Offering my listeners, that's you guys, up to $450 off of their Sleepfit Holiday Bundle, which includes my personal favorite, the Pod 3 cover. Go to eightsleep.com/tim to get the exclusive holiday savings. That's all spelled out, E-I-G-H-T, eightsleep.com/tim. Eight Sleep currently ships within the USA, Canada, the UK, select countries in the EU and Australia. That's eightsleep.com/tim.

• 4:39Speaker 01

  At this altitude, I can non-flight out for a half mile before my hands start shaking.

• 4:43Speaker 02

  Can I ask you a personal question?

• 4:45Speaker 03

  No, it would seem like a big time.

• 4:49Speaker 02

  I'm a cybernetic organism, living tissue over metal endoskeleton.

• 5:01Tim Ferriss?

  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 going to 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 dot com, and on Twitter at Jason, because he was an early bird on the Twitter platform. Jason, nice to see you, man.

• 5:41Speaker 01

  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.

• 5:49Tim Ferriss?

  It's the first time.

• 5:50Speaker 01

  The first time we're actually recording it, which is great. I listened to, I would say, two out of three of your episodes. You've had a lot of investors on.

• 5:58Tim Ferriss?

  I have.

• 5:59Speaker 01

  So somebody's like, how come you haven't been on Tim Ferriss's podcast? I'm like, he's got so many investors on, what can I add, right? And I'm sure at some point.

• 6:06Tim Ferriss?

  There's a lot.

• 6:08Speaker 01

  Well, sure, I'm sure. But I mean, it is so great to see how well your podcast has done over the years. I remember the first time I met you in Tahoe with, I guess, Saka. And it was like, hey, this is the four-hour work week guy. And I was like, you know how hard you're making my life? All these founders, I mean, not only they go work four hours, they're starting breaking your chops.

• 6:31Tim Ferriss?

  It's part of the charm. Yeah, it's part of the charm.

• 6:34Speaker 01

  Good to see you.

• 6:35Tim Ferriss?

  It is good to see you. And so you, I consider a master of podcasting. We're going to 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 QuickTime. So we are both running backup QuickTime audio. So we have extra local copies in case something breaks, because things often break. What was the, what was the tactic that you shared? Because it's so smart.

• 7:06Speaker 01

  Well, 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? Like, oh, I didn't hit the record button. So instead of asking, can you, you know, record a QuickTime, I say, how many seconds is your QuickTime running? And they say, it's 36 seconds. Now I know it's running. But the bigger piece is, there's this book, The Checklist Manifesto, you and I obsessed with, probably sort of our kinship.

• 7:31Tim Ferriss?

  A tool go on day.

• 7:33Speaker 01

  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, you know, because people forget. And all those great stories in the book about like, surgeons and pilots were like, I don't need a checklist. And then everybody dies.

• 7:56Tim Ferriss?

  Yeah, yeah.

• 7:57Speaker 01

  And then a nurse comes along and is 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 a plane with four engines.

• 8:07Tim Ferriss?

  Yeah.

• 8:07Speaker 01

  Because people had more discipline and, you know.

• 8:09Tim Ferriss?

  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, look at that. Yeah.

• 8:17Speaker 01

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

• 8:32Tim Ferriss?

  It works both ways.

• 8:34Speaker 01

  They would put a little tent on top of the clean instrument. So like, a clean scalpel would have a tent on top. And the nurse was responsible for cleaning everything and putting the tents on. So then they knew it was clean. And you take the tent off. Now it's been used. So tent on means clean. Don't put the tent on a dirty scalpel.

• 8:54Tim Ferriss?

  Tent off, no bueno.

• 8:56Speaker 01

  No bueno.

• 8:57Tim Ferriss?

  Now, you can't believe everything you read on the internet. So please correct me if I'm getting any of this wrong. But, you know, your mom was tending to people in the ER. Your dad had a bar, as I understand it, there were times when you'd be cleaning blood off the floor from all the brawls and fights. And then raided at one point, I think by the, I don't know if it was the FBI, but with

• 9:18Speaker 01

  Uh, tax authorities.

• 9:19Tim Ferriss?

  Tax authorities.

• 9:20Speaker 01

  Yeah, my dad got a little behind on the taxes.

• 9:22Tim Ferriss?

  Yeah, the taxes. They sneak up on you.

• 9:25Speaker 01

  It turns out the tax authority, yeah, they're kind of humorless, like you 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 the seventies and eighties, in 1988, my dad's bar, after the stock market crashed, he went into basically debt and he was really gnarly. And then one summer afternoon in July, the, the feds, basically, and the tax authority came and padlocked the place, took everything out of it. And 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've shared your trauma on this podcast. It's like a gift to the world.

• 10:07Speaker 01

  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. Probably going to jail. I tried to make this business work. It didn't work. Take care of your mom. Like, whoa. It's kind of like that scene when, if you remember the Empire Strikes Back and like, Han Solo comes over to Chewbacca. It's like, just take care of the princess. I'll be back. You know, it was really intense, really intense.

• 10:33Tim Ferriss?

  Yeah. Yeah, but that's.

• 10:35Speaker 01

  It's crazy. And that, and that really is like, my life just got crazier and crazier after that, right? Like, so I forged such a crazy childhood that was so violent and crazy and just Brooklyn when it wasn't cool. That it kind of made when I went into business, I was kind of like, well, I don't have to worry about somebody jumping me.

• 10:55Speaker 01

  There's no violence here. Like, I'm not going to be murdered. I'm not going to jail. It's like, wow, this is easier. But I didn't know that world existed. You know, the only world I knew was the people who hung out at my dad's bar. The mafia, the Hells Angels, a bunch of cops, some percentage of which were in on the take with the other two groups. And then a bunch of Wall Street people. And so it was like out of a film like Goodfellas, Tim, I kid you not, like I would, I would have to go serve espresso to the bookie.

• 11:26Tim Ferriss?

  Yeah.

• 11:26Speaker 01

  Or the, the dealer or the head of the Hells Angels. It was bonkers. It, it went, you know, it just made me really good at dealing with people, I think.

• 11:36Tim Ferriss?

  Yeah, I would imagine you developed a lot of situational awareness.

• 11:41Speaker 01

  Adaptations, right? Yeah. You get a lot of adaptations real quick when you're dealing with those different types of individuals. But I look back on it now and I'm like, did that really happen? And then I look back at this, what's happening in my life now. And I'm like, is this really happening? So it's, it's been a pretty surreal life, the whole way, I have to say.

• 11:57Tim Ferriss?

  So if we flash forward a little bit, 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 to coffee shops and other spots. 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 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?

• 12:30Speaker 01

  So having a dad who's an entrepreneur, it kind of puts it in you. 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 because remember my dad had no money. So I had to pay for all this on my own. It 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 because, you know, sort of pre the web and mobile phones and we'd 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 newspapers.

• 13:14Speaker 01

  And I just looked at the people who were in the pictures, Tim, and I was like, why aren't 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's all I was exposed to. I didn't understand there was other stuff in the world. But 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 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, because Brooklyn was so different than Manhattan at the time.

• 13:53Tim Ferriss?

  Yeah, for sure.

• 13:54Speaker 01

  Brooklyn was a bunch of blue collar people. Manhattan were rich people and powerful people. And so something just clicked in my brain, and I said, I want to be powerful. I want to be rich. I want to be on the cover of a magazine. And I started looking at the magazines, and then I discovered The Masthead. And I saw The Masthead, and I said, wait a second. Who's the publisher and the editor in chief? Who has more power? Who is this editor at large? That sounds more important. But wait, it's in a smaller font and lower. 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 Barney's. Somebody had invited me to a party in the basement of Barney's. And I'm talking to this guy, and I said, what are you doing? And he says, oh, I work at a magazine.

• 14:33Tim Ferriss?

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

• 14:38Speaker 01

  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 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, because 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. 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.

• 15:22Speaker 01

  Booking a ticket to a movie, a dial-up service. So, and, oh, a CD-ROM. Has a video on it, or it has 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 going to build a website. And so I was on the website team. And the website was a picture of 10 Sony logos. Sony Music, Columbia Records. We literally sat 10 people in a room, designing a webpage with 10 logos on it. That was the entirety of the website. It was one page. And then like a 12-page legal disclaimer. So this is a very interesting like moment in time. And I said, what magazine? And he said, paper magazine. I said, you work at paper magazine? And he said, I created

• 16:07Speaker 01

  paper magazine. I said, what do you mean, you created it? Like you're working at the printer? He said, no, no, I'm the editor in chief. I'm David Hershkovitz. I said, tell me everything. So I start talking to him. He says, why don't you come by my office? Because I'm setting up my dial-up. And I said, okay. And I go down to his office, which was sort of where Balfour is now, on Broadway, at Lower Broadway. And, you know, I help him with his internet. And we're talking about dial-up services. You should write a column for us about the internet, and this technology stuff. So I started writing for paper magazine. And I was like this little nerdy kid. And I didn't know how to write. I didn't know how to spell. I didn't know how to put a comma in a sentence. And so this Christine Mulhucki was my editor. She was like 20 something years old. I was 20 something years old. Started writing for paper magazine. And then Hershkovitz is like,

• 16:52Speaker 01

  he was really getting into the internet. And I remain friends with him to this day, 30 years later. And he would just ask me to come by the office, I hang out. And I'm hanging out at paper magazine. And he's like, hey, you want to go to a concert tonight? Yeah, sure. He says, yeah, we're gonna go to the Roxy. This new band, Chemical Brothers, is gonna be playing. And Orb's gonna be opening for them. And then we're in like the green room, or the VIP room, waiting for us to go on. And he's like, oh, Jason, I met this woman from Iceland. And I'm like, oh, you're from Iceland? Where is that? Is it like Norway or Sweden? And she's like, no, it's like over here. And she's talking really low. And I'm like, so what do you do? She's like, well, I have a record coming out. And I'm like, oh, that's awesome. What kind of music is this? Like, these guys? No, just some singers. Oh, I'm Jason. And she goes, I'm Bjork. Yeah, this is New York

• 17:34Speaker 01

  in the 90s. I mean, it was cool as F. Like, it was the zeitgeist was crazy. So all of this starts to spiral. And I just said, I need to make a magazine. And David had showed me the early issues of paper. And paper magazine was originally-

• 17:48Tim Ferriss?

  I've never heard you censor your cursing before. That was very delicate of you.

• 17:51Speaker 01

  It's a family show, I think.

• 17:52Tim Ferriss?

  You can curse. It's okay.

• 17:56Speaker 01

  You don't tell a kid from Brooklyn to start cursing. Your poor Atticars are gonna be, he just created three hours of anywhere.

• 18:02Tim Ferriss?

  Search replace, we have forty seven fucks in the first thirty minutes.

• 18:07Speaker 01

  Forty seven fucks given. So anyway, it's actually kind of fun to remember all this stuff. So he takes me to the archive room of Paper Magazine, which was a glossy at the time. And he says, look, it was a foldable thing. I got a foldable piece of paper and I folded it. And we would just put it for free, you know, in cafes. And I was like, you know, when like the Terminator, you see from his view and like all the words are going by and it's just like processing everything really fast. That was happening in my brain. I was like, okay, wait, free, fold it, print it, what? Okay, do this. I'm taking all of these instructions and I literally went to Tower Records, which is a place where they used to sell CDs and records. And they had a zine section and zines were short for magazines, Z I N E, for people who are under the age of forty.

• 18:49Speaker 01

  And this was like the most punk rock thing you could do after being in a punk rock band was to start a zine. And a zine just meant you got your friends together and wrote an article together and then you would photocopy it. So twenty six hundred famously was a zine about hacking in New York and I had met the founder of that. So there's like a little zine culture going on and I was like, huh. All my friends are starting internet stuff. I'm writing about the internet once a month. I write four hundred words. I could write forty thousand words. I could write four thousand words, whatever. And people had never been to San Francisco or Silicon Valley, but people were starting, somebody referred to what we were doing as Silicon Alley. I was like Silicon Alley. That's rad. And then I had seen somebody, I was like, well, I should be a reporter about Silicon Alley.

• 19:33Speaker 01

  I could do like a Silicon Alley reporter and it'd just be me reporting on what's happening here. Cause this is cool. Like there's like, now it's like two hundred people doing stuff. And so I just started a photocopy called Silicon Alley Reporter. And I went up to the Village Printing Shop on Forty Third Street and Sixth Avenue. And every time I'm in New York, I like to walk when I'm in New York, just to remind myself of that, those moments in time. And I always walk down that block to see if it's there. Village Printer, Village Printer, I don't know if it's still there, but a couple of years ago, it's still there. And it was twenty four hours and I brought it to the guy. There's a thing called tabloid paper. There's eight and a half by eleven plus eight and a half by eleven equals whatever it is. You know, like the seventeen by whatever. You could take that paper, fold it and put a staple in the middle and it would look like a newsletter.

• 20:18Speaker 01

  And so I said, okay, that's the format. I got page maker. I started laying it out. I took pictures. I wrote a couple of articles and I went there and I printed it. And he said, yeah, it's gonna be like 10 cents, a photocopy. And I was like, all right, 80 cents an issue. I could do this. So I go, I said, make me a thousand copies, 800 bucks, right? And I'm just gonna start handing them out like David Herschmitz did. And I go and he hands me a bill for 1750. And I said, wait, you said 10 cents, it's eight pages. He said, it's double sided. I said, it's double sided. I said, I don't have the money. He goes, what do you mean you don't have money? I got a thousand copies of Silicon Valley Reporter. So I start talking to the guy. Now I'm haggling with him and he's just the overnight manager. And I said, listen, I don't have the money for this. Like I just, my credit card's maxed out. Can you do me a favor? Like maybe someday I could

• 21:03Speaker 01

  do you a favor. I could put an ad in there. And he's like, don't tell anybody, okay? And I was like, no, I won't tell anybody. He's like, you know, they got a counter on these things. I could get busted. And I was like, I don't want you to get busted. And he's like, I don't know, man. This team's really cool. Just give me 800 bucks. And I just gave him 800 bucks. And then I realized, like, I started to learn a very interesting lesson in my life, that when I ask people things, that many times people will do what I ask them to do, like a Jedi kind of trick. But this guy did it out of the kindness of his soul. But I kind of started to learn early in my career, like, you could ask for things in the world, even sometimes outrageous things. And sometimes it happens, right? And I took them over

• 21:48Speaker 01

  to Roseland, where there was an internet party going on, or like, Roseland's a venue, like a music venue. And then some electronic music person had played and then like a bunch of internet multimedia people were gonna be hanging out. So I walk over there. I dropped off most of the issues at my little office I had, like a little office share. And then I took like 200 of them in my backpack and in my hands to the party. I get to the party at like 1:00 in the morning. And I just start handing them to people. And I had like this moment of clarity in my life. People started coming up to me to get them. And then I turn around and I look at the party, which was popping off. And every single person has the magazine open, the zine open, the photocopy, and is reading it with two or three people around them. The entire party stopped.

• 22:30Tim Ferriss?

  So what did that feel like? Like, what happened to you in that, when you saw that?

• 22:35Speaker 01

  Ah, okay. I got the power.

• 22:37Tim Ferriss?

  You got the power?

• 22:38Speaker 01

  And so remember I said I had no power as a child? And they take your dad's bar? Like, we're going deep into the trauma work here.

• 22:46Speaker 01

  Like literally, I mean, listen, I, you know, I consider it a privilege to be on here and you've shared a lot, like if this helps other people, but you know, when you don't have power and you're a kid and you live a scared life, uh, which I did. And then all of a sudden, the entire party in Manhattan is in the palm of your hand. And something you created has stopped everybody dead in their tracks. The adrenaline and the confidence, it felt like, you know, all of a sudden Superman like figures out, like when he reaches into the fire to, to get something he dropped. And it's like, oh, the fire doesn't burn me. Whoa, I could fly. Just this incredible wing sprouted. And I was like, wait a second, I could be an entrepreneur. I could do something in the world. And the next

• 23:31Speaker 01

  day I was at it. My phone was ringing. People are calling me. And then I just made a set of postcards that said, subscribe to the Silicon Valley Reporter, 10 issues a year, $100. Oh, no, $90. And I'd seen Esther Dyson charged a thousand dollars for her newsletter. So I was like, well, she's Esther Dyson. So if I charged 10%, maybe that's the same thing. Cause Esther Dyson was this famous, you know, angel investor. And I just, when I went out, if I didn't have the magazine on me, I had the cards and I would just hand the cards. And then within two or three months, I would get to my office share and there would be a stack of envelopes. And it would be 20 people sent me $90. It's $1800. And every day, $4,000, $6,000. And all of a sudden, there was like

• 24:16Speaker 01

  $30, $40,000 people subscribing. And it was kind of like the Kevin Kelly, like you only need 2,000 true fans. And then all of a sudden I was like, wait a second, I can quit my jobs. I can do this. I'm David Herschovitz and Kim from Paper. I did it. And it was like, whoa. And this all happened within 60 days. From a nobody trying to get into a party to meet somebody to all of a sudden, every CEO and person trying to meet me. And it was basically like this, all of a sudden becomes the sliding door kind of moment of your life. Like some random occurrence happened. I meet David Herschovitz at a party. I get this guy to print out the things. I go to that party and drop him off and all of a sudden I'm important.

• 24:59Speaker 01

  But remember, I wasn't covering tennis. I wasn't covering wine. I was covering this new thing called the internet when the browser didn't support graphics. So the timing was so insane because the internet, you talk about this Forrest Gump thing. See, that's a problem. This is gonna, now I, this is gonna stick. Everyone's gonna be like, well, I guess life's like a box of chocolates, Tim. He just dumped me the Forrest Gump. The internet industry, it's gonna stick forever. I'll take it. I'll take it. Forrest Gump had a great life.

• 25:32Tim Ferriss?

  Yeah, yeah, he did.

• 25:33Speaker 01

  And that was the start of a, that was the start of a very great, of a great life for a very simple man.

• 25:40Tim Ferriss?

  So I'm so glad we're talking about the early days because of course I had no idea of a lot of this.

• 25:46Speaker 01

  But you had the same thing. Nobody knew who you were. You're some guy and you, all of a sudden this four hour work week goes from, like, you got paid nothing for that book.

• 25:53Tim Ferriss?

  Nothing.

• 25:54Speaker 01

  And then all of a sudden, wasn't it the same exact experience?

• 25:56Tim Ferriss?

  It was similar. It was similar. Yeah. It was very similar. I remember when the book came out and I got a call from my editor, Heather Jackson at the time, and she said, why, hello, Mr. New York Times bestselling author. And I had just finished a day of radio satellite tours, which people did back in the day. They may still do them. And I had two pots of coffee and I was just exhausted. And I sat down on the floor and I was, and I said, Heather, don't fuck with me. I'm too tired. And she said, I'm serious. No, you made it. You're 15 on the extended list. So not in print, but you're on the list technically. And I thought, and I thought to myself, oh, wow. Things are about to change. Things are

• 26:39Tim Ferriss?

  about to change. And all of a sudden, you know, let's call it within the next few weeks, it kept growing and then it stayed on the list for, stayed on the print list for, I want to say four years plus, Unbroken. And in the beginning, started getting these calls, asking me to speak, offering to pay me for keynotes. I mean, none of this had happened before. And it was

• 27:00Speaker 01

  Mind blowing.

• 27:01Tim Ferriss?

  Bewildering. Yeah, very bewildering.

• 27:02Speaker 01

  The speaking gig is an interesting moment because you work your whole life. You make 30 grand, 40 grand a year. And then this kind of stuff happens to you. And then somebody calls, oh, Tim, would you like to come speak at this corporate thing? And you're like, why would I speak there? Oh, well, you know, your book. And you're like, okay. And they're like, well, of course, we'd like to give you an honorarium. And you're like, okay. And they're like, and it's $30,000 or $40,000. And you're like,

• 27:27Tim Ferriss?

  Say what?

• 27:28Speaker 01

  That's what I mean next year.

• 27:30Tim Ferriss?

  Come again.

• 27:31Speaker 01

  Thirty, three thousand dollars? And no, it is zero, thirty thousand. And you're just like, that makes no sense. And like, well, it's gonna be two hours of your time. We don't want to put you out, Mr. Ferris. And you're like, can I come back? Can I do it tomorrow, too?

• 27:45Speaker 01

  It is a mind blowing experience. I always, like, I literally just had one of these come in today, some corporate gig. And, you know, because All In has gotten so popular, all of a sudden now people want me to speak at a bunch of stuff again. And it's just like, the numbers are mind boggling. And you're just like, isn't it very weird? How like, you can go from being an absolute nobody to somebody wanting to give you tens of thousands of dollars to speak for an hour? That really screwed with my mind a lot. Also, because I had a lot of feelings of guilt and stuff about my parents. And I was like, you're offering me a speaking gig, which is what my mom or dad made in a year.

• 28:13Tim Ferriss?

  In a year, yeah. It's weird.

• 28:15Speaker 01

  You also had this kind of like-

• 28:17Tim Ferriss?

  Same situation. Yeah, so weird.

• 28:19Speaker 01

  It really does screw with your head. And it's very hard to stay grounded or figure out what's actually happening, right?

• 28:24Tim Ferriss?

  Yeah.

• 28:27Tim Ferriss?

  Just a quick thanks to one of our sponsors and we'll be right back to the show. This episode is brought to you by LinkedIn Jobs. These days, every new potential hire can feel like a high stakes gamble for your small business. So you want to be 100% certain that you have access to the most qualified candidates. That's why you should check out LinkedIn Jobs. LinkedIn Jobs helps you find the right people for your team faster and for free. Add your job and the purple hashtag hiring frame to your LinkedIn profile to spread the word that you're hiring. Simple tools like screening questions make it easy to focus on candidates with just the right skills and experience, so you can quickly prioritize who you'd like to interview and hire. It's why small businesses rate LinkedIn Jobs number one in delivering quality hires versus leading competitors.

• 29:09Tim Ferriss?

  It's been a tough year for everyone, so finish it strong by hiring the right new team members to set yourself up for strong and successful 2023. LinkedIn Jobs helps you find the qualified candidates you want to talk to faster. So post your job for free at LinkedIn.com/Tim. That's LinkedIn.com/Tim to post your job for free. Terms and conditions apply.

• 29:33Tim Ferriss?

  So let's talk about another holy shit moment. And this is January of 99. You're offered

• 29:40Speaker 01

  You got all the moments.

• 29:41Tim Ferriss?

  20 million, I believe.

• 29:43Speaker 01

  True story.

• 29:44Tim Ferriss?

  And

• 29:44Speaker 01

  Alan Meckler.

• 29:45Tim Ferriss?

  The commerce business. So, and I'm reading here, this is from Fast Company and it talks about your interaction with

• 29:53Speaker 01

  Alan Meckler.

• 29:54Tim Ferriss?

  This was with, I think, Douglas Rushkoff.

• 29:57Speaker 01

  Oh, Doug Rushkoff, yeah, my friend.

• 29:59Tim Ferriss?

  Yeah, yeah, yeah.

• 30:00Speaker 01

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

• 30:03Tim Ferriss?

  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.

• 30:16Speaker 01

  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 dot com boom. We're talking about 1999 now, right? 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 I got 11 million dollar company. I built up my credit cards and I was making just, you know, a couple of years earlier, minimum wage to work in the computer room at Ford, which was 350 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 of 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 and it became worth a billion dollars and he offered me 20 million bucks

• 31:01Speaker 01

  for Silicon Valley Reporter. But it was my identity and it was making 10 million. And I was like, I don't want to give up my identity. But I thought about it and I said, well, if I can make, if I can clear a million or $2 million a year off the magazine and profits, it'd be the same amount of money. So maybe I wouldn't do it. And then the dot com 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. It's like maybe four or five, maybe five or $600,000 in like this employment agreement. And they paid off all the bills because 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, literally not only

• 31:44Tim Ferriss?

  Tough business.

• 31:45Speaker 01

  Not only did I not have any money, all the money that was owed to me never showed up. Because all the companies had gone out of business. I was like, you owe me for three ads. They're like, 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? It's like manager, middle manager guy. And I'm like, sure, walk. Okay, sure. We'll go for a walk. We're like, hey, listen, you know, you're so talented. We don't think you being here and you're so talented. And I'm like, yeah. They're like, 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 said, you just bought my company. And the 20, you know, I had like 20 people left and they had reassigned them to this other venture capital thing they were doing. I said, you don't want me chasing Hal Canis, the Silicon Valley reporter, to work here.

• 32:31Speaker 01

  They said, no. I said, I just signed a contract with you for 600, you know, $500,000 or $600,000. They said, yeah. And he pulls out an envelope and he hands me a check for $500,000. He says, we're paying out your contract.

• 32:45Speaker 01

  Tim, you're the first person I've told these stories to, really. This is like, literally like the crazy life I've lived. And I am looking at a $500,000 check, which is an extraordinary amount of money, obviously. And the only thing I can think is, I want to beat the shit out of this guy. Just fucking fired me. They don't want me. I went from being a nobody to running New York, being on Charlie Rose, being on the cover of the New York Times, having a New Yorker thing being written about me, you know, just living like the peak New York experience. Living in a loft in Manhattan, sitting at, you know, in the first three or four rows of the Knicks games, hanging out with Allan Houston, you know, the number one star on the Knicks at the time. I mean, I was living it, the peak.

• 33:31Speaker 01

  And then overnight, boom, everything's gone. I got a 500K check in my hand and nothing. Nobody wants me. And I got so, the rage that I felt in that moment was like Hulk-like rage. Like I was a Berserker, like the Samurai armor, it just took the sword out. And I was like, I am going to prove I can do this again. I am going to show everybody that this was not a fluke. I've never felt more rage in my life, I don't think. And I've been in some pretty big brawls. And so then I just went and I took the money. And then I just went back to my, I got an office and the next day I said, I gotta build something. I gotta build something.

• 34:14Tim Ferriss?

  The next day?

• 34:16Speaker 01

  The next day, I was like, literally got an office share in my friend's office. I said, can I, you got a desk? 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.

• 34:32Tim Ferriss?

  So how do you even begin with such a blue sky? Blank page. How did you even start? Were you just pulling from random bits and pieces floating around? Did you have some approach?

• 34:46Speaker 01

  I started calling people out, what are you working on? What's, what's happening? And then this one person was making this photo sharing site, Flickr. Another person was doing a bookmarking site called Delicious. There's just this little underground of people who are building stuff for the web. Cause the web had gotten advanced now in the second decade and it could do like, the webpages could refresh themselves with Ajax. And there were kind of tables got, it 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 just like one group doing like journaling on the web. It's another group that was, you know, trying to do like photo sharing and follow your friends.

• 35:31Speaker 01

  And I'm just like, huh. And then I had somebody who had worked for me named Rafid Ali.

• 35:37Tim Ferriss?

  Now let me interrupt for one second. So the reason you're calling these people is not because you want to work with them on what they're doing necessarily? Or was it, or were you just trying to get a read of the landscape?

• 35:48Speaker 01

  I was literally just trying to network with people who I had known. And I was literally asking people like, what's going on? Is anybody doing anything cool? And I just started looking for people doing cool projects. Just to see what was gonna happen after the dot com bust. Cause everybody quit and everybody went and got jobs at

• 36:04Tim Ferriss?

  I got it.

• 36:05Speaker 01

  The companies.

• 36:05Tim Ferriss?

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

• 36:09Speaker 01

  Yes.

• 36:09Tim Ferriss?

  might be going next.

• 36:11Speaker 01

  Exactly. Is there anything interesting in the world?

• 36:13Tim Ferriss?

  My sports metaphors, but you get the idea.

• 36:15Speaker 01

  Yeah.

• 36:15Tim Ferriss?

  I'm talking about field hockey, everybody. Yeah.

• 36:16Speaker 01

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

• 36:24Tim Ferriss?

  Oh, yeah.

• 36:25Speaker 01

  It's hilarious, cause I taught him how to do a layup.

• 36:27Tim Ferriss?

  It is.

• 36:28Speaker 01

  I taught him how to dribble a basketball. It was hilarious. That's another story.

• 36:32Tim Ferriss?

  It is funny. And, and also if you learn a sport with J Cal, you are going to have to listen to so much shit.

• 36:39Speaker 01

  I'm gonna torture you.

• 36:40Tim Ferriss?

  He will torture you at every opportunity. Yeah.

• 36:44Speaker 01

  Watching Tim Ferriss go from like being a perfect fencer or perfect yoga, you know, in negative a hundred degree. And then he tries to dribble a basketball. It's literally like looking like a drunk person with a blindfold on.

• 36:57Tim Ferriss?

  Oh, yeah.

• 36:58Speaker 01

  But to your credit.

• 36:59Tim Ferriss?

  True story.

• 37:00Speaker 01

  I watched you learn how to do a layup. And I gave you, you asked me like three or four questions and you went from looking like you were blind and drunk to all of a sudden doing a layup in under like three minutes perfectly. And I was like, yeah, that's Tim Ferriss's gift. He knows how to ask the right questions and like, I'm watching you process. It's actually impressive. But anyway, it was, uh, it was like one of those moments where you're like, what's next in the world? I was just trying to figure what was next. And so I was just, cause also so many people were out of work. That if you couldn't get a job, you kinda just started tinkering, which is kinda how multimedia started. So it was like, I've seen this before. Technology keeps going. People are starting to tinker. And wifi had come out at that time. I was very fascinated about wifi.

• 37:42Speaker 01

  And I was thinking about wifi routers and putting wifi in places. And, you know, maybe you could have internet in 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. So the first idea I had was for Mercury Club. And I was gonna get a hundred New Yorkers and give them. Mercury Club, number 12345, 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, because I had gotten a Vespa. And I was driving around New York, and I realized, because 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, because you can just weave in and out of traffic. And I had seen Cosmo had started experimenting with Vespas. And I said, I'm gonna create a service where you pay $100

• 38:27Speaker 01

  a month for rich people, and you get four hours of deliveries, 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, because 800 numbers were another, like, platform, like, they became zines for a while, 1-800 Flowers, 1-800 Bachelors, 1-800 everything. And so I started looking into buying a 1-800 number, because I was just always very interested in mediums, right? Because if you get to a medium first, you can exploit it, whether it's podcasting like you and I did, or blogging like I did, and you did, I think, or scenes.

• 39:01Tim Ferriss?

  Starting 2005, blog.

• 39:02Speaker 01

  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 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 I never really actually thought about it, but it is true. And so, I also got the 800 number, so, yeah, 1-800 Mercury, I was trying to get a Mercury Club number. And my idea was, the reason, because I remember I talking to the guy who had done Cosmo, because I covered it in my magazine, and he said, yeah, I just, I should have just charged a delivery fee. Because the last six months, they started charging a delivery fee, and he said, yeah, the business worked in three of the nine cities. And I had only charged delivery fees.

• 39:47Speaker 01

  I was like, why didn't you? He's like, the VC told me not to, I just wanted to grow. I'm trying to get public. This is literally the same lesson people are learning now. So I was like, well, wait, instead of charging a delivery fee, why don't I just make it like, because I knew bike messengers. Bike messenger culture was like a big thing in New York. So bike messengers used to hang out aside where my loft was, because it was business commercial loft, the Starrett Lehigh Building in New York. It was a commercial, and we were living there illegally. Me, DJ Spooky, a couple of our artists were living in these illegal lofts. Anyway, the bike messengers were out 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 made 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 exercised.

• 40:30Speaker 01

  They were fit. They were smoking weed, listening to music. It was like the coolest gig ever. I was like, these guys, they figured out life.

• 40:36Tim Ferriss?

  Yeah, yeah.

• 40:37Speaker 01

  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 you make more money than the people you're dropping off the envelope to, but you're outside. It was like just a crazy revelation I had. So I was like, yeah, I'm gonna do Mercury Club and I built the whole business model for Mercury Club.

• 40:55Tim Ferriss?

  How did you land on the name?

• 40:56Speaker 01

  Well, Mercury, like the god with the wings on the feet. And I was just like, it came to, I was Greek. I always liked the Greek gods. So I was just like, yeah, I kinda started thinking about like fast. And I just thought, well, this would be incredible. Can you imagine you're like at like your Charlie Rose at a party or David Hershkowitz from Paper and you're just like, should we get cigarettes? Yeah. And you just pick out your, cause mobile phones had come out at that time. So imagine taking out your Star Tac and I had seen a Star Tac phone, those little flip phones. It's like, imagine you take that out and you dial an 800 number and you say, yeah, I need two packs of Marlboro Lights and you know, bring me the, a copy of Vanity Fair or Esquire magazine, cause I'm at a party, I want to show somebody. And then just somebody comes there and hands it to you. The ultimate luxury, like the ultimate power move. I can just call my assistant and just get anything I want. Anyway, I didn't wind up building that.

• 41:37Tim Ferriss?

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

• 41:41Speaker 01

  Kalikannis. Kalikannis means to have done well or good for you. So sometimes when I use my credit card and a Greek person does it, they're like, good for you. You've done well. Well, very nice. But it's with K's. So when my, when my grandfather went through Ellis Island, God rest his soul, they were like, Kalikannis, here's your banana, keep moving. And he was like, no, it's K's. And they were just like, fuck you, Kalikannis.

• 42:02Tim Ferriss?

  Here's your banana.

• 42:03Speaker 01

  They used to give you, no, they used to give bananas at Ellis Island, I understand.

• 42:07Tim Ferriss?

  That's real?

• 42:07Speaker 01

  Yeah. It was like some weird thing 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. So they're just like, here, have a banana.

• 42:17Tim Ferriss?

  Today, I learned, keep it moving.

• 42:18Speaker 01

  Well, and then the crazy thing, Tim, is I was on the Ellis Island website and on the Ellis Island website, I searched for my last name and they had archived everything. And Kalikannis, my great grandfather, or my grandfather, rather, went through like 12 times. And it turned out he was in the Merchant Marines. He was an engine captain and I knew that. But every time he came back to America with human passengers. He had to sign in again. And so he has gone through like 12 times. Wow. It was quite a weird. That's wild. 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. It was human cargo. It's pretty crazy, right? That is wild.

• 43:01Speaker 01

  So anyway, then I had watched the blog stuff happen. And two people who had worked for me, Shani Jardine was my event producer. 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? Because she's awesome and rad. And I hired Shani to come work with me at Silk and Airport. She would produce my events. And then when everything shut down, she started working on this like boing, boing thing. And I'm like, boing, boing? What are you doing with your life? She was like, yeah, we write blog posts. I'm like, logs? Blogs? Like Rafael Ali was doing? Because this kid who had worked for me, Rafael Ali, was doing

• 43:40Speaker 01

  a blog on the side called paidcontent.org. And somebody ratted him out when he was working at the magazine, that he was moonlighting. Now, back in the day, you couldn't have a side hustle. That was like instant firing. So I called 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 paid content? And I'm like, yeah. I'm like, 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 mean, I said, hold on, kid. Let me stop you. Number one, nobody's paying for content. The whole reason we started the internet is

• 44:21Speaker 01

  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'm like, No publication will ever work if there is not an editorial structure. It will fail because there'll be spelling errors. You're going to 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. And I just like admonished Rafat. Now I'm an investor in this company now, Skift.

• 45:03Speaker 01

  But that accepted in me because when we shut down, I had talked to Shenny. I talked to Rafid and Rafid was like, yeah, I'm making like four grand a month on ads. I'm like, I was paying you 35K. You're making 4K now? You're making 48,000, you're making $13,000 more than when you worked for me? And then Shenny's like, I'm getting a 5K draw a month. I'm like, what? I'm like, 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 and do like two or three hours. So it's like, you know, this is before the four hour work week revolution. I mean, this is during the 60 hour reality of being a worker. And I was like, blogs, huh? I started reading blogs and I was like, you know, there's something here. Blogs are dope.

• 45:44Speaker 01

  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, oh, Shenny's spicy. And I remember like, I wouldn't have let her write that. I would have stopped her. Then it, you know, 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.

• 46:26Speaker 01

  I didn't understand what they meant, but literally was that 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 didn't understand what they were talking about. But it, it kind of another inception moment. I was like, wait a second. What if you had a hundred of them? 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 next game and I said, what if we had weblogs? Blogs were originally called weblogs because 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.

• 47:09Speaker 01

  And then he got the domain name and then we started building them. And we did a weblog on wifi. 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. 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 Peter Rojas split the rest. In 18 months, after my $20 million offer had gone away, I got the $30 million offer.

• 47:44Tim Ferriss?

  That's just insane. It's just insane.

• 47:47Speaker 01

  The berserker insane J Cal, I'm going to 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. I was like, yep, I can do it. I can do it anytime I want. Anytime I want, I can build a brand, a business, and I can just get it from zero to whatever. Yeah, I might fail two out of three times, but I could do it. And that was when it was like, okay, once you're lucky, twice you're good. It was my once you're lucky, twice you're good moment. Cause then everybody who had watched me fail and kind of danced on my grave at Silicon Valley Reporter was like, oh God.

• 48:22Tim Ferriss?

  The cat came back. The very next day, we thought he wasn't gone, but he wouldn't stay away.

• 48:27Speaker 01

  There's a lot of people who are just like, oh, he's going to be insufferable after this.

• 48:33Speaker 01

  They weren't wrong.

• 48:36Tim Ferriss?

  So I just a couple of maybe boring housekeeping questions. I'm thinking, I'm thinking of the timing of building these weblogs.

• 48:44Speaker 01

  Yeah.

• 48:44Tim Ferriss?

  How did you find the writers to do this?

• 48:49Speaker 01

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

• 48:59Tim Ferriss?

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

• 49:11Speaker 01

  Yeah, jail, $32 billion eviscerated. I actually wanted to talk to you about like people who commit fraud and lie because I was interested in perspective on it.

• 49:18Tim Ferriss?

  Yeah.

• 49:18Speaker 01

  Because I just can't imagine it because the system is so easy to win 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 to just have a win by just working hard? Anyway, putting that aside.

• 49:30Tim Ferriss?

  But I interrupted you because you were you were tying the weblogs and

• 49:34Speaker 01

  Oh, the writers. Yeah. So it's very simple. Everybody was out of work. And so I just 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 and like we'd find somebody who had written a blog about Apple, Sean Bonner. And I said to Sean

• 49:52Tim Ferriss?

  Sean Bonner.

• 49:53Speaker 01

  Yeah. And I said, Hey, Sean, 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 could figure it out because I did a magazine. He's like, All right, that's pretty smart. I was like, I see you're writing some Apple blogs. Could we put them on our Apple blog? Or if I gave you the login, would you post them? Because Brian Alvey, who's a genius, he's now running WordPress for for Matt Mullenweg.

• 50:13Tim Ferriss?

  Oh, look at him.

• 50:14Speaker 01

  WordPress like Pro VIP that you like people like you and I use.

• 50:17Tim Ferriss?

  At Automattic, yeah.

• 50:18Speaker 01

  At Automattic. And so anyway, like a great collaborator of my career, you know, my he's kind of my George Harrison or my, you know, my Paul to my Lennon or vice versa. And he had built the software that was better than everybody's, better than Typeform, better than Blogger, better than everything. And I just gave Sean the login and I was like, Listen, I want to pay you something because I want to own the blog posts. He's like, You want to own a paragraph of me writing about a MacBook? It's three sentences, Jason. It's worthless. I'll do it for free. And I was like, I'll tell you what.

• 50:51Speaker 01

  How many a day could you do about Apple products? It's like two. I was like, okay, two, 60. I'll give you 150 bucks a month, cash, to just let us run these over here. It's a paragraph each. He's like, I can write these in 10 minutes. Like, you're an idiot, but sure, I'll take whatever it is, $2 or $3 a blog post. So we just then just started hiring people and then we made a $5 a blog post, eventually $10 a blog post. And people thought we were stupid because minimum wage at the time was $10. And people were like, I wrote three blog posts this hour and you gave me $30. But I had done a spreadsheet with Brian and I said, here's how many pages we're getting. Here's what I think we can make per page view. Here's what the cost is per blog post. All we have to do with this business is scale it and then somebody will buy it.

• 51:36Speaker 01

  And he said, yeah, I think you're right. I said, you do the tech, I'll get the writers and the advertising. I'll see you on the other side. And we both put our heads down for 18 months and we had 450 bloggers in the system, of which maybe 200 were active. And we were pounding out thousands of blog posts a week across 87 different topics. And then AOL found out about what we're doing and they had looked at Gawker and they had looked at us. And Engadget was crushing Gawker because we stole Peter Rojas from Gizmodo. It's a whole other story. Nick Denton and I had quite a rivalry for a while. It was a fun rivalry too, but you know, Peter Rojas was actually the missing piece with Brian, Alvy and I. And once we got Peter Rojas, he taught us like, hey idiots, like just come up with a name for the blogs. I don't want to be gadget.weblugsinc.

• 52:18Speaker 01

  So then we made the apple.weblugsinc, the unofficial Apple weblog, Tuaw, T-U-A-W, which people fell in love with. People were addicted to Tuaw because at that point we'd do an eight or nine blog posts a day about Apple. And Steve Jobs read it and Johnny Ive and everybody. And then Engadget became a juggernaut. And it was just like a very like, simple business. And at that time, $30 million was the equivalent of hundreds of millions now.

• 52:43Tim Ferriss?

  Yeah, for sure.

• 52:44Speaker 01

  It was a different era.

• 52:45Tim Ferriss?

  It's still, I mean, 30 million today would still be a good chunk of change. So let me flash forward. And I want to 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. I've only produced one event and it was

• 53:03Speaker 01

  In Reno?

• 53:04Tim Ferriss?

  Very, very, it was in Napa, long ago. And it was so

• 53:09Speaker 01

  I have a friend who, she loved it.

• 53:11Tim Ferriss?

  Yeah, it was a great event. It was

• 53:13Speaker 01

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

• 53:16Tim Ferriss?

  They do, they do. And it was opening, yeah, it was called opening the kimono, OTK. I actually have a wine bottle from that event over there because 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 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 J Cal recipe?

• 53:49Speaker 01

  In the Myers-Briggs, I'm going to say you're INTJ or INTP.

• 53:52Tim Ferriss?

  Nailed it. INTJ.

• 53:54Speaker 01

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

• 54:13Tim Ferriss?

  Yeah, that and the

• 54:15Speaker 01

  Astrology for dudes.

• 54:16Tim Ferriss?

  Astrology for men. Yeah, that's basically it.

• 54:18Speaker 01

  Like, we don't believe in astrology, but we believe in this other thing where we answer questions and it tells us things we want to hear about ourselves. But anyway, I scored 86 and 100% on entrepreneurship. I'm sorry, an extroversion, the two times I took it. So I'm so extroverted that when I'm with an introvert like yourself, or like say Evan Williams, a friend of ours, like I can burn people out. I'm just, I want to talk for seven hours. And like, when I've been on vacation with Tim Ferriss, it's like Tim Ferriss was like, well, that was like an interesting 90 minutes with J Cal. I need to go write for four hours and, or whatever, you need to recharge your batteries.

• 54:51Tim Ferriss?

  Take a nap.

• 54:52Speaker 01

  Take a nap, whatever. And I, if I talk for seven hours, I want to talk for five more. I just can't go to bed or I want to start working. And so I think once you, you have to understand your format. And I think the reason why you're the number one, you know, guy in podcasting is because this format works really well for you. You take a lot of time. To think about it, you do your 90 minutes and then you got a lot of time to decompress and process. For me, I do my show five days a week and All In six days a week. I like to talk every day. So, once you understand, I'm like the morning radio guy, right?

• 55:25Tim Ferriss?

  Yeah.

• 55:25Speaker 01

  And you're like the weekly 60 Minutes guy.

• 55:29Tim Ferriss?

  Yeah.

• 55:30Speaker 01

  Vive la différence. The problem with events is some people who are introverted, if they do an event, they need recovery time. And so for you to do an event, it should be you interview somebody on stage, you then go backstage and write some more notes, and then somebody else interview somebody, and then you come back out and do a Q and A with the audience, and then the event's over, and that's the totality of the events. I did a bunch of events because I realized if you can manifest a community in a real world space, again, back to like my childhood need to be important or have power, which was based on having no power and no money. And, you know, I feel like I've kind of processed that now, like I've kind of processed it, if I'm honest, like maybe 15, 20 years ago,

• 56:11Speaker 01

  I kind of figured it out. But I love the idea that if you host the party, those people get to meet new people, create some relationship or moment that then changes their life forever. And so what you should be very proud of with your Open the Kimono event is that to this day, people talk about it as a peak experience in their life. And when you think about what our lives are, in some ways, it's just like Blade Runner, when the Nexus 6 is on the roof and he says like, oh my God, all my, all my memories are going to be gone like tears in the rain. All we have at the end of this, I believe, I'm not a religious guy, I'm an atheist, but I do know that that singular moment in film is the most powerful moment in any film I've ever seen, and is kind of my spirit moment of any piece of

• 56:54Speaker 01

  cinema, or perhaps even literature, that that speech he gives, because that's what we, I think, human existence is about at its core. It's a series of memories you collect over time. You know, you and I playing basketball on that court, in the woods, in Italy, laughing our asses off, and then you figuring it out, right? It's just like, this is a weird moment in time, that when I just start- Describing it to you, you and I just start laughing. We're

• 57:20Tim Ferriss?

  Yeah.

• 57:21Speaker 01

  It's just a great Tim and J Cal moment that nobody else was there for. It's just the two of us, like literally in a basketball court, hidden in the woods in, on a farm in Italy somewhere that we discovered. It's a really beautiful memory for me and I think for you.

• 57:33Tim Ferriss?

  Yeah, for me too.

• 57:34Speaker 01

  And he just then, we'll get to the end of our lives and just like that Nexus 6, that has a, you know, this like four year lifespan and he's crying for the lost memories. Like that's all you have.

• 57:46Speaker 01

  And then gone like tears in the rain. So make those memories. And that opened the kimono event. I was literally talking to somebody not, yeah, I was, I was talking to them about it on um, Halloween. It was two weeks ago.

• 57:58Tim Ferriss?

  Very recent.

• 57:58Speaker 01

  And she was describing how that was like her favorite event. I was like, you've been to mine. And she's like, yeah, but that was the one I like best. And so just you can be proud of, even if that was the only memory that happened there, that was the only tear in the rain. You'll always have that, right? And so for me, that's what it is. People have these incredible moments and I have them. And I have now, you know, I'm 51. I'm just looking at the next number of years we have left and people of our age, like, Dave Goldberg passed, Tony Shay passed, you know, a lot of our friends are gone.

• 58:27Tim Ferriss?

  Yeah, it's wild.

• 58:28Speaker 01

  Gone too soon. And now I just look at it. I'm like, how many more memories can I put into the memory bank before the tears in the rain moment?

• 58:39Tim Ferriss?

  So let's talk about friendship because there are few things that come to mind when I think J Cal and friendship. 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 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 aware of it, a lot of things were 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 a lot of what you already said, but on friends. I want to say two things related to that. The first is, let me find this amazing quote.

• 59:23Tim Ferriss?

  All right. So this is a quote from Douglas Rushkoff. Yes.

• 59:28Speaker 01

  Oh, there's a good one. I put this on the back of my book.

• 59:31Tim Ferriss?

  Yeah. Jason would never stab you in the back. He might stab you in the face, though. So I really admire you as a friend. 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 going to get back to the other person. So I have a question for you, and maybe that'll be the first one about loyalty. The second question, because I do want to talk about All In, is going to be how you navigated starting a project with your very close friends?

• 1:00:14Tim Ferriss?

  And the conflict that ensued, because I have always avoided working, by and large, with my friends. So loyalty, where does that come from and why? And then, then the navigating, starting a project with your close friends?

• 1:00:28Speaker 01

  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 want to make sure that you two, you never leave your brothers behind. So that was like one of his rules. Like if you saw two of us, I'm like, where's your brother? Go get your brother. Doesn't matter if it's the oldest, the middle, on the middle, or the youngest. You three have to be by each other's side all

• 1:01:12Speaker 01

  the time. Never leave one of your brothers behind. Never let anybody say anything to your brother. Always fight. It's 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, you know, I might be full contact at times where if I disagree with somebody or

• 1:01:37Tim Ferriss?

  Bad times.

• 1:01:37Speaker 01

  At times I might be like, I don't agree with you or like, that's stupid.

• 1:01:44Tim Ferriss?

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

• 1:01:47Speaker 01

  Jesus.

• 1:01:48Tim Ferriss?

  What the fuck is wrong with you?

• 1:01:49Speaker 01

  What the fuck is wrong with you? I showed you, there's a little square box there. Just aim for the box. You missed the entire backboard. There's a little box behind the rim. So any way you could put the ball in the box. Your chances go up dramatically if you hit that box and you're like, okay, I got it. I'll put it in the box. But anyway, I like to laugh. I like to be loyal and I think like, I have a large number of acquaintances and then I have a small number of very close friends. That seems to me to be a good philosophy. And then somewhere along the lines, you know, people become transactional with you. You've had this experience. We've talked about it before. You know, everybody wants something from Tim Ferriss. Everybody wants Jason to fix their problems or they think they get a meeting with somebody who's more famous than the two of us put together

• 1:02:34Speaker 01

  that that magically is going to change their life because they got to talk to the person and tell them their ideas. I'm like, okay, you're delusional. Like this person does not care about your ideas and they're busy. So like, let Travis finish building Uber. He doesn't need to talk to you about your startup. Like, that's not going to make any difference. And, you know, it's just, there's something really special about being able to be supportive of your friends and being there for them because as you become more successful, the world, people think the world gets bigger. Oh, you have more money. Oh, your podcast went up the rankings. Oh, Tim Ferriss is on his 12th bestseller. The world gets smaller.

• 1:03:12Tim Ferriss?

  Yeah, it gets a lot smaller, a lot smaller.

• 1:03:15Speaker 01

  And then you're sitting home on a Saturday night when you're famous or affluent or rich or whatever combination of things you succeeded in your life, and it's a Saturday night and you're like, going out to this event is going to be arduous and painful rather than delightful. And what I realized is, you know, for people who have this in a more, even a more acute fashion than you or me, you have to create I think a safe space, a place where you can have like true friendship and talk about things that matter, your kids, your friendships, your spouses, your life, your hopes, your dreams, whatever, or just shoot the shit and watch a movie and laugh. And so it's kind of like one of the great things in life, I think, is friendships. The friendships

• 1:03:57Speaker 01

  you get are the effort you put into the friendships you have, right? And so people don't invest in it. And the people are so transactional. It's actually kind of weird. I was at a Halloween party and a lot of people were coming up to take pictures and I don't mind it at all. I'll take 100 pictures in a row. It's fantastic. You listen to the pod. I'm super happy. I suppose for you, it's a little bit annoying, the extrovert introvert thing. Like, I bet you can get through about three of them before you feel like you need to leave the party.

• 1:04:24Tim Ferriss?

  Yeah, then I need a bathroom break. I do that at dinners. I mean, I'll admit something embarrassing, but you won't be surprised. Maybe people listening will. If I go to a dinner with, or an event with more than eight or 10 people, I will leave the dinner every 10 minutes to go into the bathroom and just like close my eyes and breathe. I will disappear. And people are like, what's wrong with this prostate? But it's actually fine. I'm just so overwhelmed by the stimulation that I need to take breaks. It's really.

• 1:04:55Speaker 01

  Well, and now imagine it's people who are a fan of yours, or think that they can use you to achieve some goal, right? And literally all these influencers, this party, really like their goal is to just get a picture. And I was just had this like profound sadness for them. I'm like, if I was meeting me and I was an entrepreneur, like, a photo's great. But if you're a first time entrepreneur, like, maybe you should ask me about startups and running them or raising money, or there's a million things we could discuss. But the goal was to get a selfie? Like, who cares? You know, like, it just, so anyway, it's important to be, I think, a really good loyal friend. I have been burned in this regard,

• 1:05:37Speaker 01

  where I've been more loyal to certain people and they have not been loyal to me. And it's very frustrating for some of the people around me when they see that happen to me. And for me, I said, you know, that is that person's chance to learn how to be a friend. They just haven't gotten there yet. They don't understand how much more special it would be if they were reciprocating the friendship I was showing them. It makes it just even more rich. For All In, it is a very interesting thing, because you and I are solo acts. You have one duet you do. It's my favorite part of what you do is the random show with Kevin. Literally has had profound impact on my life.

• 1:06:14Tim Ferriss?

  Oh, wow.

• 1:06:15Speaker 01

  A big part of why I lost 30 pounds this year. You were telling me how good I looked. But I was in Italy a couple of summers ago and you and Kevin were talking about Ozempic. He 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 because I don't want to influence people. But I did a couple of, you know, series of Ozempics along with fasting that I've learned about from you and Kevin. And using the Zero Fasting App, which I learned about from the show. And then I 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 of cycles of Ozempic. I did the weightlifting. And I did the intermittent fasting using the Zero app and yeah, dropped 30 pounds.

• 1:06:57Tim Ferriss?

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

• 1:07:03Speaker 01

  I still have like, like to get five or 10 more pounds of weight, you know, of like muscle. And then be able to run a marathon again. So when I get those two goals, I would be pretty happy.

• 1:07:10Tim Ferriss?

  You can do that. You can do it. You can definitely do it.

• 1:07:12Speaker 01

  I'm in the window.

• 1:07:13Tim Ferriss?

  Yeah. So Solo Act suddenly decides, wait a minute, I want to be in a rock band. But I may not be allowed.

• 1:07:21Speaker 01

  Decide that actually.

• 1:07:24Tim Ferriss?

  So tell the story.

• 1:07:26Speaker 01

  What happened was Chamath and I had become friends.

• 1:07:28Tim Ferriss?

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

• 1:07:32Speaker 01

  All In is a podcast with four friends who are all capital allocators. In other words, like venture capitalists, investors and business builders in, um, yeah, I guess in all cases. And so four folks who are 50 years old with 30 years of business experience each. So that's about over 120 years building businesses or investing in them. Getting together and talking about business and then whatever the topics of the day are. But everybody's a little unique and different. And it started as something we did in COVID because we would all play poker together. And four of the poker players eventually wound up doing this every week, this podcast. And this is in decade two of me podcasting. And so I kind of created a format that I modeled after the McLaughlin Group,

• 1:08:15Speaker 01

  which was a Sunday morning show. So yeah, there's a guy, McLaughlin, you can look up some tapes of it. Anyway, this guy, McLaughlin was super cantankerous and he'd have like, you know, Republican, a Democrat, an independent, whatever, a young person, a Bostonian person, a California hippie, you know, whatever. And he was always cantankerous and moving the conversation along and he would say, wrong, and you know, do this. And it was like a very full contact, kind of dynamic, interrupt each other conversation. But you, it just, I was always drew me in. It's the best Sunday morning political show of all time, the McLaughlin Group. And so Chamath and I had known each other from AOL. He was working at AOL when I sold my company there, the blogging company back in the day. We had met, he became a venture capitalist.

• 1:08:58Speaker 01

  And then he met Mark Zuckerberg and he was one of the first employees at Facebook, grew Facebook from 10 million to 800 million users or something crazy like that. He was responsible for the growth team. Super intelligent, considered, fun, thoughtful guy, dynamic, aggressive, and just great leader of people. We became friends, we started playing cards together, joking, laughing. And I said, you know, I really would like to have you on my podcast. He wanted to be under the radar. He didn't want people to know who Chamath Palihopetia was, but he came on the podcast. In a lot of ways, like Chris Saka did, our friend was one of the first people. I think I was one of the first people to actually have him on a podcast when I did my two parter with him. So Chamath became a bit of a brand after he was on the podcast a couple of times. And then he keynoted a couple of events and we just had this rapport.

• 1:09:39Speaker 01

  And the rapport came from just breaking chops and laughing at the poker game every week. And then people saw that rapport when we were on stage. And then he said to me one time when he was coming out of CNBC. You know, we should just do a podcast together. I was like, yeah, come on this week in startups. He said, no, no, I want to do a different type of thing, just me and you. And you just bring up the news of the week. I talk about it, then I ask you a question and then you talk about it. And we go back and forth, startups, public markets, SPACs, public, private. I was like, that's a really good idea. Sure. Let's do it. And then we started texting back and forth and what are you going to call it? And I was like, we should give like a poker thing, since it's like poker, we should call it all in. And so the two of us started doing it, but this was during COVID. So then we're like, well, who knows about COVID? And Sacks had been doing a bunch of research on it. He had bought ventilators and he had masks and

• 1:10:21Tim Ferriss?

  Explain who Sacks is.

• 1:10:22Speaker 01

  So David Sacks is an old friend of mine who worked at PayPal with Peter Thiel, went to college with Peter Thiel, is a Republican, independent, really like chess club, debate club, brilliant product manager, created Yammer, sold to Microsoft for a million dollars, a billion dollars, just really smart individual, but right leaning, like seriously right leaning, like writing articles, donating to people on the right. And we became close friends. Our families would go on vacation together, just, you know, as close of friends as you could be. And then we had him on as a guest to talk about like, hey, what's going on with this Wuhan flu thing? And, you know, what's going on with Trump? And people were very scared and confused at the time. And then we had another friend who came to poker. I didn't have a big relationship with Freeberg at the time. I just knew him from poker.

• 1:11:08Speaker 01

  And David Freeberg, who runs something called the Production Board, he was an early Google employee, came on. And he actually is like, he created climate.com and sold that to Monsanto. So he understands science like in a very deep level. And so all of a sudden, you know, this thing clicks and then Robin Hood and that whole AMC thing happened. And I was an investor in Robin Hood and we started talking about that. And the show just caught heat and the dynamic between the four of us, people really started to like, and people were at home.

• 1:11:37Tim Ferriss?

  Caught heat in a good way.

• 1:11:38Speaker 01

  I think caught heat in like, wow, this is really dynamic. They're smart. They're opinionated and they're successful. And so when People see that you've made a lot of money is one thing I learned in my life is like the day before the Weblogs Inc. sale and then the day after when I had no money and then became a millionaire, people treated me incredibly different. Like all of a sudden I got like 30 more IQ points and I was two feet taller. I was like, I'm the same guy, but like people would just take you a lot more seriously. And it just is a really good thing to understand. Like literally, if you inherited a billion dollars, people would think you're a genius. It's a big failing of like human nature. Yeah. That we have this weird thing with the scorecard that we think the scorecard of dollars is like important. It's not. Long story short, all the stuff comes together

• 1:12:23Speaker 01

  and people, it seems to connect with people and it starts racing up the charts. And the last couple of weeks, I think we're in number 24, 26, 27, you know, like just top 30 podcasts in the world. Gwyneth Paltrow wrote about it in her group newsletter a couple of weeks ago that she's obsessed with the podcast and the personalities. And so, you know, this week in startups had millions of listeners every month and doing incredible five days a week, making millions of dollars in advertising, but it's a very niche thing. It's just about startups. So if you're in the startup space, like you would want to take a selfie with me. All in has crossed over in a way like you experienced with the Tim Ferriss podcast and, you know, people who are pursuing excellence. It's a much wider aperture of people. And

• 1:13:05Speaker 01

  so this thing just appeals to a lot of people and it's literally, people say it's like their Sunday morning ritual or their Saturday morning ritual. It's replaced the Sunday morning talk show. And it turns out Politico is writing some kind of a profile of us right now because it's become so influential in Washington because we talk about the economy, technology and technologies that have a big impact on the economy and politics, whatever. So anyway, in some ways, it's become a hit. It's very weird for me because, you know, I've had a couple of hits before, but this one also is bigger and I'm not in control of it. I have three partners and all three of my partners on it have never had a boss. So you've literally

• 1:13:46Speaker 01

  got four of the most opinionated friends who have never had a boss, who have four different directions they want to take it. And it is a bit chaotic and I'm the producer of it as well. And, you know, did all the work, came up with the format, et cetera. But objectively, you know, Chamath has a series of fans, Freeberg now has his stands, Saks has the whole right wing. So it's like a super team has come together.

• 1:14:12Tim Ferriss?

  Yeah.

• 1:14:13Speaker 01

  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.

• 1:14:21Tim Ferriss?

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

• 1:14:27Speaker 01

  Well, I wanted to do an event because you mentioned like events. And I was like, let's do this all in summit. I'll do all the work and you guys show up. I have a production team and here's what it will be. And one of the four of us was in a complete panic and complaining and arguing incessantly because 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. I invited you, you didn't make it, but I'll get you next year.

• 1:15:07Speaker 01

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

• 1:15:12Tim Ferriss?

  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 want to say in three or four years. Yeah. So, but.

• 1:15:25Speaker 01

  There'll be an opportunity. I'll interview you. No, there'll be some opportunity where you'll like, it'll be a fun thing for us to do.

• 1:15:31Tim Ferriss?

  And in my own defense, I have been to events of yours before. I've gone to, I have spoken with you at, at events. So I couldn't make that one.

• 1:15:39Speaker 01

  Couldn't make that one. Yeah. Okay. That's true.

• 1:15:40Tim Ferriss?

  So wait, where does the conflict come in?

• 1:15:42Speaker 01

  So the conflict came in that I just told him like, hey, listen, I'm working over here. 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. What if it's bad? People paid 7,500 tickets. I'm like, some people pay 7,500 on a ticket for every event. Like, it's not a big deal. And then I gave half the tickets for scholarship for people. Anyway, we had this back and forth. And then I told the person like, you know, Freeburg, I was like, Freeburg, if you don't want to be on the show and you're complaining so much, I got Brad Gerson over here.

• 1:16:13Tim Ferriss?

  I love how he was anonymous up until right now.

• 1:16:15Speaker 01

  Whatever. The good news is Freeburg and I, after this blowout, like many friendships, we actually are really enjoying our time together. But it was another one of these like stabbing in the back, stabbing in the face thing, you know, like as you got the quote from Doug. I said, listen, if you're not enjoying your time on the all in podcast and you don't want to do the event, why don't you do 25 episodes a year and I'll have Brad Gerson who comes, who sits in when one of us is out as like the fifth Beatle, I'll have him do the other 25. We got this big fight and the whole thing's going to explode. And then they're, you know, these two are going to do their own podcast, whatever. And then we all just sat down and we realized the audience fucking loves this. We love it. Let's not do any events. Let's not do any spin outs.

• 1:16:53Tim Ferriss?

  Yeah.

• 1:16:53Speaker 01

  People wanted to do a TV show with us, you know, top networks, you know, all this stuff. And you understand how big the podcasting business now is better than anybody, you know, you got a top 50 podcasts. Like these podcasts have become a very big business. On top of that, my biggest media success to date with my three partners, refuse to do ads.

• 1:17:13Tim Ferriss?

  Yeah, this is one I hope, I was hoping you would bring up. So, yeah.

• 1:17:17Speaker 01

  So I'm sitting here on, you know, arguably $25 million in advertising, which I would get a fourth of. And they're like, Sacks is like, well, I'm already rich and I got a plane. And Trumon's like, well, I got a plan. I'm already rich. I don't need a, I don't need advertising. I'm like, I'll read the ads. I'll sell the ads. They're like, it's so cheap to have an ad. And I'm like, no, it's not. It's like, everybody's got ads. It's just an ad. People listen to the ad. They drink some Athletic Greens. Athletic Greens is healthy for you. But we're done here. Like, who doesn't love Athletic Greens?

• 1:17:50Speaker 01

  We're good, you know, like.

• 1:17:51Tim Ferriss?

  Yeah.

• 1:17:52Speaker 01

  Sorry to give Athletic Greens. Use the promo code TIM, not J. Cal. Use TIM, not twist.

• 1:17:59Tim Ferriss?

  Oh, I love, I love AJ. I was just texting with the CEO Chris like 45 minutes ago. Yeah, anyway.

• 1:18:04Speaker 01

  You know, I had it this weekend. I made a really good ginger and some other juices. I know people drink with water, but I like a little juice. And what I do is now I use half the amount of lettucre greens, but I do it twice a day. I kind of like to space out.

• 1:18:18Tim Ferriss?

  I like the ginger.

• 1:18:19Speaker 01

  Slightly different, but the ginger, when you blend that ginger, you have that spicy. Mmm, yummy, yummy.

• 1:18:24Tim Ferriss?

  But your partners were not buying the ginger cocktail.

• 1:18:27Speaker 01

  No, so literally like I could use another seven million a year, you know, like this is, this is big cash. Six or seven millions.

• 1:18:33Tim Ferriss?

  It's a lot of money. It's a lot. It's a lot of money.

• 1:18:35Speaker 01

  Well, after taxes, it would be a jet.

• 1:18:37Tim Ferriss?

  Yeah.

• 1:18:37Speaker 01

  So no, I have no jet.

• 1:18:41Speaker 01

  This is when this, this podcast, this, this episode is going to get clipped like crazy.

• 1:18:44Tim Ferriss?

  So good.

• 1:18:47Speaker 01

  Let me have a jet. You're standing between me and private aviation.

• 1:18:54Speaker 01

  I'm being a little facetious right now, but you know, it's not exactly facetious.

• 1:18:58Tim Ferriss?

  Yeah.

• 1:18:59Speaker 01

  So anyway, I just said, you know what? I'm not going to try to monetize this anymore. We're not going to do live events. It causes too much chaos. Let's just do it every week and then I'm, I'm raising my next venture fund, launch four. And I decided to raise it publicly. You can, if you pick a designation 506C, you can say, I'm raising a fund. So I said, guys, would it be okay if on the podcast I mentioned I'm raising a fund? And people can email me, [email protected]. Boom. All of a sudden I get a thousand emails. People are like, oh yeah, I'm a rich person. I would love to be an investor in your fund. I do five webinars.

• 1:19:33Tim Ferriss?

  I really hope the emails read exactly.

• 1:19:36Speaker 01

  Basically, it's like, oh, hi, Jay Cal. I'm a huge fan of all in. My family office, I went to this, we saved the whales and we love, we're big fans of the pod.

• 1:19:44Tim Ferriss?

  Translation to 140 characters, I'm rich. Can you make me richer?

• 1:19:48Speaker 01

  Basically. And so I kid you not, I do five webinars, the last five weeks. $44 million in commitments.

• 1:19:54Tim Ferriss?

  Whoa.

• 1:19:54Speaker 01

  From people I have never met. My last fund was 44 million. I have not done an in-person meeting yet. So I said, you know what? Now, listen, for people listening in the venture fund, I have to deploy that money, triple it, and then I get 25% of it. I don't get the 44 million. It's not a donation. It's like what I do for a living. But holy cow. I was like, I don't need to have the ads on it. I can just play the long game and raise a larger venture fund and meet a bunch more of these LPs or whatever. But every LP meeting I have, or most meetings I have now, start with, hey.

• 1:20:27Speaker 01

  Can I take a selfie? And this is my favorite thing about All In. And so, you know, it's like, I had to come to peace with the fact, all four of us, that we hit lightning in a bottle. That's number one. Number two, we have to trust and love each other and put on a good show. And we have to be rooting for each other. And I said to everybody, like, if we're gonna do this, let's be rooting for each other. And that means when you're having this debate and you disagree with me and like, Sacks and I have had blowout battles over like Ukraine. And I'm like, listen, Putin needs to be stopped. And he's like, Biden and these people are tempting a nuclear war. This is a very important debate.

• 1:21:05Tim Ferriss?

  Yep.

• 1:21:06Speaker 01

  And it gets very heated. And, you know, people think Sacks and I hate each other. Sacks and I love each other deeply, even though he can't say it. I can say I love Sacks and I know he loves me. And what I hope happened from that podcast is people see that, you know, we can have a brawl, still love each other, still respect each other, and still make forward progress and learn from each other. And, you know, Sacks is right about a lot of the things with Ukraine. We should have maybe tried for peace earlier. A lot of the things he said actually turned out to be right. Now it seems like Biden is saying to Zelensky, maybe you guys can start working on negotiations now and maybe we won't give you an unlimited supply of support. Like, we're giving you the weapons. Can you please sit down and try to work this out? But it has created chaos.

• 1:21:49Speaker 01

  And because the podcast is so popular, Tim, it's like a lot of things, like, people maybe give it a little too much credit.

• 1:21:54Tim Ferriss?

  Well, yeah, you start to have a very big responsibility.

• 1:21:57Speaker 01

  Exactly. You nailed it. That was, that was, that's what I was thinking. Like, now people are calling me saying, hey, you gotta get Sacks in line. And then people are calling Sacks saying, oh, J. Cal hates Trump. He's got Trump derangements. I mean, everybody is 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 right to have a conversation about affirmative action in this Harvard case? 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, 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.

• 1:22:42Speaker 01

  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, is now Politico, I'm sorry, Vanity Fair 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. And we were sitting here 18 months ago, and when different people in the podcast were saying, well, maybe it's a lab leak, they were like, well, we have to take that podcast down now. We can't have that conversation that it's a lab leak?

• 1:23:23Tim Ferriss?

  Yeah.

• 1:23:25Speaker 01

  There's two labs in the world that are studying the Wuhan virus, and one of them is the one where COVID happened and 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, talk about a topic, because their shows are popular.

• 1:23:47Tim Ferriss?

  Yeah, yeah.

• 1:23:48Speaker 01

  And we have to work this out, because you are allowed to have a conversation, and people need to come to their own truth. And sometimes institutions do a great job, sometimes they fail us. But we should all debate these issues.

• 1:23:59Tim Ferriss?

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

• 1:24:01Speaker 01

  Please tell me.

• 1:24:02Tim Ferriss?

  Where I say my protocol. My protocol is, if I'm going to 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, then I'll add in very strong disclaimers, and then I will not look at Twitter for at least a week.

• 1:24:26Speaker 01

  Yes.

• 1:24:27Tim Ferriss?

  It's very simple. It's like, 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.

• 1:24:33Speaker 01

  You will get ouch my balls, like literally like Idiocracy, the TV show, ouch my balls. Like you're gonna get your nuts kicked.

• 1:24:39Tim Ferriss?

  Yeah, yeah.

• 1:24:40Speaker 01

  Over and over and over again, just for having a conversation. I think, I thought Joe Rogan did a really good job when they were like, hey, you're having these people on, they have uncertain, whatever. And he's like, I'm a comedian. And like, yeah, you're a comedian with 10 million or 20 million viewers. And he's like, you know what? If I get it wrong, tell me who to have on, I'll do it again. But again, I'm a comedian interviewing people and trying to learn. And I actually think there's a little bit of responsibility on the audience's part here. You know, he's a comedian.

• 1:25:09Tim Ferriss?

  There is. However, I'm gonna push back a little bit and just say that I do, well, decline or through vetting, disqualify probably 80% of the people that might be on the show because I do a lot of fact checking ahead of time. And I will do scientific fact checking, reference checking. And if it seems like someone is playing it too fast and loose, they do not come on the show, generally speaking. So I do a lot of heavy lifting on the front end, which if someone's goal is to learn and they're not a domain expert, I think is incumbent upon them if they have a large audience. And I'm not saying Joe doesn't do that, but I do think.

• 1:25:48Speaker 01

  Well, he said he doesn't do it. He said, I don't come in prepared. Just to be clear, when this whole thing blew up, he said, I want to let you know, I do not come in prepared. Sometimes I just have like, somebody hands me notes. He said, and I'm thinking about changing that. So I do think if he's going to talk about like medical stuff, he should have a researcher do some stuff.

• 1:26:05Tim Ferriss?

  I mean, you're a very close friend of mine and like.

• 1:26:07Speaker 01

  Yeah. Look, yeah, I know you do research. I mean, but also.

• 1:26:10Tim Ferriss?

  I've got 20 pages of notes. Yeah.

• 1:26:12Speaker 01

  Which is why when you talk about whatever topic you're talking about, the audience has an expectation that it's going to be tight. When people go into Joe Rogan, they should have the expectation that he just walked in unprepared or modestly prepared. That's where like, I think. Audiences have to take some responsibility. It's probably between the two things we're talking about.

• 1:26:31Tim Ferriss?

  It's between the two. And, you know, I think that, and he might not want to do this, but you know, if Joe wanted to do something preemptively, it's just like at the very heading of the show, there could be sort of a disclaimer of the kind of disclaimer you would see on Jackass back in the day, which would be like, these are trained professionals. This is for entertainment.

• 1:26:51Speaker 01

  Yes.

• 1:26:51Tim Ferriss?

  And like, do your own homework.

• 1:26:53Speaker 01

  Actually, I have an idea for Joe Rogan. I think he should start a second podcast. It'll make tens of millions of dollars called After Joe. And it should be a group of experts vetting whatever was talked about or goofing on it.

• 1:27:08Tim Ferriss?

  That's a great idea.

• 1:27:09Speaker 01

  And After Joe, Post Joe.

• 1:27:11Tim Ferriss?

  Yeah.

• 1:27:12Speaker 01

  And it would just be like a breakdown of what happened on the episode. And then he could say, listen, yeah, did you listen to After Joe or Post Joe? Post Joe wrote a webpage, like you do great notes, and there's people who do show notes of both of our shows once in a while that are pretty good. He should just pay somebody a thousand bucks to do a show notes. They make so much money. Pay three people $2,000 each. Just spend five grand on like, this is a medical episode, vet it, put a bunch of links in it. That would just make it so much better, right? I think.

• 1:27:37Tim Ferriss?

  So I have a question, since I did call you Podcast Master in the beginning, and I want to put on a showcase for a moment. So you and I have offline talked, well, I guess probably online, but offline meaning non-publicly, talked about how you prepare privately. Jesus, what am I? Am I a writer? I used to be. Words. Use your words, Ferris, privately. So we've talked about your moderating. I think you are one of the best moderators I've ever seen. And it's true. And that is absolutely, I would say that to anyone. I think I'm actually pretty sure I have said it publicly and

• 1:28:15Speaker 01

  You have, actually. Thank you for that.

• 1:28:16Tim Ferriss?

  Yeah. And I'd like to look at the mechanics and the preparation that goes into that. 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 going to see, like raising your hand and using visual cues for things. So could you walk through what the preparation process looks like for a good episode?

• 1:28:43Speaker 01

  So we build a docket every week for All In. The docket I took from Red Scare, which is like this dirtbag left podcast of these two women who live in the dime square in New York. They're quite charming and hilarious, probably a little cutting edge for some people. But anyway, the Red Scare podcast is hilarious. And Dosh always says, oh, what's on the docket? And I have a docket, like, you know, these are the people who are going to pass judgment on, like, 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.

• 1:29:17Tim Ferriss?

  So the docket is a Google Doc?

• 1:29:19Speaker 01

  Yeah, Google Doc.

• 1:29:20Tim Ferriss?

  Okay.

• 1:29:20Speaker 01

  Of topics.

• 1:29:21Tim Ferriss?

  And then this is put into a private Slack channel that you guys use or something like that?

• 1:29:24Speaker 01

  Yeah. Yeah, we're on Signal. Yeah. And so we, we, yeah, that's where they all disappear within a week. Hard lessons to learn. Thank you for getting it. So anyway, Signal. You can reach me at Signal.

• 1:29:37Tim Ferriss?

  So now, do you use desktop client for that to make it easier to use? Or do you do it all on mobile?

• 1:29:42Speaker 01

  Signal is desktop and mobile now. Yeah, it's pretty great. And it's not owned by the Russians. I use mobile and I use the desktop.

• 1:29:48Tim Ferriss?

  Okay, great.

• 1:29:49Speaker 01

  Anyway, we, we have, I have the bullet points in there. And I will sometimes push people to come up with topics. So like, hey, when Friedberg was kind of sitting back a lot in the episodes, I kind of dubbed him the Sultan of Science. And I kind of created this character. And I said, you know, listen, you're, you're kind of like a little bit of a wallflower last episode. Can you give me whatever the most interesting science story of the week is? And if I don't get one by, you know, whatever, a day before taping, I'm like, hey, and maybe I'll do a little research myself. Hey, what do you think of this? Or what about that? And when I get a science topic out of him, I throw to him. And, you know, he just lights up. It's great. And then, you know, Chamath will make a joke, or Sax will go check his email. And then for Sax, I throw him red meat. So like, the red meat for Sax is like, anything political, anything to do with the Constitution,

• 1:30:34Speaker 01

  anything to do with the Supreme Court or legal cases. And then, if I want to give an alley-oop to Chamath, so I think about as the moderator, I got to get out of this guy, I got to get him engaged, Friedberg. I got to give him some science, so that he gets excited. Because he's not excited to talk about politics, because he doesn't like it. With Sacks, I got a tiger.

• 1:30:55Tim Ferriss?

  Yeah.

• 1:30:56Speaker 01

  And all like a fierce tiger. And if I throw a couple of chickens out there, he's gonna maul them. And I know what they are. So I'm like, okay, here you go. Supreme Court decision. He loses his mind. Oh, here you go. Biden said this and it's inconsistent or boom. Hey, here's something with Trump. He's gonna just go crazy. So now you got your lion going crazy. You got your science nerd coming out of his shell. And then with Chamath, it's more like an alley-oop.

• 1:31:19Tim Ferriss?

  Sweaters.

• 1:31:19Speaker 01

  I know. What was that sweaters? Lurpianna. Conspicuous consumption. No, it really is more about markets and startups. And for him, I like to say to him, can you explain this financial topic? And why people are talking about interest rates are bad for tech companies? Why would the interest rate have any impact on that? Now, I know the answer to that. But he can actually explain it better than anybody on the squad. So what I'm doing there as the point guard is like, I have a clear path to the basket. I can just lay it in and do the layup. But I see him out of the corner of my eye. And I'm like, you know what would make the audience have a better experience? Is if I pretend I'm gonna do the layup.

• 1:32:02Speaker 01

  And then from behind my back, I throw it up to him and he slam dunks it. Right? And so I've learned with each of them, how to feature them and make them really their best selves. And then behind the scenes, you know, when you see the point guard in basketball, like take somebody and they whisper in their ear or something? I very quietly give them notes on their performance.

• 1:32:25Tim Ferriss?

  And this is after each episode or?

• 1:32:28Speaker 01

  After each show. I did it, had to do it more earlier. And then sometimes I'll do it in the group chat. If I think it's something everybody can benefit from. But more often than not, I'm doing it quietly.

• 1:32:38Tim Ferriss?

  Yep.

• 1:32:39Speaker 01

  And so, you know, I had to say to Freeberg, listen, you don't say a lot about politics, but I think your opinion actually represents a large portion of the audience. And although you hate it, I think you expressing a little bit. Is going to be fine. And if you're not happy with how it comes out, and I think it's putting you at risk, I will tell you and we can cut it from the show. And once I gave him that sort of like, I think, a little bit of a clear lane and encouragement, you will hear him talk a little bit more about politics, not to the extent Sax does. And then I had to tell Sax, hey Sax, when I ask you something or I challenge you, I am not disagreeing with you. I'm helping you clarify your position, or helping the audience understand your position more.

• 1:33:21Tim Ferriss?

  That's a very smart way to put it.

• 1:33:23Speaker 01

  And you are attacking me, telling me I'm watching MSNBC and I get my information from Rachel Maddow. I didn't ask you to explain, like, one time, I said, just to be clear, Putin invaded Ukraine, not Biden, correct? And he just went off or whatever. And I said, you know, the reason I'm asking you that is because the audience thinks, and the feedback online is, you're a Putin apologist. It would help your position if you said to the audience, Putin and Putin alone is responsible for invading Ukraine. Now, how we manage Putin and his unjust, immoral invasion is, you know, up to us, right? And that's what we

• 1:34:07Speaker 01

  can debate. But I'm trying to save him from being misunderstood, right?

• 1:34:11Tim Ferriss?

  You're like, you're like, one part moderator, one part coach, one part comms director. I'm not saying that is a bad thing. It's just like-

• 1:34:22Speaker 01

  No, no, no. I think it's super accurate.

• 1:34:23Tim Ferriss?

  You're helping everybody.

• 1:34:24Speaker 01

  Yeah. What I realized was, like, listen, I've done, you and I have done, you know, hundreds of interviews with people. Great. It's awesome. We're both interested in people and learning from them and having great conversations. But this became something different for me, you know, being the orchestrator of the action.

• 1:34:41Tim Ferriss?

  It's a different, it's a different skill, different skill.

• 1:34:43Speaker 01

  It was a totally different skill. And, you know, I had done these moderations before at events, and I had sometimes done roundtables, news roundtables, but a lot of times I was one of the featured players, not the point guard, right?

• 1:34:53Tim Ferriss?

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

• 1:35:06Speaker 01

  Yeah, there's two techniques, two techniques, very, because 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 have 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 two. 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

• 1:35:48Speaker 01

  or four of the points. And then if somebody comes in and they're just like, ding ding ding ding ding, I just took all the good points. There's nothing left for anybody else to do. And so you want to share the ball a little bit. You took two good points. You let somebody else make a good point. Yeah, you could have made that point. It was an obvious one. But you let somebody else have. It's a little bit generous as a performer. So it'd be like, you got some incredible guitar player. They come out and they just do a solo of six minutes. And you're like, piano guy could have done a solo for a minute. You could have done two. We could have given the drummer a minute. And they could have let the vocalist lead off the song with an a cappella moment, right? 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 for interrupting certain people. And so I had

• 1:36:32Speaker 01

  to actually adapt to that. Because certain people, if you interrupt them, it's a trigger for them.

• 1:36:38Tim Ferriss?

  Yeah.

• 1:36:38Speaker 01

  Or it can break their train of thought.

• 1:36:40Tim Ferriss?

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

• 1:36:45Speaker 01

  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, 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 difficult to do that.

• 1:37:23Tim Ferriss?

  Forboding, yeah.

• 1:37:24Speaker 01

  Forboding, that's the word I was looking for. My dyslexia was killing me on that one. For written, forboding, it's forboding, right? You let people finish, but he'll say, okay. And it's like, okay, I got it. Okay, you did it. And then the person's like, oh, Sam has something to add. And that's in a one-on-one situation. So, you know, you get good by studying, you know? I study a lot of what you do and I, you know, you have a way when you're asking a question of slowing down and it's almost as if you're bringing us into your brain for the formation of the question. That was me imitating you.

• 1:38:06Tim Ferriss?

  Yeah.

• 1:38:07Speaker 01

  And when you do it, it's like somebody at a dinner party who's talking in a lower voice and everybody leans in. I know it's going to be a fucking important question when you do that. And I don't know if you've, it's unconscious or it's conscious, or you are truly forming the question. But when listening to Tim Ferriss, when Tim slows down and Tim is thinking, I want to ask you one more question. I have it on this note here. It's, hold on. Now, it means it's a really important question and it really does work as a technique. And, you know, everybody's techniques doesn't have to work for everybody. Like I talk fast.

• 1:38:48Tim Ferriss?

  Yeah.

• 1:38:49Speaker 01

  You talk a little slower, more methodically. Sam talks even, you know, more monotone.

• 1:38:54Tim Ferriss?

  Speaks in finished prose.

• 1:38:55Speaker 01

  Unless it's about Trump and then he gets untold. It is funny how we all study each other, right?

• 1:39:02Tim Ferriss?

  Oh, yeah.

• 1:39:04Speaker 01

  Moderators club.

• 1:39:05Tim Ferriss?

  I love doing it. I mean, I remember doing so much studying in the beginning. I'm still studying and it's fun to notice because when you're in the game and you're doing a lot of interviewing, I don't do as much moderating, so I can't speak to that. But you begin to notice, just like you noticed, you begin to notice the little things that were you not also doing a lot of reps, you wouldn't pick up. And 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?

• 1:39:37Speaker 01

  There's not a big cohort of moderators because almost everything is, yeah, I mean, you might say, um, what's his name from, um, Politically Incorrect?

• 1:39:49Tim Ferriss?

  Bill Maher?

• 1:39:50Speaker 01

  Bill Maher. So Bill Maher, you know, he can drop something funny into a moderated bit. So two people are talking. You know, I do a little comedy on the side and will sometimes make jokes during the podcast. And I have seen him do this particularly well. He's watching two people spar and he's kind of 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 superheated and then you drop something funny and you'll see me do this on All In. It kind of just cracks the whole thing open. Everyone's like, okay, that was getting really serious, but we're all humans and we can laugh too about it. So somebody's having some crazy debate about like Roe v. Wade and then he makes some joke, you know, and you're just

• 1:40:32Speaker 01

  like, whoa, 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, 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. I think you could pull it off. I think with your great rapport with Kevin Rose, and if you got one or two more, you could do your own little All In, McLaughlin Group thing. It would be quite successful, I think.

• 1:40:59Tim Ferriss?

  Yeah, I guess it comes down to the, the chemistry. Like, 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, your styles just work for some reason.

• 1:41:10Speaker 01

  Yes.

• 1:41:10Tim Ferriss?

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

• 1:41:17Speaker 01

  It wouldn't, you know, when you look at your podcast player, if I see random show, that's just like, I snipe that immediately. Like, when the random show comes up in my feed, because, you know what? We were going back to friendship. We talked, we kind of spent a little time in this conversation. Friendship is so special, right? Like, it's like one of those very special things in the world's unique. And when people see friendship, like true friendship, It's such a like intoxicating thing.

• 1:41:41Tim Ferriss?

  Yeah.

• 1:41:41Speaker 01

  To know that you and Kevin are having a great time catching up and we get to be there for it. It's just to, 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? And then when the show was gonna break up, oh my God, what's going on? This just sucks, man. People wrote me very long notes like, you know, I really think you guys need to think about the fans and what the impact is gonna have on us. And I was like, I feel like we're in Pink Floyd and like Roger Waters and Gilmore like doing separate tours. And they're like, it's the same songs, folks.

• 1:42:24Speaker 01

  You could just listen to the old albums.

• 1:42:26Tim Ferriss?

  I think there's another piece which is right parallel to this. And that is 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?

• 1:42:41Speaker 01

  Yeah, no, when we had our, just now in our conversation, when we were bringing up Ouch My Balls from Idiocracy, I was like, oh, we're going there? Oh no, are we gonna get canceled for liking a funny bit in a movie?

• 1:42:53Tim Ferriss?

  Yeah, and the fact of the matter is, is 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, all of us would be unmasked.

• 1:43:09Speaker 01

  Yeah.

• 1:43:09Tim Ferriss?

  For the complete children that we all are. And despite that.

• 1:43:14Speaker 01

  Goofballs.

• 1:43:14Tim Ferriss?

  Given the times, I think the majority of folks feel like they 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 are having fun, they're not taking themselves or anything too seriously, even though they do take things seriously in life. It allows everyone to just exhale for a second.

• 1:43:38Speaker 01

  Yeah, chill out. It's gonna be okay.

• 1:43:40Tim Ferriss?

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

• 1:43:43Speaker 01

  It's very weird like being a Gen Xer 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? Just a window. Like you can pick how wide or open you want it to be, but people are really. Trying to narrow the topics you can discuss in a way that I find kind of a bummer.

• 1:44:09Tim Ferriss?

  Yeah.

• 1:44:09Speaker 01

  You know, because all those conversations are still going to occur. They're just going to occur in private. I almost would rather they be occurring publicly so we could make more progress as a society. It feels like.

• 1:44:19Tim Ferriss?

  Yeah, I agree.

• 1:44:20Speaker 01

  It feels like it's going to work against us. I hope it opens up. That's why I was talking about that Red Scare podcast. Or another podcast I like is the guy who wrote Less Than Zero and American Psycho, Brett Easton Ellis.

• 1:44:32Tim Ferriss?

  Oh, yeah.

• 1:44:33Speaker 01

  He has, and both of these are on Patreon and both of these are behind paywalls, which I think is interesting.

• 1:44:39Tim Ferriss?

  Yeah.

• 1:44:39Speaker 01

  Both of them are podcasts where people are being an Overton window that's twice as wide open and.

• 1:44:47Tim Ferriss?

  Just for folks who are listening, if they don't know, Overton window.

• 1:44:50Speaker 01

  What's allowable to discuss in society writ large or, you know, I'm using a fancy word. What you're allowed to talk about in society without feeling ashamed or that you're being inappropriate. So.

• 1:45:02Tim Ferriss?

  Or that you're going to be persecuted or.

• 1:45:05Speaker 01

  Or persecuted for sure. So there was a time when, you know, just even talking about somebody being a homosexual was outside the Overton window. And if you brought it up, everybody would leave the dinner party, be aghast, oh my God. So you had to just like treat a person who was a gay person at a dinner party as like, oh, they, yes, they've got a roommate, you know? And like, we're just going to sweep that under the rug like they're, oh yeah, they're here with their roommate. They split their rent because it's cheaper. And then you could be like, yeah, Ernie and Bert are gay. They're roommates.

• 1:45:32Speaker 01

  Pretty obvious.

• 1:45:33Tim Ferriss?

  I like the, the little judo movie did with the Ernie and Bert there, like the jelly and peanut butter. I was like, whoa, wait a second. Oh, wow. I'm just now.

• 1:45:42Speaker 01

  Okay.

• 1:45:42Tim Ferriss?

  Yeah, I like it. I like it. So you have this experience with these friends. You built this podcast. 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. Every example you've given, I think from at least your earlier career, shows how systematic and methodical you are. So I don't, I know it wasn't an accident. It may have coalesced in a way that couldn't have been predicted, but I don't think it was an accident. So how would you explain the popularity? Like, what are the ingredients? And then secondly, how do you now think about success for yourself?

• 1:46:28Tim Ferriss?

  You made that joke earlier about being separated from the success power piece.

• 1:46:32Speaker 01

  I think there is something that comes from repetition and getting reps in and you and I are both big fans of that. And so I think having done whatever at the time, maybe 1300 or 1400 episodes of This Week in Startups and all those events, 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, a different, my skill set, 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

• 1:47:16Speaker 01

  like, wait, aren't there like two for 10,000 people in Brooklyn? And you have to wait like to get on it. And then I have one where I can just sit there and like, let it go unused for a month. Ping pong and tennis is the same thing. There's a net, there's a ball, you just put spin on it. And I started taking tennis lessons this year. And it was like, woo, you know, your brain kind of lights up. Same thing, but different. Same skill. So I think that 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 I'm a better moderator than an interviewer. Maybe that actually was sitting there the whole time. Maybe I'm a better

• 1:47:58Speaker 01

  tennis player than a ping pong player. So that, for me, I think has opened up a lot of possibilities of what I could do with the last 10, 20, 30, 40 years, whatever I got left on this planet, before the tears and the rain, you know, 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 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 of me, you and Travis were sitting around, or me, you and Matt Mullinweg were sitting around, and we took out our networks, and it was like, oh, my God, like, you and I are down here, and these two guys are up here.

• 1:48:38Speaker 01

  We all go and have a steak. Steak tastes the same. We all go and go skiing, or we go to Japan, same experience. And once I realized that, I was like, for me, it might be different for other people.

• 1:48:54Speaker 01

  The scorecard of cash doesn't matter beyond a certain point. And for me, it was the freedom to do whatever I want in my life and to take care of my three daughters, take care of my wife and be a good provider, take care of my extended family if they needed some help on the margins. And once that happened, I was like, I actually, I drive a Model Y and I prefer that to the Plaid and I have a Model X. Like, you know, like I enjoy sometimes the New York strip better than Wagyu. I just kind of like the flavor of it. It's a fifth of the price. So, once you start to realize like, okay, this is, these are just constructs and money is just not the right scorecard. The right scorecard is, did you wake up and couldn't wait to get out of bed? Like, to me, that's the true scorecard. I cannot wait to get on air and do This Week in Startups with Molly and talk about tech.

• 1:49:39Speaker 01

  Can't wait to meet with founders. I can't wait to teach another course on how to start a company. Can't wait to see my friends for dinner. Can't wait to help my friends if they're in need. Can't wait to come on the Tim Ferriss Podcast. If I can't wait to do the activity, I know I'm doing something right. When you invited me on, I went to Jade, I was like, my wife's name is Jade. And I was like, oh, you know, Tim invited me on the podcast. I can't wait to do it. That very rarely happens. But I was like, you know, I listen to the Tim Ferriss Podcasts all the time and I'm sure at some point I'll be on it. But the act of doing it with you, to me, was like, oh, I'm excited, you know? And being excited and enthusiastic, to me, it just means something has aligned. And, you know, when I'm writing, you and I have the same thing. When you get, I don't know where it is for you, but somewhere around like a third of

• 1:50:24Speaker 01

  the book, things start heating up for me. And like, all of a sudden, like, you know, the first third of the book is like, oh! And then all of a sudden, oh, I know what sections I have to do. I can see behind the next corner. The book just flows and you're like, boom, 2,000 words are coming out at a clip. And, you know, like, those kind of moments, when you have that flow and you have that enthusiasm for life, you have to construct a life around those. And then life is just pulling you out of bed every day and just telling you like, oh, I gotta go to bed. Like, every night I go to bed and I'm just like, I don't want to close my eyes. I want to just...

• 1:51:00Speaker 01

  Do another hour.

• 1:51:01Tim Ferriss?

  Yeah.

• 1:51:01Speaker 01

  It's hard for me to go to bed some nights because my enthusiasm is so high for life. And, you know, it wasn't always that way. A lot of it was a struggle. A lot of it was trying to figure out who I was. But I really do want to enjoy this last couple of decades of if there's an interesting project or moment that's going to create that great memory and going to make me enthusiastic, I want to do it. And if, you know, that means helping out a friend on a special project or going on a friend's podcast or whatever, doing a new podcast. It's, it's just, you know, I feel very blessed that I got here and I want to just squeeze every single drop of juice out of that, you know, box of oranges.

• 1:51:41Speaker 01

  I mean, really, I mean, think about it. Our friend, Dave Goldberg, rest in peace, you know, Tony Shay, you know, the darkness there, it can be over. It's exactly like our age range where we start saying goodbye to people. And so if you're in your twenties or thirties, like you're just on adrenaline and then you get to forties and fifties and you're like, huh, what do I do with what's left? Especially if some things have hit for you, you know, like if you're Tim Ferriss and like, you gotta really start thinking like, okay, well, I'm one of the top podcasters in the world, one of the top authors in the world. Is this actually making me happy?

• 1:52:15Tim Ferriss?

  Yeah.

• 1:52:16Speaker 01

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

• 1:52:22Tim Ferriss?

  Yeah, I can't wait to read it.

• 1:52:23Speaker 01

  I really can't wait to, I want to 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? It's part, how do you catch the car?

• 1:52:37Speaker 01

  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? 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?

• 1:52:52Tim Ferriss?

  Yeah.

• 1:52:53Speaker 01

  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? Is this actually making me happy? What now? And that's where like Buddhism and a lot of 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, those two events. And it's actually been a gift in a way, because now I just look at the world differently.

• 1:53:20Tim Ferriss?

  Puts things in perspective.

• 1:53:22Speaker 01

  Yeah, I mean, it does really. Yeah.

• 1:53:24Tim Ferriss?

  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 can't really rationalize the need to make more, which by the way, I mean, not to plug my own, I haven't done this, I haven't mentioned the four hour work week in a long time, but if you actually read some of the basics, the fundamentals

• 1:54:03Tim Ferriss?

  in that book, it outlines just how much self deception goes into believing that you need 20, 30, 50, a hundred million dollars. It's mostly unjustifiable. And when 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.

• 1:54:28Speaker 01

  Yeah.

• 1:54:28Tim Ferriss?

  That is a terrifying moment. And oh my God, do people, and I'll include myself in this group of people, begin to panic because you're like, wait a second, if that didn't fix these things, what in the fuck am I supposed to do? And it can be, you know, I don't want to make it a complete swan song. I mean, look, it's, it's better to, all things being equal, to have the money than to not have the money. However, the prevalence of depression in quote unquote, successful people that has increased rather than decreased after they catch the car

• 1:55:09Tim Ferriss?

  is worth studying. I think it tells us a lot about the human condition, even if you never end up catching the car.

• 1:55:16Speaker 01

  Yeah. And this is where doing the work internally, and I really respect the fact that you've used some of the. The resources you've gathered to do what the work you're doing in psychedelics, you know, I don't, I've never publicly talked about the psychedelic work or psychedelics period because I, you know, as a person who sometimes people follow what I do, you know, with a fanbase, like 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 you'd want to talk to a doctor and a therapist and do these things in a very considered fashion, but the fact that you're looking at psilocybin and other people are looking at ayahuasca or ketamine or whatever, I think the research and the suffering that's

• 1:55:59Speaker 01

  happening, a lot of it is because people have not done enough of the work to look inside

• 1:56:03Tim Ferriss?

  Yeah.

• 1:56:04Speaker 01

  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 going to 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. I don't know if you saw Colorado, I think, passed

• 1:56:23Tim Ferriss?

  I did.

• 1:56:24Speaker 01

  122 yesterday.

• 1:56:25Tim Ferriss?

  Yeah, it's big news. Very big news.

• 1:56:27Speaker 01

  It's big news. Colorado is going to 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. It's having a profound impact and people are out there and they're suffering. I really, really encourage them to go to therapy and to, you know, maybe even research this stuff because again, you give these disclaimers all the time on this podcast, but there is help out there 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.

• 1:57:08Tim Ferriss?

  Yeah.

• 1:57:09Speaker 01

  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 want to face the pain or suffering that is driving that performance, the fuel, you know, like a lot of times those hot coals that are burning, that's a lot of pain and suffering. It fuels an engine, a mighty engine. But 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.

• 1:57:35Tim Ferriss?

  Yeah, agreed. And I'll make just a couple of recommendations for folks. One, 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, I did do a podcast that people can find at tim.blog/trauma, which is a conversation between myself and Debbie Millman, who suffered from horrible childhood abuse. And we took very different paths, but found solace, found support in very, very different ways. And there are a lot of resources associated with

• 1:58:16Tim Ferriss?

  the blog post in the show notes that people 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 believed through phase three and psilocybin for treatment resistant depression, et cetera. If you go to saisei foundation.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, saisei foundation.org. There's a projects page where you can see the various universities and a lot of the researchers.

• 1:58:53Speaker 01

  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 go to see where the progress has been, because people are not aware of how much people, I think it's next year that MDMA will be available in therapy in some psychiatric settings, right? If I'm understanding the.

• 1:59:14Tim Ferriss?

  Yeah, I'd have to check the latest and greatest. It's certainly last time I checked in, it would be as potentially as soon as the end of, say, 2023 or early 2024. I'll have to check. There's so much in flux because there's not only the federal.

• 1:59:29Tim Ferriss?

  Landscape and potential reclassification, which you can do through demonstrating medical need, because Schedule I is supposed to be, and I'm painting with a very simplistic brush here, but Schedule I compounds are supposed to be drugs of, with a high potential for abuse, that have no known medical application. And rather than fighting the political fight, which you do have to fight at some point, you can demonstrate medical application through good science and clinical trials, which has been the area where I've predominantly focused. But then you have Colorado, you have Oregon as well, and these parallel systems, or initiatives to create parallel systems

• 2:00:12Tim Ferriss?

  on a state basis, a statewide basis, that will be very interesting experiments. And they could go a lot of different ways. I mean, it could all go well. There will probably be, as happens when therapies scale, various issues and problems and scandals and so on. I expect that. Humans are humans, so they're going to find a way to screw it up one way or the other. But net-net, the hope, and I do think there's some, a lot of good that has come of, say, the decriminalization nature initiatives, although I disagree with some of their stances. It's a very exciting time of flux at the moment. And as you put it, there is help out there, and there are resources.

• 2:00:52Speaker 01

  If you think about what we saw happen with cannabis in this country, and the legalization of it, like, life went on. But these drugs are really going to help people, I think, especially with the complex PTSD, especially with anxiety.

• 2:01:03Tim Ferriss?

  Absolutely.

• 2:01:04Speaker 01

  It's just great when combined with a proper therapist.

• 2:01:07Tim Ferriss?

  Yeah, they're very powerful. As a friend of mine, I don't think he said it publicly, so I'll keep it anonymous, but a very senior scientist, he said, "When you're working with psychedelic compounds, you are working with nuclear power." So you just need to be very, you need to have the right therapeutic context around it, but they're very, very, very powerful. J. Cal?

• 2:01:30Speaker 01

  Yeah.

• 2:01:30Tim Ferriss?

  Yeah, yeah, we're coming up on-

• 2:01:31Speaker 01

  I was like, oh, wow, just a quick 75 minutes, 90 minutes. I looked down, two hours.

• 2:01:35Tim Ferriss?

  Two hours.

• 2:01:36Speaker 01

  We are two hours.

• 2:01:37Tim Ferriss?

  Two hours plus. Is there anything that you would put, just as winding this to a close, anything that you would put on a billboard, metaphorically speaking? Like a 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?

• 2:01:59Speaker 01

  There's part of me that wants to tell people to take chances and that they can do it. Like to give it a shot, like to just give it a shot, right? Like it might just work out. Like, what if it works out? Give it a shot. What if it, what if it actually works out? And then there's another part of me, that's my head speaking. And then my heart is just be kind to each other, especially in the face of when people are unkind. I've just noticed that people, and this is coming from me, like I'm a brawler. I mean, I'm known for arguing with people who are brawling. 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

• 2:02:42Speaker 01

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

• 2:03:27Speaker 01

  Have great friends, build cool shit.

• 2:03:29Tim Ferriss?

  Yeah.

• 2:03:30Speaker 01

  I put a comma in there. I don't know how much, I have two sentences.

• 2:03:32Tim Ferriss?

  And you know, and you know, just building off something you just said, you can have disagreements with good friends. And I would go so far as to say, if you're not having disagreements or if you don't disagree on anything, someone's not telling the truth. Because we're all different. And if you're spending time with people who are thinking for themselves, you're almost certainly going to have things you'll disagree about. And that's part of the relationship that is an asset to the relationship. But that also means you have to learn how to. Manage conflict and resolve conflict and do repair also and do repair.

• 2:04:08Speaker 01

  Yeah, repair.

• 2:04:10Tim Ferriss?

  Yeah.

• 2:04:10Speaker 01

  Wow, that's, that's a whole nother podcast.

• 2:04:13Tim Ferriss?

  That's a whole other podcast. It's a whole other podcast.

• 2:04:15Speaker 01

  Just promise us, Tim, that you're not going to stop. I, you know, I get worried a little bit of that you're going to stop doing this podcast. Like, you can take a break.

• 2:04:23Tim Ferriss?

  Yeah.

• 2:04:23Speaker 01

  But don't ever stop. Like, I mean, you're 45. If you do that, can you imagine if you do this for another 20 years? Like, how great this archive of Tim Ferriss podcasts is going to be.

• 2:04:32Tim Ferriss?

  Yeah, yeah, you know, I.

• 2:04:34Speaker 01

  Think about the legacy.

• 2:04:36Tim Ferriss?

  Oh, I can't. It's hard for me to see stopping. I've thought about taking a break after a billion downloads, which should happen in the next few months, actually. And as much as I fantasize about, like, burning it all down and going to live in a hut in the mountains and growing out a beard and, like, smoking a corn cob pipe and reading books.

• 2:04:51Speaker 01

  Yeah.

• 2:04:51Tim Ferriss?

  As much as I fantasize about that and doing cold plunges in a river and running with my dog, there's a lot to the fantasy. But I can't imagine, as you mentioned earlier, we've had so many private conversations, and I think both of us have come away thinking, fuck, why didn't we record that? That would have actually made a fantastic conversation to share.

• 2:05:11Speaker 01

  Great app. Would have been a great app. It's the point of a podcaster.

• 2:05:14Tim Ferriss?

  I'm gonna, I'm going to be seeking out incredible, fascinating people to have conversations with, whether I'm doing the podcast or not. So I might as well record them.

• 2:05:25Speaker 01

  It's just amazing the impact it's had on Shoshada. I can't tell you how many people in just, people don't know I know you. And, or that were friends even, and like, and so then I'm at a dinner party, oh, did you hear this, you know, this podcast by this guy with this thing? And I, and it's like, all the time, it's, you're really in pop culture in a way that's just really impressive to me. It's actually, you know what? I guess I'm going through it now with All In to a lesser extent. Like, it really is a weird thing. Something about being in people's ears makes it incredibly intimate. I think the AirPods.

• 2:05:56Tim Ferriss?

  Yeah, it's very intimate.

• 2:05:57Speaker 01

  The AirPods, I think, AirPods specifically, like, these little things that can, you can fall asleep in your ears, you have them in your ears all the time.

• 2:06:05Tim Ferriss?

  Yeah.

• 2:06:05Speaker 01

  And this, the, the act of listening to somebody's voice so often, so consistently, has created some new phenomenon in the world. And we call it podcasting, but it's really like this, like. Lifelong friendship you have with a personality you've never met. It's really trippy.

• 2:06:21Tim Ferriss?

  It is trippy. It's super trippy.

• 2:06:23Speaker 01

  Thanks for having me on. I can't wait to see you.

• 2:06:25Tim Ferriss?

  Can't wait to see you too, man. So people can find you, Calacanis. Oh, God. Oh, God. That's a whole separate episode, too.

• 2:06:34Tim Ferriss?

  Yeah, that was definitely.

• 2:06:35Speaker 01

  Play for charity. We'll play for your psychedelic charity. That'll be funny.

• 2:06:39Tim Ferriss?

  All right.

• 2:06:39Speaker 01

  Play for the charity.

• 2:06:40Tim Ferriss?

  Perfect.

• 2:06:40Speaker 01

  I'm just Jason on Twitter. Go to Twitter and Jason on Twitter.

• 2:06:44Tim Ferriss?

  And anything else you'd like to mention before we wrap up? Closing comments, complaints, requests of the audience?

• 2:06:52Speaker 01

  No, no, I just, as I randomly tweeted like, I don't know, six months ago, I just had this revelation, like, because I listened to like three of your podcasts in one week and I was kind of catching up and I just like, you're a fucking national treasure. It's just good to know you.

• 2:07:03Tim Ferriss?

  Thanks, man. I really appreciate that.

• 2:07:05Speaker 01

  Congratulations on like, just, you know, like, it wasn't always great.

• 2:07:10Tim Ferriss?

  Yeah, that's true.

• 2:07:11Speaker 01

  It was like rough in the beginning and now it's just fucking brilliant. So just congratulations, like from one person who's been grinding it for a while. Like, it's just great to see you at the top of your game. I told you this in a private conversation. It was just like, I listened to your podcast. I'm like, wow, he's on the top of his game. It's like watching, like Michael Jordan or something to play basketball. It's beautiful to watch, like, and you get the best guests and they just, now when you have great guests on, they're enamored with you. And it used to be, you're kind of like, yeah, I'm Tim Ferriss is kind of what I'm doing. They come on and they just want to talk about you. Whoa, this is tipped over, hasn't it? Famous person is talking about your podcast, but you're trying to interview them. Whoa. Interesting to be Tim Ferriss. Anyway, we'll see you all next time. Bye bye.

• 2:07:57Speaker 01

  We've got to end this podcast at some point. We tried to end it five times.

• 2:08:01Tim Ferriss?

  I know. We tried to end it five times.

• 2:08:03Speaker 01

  It's because we miss each other.

• 2:08:04Tim Ferriss?

  The tearful goodbyes. And so I will say this, Jason, thank you. It's lovely to see you. I am studying what you're doing. So it's, it gives me great joy to have you on and you've inspired me to think about maybe trying my hand at an experimental format with moderating a few folks. So I'll give it a go. And this has been a blast. I've learned so much and heard so much. I never thought that I would, never would have expected to hear. So I'm so happy we made it happen. And to everybody listening, as always, we will have links to everything we discussed in the show notes at tim.blog/podcast. And until next time, be just a little bit kinder than you think necessary to other people

• 2:08:45Tim Ferriss?

  and to yourself. And squeeze the shit out of that box of oranges because we're all gonna end up-

• 2:08:51Speaker 01

  Last drop, folks.

• 2:08:51Tim Ferriss?

  We're all gonna end up on the roof, as in Blade Runner. We're not gonna last forever, so make those moments count. Thank you, Jason.

• 2:08:59Speaker 01

  I love you, brother.

• 2:09:00Tim Ferriss?

  Love you too.

• 2:09:02Tim Ferriss?

  Hey, guys. This is Tim again. Just a few more things before you take off. Number one, this is Five Bullet Friday. Do you want to get a short email from me? Would you enjoy getting a short email from me every Friday that provides a little morsel of fun before the weekend? And Five Bullet Friday is a very short email where I share the coolest things I've found or that I've been pondering over the week. That could include favorite new albums that I've discovered. It could include gizmos and gadgets and all sorts of weird shit that I've somehow dug up in the, the world of the esoteric, as I do. It could include favorite articles that I have read and that I've shared with my close

• 2:09:42Tim Ferriss?

  friends, for instance. And it's very short. It's just a little tiny bite of goodness before you head off for the weekend. So if you want to receive that, check it out. Just go to fourhourworkweek.com. That's fourhourworkweek.com, all spelled out, and just drop in your email and you will get the very next one. And if you sign up, I hope you enjoy it. This episode is brought to you by Eight Sleep. My God, am I in love with Eight Sleep. Good sleep is the ultimate game changer. More than 30% of Americans struggle asleep, and I'm a member of that sad group. Temperature is one of the main causes of poor sleep and heat has- Always been my nemesis. I've suffered for decades tossing and turning, throwing blankets off, putting them back on and repeating ad nauseam.

• 2:10:25Tim Ferriss?

  But now I am falling asleep in record time, faster than ever. Why? Because I'm using a simple device called the Pod Pro Cover by Eight Sleep. It's the easiest and fastest way to sleep at the perfect temperature. It pairs dynamic cooling and heating with biometric tracking to offer the most advanced, but most user-friendly solution on the market. I polled all of you guys on social media about the best tools for sleep, enhancing sleep, and Eight Sleep was by far and away the crowd favorite. And people were just raving fans of this. So I used it and here we are. Add the Pod Pro Cover to your current mattress and start sleeping as cool as 55 degrees Fahrenheit or as hot as 110 degrees Fahrenheit.

• 2:11:10Tim Ferriss?

  It also splits your bed in half so your partner can choose a totally different temperature. My girlfriend runs hot all the time. She doesn't need cooling. She loves the heat and we can have our own bespoke temperatures on either side, which is exactly what we're doing. Now for me and for many people, the result, Eight Sleep users fall asleep up to 32% faster, reduce sleep interruptions by up to 40% and get more restful sleep overall. I can personally attest to this because I track it in all sorts of ways. It's the total solution for enhanced recovery so you can take on the next day feeling refreshed. And good news, Eight Sleep has launched the next generation of the Pod. The new Pod 3 enables more accurate sleep and health tracking with twice the number of sensors.

• 2:11:53Tim Ferriss?

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• 2:12:39Tim Ferriss?

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• 2:13:23Tim Ferriss?

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• 2:14:05Tim Ferriss?

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