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

25:19The universe was putting them together. So he sent him a note, and he said, I'm a programmer. And they had Odeo at the time, which was the podcasting company, which was a decade ahead of its time, which was a brilliant idea that Noah Glass had come up with. And so Noah and Evan Williams had created this thing called Blogger. And Blogger was, again, ahead of its time. 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 so Evan Williams and Biz become friends at Jason Goldman who's also another part of this he's working at Google they all kind of become buddies they end up leaving and we'll 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 18th and Market or whatever the streets were and he one day he was on his balcony and another guy Noah Glass was on his balcony and Noah had been reading that same article that Jack Dorsey had read.

26:22And he recognized in the article that the photo of Evan, of Ev Williams, was taken on the balcony. And in the background, there's a little Noah glass 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 future. It's going to 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. Apple comes along with podcasts. They're screwed.

26:57Jack Dorsey comes along and they do a hack day and to try to like last hurrah to save the company. And during the hack day, Jack presents this idea for status, okay? And everyone's kind of doing the same thing. 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.us slash Nick Bilton, right? And you go there and you see my status. It's one status. So if I say, and it's three, four words, you're not really supposed to do anything more than that, on a podcast. Now, if you go an hour from now, if I post a new status and I'm like taking a walk, that on a podcast is gone and it now just says taking a walk.

27:41It's like an AM away message. It's literally an AM away message that they were doing. And 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 because 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 11 people in the room. 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. It needs to be about connecting with your friends.

28:20And that is what it's about. And so he brought this humanity to it. And so he came up with the stream and the app. It's like all, 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? There were a million other statuses back then. I mean, and so when it ends up becoming what it became, Noah was a mess. he was getting divorced. He was like, his life just wasn't, and he gets pushed out by Jack and Ev 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.

28:56And as far as Ev knew, Jack had come up with the idea himself, you know, when he was a little kid listening to fire trucks. That was a story that was added later. And so, you know, but the better story is not, Not, oh, I screwed over my best friend for power and control of this thing. It's when I was a kid, I used to sit in my room at 12 years old, and I had the vision for Twitter by listening to fire trucks. Okay, that's a great story. And so, you know. You seem like you don't like Jack Dorsey. Is it you don't like him or you just feel like that's a wrong that needs to be righted? That story?

29:34Yes. You want to correct the record? That is. 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 perel and you said a line that 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 story is do you kind of like uh like a villain a little bit or they're a little uh you know you're you're you're interested in them did you find yourself liking ross did you find yourself liking jack at times?

30:07Because you get so into their minds and you also see that 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, that you can't pull this off without the charisma. I met Trump. He's very charismatic, very, very charismatic. You want to be around him, even if you don't agree with him. What was the context? How'd you meet him? Oh, just at a rally once years and years and years ago, I think 2015 or something like that. You know, I've spent time with Elon. Like, he's kind of funny.

30:42He's funny. He's like a weird dude, but he's funny, you know. Jobs had this, like, aura to him. You know, Bezos too. Like, they, 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 that is enticing and and jack's fun he's a funny nice guy like when you're hanging out with him he like you 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.

31:23But 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 either have or you don't have. And so you cannot help but like them for that. But I think for me, I just, I don't understand. Here's the part with Jack, and then we should move on from it because I could talk all day about this, but Jack is worth$12 billion, give or take. Noah Glass is worth about a zero dollars, okay? He never got anything. Ev gave him something and he had to live off that and whatnot. If you're worth$12 billion, give the guy$10 million.

32:11You wouldn't even notice. It would literally be like losing a penny between your couch cushions. And like that to me, even if you believe that you are the creator, even if you believe that, 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 friends, the guy you were best friends with, who without question helped you with this product, like go take care of him. And it never happened. And for me, that's - Well, No Glass, I agree with you. But also, No Glass now has a thing too, right? Didn't they have Olo or - No, that's a different No Glass.

32:43No shit. They're not the same guy? Not the same guy. So, everyone thinks that. I thought they were the, I thought it was like his second coming. No, he's, he just, he has a family and he like, he married this French woman and they have two kids and I think they live in France. not only Twitter got stolen from him, his own name got stolen. His own name got stolen. Google got stolen from him too. This guy gets no credit. Mess him up. I did not know that. I thought it was like, oh, he's getting it, he's getting it back. No. Oh man, that ruined the story for me. Can you tell us some other stories that have stood out to you, things you still remember, either experiences or whatever?

33:20You said, like, I got job stories. I have Zuck stories. I have Elon stories. Let's see. Jobs is the best one, I think. I'll do the job story. So when I was a reporter at The Times, I didn't really know what I was doing. Like, no one knows what you're doing when you start out in these jobs. You pretend you do, but you don't. And I don't even think, I think the 10 ,000 hours is nonsense. I think it's about 30 ,000, right, to really understand what you're doing properly. But I was at the Times and I was, what had happened was I'd come into the Times by complete accident. Let me just start with that story because it's actually a very funny story.

34:03So I was, my dream job was I wanted to be a war photographer. and I'd read all these war photography books and I bought like, saved up and bought like a fancy camera and I would like do practice war photography with my friends where they would like run through the streets, you know, and I would take pictures. And so I put together this portfolio and I was a graphic designer and I'd done toy package design for a while and I'd like designed the first Britney Spears doll and stuff like that. 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.

34:39And so I end up doing that. I become, I do page layouts and stuff like that. And when you do these, the way these meetings work is at 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, they pitch their stories, the editor decides which is gonna go where on the front page and off you go. 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?

35:10And I just became like friendly with a lot of the editors. And one day I sit down with the photo editor and I show her my photos. And she looks at it and her name was 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 good war photographer. But I'm not going to hire you to do it. And I was like, why not? And she goes, because you're too normal. 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.

35:44And she was like, I don't feel that from you. And I'm grateful, so grateful that she said that. And so I was like, well, what do I do now? And there was at the Times, I'd become friends with Marissa Mayer. And I 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 write for the web 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 what have I done?

36:29And 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. 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? So that was my first. And then I realized like, oh my God, what have I done?

37:02I found myself 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. 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 foray into it. So one day, about, I don't know, six months, a year into me being a tech blogger for The Times, I reach out to Apple. As, you know, you call and you say, hey, I'm doing the story in this. Do you have a comment? And the PR woman that answers, she says, Steve's going to call you.

37:44And at the time, there was a guy called Steve Dowling who was like a very senior comms person. And I was like, oh, cool, Steve Dowling? And she goes, no jobs. And I was like, what? And I was like, is that normal? Does that happen? And she goes, sometimes he's going to call you. He wants to talk to you. And I'd been writing a lot of Apple stuff. And so he never called. And that night I went out for dinner with my girlfriend at the time. And we went for sushi and I had like a few sake's. And then all of a sudden I get a phone call from this number in San Jose. And I answer it and it's jobs. And I was like a little tipsy.

38:20And he talked to me for like an hour. And he just, he just like convinced me not to do this stories in the way I did it. And I didn't, I didn't, it didn't make any sense, but I, he made so much sense. And he just, he was like, oh, well, you got this wrong and that. And then if you actually, if you look at this, you can, 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. I, I played this conversation back in my head and I was like, holy shit.

38:50he convinced me not to do the story that was the right story. He got you. He got me. And so John Markoff, 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 invented it. 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 make you believe that what you were doing was not the right story and that this was the way to do it. It was a really fascinating thing to see. How does the reality distortion, because I've heard that so many times, the reality distortion field.

39:26Never 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. Is it just his aura? Is it his gravitas? Is he really good at reframing things? Is it intimidation? What is he actually doing? And it's one of those things where you hear about and you're like, that won't happen to me. No, exactly. I was, yeah, like he, it's hard to describe what he's doing because it's so interesting. He convinces you that you're wrong and you believe it. You know, you, and look, I think there's a part of jobs that we should all admire and respect and be really amazed by.

40:15But there's a part of him that he was – he could be a real asshole. Like Walter Isaacson told me this story once. Jobs was – he presented the iPad and then what they did back then – they don't do it anymore as much because 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 off the record in total private. And they would show you the products that they were doing. So, and presidents would do it too. And, you know, you would sometimes get invited. They'd be like, you know, Bush is here or the Secretary of State, like, come in.

40:52It's a huge, the New York Times, it was this massive conference room. And on the walls were all these photos of all the dignitaries that had come over the last 150 years and business people and so on. And so we got a call that Jobs was coming. And there was 20 of us that were invited to this thing. And I end up getting sat next to Brad Stone, who now runs Bloomberg Business. And Jobs was right next to him. And Brad was 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.

41:25And I was prodding it too hard, and he was like, stop it. You're hitting it too hard, Nick. And I was like, okay. And so, but then he says, this is another reality distortion, Phil. This actually will make more sense. He says, we're doing questions and answers and everything. And then I said to him, I said, Steve, I saw you a couple years ago at Cupertino, and you were sitting on, there was three stools on stage, and you were on one of the stools, and you had just presented the Apple television box. And I said, you said that you see Apple as having these three businesses, right? There's the Mac and there's the iPod because that's what it was back then and whatever.

42:07And I said, and then you said Apple TV will be the fourth leg. So the stool will become a chair, something like that. And I remembered it verbatim back then. And he goes, I never said that. And I was like, no, you said that. I'm pretty sure you said that. And he goes, I never said that. He goes, I've never said that about Apple. Apple television's an experiment for us. We're just playing with it. It's like, you know, because it wasn't doing very well at the time. And that was my question. It was like, it's not doing very well. Like, did you say that incorrectly? And I was like, and I'm sitting there with all the editors and the, you know, and the big macas at the New York Times.

42:42And I'm like, and I'm just like this young reporter. And I'm like, no, you definitely said that. And he goes, Nick, I never said that. And I was like, okay. And so, and then I just like shut up. And then afterwards, John Markoff was there again too. I pulled it up on my computer 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 going to do? Go run around to the 20 people in that room and tell them, say that he made it up? No, he did what he did and it worked. And they all believed that that was just an experiment. Right.

43:16Are there any of these guys that you felt like had it all? meaning they have the extreme success. 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 ad, the stories that they're kind of an asshole to work for, or that they screwed somebody over or whatever. Right. Like they, they have the 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, there's this stereotype with that. Was there anybody you met that you were like, no, this person's actually, they had it.

43:48They 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 human being to be around. Yeah, people who you would say they're winning. Yeah. There was one person, and I say was. There's two. There are other people. Look, I think there are really good people in Silicon Valley. They're not the most successful of like, you know, they're not worth the hundreds of billions. Like I love Aaron Levy. I think he's a great guy. Like Dennis Crowley, you know, a lot of people that I really, really admire and like. and I think are good people.

44:20But there was one person that I was like, oh, you have it all. And I had met him because I had done these series of stories on the Kindle. And it was Jeff Bezos. And I remember spending time with Bezos. And when I became a columnist at the New York Times, like when I got promoted to be a columnist, there was a guy, I worked with David Carr, who was just a wonderful, wonderful human being, who was the media columnist. and he's since passed away, but he was like, he was everyone's mentor. He would 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.

45:00And David used to smoke outside and I would go down and like hang out with him. And he said, pick a fight that you can win. That's what you need to do the first time when you first become a columnist. So I was flying out to LA for Thanksgiving and I was reading a book on my Kindle back then. It was like 2010 and 9, 11, 12. And 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, put your devices off now and put them in airplane mode and whatever. And I wanted to finish. So I was like hiding the book so I could finish it.

45:37And the stewardess was like, we are not allowed to take off to her until you turn the night off. And I was like, it's a calculator. Like it's not gonna destroy the plane. and she got very terse. And I was so angry that when we finally got up to altitude, I wrote a column about just how ridiculous it was. And it got published like the next day, whatever. And it was like the most read thing on the New York Times for weeks. And I was like, oh, I'm picking this fight. And so I started doing, I went to all these testing facilities because back then you were allowed, there were rules in the FAA. You could use a razor, a tape recorder, a heart monitor, and some other.

46:15So we got all these things. Sean calls it going to Petticourt. Yeah, you took him to Petticourt. Yeah, I was in Petticourt. And so we went to these testing facilities, and we did, like, EMP testing, and we put a Kindle. It's amazing. These giant rooms that, like, and you just have a device, and you can test all the EMPs. It turns out, like, the Razer puts off, like, a hundred times more EMPs than a Kindle. And so I just kept writing these stories because 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. And eventually it got overturned.

46:47And Bezos during his earnings call that quarter was like, on the earnings call was like, I want to give a shout out to Nick Bilton for like, because it helped his business, of course, you know? And anyway, I ended up meeting with him and he was like so smart and thoughtful and just you could tell was on a different level. Like you could just see like, oh, this is someone who never forgets anything. And he was married. He was talking about his kids and how his teenage son still sits on his lap. And then I ended up going to a dinner at his house. And he's talking about his family. And I met his wife, Mackenzie, many times.

47:33And I was like, oh, he's the guy who has it all. He's like created this unbelievable business. he doesn't from what I could tell he's not people don't say he's an asshole to work for I'm sure there were some but most people really really loved working for him and stayed at Amazon for years and loved the culture and then they got divorced and he ended up in a very very different relationship and now he's like this bodybuilding looking like raver I think he had it all but for whatever reason he had 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.

48:15I want to talk about one more thing. Do you want me to tell that Walter Isaacson story? Oh, yeah, yeah, yeah. Go ahead. Yeah, 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 Moscone Center. And they'd met for breakfast. I don't know if it was before or after the iPad. Jobs had ordered a fresh squeezed orange juice. And the waitress brings it out. 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 squeezed orange juice. And she brings another one out.

48:52Again, that's got pulp in it. And he just becomes more and more angry about this orange juice. And at one point, she's almost in tears, this poor waitress. And at one point, Walter says, like, Steve, what are you doing? Like, it's just an orange juice. Like, she clearly doesn't – they clearly don't have, like, non-pulp orange juice because it's fresh squeeze, whatever. And he says if she's chosen to be a waitress for her living, 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.

49:34And, like, and I think that, like, so for all the brilliance, there was a lack of compassion. And, look, we all, I think the thing is, the reality is, like, none of us are perfect. We're all good and bad and bad and good. Yeah, well, do you think you have that? You're one of the best there is. Do you lack that compassion? I mean, like, are you accused of being an asshole? Yeah, I fucking love when people call me an asshole. Like, I just, like, I just don't give a shit. But like I what I pride myself on is I pride myself on being very, very easy to work with. Like if we're doing a creative, if we're right, if we're writing a movie together and I'm working with the producers or we're doing a documentary, like I am there to make this the best possible.

50:13And I will never, ever, ever be an asshole. 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 the pursuit of creating great creativity. However, 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 when Dave Morin was doing, you know, all of his products and startups, like I went after him and then later I actually later apologized to him because I felt like I was too much of an asshole and we had like a heart to heart about it.

50:55And like, and I do think like, 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 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 write these stories and I can be honest and I can tell the truth, but you need to have some compassion too.

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51:57Boom. Deal closed. Cash in the door. That's the kind of banking experience I want. And that's why I use Mercury. So if you're running a startup and you want banking that feels like it's built in this century, well, go to Mercury.com and get started in minutes. Mercury is a financial technology company, not a bank. Bankless services are provided through Choice Financial Group, Column A, and Evolve Bank and Trust members, FDIC. you talk about like your time at the new york times where you're like we were in this room and then the room had the portraits of all the important people who used to come to us and 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 shaped 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 like does that matter at all anymore because for me 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 and if i can get a press mention it's like so low on the total compared to how it was 15 years ago when i was building a company that has changed my my respect for kind of mainstream i think trump really like reality distorted everybody when he started going after fake news and then you started seeing examples of it like i just feel like the credibility has gone down, but I'm also on the outside.

53:14You're almost, 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, you can get an audience on Twitter on wherever. And you're like, I don't, I don't want you, nor do I need you. There's two answers to that question. And the first answer is that I think 90 % of the media is utter garbage and it is complete and utter ridiculous drizzle that is opinionated and bad for society. And I think 90, I think 10 % is people that are working really, really fucking hard to try to do investigative reporting because they care.

53:52And I met those people. I remember those people at the New York Times when I first started. They were people that were making 120 grand a year and could be making millions, like working for a hedge, billions, I don't know, like wherever they wanted. And they wanted to pursue the pursuit of honesty and setting the record straight and going after these bad people because there are a lot of bad people in the world. Does that 90 % of the crap include your past employers? Does that include New York Times? Everywhere, yeah, 1 ,000%. Yes, 1 ,000 % because I think – because the system – it all broke. Like it's broken – and I believe it's broken beyond repair for now.

54:32Now, my hope is that, and maybe this is me being delusional, but like my hope is that AI can somehow help fix it. But I believe that, or AI in the hands of people can help fix it. But when I first started at the Times, like you weren't allowed an opinion. You weren't allowed, there was no, you know, there was no social media. Like there was no Twitter. Like I was at the Times when Twitter came out. Like you, I remember being in meetings in those rooms and I would ask an editor, right? What do you think? And they would be like, I'm not, I don't have an opinion on this. I'm a journalist who comes at this impartially.

55:07And all I want to do is report the facts. And so I think that what happened was you had this, the problem was the internet came along, right? And you had 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 40 or 50 people at the Times. 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. I barely graduated high school. Like I literally had a 2.1 GPA. I got kicked out of art school. And like, they're all like, I was at Harvard and I worked at the Harvard Crimson and I did this and the other.

55:43And 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. And that became, everyone became that. And I think that like what ended up happening was you had this generation that came in after I left that was, they were the internet people. They hadn't been mentored. They hadn't, you know, they hadn't learned the ropes and they didn't, and they felt like they had a right to say, oh, we shouldn't, we should not publish Tom Cotton in the opinion section and we're gonna be irate because we did. That is not the way the world works.

56:24The world works is by listening to other people's opinions. And like, and I think the reason that so many people in Silicon Valley 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 whole apparatus is completely broken. But at the same time, I am friends with a lot of 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 write-up on here or whatever it is and the same thing happened.

57:05And so the eyeballs are still there. people just don't necessarily trust them in the way that they did. And I think that, you know, what's interesting is that you have all these new news outlets that come along, like Semaphore and the Free Press and things like that, and they're trying to get people, they're trying to say 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 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 desperate need for something that is – what I think the solution is, honestly, is you don't need a right-wing publication or a left-wing publication.

57:51You 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 point of – 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 so 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. Totally. Two people who each believe or are willing to argue the best case for each side so you can read it.

58:25And I think that's both entertaining because it's sort of a fight, an intellectual fight. But I think it's also more informative because you get both perspectives, you know, sort of steel-manned. Yeah. is there a story you wish you could write either if you had like infinite time or 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 a great story out there that you think somebody should be doing? I don't know. My dream is I love thinking about stories from all different perspectives, like how, you know, when do you do, when is a story a documentary?

58:58When is a story a book? When is it a magazine? When is it a tweet? when's it a movie or a nine-part series on Netflix, you know, and I do, I write all forms of writing, and I'm fascinated by, you know, there's these different things that are fascinating. It's like, you know, a documentary is the people from the past talking about, they're in the present talking about the past, right? A TV 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 and let them understand how visually things smelled and looked and da-da-da-da-da.

59:42And so I've always, I want to write a novel at some point. I think that that's like the next thing I want to do. And so, because I love, I read, I'm a voracious novel reader. and I just have so much respect for the amount of research that goes into them and then they become, but then 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 hundreds of thousands of hours researching all the history or whatever it is to do that. As far as like a nonfiction, like I just love stories that are, that, you know, that old cheesy saying that like, you know, if it was fiction, you wouldn't believe it.

1:00:22You know, it's like, I really think that those are the stories that, to me, are the most fun to read and report and research. You have all these different seasons of life. You know, you said in Evolutions, you said you want to be a war photographer, and then you accidentally became a columnist, and then you became an author. And even though you've disliked some of the guys you cover, it sounds like there is a lot of admiration still for a bunch of others as well. Have you ever thought about going into the business world since you've been able to see it so closely? I almost did this year, actually.

1:00:59There was a project that I was going to go do, which was a startup in the storytelling space. Can you say what it is? I think that what's happening is there's a change coming in Hollywood as far as how we consume content and short form versus the way. You know, there are these structures that happen to stories that become norms. And so, for example, in a film screenplay, a film screenplay is 120 pages long because each page is a minute. And that's why when you look at screenplays, they're courier and the certain font because each page shot is usually one minute long. And so 120 pages is a two-hour movie.

1:01:38And so there's a whole system set up. There's a book called Save the Cat, which essentially made this world where you, on page one, the first person you meet is your main protagonist. By page three, you have discovered what the movie is about. By page five, there's the introduction of the antagonist. By page 30, every single movie, if you go back and watch, on page 30, which is 30 minutes in, it's the changing moment. It is the Joseph Campbell, like, this is when the journey begins. and then by page 90, you've entered this third act and we've come back around and so on and so forth. And while every movie is different, we understand that that's the same thing.

1:02:22And I think what's happened is that philosophy has been overused. And I think, do you remember the movie Parasite that won the Academy Award? Parasite changed it and it wasn't by page 60, 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 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 then everyone else copies that. And then you got to wait for the next genius to come along to do the thing. And I think that page one, page five, page 30, page 90 thing is completely, it doesn't work for today's audiences.

1:03:09They don't have the patience to wait till page 30 to find out when the turn is. And so in short form, there's like this new philosophy of like 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 is a world where, you know, we were exploring this idea of like thinking about the new approaches of how to tell long form stories and short form bites and things like that. And, 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 want to be like a manager meeting with VCs and boards and getting kicked out by Jack Dorsey.

1:03:46How many copies of your books have you sold? Hundreds of thousands of copies, yeah, over time. I haven't checked in a long time, but hundreds of thousands, and they've been printed all over. Dude, why is American Kingpin not a Netflix seven-part series? I can't believe nobody's an amazing show. It was okay. That movie was okay. I mean, no, it was bad. It was bad. It was bad, yeah. It was bad. I'm not going to tell you the story, but the reason it has not is because I got screwed over on the film rights deal. So that's the reason why. But it may end up, and it's still today, it still may end up there.

1:04:24We'll see. All right, if I wanted to spend six weeks 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 dedicated, you'd need more than six weeks. So let's pretend it's— What would be the first—what would be the— Well, what can I do in six weeks? I got 19 bucks. What do you got for me? If you—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 I read was when I wrote Hatch and Twitter, I really wanted it to feel like a murder mystery because no one knew what really happened.

1:05:05And 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. It's a blue book. It's a collaboration where a bunch of murder writers and screenwriters and so on each write a few chapters each. And there's a few things I learned from that, which were, which one is I, when you read a lot of books, people forget to describe smells. and murder mysteries always do. And it's like, and it brings, it really brings you in. It's wild to see how it can add like this extra layer, like sounds, smells, you know, the noises, you know, not just the creaking stairs, but the, you know, the mold, whatever it is, it just creates this sense of story in your brain.

1:05:50The other thing is the Save the Cat, which is really interesting. Even if you don't write screenplays, it's a really interesting way of understanding character and so on. And I read a bunch of screenplay books by like some of the old greats and they talk about characters 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 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.

1:06:22And it's like what they don't realize is that some of the greatest things that they will learn is from things that have nothing to do with what they do. So I'm 48 now. When I was 45, I loved listening to piano music. I've never played before. I was like, you know what? I'm going to learn the piano. 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, all right, the cover. That says like a New Year's resolution. This is my pre-year mission. How are you doing? Well, I'm on the Faber method here. So I'm on book 2A right now. I'm playing.

1:07:03I'm playing. There's a great app. It's like, it's called, that I do in my spare time. It's called Notes Teacher. And you just do it for like five minutes a day. It's like 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 they are telling a story. And they're telling a story, you know, Hans Zimmer says like the notes will ask a question and then the next notes will answer the question.

1:07:37And it's like, and the way Chopin like is 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 amazing. And it started to kind of inform some of the ways I thought about screenplays. And, like, I read as many novels as I can. I hate nonfiction books. I can't read nonfiction books, which is funny because I write them. They're just boring to me. But I read novels, and I love, like, just studying as I'm reading, like, oh, that was really unique of the way they did this. And I read a lot of like 1950s sci-fi and then I read a lot of like 1930s, 40s, 50s, 60s incredible, you know, like the writers that we all should read.

1:08:22And you just understand that they, it's really, these stories are about people, not the stories that we think that it's like the guy who wrote Game of Thrones, George R.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 what ends up happening is as you watch something, the best stories are the ones where you imagine yourself as the character.

1:08:56And then you want to know how you would solve the problem. If I'm James Bond, how would I get out of this as the drill is about to, you know, sever my heart or whatever. And then you can't figure it out and the storyteller does. And you're like delighted by that because it's great storytelling. I think that's your secret, by the way. You're like, nonfiction is usually pretty boring, but yours aren't. And I think yours aren't because you consume so much content that's, you know, on the mystery side. Yours are page turners. And so, you know, that lateral thinking where you take a skill from one discipline and apply it to another that usually doesn't have it.

1:09:32That's what some of the best business people do as well, is they take the best hedge fund renaissance is because they took the best AI, machine learning, mathematical prowess and applied it to finance. And we had Mike Posner on the podcast, and he was talking about how he started as a rapper, but all his hit songs are him singing. And he's not the best singer, but he's like, I am the best writer. 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 is rarely done.

1:10:15But it sounds like you've kind of done that same thing. No, I think it's totally true. And look, I think Jobs did this thing where computers back then And we're these nerdy like circuit boards. And he was like, oh, I'm going to marry graphic design with technology. And so for me, like I want to marry the style of a novel with a narrative nonfiction story. And, you know, there's great writers who've done that in the past that I have 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 bummed. I'm like, oh, I was so like in love with like reading this and I was looking forward to finish or I was looking forward to like I would sneak off to like find the page and see if I can just like read a few chapters.

1:11:00And I felt bummed that like I was like in this relationship with this book and it's over now. 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 20 or 30 books like fills that need. I think Mastermind was another great book that was a similar topic. and 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 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 bummed about it, you know?

1:11:34And so who do you view as a peer or someone you look up to where they do your style of nonfiction storytelling? Well, just real quick on the novel. Like, yes, they're not real, but they are based on reality. Like every novelist pulls from the people around them to create the characters that you're reading. So, you know, it's like, you know, if you go do research into like whatever your favorite book is, your favorite novel, like, and you look at how they did it, if they talk about it, they're like, oh, you know, when I was a kid, my grandfather used to tell me the stories about da-da-da-da-da, or like there was a neighbor across the street.

1:12:13So I think they are, it is real and it's still people. As far as people I admire and I look up to, like I said before, I don't really read a lot of narrative nonfiction. Sorry, a lot of nonfiction. I don't think there's that. And I love, I have such admiration for people's reporting and even the writing, but I need a story. I can't have it. that's what I'm describing I want more like story driven I need a story this is the shit man I just love learning about this stuff you had one last question Sam and I interrupted you or did you answer it? well it was about Sean did you see the documentary on Netflix about what was it called with Ilya was it Bitfinex what was that called?

1:13:02it was the couple Bitcoin Bonnie and Clyde I did a documentary on them for Netflix with Chris Smith who did Tiger King that was about this couple that had stolen 5.4. Well, they stole$72 million in crypto and then were trying to launder it. They were the only two people on the entire internet who wanted the price of Bitcoin to go down. And every time they were trying to launder it, it would double and double and double and double and double to the point that at one point at its peak it was worth$8.4 billion. And she was this wacky cringe rapper and he was like a part-time magician investor. And like, it's one of those stories.

1:13:41If it were fiction, you'd be like, yeah, this is stupid. This would never happen. She, the guy, Ilya, spoke at the very first HustleCon, which is kind of funny. Oh. And then the woman, Heather. You're the new Forbes 30 to 30, dude. You spot him. 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 she was kind of a sex freak. I had a bunch of friends that fooled around with her. And they were like, this woman's wild, man.

1:14:12You should stay away. Like those types of stories. And I was joking with Nick. I was like, whoever I guess we interact with, just maybe 10 % of them are going to end up becoming amazing criminals. Because for some reason, we've been around a bunch of these people right as or right before they were committing some huge crime. But that was also a good story. Yeah, that was a great story. That was such a wild story that they went to Ukraine and had fake passports. I mean, it was just, yeah, it's nuts. Is making a Netflix documentary, is there good money in that? Or you do it just because it's sick and it's like, it's art and I'm doing this for art?

1:14:52How does that work? There's not. Look, being a writer, I think it's good money if you can pull it off. Somebody sent me an article a while ago that you're more likely to become a billionaire than to become a successful writer. And, yeah, it's like I think the way in the olden days, you know, at Vanity Fair, for example, 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 then they had the house upstate and the brownstone in Brooklyn, and it was a different time. And now, you know, everything's been diluted.

1:15:31Media has been completely diluted where we have podcasts and blogs and newsletters and mainstream media and all this stuff. And so the advertising dollars and the revenue dollars, it's not like they've gone up. It's just they've evenly been more evenly distributed. And so for me, I just want to tell stories 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 then it all just kind of adds up from there. I could talk with you for hours, man. Thank you for doing this. Thank you so much for having me.

1:16:09This has been really fun. We appreciate you. All right, that's it. That's the pod. That's the pod. I feel like I can rule the world. I know I could be what I want to. I put my all in it like no days off. On the road, let's travel, never looking back.

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