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We Talk to the Guy Who Knows Silicon Valley’s Darkest Secrets

My First Million

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  • Silk Road Story
    • Nick Bilton’s book, American Kingpin, details the rise and fall of Ross Ulbricht and the Silk Road.
    • Ulbricht, a seemingly ordinary individual, built and ran the largest online drug marketplace. Transcript: Nick Bilton On the road, let’s travel, never looking back. Sam Parr All right, 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 Kingpin. It’s a story of the Silk Road, of Ross Ulbrecht, who created it, grew it to great 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 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 he’s here with us today on MFM. So let’s do it. Shaan Puri Nick, what’s going on? We wanted to talk about all types of stuff. We want to talk about storytelling. We want to talk about things that you researched that didn’t make the book. We want to talk about like the OG stories of Silicon Valley because 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. Nick Bilton This is exciting. This is fun. It’s going to be great. We’re going to tell some some crazy stories. I’ve got Steve Jobs stories. I’ve got Jack Dorsey stories. I’ve got Russ Ulbrich stories. You name it. I got them. Shaan Puri Who of all those people? Have you become friends or admire any of them? Or are you like a strictly like a journalist who doesn’t cross the barrier? Nick Bilton Well, that’s a great question. 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 kind of friends with. But let’s save that for when we get into the hatching Twitter, Elon Musk, Jack Dorsey territory of this pod. Shaan Puri I was listening to an episode with David Perel. It was all on writing. And you talk about like what makes a great story. And this sounds like a backhanded compliment. I think that your writing’s amazing. Your storytelling is amazing. I think you just happened to pick the best story of all time with the Silk Road. Nick Bilton Like it was like set up to win. Well, I think I mean, let me just tell you how I came to the story. So I was a reporter at the New York Times and in Silicon Valley covering tech. I was writing about Apple and Facebook and Twitter. And I don’t even know how to describe this moment in time. You know, it was like 2008, 2009. It was, you know, right after the bubble had popped, the second bubble. And it was again, once again, this no fly zone, you know, to be in Silicon Valley to do startups and whatnot. And I started covering 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 Dorsey and all these guys. And I wrote the Twitter book, which we can talk about, and there’s incredible backstories to that, and of people 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 I couldn’t, you know, I really, I love writing books. It’s one of my favorite forms of writing to do. And I heard about this guy who had started the Silk Road, who’d been arrested at this little public library that was like four blocks from my house. And I knew the library. I knew this, and I knew the area, and I also knew the Silk Road. And so I wrote a piece for the New York Times about it. It’s like a short piece. And then I was like, maybe there’s a book in this. And as I started to dig further and further, it just felt undeniable. It was like, it was just an unbelievable story of this kid who, a kid because he was very young at the time. But he got he grew up in Austin. He was incredibly smart. Sixteen hundreds on his SATs, you know, studied astrophysics, went off to one of the best schools and and then had this like libertarian idealism to him. Is no different to like Travis Kalanick when he’s building Uber and, you know, all these other people in Silicon Valley. And he decides that drugs should be legal 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 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 the secret browser that you can, where the dark web exists. And then he takes Bitcoin, which 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 making millions and millions and millions of dollars a day as the biggest drug dealer on the Internet. By the way, how good was the branding for that? Shaan Puri 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 it was pretty brilliant. Nick Bilton No, the branding was great. There was I forget the name. There was a name that he had originally wanted to call. It was like some terrible name. Shaan Puri It was called like Hardcore Underground or something like something where it was like this doesn’t sound like a piece like i’m interested in that but what’s what’s fascinating is you Nick Bilton Know at the time he’s living in austin he’s got this girlfriend julia and they’re kind of in this like toxic relationship and he has this business and it’s like a it’s a 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 and it all kind of you know it all comes together in this very, very unique way. What ends up happening is Gawker, the website that is obviously now defunct, 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 trying to hunt down the Dread Pirate Roberts. And Ross essentially goes on the run around the world as they’re trying to catch him. Sam Parr 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 knew some of his thoughts, But it’s like, 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, you know, has sort of tried, but hasn’t really made it yet doing anything. And then you’ve got his girlfriend, and there’s that part of it. They’ve got the libertarian ideals. And then it leads to, you know, the thing escalates like crazy where, I think, I don’t know if it’s peak, but I think Silk Road was doing like, you know, over a billion dollars, like GMV Through the marketplace. And there’s like, you know, murder for hire plots going on. Like it escalates like the craziest crime movie would escalate. But I like that you had that beginning part where it wasn’t just this criminal mastermind. (Time 0:00:12)
  • Immersive Research
    • Immerse yourself in your subject’s world to understand their perspective.
    • Visit the places they frequented to capture sensory details and enhance your storytelling. Transcript: Sam Parr It was like this smart kid, you know, just trying to do something and had a certain set of ideals. How did you know what he was thinking? How did you get access to his diary? How does a writer like you get that? And you got a lot of stuff. You got the footage of the library where he got arrested. You got the chat logs with the government. How did you get access to all this information? Nick Bilton Well, I can’t tell you exactly how I got a lot of it because that’s the that’s investigative reporting. And and I, you know, obviously can’t divulge where it came from. But the way I approach these stories is I want to know everything, literally everything. And so I have these researchers who work for me. And one of them, one of them actually used to do oppo research for the for the Democratic Party trying to find you know bad stuff on republicans and um 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’m reporting it what’s been interesting is i have this new project That we’re doing and we’ve been using lm google lm’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 spreadsheets And databases and like, it was very, very complicated the way we did it. But we kind of put into three tranches. So we have the Dreadpire Roberts and we get access to the chat logs that were on his laptop, 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. And then there’s some diary entries. He’d literally been making a diary about the thing because the best line ever is he thought there’d be a book written about his life one day. And then we go through social media and we get all the photos and all the posts and all that. And everything’s on a timeline. It’s all got timestamps. And then lastly, it’s the interviews with everyone. And as far as like, you know, we reach out, we get yearbooks and you go and you find out everyone he went to elementary school with, the middle school and high school, and you interview Everyone. You find the neighbors, the kid that lived across the street, you know, which coffee shop he went to, you go to the coffee. And then the thing I do, which is a little psychotic, but I do it anyway, is I want to be able to describe what the, 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, there was one instance where he went camping. And, and so I didn’t know where the campground was. It was near San Francisco. But he had taken two pictures, three pictures, sorry. One was when he left, and 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. And we could tell the timestamps, so we just did the math, and we’re like, okay, it’s probably 45 to 50 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 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 smell everything. And so I can describe because it hasn’t changed in in six months or a year it 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 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. (Time 0:06:58)
  • Motivations for Talking
    • People are motivated to talk for various reasons, from wanting recognition to needing catharsis.
    • A reporter’s skill lies in understanding these motivations and building relationships with sources. Transcript: Shaan Puri Another podcast, you spent like three or four weeks with Julia Ross’s 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 kind of shut up. But you knew stories like, you knew like when they had sex or 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 heard you spent time with her, like getting info. Why on earth would some of these sources talk to you? Why wouldn’t they just say, I don’t need that in my life. Get out of here. Nick Bilton I think one of the things I’ve learned as a reporter for two decades is that people want to talk for different reasons. So there’s endless numbers of them. And one of, I think, people think being a reporter is like, you’ve got to break the news and you’ve got to write the story. It’s like, no, it’s relationships. It’s like it is literally just relationships. 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. And so, for example, everyone has a reason. So people that would leak stuff to me that worked at Apple or Facebook, 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, or like they have other egotistical reasons, whatever it is. And so your job as 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, what can I say to you? What is it that you want? I know you want something. We all want something. Part of the story. And I think she wanted to be famous a little bit. And I also think that she, for her, there were, there was some things that hadn’t been said and hadn’t been finished and, and that she hadn’t, it was like a little bit cathartic, I think, In some respects. (Time 0:12:30)
  • Dorsey’s Disapproval
    • Jack Dorsey actively tried to suppress Nick Bilton’s book, Hatching Twitter.
    • Bilton faced pushback but maintained the story’s integrity by having recorded interviews. Transcript: Shaan Puri Did you ever feel in danger during your research? Nick Bilton I felt more in danger doing the Twitter book, quite honestly. What was the danger there? The powers that be didn’t want? Jack Dorsey did not want that book out. And he was trying to do everything. Sam Parr Dude, 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. Nick Bilton No, it’s all a story that he tells. Look, there are definitely stories I’ve worked on. I wrote a book that I chose not to publish. It was just about the NRA. This was after Marjory Stoneman Douglas had happened because I went to school there. And I spent a couple of years on the book and then decided to not do it for a few reasons. But that one, I wouldn’t even say that was, I wasn’t like afraid someone would come after me, except maybe like some gun nuts later. You know, I’ve done some stories, mafia stuff, like Russian hackers, things like that. And I’ve never, you know, I think a lot of the times people respect the process and they don’t want to start a war with the New York Times or Vanity Fair or, you know. Right. I think it’s different if you’re like covering Mexican cartels in, you know, in Mexico. That’s a whole different thing. Or if you’re trying to be a reporter in Russia or something like that, that’s where you really do have to start to worry. But in Silicon Valley, it’s a bunch of nerds that, you know, talk a big game and that’s it. I do have one story, but it’s from the Twitter book. So when I, I won’t mention names here, but when I wrote the Twitter book and there’s a moment in the book where 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 bunch of people, these like crisis PR people that are trying to, 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, uh, heard you’re calling everyone and saying, and she’s like, I didn’t say that. And I was like, I said, look, I have the tapes of the interviews and 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 that was the end of it. So, you know, so there are these moments where you get these crisis comms people that come after you, but. Well, you (Time 0:16:46)
  • Knowing the Subject
    • Thorough research allows writers to understand subjects better than they understand themselves.
    • This deep understanding can reveal untold stories and hidden motivations. Transcript: Sam Parr Know, when you do as much research as you do, you end up getting to know the subject in some ways better than themselves. It’s like in business, you know, CEOs will pay for these expensive 360 reviews where somebody goes and talks to their wife and their coworkers and their interns, and they come back with This feedback, and it’s supposed to be this eye-opening thing about them. This person can find out more about them and show them a mirror that they haven’t really seen before. In that case, they want it. But when you’re researching Jack Dorsey and you say something like, you know, that’s all a story, who’s the real Jack Dorsey? Nick Bilton Well, I think just one thing about what you just said is I know, somebody asked me once, how do you know when your book is done? When you’re like, when you’re ready to, because 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 different colors and everything And put them up on a wall and um and uh and i know 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 and there was a moment where I told Evan Williams something that had happened behind his back that I thought he knew about and 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, the best quote I ever got about Jack Dorsey, and I’ve written a lot about him, was from one of the board members years ago who said the best Product Jack Dorsey ever made was Jack Dorsey. Because that’s what it is. Everything is a story, right? Every single solitary thing we do every single day is us telling a story. The outfit you chose to wear today is a story about yourself. Me telling a story about the book is me. 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 based on how they want us to perceive us. And I think that people like Jack and Jobs and Bezos, all of these guys and Zuck, that’s one of the things they’re great at is telling a good story. And I think like I personally believe that your story for a company is 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? What’s (Time 0:19:17)
  • Glass’s Lack of Compensation
    • Despite his wealth, Jack Dorsey didn’t compensate Noah Glass for his contributions to Twitter.
    • Bilton criticizes this lack of acknowledgment and financial recognition. Transcript: Sam Parr You don’t like him or you just feel like that’s a wrong that needs to be righted, that story? Nick Bilton Yes. You want to correct the record? I don’t like people who fuck other people over, especially their friends. Shaan Puri Did you find yourself—you had this great podcast with our friend David Perel, and you said a line that Hitchcock, someone came up with, where it was, every villain has a mother. And it was like, I guess like you see yourselves in the villain at times. That’s what good stories do. You kind of like like a villain a little bit or they’re a little… You know, you’re interested in them. Did you find yourself liking Ross? Did you find yourself liking Jack at times? Because 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? Nick Bilton 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? Sam Parr How’d you meet him? Nick Bilton Oh, just at this, at a rally once, years and years and years ago, I think 2015 or something like that, you know, spent time with Elon. Like he’s kind of funny. He’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 they all have this, there’s something to them that is enticing. And Jack’s funny. He’s a funny, nice guy. Like when you’re hanging out with him, it’s like you’re like, oh, he’s fun. I like hanging out with this guy. 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. 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. You 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, go take care of him. (Time 0:29:30)
  • Jobs’s Reality Distortion Field
    • Steve Jobs used a “reality distortion field” to manipulate narratives.
    • He convinced Nick Bilton to alter a story, even denying previous statements. Transcript: Nick Bilton 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. So I was a, I would, 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. And so I end up doing that. I do page layouts and stuff like that. And when you do these, the way these meetings work is 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 going to 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? And 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 to them. 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, 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. And she was like, I don’t feel that from you. And I’m grateful. It’s so grateful that she, 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 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 have I done? 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 bylines That you were just like, holy shit. And 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? 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? I 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, 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. You call and you say, hey, I’m doing the story on this. Do you have a comment? And the PR woman that answers, she says, Steve’s going to call you. And 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, wants to talk to you. And I’d been writing a lot of Apple stuff. And, um, and so he never called. And that night I went out for dinner, uh, with my girlfriend at the time. And, and we went for sushi and I 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 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 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, 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. I, I played this conversation back in my head and I was like, holy shit. He 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. Sam Parr 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. 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. Is it just his aura? Is it his gravitas? Is he really good at reframing things? Is it intimidation? What is he actually doing? Shaan Puri And it’s one of those things where you hear about and you’re like, that won’t happen to me. No, exactly. Nick Bilton 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. But 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 (Time 0:33:26)
  • Bezos’s Initial Impression
    • Nick Bilton believed Jeff Bezos “had it all” – success, family, and positive work culture.
    • Bezos’s later divorce and lifestyle change challenged this perception. Transcript: Nick Bilton Are there any of these guys that you felt like had it all? Sam Parr Meaning they have the extreme success, they’re the extreme achievers of society, but most of the time you look and they’re on their fifth wife and the story is that they’re, 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. 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 human being to be around. Yeah, people who you would say, they’re winning. Nick Bilton 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, along the people that I really, really admire and like and I think are good people. But 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. And David used to smoke outside and I would go down and like hang out with him. And he said, 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. And the stewardess was like, we are not allowed to take off, sir, until you turn it off. And I was like, it’s a calculator. Like, it’s not going to destroy the plane. And she got very terse. And I was so angry that when we finally got up to I wrote a column about just how ridiculous it was. And it got published like the next day or 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. So 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 they 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 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. And, um, and 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, cause it helped his business, of course, You know? And, um, anyway, I ended up meeting with him, uh, and, um, and 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, 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 going to a dinner at his house and, um, uh, and he, you know, talking about his family and like, and I met his wife, Mackenzie many times. And, and I was like, oh, this, the guy who has it all. He’s created this unbelievable business. From what I could tell, 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, uh, and then they got divorced and he ended up, uh, in a very, very different relationship. (Time 0:43:15)
  • Jobs and the Waitress
    • Steve Jobs berated a waitress for serving pulpy orange juice, demanding perfection in her role.
    • This anecdote highlights Jobs’s demanding nature, even in trivial situations. Transcript: Nick Bilton So I, um, 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 do you want me to tell that that walter isaacson oh yeah yeah go ahead so walter told me the story of after the ipad where he had met jobs in the four seasons I think was, which is connected to the Moscone Center, and they 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, again that’s got pulp in it and he just becomes more and more angry and about this orange juice and at one point it sends and she’s almost in tears it’s like This this poor waitress and at one point um Walter says like Steve what 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 squeezed, 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. And 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 (Time 0:47:57)
  • State of Media
    • Most media is garbage, but some journalists strive for investigative reporting.
    • The rise of the internet and changing media landscape diluted journalistic integrity. Transcript: Sam Parr And there was these people who were, you know, you recognize their names from the bylines that you had just like so much respect for them. Do you think that that’s still like, does that shit matter at all anymore? Because for me, I’m like, if I’m a founder of a company now, I don’t, I put $0 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 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. I just feel like the credibility has gone down. But I’m also on the outside. You’re from that world. Do you feel the same way? Or do you think that’s completely misguided? Shaan Puri There’s a practical thing of like, you can get an audience on Twitter, on wherever, and you’re like, I don’t want you, nor do I need you. Nick Bilton 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. And I met those people. I remember those people at the New York Times when I first started. And I had, they were, you know, they were people that were making $120,000 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 that does that include everywhere yes 1000 because i think because the system it all broke like it’s broken and i i believe it’s broken Beyond repair for now 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 when I first started at the times, like you weren’t allowed an opinion. You weren’t allowed, there was no, you know, you, there was no social media. Like 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, 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 and 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 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. I barely graduated high school. Like I literally had a 2.1 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. 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 that was – they were the internet people. They hadn’t been mentored. 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 going to be irate because we do. That is not the way the world works. The 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, 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. And 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. 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 point of view, 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. (Time 0:51:46)
  • Improve Storytelling
    • Read diverse stories, including novels and screenplays, to improve storytelling.
    • Studying different storytelling structures can enhance your own writing. Transcript: Sam Parr 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? Nick Bilton Well, if you dedicated, you’d need more than six weeks. Sam Parr 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… Nick Bilton 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. 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. 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, 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. The 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’ve 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. And 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 love 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… Shaan Puri That’s like a New Year’s resolution. This is my year mission. How are you doing? How is it? Sam Parr Well, I’m on the Faber method here. So I’m on book 2A right now. I’m playing. I’m playing. Nick Bilton 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. And 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, 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 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. And 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, and 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. Sam Parr 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 on the mystery side. Yours are page turners. And so 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. 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. (Time 1:03:37)