The Tim Ferriss Show - #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

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Starting point is 00:05:01 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 Kalakanis. Kalakanis, 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

Starting point is 00:05:35 at Jason, because he was an early bird on the Twitter platform. Jason, nice to see you, man. 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 it's the first time 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 have you've had a lot of investors on i have and so i've somebody's like how come you haven't been on tim versus pockets i podcast? I'm like, he's got so many investors on him. What can I add, right?

Starting point is 00:06:06 I'm sure at some point. There's a lot. 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, Sokka. And it was like, hey, this is a four-hour work week guy. And I was like, do you know how hard you're making my life? All these founders, I mean, now they think I work four hours. I I was like, do you know how hard you're making my life? All these founders, I mean, now they think I work four hours. I'm starting breaking your chops.

Starting point is 00:06:33 It's part of the charm. Yeah, it's part of the charm. Yeah. Good to see you. It is good to see you. 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 tactic that you shared because it's so smart well you load a quick time thing and you're like hey can you start a quick time people go oh yeah my quick time's running but then one out of three times at the end of the show we're like okay can

Starting point is 00:07:14 you upload the quick time like oh i didn't hit the record button so instead of asking can you you know record a quick time i say how many seconds is your quick time 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 are obsessed with, probably sort of our kinship. A tool Gawande.

Starting point is 00:07:33 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,

Starting point is 00:07:52 I don't need a checklist. And then everybody dies. 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 yeah because people had more discipline and you know it's like oh i know you guys didn't need this checklist but we have bacterial line infections down by 39 this year oh go look at that yeah yeah well people would take a scalpel that was dirty and they made this little device right these little life hacks

Starting point is 00:08:23 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 well anyway it works both ways they would put a little um 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. Tent off, no bueno. No bueno.

Starting point is 00:08:57 Now, you can't believe everything you read on the internet, so please correct me if I'm getting any of this wrong. But 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 tax authorities tax authorities yeah my dad got a little behind on the taxes. Yeah, the taxes. They sneak up on you. 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.

Starting point is 00:09:39 This is in the 70s and 80s. 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 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 one of the great traumas of my life. And it's one of the things I really appreciate and respect about you is you shared your trauma on this podcast. It's like a gift to the world. You know, that's a pretty scary thing when you're 17 years old

Starting point is 00:10:09 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,

Starting point is 00:10:24 when the Empire Strikes Back and Han Solo comes over to Chewbacca. It's like, just take care of the princess. I'll be back. It was really intense, really intense. Yeah, I bet that's crazy. And that really is like my life just got crazier and crazier after that. So I forged such a crazy childhood that was so violent and crazy and just Brooklyn when it

Starting point is 00:10:47 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. 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 hell's 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, I would have to go serve espresso to the bookie or the dealer or the head of the Hell's Angels. It was bonkers.

Starting point is 00:11:33 And it just made me really good at dealing with people, I think. Yeah, I would imagine you developed a lot of situational awareness. 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 been a pretty surreal life the whole way, I have to say. 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

Starting point is 00:12:06 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? So having a dad who was an entrepreneur, it kind of puts it in you. And I had one or two jobs when I was in college. I went to college at night, so I would fix laser printers and build networks. This is before the internet existed.

Starting point is 00:12:43 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.

Starting point is 00:12:53 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 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. And I just looked at the people who were in the pictures,

Starting point is 00:13:17 Tim, and I was like, why are they on the cover of the magazine? 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? It was really weird being dropped on an alien planet because Brooklyn was so different than Manhattan at the time.

Starting point is 00:13:53 Yeah, for sure. Brooklyn was a bunch of blue-collar people. Manhattan were rich people and powerful people. And so something just clicked in my brain. 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.

Starting point is 00:14:13 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?

Starting point is 00:14:24 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. I'm talking to this guy and I said, what are you doing? He says, oh, I work at a magazine. Let me pause for a second. Barney's sounds fancy. How did you get invited to the party? You know what?

Starting point is 00:14:39 I just was hanging out in the downtown scene where a company called Voyager was making CD-ROMs, Blender 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 copuser 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

Starting point is 00:15:13 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 service 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 and 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 said 10 people in a room designing a web page with 10 logos on it that was the entirety of the website was one page and then like a 12 page legal

Starting point is 00:15:57 disclaimer so this is a very interesting like moment in time and uh i said what magazine he said paper magazine i said you work at paper magazine and he said i created 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 hershkowitz 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 balthazar 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

Starting point is 00:16:35 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 comment a sentence and so this christine mulhoeky was my editor. She was like 20-something years old. I was 20-something years old. I started writing for Paper Magazine. And then Hershkovitz was like, he was really getting into the internet. I remained friends with him to this day, 30 years later.

Starting point is 00:16:56 And he would just ask me to come by the office. I hang out. I'm hanging out at Paper Magazine. He's like, hey, you want to go to a concert tonight? Yeah, sure. He says, yeah, we're going to go to the Roxy. This new band, Chemical Brothers, is going to be playing. And Orb's going to be opening for them.

Starting point is 00:17:10 And then we're in the green room, or the VIP room, waiting for this 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 that like Norway or Sweden? She's like, no, it's 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, it's like over here. And she's talking really low.

Starting point is 00:17:25 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, I just, I'm a singer. I said, oh, I'm Jason. And she goes, I'm Bjork.

Starting point is 00:17:33 You know, this is New York in the 90s. I mean, it was cool as F. Like it was the zeitgeist. It was crazy. And 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 never heard you censor your cursing

Starting point is 00:17:50 before that was very delicate it's a family show i think you can curse it's okay you don't don't tell a kid from brooklyn to start cursing your poor editors are gonna be he just created three hours of anywhere search for place we have 47 fucks in the first 30 minutes. 47 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

Starting point is 00:18:22 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 he'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 oh yeah and they had a zine section and zines were short for magazines z-i-n-e for people who are under the age of 40 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

Starting point is 00:18:57 together and then you would photocopy so 2600 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 400 words. I can write 40,000 words. I can write 4,000 words, whatever.

Starting point is 00:19:21 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. I could do like a Silicon Alley reporter. And it just be me reporting on what's happening here. Cause this is cool. Like there's like, now it's like 200 people doing stuff. And so I just started a photocopy called silicon i reporter and i went up to the village printing shop on 43rd street and sixth avenue and every 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 it's still there but a couple years ago it's still there and it was 24 hours and i brought it to the guy there's a thing called tabloid paper there's you there, but a couple years ago, it was still there. And it was 24 hours. And I brought it to the guy.

Starting point is 00:20:06 There's a thing called tabloid paper. There's 8 1⁄2 by 11 plus 8 1⁄2 by 11 equals whatever it is, like the 17 by whatever. You could take that paper, fold it, and put a staple in the middle, and it would look like a newsletter. And so I said, okay, that's the format. I got PageMaker. I started laying it out. I took pictures. I wrote a couple articles.

Starting point is 00:20:23 And I went there, and I printed it. And he said, yeah, it's going to be like $ 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 you make me a thousand copies 800 bucks right and i'm just gonna start handing them out like david herschowitz did and i go and he hands me a bill for 1750 and i said wait you said 10 cents it's eight pages I 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 Alley Reporter here so I start talking to the guy now I'm gonna I'm haggling with him and he's just the overnight manager and he said listen I don't have the money for this like I just I my credit card's maxed out can you do me a favor like maybe

Starting point is 00:21:03 someday I could 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 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 to roseland where there was a internet party going on or like roseland's a venue like a music venue and then some electronic music president played and then

Starting point is 00:21:55 like a bunch of internet multimedia people were going to 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 my backpack and in my hands to the party. I get to the party at like one 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 look at the party, which was popping off. And every single person has the magazine open the zine open the photocopy and

Starting point is 00:22:26 is reading it with two or three people around them the entire party stopped so what did that feel like like what happened to you and that when you saw that ah okay i got the power you got the power 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 but like literally i mean listen i you know i consider it a privilege to be on here and you've shared a lot like and 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

Starting point is 00:23:09 dead in their tracks. The adrenaline and the confidence, it felt like all of a sudden Superman figures out when he reaches into the fire to get something he dropped, and it's like, the fire doesn't burn me? Whoa, I 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 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 alley reporter 10 issues a year, $100, or no, $90. And I had seen Esther Dyson charged $1,000 for her newsletter. So I was like, well, she's Esther Dyson. So if I charge 10%, maybe that's the same thing. Because Esther Dyson was this famous, you know, angel investor. And I just, when I went out, if I didn't have the magazine on

Starting point is 00:23:59 me, I had the cards, 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 $1,800. Mailbox money. Every day, $4,000, $6,000. And all of a sudden, there was like 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 Hershovitz 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.

Starting point is 00:24:44 And it was basically like this all of a sudden becomes the 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 Hershkovitz at a party. I get this guy to print out the things. I go to that party and drop them off. And all of a sudden I'm important. 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 foreign scum thing so that's a problem this is gonna now i this is gonna stick everything will be like well i guess's like a box of chocolates, too.

Starting point is 00:25:26 He just dumped me the Forrest Gump. I mean, the internet industry, it's going to stick forever. I'll take it. I'll take it. Forrest Gump had a great life. Yeah, yeah, he did. And that was the start of a great life for a very simple man. So I'm so glad we're talking about the early days because, of course, I had no a lot of but you had the same thing nobody knew who you were you're some guy and you all of a sudden this four

Starting point is 00:25:50 hour work week goes from yeah like you got paid nothing for that book nothing and then all of a sudden wasn't it the same exact experience it was similar it was similar yeah i 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 said, Heather, don't fuck with me.

Starting point is 00:26:24 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 to myself, oh, wow, things are about to change. Things are about to change. And all of a sudden, let's call it within the next few weeks, it kept growing. And then it

Starting point is 00:26:46 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- Mind-blowing. Bewildering. Yeah, very bewildering. 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.

Starting point is 00:27:10 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, you're a 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,

Starting point is 00:27:27 Say what? That's what I made last year. Come again. $3,000? No, no, at a zero, $30,000. And you're just like, that makes no sense. And they're like, well, it's going to be two hours of your time. We don't want to put you out, Mr. Farris.

Starting point is 00:27:40 And you're like, can I come back? Can I do it tomorrow too? It is a mind-blowing experience. I literally just had one of these come in today, some corporate gig. 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 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

Starting point is 00:28:07 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 in a year yeah it's weird and you also had this kind of like same situation yeah so it really does screw with your head and it's very hard to stay grounded or figure out what's actually happening, right? Yeah. 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

Starting point is 00:28:54 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. 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 slash Tim. That's linkedin.com slash Tim to post your job for free. Terms and conditions apply. So let's talk about another holy shit moment.

Starting point is 00:29:36 And this is January of 99. You're offered 20 million, I believe. True story. And the commerce business. So, and I'm reading here, this is from Fast Company, and it talks about your interaction with- Alan Meckler. This was with, I think, Douglas Rushkoff. Oh, Doug Rushkoff, yeah, my friend in New York. That was another guy who taught me so much.

Starting point is 00:30:03 I love Doug. 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. 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 $6, $7, $8 million a year. I had done an event or two.

Starting point is 00:30:30 That started making $2 or $3 million. So now I've got an $11 million company. I built up my credit cards. And I was making, just a couple years earlier, minimum wage to work in the computer room at Fordham, which was $3.50 an hour. And then I was fixing laser printers for $9 an hour. And then I got a job at Amnesty International doing their internal network for $12 an hour.

Starting point is 00:30:51 So all of this happens in a very short period of time. And again, for a poor kid from Brooklyn, I'm just trying to navigate it. And this guy, Alan Meckler, had internet.com. He took it public. It became worth a billion dollars. And he offered me $20 million for Silicon Valley Reporter. But it was my identity.

Starting point is 00:31:06 And it was making 10 million and i was like i don't want to give up my identity but i thought about it well if i can make if i can clear a million or two million dollars 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 $500,000 or $600,000 in this employment agreement,

Starting point is 00:31:36 and they paid off all the bills because I then had, like my dad, I was in arrears when the magazine collapsed. If you've got a magazine about the internet and the internet collapses, literally, 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

Starting point is 00:31:56 then i show up for work at dow jones and they say hey can we take you for a walk it's like manager manager guy and i'm like sure walk okay sure we'll go for a walk we'll go 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 the 20 you know had like 20 people left and they had reassigned him to this other venture capital thing they were doing i said you don't want me chasing calacanis the silicon alley reporter to work here they said no i said i just signed a contract with you for 600 you know five or six hundred thousand dollars they said yeah and he pulls out an envelope and he hands me a

Starting point is 00:32:39 check for five hundred thousand dollars he says we're paying out your contract 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 five hundred thousand dollar check which is a 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 yeah they don't want me yeah 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

Starting point is 00:33:23 knicks games hanging out with alan houston you, the number one star on the Knicks at the time. I mean, I was living it. The peak. 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 just took the sword out.

Starting point is 00:33:52 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 got to build something. I got to build something. The next day.

Starting point is 00:34:16 The next day, I was like, literally got an office share in my friend's office. I said, can I get a desk? You know, it was like that blank sheet of paper in 2002, 2003. I got to figure something out. What's next? And I just started making designs on whiteboards. 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?

Starting point is 00:34:46 I started calling people out. What are you working on? 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

Starting point is 00:34:59 who are building stuff for the web because the web had gotten advanced now in the second decade. And it could do like, the web pages 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.

Starting point is 00:35:25 It's another group that was, you know, trying to do like photo sharing and follow your friends. And I'm just like, huh. And then I had somebody who had worked for me named Rafid Ali. 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? 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 going to happen after the dot-com bust because everybody quit and everybody went and got jobs at big companies.

Starting point is 00:36:05 So you're trying to get a read of the playing field to see where the puck might be going next. Exactly. Is there anything interesting in the world? I'm mixing my sports metaphors, but you get the idea. I'm talking about field hockey, everybody. Yeah. Let's just say, like, Tim Ferriss, when he learns a sport, it's wild to watch. Watching Tim Ferriss learn a sport it's hilarious because i thought

Starting point is 00:36:26 about it do a layup it is it is dribble a basketball it was hilarious that's another story it is funny and and also if you learn a sport with jay cal you are going to have to listen to so much shit he will torture you at every opportunity. Oh, God. Yeah. Watching Tim Ferriss go from being a perfect fencer or perfect yoga in negative 100 degree, and then he tries to dribble a basketball. It's literally like looking like a drunk person with a blindfold on. Oh, yeah. But to your credit- True story.

Starting point is 00:37:00 I watched you learn how to do a layup, and 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' gift. He knows how to ask the right questions, and I'm watching you process. It's actually impressive. But anyway, it was like one of those moments where you're like, what's next in the world? I was just trying to figure out what was next and so i was just because also so many people were out of work that if you couldn't get a job you kind of just started tinkering which is kind of how multimedia started so i was like

Starting point is 00:37:35 i've seen this before technology keeps going people are starting to tinker and wi-fi had come out at that time i was very fascinated about wi-fi and i was thinking about wi-fi routers and putting wi-Fi in places. And maybe you could have internet and 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.

Starting point is 00:37:58 And I was going to get 100 New Yorkers and give them Mercury Club number 1, 2, 3, 4, 5, all the way to 100. I was going to 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 traffic. And I had seen Cosmo had started experimenting with Vespas. i said i'm going to create a service where you pay a hundred dollars a month for rich people and you get four hours of deliveries 25 bucks an hour this is when you know minimum wage was

Starting point is 00:38:34 six or seven bucks but this is only for rich people and if you needed a bottle of wine or 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-Batress, 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,

Starting point is 00:39:00 or zines. Starting 2005 blog. 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,

Starting point is 00:39:10 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

Starting point is 00:39:22 get to play with it, right? So I never really actually thought about it, but it is true. and so i was looking at the 800 number so again 1-800 mercury i said trying to get a mercury club number and my idea was the reason because i remember i was 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 he 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 i was like why didn't you he's like the vcs told me not to 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

Starting point is 00:39:56 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 the bike messengers used to hang out aside where my loft was because it was business commercial loft at the star at 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 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.

Starting point is 00:40:28 And they got to just bomb these bikes all over Manhattan. And they got exercise. They were fit. They were smoking weed, listening to music. It was like the coolest gig ever. I was like, these guys, they figured out life. Yeah, yeah. You get to ride your bike all day, smoke dope, listen to cool music, joke with your friends,

Starting point is 00:40:44 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 just a crazy revelation i had so i was like yeah i'm gonna do mercury club and i built the whole business model uh for mercury club how did you land on the name well mercury like the god with the wings on the feet and i was just like it came to i was greek i always like the greek god so i was just like yeah i kind of started thinking about fast. And I just thought, well, this would be incredible. Can you imagine you're at your Charlie Rose at a party or David Hershkowitz from Paper, and you're just like,

Starting point is 00:41:12 should we get cigarettes? Yeah. And you just pick out your, because mobile phones had come out at that time. So imagine taking out your StarTAC, and I had seen a StarTAC phone, those little flip phones. So imagine you take that out, and you dial in an 800 number, and you say, yeah, I need two packs of Marlboro Lights,

Starting point is 00:41:23 and bring me a copy of Vanity Fair or Esquire magazine because I'm at a party and 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. Greek. Your name is Greek.

Starting point is 00:41:39 What does your last name mean? Kalikanis. Kalikanis 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. Very nice. But it's with Ks. So when my grandfather went through Ellis Island, God rest his soul, they were like, Calycanis, here's your banana. Keep moving. And he was like, no, it's Ks. And they were just like, fuck you, Calycanis. Here's your banana. No, they used to give bananas at Ellis Island, I understand. What? That's real? Yeah, it just like fuck you calicanas here's your banana no they used to give bananas at ellis island i understand yeah it was like some weird thing where they just would

Starting point is 00:42:09 give everybody who comes in like a banana because 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 just like here have a banana today i'm learning keep it moving 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 calicanis my great grandfather 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 he has gone through it like 12 times.

Starting point is 00:42:46 It was quite a weird. That's wild. Yeah, 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.

Starting point is 00:42:56 It was Americans. It was human cargo. It was pretty crazy, right? That is wild. So anyway, then I had watched the blog stuff happen. And two people who had worked for me, Shani Jardin 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.

Starting point is 00:43:15 I asked Latham, can I hire her? Because she's awesome and rad. And I hired Shani to come work with me at Silicon Air. She would produce my events. And then when everything shut down, she started working on this like boing boing thing. 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 rafa ali was doing this kid who had worked for me rafa ali was doing a blog on the site called pay content.org and uh 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 call him into my office i'm like you got something to tell me kid

Starting point is 00:43:55 he's like no i'm like you sure you don't have anything to tell me he's like is it about pay 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 hold on kid let me stop you number one nobody's paying for content the whole reason we started the internet is information wants to be free. Number two, you're not a great writer. I'm your editor. Who's your editor for paidcontent.org?

Starting point is 00:44:32 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 get back to your desk and i just like admonished rafa now i'm an investor in this company now skiffed but that accepted in me because when we shut down i had talked to shenny i talked to rafid and raf's like yeah i'm making like four

Starting point is 00:45:10 grand a month on ads i'm like i was paying you 35k you're making 4k now you're making 48 you're making 13 000 more than when you work 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 i do like two or three hours i was 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 ares are dope. Blogs, even though they have spelling errors in them, come out faster than magazines and newspaper articles. They're

Starting point is 00:45:51 faster and faster is always better. It's faster. I said, and for the right writer, it's spicy. Like, oh, Shani'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. I didn't understand what they meant, but literally it was at like TED and they were at like one of Brockman's dinners and they were

Starting point is 00:46:32 talking about faster, better, cheaper, whatever, pick two. And I didn't understand what they were talking about, but 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 who had worked with me on the magazines, and I said, let's go to the Knicks game. I went to the Knicks 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.

Starting point is 00:46:56 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 did weblogs for business? Nobody's ever done a business topic. So we'll do weblogs. And he goes, oh yeah, we should call it weblogs Inc. And then he got the domain name. And then we started building them. And we did a weblog on Wi-Fi.

Starting point is 00:47:15 We did a weblog on Apple. And then we started building all these ones. And 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. That's just insane. That's just insane.

Starting point is 00:47:51 The berserker, insane J-Cal, I'm going to prove it to the world, proved it. And then I was like, yeah. I just looked at the sword. I 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 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 yeah it was my once you're lucky twice you're

Starting point is 00:48:15 good moment because then everybody who had watched me fail and kind of danced on my grave it's like an eye reporter was like oh god oh jake again. The cat came back the very next day. We thought he wasn't gone, but he wouldn't stay away. There's a lot of people who are just like, oh, he's going to be insufferable after this. They weren't wrong. They weren't wrong. They weren't wrong. So just a couple of maybe boring housekeeping questions.

Starting point is 00:48:41 I'm thinking of the timing of building these weblogs. Yeah. How did you find the writers to do this? A great thing for people to understand right now in this moment of 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 don't know when you're going to- Oh, that's okay. It'll come out reasonably soon. But people, as a snapshot in time, also, I mean, crypto is having a complete implosion.

Starting point is 00:49:06 FTX is going through the meat grinder. People are probably going to go to jail. Yeah, jail, $32 billion eviscerated. I actually wanted to talk to you about people who commit fraud and lie because I was interested in your perspective on it. Yeah. Because I just can't imagine it

Starting point is 00:49:19 because the system is so easy to win and the system is set up for entrepreneurs to win in this country. Why on earth would you cheat if it's so easy to just have a win by just working hard anyway putting that aside but i interrupted you because you were you were tying the weblogs and all 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 live journal blogs. And we'd find somebody who had written a blog about Apple, Sean Bonner.

Starting point is 00:49:51 And I said to Sean. Sean Bonner. Yeah. And I said, hey, Sean, I'm doing this Weblogs Inc. thing. We're going to try to sell ads on blogs. He's like, well, that's stupid. I'm like, yeah, but I think I can figure it out because I did a magazine. He's like, all right, that's pretty smart.

Starting point is 00:50:03 I was like, I see you're writing some 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 mellenweg uh wordpress like pro vip that you like people like you and i use automatic yeah at automatic and so anyway like great collaborator of my career you know my he's kind of my uh george harrison or you know uh my paul to my uh 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

Starting point is 00:50:40 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 how many a day could you do about apple products it's like two i was like okay 260 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 two or three dollars a blog post so we just then just started hiring people and then we made a five bucks a blog post eventually 10 bucks a blog post and people thought we were stupid because minimum wage at the time was 10 bucks and people were like i wrote three blog posts this hour and you gave me 30 but i had done a spreadsheet with

Starting point is 00:51:22 brian and i, here's how many page views 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. 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

Starting point is 00:51:53 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. That'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 alvey 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

Starting point is 00:52:16 don't want to be gadget.weblogs inc so then we made the apple.weblogs inc the unofficial apple weblog twa t-u-aW, which people fell in love with. People were addicted to TWA because at that point, we were doing eight or nine blog posts a day about Apple. And Steve Jobs read it, and Johnny Ive, and everybody. And Ben and Gatia became a juggernaut. And it was just a very simple business. And at that time, $30 million was the equivalent of hundreds of millions now.

Starting point is 00:52:43 Yeah, for sure. It was a different era. 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

Starting point is 00:52:58 and you've produced a lot of events. I have only produced one event. And it was very, very, it was in Napa long ago. And it was so- I have a friend who went, she loved it. Yeah, it was a great event. It was- People still talk about this event.

Starting point is 00:53:15 Somebody brought it up last year. 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 winemaking 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.

Starting point is 00:53:42 Why do you love doing events? And what is the smart way to do it? What is the J-Cal recipe? In the Myers-Briggs, I'm going to say you're INTJ or INTP. Nailed it. INTJ. But I could see you being a perceiver. But anyway, I'm ENTJ. And so you and I vibe until such time as I absolutely exhaust you and you need to go to your room and take a deep breath. That's 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. Yeah.

Starting point is 00:54:16 Astrology for dudes. Astrology for men. Yeah. That's basically it. 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, on 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 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,

Starting point is 00:54:45 that was like an interesting 90 minutes with J-Cal. I need to go write for four hours or whatever. You need to recharge your batteries. Take a nap.

Starting point is 00:54:52 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

Starting point is 00:54:59 once you, you have to understand your format. I think the reason why you're the number one, you know, guy in podcasting is because this format works really well for you.

Starting point is 00:55:09 You take a lot of time to think about it. You do your 90 minutes, and then you've 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. Once you understand, I'm like the morning radio guy, right? And you're like the weekly 60 minutes guy. Vive la différence.

Starting point is 00:55:31 The problem with events is some people who are introverts, 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 interviews somebody and then you come back out and do a Q&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 my childhood need to be important or have power, which was based on having no power and no money. And I feel like I've kind of processed that now. I've kind of processed it, if I'm honest, like maybe 15, 20 years ago, 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

Starting point is 00:56:21 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 cinema, or perhaps even literature, 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.

Starting point is 00:57:06 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 weird moment in time that when I just start describing it to you, you and I just start laughing. It's just a great Tim and J. Cal moment that nobody else was there for.

Starting point is 00:57:24 It's just the two of us, like literally in a basketball court, hidden in the woods on a farm in Italy somewhere that we discovered. It's a really beautiful memory for me. And I think for you. Yeah, for me too. And you just then,

Starting point is 00:57:35 we'll get to the end of our lives. And just like that Nexus 6 that has this like four year lifespan and he's crying for the lost memories. Like that's all you have. 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 it was i was talking to them about it on um halloween it was just two weeks ago 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

Starting point is 00:58:04 and so just you can be proud of even if that was the only memory that happened there that was like her favorite event i was like you've been to mine she's like yeah but that was the one i like best and so just you could be proud of even if that was the only memory that happened there that was the only tear in the rain you always have that right and so for me that's what it is the 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 Hsieh passed, a lot of our friends are gone. Yeah, it's wild. Gone too soon. And now I just look at it and I'm like, how many more memories can I put into the memory bank before the tears in the rain moment? So let's talk about friendship, because there are a few things that come to mind when I think J. Cal and friendship.

Starting point is 00:58:47 I wanted to actually sidestep and just mention something that ties back to a few things you said that I was going to bring up later. 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. All right. So this is a quote from Douglas Rushkoff. Yes.

Starting point is 00:59:28 Oh, there's a good one. I put this on the back of my book. Yeah. 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

Starting point is 01:00:05 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 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 the navigating, starting a project with your close friends. 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 got to 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 going to 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

Starting point is 01:01:04 rules like if you saw two of us and one of going to go, where's your brother? Go get your brother. It doesn't matter if it's the oldest, the middle, I'm the middle or the youngest. You three have to be by each other's side all the time. Never leave one of your brothers behind. Never let anybody say anything to your brother. Always fight. It was 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 at times i might be like i don't agree with you or like that's stupid timmy Timmy, that's the ugliest layup

Starting point is 01:01:46 attempt I've ever seen. What the fuck is wrong with you? 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. There's any way you can put the ball in the box.

Starting point is 01:02:03 Your chances go up dramatically if you hit that box. You're like, okay, I got it. I 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. Everybody wants something from Tim Ferriss.

Starting point is 01:02:30 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, 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. This person does not care about your ideas, and they're busy. 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

Starting point is 01:02:59 for them because as you become more successful the, 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. Yeah, it gets a lot smaller. A lot smaller. It gets a lot smaller.

Starting point is 01:03:23 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 know, you can have like true friendship and talk about things that matter, your kids, you know, your, 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 you get, or the effort you put into the friendships you have, right? Like, and so people don't invest in it. And the people are so transactional. It's actually of weird i was at a halloween party and a lot of people were coming up to take

Starting point is 01:04:10 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 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 or an event with more than eight or ten people, I will leave the dinner every ten minutes to go into the bathroom and just close my eyes and breathe.

Starting point is 01:04:44 I will disappear. 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. Well, and now imagine it's people who,

Starting point is 01:04:57 you know, are a fan of yours or think that they can use you to achieve some goal. Right. And literally all these influencers at this party, really like their goal is to just get a picture. And I just had this like profound sadness for them. I'm like, if I was meeting me and I was an entrepreneur, like a photo is great,

Starting point is 01:05:18 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? Who cares? So anyway, it's important to be, I think, a really good, loyal friend. I have been burned in this regard where I've been more loyal to certain people and they

Starting point is 01:05:40 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's 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 a random show with Kevin. Kevin does. summers ago and you and Kevin were talking about Ozempic. He had taken Ozempic and puked.

Starting point is 01:06:26 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 series of Ozempics along with fasting that I learned about from you and Kevin and using the Zero Fasting app, which I learned about from the show. And then I obviously hear you talk about weightlifting and the impact that has. And so for the past year or so, I just did the Tim Ferriss, Kevin Rose program. I did a couple cycles of Ozempic. I did the weightlifting and I did the intermittent fasting using the zero app and yeah, I dropped 30 pounds. I said it before we started recording. I was like, you look really, really good. Well done. I still have like, like to get five or 10 more pounds ten more pounds of weight oh you know of like muscle and then be able to run a marathon again

Starting point is 01:07:08 so i get those two goals that would be pretty happy yeah you can do that you can do it you can definitely do it i'm in the window yeah so solo act suddenly decides wait a minute i want to be in a rock band but i i may not decide that actually i'm kind of pleased to do it okay i'm being honest. So tell the story. What happened was Chamath and I had become friends. And you should explain. People have no context. What is All In?

Starting point is 01:07:31 What is the premise of the podcast? All In is a podcast with four friends who are all capital allocators. In other words, like venture capitalists, investors, and business builders. 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,

Starting point is 01:08:01 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 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 he'd have like a 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 do this. And it was like a very full contact kind of dynamic, interrupt each other conversation. But it just 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

Starting point is 01:08:51 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. 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 Palihapitiya was, but he came on the podcast. In a lot of ways, like Chris Saka did, our friend, was one of the first people,

Starting point is 01:09:27 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 times, and then he keynoted a couple of events. And we just had this rapport. 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 and 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 spax public private i was like that's a really good idea sure

Starting point is 01:10:04 let's do it and 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 Saks had been doing a bunch of research on and he bought ventilators and he had masks and explain who Saks is so David Saks 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.

Starting point is 01:10:40 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 that 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. 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

Starting point is 01:11:16 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 Hoodhood and that whole AMC thing happened. And I was an investor in Robinhood. 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. Caught heat in a good way.

Starting point is 01:11:38 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, it's one thing I learned in my life. It's like the day before the Weblogs Inc sale and then the day after when I had no money

Starting point is 01:11:54 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 um it's a big failing of like human nature yeah that we have

Starting point is 01:12:15 this weird thing with the scorecard uh that we think the scorecard of dollars is like important it's not long story short all the stuff comes together and people, it seems to connect with people and it starts racing up the charts. And the last couple of weeks, I think we were 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,

Starting point is 01:12:50 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.

Starting point is 01:13:03 It's a much wider aperture of people. And 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 technology is obviously 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 got

Starting point is 01:13:46 four of the most opinionated friends who've 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 etc but objectively you know chamath has a series of fans freeberg now has the stands sax has the whole right wing so it's like a super team has come together yeah 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 so could you walk us through your favorite of those three times and how it was resolved well i wanted to do an event because you mentioned we're like events and i was like let's do this all in summit i'll do all the work and uh you guys show up i have a production team and

Starting point is 01:14:37 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 time.

Starting point is 01:15:07 I don't know if I can afford your speaking fee. 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. But there'll be an opportunity i'll interview you no there'll be some opportunity where you'll will like it'll be a fun thing for us to do and in my own defense i have been to events of yours before i've gone to i have spoken

Starting point is 01:15:36 with you at at events yes so i could make that one couldn't make that yeah okay that's true so where does the conflict come in 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. I said, what if it's bad? People paid $7,500 a ticket. I'm like, listen, people pay $7,500 a ticket for every event.

Starting point is 01:15:58 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 Gerstner over here. I love how he was anonymous up until right now. Whatever.

Starting point is 01:16:16 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, stab you in the back, stab you in the face thing, you know, like, as you got the quote from Doug. I said, listen, if you are really enjoying our time together but it was another one of these like stab you in the back stab you in the face thing you know like 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 gershner who sits in when one of us is out as like the fifth beetle i'll have him do the other 25 we got this big fight and the whole thing

Starting point is 01:16:42 is 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. Yeah. 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.

Starting point is 01:17:02 You know, you got a top 50 podcast. 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 yeah this is one i hope i was hoping you would bring up so yeah so i'm sitting here on you know arguably 25 million dollars in advertising which i would get a fourth of and they're like sax is like well i'm already rich and i got a plane and shaman'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

Starting point is 01:17:39 got ads it's just an ad people listen to the ad they drink some athletic greens athletic greens is healthy for you we're done here like who doesn't love athletic greens we're good you know like yeah sorry to give athletic use the promo code tim not jay cal oh no use tim not twist oh i love i love aj i was just texting with the ce, Chris, like 45 minutes ago. Yeah, anyway. You know, I had it this weekend. I made a really good ginger and some other juices. I know people drink it with water, but I like a little juice. And what I do is now I use half the amount of feta greens, but I do it twice a day. I kind of like to space out my feta greens. I like the ginger idea.

Starting point is 01:18:19 It's slightly different. But the ginger, when you blend that ginger, you have that spicy, mmm, yummy, yummy. But your partners were not buying the ginger when you when you blend that ginger you have that spicy yummy yummy but your partners were not buying the the ginger cocktail no so literally like i could use another seven million a year you know like this is big cash six or seven millions it's a lot literally to have it it's a lot it's a lot of money well after taxes it would be a jet yeah so no i have no jet this is when this app this podcast this this episode is going to get clipped like crazy so good guys let me have a jet you're standing between me and private aviation i'm being a little facetious right now but you know it's not exactly facetious yeah yeah so anyway i just said you know what i'm not going to try to monetize this anymore

Starting point is 01:19:04 we're not going to do live events it causes too much chaos let's just do it every week and then i am 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 jason at calacanis.com 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 i really hope the emails read exactly basically it's like oh hi j cal i'm a huge fan of all in my family office that we did this we saved the whales and we love we have big fans of the pod. Translation to 140 characters.

Starting point is 01:19:46 I'm rich. Can you make me richer? Basically. And so I kid you not, I do five webinars the last five weeks, $44 million in commitments from people I have never met. My last fund was 44 million. I have not done an in-person meeting yet.

Starting point is 01:20:00 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 million. It's not a donation. It's 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 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

Starting point is 01:20:33 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, and we have to be rooting for each other. And I said to everybody, like, if we're going to 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, Sax and I have had blowout battles over, like, Ukraine. And I'm like, listen, Putin needs to be stopped. And he's like, you know, Biden and these people are tempting a nuclear war. This is a very important debate. Yep. And it gets very heated. And, you know, people think Sachs and I hate each other. Sachs and I love each other deeply, even though he can't say it. I can say I love Sachs, and I know he loves

Starting point is 01:21:14 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, Sachs is right about a lot of things with the 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

Starting point is 01:21:44 the weapons, can you please sit down and try to work this out but it has created chaos 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 well yeah you start to have a very big responsibility exactly you nailed it i was i was that's what i was thinking like now people are calling me saying hey you got to get sacks in line and then people are calling sacks saying oh j cal hates trump he's got trumped arrangements 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 uh masks and covid and what i tell people

Starting point is 01:22:24 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. get it when we talk about anything else kovat 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 kovat specifically which was kind of ironically where this whole thing started and what caused it to start is now Politico.

Starting point is 01:23:05 I'm sorry, vanity fair and pro public. I don't know if you saw this or 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 pockets were saying,

Starting point is 01:23:17 well, maybe it's a lab leak. They were like, well, we have to take that podcast down now. So we can't have that conversation that it's a lab leak. Like, yeah,

Starting point is 01:23:26 there's two labs in the world that are studying the Wuhanuhan virus and one of them is the one with covet happened it happens to be in wuhan like there's 10 000 locations in the world like pretty easy jump to make but there's some weird thing going on right now where people expect tim ferris or joe rogan or david sacks can't have a conversation talk about a topic because their shows are popular. 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. If it's helpful, I can tell you my policy on this stuff. Please tell me. Where I say my protocol. My protocol is if I'm going to talk about something that I know is going to light people

Starting point is 01:24:10 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. Yes. It's very simple. 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.

Starting point is 01:24:33 You will get ouch my balls. Like literally like idiocracy, the TV show, ouch my balls. Like you're going to get your nuts kicked 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 interviewing people and trying to learn. And I actually think there's a little bit of responsibility on the audience's part here.

Starting point is 01:25:08 You know he's a comedian. There is. However, I'm going to push back a little bit. Okay, yeah, let's go. I 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,

Starting point is 01:25:28 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 well he said he doesn't do it he said i don't

Starting point is 01:25:50 come in prepared he 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. I mean, you're a very close friend of mine. Yeah. Look, yeah, I know you do research. I've got 20 pages of notes.

Starting point is 01:26:12 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 I think audiences have to take some responsibility. It's probably between the two things we're talking about here. It's between the two. And he might not want to do this, but 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'd see on jackass back in the day which would be like these are trained professionals this is for entertainment yes and like do your own homework actually i have an idea for joe rogan i think he

Starting point is 01:26:55 should start a second podcast it'll make tens of millions of dollars called after joe uh and it should be a group of experts vetting whatever was talked about or goofing on it just that's a great idea after joe post joe yeah 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 web page 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 that they make so much money, pay three people, $2,000 each, just spend five grand on like, this is a medical episode, vet it,

Starting point is 01:27:33 put a bunch of links in it. That would just make it so much better. Right. I think. 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. Use your words, Ferris, privately. So we've talked about your moderating. I think you are one of the best moderators I've

Starting point is 01:28:08 ever seen. And it's true. And that is absolutely, I would say that to anyone. I'm actually pretty sure I have said it publicly. You have actually, thank you for that. 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? 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

Starting point is 01:28:56 quite charming and hilarious, probably a little cutting edge for some people. But anyway, the Red Scare podcast is hilarious. And Dasha always says, oh, what's on the docket? And they have a docket. These are the people who are going to pass's on the docket? And I have a docket. Like, you know, these are the people we're 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.

Starting point is 01:29:17 So the docket is a Google doc? Yeah, a Google doc of topics. And then this is put into a private Slack channel that you guys use or something like that? Yeah, we're on Signal. And so we... Yeah, this way they all disappear within a week. Hard lessons to learn. Thank you for getting it.

Starting point is 01:29:34 So anyway, Signal. You can reach me on Signal. So now, do you use desktop client for that to make it easier to use? Or do you do it all on mobile? Signal is desktop and mobile now. Yeah, it's pretty great. And it's not owned by the Russians. I use mobile signal is desktop and mobile now yeah it's pretty great and do you use mobile the russians i use mobile and i use a desktop yeah okay great anyway

Starting point is 01:29:50 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 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,

Starting point is 01:30:15 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 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 gotta get out of this guy i gotta get him engaged

Starting point is 01:30:45 freeberg i gotta 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 sax i got a tiger 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 line going crazy you got your science nerd coming out of his shell and then with chamath it's more like an alley-oop sweaters i know what's that sweaters lorapurapiana. Conspicuous consumption. No, it really is more about markets and startups.

Starting point is 01:31:28 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 layout 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 layout and then from behind my back i throw it up to him and he slam dunks it, right?

Starting point is 01:32:06 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 something, I very quietly give them notes on their performance. And this is after each episode or? After each show. I 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. And so, you know, I had to say to

Starting point is 01:32:40 Freberg, 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

Starting point is 01:33:13 i am not disagreeing with you i'm helping you clarify your position or helping the audience understand your position more that's a very smart way to put it and you are attacking me telling me i'm watching msnbc and i get my information from rachel matto 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 can debate. But I'm

Starting point is 01:34:08 trying to save him from being misunderstood, right? You're like one part moderator, one part coach, one part comms director. I'm not saying that as a bad thing. It's just like- No, no, no. I think it's super accurate. Yeah, you're helping everybody. 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.

Starting point is 01:34:31 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. Oh, it's a different skill. Different skill. 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,

Starting point is 01:34:52 not the point guard, right? May I give one example of why they're totally different? In a one-on-one conversation, you can have a guest who monologues. If you have a group of people, that can be a huge problem. How do you deal with that specifically? Yeah, there's two techniques.

Starting point is 01:35:08 Two techniques. Very good. So you and I like technique. So the two techniques I have, one of them is I say to people beforehand, great job on the show today. At this moment in time, you made four really great points. It would have been better if you made your first one or two and then said, I'm really interested in what Saks thinks of that, or I'm curious, Saks, what you think. And then you have

Starting point is 01:35:31 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 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.

Starting point is 01:35:59 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. It's a little bit generous as a performer 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 we could have let the vocalist lead off the song with an acapella moment right yeah and so

Starting point is 01:36:23 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 to actually adapt to that because certain people, if you interrupt them, it's a trigger for them. Or it can break their train of thought.

Starting point is 01:36:40 I ran into this recently and I was like, I was, I wondered how, like, how would Jason handle this? I was curious. 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 finished 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

Starting point is 01:37:13 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 he just forboating yeah forboating that's the word I was looking for. My dyslexia was killing me on that one. I was like, for Britain? Forboten, it's foreboden, right? You let people finish. But he'll say, okay.

Starting point is 01:37:35 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. I study a lot of what you do. And 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.

Starting point is 01:38:05 That was me imitating you. Yeah. 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 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,

Starting point is 01:38:42 and it really does work as a technique. And everybody's technique doesn't have to work for everybody. I talk fast. You talk a little slower, more methodically. Sam talks even more monotone. He speaks in finished prose. Unless it's about Trump, and then he gets on tilt. It is funny how we all study each other, right? Oh, yeah.

Starting point is 01:39:04 Moderators club. 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.

Starting point is 01:39:32 So you mentioned the McLaughlin group earlier. Are there any people who stand out as good moderators to you? There's not a big cohort of moderators because almost everything is, yeah, I mean, you might say, what's his name from Politically Incorrect? Bill Maher? 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.

Starting point is 01:40:03 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.

Starting point is 01:40:21 It kind of just cracks the whole thing open and we're saying, 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 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

Starting point is 01:40:55 all-in McLaughlin group thing. It would be quite successful, I think. Yeah. Yeah. I guess it comes down to the chemistry, like you said, because with Kevin, it's like we just just it's like having a good improv comedy partner or something it's like your styles just work for some reason yes and then you can always improve the craft and work on it but there is just this baseline of compatible chemistry when 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're going back to friendship we totally kind of spend a little

Starting point is 01:41:29 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 yeah to know that you and kevin are having a great time catching up and we get to be there for it it's just 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 was it and then when the show was going to break up and oh my god what's going on and this is sucks man people was going to break up and oh my God, what's going on? And this is sucks, man.

Starting point is 01:42:06 I've had people wrote me very long notes. Like, you know, I really think you guys need to think about the fans and what the impact is going to 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.

Starting point is 01:42:19 And they're like, it's the same songs, folks. Like you could just listen to the old albums. 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? Yeah, no. When we had our – just now in our conversation, when we were bringing up Ouch My Balls from

Starting point is 01:42:46 Idiocracy, I was like, oh, we're going there? Oh no, are we going to get canceled for liking a funny bit in a movie? Yeah, and the fact of the matter is, I don't think anyone will disagree. 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 for the complete children that we all are. And despite that, given the times, I think the majority of folks feel like they have to

Starting point is 01:43:19 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. Yeah, chill out. It's going to be okay. Take off the psychological corset that they strained to put on in the morning you know 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

Starting point is 01:44:06 a way that i find kind of a bummer yeah 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 yeah i agree 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. Oh, yeah. And both of these are on Patreon. And both of these are behind paywalls, which I think is interesting. Both of them are podcasts where people are being an Overton window that's twice as wide open.

Starting point is 01:44:47 Just for folks who are listening, if they don't know, Overton window. 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. Or that you're going to be persecuted or canceled. Or persecuted, for sure. So there was a time when just even talking about somebody being a homosexual was outside the Overton window.

Starting point is 01:45:11 And if you brought it up, everybody would leave the dinner party and be aghast. Oh, my God. So you had to just treat a person who was a gay person at a dinner party as like, oh, yes, they've got a roommate. And we're just going to sweep that under the rug. Like, oh, yeah, they're here with their roommate. They split their rent because it's cheaper. And then you could be like, yeah, Er've got a roommate, you know, and we're just going to sweep that under the rug. Like, 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.

Starting point is 01:45:29 They're roommates. Pretty obvious. I like the little judo move you 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. It's okay. Yeah, I like it.

Starting point is 01:45:43 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 are so deliberate, so deliberate. Every example you've given,

Starting point is 01:46:05 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? You made that joke earlier about being separated from the success power piece. I think there is something that comes from repetition and getting reps in. You and I are both big fans of that. And so I think having done whatever at the time, maybe 1,300 or 1,400 episodes of This

Starting point is 01:46:43 Week in Startups and all those events interviews i came into all in with a 10 person podcasting team i mean that includes some sales people 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 like wait aren't

Starting point is 01:47:17 there like two for 10 000 people in brooklyn um 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, there's just put spin on it. And I started taking tennis lessons this year and it was like, Ooh,

Starting point is 01:47:35 you know, your brain kind of lights up. Same thing, but different scheme skill. So I think that it was like all that preparation had led to this new thing that you actually keyed off on and we talked about last year for like an hour during the winter of like hey what happened there and so i think that's that was the lightning in the bottle for me personally was i maybe i'm a better moderator than an interview maybe that actually was sitting

Starting point is 01:47:57 there the whole time maybe i'm a better 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 uh 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 mullenweg were sitting around and we took out our net words and it was like oh my god like you and i are down here these two guys are up here we all go and have a steak steak tastes the same We all go and go skiing or we go to Japan, same experience.

Starting point is 01:48:49 And once I realized that, I was like, for me, it might be different for other people. 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, I, you know, like I enjoy sometimes in 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

Starting point is 01:49:28 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. 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 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.

Starting point is 01:50:03 But I was like, you know, I listen to the Tim Ferriss pockets 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 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.

Starting point is 01:50:34 I can see behind the next corner, the book just flows and you're like, boom, 2000 words are coming out at a clip. And you know, like those kinds 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 do another hour yeah and it's hard for me to go to bed some nights because my enthusiasm is so high for life and 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,

Starting point is 01:51:15 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 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. I mean, really, I mean, think about it. Our friend Dave Goldberg, rest in peace, you know, Tony Hsieh, you know, the darkness there. It can be over. It's exactly like our age range where we start saying goodbye to people.

Starting point is 01:51:54 And so if you're in your 20s or 30s, like you're just on adrenaline, and then you get to 40s and 50s, and you're like, huh, what do I do with what's left? Especially if some things have hit for you. If you're Tim Ferriss and you've got to really start thinking, 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? Yeah. Right?

Starting point is 01:52:16 And that's the thing I'm writing in my new book about is, my new book is about money and wealth. Yeah, can't wait to read it. I really can't wait to, well. 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?

Starting point is 01:52:34 It's part, how do you catch the car? But then once I get you on the hook for that, like how do you get the money? Now what happens when you have caught the car? And then now you have to look in the mirror i caught the car okay the adrenaline rushes over am i actually happy did i want to catch that car yeah i want to be tim first did i want to be jay gal did i want to be travis did i want to be matt

Starting point is 01:52:57 mollenweg 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 you know puts things in perspective yeah i mean it does really yeah yeah 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,

Starting point is 01:53:46 when they finally cross that threshold 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 in that book, it outlines just how much self-deception goes into believing that you need 20, 30, 50, 100 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 yeah 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

Starting point is 01:54:41 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 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 is worth studying. I think it tells us a lot about the human condition, even if you never end up catching the car. Yeah. And this is where doing the work internally, and I really respect the fact that you've used some of the resources you've gathered to do the work you're doing in psychedelics. I've never publicly talked about the psychedelic work or psychedelics, period, because as a person who sometimes people follow what I do with a fan base,

Starting point is 01:55:36 I talked about actually taking Ozempic for the first time. I think there's suffering in the world that psychedelics are uniquely qualified i suspect and uh 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 the ketamine or whatever i think the research and the suffering that's happening a lot of it is because people have not done enough of the work to look inside yeah 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.

Starting point is 01:56:21 I don't know if you saw Colorado, I think, passed 122 yesterday. Yeah, it's big news. Very big news. It's big news. Colorado is going to allow therapists to do all these different psychedelics in really safe settings with really qualified people

Starting point is 01:56:36 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 maybe even research this stuff. Because again, you give these disclaimers all the time

Starting point is 01:56:56 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. 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.

Starting point is 01:57:19 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. 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.com slash trauma,

Starting point is 01:58:00 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 the blog post and 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 uh believed through phase three and psilocybin for treatment resistant depression etc if you go to size a 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

Starting point is 01:58:51 see the various universities and a lot of the 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 uh if i'm understanding the 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 landscape and potential reclassification, which you can do through demonstrating medical need, because Schedule 1 is supposed to be, and I'm painting with a very simplistic brush here, but Schedule 1 compounds are supposed

Starting point is 01:59:43 to be drugs 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 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,

Starting point is 02:00:30 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 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. 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. It's just great when combined with a proper therapist. Yeah, they're very powerful. As a friend of mine, I don't think he said it publicly, so I'll

Starting point is 02:01:13 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. Yeah. Yeah, we're coming up. I was like, oh, wow, just a quick 75 minutes, 90 minutes.

Starting point is 02:01:34 I looked down, two hours. Two hours. We are two hours. 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 close, anything that you would put on a billboard, metaphorically speaking,

Starting point is 02:01:45 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? There's part of me that wants to tell people to take chances and that they can do it,

Starting point is 02:02:04 like to give it a shot like 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 brawlers.

Starting point is 02:02:31 But I don't know what's in the air. I don't know if it's since Trump and like this whole polarization in the country, but I would really like to see people be kinder to each other and just have like really open-hearted discussions with each other and i you know i think your podcast to a lesser extent what i'm trying to do on all in i think there are roadmaps here for people to have productive discussions with each other that move themselves

Starting point is 02:02:55 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 can have great friendships. So have those productive discussions with a big open heart and, 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. Have great friends, build cool shit. I put a comma in there. I don't know if I'm allowed to have two sentences. And you know, just building off something you just said, you can have disagreements with good

Starting point is 02:03:38 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. 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 yeah repair yeah wow that's that's a whole nother podcast that's a whole nother podcast it's a whole nother podcast well just promise us tim that you're not going to stop i you know i get worried

Starting point is 02:04:19 a little bit of that we're going to stop doing this podcast like you can take a break yeah but don't ever stop like i mean you're 45 if you do that can you imagine if stop doing this podcast. You can take a break, but don't ever stop. I mean, you're 45. Can you imagine if you do this for another 20 years? How great this archive of Tim Ferriss' podcast is going to be? Yeah, yeah. Think about the legacy. It's hard for me to see stopping. I've thought about taking a break after a billion downloads,

Starting point is 02:04:40 which should happen in the next few months, actually. And as much as I fantasize about burning it all down and going to live in a hut in the mountains and growing out a beard and smoking a corncob pipe and reading books, 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 i'm gonna i'm going to be seeking out incredible fascinating people to have conversations with

Starting point is 02:05:21 whether i'm doing the podcast or not so i might as well record them it's just amazing the impact it's had on society i can't tell you how many people in just people don't know i know you and or that we're friends even and like and so then i'm at a dinner party oh do you hear this you know this podcast by this guy with this thing and i and it's like all the time it's 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. It really is a weird thing. Something about being in people's ears makes it incredibly intimate. I think the AirPods, I think AirPods, specifically like these little things that you can fall asleep asleep in your ears you have them in your ears all the time yeah and this the the act of listening to somebody's voice so

Starting point is 02:06:08 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 it is trippy it's super trippy Thanks for having me on. I can't wait to see you. Can't wait to see you too, man. We're going to play some poker. Oh God, that's a whole separate episode too. I saw that. We'll play for charity.

Starting point is 02:06:36 We'll play for your psychedelic charity. That would be funny. Play for the charity. I'm just Jason on Twitter. Go to Twitter and Jason on Twitter. Anything else you'd like to mention before we wrap up closing comments complaints requests of the audience no no i 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

Starting point is 02:07:00 up and i just like you're a fucking national treasure it's just good to know you thanks man i really appreciate that congratulations on like yeah just you you know like it wasn't always great yeah it was like rough from 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 yeah it's just great to see you at the top of your game oh i told you this in a private conversation it's 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 this is 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 ferris is kind of what i'm doing they come on and they just want to talk about you. And I'm like, whoa, this is tipped over, hasn't it? Famous person is talking about your podcast,

Starting point is 02:07:50 but you're trying to interview them. I was like, whoa, interesting to be Tim first. Anyway, we'll see you all next time. Bye-bye. We got to end this podcast. No, we're going to end it. We're going to end it. We tried to end it five times. I know. We tried to end it five times. It's because we miss each other. It's because we miss each other. Tearful goodbyes. And so I will say this to end it five times. It's because we miss each other. It's because we miss each other. The tearful goodbyes.

Starting point is 02:08:05 And so I will say this, Jason, thank you. It's lovely to see you. I am studying what you're doing. So 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.

Starting point is 02:08:23 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.blogs.com podcast. And until next time, be just a little bit kinder than you think necessary to other people and to yourself and squeeze the shit out of that box of oranges because we're all gonna end up folks 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 i love you brother love you too hey, this is Tim again. Just a few more things before you take off.

Starting point is 02:09:06 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

Starting point is 02:09:30 and all sorts of weird shit that I've somehow dug up in the world of the esoteric as I do. It could include favorite articles that I've read and that I've shared with my close 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

Starting point is 02:09:58 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 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 nauseum. But now I am falling asleep in record time, faster than ever.

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The Tim Ferriss Show - #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

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