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

Nick Bilton

I've got Steve Jobs stories. I've got Jack Dorsey stories. I've got Ross Ulbricht stories. You name it, I got them.

Shaan Puri

Alright, Sam has been telling me about a book for probably ten years in a row, and I finally got around to reading it this year. The book is *American Kingpin*. It's a story of the Silk Road and Ross Ulbricht, who created it, grew it to great prominence, and ended up going to jail for what we thought was for life. Then he just got pardoned by Trump. So, Sam just reread the book, I read it this year, and we both love this thing. It's a page-turner! The author, Nick Bilton, not only wrote that but he also wrote *Hatching Twitter* and a bunch of other stuff. He's a fascinating guy, and he's here with us today on MFM. So, let's do it!

Sam Parr

Nick, what's going on? We wanted to talk about all types of stuff. We want to talk about storytelling, things that you researched that didn't make the book, and the OG stories of Silicon Valley. You've been covering this stuff forever, but you're like one of the three people we've had on the pod that I'm nervous to talk to. I stayed up all night reading everything about you.

Nick Bilton

Don't be nervous! This is exciting, this is fun, it's going to be great. We're going to tell some crazy stories. I've got Steve Jobs stories, I've got Jack Dorsey stories, I've got Ross Ulbricht stories. You name it, I've got them!

Sam Parr

Who of all those people have you become friends with or admired? Are you strictly a journalist who doesn't cross the barrier?

Nick Bilton

Well, that's a great question. I feel like we should save that answer because I've got such great stories about all these people, about Bezos and everyone. There are some that I have become friends with and then unfriended, 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 podcast.

Sam Parr

I was listening to an episode with David Perel. It was all in writing, and you talked about what makes a great story. This sounds like a backhanded compliment, but I think your writing is amazing. Your storytelling is amazing. I think you just happened to pick the best story of all time with the Silk Road. It was set up to win.

Nick Bilton

Well, I think I should tell you how I came to the story. I was a reporter at The New York Times, covering tech in Silicon Valley. I was writing about Apple, Facebook, and Twitter. I don't even know how to describe this moment in time; it was around 2008 to 2009, right after the second bubble had popped. It was once again a no-fly zone to be in Silicon Valley, to do startups and whatnot. I started covering these companies, and the idea of one of them becoming a trillion-dollar company was just ridiculous. That would never happen. I would spend time with Steve Jobs, Bezos, Zuck, Dorsey, and all these guys. I wrote the Twitter book, which we can talk about, and there are incredible backstories to that, including people trying to kill the project and so on. After finishing the Twitter book, which had done really well, I was looking for a new book idea. I love writing books; it's one of my favorite forms of writing. I heard about a guy who had started the Silk Road and had been arrested at a little public library just four blocks from my house. I knew the library and the area, and I also knew about the Silk Road. So, I wrote a short piece for The New York Times about it. Then I thought, maybe there's a book in this. As I started to dig further, it felt undeniable. It was an unbelievable story about this kid— I say "kid" because he was very young at the time— who grew up in Austin. He was incredibly smart, scoring 1600 on his SATs, studied astrophysics, and went off to one of the best schools. He had this libertarian idealism, similar to Travis Kalanick when he was building Uber and other people in Silicon Valley. He decided that drugs should be legal and that the government should not be able to tell you what you can and cannot put in your body. He believed the only reason drugs lead to deaths and murder is because the government has so much control over them. So, he took the Onion Router, which is the secret browser where the dark web exists, and he took Bitcoin, which both emerged around the same time. He created a proof of concept with a website called the Silk Road. Next thing you know, he was making millions and millions of dollars a day as the biggest drug dealer on the internet.

Sam Parr

By the way, how good was the branding for that? The fact that he called himself "The Dread Pirate Roberts" and the "Silk Road"—the logo behind it, the branding was actually like the whole thing. 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. It was like some terrible name.

Sam Parr

It was called something like "Hardcore Underground."

Nick Bilton

It was.

Sam Parr

I'm interested in something where it doesn't sound like a "P."

Nick Bilton

But what's fascinating is, you know, at the time he's living in Austin. He's got this girlfriend, Julia, and they're kind of in this toxic relationship. He has this business, and it's a pretty nice business where he goes around and collects books that people want to get rid of, and then sells them and mails them out. So when he moves into the drug trade, he goes to Bastrop State Park, rents a cabin, and grows mushrooms so that he can sell drugs there to show that you can sell drugs. Then he starts mailing them out, just like he's mailing the books out. It all kind of comes together in this very unique way. What ends up happening is Gawker, the website that is obviously now defunct, writes about it. And then that's it. It's like game over. Everyone on the planet knows about it, and senators are coming after him. 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. Ross essentially goes on the run around the world as they're trying to catch him.

Shaan Puri

Yeah, it's one of the best things about the book. 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. You know, he 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 got the libertarian ideals, and then it leads to, you know, the thing escalates like crazy. I think, I don't know if I'm at its peak, but I think Silk Road was doing, like, over a billion dollars in gross merchandise volume (GMV) through the marketplace. Yep, and there's, like, murder-for-hire plots going on. 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. 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? Why does a writer like you get that? You got a lot of stuff. You got, like, the footage of the library where he got arrested. You got, like, the chat logs from, you know, 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 investigative reporting, and I obviously can't divulge where it came from. But the way I approach these stories is I want to know everything—literally everything. I have these researchers who work for me, and one of them actually used to do opposition research for the Democratic Party, trying to find, you know, bad stuff on Republicans. We literally just blanket approach it. What's been really interesting is I have a new project, which I can't talk about, but I can tell you a little bit about how I've been reporting it. We've been using LLMs (Large Language Models) and Google’s LLMs notebook. Now, we stuff millions of words into these things, and I can just query it. Whereas before, we had to build Excel spreadsheets and databases, and it was very complicated. We kind of put it into three tranches. First, we have the Dread Pirate Roberts, and we get access to the chat logs that were on his laptop. I don't actually know if he knew they were there because they were in a hidden folder. I don't think he actually knew he'd been saving them, or maybe he was—I don't know. Then there are some diary entries. He'd literally been making a diary about the thing because he thought there'd be a book written about his life one day. Next, we go through social media to gather all the photos and posts. Everything's on a timeline; it's all got timestamps. Lastly, we conduct interviews with everyone. We reach out, get yearbooks, and find out everyone who went to elementary school, middle school, and high school. We interview everyone, find the neighbors, and even the kid that lived across the street. You know, we go to the coffee shop he went to. The thing I do, which is a little psychotic, but I do it anyway, is I want to be able to describe things in a way that makes you feel like it's a novel in some respects, but it's all real—nothing's made up. For example, if I know he took a picture somewhere, there’s one instance where he went camping. I didn't know where the campground was; it was near San Francisco. He had taken three pictures: one when he left, and we could figure out the street because we could see the angles and the street signs. The next was when he was driving over the Golden Gate Bridge, and the third was when he got to the campground. We could tell the timestamps, so we did the math and figured it was probably 45 to 50 miles away. Then we looked in a circle around San Francisco and found different campgrounds. I went to one, and there we were—the campground. I go there and find the spot where he took the picture. I sit in that spot, and I can smell everything. I can describe that because it hasn't changed in six months or a year; it still looks the same. I do that with everything. I go to the coffee shops he goes to, I walk the same streets, and then you get to describe this. You can also use different apps to see how the sun comes on certain days, and you can describe what the shadows look like. You just can describe everything.

Shaan Puri

Sam, isn't this wild? It's wild in two ways. One, it's the same sort of obsession as why Jobs said, "I'm going to design... we need to finish the inside of the casing of the computer." And they're like, "Steve, nobody's going to see this." But he's like, "I've seen it. I know it's there. That's why we have to finish this inside case." So, this is a weird kind of product obsession, which I respect. But then there's also the question: dude, nobody would know. Nobody would ever know, and it might not ever matter. Why does it matter to you to do that?

Sam Parr

And it's also weird that, Nick, you've written like *Hatching Twitter* wasn't the most favorable towards Jack Dorsey and some of these guys. You guys all have the same flavor of crazy, though. You know what I mean? Like, that's what Sean's describing is like what the trades have.

Nick Bilton

Look, I totally agree. I mean, it's fun for me. I love the challenge. What's interesting is that you bring up jobs. I spent quite a lot of time talking to him when he was alive. He was incredibly obsessive. One of the things he always said, and he said it publicly too, was that you should never know that the technology exists and how it happens, and so on and so forth. I'm fine coming on a podcast and talking about how I did it, but when you're reading, I'm not going to tell you. There's nothing that drives you more insane than when it's like, "According to a transcript that I found..." Who gives a shit? Just tell me the story! I think one of the beauties of great products is when you don't know how it works. It just works, and it's magical. It's all those words they use in the ads and everything. I think the same is true for storytelling. A lot of the greatest novels—I'm a voracious reader; I read a ton of novels—have a significant amount of research behind them. For example, the amount of research that people like Gabriel García Márquez put into "One Hundred Years of Solitude" is immense. When you read these works, they're not telling you all this; they're just telling you a story. Why?

Sam Parr

Would I saw that you... I think you said in another podcast you spent like three or four weeks with Julia Ross's ex-girlfriend when he was starting it. And I didn't know that you had spent time with them. When I spent time with her, I was like, "Why on earth did she ever talk to Nick?" You know, if I'm her, I'd probably just kind of shut up. But you knew stories. You knew like when they had sex or the comments that they made to each other. I'm like, "How on earth does he know this?" Then I find out that you... I heard you spent time with her 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 talk. People want to talk for different reasons, so there are endless numbers of them. One of the things people think about being a reporter is that you have to break the news and write the story. It's like, no, it's about relationships. It is literally just relationships. What you have to do is figure out that you need these people to talk to you, and you have to figure out how to make them want to talk to you. For example, everyone has a reason. People who would leak information to me that worked at Apple or Facebook—some of them were just so excited to say, "Oh my God, I worked on this thing!" They just wanted it out there and didn't have the patience. Others worked on something that never got made, or they got messed over by their boss and didn't get the credit. They might have other egotistical reasons, whatever it is. Your job as a reporter is to try to get them to talk to you and to figure out what they want. My job is to be like, "What can I say to you? What is it that you want?" I know we all want something. With Julia, I think she wanted to be part of the story. I think she wanted to be famous a little bit. I also think that for her, there were some things that hadn't been said and hadn't been finished. It was a little bit cathartic, I think, in some respect. That's the reason she talked. When it came to the agents, I spent time with almost all of the agents involved in the case. With Jared G. Yegan, I probably spent 400 to 500 hours together. I went to his office, I went to his house, and we met in all different places. I saw the postal service where he worked, and then we went inside the Chicago airport and underneath the bowels of it. It was amazing to see all of that.

Sam Parr

Do you remember the stuff with Sean? So, Jared was the guy who wanted to be an FBI agent or something like that, but he ended up being a Homeland Security agent, which is like...

Shaan Puri

I think the book starts with him. It's like, yeah.

Nick Bilton

He's the star of...

Sam Parr

The pill.

Nick Bilton

Yeah, a single pill.

Sam Parr

One pill. What shocked me about Homeland Security and mail is that they would just sit there and watch packages come in. They would just be like, "That envelope looks weird," because it's handwritten in a certain way. It's just similar. Like, it's just so crazy that one of the few different ways he was caught was just like traditional police work, as opposed to something more complex. It was shocking that it was just like eyeballing things.

Nick Bilton

Well, it's what's interesting... I started with the pink pill, the single solitary pink pill, because there's a line in the book about how the website started with a single line of code. All of a sudden, he creates this world. What I find interesting about technology—this was just my way of telling the story—is that there's also a scene where we see a computer being built. It starts with a single diode. What I find so fascinating about technology is that all these websites, products, and companies start with this little, single thing. The same goes for books and everything else. They grow into these entities that take over the world. For me, the pink pill, the single solitary pill of ecstasy, was the beginning of the story, which was just going to become a **fucking tidal wave** that took over everything.

Sam Parr

Did you ever feel in danger during your research?

Nick Bilton

I felt more in danger doing the Twitter book, quite honestly.

Shaan Puri

What was the danger there? Those powers that be didn't want...

Nick Bilton

Jack Dorsey did not want that book out, and he was trying to do everything he could.

Shaan Puri

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

He... no, it's that... that is 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, which was about the NRA. This was after the Marjory Stoneman Douglas incident happened because I went to school there. I spent a couple of years on the book and then decided not to do it for a few reasons. But that one, I wouldn't even say that I wasn't afraid someone would come after me, except maybe some gun nuts later. You know, I've done some stories on mafia stuff, like Russian hackers, things like that, and I've never... you know, I think a lot of the time people respect the process. 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 covering Mexican cartels 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 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, there’s a moment in the book where someone gets fired. I got a call from a friend who's a journalist at Bloomberg, and they said, "Hey, there are a bunch of crisis PR people that are 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, especially this moment. It's all made up." I just wanted to let you know. So I called this woman directly and I was like, "Hey, I heard you're calling everyone and saying that." She said, "I didn't say that." I said, "Look, I have the tapes of the interviews and of that moment, and I will happily post it on Twitter. You just keep calling people and I'll put it on Twitter." And that was the end of it. So, you know, there are these moments where you get these crisis comms people that come after you, but... well, like, I don't know.

Shaan Puri

When you do as much research as you do, you end up getting to know the subject in some ways better than they know themselves. It's like in business, these CEOs will pay for these expensive 360 reviews. Someone goes and talks to their wife, their coworkers, and their interns. 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, you know, when you're researching Jack Dorsey and you say something like, "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 ready to..." Because what happens is you research 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. In my office, I have these boards, and I create these cards that you can wear. They're just all the scenes in different colors, and I put them up on a wall. 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. That's the moment I'm like, "Okay, I got it." 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. I was like, "Oh, okay, well, there you go. I'm ready." 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. We're all... it's all we're doing all day long. 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. I think that people like Jack, Jobs, Bezos, all of these guys, and Zuck, that's one of the things they're great at: telling a good story. 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?

Shaan Puri

What’s the example that drives that home?

Nick Bilton

YouTube is a perfect example. YouTube was not the first video platform; there were dozens before it. I remember seeing this when I was just a beat reporter covering Silicon Valley. My days were like office hours, and you'd have startup after startup come in to meet with you from around 2002 to 2012. Some of them had great ideas, but they couldn't walk you through them. They didn't hire a PR person, and so on. YouTube had a great story that they were able to tell, and that became the video platform. There were other video platforms that I would argue were way better than YouTube. For example, Vimeo was a thousand times a better product. It was prettier and easier to use, yet YouTube just told a great story, and Google helped them do that. That's what it becomes. If Jack Dorsey had told the real story about Twitter—that his best friend Noah Glass really was the one who came up with most of it and that he stole it from him, and that the place was a mess and no one knew what was going on, it was all an accident—you'd be like, "Oh, okay." But instead, he told the story that he was the next Steve Jobs and that he conceived of this idea of Twitter while he was in his mother's womb. It was like, "Holy shit, I gotta check this thing out! What is this?" And it's like the...

Shaan Puri

Jack Dorsey's Twitter story is interesting. I know that he grew up fascinated with dispatch, or something like that. He talks about how he loved either taxi dispatch or some transportation dispatch service. He used to listen to it, and that short-form dispatch communication was always something he was into. Then, when he had the idea for Twitter, he sketched the original Twitter concept, which he has posted before. That's the story that I know, right? Because I'm just the receiving end of that product.

Nick Bilton

So, it worked, right? That story... the story worked. Is it true? No, it's not true. Yes, he was interested in dispatch in the same way he was interested in writing poetry, painting his nails black, and dyeing his hair blue. But that's not part of the story. What really happens is, as I say in *Hatching Twitter*, and no one knew this, I had to talk to all these different people to kind of pin it together. Except Noah Glass knew it. You know, Jack was living in San Francisco. He was in his early thirties, a part-time nanny in Oakland. His life had not turned out in any way like the predestined version of Jack Dorsey we think of today. He got a job working at a ticketing booth at Alcatraz. These booths are pretty small, and he was the seat programmer who would go and fix the ticketing booth. The reason he got the job was that he was small enough to fit inside the booth and program. So, this was the life he was living. He applied for a job at Camper Shoes to sell shoes—not to build the website or be the CEO—and he couldn't get the job. One day, he was at a coffee shop when Evan Williams walked in. He had read an article about Evan and felt like it was a sign, which it probably was. The universe was putting them together. So, he sent him a note saying, "I'm a programmer." At that time, they had Odeo, the podcasting company, which was a decade ahead of its time—a brilliant idea that Noah Glass had come up with. Noah and Evan Williams had created this thing called Blogger, which was again ahead of its time. Google purchased it. One day, this guy Biz Stone reached out and said, "I love Blogger. I'd love to come work for you." So, Evan Williams and Biz became friends. Jason Goldman, who was also part of this, was working at Google. They all kind of became buddies. They ended up leaving—well, Goldman stayed, but Evan and Biz ended up leaving. The reason they left was that Evan lived on, I think it was like Eighteenth and Market or whatever the streets were. One day, he was on his balcony, and another guy, Noah Glass, was on his balcony. Noah had been reading that same article that Jack Dorsey had read. He recognized that the photo of Evan Williams was taken on the balcony, and in the background, there was little Noah Glass because they were neighbors. So, he goes out and says, "Hey, Blogger!" and they become friends. Then Noah pitches this idea for a podcast company, saying, "This is the vision. This is the future. It's going to take over radio." Evan was looking for a project, so he agreed to do it. It was all discombobulated. No one knew what was going on. They couldn't run the startup. Apple came along with podcasts, and they were screwed. Jack Dorsey came along, and they did a hack day to try to have a last hurrah to save the company. During the hack day, Jack presented this idea for Status. Everyone was kind of doing the same thing; the ideas were very, very similar. Jack presented this idea for Status, and what Status is, is stat.us/nickdolton. You go there and see my status. It's one status. If I say something in three or four words, you're not really supposed to do anything more than that on a podcast. Now, if you go an hour from now and I post a new status saying, "Taking a walk," the old podcast is gone, and it now just says, "Taking a walk."

Sam Parr

It's like an aim away message.

Nick Bilton

It's literally an aim away message that they were doing. So, Noah has a very similar idea, but he's like, "No one is going to go to stat.us/nickbilton five times." Your mom will do it because she wants to know what you're up to, but no one else is doing that. They all start bringing these ideas together. It's truly a collaboration between all of them. Noah has this realization; he's a very emotional guy and very smart. He's like, "It needs to be about friendship. It needs to be about connecting with your friends." That is what it's about. He brought this humanity to it. So, he came up with the stream and the @ replies. It's like, not just the @ replies, but the fact that you had friends. That was what Twitter was. It wasn't just status updates. There were a million other statuses back then. When it ends up becoming what it became, Noah was a mess. He was getting divorced; his life just wasn't working. He gets pushed out by Jack and Ev. Jack, who is best friends with Noah, goes into Ev's office one day and says, "Either you get rid of Noah, or I quit." As far as Ev knew, Jack could 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. But the better story is 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, I...

Shaan Puri

You seem like you don't like Jack Dorsey. Is it that you don't like him, or do you just feel like that's a wrong that needs to be righted—that story?

Nick Bilton

Is that...?

Sam Parr

Is it you want to... "fuck the record"?

Nick Bilton

That is, I don't like people who **screw** other people over, especially their friends.

Sam Parr

Did you find yourself... like you had this great podcast with our friend David Perrell? You said a line that Hitchcock came up with, where it was, "Every villain has a mother." It was like, yeah, I guess you see yourself in the villain at times. That's what good stories do. You kind of 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, you know, that you can't pull this off without the charisma. I've met Trump; he's very charismatic, very, very charismatic. You want to be around him even if you don't agree with him.

Shaan Puri

What was the context? How did you meet him?

Nick Bilton

Oh, just at this rally once, years and years ago, I think it was in February 2015 or something like that. You know, I spent time with Elon. He's kind of funny; he's a weird dude, but he's funny. You know, Jobs had this aura to him. Bezos too. 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. Jack is funny; he's a nice guy. When you're hanging out with him, it's like, "Oh, this guy is fun. I like hanging out with him." I never met Ross. I covered him in court during the trial, so I saw him many, many times but never spoke to him. They have this charisma that I think makes them great in some respects. It's not something you can learn; it's just something you either have or you don't. You cannot help but like them for that. But I think for me, I just 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. Jack is worth $12 billion, give or take. Noah Glass is worth about $0. He never got anything; he had to live off what Jack gave him. 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. To me, even if you believe that you are the creator, even if you believe that you really came up with this on your own—because he may believe that today—I just don't understand why the kid you were best friends with, who without question helped you with this product, you wouldn't take care of him. And it never happened. For me...

Sam Parr

I agree with you, but also, no. Glass now has a thing too, right? Didn't they have Olo?

Nick Bilton

No, that's a different... no glass.

Sam Parr

No shit, they're not the same guy.

Nick Bilton

Not the same guy. So, no, everyone thinks that I thought they were the ex.

Sam Parr

Thought it was like his second coming.

Nick Bilton

No, he just... he has a family. He married this French woman, and they have two kids. I think they...

Shaan Puri

Not only was Twitter stolen from him, but his own name was stolen as well. His name, which is based on Google, got stolen from him. Dude, it's taking no credit.

Nick Bilton

Mess him up.

Sam Parr

I did not know that. I thought it was like, "Oh, he's getting it back." No? Oh man, that ruined the story for me.

Shaan Puri

Can you tell us some other stories that have stood out to you? Things you still remember, either experiences or whatever. You said, "I got job stories, I have Zuck stories, I have Elon stories."

Nick Bilton

Let's see... Jobs is the best one. I think I'll do the job story. When I was a reporter at The Times, I didn't really know what I was doing. Like, no one knows what they're doing when they start out in these jobs. You pretend you do, but you don't. And I don't even think the ten thousand hours rule is accurate; I think it's about thirty thousand hours to really understand what you're doing properly. So, I ended up at The Times by complete accident. Let me just start with that story because it's actually very funny. My dream job was to be a war photographer. I'd read all these war photography books and saved up to buy a fancy camera. I would practice war photography with my friends, where they would run through the streets, and I would take pictures. I put together this portfolio. I was a graphic designer and had done toy package design for a while. I even designed the first Britney Spears doll and stuff like that. I thought, "Oh, I can use the designer job to get to The Times as a designer, and then I can become a war photographer." So, I ended up doing that. I did page layouts and stuff like that. The way these meetings work at newspapers is that you have a morning meeting where all the editors and reporters gather in one big room. Each section—business, culture, front page, and so on—pitches their stories. The editor decides which stories go where on the front page, and then off you go. I would always speak up because I didn't know you weren't supposed to. I'd say, "Well, what about this? What about that? I like that. What if you did this?" I became friendly with a lot of the editors. One day, I sat down with the photo editor, Michelle McNally, and showed her my photos. She looked through them one by one, then closed the book and said, "You're a good photographer. I think you'd be a good war photographer, but I'm not going to hire you to do it." I asked, "Why not?" She replied, "Because you're too normal. These guys are messed up; they're on drugs. They can only be in a war zone half the time. They've got something missing that they need—that adrenaline. I don't feel that from you." I was so grateful she said that. So, I thought, "What do I do now?" At The Times, I became friends with Marissa Mayer, who was talking about going over 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 a reporter because everyone wants to write for the print section; no one wants to write for the web." The words just came out of my mouth. I'd never wanted to be a writer; it had never been on my list of things to do. I said, "Well, I would do it." He was like, "Oh, well, why don't we try it?" Then I thought, "Oh shit, what have I done?" On my first day at The New York Times, I was in this massive newsroom with all these incredible people. Back then, you were just enamored by these bylines, thinking, "Holy shit!" My editor came over and, funnily enough, Twitter had gone down. He said, "Twitter's gone down; can you write a blog post about it? Call the company and everything." I was like, "Yeah, yeah, no problem." So, I looked at my computer and googled, "How do you write a blog post?" That was my first task. Then I realized, "Oh my God, what have I done?" I found myself in this job that I just didn't know how to handle. I spent weeks reading every byline of the greatest reporters. I thought, "Okay, this is how they write the intro, this is how they do the quotes, this is how they do the nut graph." I figured it out and made mistakes, but that was my foray into it. About six months to a year into being a tech blogger for The Times, I reached out to Apple. You know, you call and say, "Hey, I'm doing a story on this; do you have a comment?" The PR woman who answered said, "Steve's going to call you." At the time, there was a guy named Steve Dowling, who was a very senior comms person. I thought, "Oh cool, Steve Dowling." But she said, "No, Jobs." I was like, "What?" I asked, "Is that normal? Does that happen?" She said, "Sometimes. He's going to call you; he wants to talk to you." I had been writing a lot about Apple, and he never called. That night, I went out for dinner with my girlfriend at the time, and then we went for sushi. I had a few sakes, and then all of a sudden, I got a phone call from a number in San Jose. I answered, and it was Jobs. I was a little tipsy, and he talked to me for like an hour. He just convinced me not to do the stories the way I had been doing them. It didn't make any sense, but he made so much sense. He said, "Oh, well, you got this wrong and that wrong. If you actually look at this, you can do..." The next day, I wrote the piece. A couple of days went by, and you know when you've seen a movie, and then all of a sudden, you process it, and it's like, "Oh, that makes sense?" I played that conversation back in my head and thought, "Holy shit, he convinced me not to do the story. That was the right story."

Sam Parr

He got you.

Nick Bilton

He got me. So, John Markoff, who is a veteran reporter, I told him about it, and he just said, "It's the reality distortion field." I was like, "What's that?" He goes, "Jobs invented it." Every time I would talk to him, from time to time, it was the same thing. 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.

Shaan Puri

How does the **reality distortion field** work? I've heard that so many times, but I've 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?

Sam Parr

And it's one of those things where you hear about it and you're like, "That won't happen to me."

Nick Bilton

No, exactly. I was... I, 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, 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 could be a real asshole. Like, Walter Isaacson told me this story once. Jobs was presenting the iPad, and what they did back then— they don't do it as much anymore because the media has changed so much— was they would go around to all the newsrooms around the country. 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. Presidents would do it too. You know, you would sometimes get invited. They'd be like, "You know, Bush is here," or "The Secretary of State, like, come in." At 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 hundred and fifty years, and business people, and so on. So we got a call that Jobs was coming, and there were 20 of us that were invited to this thing. I ended up getting sat next to Brad Stone, who now runs Bloomberg Business, and Jobs was right next to him. Brad was the Apple reporter at the time, and I was the tech blogger. There was this moment where he brings an iPad prototype, and you know, we're playing with them and everything. I was prodding it too hard, and he was like, "Stop it! You're hitting it too hard, Nick." I was like, "Okay." But then he says, "This is another reality distortion field. This actually will make more sense." We were doing questions and answers, and everything. Then I said to him, "Steve, I saw you a couple of years ago at Cupertino. You were sitting on... there were three stools on stage, and you were on one of the stools. You had just presented the Apple television box." 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 then you said Apple TV will be the fourth leg, so the stool will become a chair." Something like that. I remembered it verbatim back then. He goes, "I never said that." I was like, "No, I'm... you... no, you said that. I'm pretty sure you said that." And he goes, "I never said that. I've never said that about Apple. Apple television is 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. Did you say that incorrectly?" And I'm sitting there with all the editors in the big mockas at The New York Times, 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." I was like, "Okay." And then I just shut up. 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. So what was I gonna do? Go run around to the 20 people in that room and tell them to say that he made it up? No, he did what he did, and it worked. They all believed that that was just an experiment.

Shaan Puri

Right, are there any of these guys that you felt like had it all? Meaning they have the extreme success; 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... the stories are that they're kind of an asshole to work for or that they screwed somebody over or whatever, right? They have the same as this quote: "Show me a great man and I'll show you a bad man." Right? You know, 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."

Sam Parr

Yeah, people who you would say are winning.

Shaan Puri

Yeah.

Nick Bilton

There was one person, and I say "was" because there are other people. Look, I think there are really good people in Silicon Valley. They're not the most successful, like, you know, they're not worth hundreds of billions. I love Aaron Levie; I think he's a great guy. Then there's Dennis Crowley, you know, the longest people that I really admire and like. I think they are good people. But there was one person that I was like, "Oh, you have it all." I had met him because I'd done a series of stories on the Kindle, and it was Jeff Bezos. I remember spending time with Bezos. 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. He was the media columnist, and he's since passed away. But he was everyone's mentor. He would make time for anyone. He was just a lovely, lovely person—so smart. When I became a columnist, I didn't know what the hell I was doing. The first few columns I wrote, I was like, "I don't know what the hell I'm doing." David used to smoke outside, and I would go down and hang out with him. 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 2011, and I was reading a book on my Kindle. I had like three pages to go, and I was like, "Oh my God!" They were like, "You must turn off your devices now and put them in airplane mode." I wanted to finish, so I was hiding the book to finish it. The stewardess was like, "We are not allowed to take off, sir, until you turn that off." I was like, "It's a calculator; it's not going to destroy the plane." 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. It got published the next day or whatever, and it was like the most read thing in The New York Times for weeks. I was like, "Oh, I'm picking this fight." So, I started going 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 things. So, we got all these things.

Sam Parr

Sean calls it "going to Pedicorp."

Shaan Puri

Yeah, you took one to Pedicorp.

Nick Bilton

Yeah, I was in Pedicore, and we went to these testing facilities. We did EMP testing, and we put a Kindle in these amazing giant rooms. You just have a device that can test all the EMPs. It turns out the Razer puts off like a hundred times more EMPs than a Kindle. So, I just kept writing these stories because people were so irate about the fact that they couldn't read their Kindle or play on their phone while they were taking off. Eventually, it got overturned, and Bezos, during his earnings call that quarter, was like, "I want to give a shout out to Nick Bilton," because it helped his business, of course. Anyway, I ended up meeting with him, and he was so smart and thoughtful. You could tell he was on a different level. You could just see, like, "Oh, this is someone who never forgets anything." He was married and talked about his kids, how his teenage son still sits on his lap. Then I ended up going to a dinner at his house. He was talking about his family, and I met his wife, MacKenzie, many times. I was like, "Oh, this is 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 loved working for him and stayed at Amazon for years, loving the culture. Then they got divorced, and he ended up in a very, very different relationship. Now, he's like this bodybuilding-looking raver.

Sam Parr

Most of the time.

Nick Bilton

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. So that was the one person that had it all.

Sam Parr

I want to talk about one more thing.

Nick Bilton

Do you want me to tell that Walter Isaacson story? Yeah, yeah, yeah, go ahead.

Shaan Puri

Let me go ahead.

Nick Bilton

So, Walter told me the story of after the iPad, where he had met Steve Jobs at the Four Seasons, I think it was, which is connected to the Moscone Center. They had met for breakfast; I don't know if it was before or after the iPad. Jobs had ordered a fresh-squeezed orange juice, and when the waitress brought it out, it wasn't fresh-squeezed. It had pulp in it. He called her back over and said, "I asked for a fresh-squeezed orange juice." She brought another one out, and again, it had pulp in it. He just became more and more angry about this orange juice. At one point, she was almost in tears, this poor waitress. Walter said, "Steve, what are you doing? It's just an orange juice! She's trying; clearly, they don't have non-pulp orange juice because it's fresh-squeezed." Jobs responded, "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 where her life has gone and why. I think that, for all the brilliance, there was a lack of compassion. The reality is, none of us are perfect. We're all... yeah, well, do you think?

Sam Parr

You have that you're one of the best there is. Do you lack that? I mean, are you accused of being an asshole?

Nick Bilton

Yeah, I... I fucking love when people call me an asshole. I just don't give a shit. But what I pride myself on is being very, very easy to work with. If we're doing a creative project, if we're writing a movie together, or if I'm working with the producers on a documentary, I am there to make this the best possible. I will never, ever, ever be an asshole. You could never find anyone who would say I would be, because I understand that what we're doing is really hard and we're all doing our best in the pursuit of great creativity. However, I've picked fights with people as a writer and journalist, and I've gone after people, which makes me into a fucking asshole, quite honestly. You know, I had a thing when Dave Morin was doing all of his products and startups. I went after him, and later, I actually apologized to him because I felt like I was too much of an asshole. We had a heart-to-heart about it. I do think there's a great line that Bill Keller, who was the editor-in-chief of The New York Times many years ago, used to say. He said, "I don't believe people should be able to write about other people until they have been written about themselves." I learned that when people started writing stories about me, and I was like, "Oof, that feels awful. That sucks." It was a moment where I realized, "Oh, I don't need to be such a dick to people." I can write these stories, I can be honest, and I can tell the truth, but I need to have some compassion too. That was something I had to learn in the beginning of my career.

Shaan Puri

You talk about your time at The New York Times, where you were in this room. The room had portraits of all the important people who used to come to us and try to tell us what they were doing because we were the messengers. We used to kind of shape the narrative out there, and they tried to shape us, and we shaped the narrative.

Nick Bilton

Yeah.

Shaan Puri

And there were these people whose names you recognized from the bylines, and you had so much respect for them. Do you think that still matters at all anymore? Because for me, I'm like, if I'm a founder of a company now, I don't put $0 into PR. I have zero care if I could get a press mention; it's like so low on the total. My doubt was fifteen years ago when I was building a company. That has changed my respect for kind of mainstream media. I think Trump really distorted reality for everybody when he started going after "fake news," and then we 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?

Sam Parr

There's a practical thing of like, you can get an audience on Twitter or wherever, and you're like, "I don't need you." You can go direct.

Nick Bilton

There are two answers to that question. The first answer is that I think **90% of the media is utter garbage**. It is complete and utter ridiculous drivel that is opinionated and bad for society. I think **10%** consists of people who are working really, really hard to try to do investigative reporting because they care. I met those people. I remember those people at the New York Times when I first started. They were making **$120,000** a year and could be making millions working for hedge funds or wherever they wanted. But they wanted to pursue the pursuit of honesty, setting the record straight, and going after these bad people because there are a lot of bad people in the world.

Sam Parr

Does that 90% of the crap include your past employers? Does that include everywhere? Yeah, 1000%.

Nick Bilton

Yes, 1000%. I think the system is broken... like it's broken beyond repair for now. My hope is that, and maybe this is me being delusional, but my hope is that AI can somehow help fix it. I believe that AI, in the hands of people, can help fix it. When I first started at The Times, you weren't allowed to have an opinion. There was no social media; there was no Twitter. I was there when Twitter came out. I remember being in meetings and asking an editor, "What do you think?" They would respond, "I don't have an opinion on this. I'm a journalist who comes with this impartiality, and all I want to do is report the facts." The problem was that the internet came along. I was one of the first ones to come in. I remember being in a meeting with 40 or 50 people. It was a big meeting, and everyone went around introducing themselves, talking about where they went to school and how they ended up there. I barely graduated high school; I literally had a 2.1 GPA and got kicked out of art school. Everyone else was saying, "I was at Harvard, I worked at The Harvard Crimson," and I thought, "Oh, I'm the odd one out here. I shouldn't be here." I was only there because no one wanted to write for the internet. What ended up happening was that a generation came in after I left. They were the internet people; they hadn't been mentored, they hadn't learned the ropes, and they felt they had a right to say, "Oh, we shouldn't publish Tom Cotton in the opinion section." They would be irate about it. That is not the way the world works. The world works by listening to other people's opinions. I think the reason so many people in Silicon Valley have veered to the right is that the left tells them, "Oh, you can't think like that," and "You're stupid if you believe this," and so on. The whole apparatus is completely broken. At the same time, I am friends with a lot of startup founders who tell me, "Oh, we got a profile in The New York Times, and we had the biggest influx of customers we've ever had," or "We got mentioned in a write-up here or whatever." The same thing happened, and the eyeballs are still there. People just don't necessarily trust them in the way they did. What's interesting is that you have all these new news outlets that come along, like Semaphore and The Free Press. They're trying to say, "We're impartial, we're in the middle," but inevitably, what ends up happening is that as soon as you put an opinion in, the number of listeners or viewers or readers goes up, and then the product ends up steering that way. I think there is a desperate need for something... what I think the solution is, honestly, is that you don't need a right-wing publication or a left-wing publication. You need both. You need a place where there are people who have right-wing...

Nick Bilton

Of views and centrist, of views and left wing, and they're all in there together. They're debating it and they're respectful of each other. Maybe they disagree, but they are all there. The problem is, the New York Times is all left, and the Wall Street Journal is all right, and so on and so forth. You don't necessarily trust any of it.

Shaan Puri

Yeah, I would love to read the debate. I think that's a lot more interesting format: two people who take the other side. Two people who each believe or are willing to argue the best case for each side, so you can read it. 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 a steel man. Is there a story you wish you could write? Either if you had infinite time, or you know, sometimes you get successful and you're like, "Oh, somebody should do that." It's probably not worth me doing it, but somebody could do that. Is there?

Nick Bilton

Is there a great story?

Shaan Puri

Out there, do you think somebody should be doing something?

Nick Bilton

Doing... I don't know. My dream is... I love thinking about stories from all different perspectives. Like, how do you determine when a story is a documentary, a book, a magazine, a tweet, a movie, or a nine-part series on Netflix? I write in all forms of writing, and I'm fascinated by these different mediums. It's like, you know, a documentary features people from the past talking about their experiences in the present. A TV series is a story unraveling as you watch it unfold. A book allows you to climb inside someone's head for seven hours and understand how things looked, smelled, and felt. I've always wanted to write a novel at some point. I think that's the next thing I want to do because I am a voracious novel reader. I have so much respect for the amount of research that goes into writing them. The magic is that you don't realize the authors spent hundreds of thousands of hours researching all the history or whatever it is to create that story. As for nonfiction, I just love stories that embody that old cheesy saying: "If it was fiction, you wouldn't believe it." To me, those are the stories that are the most fun to read, report, and research.

Sam Parr

You have all these different seasons of life. You know, you said in your evolution that you wanted to be a war photographer, and then you accidentally became a columnist. After that, you became an author. 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?

Nick Bilton

I almost did this year, actually. There was a project that I was going to go to, which was a startup in the storytelling space.

Sam Parr

Can you say what it is?

Nick Bilton

I think that what's happening is there's a change coming in Hollywood regarding how we consume content, particularly between short form and traditional storytelling structures. For example, in a film screenplay, a screenplay is typically 20 pages long because each page represents about one minute of screen time. That's why when you look at screenplays, they're in Courier font; each page shot is usually one minute long. Therefore, a 20-page screenplay corresponds to a two-hour movie. There's a whole system set up around this. There's a book called *Save the Cat*, which essentially established a framework where, on page one, the first person you meet is your main protagonist. By page three, you discover what the movie is about. By page five, the antagonist is introduced. By page 30, which is about 30 minutes in, there's a significant turning point—the moment when the journey begins. Then, by page 90, you've entered the third act, and the story comes full circle. While every movie is different, we understand that this structure is a common thread. However, I think this philosophy has been overused. Do you remember the movie *Parasite* that won the Academy Award? *Parasite* changed the game; it didn't follow the typical structure. By page 60, it transformed into a completely different movie, and viewers were left saying, "Whoa, I've never seen that before." That's why people really loved it. What we look for in culture are things that are new and different. Every once in a while, a genius comes along who breaks the mold, and then everyone else copies that. After that, you have to wait for the next genius to innovate again. I believe that the traditional structure of page one, page five, page 30, and page 90 doesn't resonate with today's audiences. They don't have the patience to wait until page 30 to see the turning point. In short form content, there's a new philosophy emerging—like one second, seven seconds, nine seconds. However, many creators struggle with storytelling in this format. I think there's a world where we can explore new approaches to telling long-form stories alongside short-form bites. But at the end of the day, the reason I didn't pursue that path is that I just love telling stories. I don't necessarily want to be a manager meeting with VCs and boards, or getting kicked out by Jack Dorsey.

Sam Parr

How many copies of your books have you sold?

Nick Bilton

Hundreds of thousands of copies. Yeah, over time, I don't... I haven't checked in a long time, but hundreds of thousands. And they've been printed all over and written.

Shaan Puri

Why is *American Kingpin* not a Netflix seven-part series?

Nick Bilton

Like it.

Shaan Puri

Can't be like nobody's... No, that's an amazing show.

Sam Parr

It was okay. That movie was okay. I mean, no, it was bad. It was bad.

Shaan Puri

It was bad, yeah.

Sam Parr

It was bad.

Nick Bilton

I'm not going to tell you the story, but the reason it has not happened is because I got screwed over on the film rights deal. So that's the reason why. However, it may still end up there. We'll see.

Shaan Puri

Alright, 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? What would it be?

Nick Bilton

You do well if you dedicate... you'd need more than six weeks. So let's pretend it's...

Shaan Puri

What would be the first... what can I do in six weeks? I got $19. What do you have for me?

Nick Bilton

If you... I have all these books on storytelling that I read, and they're interesting. You get a little snippet. I think the most interesting of all the books I read was when I wrote "Hatch" on Twitter. I really wanted it to feel like a murder mystery because no one knew what really happened. I read a book on murder mysteries, which was unbelievable. You can read any of them; just Google "how to write murder mysteries." It's a blue book, a collaboration where a bunch of murder writers and screenwriters each write a few chapters. There are a few things I learned from that. One is that when you read a lot of books, people forget to describe smells, and murder mysteries always do. It really brings you in. It's wild to see how it can add this extra layer, like sounds and smells. You know, not just the creaking stairs but also the mold... whatever it is. It just creates this sense of story in your brain. The other thing is the "state of the cow," which is a really interesting concept. Even if you don't write screenplays, it's a fascinating way of understanding character. I've read a bunch of screenplay books by some of the old greats, and they talk about characters and things standing in your way. But I will say, for me, the best way to become a great storyteller is to read stories. I think one of the things that frustrates me about Silicon Valley and the tech bro culture is that everyone's trying to optimize their life for the most number of seconds of this and that. What they don't realize is that some of the greatest things they will learn come 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'd never played before, and I thought, "You know what? I'm going to just learn the piano." I got obsessed with it. I learned how to read music for the first time. Oh, look at you! What is that?

Shaan Puri

I'm on a... Alright, the cover fell off.

Sam Parr

That's just like a New Year's resolution.

Nick Bilton

This is.

Sam Parr

My new.

Shaan Puri

This is my year mission.

Nick Bilton

How's it going?

Shaan Puri

I'm on the favor method here. So, I'm on book two right now. I'm playing... I'm playing.

Nick Bilton

There's a great app that I use in my spare time. It's called **Notes Teacher**, and you just do it for like five minutes a day.

Shaan Puri

**Sight reading practice**

Nick Bilton

Yeah, sight reading practice. But I got obsessed... obsessed! I literally would play two hours a day, and now I can play a couple of Chopin songs and things like that. To me, it was just a fun hobby, but what you learn is that they are telling a story. Hans Zimmer says, "The notes will ask a question, and then the next notes will answer the question." The way Chopin composes is just unbelievable. If you sit and analyze the music, thinking about the highs and the lows and the things that are repeated, it's amazing. This started to inform some of the ways I thought about screenplays. 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 love studying as I read, thinking, "Oh, that was really unique the way they did this." I read a lot of 1950s sci-fi and also a lot from the 1930s, 40s, 50s, and 60s. Incredible writers that we all should read. You understand that these stories are really about people, not just the plots we think they are. The guy who wrote *Game of Thrones*, George R.R. Martin, I saw him speak once at a conference years ago. He said, "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." I think what ends up happening is, as you watch something, the best stories are the ones where you imagine yourself as the character. 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 sever my heart or whatever? And then you can't figure it out, but the storyteller does, and you're delighted by that because it's great storytelling.

Shaan Puri

I think that's your secret, by the way. You're like, "I... nonfiction is usually pretty boring," but yours aren't. I think yours aren't because you consume so much content that's on the mystery side. Yours are page-turners. So, what you know about 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. They take, correct, you know, the best hedge fund, Renaissance, because they took the best AI, machine learning, and mathematical prowess and applied it to finance. 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. He's not the best singer, but he said, "I am the best writer." He sang one of his lyrics and explained, "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." That's why my song sounds different—because I'm using a rapper's lyrics but singing them in a way that is rarely done. It sounds like you've kind of done that same thing.

Nick Bilton

No, I think it's totally true. Look, I think Jobs did this thing where, you know, computers back then were these nerdy circuit boards. He was like, "Oh, I'm gonna marry graphic design with technology." For me, I want to marry that style of a novel with a narrative nonfiction story. There are great writers who've done that in the past, and I have such admiration for them.

Sam Parr

Whenever I get done reading your books, like each time after I've read *American Kingpin*, I'm pretty bummed. I was so in love with reading this, and I was looking forward to finishing it. I would sneak off to find the page and see if I could just read a few chapters. I felt bummed that I was in this relationship with this book, and now it's over. I've searched so long and hard to find something that could fill that need, and only one out of like 20 or 30 books fills that need. I think *Mastermind* was another great book that had a very similar topic. The author did a great job with a similar style of storytelling. But in general, it's been really hard for me to find things. I read a lot of novels, and sometimes when I read a novel, I fall in love with a character. Then I have to remind myself that the character is not real, and I get kind of bummed about it, you know? So, who do you view as a peer or someone you look up to in terms of your style of nonfiction storytelling?

Nick Bilton

Oh, well, just to real quick on the novel: yes, they're not real, but they are based on reality. Every novelist pulls from the people around them to create the characters that you're reading. So, you know, it's like what you know. If you go do research into whatever your favorite book is, your favorite novel, and you look at how they did it, if they talk about it, they're like, "Oh, well, this is, you know, when I was a kid, my grandfather used to tell me the stories about da da da da," or "There was a neighbor across the street." So I think they are real, and it's still people. As far as people I admire and look up to, I, like I said before, I don't really read a lot of narrative nonfiction. I'm sorry, a lot of nonfiction. I don't think there's that... like, I have such admiration for people's reporting and even the writing, but this isn't... I need a story. I can't have an... so that's...

Sam Parr

What I'm describing is that I want something more story-driven, not... I.

Nick Bilton

Need a story.

Sam Parr

This is the shit, man. I've just like... I just love learning about this stuff.

Nick Bilton

Well, you had one last question, Sam, and I interrupted you. What was it? Did you get into it?

Sam Parr

Well, it was about... Sean, did you see the documentary on Netflix? What was it called? It was with Ilya... was it Bitfinex? What was that called?

Nick Bilton

It 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 $72,000,000 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. Every time they were trying to launder it, it would double and double and double until it was at its peak worth $8,400,000,000. She was this wacky, cringe rapper, and he was a part-time magician and investor. It's one of those stories that if it were fiction, you'd be like, "Oh, this is stupid. This would never happen."

Sam Parr

She, Sean, she, or the guy Ilya spoke at the very first Hustle Con, which is kind of funny.

Shaan Puri

Oh, and then the woman, Heather Forbes, thirty into thirty, dude.

Sam Parr

You saw it? Listen, listen, listen. The woman, Heather, she was like a copywriter or something, but she wasn't any good. She DM'd me asking to talk at one of our events or to do freelance work or something like that. Then, she was kind of a sex freak. I had a bunch of friends who fooled around with her, and they were like, "This woman's wild, man. You should stay away." Those types of stories.

Nick Bilton

I was.

Sam Parr

Like joking with Nick, I was saying that whoever we interact with, just like, you know, maybe 10% of them are going to end up becoming amazing criminals. 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.

Nick Bilton

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.

Shaan Puri

Is making a Netflix documentary profitable? Or do you do it just because it's fulfilling and, you know, it's art? I'm curious about how that works.

Nick Bilton

There's not... Look, being a writer, I think, you know, it's good money if you can pull it off. Somebody sent me an article a while ago that said you're more likely to become a billionaire than to become a successful writer. Yeah, it's like, I think about the way in the olden days. You know, at *Vanity Fair*, for example, or *The New Yorker*, they had these contracts for writers. They would get paid hundreds of thousands of dollars a year and they would write four stories a year. They had the house upstate and the brownstone in Brooklyn. It was a different time. Now, you know, everything's been diluted. Media has been completely diluted. We have podcasts, blogs, newsletters, mainstream media, and all that stuff. The advertising dollars and the revenue dollars haven't gone up; they've just been more evenly distributed. For me, I just want to tell stories. I don't give a shit what format it is. It's really fun to be able to write screenplays, write books, write magazine features, and make documentaries. It all just kind of adds up from there.

Sam Parr

I could talk with you for hours, man. Thank you for doing this.

Nick Bilton

Thank you so much for having me. This has been really fun.

Sam Parr

We appreciate you. Alright, that's it. That's the pod.

Nick Bilton

That's the pod.