We talk to the guy who knows Silicon Valley’s darkest secrets

0:00 I've got Steve Jobs stories, I've got Jack Dorsey stories, I've got Ross Albrick's stories, you name it, I got'em. I feel like I can rule the world, I know I could be what I want to I put my lawn in it like my days off on the road, let's travel, never looking back. Sam has been telling me about a book for probably 10 years in a row. And I finally got around to reading it this year. And the book is American King Pen. It's a story Of the Silk Road, of Ross Albrecht, who Created it.

0:29 Grew it to great. you know, prominence, ended up going to jail, what we thought was for life, and then he just got pardoned by Trump. And so Sam just reread the book. I read it this year. We both love this thing. It's a it's it's a page turner. And the author, Nick Bilton, not only wrote that, but he wrote Hatching Twitter and a bunch of other stuff. Fascinating guy. And uh he's here with us today on M FM. So let's do it.

0:49 Nick, what's going on? We wanted to talk about all types of stuff. We want to talk about storytelling. We wanna talk about things that you researched that didn't make the book. We wanna talk about like the OG stories of Silicon Valley'cause you've been covering this stuff forever. But you're like one of the three people who we've had on the pod that I'm like nervous to talk to and I stayed up all night like reading everything about you. Don't be nervous. This is exciting. This is fun. It's gonna be great. We're gonna tell some some crazy stories. I've got Steve Jobs stories, I've got Jack Dorsey stories, I've got Ross Albrick's stories, you name it, I got'em. Who uh of all those people d w did you have you become friends or uh admire any of them or do you Are you like a strictly like a journalist who doesn't cross the the barrier?

1:30 Well that's a great question. Um, I feel like we should save I should save that answer because I've got such great stories about all these people, about Bezos, everyone. Where You know, there are some that I have become friends with and then unfriends with and some I'm still K kind of friends with, but um We let's save that for for when we get into the hatching Twitter Elon Musk uh Jack Dorsey territory of this of this pod.

1:54 I was listening to an episode with David Perrell. Uh it was all in writing and you talk about um Uh like what makes a great story? And this sounds like a like a backhanded compliment. I think that Your writing's amazing, your story telling is amazing. I think you just happened to pick the best story of all time with the Silk Road. Like it was like set up to to win. Well, I think I mean, uh let me just tell you how I came to the story. So I was a reporter of the New York Times and um

2:19 In Silicon Valley covering tech. I was writing about Apple and Facebook and Twitter and And I I w I don't even know how to describe this moment in time. You know, it was like two thousand eight, two thousand nine. It was, you know, right after the bubble had popped, um, the second bubble, uh, and it was again, once again, this no fly zone, you know, to be in to be in Silicon Valley to do startups and whatnot. And I started covering these m these companies that were not there was the idea of one of them being a trillion dollar company was just it was ridiculous. That would never happen. And I would spend time with Steve Jobs and Bezos and Zuck and and Dorsey and all these guys and I wrote the Twitter book, which which we can talk about and there's incredible backstories to that.

3:01 Um and uh people uh trying to kill the project and so on and so forth. But I'd finished the Twitter book and the Twitter book had done really, really well and I was looking for a new book and um and I couldn't you know, I really I love writing books. It's it's one of my favorite forms of writing to do. And I I Heard about this

3:19 Guy who had started the Silk Road who'd been arrested. This little public library. Uh that was like four blocks from my house. And I I knew the the library, I knew the st and I knew the area, and I also knew the Silk Road. And so I wrote a piece for for the New York Times about it. It's like a short piece. And and then I was like, maybe there's a book in this. And as I started to dig further and further,

3:40 It just felt undeniable. It was like s it was just an unbelievable story of this kid who Um I say kid'cause he was very young at the time, but he Uh he got he grew up in Austin. He

3:50 was incredibly smart, sixteen hundreds on his SATs. you know, studied astrophysics, um, went off to a one of the best schools Uh and and then had this like libertarian idealism to him. That is no different. to like Travis Kellanick when he's builting U building Uber and

4:08 you know, all all these other people in Silicon Valley And he decides the drug should be legal. Uh, and the government should not be able to tell you what you can and cannot put in your body. And the only reason that the the drugs lead to these you know to deaths and murder and so on and so forth is because the government has so much control over it and so he takes The onion browser, which is is the secret browser that you can

4:30 uh where the dark web exists. And then he takes Bitcoin, which b both kind of come along around the same time. And he creates this proof of concept, which is this website called The Silk Road. And then next thing you know, he's But making millions and millions and millions of dollars a day is the biggest drug dealer on the internet.

4:46 By the way, how good was the branding for that? The fact that he called himself the Dread Pirate Roberts, the Silk Road, the like the logo behind it. The branding was actually like The whole the it was pretty brilliant. No, the branding was great. There was I forget the name. There was a name that he had originally c wanted to call. It was like some terrible name. It was called like hardcore underground or something like something where it was like doesn't sound like a P Like I I'm interested in that. But what's what's fascinating is, you know, at the time he's living in Austin, he's got this girlfriend Juan, and they're kind of in this like toxic relationship and he has this business and it's like a it's a

5:20 Pretty Like nice business where He goes around and he collects books that people want to get rid of and then sells them and and and mails them out. So when he When he moves into the drug trade and he goes he goes to Bastrop State Park and he rents a cabin and he grows mushrooms so that he could sell drugs on there to show that you can sell drugs on there. And then he starts mailing them out, like he's mailing the books out. And then the drugs out and like

5:43 And it all kind of, you know, it it all comes together in this very, very unique way. What ends up happening, uh the website That is uh obviously now defunct. Uh they write about it and then that's it. It's like game over. Like everyone on the planet knows about it, and senators are coming after him and every government official from the IRS to the FBI to the secret service to the DEA, they're all

6:06 trying to hunt down the Dread Pirate Roberts and Ross essentially goes on the run around the world as they're as they're trying to catch him. Yeah, it's one of the best things about the book is that it starts with like I don't know how much of this is your Conjecture versus you had his diary, I guess, and you you knew some of his thoughts, but it's like

6:21 He knows he's smart. He wants to do something special. He's sort of bummed out that he hasn't done anything Interesting or special with his life. And s you know, has sort of tried, but hasn't really made it yet doing anything. And then you've got his girlfriend and that there's that part of it. They got the libertarian ideals. And then it leads to oh you know, the thing escalates like crazy where

6:40 I think I I don't know if at its peak but it w I think Silk Road was doing like you know over a billion dollars like GMV through the the marketplace. Yep. And there's like, you know, murder for hire plots going on. Like it escalates like the craziest crime movie would would would escalate. But I like that you had that beginning part where it wasn't just this criminal mastermind. It was like this smart kid. Yeah, just tr tryna trying to do something and had it had a certain set of ideals. How did you know what he was thinking. How did you get access to his diary? Why do why does a writer like how does a writer like you get that? And you got a lot of stuff.

7:12 You got like the footage of the library where he got arrested. You got like the chat logs from you know, from the with the government. How did you get access to all this information? Well I can't tell you exactly how I got a lot of it because that's the that's investigative reporting and uh and I you know obviously can't develop where it came from but The way I approach these stories is I want to know everything, literally everything. Um, and so I have these researchers uh who work for me and one of them uh one of them actually used to do APA research for the for the the Democratic Party trying to find, you know, bad stuff on Republicans and um

7:46 We literally just blanket approach. And what's been really interesting, I have a new project, which I can't talk about, but I can tell you a little bit about how I've been reporting it. What's been interesting is I have it's new project that we're doing. And we've been using LLM Google LLM's notebook. And so now we stuff millions of words into these things and I can just query it. Whereas before we had to build like Excel spread spreadsheets and databases and like It was very, very complicated the way we did it. But We kinda put it into three tranches. So we

8:11 We have The Dreadpire Roberts. And we get access To the chat logs that were on his laptop.

8:19 Um, which I don't actually know if he knew were there because they were in a hidden folder, and I don't think he actually knew he'd been saving them, or maybe he was, I don't know. Uh, and then there's some diary entries. He'd he'd literally been making a diary about about the thing because he would he the the the best line ever is he thought there'd be a book written about his life one day. Um and then we and then we go through social media and we and we get all the photos and all the posts and all that. And we everything's on a timeline. It's all got timestamps. And then the and then lastly it's the interviews with everyone. And with as far as like, you know I we reach out we get your books and you go and you find out everyone you went to elementary school with in middle school and high school and you interview everyone. You're n you find the neighbors, you the kid that lived across the street, uh Um, you know, which coffee shop you went to, you go to the coffee and then the thing I do

9:06 Which is a little psychotic, but I do it anyway, is I want to Be able to describe what that I want you to feel like it's a novel in some respects, but it's all real. Like nothing's made up. And so like if I know he let's say he took a picture, here there's one instance where he went camping. Uh and

9:23 Um and so I didn't know where the campground was. It was in near San Francisco, but he had taken two pictures uh Uh, three pictures, sorry. One was when he left and I we could figure out the street because we could, you know See the angles and the street signs. The next was when he was driving over the Golden Gate Bridge. And then the third was when he got to the campground.

9:42 And we could t tell the timestamps so we just did the math and we're like, Okay, it's probably Forty five to fifty miles away. And then we looked in the circle around San Francisco and then we found these different campgrounds and I went to one and there there we are. At the campground. So I go there. And I find the place that he took the picture from where he's sitting, I sit in that spot and I can

10:01 I can smell the sa the everything and so I can describe that. 'Cause it hasn't changed in in six months or a year. It's still looks the same and And so I do that with like everything. I I go to the coffee shops he goes to, I walk the same street and so You get to describe this and then you also can look You know, with um

10:20 uh with different apps where you can see the way the sun comes on certain days and you can describe what the shadows look like. You just can describe everything. Sam, isn't this wild like to say two it's wild in two ways. One, it's the same sort of obsession of why Jobs is like, I'm gonna design uh we need to finish the inside of the casing of the computer. And they're like, Steve, nobody's gonna see this. And he's like, I've seen it. Um, I know it's there. That's why we have to may finish this the inside uh case. So this is a weird kind of product obsession, which I respect. Um, but then there's also like Dude, nobody would know. Nobody would ever know and it might not ever matter. Why does it matter to you to do that? Well, and it's also weird that Nick, you've written like hashing Twitter wasn't the most favorable towards like Jack Dorsey and some of these guys.

11:02 Mm. You guys all have the same flavor of crazy, though. You know what I mean? Like that that that's what Sean's describing is like what the rights have. Look, I totally agree. Look, I mean it's It's fun for me. I think it's like I I love the challenge, but I it's what's interesting, you bring up jobs, like I sp I spent quite a lot of time talking to him when he was alive, um, and he was incredibly obsessive and of course and like

11:23 And You know, one of the things that he always said that that I mean he said it publicly too, but like You should never know. the the technology exists and how it happens and so on and so forth. And And it's I'm fine coming on a podcast and talking about how I did it.

11:38 But when you're reading, I'm not gonna tell you. Like it there's nothing that drives me more insane where it's like According to uh A transcript that I found it. It's like who gives a shit? Like just tell me the story. And like and And I think that um I you know, one of the beauties of great products

11:55 is when you don't know how it works and they and and I think one of the And y it just works and it's magical and it's, you know, the all those those words that they use in the in the ads and everything. And I think the same sh the same is true for storytelling. You you know, like a lot of the greatest novels. I I voracious reader. I read a ton of novels and um A lot of the greatest novels. The the m amount of research that people like Gabriela Garcia Marcese put into a hundred years of solitude and like

12:22 And to chest it's like when you read these They they're not telling you all this. They're just telling you a story. And why would uh I saw that you ta I think you said in another podcast you spent like three or four weeks with Julia, Ross's uh ex-girlfriend when he was starting it. And there are and and and I didn't know that you had spent time with them when I was spent time with her because I was like, Why why on earth would she ever talk to Nick? Like you know, if I'm her, I'd probably just kinda shut up. But you knew stories like you knew like when they had sex or like like the comments that they made to each other. I'm like, How on earth? Does he know this and then I find out that you I I heard you spent time with her, like getting info. Why on earth would some of these sources talk to you? Why not why won't they just say

13:00 I don't need that in my life. Get out of here. I think um uh One of the things I've learned as a reporter for two decades is that people Talk people wanna talk for different reasons.

13:12 So uh you get you there's you know, endless numbers of them. And one of the thing people think being a reporter is like you gotta break the news and you gotta write the story. It's like no, it's a it's relationships. It's like it is literally just relationships. And And what you have to do is you have to figure out You need these people to talk to you and you have to figure out how to make them want to talk to you.

13:36 And so for example Everyone has a reason. So people that would tip would leak Stuff to me. that worked at Apple or Facebook. Some of them were so just so excited to say, Oh my God, I worked on this thing and it was like and they and they just want it out there and they don't have the patience and you know, and others of them worked on something that never got made or they got fucked over by their boss or they didn't get the credit and like

13:56 Or like They have other the egotistical reasons, whatever it is. And so your job is a As a reporter is to try to get them to talk to you and to try to figure out and my job is to be like why what can I say to you? What is it that you want? I know you want we all want something. And so with Julia

14:16 Um Yeah, I think I think she wanted She wanted to be part of the story. Um, and I think she wanted To be famous a little bit.

14:24 And I also think that she There were uh there were some things that hadn't been said and hadn't been finished and uh and that she hadn't It was like a little bit cathartic, I think, in some respects. Um, and so that's the reason she talked. When it came to the agents. You know, I spent time with all of the agents involved in the case, um or almost all of the agents.

14:43 And um And you know, with Jared Egan and I probably spent four hundred hours, five hundred hours together. You know, we I went to his office, I went to his house, I went to his We we met in all different places. They saw the postal service where he worked and the we went inside the Chicago airport and underneath the

15:00 bowels of it. It was amazing to see all the things that you're going to do. Did you Sean, do you remember that where so Jared was the guy who like he wanted to be an FBI agent or something like that, but he ended up being a homeland security agent, which is like like the book starts with him. It's like one one pill. And what shocked me about Homeland Security and Mail is that they would just sit there and watch packages come in. And they would just be like, That w that envelope looks weird because Uh like it's handwritten in a certain way, uh and it's just similar like it's just so crazy that one of the one of uh a few different ways that he was caught was just like traditional

15:37 uh police work as opposed to like something more complex. It it it was shocking that it was just like eyeballing things. Well's interest I why I started with the pink pill. the single solitary pink pill is because and then there's a there's a uh a line there's a paragraph in the book about

15:55 How you know, the website started with a single line of code and all of a sudden he creates this world and so on. Is I I think what's interesting about techno and that this was just me the way I wanted to tell the story. But what's interesting about technology is also the scene where And I say scenes'cause I think of them in my head as scenes, they're not chapters. I everything's visual in my head.

16:15 And there's this We see a computer being built. And um and it starts with like a single diode. And I what I find so fascinating about technology It's all these websites and all these products and all these companies, they start with this little this it's one thing.

16:30 And the same with the books and everything. And they They grow into these They take over the world. And and so for me, the pink pill, the single solitary pill of ecstasy. was the beginning of the story, which was just gonna become a fucking tidal wave that took over everything.

16:46 Did you ever feel in danger? Uh doing our research. I felt more in danger doing the Twitter book, quite honestly. Um Uh What was the danger there? The powers that be didn't want?

16:59 Jack Dorsey did not want that book out. Uh and he was trying to do everything he did. Dude, he's he's a peace loving hippie, as far as I could tell. He sits with a beard and a tie-dye shirt. He just wants peace and love for all, I thought. Look, there are definitely stories I've worked on. I wrote a book that didn't that we I chose not to publish. It was just about the N R A. Um this was um after Marjorie Stoneman Douglas it happened'cause I went to school there and um it spent a couple of years on the book and then then decided to not do it for for a few reasons. But

17:31 That one I wouldn't even say there was W I wasn't Like afraid someone would come after me. Except maybe like some gun nuts later. Um you know I've done some stories.

17:41 mafia stuff like Russian hackers, things like that. Um And Yeah. I've never like you know, I think a lot of the times People respect

17:52 the process and they don't they they don't want to start a war w with the New York Times or Vanity Fair or you know. I think it's different if you're like covering Mexican cartels in you know In Mexico, that w that's that's a whole different thing. Or if you're trying to be a reporter in Russia or something like that, that that's where you really do have to start to worry. But in Silicon Valley it's a bunch of nerds that

18:14 You know, talk a big game and And And that's it. I did have I do have one story, uh But it's from the Twitter book. So When I

18:23 I won't mention names here, but when I I wrote the Twitter book and there's a moment in the book where Uh s someone gets fired. And I got a call from a friend who's a journalist at Bloomberg. And they said, Hey someone there's a there's a bunch of people These like crisis PR people that are trying to

18:40 Ha they're calling all the journalists, they just called me and they're trying to say that your book is all fabricated and it's not true and this especially this moment, it's all made up. And um And I just wanted to let you know. And I was so I just called this woman directly. And I was like Hey.

18:55 Uh heard you're calling everyone and saying she and she's like I didn't say that and I was like I said look, I have the tapes of the interviews and uh of that moment. And I was like, I will happily post it on Twitter. I said, You just keep calling people and I'll put it on Twitter. And

19:10 That was the end of it. So you know, uh so there are these moments where you get these crisis comms people that come after you, but Well you know y when you do as much research uh research as you do Um you end up getting to know the subject in some ways better than themselves. It's like these business and business these you know, CEOs will pay for these expensive three sixty reviews where you go where somebody goes and talks to their wife and their their co-workers and their uh interns and they get they come back with this feedback and it's supposed to be this eye opening thing about them. Uh, th this person can can find out more about them and s show them a mirror that they haven't really seen before. In that case, they want it.

19:44 But um you know, when you're researching Jack Dorsey and you say something like you know That's all a story. Who's the real Jack Dorsey? Well I think just one just one thing about what you just said. Is

19:56 I know w somebody asked me once, how do you know when your book is done? When you're like when you're ready to to 'Cause what happens is you research for for a long time, you don't write a word until you're ready, until you've done all the research and you have everything. And I have in my office I have these boards and I like create these cards like that that you can you know where they're just all the scenes of and different colors and everything and Put them up on a wall and um

20:21 And uh and I know that when I'm ready to write. when I start telling the people I'm writing about things they don't know about themselves. And that's the moment I'm like, Okay. I got it. And so that happened with the Twitter book. I remember sitting with all the founders

20:37 And there was a moment where I told Evan Williams something that had happened be behind his back that I thought he knew about and he he had no idea. And I was like, Oh, okay, well, there you go. I'm ready. And you know As far as Jack specifically goes

20:52 The best quote I ever got about Jack Dorsey, and I've written a lot about him, was um from one of the board members years ago. Uh Who said the best product Jack Dorse ever made was Jack Dorsey. Because it's because that's what it is. It's a

21:09 Everything is everything is a story, right? Every single solitary thing we do every single day is us telling a story. The w the outfit you chose to wear today is a story about yourself, me telling a story about the book is me It's we're all it's all we're doing all day long. And we're telling these stories and we choose which story we want to tell certain people but based on how they want us to pr to perceive us And I think that people like Jack and Jobs

21:36 And Bezos, all of these guys and Zuck. They That's one of their One of the things they're great at is telling a good story. And And I think like I personally believe

21:48 That your story for a company It's more important than Anything. I don't care if you have the greatest product in the world. If you can't tell a story about it. Well what's the point? W what's the example that drives that home?

22:00 YouTube is a perfect example. YouTube was not the first video platform. There were dozens. And I remember seeing this. Like when I was a uh just a a beat reporter covering Silicon Valley and And I would my days were like it was like office hours and you'd have like startup after startup in like two thousand nine, eleven, twelve come in and meet with you and they would have, you know, some of them have great ideas. And And but

22:23 Couldn't walk you through it and they didn't hire a PR person and they didn't like And And so You know, and YouTube

22:31 YouTube had a great story. And and that they were able to tell And that became and it became The video platform. There were other video platforms that were I would argue way better. than than YouTube. And I mean Vimeo is a perfect example. Vimeo was a was a a thousand times of a better product.

22:48 And um A prettier, easier to all these things and And YouTube just told a great story and Google helped them do that. And it becomes That's what it becomes. And if you if Jack Dorsey had told the real story about Twitter that his best friend Noah Glass really was the one that came up with most of it.

23:05 And he stole it. You know, from him and and like And the that place was a shit show and no one knew what was going on. It was all an accident. Like You'd be like oh okay, but

23:16 I but to tell the story that I am the next Steve Jobs and and I I conceived of this idea of Twitter while I was in my mother's womb and and it like Holy shit I gotta check this thing out. What is this? And it's like the Jack Dorsey Twitter story I know is He grew up and he was just fascinated with dispatch or something like that, he talks about like I loved

23:37 uh ta either taxi dispatch or some some transportation dispatch services to listen to in that short form. Dispatch communication was always something he was into. And then when had the you know the idea for Twitter and he has the sketch You know, he's posted before

23:54 That's the story that I know, right? Because I'm on I'm just the receiving end of that product he's story worked, right? That story the story worked. Uh does is it true? No, it's not true. Uh in the same way he was interested in the writing poetry and painting his nails black and dyeing his hair blue. Like, but that's not part of the story because What really happens is and as I say in hatching Twitter and af and no one knew this. I I was like I had to talk to all these different people to kind of pin it together. Except Noah Glass knew it. Um

24:24 Was You know, Jack. was living in San Francisco. He was in his the early thirties. He was like a part time manny Uh in Oakland. He Like he his life had not turned out in any way like the predestined version of Jack Dorsey we think of today.

24:40 He got a job working at a um You know the ticketing boost at Alcatraz? Um the so they're these booths that are pretty small and he was the C Programmer. who would go and fix the ticketing booth. And the reason he got the job was'cause he was small enough to fit inside the booth and program. Uh um so this was the life he was living and he

25:01 He had went he applied for a job. Like camper shoes. To sell shoes. Not Not like uh to build the website or be the CEO. Like

25:11 And he couldn't get the job and he was at a coffee shop and Evan Williams walks in and he read an article about Evan And he just felt like it was a sign. Which it probably was. The universe was putting them together. She sent him a note. And he said, I'm a programmer and you know And um they had Odeo at the time, which was the podcasting company, which was A decade ahead of its time. Um which was

25:32 a a brilliant idea that n that Noah Glass had come up with. And so Noah and and Evan Williams had had created this thing called Blogger. Um uh and Blogger was Again, ahead of its time, you know, and Google purchases it and one day this guy, Biz Stone, reaches out and he says, I love blogger, I'd love to come work for you. And uh so Evan Williams and

25:54 There's become friends at Jason Goldman, who's also another p part of this. He's working at Google. They all kind of become buddies. They end up leaving. Um and get Goldman stays, but Evan Biz end up leaving and the reason that they leave is because Evan lives on I think it was like eighteenth in market or whatever the streets were. And he one day he was on his balcony. And another guy, Noah Glass.

26:17 was on his balcony and Noah had been reading that same article that Jack Dorse had read. And he recognized In the article that the photo of Evan was taken on the balcony and in the background there's a little Noah glass.

26:33 Because they were neighbors. And so he goes out and he goes, Hey blogger And they become friends and then He pitches in Noah pitches in this idea for this podcast company. He's like, This is the vision, this is the future, it's gonna take over radio, and so on. And so Ev is like looking for a project, and so he agrees to do it. It's all discombobulated, no one knows what's going on, like they can't run the startup.

26:54 Apple comes along with podcasts. They're they're screwed. Jack Dorsey comes along. And they hit do a hack day. And um to try to like s last hurrah to save the company. And They um

27:07 During the hack day, Jack presents this idea for status. Okay. And everyone's Everyone's kind of doing the same thing. The uh the ideas are very, very similar, and I'll tell you a couple of them. But Jack presents this idea for status. And what status is is stat dot us slash Nick Dalton. Right.

27:23 And you go there. And You see my status. It's one status. If I say And it's Three four words. You're not really supposed to do anything more than that.

27:32 On a podcast. Now if you go an hour from now, if I put it post a new status and I'm like Taking a walk. The on a podcast is gone and it now just says taking a walk. It's like an A em away message. It's literally an A em away message that they were doing and

27:46 And so So Noah has a very similar idea. But Noah's like No one is going to go stat.us slash Nick Bilton. Five times. Your mom will do it.

27:59 'Cause she wants to know what you're up to. But no one else is doing that. And so they all start bringing these ideas together. And it's truly it's like eleven people in the room. It it is a collaboration between all of them. And what Noah has this realization is He's a very emotional guy, very smart. And he's like, it needs to be about friendship.

28:18 It needs to be about connecting with your friends and that is what it's about. And so he brought this humanity to it. And so he came up with the stream and the repli it's like all the not the app replies, but the friends like that you had friends and you And that was what that was Twitter. It wasn't status. You know, it it it there were a million other statuses uh back then. I mean

28:38 Um And so When it ends up becoming what it became, Noah was a mess. He was getting divorced. He was like he just his life just wasn't work and and he gets pushed out by Jack and and Ev and and those and Jack, who is best friends with Noah, goes into Ev's office one day and he says, Either you get rid of Noah or I quit. And as far as Avenue Jack could come up with the idea himself.

29:01 You know, when he was a little kid listening to Fire Trucks, that was a story that was added later. And um And so You know So but that's but the better story. is not oh I screwed over my best friend.

29:15 For power and control of this thing. It's When I was a kid, I used to sit in my room at twelve years old and I had the vision for Twitter by listening to Fire Trucks. Okay, that's a great story. And so

29:26 You know You seem like you don't like Jack Dorsey, is it? Uh you don't like him or you just feel like that's a wrong that needs to be writed to that story is you want to keep the record. That is I I don't like people who fuck other people over, especially their friends. Did you find yourself like you had this great podcast with our friend David Perrell and you set a line that

29:47 Hitchcock someone came up with where it was um Every villain has a mother. Uh, and it was like uh I guess like you you see yourselves in the villain at times. That's what a good stories do. You kind of like Uh. like a villain a little bit or they're a little ig uh ign uh you know you're they're you're they're you're interested in them.

30:03 Did you find yourself liking Ross? Did you find yourself liking Jack at times? Like Because you get so into their minds and you also see that like Even though they do a lot of bad things, they do a lot of epic things, a lot of big things, do you find yourself admiring and liking them? Well, they all have a charisma to them, you know, that that um you can't

30:23 Pull this off without the charisma. Um I met Trump. He's very charismatic. Very, very charismatic. You like want to be around him, even if you don't agree with him. What was the context? How'd you meet him? Oh, just a this uh at a rally once um years and years and years ago, I think two thousand fifteen or something like that. You know, spent time with Elon, like he's kinda funny. He's funny. He's like a weird dude, but he's funny, you know. Jobs had this like

30:46 aura to him, you know, Bezos too. Like they Um funnily enough, Zuck doesn't necessarily have the charisma, but it's almost like he's a robot and you're like, Oh, how does this thing work? But um But they all have this This There's something to them that is um

31:04 Uh that is enticing and and and Jack's funny. He's a funny, nice guy. Like when you're hanging out with him. He like You y it's like you're you're like, Oh, this he's fun. I like hanging out with this guy. And um And And so And I never met Ross. I covered him in the court in the trial, so I saw him many, many times, but never spoke to him.

31:22 Um and um But they have this charisma to them that I think makes them great in some respect. And it's not something that you can learn. It's just something that you h either have or you don't have. And um And so You cannot help but like them for that, but I

31:39 Think for me, I just I don't understand f here's the part with Jack and then we should move on from it because uh I could talk all day about this, but Jack is worth twelve billion dollars. Give or take.

31:54 Um Noah glass is worth About Zero dollars. Okay. He never got

32:01 Anything. He w Ev gave him something and he had to live off that and and and whatnot. If you're worth twelve billion dollars. Give the guy Ten million. You wouldn't even notice. You'd it would literally be like losing a penny between your couch cushions.

32:15 And like that to me Even if you believe that you are the creator, even if you believe that, that you that you really came up with this on your own, because he may believe that today. I just don't understand like why the kid that you were best friend the guy you were best friends with who who without question helped you with this product. Like

32:34 Go take care of him. And it never happened. And for the class, I agree with you. But also No Glass now has a thing too, right? Doesn't they have Olo or No, that's a different No Glass. No shit. They're not the same guy? Not the same guy. So

32:49 Everyone thinks that. I thought they were the ex I thought it was like his second coming. No, he's uh he just he has a family and he like he married this French woman and they have two kids and I think not only Twitter got stolen from him, his own name got stolen from him. His name's Google got stolen from him credit. Mess him up. I did not know that. I thought it was I thought it was like Oh, he's getting it he's getting it back. Oh man, that ruin the story for me. Can you can you tell us some other um stories of uh that that have stood out to you, things you still remember, either experiences or whatever. You said like I got job stories, I have Zuck stories, I have Elon stories. Let's let's see uh jobs is the best one, I think. I'll I'll I'll do the jobs story. Um

33:30 So when I was a reporter at the Times Um, I I didn't really know what I was doing. Like no one knows what you're doing when you start out in these jobs. Uh, you pretend you do, but you don't. And uh Um And I o I don't even think I think the ten thousand hours is nonsense to think it's about thirty thousand, right, to really understand what you're doing properly. But

33:52 I was at the Times and I was and what had happened was I come into the Times um By complete accident. Uh Uh let me just start with that story'cause it's actually a very funny story. So I was a I was my dream job was I wanted to be a war photographer. Um and I'd read all these war photography books and uh and I

34:12 bought like saved up and bought like a fancy camera and I would like to practice war photography with my friends where they would like run through the streets with you know, and I would take pictures and And so I put together this portfolio and I was a graphic designer. Um I'd done toy package design for a while, um and like designed the verse Britney Spearsdall and stuff like that.

34:33 And so I was like, Oh, I can use the designer job to get to the times as a designer and then I can become a war photographer. And so I end up Doing that. I become I

34:43 do page layouts and stuff like that. And when you do these The way these meetings work is uh the at at the these newspapers you have a morning meeting where all the editors and reporters go in one big room and each section, the business section, the culture section, the front page and so on. You pitch they pitch their stories, the editor decides which is going to go where on the front page and and and off you go. And but I would always speak up because I didn't know you weren't supposed to. And so I'd be like, well what about this? And what about that? And I like that. And what if you did this? And

35:11 And I just became like friendly with a lot of the editors. One day I sit down with the photo editor and I show her my Photos. And she looks at it and her name is Michelle McNally and she like slowly goes through one by one. And she closes the book and she goes She's like, You're a good photographer. And she's like, I think you'd be a you'd be a good war photographer, but I'm not gonna hire you to do it. And I was like, why not? And she goes, Because you're too normal.

35:32 She's like these guys are fucked up. They're on drugs. They can't be in a they can only be in a war zone half the time. Like They've got like They've just got something that's missing that they need that adrenaline and she was like I don't Feel that from you.

35:46 And I'm grateful that so grateful that she she said that. And so I was like well, what do I do now? And There was the at the times Um Uh

35:56 I become friends with with Marissa Mare and I that was talking about going over to Google to go to Google News. I mentioned this to the editor in chief of the business section. And he said, Oh God, I wish we could keep someone like you to be like a reporter because everyone wants to write for the print section. No one wants to w write for the web.

36:15 And I just The words just came out of my mouth. I never wanted to be a writer. It had never been anything on my list of things I wanted to do. And I said, Well, I would do it. And he was like, Oh well, why don't we try it? And then I was like, Oh shit, what have I done?

36:29 And so The first day. I'm on the job at the New York Times and I'm in this massive newsroom with all these insane People that you know. back then you were just like enamored by these these bylines that you were just like holy shit

36:42 And uh my editor comes over and funnily enough, it was Twitter had gone down and he said, Twitter's gone down, can you write a blog post about it? uh, you know, call the company and everything. And I was like, Yeah, yeah, yeah, no problem. And so I looked at my computer and I Googled how do you write a blog post? Uh so that was my first And then I realized like, oh my God, what have I done? I'm

37:02 I Food in this job that I just don't know what to do. And so I just I spent weeks just reading every byline of the greatest reporters

37:13 And I was like, Okay, this is how they write the intro, this is how they do the quotes, this is how they do the nut graph. And I just figured it out and I made mistakes, but like that was my That was my foray into it. So one day About

37:27 I don't know, a six months a year into me being Attack blogger for the Times. Um I reach out to Apple. as you know, you call and you say, Hey I'm doing the story and this you have a comment. And um

37:39 the PR woman that answers uh Uh she says, Um Steve's gonna call you. And at the time there was a guy called Steve Dowling, who was like a very senior com person. And I was like, Oh cool, Steve Dowling and she goes, No jobs. And I was like

37:52 But And uh and I was like, Is that normal? Does that happen? And she goes sometimes he's gonna call you, wants to talk to you. And I'd been writing a lot of Apple stuff and um And so he never called.

38:03 And that night I went out for dinner. uh with my girlfriend at the time and and then we went for sushi and I had a I had like a few sockies. And then all of a sudden I get a phone call from this number in in in San Jose and I answer it and it's jobs. And I was like a little tipsy.

38:20 And he talked to me for like an hour and he just he just like convinced me not to do the stories in the way I did it. And I didn't I didn't it didn't make any sense, but I w he made so much sense. And he just kept he was like, Oh well you got this wrong and that and then if you actually if you look at this you can do and And then the next day, so I wrote the piece and then a couple of days go by. You know when like you've seen a movie And then all of a sudden you process the movie and then it's like oh that makes sense.

38:47 I r I played this conversation back in my head and I was like Holy shit. He convinced me not to do the story that was that was the right story. He got you. He got me. And so John Markov, who is a veteran reporter, I told him and he goes, he just says it's the reality distortion field. And I was like, What's that? And he goes, Jobs Jobs invented it. And

39:06 And every time I would talk to him from time to time and every time it was the same thing. It was like this He had this ability to to make you believe the what you were doing was not the right story and that this was the way to do it. It was it was a really fascinating thing to see. How does the reality distortion'cause I've heard that so many times, the reality distortion field.

39:26 Never been in it. You've been in it. What is he actually doing, in your opinion? You're a smart guy, you're a storyteller, you're a persuasive guy, you've been around other charismatic people. W is it just his aura, is it his gravitas? Is he really good at reframing things? Is it Um Is it intimidation? What is he actually doing? And it's one of those things where you hear about and you're like

39:46 That won't happen to me. No, exactly. I was I yeah, like Hm. I i uh it's hard to describe what he's doing'cause it's so Interesting. He

39:57 He convinces you that you're wrong. And you believe it. You know, you um And look I think

40:05 Uh Th there's a part of jobs. That We should all admire and respect and And B

40:14 be really amazed by but there's the part of him that he was He he could be a real asshole. Like um Walter Isaacson told me this story once. Jobs it was pro was He presented the iPad. And and then what they did back then, they don't do it anymore as much because

40:29 the media has changed so much. But what they did back then was they would go around to all the newsrooms around the country. And they would meet with the editorial boards and the reporters in in off the record, in total private. And they would show you the products that they were doing. So Um

40:45 Presidents would do it too and you know, you would sometimes get invited, you'd they'd be like Yeah. Bushes here or the Secretary of State. Like come and it's of huge at the New York Times it was this

40:54 massive conference room and on the walls were all these photos of all the dignitaries that had come over the last hundred and fifty years and And business people and so on. And so we got a call that jobs was coming. And there was

41:07 twenty of us that were invited to this thing. And I end up getting sat next to Brad Stone, who now runs Bloomberg business. And uh And Jobs was right next to him and Brad was the the Apple reporter at the time and I was the tech blogger. And there was this moment where he passes he brings an iPad prototype and you know we're Playing with them and everything and I was prodding it too hard and he was like

41:28 Stop it. You're hitting it too hard, Nick. And I was like, okay. Uh and so but then he says this is another reality distortion field. This actually will make more sense. He says um We're doing questions and answers and and everything. And then I said to him, I said, Steve, I saw you

41:43 A couple of years ago w uh at Cupertino and you were sitting Um There was Three stools on stage and you were on one of the stools. And you were just presented the Apple television.

41:53 Box. You said That you see Apple As um Having these

42:01 These Three businesses, right? Um, there's the Mac and there's the iPod,'cause that's what it was back then. And And whatever and I said, And then you said Apple TV will be the fourth lag. So

42:11 the stool will become a chair, something like that. And I remembered it verbatim back then. Um and He goes. I never said that. And I was like, No, I'm I you no, you said that. I'm pretty sure you said that and he goes

42:23 I never said that. He goes, I've never said that about Apple Tel Apple Television's the experiment for us. We're just playing with it. It's like, you know'cause it wasn't doing very well at the time. And that was my question. It's like it's not doing very well. Like did you say that incorrectly? And and I was like And I'm sitting there with all the editors and the h uh you know, and the big the big macas of the at the New York Times and I'm like And I'm just like this young reporter and I'm like, No, you you definitely said that and he goes, Nick I never said that.

42:51 And I was like Okay. And so and then I just like shut up and then afterwards John Markov was there again, too. I pulled it up on my computer.

42:59 And I was and I watched the video, I was like, He said it and he goes, reality distortion field. And that was just it. And so what was I gonna do? Go run around to the twenty people in that room and tell them to say that he made it up? No, he he did what he Did and it worked, and they all believed that that was just an experiment. Right. Are there any of these guys that you felt like had it had Had it all. They have the extreme success.

43:24 They're the they're the extreme achievers of society. But you know, most of the time you look and they're on their fifth wife. And they're kind of an a the story is that they're kind of an asshole to work for or that they screwed somebody over, whatever, right? Like they they have Same as this quote, you know, Show me a great man and I'll show you a bad man, right? Like you know, there's a

43:42 Stereotype with that. Was there anybody you met that you were like, No, this person's actually They had it. They did they had the career success, but they also were a good family man or they were actually good to be around. They're a good good human being to be around. Yeah, people who you would say they're winning. Yeah. Um There was one person

44:00 And I say was. There there's two. Th there are other people. Look, I I think like there are really good people in that in Silicon Valley. They're not the most successful of like, you know they're not the h worth the hundreds of billions. Like I love Aaron Levy. I think he's a great guy. Like Dennis Crowley. you know, I d there's along the people that I really, really admire and like and I think are good people. Um

44:20 But there was one person that I was like, Oh, you have it all. And I had met him because I'd done these series of stories on uh on the Kindle and uh Um it was Jeff Bezos. And I remember spending time with Bezos and When I became

44:36 a columnist at the New York Times, like when I got promoted to be a columnist. There was a guy I work with David Carr. who was just a wonderful, wonderful human being. Who was the media columnist. Uh, and um he's since passed away, but he was like

44:51 He was everyone's mentor. He wouldn't make time for anyone. He was just a lovely, lovely person, so smart. And when I became a columnist, I didn't the first few columns I wrote, I was like, I don't know what the hell I'm doing. And uh and David used to smoke outside and I would go down and like hang out with him. And he said uh And he said, Pick a fight that you can win. That's what you need to do.

45:10 The first time. When you first become a columnist. So I was Flying out to LA for for Thanksgiving and I was reading a book on my Kindle back then. It was like

45:19 Two thousand uh ten and nine, eleven, twelve. And Um I was reading a book on my Kindle, it was like three pages to go, and I was like, Oh my God. And they were like, You must turn off your air put your devices off now and put them in airplane mode and whatever. And um

45:33 And I And I wanted to finish so I was like hiding the book so I could finish it and the air the stewardess was like We are not allowed to take off star until you turn that off and I was like It's a calculator. Like it's not gonna d destroy the plane. And she got very terse. And I was so angry that when we finally got up to to altitude, I wrote a column about just how ridiculous it was.

45:54 And it got published like the next day or whatever, and it was like the most read thing on the on the New York Times for weeks. And I was like, Oh, I'm picking this fight and so I started doing Went to all these testing facilities because back then you were allowed there were rules in the FA you could use a razor.

46:12 A tape recorder. A heart monitor and some other so we got all these. She caused it uh going to petic court. Yeah, you're going to Petticourt. Yeah, that I was I was in Petty Court. And so I we went to these testing facilities and we did like EMP testing and we put a Kindle these it's amazing, these giant rooms that like And you just have a device and it can test all the EMPs. It turns out like the razor puts off like a hundred times more EMPs than a Kindle. And so I did I just kept writing these stories'cause people like were so irate about the fact that they couldn't read their Kindle or play on their phone while they were taking off.

46:45 And eventually it got overturned. And um and Bezos during his earnings call that quarter was like uh on the earnings call was like I wanna give a shout out to Nick Bilton for like'cause it helped his business, of course, you know? And um Anyway I end up meeting with him uh and um And

47:04 He was like So smart. And thoughtful and just you could tell was on a different level. Like he you could just see like Oh, this is someone who

47:16 who never forgets anything, who and he was married, he was talking about his kids and how his his teenage son still sits on his lap and like and then I ended up again going to a dinner at his house And um uh and he you know. Talking about his family and like And

47:31 I met his wife McKenzie many times and And I was like, Oh, this he's the guy who has it all. He's like created this unbelievable business. He um He doesn't from what I could tell, he's not uh like people don't say he's an asshole to work for, right? I'm sure there were some, but most people like really, really loved working for him and stayed at Amazon for years and loved the culture. And then uh and then they got divorced and he ended up uh in a very, very different relationship. So I um

47:59 Uh And now you like he's like this Bodybuilding looking like Raver. So he I think he had it all, but for whatever reason he had like this midlife crisis that made him throw it all away. I don't know. I don't know. But that was the one person that had it all. I I want to talk about one more thing. Um

48:18 Do you want me to tell that w that Walter Isaacs installed? Oh yeah, yeah, yeah. Go ahead and come back to that. So Walter told me the story of after the iPad where He had met jobs in the four seasons, I think it was, which is connected to the The Um

48:32 m Moscone Center, um and they had met for breakfast. I don't know if it was before or after the iPad. And jobs. Had ordered A fresh squeezed orange juice. And the waitress brings it out.

48:43 And it's not fresh squeezed. It's got like pulp in it. And he calls her back over and he says I asked for a fresh squeeze orange And um She brings another one out, again that's got Pope in it. And he just

48:54 becomes more and more Angry. And about this orange juice. And at one point It it sends and she's almost in tears, this like this this poor waitress and At one point

49:05 Um Like Steve, what are you doing? Like it's just an orange juice. Like she's trying like she clearly doesn't they they clearly don't have like non-pulp orange juice because it's fresh squeeze, whatever. And he says if if she's chosen to be a waitress for her living

49:22 then she should be the best waitress she can be. And it's my job to push her to do that. And it's like No, you don't know her backstory. You don't know like where her life has gone and why and things like that. And like And I think that like So for all the brilliance there was a lack of compassion.

49:39 And look, we all I think the thing is, the reality is like None of us are perfect. We're all kidding. You're one of the best there is. Do you lack that comp I mean, like are you accused of being an asshole? I yeah, I I fucking love when people call me an asshole. Like I just like I I just don't give a shit. But like

49:56 I what I pride myself on Is I pride myself on being very, very Easy to work with. Like if if we're doing a creative pr if we're wr if we're writing a movie together and I'm working with the producers or if we're doing a documentary, like

50:10 I am there. to make this the best possible and не you I will never Ever, ever be an asshole. You and you could never find anyone that would say I would. Because I understand that what we're doing is really hard and we're all doing our best and like there's the pursuit of creating great creativity. However

50:29 I've picked fights with people as a writer and a journalist and gone after people that makes me into a fucking asshole, quite honestly. You know, like I had a thing Um When Dave Morin was doing, you know, all of his

50:45 products and startups like I went after Him and and then later I actually later apologized to him'cause I felt like I was To much of an asshole and we had like a heart to heart about it. And like And I do think like

50:58 There's a great line that Bill Keller, he was the editor in chief of the New York Times for many years, used to say and he used to say I don't believe people should be able to write about other people until they have been written about themselves. And I learned that when I people started writing stories about me and it was like oof, that feels awful. Like that sucks. And it was like a moment where I realized like oh Like I don't need to be such a dick to people. Like I can

51:20 I can I can write these stories and I can be honest and I can tell the truth, but I I need to you need to have some compassion too. And I you know, that was something I had to learn in my the beginning of my career. You talk about like your time at the New York Times where you're like We were in this room and then the the room had the portraits of all the important people who used to come to us and

51:39 And try to tell us what they were doing because we were the messengers and we used to kind of shape the narrative out there and they tried to shape us and we shape the narrative. Yeah. And there was these People who were You know, you recognize their names from the bylines and you had just like so much respect for them. Do you think that that's still like The k like does that shit matter at all anymore? Because for me

51:59 I'm like if I'm a founder of a company now, I don't I put zero dollars in the PR. I put zero care in if if I could get a press mention. It's like so low on the total poke compared to how it was fifteen years ago when I was building a company That has changed my my respect for kind of mainstream I I think Trump really like reality distorted everybody when he started going after fake news.

52:20 And then you started seeing examples of it. Like I just feel like the credibility has gone s down, but I'm also on the outside, you're almost you're you know, you're you're from that world. Do you feel the same way or do you Do you think that's completely misguided? There's a practical thing of like you ha you can get an audience on Twitter on wherever and you're like I don't I don't you nor do I need you. Um uh there's two answers to that question. And the first answer is that I think ninety percent of the media is utter garbage.

52:47 And it is complete and uttered. ridiculous drizzle. That is opinionated. And uh bad for society

52:55 And I think ninety I think ten percent is people that are working really, really fucking hard to try to do investigative reporting. Because they care. And I met those people. I remember those people at the New York Times when I first started. And I had they were they you know, they were people that were making A hundred and twenty grand a year. And

53:14 ha could be making millions, like working for a hedge billions, I don't know, for b like wherever they wanted and they Wanted to Pursue the pursuit of honesty. And Setting the record straight and going after these bad people,'cause there are a lot of bad people in the world.

53:29 Does that ninety percent of the uh the crap include your past employers? Does that does that include New York Times? Yes, one thousand percent. Because I think m and because the system it all broke. Like it's broken be and I I believe it's broken beyond repair for now. I I my hope is that And maybe this is me being delusional, but like my hope is that AI can somehow help fix it, but For but I believe that Or AI in the hands of people can help fix it. But

53:56 When I first started at the Times, like You weren't allowed an opinion. You weren't allowed there was no s the you know, you there was no social media, like with there was no Twitter. Like I was at the times when Twitter came out. Like You if I remember being in meetings in those rooms and I would ask an editor

54:12 Right. What do you what do you think? And they would be like, I'm not I don't have an opinion on this. My I'm a journalist. who comes at this impartially and all I want to do is report the facts. And And and so I think that What happened was you had this the the prod problem was the internet came along.

54:29 Right. And you had to to get to the times, like I was the first one that one of the first ones that came in I remember being In a meeting once. with forty or fifty people at the time it was this big meeting and everyone kind of went around and they introduced themselves and they talked about like where they'd gone to school and how they'd ended up here.

54:46 I I barely graduated high school. Like I literally had a two point one GPA, I got kicked out of art school. And like they were all like I was at Harvard and I worked at the Harvard Crimson and I did this and the other and I was like, Oh, I'm the odd one out here. that shouldn't be here. And like was only here because no one wanted to write for the internet.

55:03 And that became Everyone became that. And And I think that like What ended up happening was you had this generation that came in after I left

55:14 That was They were all they they were the internet people. They hadn't been mentored. They hadn't You know, they hadn't learned the robes and And they didn't and they felt like they had a right. To say oh we shouldn't

55:28 We should not publish Tom Cotton. in the opinion section. And we're gonna Go I'm gonna be irate because we That is not the way the world works. The world works is by listening to other people's opinions and like А на

55:41 that so many people in Silicon Valley have have veered to the right, which they have. Is because The left tells them, Oh, you can't think like that, and you can't and you're stupid if you believe this and so on and so forth. And I think that So the pr the whole apparatus is completely broken. But at the same time

56:02 I d'em friends with a lot of s startup founders who tell me that like Oh, we got a profile in the New York Times and we had the biggest Influx of customers we've had. Ever or we got mentioned, you know, a a write up on here or whatever it is, and the same thing happened. And so

56:19 The eyeballs are still there. People just don't necessarily trust them l in the way that they did. And I and I think that, you know Mm-hmm. What's interesting is that You have all these new news outlets that come along, like Samaphore and the Free Press and things like that.

56:34 And they're trying to get people They're trying to say we're we're impartial in the middle and so on and so forth, but inevitably what ends up happening is As soon as you put that opinion in, the viewer the everyone the the the number of listeners or viewers or readers go up and then the product ends up steering that way. And so I think that there is a

56:53 desperate need for something that is What I think the solution is, honestly, is you you You know, you don't need a right wing publication or a left wing publication. You need a both. You need a place where there are people who have right wing point of views and centrist point of views and left wing and they're all in there together and they're debating it and they're respectful of each other and maybe they disagree. But they are all there. And the problem is the New York Times is all left and the Wall Street Journal is all right and so on and so forth. And Um

57:22 And so you you don't necessarily trust any of it. Yeah, I would love to read the debate. I think that's a lot more interesting format. Um people who take the other side two people who each each believe or are willing to like argue the best case for each side so you can read it. And I think that's both entertaining because it's sort of a fight, an intellectual fight, uh, but I think it's also more informative because you get Both perspectives, you know, sort of steel manned. Yeah.

57:46 Is there a story you wish you could write, either if you had like infinite time or Uh, you know, sometimes you get successful and you're like, Oh, somebody should do that. It's probably not worth me doing it, but somebody could do that. Is there is there a great story out there that you think somebody should be doing? Uh I don't know. I my dream is I uh I've I love thinking about stories from all different perspectives, like how, you know

58:08 When do you do when is a story a documentary? When is a story a book? When is it a magazine? When's it a tweet? When's it a movie or or a nine part series on Netflix, you know, and and I do I write all all forms of of writing and and um and I'm fascinated by You know, there's there's these different things that's that are fascinating. It's like Um you know.

58:30 A documentary Is The people From the past. Talking about there uh in the present talking about the past.

58:39 Right. Uh a T V series is the story unraveling as you're watching it unravel. A book is You get to climb inside, crawl inside someone's head for seven hours.

58:50 And let them understand how visually things smelled and looked and done I've always might I wanna write a novel at some point. I think that that's like the next thing I wanna do. Um And so Uh'cause I love every

59:05 I'm a voracious novel reader and um And I just have so much respect for the amount of research that goes into them and then they become But they don't it's like it goes back to the beginning, like the magic is you don't know that The people that wrote the novel. Spent

59:19 hundreds of thousands of hours researching all the history or whatever it is to to to do that. Um As far as like a net nonfiction, like I just love stories that are That you know, that old cheesy saying that like, you know, it's If it was fiction, you wouldn't believe it.

59:34 You know, it's like I really think that those are the stories that to me are Um are the most The most fun to read and Report and research. You have uh all these different seasons of life. You know, you said you in evolution, you said you want to be a war.

59:49 uh photographer, then you accidentally became a column a columnist and then you uh became an author And You've even though you've dislike some of the guys you cover. It sounds like there is a lot of admiration still for uh a bunch of others as well. Have you ever thought about like going into the business world, um, since you've been able to see it so closely?

1:00:09 Uh, I almost did this year actually, there was a project that I was gonna Go do um which was a startup in in the storytelling space. Can you say what it is? I think that what's happening is there's a change coming

1:00:22 In Hollywood as far as um how we consume content and short form versus and the way You know, there's there are these structures that happen to stories that um that we that become norms. And so for example In a film screenplay. A film screenplay is a hundred and twenty pages long because each page is a minute. That's why when you look at screenplays they're courier in the certain font'cause

1:00:45 Each page shot is usually one minute long and so one hundred and twenty pages is a two hour movie. And so there's a There's a whole system set up. There's a book called Uh Save the Cat, which essentially made this world where you you on page one, the first person you meet is is your is your main protagonist. Um by page three you have

1:01:04 Discovered what the movie's about. By page five, there's the introduction of the antagonist. By page thirty Every single movie if you go back and watch on page thirty, which is thirty minutes in, It's the changing moment. It's the you know, it is the Joseph Campbell, like this is when the journey begins.

1:01:21 And and then by page ninety, you've entered the third act and and we we've come back around and so on and so forth. And um And while every movie is different We We understand that that's the same thing, and I think what what's happened is

1:01:37 That That um Philosophy has been overused. And I think do you remember the movie Parasite? uh that won the Academy Award. Parasite changed it and

1:01:48 It wasn't by paid sixty, it turned into a whole different movie. And you were like, Whoa I've never seen that before. And that's why people I think really loved it. And I think what we Oh. What we look for in culture is Things that are new and different and every once in a while a genius comes along who does it. And um

1:02:07 And then everyone else copies that and then you gotta wait for the next genius to come along to do the thing. And um And I think that the That page one, page five, page thirty, page ninety thing is completely doesn't work for today's audiences. They don't have the patience to wait till page thirty to find out when the turn is. And so In short form, there's like this new philosophy of like

1:02:27 One second, seven seconds, nine seconds. And I think that like But then they don't know how to tell stories. And I think that there's a world where um, you know, there's we were exploring this idea of like Thinking about the new approaches of how to tell Long form stories and short form

1:02:43 bites and things like that. And um but at the end of the day, like The reason I didn't end up doing it is because I just love telling stories and I don't necessarily Wanna be like a manager meeting with VCs and boards and

1:02:56 And getting kicked out by Jack Dorsey. How many uh how many copies How many copies of your books have you sold? Uh hundreds of thousands of copies, yeah. U o over time. Um I don't I haven't checked in a long time, but Uh hundreds of thousands and they've been printed all over and why is America Kingpin not a Netflix like seven part series? Like in a campaign. It was okay. That movie was okay.

1:03:21 I mean no, it was bad. It was bad. It was bad. I'm not gonna tell you the story, but the reason the reason it has not is because I got screwed over on on uh film film rights deal, so That's the reason why. But it may end up in it's still today, it still may end up uh may end up there. We'll see. Alright, if I wanted to spend six weeks

1:03:40 Getting as good as I could at storytelling, what would I do? Is there a book or is there some process like If I was dedicated, how would I become an amazing storyteller? Well if you dedicate you need more than six weeks. So let's pretend it's what can I do in six weeks? I got nineteen bucks. What do you got for me? I have all these books on like on storytelling that I read and like and they're interesting and like you get a little snippet. I think the most interesting of all the books was that I read was um When I wrote a hatch on Twitter, I really wanted it to feel like a murder mystery because no one knew what really happened. And I read a book on murder mysteries, which was unbelievable. Like you can read any of them, just Google like how to write murder mysteries.

1:04:22 It's a it's a blue book, it's a collaboration where a bunch of murder writers and and screenwriters and so on each write a few chapters each. And there's a few things I learned from that which were Um, which one is um I When you read a lot of books

1:04:38 Um people forget to describe smells. Um, and murder mysteries always do. And it's like and it brings it really brings you in. It's it's wild to see how it can add like this extra layer like sounds, smells you know, the noises, you know, um Uh not just the creaking stairs, but But the you know.

1:04:58 the mold or whatever it is, it just creates this sense of story in your brain. The other thing is um the Save the Cow, which is a really interesting even if you don't write screenplays, it's a really interesting way of understanding character and so on and Um I read a bunch of screenplay books by like some of the old greats and they talk about characters and and and things standing in your way and so on. But I will say for me the best way to become a great storyteller is to read stories. And I think one of the things that frustrates me about Silicon Valley

1:05:28 And the tech bro culture. is everyone's trying to optimize their life for the most number of seconds of this and that and the other, and it's like What they don't realize is that Some of the greatest Things that they will learn.

1:05:42 is from things that have nothing to do with what they do. So I've in in Uh I'm forty eight now. When I was forty five I I love listening to piano music. I I've never I was like, you know what? I'm gonna I'm gonna just learn the piano.

1:05:56 Uh And um and I got obsessed with it. I learned how to read music for the first time. Oh look at you. What is that? I'm on a That's it's like a New Year's resolution. This is my uh how are you doing. How is it? I'm on the Faber method here, so I'm on book two A right now. I'm playing uh

1:06:15 I'm playing. There's a great app. It's like um it's called um that I do in my spare time. It's called Notes Teacher. And you just do it for like five minutes a day. Sight reading practice. Yeah, sight reading practice. But I got obsessed, obsessed. Like I literally would play two hours a day and like now I can play a couple of Chopin songs and things like that. And I And the thing I and to me it was just a fun hobby and it was like really like but what you learn is that like

1:06:40 They are telling a story. And they're telling a story, you know, Hans Hans Zimmer says like The notes will ask a question and then the next notes will answer the question and it's like and the way Chopin I like is you just unbelievable when you If you sit and analyze the music and think about like the highs and the lows and the things that are repeated and It's and it's amazing and it and it started to kind of inform

1:07:01 Some of the ways I thought about screenplays and like I read As many as many novels as I can. I hate nonfiction books. I can't read nonfiction books. Which is funny'cause I write them. Uh just they're just boring to me. Uh so I um but I read novels and I love

1:07:17 like to studying as I'm reading, like, oh, that was really unique of the way they did this. And I I read a lot of like nineteen fifties sci-fi, and then I read a lot of like nineteen thirties, forties, six fifties, sixties Um incredible, you know, the like the the writers that we all should read. Um And You just understand that they it's really

1:07:37 These stories are about People. They're not the stories that that we think that it's like The the guy who wrote Game of Thrones, George R. Martin, I saw him speak once at a conference years and years ago, and he said, You know, you could take my story, you could put it in a spaceship and it would still work. You could put it in present day and it would still work because it's about the relationships and the characters. And I think that that's

1:07:58 What ends up happening is as you watch something w the best stories are the ones where you imagine yourself as the character And then you wanna know how you would solve the problem. If I'm James Bond, how would I get out of this as the as the drill is about to s you know uh sever my Heart or whatever.

1:08:19 And and then you can't figure it out and the storyteller does and you've you're like Delighted by that. 'Cause it's great. Storytelling. I think that's your secret, by the way. You're like I I nonfiction Is usually pretty boring. But yours aren't.

1:08:31 And I think yours aren't because you consume so much content that's uh you know, on the mystery side, yours are page turners. And so what You know, that lateral thinking where you take a skill from one discipline and apply it to another that usually doesn't have it. That's what some of the best business people do as well is they take Yeah, the best.

1:08:48 uh uh hedge fund, you know, Renaissance is because they took the best AI Machine learning, mathematical prowess and applied it to finance. Um, and like we had Mark Mike Posner on the podcast and he was talking about How he started as a rapper, but all his hit songs

1:09:04 Are him singing. And he's not the best singer, but he's like, I am the best writer because he and he sang one of his lyrics and he's like the rhyme scheme I'm using here, the reason people like that hook and it's catchy is because I'm using a rap rhyme scheme, which no singer songwriters would typically do, but that's why my song sounds different because I'm using a rapper's lyrics, but I'm singing them in the way that um, you know, is is rarely done. But it sounds like you've kind of done that same thing. No, it's c I think it's totally true. Now look I think jobs

1:09:33 Jobs did this thing where he You know, computers back then were these nerdy Like circuit boards and he was like Oh, I'm gonna marry graphic design. with technology. And so for me, like I want to marry

1:09:46 the style of a novel with a narrative nonfiction story. And um and you know, there's great writers who've done that in the past that I such such admiration for. Whenever I get done reading your books, like when I get done each time after I've read American Kingpin, I'm like pretty bumped. I'm like, uh I was so like in love with like reading this and I was looking forward to fit or I was looking forward to like I would sneak off to like find the page and and see if I can just like read a few ch uh chapters. And I felt Bummed that like I was like in this relationship with this book and it's over now.

1:10:17 And I would I've like searched so long and hard to find something that could fill that need. And like only one out of like twenty or thirty books like fills that need. I think Mastermind was another great book that was a very similar topic and he did a and the the author did a great job of a very similar style of storytelling. But in general, it's been really hard for me to find things I I read a lot of novels, but I like reading I like Sometimes when I read a novel I'm like I fall in love with this character and then I find out that I have to remind myself the character is not real and I get kind of like bombed about it, you know. And so what who do you view as a peer Uh or uh someone you look up to or you they do

1:10:53 Your style of Nonfiction storytelling. Oh w well, just real quick on the novel, like Yes, they're not real, but they are based on Reality.

1:11:03 Like every Every novelist pulls from the people around them to create the characters that you're reading. So You know

1:11:12 It's like what you know, if you go do research into like whatever your favorite book is. uh your favorite novel, like and you look at how they did it, if they talk about it, they're like, Oh this, you know, when I was a kid, them I had my grandfather used to tell me the stories about da or like there was a neighbor across the street. So I think they are it is real and it's still people Um as far as as um As far as people I admire. Uh and I look up to I I like I said before, I don't really read a lot of narrative nonfiction. Uh I'm sorry, a lot of nonfiction. I I don't think there's

1:11:41 That Like it I and I love I've have such admiration for people's reporting and and even their writing, but it's just I I need a story. I can't have a So That's what I'm describing. I want more like story driven, not story. This is the shit, man.

1:11:57 I've just Like I just love learning about this stuff. Well you had you had one last question, Sam, and I interrupted you. What do you what or did you get into it? Well it was about um I uh Sean, did you see the documentary on Netflix about uh was it what was it called? Uh it w with Ilia, was it Bit Bifinex? What was that called? It was the couple, uh uh Bitcoin, Bonnie and Clyde. I did a documentary on them for Netflix, uh with Chris Smith, who did Tiger King. uh that was about this couple that had stolen five point four well they stole seventy two million dollars in crypto uh and then were trying to launder it and every they were the only two people on the entire internet who wanted the price of Bitcoin to go down.

1:12:35 Uh, and they had every time they were trying to launder it, it would double and double and double and double and double until the point that it was one point at its peak was worth eight point four billion dollars. And she was this like wacky uh cringe wrapper and he was like a part time magician investor and like it's one of those stories. If it were fiction, you'd be like, Yeah, this is stupid, this would never happen. She uh Sha or the the guy, Ilya, spoke at the very first hustle con, which is kinda funny. Uh And then the woman Heather New Forbes thirty into thirty, dude. Well listen, listen, listen. The woman Heather, she was like a copywriter or something, but she wasn't any good. And she like DM'd me asking To talk at one of our things or to like Do freelance work or something like that. And then uh

1:13:19 She was kind of a sex freak. I had a bunch of friends that like fooled around with her. And they were like, This woman's wild, man, uh you should stay away. Like like those type of stories. And I was like joking with Nick, I was like Whoever I guess we interact with, just like you know, maybe ten percent of'em are gonna end up becoming like amazing criminals, uh because for some reason we we've been around a bunch of these people like right as or right before they were committing some huge crime. Um

1:13:44 But that was also a good story. Yeah, that was a great story. That was just wild story that they uh that they went on they went to Ukraine and like Uh had like fake passports and I mean it it was just yeah, it's nuts. Is uh is making a Netflix documentary is is there good money in that, or you do it just'cause it's sick and it's like, you know, it's art and I'm doing this for art. How does that work?

1:14:06 There's not look, being a writer I think y y you know Yeah, it's good money, like if you can pull it off. There's somebody sent me an article a while ago that you're more likely to become a billionaire than to become a Uh A successful writer. Uh and

1:14:21 Yeah, it's like I think the way In the olden days. y you know, at Vanity Fair, for example, or or the New Yorker, they had these contracts for these writers. They would get paid hundreds of thousands of dollars a year and they would write four stories a year and like And then they had the house upstate and the place the brownstone in Brooklyn and like it was a different time and now

1:14:41 you know, everything's been dilute media has been completely diluted, um, where we have podcasts and blogs and newsletters and mainstream media and all s and all the stuff. And so The advertising dollars and the revenue dollars, th it's not like they've gone up. It's just they've evenly been more evenly distributed. And so For me, uh I just wanna tell stories and the

1:15:04 Uh And I just don't give a shit in what format it is. And so it's really fun to be able to write screenplays, to write books, to write magazine features, to make documentaries and like and then, you know, it all just kind of adds up from there. I could talk to uh with you for hours, man. Thank you for doing this. Thank you so much for having me. This has been really fun. We appreciate you. Alright, that's it. That's the pod. That's the pod.

1:15:26 I feel like I can rule the world a no way be what I want to I put my all in it like my day song On the road less travel never looking back

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