Storytelling Strategy Better Than Your English Classes Nick Bilton

TITLE: 79 Mins of Storytelling Strategy Better Than Your English Classes – Nick Bilton CHANNEL: David Perell DATE: 2024-09-11 ---TRANSCRIPT--- You have to create drama and tension. Everything has to be tension from the beginning. Otherwise, why am I reading? How do you think about doing that? It’s got to have something that’s leading you to the to the next page. So, where does something like that come from? Learning how to write screenplays. And the other was uh learning how to write murder mysteries. It’s not what I expected her to say at all. With murder mysteries, there are things that they do to really bring you into the story. You’re on the edge of your seat because you’re like, “What would I do? And how would I react?” Well, that’s how American Kingpin reads. I have a friend who’s a big screenwriter in Hollywood and he read a early draft of it and he called me and he goes, “You are so screwed.” And I was like, “What’s going what what’s wrong with the book? I thought it was good.” And he goes, “At the end of the day, everything is a story. Everything. Literally, there is nothing we do in life that is not a story. You go to the supermarket, it’s a story that’s being pitched to you to buy this cereal or that thing. You sit around with friends or dinner or family, you tell stories about the day. Like every single thing, politicians are telling a story. Like, and what makes a great story is a story that has emotion and tension and characters. And I’m fascinated by how you tell a story for each different medium, what you take out, where you put things. So, for example, like a perfect example of this is when you write a news article, you have the lead uh and then you have your nut graph. And the lead is essentially the like this is what happened. The nut graph is kind of explaining the entire piece in in the sentence. And the best part of the story, in my opinion, the most creative is the kicker at the very end. And it’s like so if I’m bored when I’m reading a New York Times article, I always go to the kicker. I read the last three paragraphs. And with fiction, you flip it upside down. So you you you start with this like really beautiful scene and this moment and at the very end you explain it all and I and it’s just I just am always been fascinated by how you how to tell stories differently based on the uh the type of storytelling it is. Um, you know, with documentaries, for example, you have people that you’re interviewing that are telling a story about the past, right? And with scripted content in film and television, you’re seeing it play out in real time. And or you can be creative and come up with other other ways to do it. And I think that to me is always been one of the most fascinating parts of storytelling. But at the same time, it’s always got to it’s got to have propulsivity. It’s got to have characters. It’s got to have something that’s leading you to the to the next page. Yeah. Well, in American Kingpin, one of the things that you do such a clear job of is building up the themes. So, it’s a story of ambition. It’s a story of ambition and then match with early failure. It’s this guy Ross who’s like trying to basically break free of the tyranny of the US government. And what I noticed was before you got into that story, you were just very clear of setting up, hey, he had failed in these ways early in his career. He was reading Von Mises and and Freriedman earlier in his life and you’re setting that up and I noticed like a sense of clarity. You weren’t trying to hide the themes. You’re like, “Here are the themes. I’m going to be very clear about them.” And you’re going to see those beats show up over and over. I probably learned how to tell narrative non-fiction stories by learning how to write screenplays, which was 10 years ago or so. And the biggest lesson I’ve ever learned was a book I read about how to write murder mysteries. And the reason I sought the book out was because when I was writing the Twitter story about Jack Dorsey and those guys, I had written a draft of it and and I gave it to a friend to read who was at Stanford and um it was like on 8 1/2 by 11 and he had been making notes and he got to like page 160 or something like that of a 300page book and he wrote in big red letters, I hate them all. All four that Yeah. Twitter found. He was like, “I hate the all the characters. I don’t want to I’m not rooting for anyone.” And I was like, “Oh, Jesus.” Like, you can’t hate the characters. You have to want to read them. So, I was like, “Well, who who do you want to read that you hate?” Oh, a murderer. Like a mass murder. That’s a So, I started like, “How do they do it? How does Hitchcock do it? How do these people?” So, I started studying that. And what’s really interesting is there are like all these themes that you can learn when you’re writing about essentially bad people uh that make you still care about the character. Um because when you’re when you’re reading a book or you’re watching a movie or something, you’re not just following the story, but you’re imagining yourself in it and you’re imagining how you emotionally would would react to it and what you would do. That’s why we love heist movies cuz we’re like, “Oh my god, I didn’t figure that out.” And like and um or you’re you’re on the edge of your seat because you’re like, “What would I do if I was that person? How would I react if the monster was in the house?” And with murder mysteries, there’s a thing that are things that they do to really bring you into the story. Yeah. What are they? Well, one of them is um every murderer has a mother that loves them because your mother will always love you. And so the reason Hitchcock gave these characters, these really bad people who are like murderers, mothers, it’s because the moms still love them. The other thing that they do, he did, um, or not just him, but all these all these murder mystery writers, they give they make you human by like you lose your keys because cuz murderers still lose their car keys, right? Or they like forget to pick up the the post or they, you know, they drop their grocery bag. They and these are so you can identify with those moments even if you can’t identify with the desire to murder someone. Um, you can identify with those moments and then you be you can put yourself in the body of the character. Yeah, there’s an idea here. You know that quote, the road to hell is paved with good intentions. You need to show people what those good intentions are. What is it that people are actually going for? And if we can feel that, what is the goodness that they’re trying to achieve? Yeah. Then I think you get a more well-rounded character. Yeah. I mean, there’s just lots of things that you have to do in a story as you’re telling the story to get people to identify with the character. And um and that’s something I’ve just put a lot of thought and work into. And you know the other thing as far as like screenwriting goes and how that relates to narrative non-fiction is it’s courier font right um it’s I like 16 18 points I don’t know I forget what the actual point is but the reason that it is and it’s it’s laid out the way it is the reason is because one page is one minute okay so a screenplay is 120 pages long which is a movie which is 120 minutes long and in a book when you’re writing you can meander for a couple of pages. Like you can be like, you know, Ross Orbert got really into um reading this, this, and this book about this, this, and this economics, and let me explain what that means to you, and so on. And you can meander, you can like you can talk about the kind of sweater that this person had and where it came from, and it brings you back to some relationship with them and a friend and a family member, whatever. In screenwriting, every single solitary word counts. I’m not exaggerating. every word, every single solitary thing. Why does it matter more than so little space? When you are reading a screenplay, the screenplay is written for you to visualize it in your head. Whereas with a book, you’re visualizing parts of it, but you’re you’re listening to the story at the same time. There’s a saying in screenwriting that you should get into the scene as late as possible and out as early as possible. Okay? So sometimes you’ll write the scene where like for example if I walked into this house, right? Um and this house is crazy. This house is crazy. And I walked into this house and let’s pretend it was haunted cuz it feels a little bit like it is. And and I walked in and I and I came inside and I sat down and so on and so forth. That’s the scene, right? The way you would come in late is you would come in, we’re already talking and you would get out before I even answer a question and then the next scene would explain the answer to that question. A perfect example of it is like um let’s just say you take a couple older couple and they’re fighting uh they’re sitting at dinner and he’s got some heart problem and she’s nagging at him or whatever. That’s exposition. It’s a long scene. It’s like sit down and she starts lecturing and whatever. The perfect way to do it to make so you get in in late and out early is the an old couple sitting at dinner um and he says honey pass me the salt and she goes did you not hear what Dr. Brown said the other day about your cholesterol and like that’s an example of like making it it’s a couplet of two of two things. So learning all of that and like reading books like um there’s a great book on screenwriting called kill uh save the calf. Okay. You just learn how to how to think in this kind of way that is very character-driven uh very judicious in in the words that you’re and the and the things that you’re picking and very cinematic. And then when you take the murder mysteries and you put it in that and then my history of reporting and research and like which I get obsessive about which we can talk about I think you can start to create these kind of narrative non-fiction stories that feel feel like they’re fiction. We’ll get into research cuz there’s some crazy things there. We got to talk about that Excel spreadsheet. Yeah. But when you’re editing a screenplay versus editing a book or an article, how is that process different? Right. When I think of editing a book or an article, hey, you throw into Google Docs, you do some comments here and there. Is that what editing a screenplay is like? The best way to read a screen to to edit a screenplay is to read it. You do little voices and stuff. I don’t, but I have friends that do and it’s funny to watch them do it. You know, they I actually use AI a lot now to read it for me. Really? Yeah. Um, how does that work? Just put it into like Speechify or 11 Labs and like and it reads it aloud and then you can kind of hear what it sounds like. So, you’re reading the screenplay out loud. And are you doing that collaboratively or just solo? Just solo. you know, you um uh sometimes if I’m working with people, I’ll do it collaborative um collaboratively. Um and then I don’t know why, it’s just the way my brain works, but I don’t think of things in words. I only think of things in images and then I describe what the images look like on the page. I totally see that. If you say like orange, I can’t imagine the word orange. I can just think of an orange and then I would describe what the orange looks like. And I could write the word orange, but my brain doesn’t actually write the word orange. So for me, every it’s everything’s a movie in my head and I’m describing what the movie looks like. Well, that’s how American Kingpin reads. Yeah, that’s my goal with like all of the writing I do. Now, I did some video stuff in college and I noticed that it was different. It was more non-fiction. It was more like TV news, but I noticed that whenever I would do a cut and I would export it and I’d show it to other people, it was too fast and I’d always need to slow it down. And I would get into the editing, boom, boom, boom, boom, boom, fast pace. People be like, it needs more space to breathe. But I’ve noticed that in writing that intuition for fast pace tends to be better. Yeah. Do you feel that? I think that you I think it’s like music. I mean, I listen to all kinds of music, but I really only listen to class piano. Uh, and I play piano and I play classical music and and um and I think that you know there are moments that are fast and intense and and you know you’re pressing harder on the keys and there are moments that are slower and and I think I think I think writing is music in in some respects and the fact in you know there are times you speed up and there are times you slow down and I remember a specific moment in American Kingpin um where we’re in the library and the SWAT team comes in. is so intense. Like you’re on the woman is in there. I mean, I wrote the book and I still read it sometimes. I’m like, “Oh, what happens next?” And and right after that, I remember I’d done a pass of the book and um turned it in and my publisher, who’s amazing, Nikki Papadopoulos, um over at Penguin Random House, she I’d gone straight into some other crazy scene afterwards and she said, “I feel like we just need to slow down. Like we just need we just went through the most insane moment of the book. we just need to slow down. And the next chapter goes back in time and we go to um to uh Korea and I did all this research and reporting into this and we see the laptop that they had just seized being made and we follow the creation of the laptop and the chips slowly being put in and on the assembly line and getting on a plane and and it brings us now back into the story. And so it just was a way to like, okay, we’ve gone through the crescendo of the story, now let’s take a beat and come back into it. And when you read books, articles that are poorly paced, what is the author missing that you see so clearly and you just want to be like, do this, do this? I think the reality is, look, and I I’m not saying like this to be a an ass but like most people can’t write, right? I think I’m a good writer. I don’t think I’m I don’t think I’m one of the best writers. Like I I read people like, you know, um Gabriella Garcia Marquez and I’m like, “Holy shit.” Like that I couldn’t couldn’t do that if you paid me billion dollars and gave me 20 years. Like I think that we all come in here and there are certain people that can get here and there are certain people that can get here. Most people can get here and I think you can push, you can learn and you can push yourself and you can do all these things but I think you have to kind of understand like what am I good at? And that’s the thing you have to kind of go for. And and so when I read certain writers and they’re trying to do the the creative and dramatic leads and this that and it’s just not working, like it’s like you’re clearly good at X. Focus on X. Mhm. You can try to get why a little bit better, but like what are you good at? Give me a sense for what that sounds like once you have that self-awareness. I think that I’m good at um understanding what the reader knows and doesn’t know and knowing when to tell them what they need to know. So there’s in all of my books and all of my magazine features and all of the screenplays, I I have this way of introducing characters when they think this the reader is ready to to meet a new character. So, you don’t want like there’s books you I’ve read where um narrative fiction books where they like you come in and you’re and all these names are being thrown at you. You’re like, “Oh my god, who the hell is this?” Like, what? I don’t Wait, Bob. Who? I thought we just met Fred. Who’s Jane? I don’t remember Jane. And you’re like going back and if you’re on a Kindle, you’re using X-ray to try to remember. A lot of fiction writers do this, too. And what I try to do is I say, “Okay, here’s, you know, again, going back to screenwriting, in a screenplay, in a film or TV show, the first person you see on this on the show is the main character. You don’t bring in, you know, if I were writing a movie about you, I wouldn’t start with me or the guy outside or whatever and then meet you. We would meet you instantly.” And I think so you in a book, you you you meet that person. you meet the main character first, then you bring in the next character when when you feel like you like, okay, I remember who Ross is. Now, let’s meet Julia, his girlfriend. Right? And so, I build the books out so that you each time you you’ve now you’re I’m comfortable with who this character is. I know them. I know their traits and and then I’m going to meet the new one. And like another example is usually I do this towards the end, but like I’ll go back through and I’ll take character traits about someone so that you remember them and then remind you them like fudge with Ross Ober. Yeah. So like uh and then Jared, who’s the HSI agent, um he’s into Rubik’s cubes, right? So um I uh I make sure that in the first several times that you meet him, he’s got a Rubik’s cube on. So, like his cars, like there’s a scene where I say scenes because I think of them as scenes. I don’t think of them as as as the book in some respects. There’s a scene where he’s driving through Chicago and I describe the car going through Chicago and then I I um come up on the Rubik’s Cube dangling on his keychain. So, we’re like, “Oh, it’s the Rubik’s Cube guy.” Right. Um and so, and that’s how we remember things. Those the Rubik’s Cube guys. Wait, I I actually already forgot his name. It said Jared. Jared. Yeah. So, it’s interesting. I went Rubik’s cube guy, HSI agent Jared. That was like the order of how I remembered what you had just said. It was also I think I really had to focus on this because there was so many acronyms. It was FBI, HSI, Secret Service, IRS, you know. Um the other part of it too I think was um you know the IRS guy uh he read everything three times because he read somewhere that if you you don’t you only remember 20% of what you read. So he figured if you read it three times, you remember 60%. And so I have these scenes where every time you come back to him, he’s reading an email three times. And you’re like, “Oh, I remember it’s the RSK.” And you don’t have to think about it. You don’t have to work. And you get to just stay in the story. This is why I can’t read Russian novels. I I just can’t keep up with the name. I can’t keep up with the names. But that’s something I think that I’m able to put myself in the reader shoes and and know what they are going to be able to understand and when. And that’s that’s I think that’s like my superpower when it comes to writing books. And I read a lot of biographies and I find myself being like for the first 200 pages being like, “Oh my goodness, can we just get to the stuff?” I love that you keep reading the 200 pages. But what I find is later on I’m really happy that that early stuff is there, but I need the context of what happens later to appreciate what happened when he was 11 years old and he was at a park. What are some of your favorite biographies? I really like the Neil Gabler biography on Walt Disney, but the beginning of his childhood is not interesting until I learn about Disneyland. And then I can trace everything back to the beginning. Yeah. And I just wish that the art of the beginnings of biographies was something that we did better. You have to create drama and tension. Everything has to be tension from the beginning. Yeah. I mean, it’s from the be otherwise why am I reading? I mean there are certain books I can’t you know it’s funny I can’t read non-fiction books just can’t get through them like I lit I read a tremendous amount of fiction you know 100 books a year in fiction and biographies and whatnot I’ll read but I cannot read a book a non-fiction book because it just I I get bored and I’m like God and I’m scanning through it I’m like I have a lot of criticism of today’s um uh you New York Times bestseller list and like the top books like the Colleen Hoovers and stuff like that because I think that the writing is atrocious quite honestly. Why is it so popular then? Because it’s a good story. I would totally believe if someone told me that Colleen Hoover and the people that write those kinds of uh uh books where it’s actually an AI had written it. Um, but what they do really well is that they there’s tension and there’s romance in this and that’s what people are into. And I just wish the thing that bums me out is there are so many phenomenal writers who just don’t their books don’t get read partially because this is a longer conversation but because uh the the book talk world decides what is popular in culture today and I don’t think uh they should be the people deciding what’s popular in culture but uh um because they just go for the lowest common denominator but but I think that um uh there are some lessons to be gleaned from those popular books. books, which is that they know how to hook you, how to create characters, and how to tell a good story. They tell great stories. They tell a great story. But there are great writers also who sadly also tell great stories who uh are not uh not read. Yeah. I think that I think that we the the you know what popularity and populist and mainstream um has largely shifted because of the internet and and I think not for the better for the worse in my opinion. H if 100 Years of Solitude came out today, it would not be it would not be read by the Book Duck crowd because it is I which is to me one of the greatest novels of all time, it would not be read by them and it would not be on the New York Times bestseller list because they wouldn’t have the patience to get through it and um uh and the writing is probably too good and and yet it’s one of the greatest novels of all time. When you say that the writing is probably too good, what do you mean? I think a beautiful turn of phrase can make your brain it just like it like it’s a dopamine hit. Totally. Right. There are so few writers in history that are capable of just turnurning those out and I think your your brain when you’re processing them it’s a lot. It’s like whoa, you know. Um it’s like popping a a chocolate box of ecstasy. You’re like this is amazing. This is too much. And I think that I mean I don’t know I’d love to hear your thoughts on on the the the book talk culture but like I just think the stuff that they endorse is just garbage most of it. One of the things that you do a good job of is is cliffhers and I want to yeah I want to read one. So this is we’re talking about what happens early in a book and this is about Ross Olrich. say in a matter of months he would find himself dealing with dirty cops and rogue employees and Ross Olrich would have to decide if he wanted to have people tortured and killed in order to protect his growing enterprise. And what I think happens there is you’re giving me enough about the future where I’m like what where are we going? But also I’m like okay it’s going to be a while there. I got to keep reading to build up and it makes me keep the book open. with American Kingpin. I I remember two things. One is like um the chapters are very short. Very short. What do you have 58 chapters? And each chapter has a cliffhanger because I was I just done the Twitter book. Um and I was writing for the New York Times and Vanity Fair at the time and I was noticing this trend of like shorter form content. You know, there was a time where at Vanity Fair, I would have read written a 20,000word feature, right? Today, if I write a 6,000word feature, that’s considered incredibly long. I wanted to create these chapters that were like bite-sized chapters, uh, but also had an insane like propulsion to them that kept you going. And so I will say like if I were to create critique myself like I think that in American Kingington there’s maybe like one or two too many um at certain points but the goal was to make it so you read these little chapter and you’re like n just one more I’ll just do one more. If you create the moment in the beginning where it’s like this holy shit moment, um, you know, there’s in in Hatching Twitter, the book opens up where Evan Williams, the is the CEO of Twitter, he’s about to get fired and we open up with this scene where he’s in his office, the Twitter headquarters, and he throws up into a garbage can and he’s been fired uh, and he’s got to give this speech in front of the 300 employees and he He wipes the vomit off his shirt and he walks out in front of them and he holds the microphone and then we cut away and we go back to the beginning and there’s not the cliffhers. There are cliffhers in in Hatching Twitter, but there’s not as the chapters are longer and there’s not as many because you’re like, “How the hell did that happen?” You know, because then you meet Evan when he’s young and he’s riding his bike and in Paluma and he’s like got these ideas and and then we follow through and we come back to that and we pay it off and and so it’s like it’s just it’s again like thinking of it as a movie and then writing it as a book. What makes for a good cliffhanger? Giving away enough that you want to keep reading but not too much that you know what’s going to happen. Hm. You want to ask the question in the cliffhanger and then answer it in the next in, you know, answer it later. And you can’t cliffhers can’t be too far apart. So if I say like Russ has got to decide if he’s going to have people killed and then 200 pages from now he decides it, you’re like, “Wait, what?” So you’ve got to make sure the pacing of it. It’s like it doesn’t have to be the next section, but we can start to seed it and then we get to and and and then we answer it. That’s an interesting turn of phrase. Start to seed it. So, a lot of what you’re doing to create drama is you’re setting up a theme. You’re creating a cliffhanger. And you’re doing that by, like you said, you’re showing a little bit of the future, but you’re not revealing too much. And then that’s what I begin to see. There’s all these seeds that you begin to plant early on through motifs, through characters, through themes, through patterns, whatever. And then over time, those begin to develop and grow. Yeah. I won’t start a book until I know what the theme is. There’s the saying of like um you have to be able to describe what your book is to someone in an elevator going between two floors. Um which is ironic because it’s a 100,000 word book, but you’re just saying it in a tweet essentially. Everything has to come back to that scene. Every single like I always think of it as like a it’s a through line and and the the the circles have to always it’s like being braided onto something. they always have to come back and if they don’t you’re you’ve lost the reader. So what is an example of a good theme but start with how that theme could have been bad at the beginning. So give me some of the confusion and then give me some clarity later on. I did this cover story recently for Vanity Fair about Tim Cook and the Apple Vision Pro and uh and I went up to Apple Park and I spent a day with everyone there and like spent time with Tim Cook and met the engineering team and everything and the theme that I came away from for the piece was that the future is coming whether we like it or not. And that was the theme of the story. And so everything I wrote the story was just kind of trying to point that out. And when I wrote the piece, the Vanity Fair stories about Therronos, it was a story of how Silicon Valley always had an ethos of fake it till you make it. Um, and she and and Elizabeth Holmes uh got so caught up in the in the bright lights and the power and the fame that she forgot to actually make it. She just faked it. And uh the consequences of course were potentially deadly. And do you define this theme early on? Like have it at the top of your paper? Like everything’s got to go back to it. It’s just in my head. It’s I literally won’t put a I won’t put a pen to paper until I know what it is. You know, Elon Musk, a big feature I did on him, a cover story on uh on him for the Vanity Fair. Um it was the theme was he needs a a problem to solve and if there’s not one there, he’ll create one. Uh which is so evident in who he is. And so the story is just about when things were going good for Elon, when he was at the top of his game was the worst moment in his life. Uh uh when he was the richest person on earth, when all of his companies were doing well, when people liked him, it was just that he had nothing to fix. So he broke it. How about themes with specific people? One of the things that you were talking about earlier is the sort of duality of people. These these contrasts, they’re not fully good, they’re not fully bad, right? It’s the Soulja Nitsson line. The line between good and evil divides every human heart and sort of painting both of those. Well, I don’t think anyone is truly good or evil. You know, it’s it goes goes back to the murderer like the mom still loves the murderer like uh the murderer still loves the mom. To go back to bad writing where people don’t see that nuance where they just decide a character is a character and I’m going to paint them that way makes it for not a good character cuz you’re like, “Oh, he’s just a bad person.” You have to create nuance in your characters because we all have nuance. you know, you see like it’s like Ross Olrich like, you know, he was willing to have people, you know, potentially murdered um uh to save his empire, but at the same time, he had this incredibly sweet side to him that like helped literally helped old ladies across the street and when he went to a flower stall, bought a flower for the woman who worked at the flower store cuz he figured no one ever buys flowers for the woman who works at the flower stall, right? I’ve been playing around with this idea for a novel that I want to write about based on a um a story from my family during the Holocaust and everything. And I was doing a bunch of research and I found all these old pictures of Hitler and you’re like, “Oh, the biggest monster ever created in the in human history.” But then you see him with his family it, you know, up in the in the mountains of Austria in the summer. They still loved it. They loved it. you know, it’s like there’s still like so you have to you can you can’t create monsters without nuance. And I think that’s the biggest challenge for a lot of people because they start to judge their characters that they’re writing about. And like someone once described it to me um Charles Randolph who wrote the the screenplay um the big shorts, phenomenal screenwriter, he said, you know, like you can’t look down on your characters, you have to look out with them. I mean, that’s the way you have to approach a character. Otherwise, you’re just you’re just making them into the a character of themselves. What else goes wrong when you read a character who doesn’t feel real? I was just reading this RC Sheriff novel from 1936, I think. Um, he was a writer in England who uh wrote a bunch of sci-fi books and there’s this great moment. The novel is essentially the story of how the moon is um has has gone off course and it’s on course to collide with Earth and and we have 8 months left before the world is destroyed potentially. And all of the people in high society like this the main character is like a a novice astronomer learn about it before everyone else. And then finally the news breaks and the moment that the news breaks he he is talking to like a neighbor and um with his wife and the neighbor says something about it and the main character says says yeah it’s true you know um there the moon is going to collide with the earth and it’s going to happen um in 8 months or whatever it is and the husband turns to the wife and he goes I told you it was 8 months not 8 weeks I told you it was 8 months and it’s like we’re all going to die and yet they’re arguing about the specifics. That’s life. That is reality. Like a bad version of that would be like, “Oh my god, we’re all going to die.” And it’s the person runs down the street and hides and cries, whatever. To get into those human emotions that happen in those moments that like that’s that’s great character. And I think what people fail to do sometimes is um they fail to make people human and real where they’re worrying about their lost car keys or, you know, the things like that. um or arguing about who did the dishes and those are the things that we that’s what we identify with. How do you think about making the jump from description to visualization and what I mean by that is you talk about you feel it your books feel like a movie. I can see so many scenes. I can see chairs. I can see the magic mushrooms. Like there’s so many things like that. And I would presume maybe not for you but you would start you say okay this is what happens. This is sort of the facts that you would maybe get in a courtroom, but you’re making some sort of leap into a new paradigm from the facts that you would get in a courtroom to now this is like the vividness of a scene from a movie. How do you think about doing that? It’s called painting the room, right? And um and it’s something I learned in journalism very on. And I I’ll tell you the story of how I learned it. I was in the newsroom at the New York Times and I was sitting next to uh my cubicle was here and Andrew Rossin. No way. Was right here and Andrew and I were friends and we’d like you know we were both um like you know young and he’d been doing it a lot longer than me and um there was a a helicopter crash that had happened with these bankers. There was some big secret deal that had been going on. Everyone survived. Everyone was fine. But he it was he was writing this front page story and I was hearing him he was on the phone with someone and they were like look I can’t tell you any of the details of the deal because SEC rules or whatever. He goes just describe the boardroom to me like and he’s and he’s like I’m listening to him say this and he goes what does the boardroom look like and uh and he’s like okay and I can just over here he’s like okay mahogany desk. Okay. Were there were there was there any any stuff on the table like for breakfast? Okay. Croissants. What kind of croissants? Chocolate croissants. Like regular croissants. And I’m listening to ask these bizarre questions like, you know, was it carpeted or wood floor? Like what was the view? Could you see the Statue of Liberty? I just was like, “That’s weird. Why isn’t he asking about the deal?” And uh this is 20 years ago. And um and then the the piece came out in the paper and I picked it up and he paints this room and he’s like in a boardroom overlooking the Statue of Liberty on the 34th floor at a mahogany table, eight executives were negotiating a deal that would change their blah blah blah blah blah. as so and so, you know, reached for a chocolate croissant. Uh um it was sure that it was going to happen. He doesn’t know anything about that deal. Nothing. He knows he doesn’t know how much. He doesn’t But you are like, “Oh, he was there. He understands everything, right? And what he’s doing is painting the room.” And and so you’re by doing that, you’re bringing the reader into into the story. And you don’t have to know everything. You just have to know how to describe certain things. Even if I do know everything, I want you to feel like you’re there. And um and we can get to the reporting and how I how how ridiculous I get with it stream. Everywhere that I can go to, I will go to and I will sit in the chair and I will that they sat in and I will order the food that they that they ate. You will lie down in Alamo Square. I kind of think of it it’s like a I’m playing a game of Tetris. Hm. That’s not what I expected you to say at all. No, it’s literally the way I think of it. And I’m like, “Oh, that piece can go over here, and that piece can go over here, and that Oh, and I got a line.” And like, and that piece I’m just going to I’m just going to have to put it to the side for now. And then that one I’m going to put to the side, and oh, there’s one. Great. I can bring this one back. And And it’s like doing the reporting and you’re looking for all these pieces. You’re just trying to pull it all together and and until you have a story. And um and so with the reporting, one of the things I did like with let’s just say American Kingpin um I got access to um to Ross Albbrick’s laptop um through through the investigations and and stuff that I was doing. He had a laptop that was split into two sides. It was the Ross Albbrick side and then there was the Dread Pirate Robert side. And what he didn’t realize, which was essentially his downfall, was that he had been saving all of the chat logs for two and a half years as the Dread Pirate Roberts with all of his employees. So for I got those and it was essentially like I got to sit in the room of this company that was being built called the Silk Road, right? Uh for 2 and a half years and listen to what everyone was talking about at the water coolant. So I take all that. So, I put it in essentially a database, right, with the time stamps and the dates and the people’s names and whoever’s typing and talking. Then I go and I start doing all this research. I like I interview people. His roommate, his girlfriend, his mom, his, you know, whoever. You met all of them? I His mom only talked to me on the courtroom steps and and then decided not to. I his his girlfriend I spent you know weeks with um his you know roommates uh college high school friends track them all down like so you take all these interviews and then you put that in the database and you’re like this person was in this time and this time and then you take all the social media stuff you can find so um uh tweets Facebook posts uh Venmo uh accounts like anything literally everything like you’re you’re essentially being like the FBI agents, right? And so we put all that in the database and the timestamps start to line up, right? This is where the jigs the the the Tetris pieces start to kind of come together and then finally I can take the locations and I can go and I can do my own reporting. So I can go to the coffee shop I know he was working out of which ironically enough I lived three blocks away from. So just in Glen Park in Yeah. I went to the library. I went to the we went to the same grocery store but I went to the sushi place and I know what he ordered with his girlfriend. So, I order that and I sat in the same seat and it’s I don’t use I’m not like describing what the sushi is, but I can say, okay, I I if I need to describe like if I need a moment where I’m painting the room and I can say like I know that they’re wood um chopsticks. I know that the bathroom’s to the left, so that you know, someone walked out of the back. I can describe all of these things if I need them. And um and this is where it gets really creepy in my opinion uh is you start to put them all together. It so you’ve got the Dread Pirate Roberts, you’ve got the text messages, you’ve got the emails, the photos, and and then you start to get the geoc all the photos have their geolocations. So you start to put them on a map and then you can start to figure out what happens in between. And so a perfect example is there’s a scene in the book where um Ross goes to um he goes camping for the weekend. And so the dread pirate Roberts says, “I’m going away for the weekend. Um you know, do X, Y, and Z, and I’ll be back.” Ross um uh is with this girl who he’s going with um and some friends that I found their social media and they had posted a couple of photos and one is Ross and the girl and the other couple and they’re standing um uh be by a car on the street in San Francisco. The next is um a photo going past the Golden Gate Bridge and you can see like someone’s hand and another is um at a campground and there’s no geoloccation on the campground photo, but I want to know where they went camping cuz I want to make a chapter out of this. I want to make a I want to make a scene out of this cuz it’s a big moment because I know the Dread Pie Roberts is away and at the time like there’s a lot of crazy shit going on on on the on the Silk Road website and um I figured out by going through the maps of downtown San Francisco on on um Google Maps. I figured out where where the where they started out, the time between that and the and the Golden Gate Bridge and then the time they got to the campground. So then I looked for it was like 48 minutes. So then I looked at every like wooded area within 48 minutes of the Golden Gate Bridge and found it on the maps and then went there and then walked it and then got to sit where they sat and then I could describe the whole thing. So talk to me about what happens when you show up at the campground or you show up at the Glen Park Library and you see that chair. Are you scribbling notes? Do you just look and kind of photographic memory? I remember a lot. Um, but I’m making notes of like smells and like that’s the other thing. Uh, uh, another thing that’s I think um, really important is we describe in writing is like we describe the senses. We describe what we see and what we hear, but we never describe what we smell, right? So I that’s another murder mystery thing they do. Um, and I so like I’m thinking I always try to do that cuz I really think it brings you into the into the scene. What I’ve gathered is you don’t need a lot of descriptiveness. I think writers often overdescribe. They’ll sometimes do this like purple pearls. Oh, it was there and the the lilac sky and this all you need is one or two three things three things. That’s it. You need like the smell of the pine the pine needles and the smoke and and the the sound of the the crickets and then the and then then the the the way the sky looks with the trees, you know, like and that’s it. It’s funny. The brain is very good at taking a few details and inferring something. I mean, look at cartoons, right? Cartoons don’t give you much at all. And you’re like, Homer Simpson, love that guy. Again, it goes back to the screenwriting. Like, what what can I take away? Um, and sometimes I’ll write these like big long like, you know, paragraph scenes and then I’m like, this is like, okay, we get the point. We’re at a campground. Like, and then I just take it all the way or I trim it down and make it like these little tiny seeds. What have you learned about writing dialogue and how you keep the pacing up there? What accuracy truth is like? I mean, I can’t even remember the first thing we said to each other when we walked in today. How do you get some semblance of truth? One of the hardest things I think in storytelling when it comes to narrative non-fiction is knowing what is true when people disagree about what is true. And I’ll give you an example. In hatching Twitter, Jack Dorsey gets fired the first time, not the second or third time. I talked to Jack and he’s like, “I remember what happened. I walked out of the office. I met Bis Stone at the Whole Foods and we sat inside and we had soup. I remembered as clear as day and it was raining outside and we talked about blah blah blah.” B Stone goes, “I remember it clearly. It was sunny outside. We met at the tea garden, the Japanese tea garden, and we sat outside on the lawn and we had tea and and we talked about So I’m like, which one is right? You know, I don’t know the exact, you know, exact detail. So in an instance like that, you go back and you look at the weather almanac and you’re like, oh, that one’s probably more accurate because it was raining and they were and you know, sure. And so you can do that and then if you don’t know, you just can’t write it. like if it’s really that important. There are certain things where it’s just like irrelevant. It’s like, you know, oh, you know, Bis is wearing a white shirt. Uh, and Bis is like, I was wearing a blue shirt. And it’s like doesn’t matter. Like, you know, you just pick one. It really doesn’t. But if it’s something like he shot him in the head. No, he shot him in the leg. Like those are like you have to get those details right. And um and so you just that’s just something that you kind of you just have to be the editor of and decide. How about with dialogue? How do you get that right? A lot of the time there is actually overlap. You know, people I mean they may have a word or two that are different, but um what’s great about the books that I’ve written is that people have used social media and so I can get their words from social media um or videos or whatever and so I can get the dialogue verbatim. But when I’m interviewing people and they have a and they don’t agree um at a certain point I have to make a decision. Um, and and then the other thing is I think with when it comes to actually good dialogue is it’s so important to be uh to not be expositional. What does that mean? Me telling you what happened rather than me showing you what happened. So, for example, like you know, I went and I sat in a room with Dave and we talked about blah blah blah blah blah. rather than me showing you like we’re describing the room. It’s this balance of making the reader do the work but not too much work. Uh and not too little work cuz then they’re like you talking to me like I’m a baby like. And so um so you really want to make sure that the dialogue is is show not tell. How about for something like this? I I’m I’m going to edit this lightly. PG-13 family show. Here we go. These often craft jokes could range from the truly unpatable to the truly bizarre. And this about Tarbel American Kingpin. Would you rather sleep with your mother or sleep with your father? Would you rather be half your height or double your weight? Where do you come up with this stuff? Tarbell, one of his co-workers asked. So, where does something like that come from? Because it illustrates so much about this weird guy who always is doing these would you rather jokes. Um, so I interviewed all the agents involved in the case. um spent a lot of time with them and and you know Tarbell’s not going to tell me that as the FBI agent that he I mean I he didn’t care but he just wasn’t going to volunt he just was like he’s telling me about the case and the investigation but the other agents are like oh my god did Tarbell do the what would you rather jokes with you you know and cuz he did them with me I remember sitting down and I was like do you do these what would you rather jokes and he was like he was like I’ll only answer it if you answer the following question then he asked me like would you rather and I was like, I’m not answering this. And he was like, not answering any questions. So like, but I think that, you know, it’s like those are the character traits that you remember. You know what else is like this? Bezos’s laugh. People always talk about he’s just got this rolling loud laugh. Bezos would never tell you that, but people who’ve been in his presence are always like, “Yeah, his laugh. His laugh. He got to hear his laugh.” Totally 10,000%. I do a lot of photography. Um, and I that was a thing I didn’t like past life uh for a little bit. But, um, Bruce Gilden uh, who’s a phenomenal photographer and he takes pictures of like down on their luck people and I love hearing the stories about them uh, and like how he meets them and their background and everything cuz they’re just so emotional and so human and so not judgmental. the worst writers are the ones that judge the characters they’re writing just to take your opinion and your viewpoint and how you feel about them. You have to take it out and you have to make them human and um and you just can’t judge them. Do you feel like character building is the same in your film projects versus the books? Yeah, it’s exactly the same. It’s you’re figuring out who a character is, but you’re also figuring out who the others are. And there’s a great way of thinking about it that in any story, one character must be trying to do something and another character must be standing in their way. So that creates tension, right? If I want to walk into the kitchen here and grab a water, that’s not a very good story. If you’re standing in between me with a knife, that’s a great story. So you have to think about it. And the other thing is like, you know, I think it’s just studying like I think it’s funny because I think most movies today suck. Like they’re just terrible. They’re like mainstream and populist and bad and everyone in Hollywood will tell you that and it’s you know it’s the reason that all of the studios are suffering and you know but they have the people that came before them figured it out like they the story formula is amazing. Like um look, screenwriting is without question one of the forest forms of writing. There is that and fiction novels. But um but there are so many things to learn about visual storytelling that you can apply to to narrative like what like Pixar has the like it’s the 22 laws of storytelling. 22 laws of storytelling. Um you know your character starts here. Uh something happens where they go through some sort of change. Uh they’re presented with a challenge. Sorry. They have to decide to take on the challenge. They take on the challenge. There are obstacles in their way. They defeat the obstacle. There’s a second obstacle. They defeat that. They come back to where they were as a changed person. That’s storytelling. That’s the story. Where things get complicated is where you’ve got the arc of this character and the arc of this character and the arc of this character and this one and and then the themes all have to tie together and you just have to your brain has to be able to handle all that. Do you feel like the story reveals itself once you get to the end, which a lot of people say, or are you like, “No.” Ah, you figure out the story at the beginning and then you write the dang story. You know, there’s the thing when you’re a reporter, you do your reporting. You don’t write in the middle of your reporting. You don’t like interview five people for a feature and then start writing and be like, “Oh, I got to interview five more people.” You and I remember in the newsroom in the New York Times, it would be like, “Um, you’d have your meeting with your editor and they’d be like, “You done with your reporting? you gonna start writing and it’s like no one would ever be like did you start writing yet? First question is are you done with your reporting? Are you done with your research? Are you are you ready to put pen to paper? And um I don’t know how people can write without knowing what the story is. Tell me about the David Car line. Keep typing until it turns into writing. What does that mean to you? His thing was like you just got to get you got to get it on the page. I’ve written millions of words over the last 20 years. I don’t remember 90% maybe 98% of what I wrote and it doesn’t matter. Like the thing that holds so many people up is they think it’s this precious thing and it’s the most important thing ever. It’s not. It’s just words and you’re just telling a story and you just got to do it and then move on to the next one. And it’s the greatest thing I learned in my career as a journalist was that there’ll be another one. I became a reporter at the times and I remember I had like a really good run of breaking all these stories and then I wrote a piece funnily enough it was about the Amazon Kindle and it was Christmas Eve and it blew up and all these people came after me these like pro Amazon pro Kindle pro Bezos people pre-ancel culture but it was like this is the first time they really came for me and my editor said you’re just going to write another story tomorrow don’t worry about it like you got to take the lumps you got to learn to take the lumps but you’ll do you’ll do better on the next one cuz I think I’d made a mistake in this in the piece. Okay. And I think what people get stuck with is they’re like they think it’s like they think everything’s a Pulit surprise winning novel that like is going to shoot to the number one New York Times best. It’s like it doesn’t matter. The Eminem one shot one. It’s like you don’t it’s like it’s like do it and be done with it like move on and stop being so precious. How has the magazine feature changed throughout your career? How is it different now than it was 20 years ago? I think the magazine feature has changed dramatically uh um in the last 20 years. Um and the reason is is because of the internet. So if you go back and you pick up the New Yorker or Vanity Fair or any of those magazines from 30, 40 years ago, the lead of these stories was was like 800 words describing the scene, describing what it looked like, painting the room. And the reason was is cuz you had no idea what it looked like because there was no internet to be like, “What does this look like? What does the the car show in Los Angeles look like?” I don’t know unless I’ve been there. So, you as the reporter had a job to describe it. Today, we all know what everything looks like and we can Google it in 12 seconds. So, we don’t need that description. And I think where where people fail in their attempts to be like fancy magazine writers or even like fancy just writers writing these scenes. It’s like you’re writing for a style that existed 30 years ago and doesn’t make sense for today and people don’t read because don’t finish your article because they’re like well what’s like I know what the Eiffel Tower looks like. You don’t need to describe it to me. And so what I’ve always tried to do especially over the last five six years is try to come up with like new and more interesting ways of coming into a story that are unique as unique as possible. So that the reader’s like, “Oh, this is different.” And the one time that I have described the room and explained it was the Tim Cook feature because no one had been in that room, right? And that’s the exception that proves the rule. That’s the exception because I took you inside the most secret place on Earth, which was the the labs where they developed all the new Apple hardware. So that’s like, oh, I want to know what that looks like. But the other ones, it’s just it’s a creative uh creative creative way of bringing into the story. Yeah. Let’s get into the Elon article. So, the title is Elon Musk’s totally awful, batshit crazy, most excellent year. Elon Musk is on a mission. He’s on a mission to Mars. He’s on a mission to save humanity from its reliance on fossil fuels, which could destroy the planet and kill us all. He’s on a mission to save us from artificial intelligence algorithms going rogue and machines ending human life as we know it. And we get this repetition of on a mission, on a mission, on a mission. And then you write, “He’s on a mission to prove the Corona virus fatality rate is greatly overstated.” And then we get two, two, two, to dig tunnels underground, to alleviate the fatuous cycle of traffic jams, to save journalism, to mitigate the effects of climate change. Two, two, two. And then at the end, it says, “All of these missions are completely possible in the realm of physics and science, especially with Elon Musk’s brain working to solve these problems.” That’s the end of the first paragraph. And then the beginning of the second one goes like this. But this year, Musk set off on the most difficult mission of all. Coming into that story, I was I was just so fascinated by like Elon’s mentality of like that he could do anything. And I was like, “Okay, well, I went to SpaceX. I’m like, okay, paint the room of SpaceX. Okay, well that we all know what space it’s there’s rockets. That’s cool. But like what I wanted to do was paint the room of Elon’s brain and and his brain is one that’s like I can do anything and he’s half right and he takes on he can do anything but he it also gets in his own way and so I wanted to take kind of take you inside his mind rather than paint the world that he lives in that we all know what it looks like and I think that that’s uh you know TM Nick built an intro where what we have is we have the themes that have been set up we have some repetition to make those those themes clear and then you say but this here. Musk set off on the most difficult mission of all. What is it? Okay, now what’s going on now? I got to keep reading. I kind of learned a little bit of that. Like, I don’t particularly like Hemingway. I’m not a huge fan of Um, but why? He’s always drunk. His characters are always drunk. It’s just It’s not really a world I I love, but his writing is unbelievable. He’s Hemingway. But what he does is like pick up the Old Man in the Sea. He says old man and sea and blue and boat like 10 times. And you’re like, “Got it, old man. See, and he’s he’s, you know, his whole theory was like this repetition will will tell you what the story is about and all the other stuff is just there to the scaffolding holding it up.” Whereas like Fitzgerald and and those others who I’d love u um they were much more about like coming straight in on the character and um hooking you into who that character is and then bringing you into the world and and you following along and um yeah like Hemingway it’s like it’s just boom boom boom like I’m going to take a baseball bat to your face and you’re going to see that word over and over and over until you just you remember it right. Yeah. How do you think about a conclusion? So here’s where you’re right. Musk at times can even acknowledge this himself. So this is the very final part of the piece. One former employee told me that once this person asked Musk, “If you ever worried about losing his mind,” Musk replied, “Does a crazy person ever look in the mirror and know that he’s crazy? Perhaps this is really the most important mission Musk is on, to never have to answer that question.” I think it’s my favorite part of writing is writing the end of the story. Is that right? I find myself incredibly lucky that I get to climb inside someone’s head for whatever period of time they spend reading something that I wrote. That’s really cool. Like I remember I met Paulo Koelloo uh years ago. Wow. And we I get to Davos and there’s like snipers on the roof and everything and like it’s totally insane there. And like meeting all these people like Hillary Clinton, whatever. I was like, “Oh my god, it’s Paul Quelloo.” Like that’s who I was like so excited to meet. And I I went and we was talking to him and I was like, “How does it feel to know that like your book, The Alchemist, has been on the New York Times bestsell, you know?” He goes, “The fact that one person wants to spend time reading something I wrote, to me, that’s like amazing.” And I I feel the same way. Like I feel like it’s like, you know, we we I think people get upset today because they look at like the numbers from like books that sold 50 million or 100 million or whatever. And like the fact that one person wants to take six hours of their life and spend it on the, you know, spend that time reading something that you wrote is pretty cool. Like, you know, I feel like the end is like it’s your like partying goodbye with that person and like you should leave them with something to think about that you both shared. Well, there’s a concreteness to this one, right? Perhaps this really is the most important mission that Musk is on talking about. Does someone look in the mirror and know that they’re crazy? And you’re saying he just doesn’t have to answer that question. Yeah, that’s true. I mean, that’s true of him. And it’s very clear. Yeah. And it reminds what you said earlier about the flip between fiction and non-fiction completely. If you were if you were writing that as a fiction piece, you would flip it. You would start off with him not wanting to look in the mirror probably, you know, you wouldn’t start off with the tension of the beginning. You would flip it around. At least I would. Would an example that be anina Leo Leo Toltoy and he says all happy families are alike. Every unhappy family is unhappy in his own way. So that’s the beginning. And that’s sort of like the kicker that you were talking about. Yeah. If that was a Vanity Fair story, that would be the end. That would be the kicker, you know. Uh you wouldn’t open a vanity like a magazine feature with that. But um it’s really interesting. I’ I read a tremendous amount of fiction and uh and I’m always fascinated by what they choose to lead with and what they end with and I always feel like it’s it’s flipped. Oh, I got to ask with Vanity Fair, they have maintained a style for so many years. What is it that they’re doing in the editing process to maintain and grow and nurture that magazine style without suffocating you as the writer? I don’t get edited that much anymore. It’s interesting like Vandy there are these very long paragraphs, you know, and um just from a stylistic standpoint. So, you just learn very quickly, okay, that’s how I write the features for them. Whereas at the New York Times, like a paragraph is like two sentences, it’s sometimes one. And um uh the New Yorker has their specific everyone has their style almost and so you kind of adopt that and you just kind of learn like what the magazine wants and then you write in that it doesn’t you’re not changing your style of writing you’re changing just the way you put it on the page in some respects. The reason you end up there is because you have a specific style that they like and they want you to continue to write. Like you talk about being yourself. How do you know what you’re good at, what you’re not good at? How do you define that and then lean into the things that you’re good at and kind of back off the things you’re not as good at? I’m incredibly impatient. Uh and I just I have ADHD. I’ve always had it and like and which you would think like oh that’s probably not a great tool to have as a writer. So like I lean into that. It’s almost like these jigsaw puzzle pieces. And so like I will write just some random six paragraphs that I know I know what it looks like and then I’m like okay I’m bored. I and then I’ll go write six more paragraphs and then two paragraphs and then a whole chapter and like and I put them and then I’m copying and pasting and putting them all over the place and and and so on and uh and then at the end I have to like really force myself to pull it all together. That’s the hard part. That’s the hard part. I have a great visual memory. Like I can remember every detail visually, but I’m terrible with like people’s names and things like that and so I just have to I’m the same way. And the fact that you write like that makes it really easy for me to follow your characters. Well, that’s why I have to follow my own characters. So, I write in a specific way that’s like that works for my brain where I can just I can look at I can literally still picture the Rubik’s Cube guy. Uh yeah. Well, I can still picture it’s funny every detail of the photos as I was describing from Ross going on the camping trip and the campground. I can everything is still as clear as day in my head, but I can’t remember the woman’s name that he was with, right? And I wrote her name a hundred times. So, so I you just have to lean into the things you’re good at and then and then figure out how to work with the things you’re not good at. What’s an example earlier in your career where maybe you got punched in the face or slapped on the wrist for going against your nature and you’re like, “Oops, it’s a lesson learned.” I got punched in the face and slapped on the wrist many, many, many times. Uh almost got fired from the times a couple of times. Uh um one time I I was being interviewed by Wired magazine. uh they were writing about me and the work I was doing and I said I don’t read the print paper anymore and uh and then I got called into the uh uh executive editor’s office and they were like you can’t say things like that publicly. I literally thought I was going to get fired. Another time I um made a mistake on I was on CNN or something and I like made a mis I had inserted my opinion about Mark Zuckerberg in a way that was very clearly opinion and that was a no no. So like there was those things. I think the thing that um the biggest lesson I learned at the times was I wanted to like pick fights. I wanted to I wanted to take a baseball bat to people’s faces. Like I was like I just was that was what I wanted to do as a reporter and uh to like take on the bad people per se. And I remember there was a point in time I’d been doing it for a long time and uh Gawker decided they were going to start writing about me. Oh man. Like a weekly thing for a while. Uh, and I have a pretty thick skin, but for a minute it was like, “This sucks.” You know, and I remember being like, “Oh, uh, this is not fun.” And the executive editor at the time, uh, uh, Bill Keller, had once said, um, that he believed that journalists shouldn’t get to write about other people until they’ve been written about themselves. And I understood what that I remember hearing that, but I never understood it. And I understood it. And so when I had been on the receiving end of um of being written about negatively and largely fairly unfairly, I realized like, oh, there was some things I did that I shouldn’t have. And I actually apologized to a couple of people uh privately. I was like, hey, look, you know, I was young and and uh um picked some fights that I shouldn’t have. You know, and then there were like the moments that I think like kind of were really big moments for my career, which were like I remember David Card said to me when I first became a columnist, he said, um, pick a fight you can win. So, I decided to pick a fight with the FAA, which was just ridiculous and stupid. At the time, you couldn’t bring a Kindle or an iPad or an iPhone on an airplane and have you’d have to put it away, remember, during takeoff and landing. Oh, that was so infuriating. So infuriating. So, I was coming back from Thanksgiving and um uh somewhere and and I was I was reading this book on the Kindle. It was like two pages left and I was like, “Oh my god, what happens? What happens?” And the flight attendant was like, “Put put your Kindle away.” And I was like, “This can’t blow up a plane.” And I was like, “If it could blow up a plane, terrorists would get on and yell something and then turn off airplane mode and we’d all go and and I was so irate cuz it was so stupid.” And I was like, “All right, I’m this is the fight.” And I ended up winning the fight. And I like I did like all these columns and I went and did all these like went to these testing facilities and like tested the EM like just all this stuff and it was like a huge moment because they changed the FAA changed the rules. That was because of you. Yeah, that was that was like a man. Uh that was that was my reporting and it was like it took a a couple years but that was the right fight to pick. And then Bezos actually thanked me uh in his earnings call and he said, you know, we’ve got this great news. The FA is allowing people to use Kindles on airplanes. Special shout out to Nick Bilton for doing that. And uh so that was a fun that was a fun one. And how do you write about people differently now that you’ve been through through that experience? I tried to just be like they’re humans, you know, even like the bad ones, they’re still humans. Just, you know, there’s a thing that with the internet like um where people forget that there was a human being on the other side. I remember getting emails in the time when I was at the times if I’d write something about like Apple that people didn’t like or whatever and you’re an idiot and you don’t know what you’re talking about and and and you should I hope you die in a plane crash. It was one of them and I wrote back to I never really wrote back one I wrote back I was like I just wrote about an iPhone like just chill out like it’s like like and the person wrote back and oh my god I’m so sorry I didn’t think you’d actually read this. You kind of have to apply that to your writing about people. Like I still pick a lot of fights, but I um I just am a little bit more cognizant of the fact of what I’m saying and who I’m saying it about. I don’t know if this is a weird question, but are there challenges that come with writing a successful book? 1,000%. Look, American Kingpin has sold hundreds of thousands of copies. Um it’s in multiple languages. Um uh and and I remember I have a friend who’s a big screenwriter in Hollywood and he read a early draft of it and he called me he was the first person I think to read uh next to my wife who who read it. But he was the first person to read the full draft of it and he called me and he goes, “You’re fucked.” And I was like, “What’s what’s wrong?” He goes, “You are so screwed.” And I was like I was like I was like, “What’s going what what’s wrong with the book?” I thought it was good. And he goes, “You’re never going to get a story this good ever again.” It’s a dang good story, man. And he’s like, “And you’re going to spend your career trying to find one.” And I was like, “You’re right.” And so the challenge has been like, um, I wrote a book that won’t get published. Um, that was about the NRA. Uh, wrote the whole book and, um, and had a tremendous amount of scoops in it. uh and all the stuff that and then CO hit and we were literally working on it right when CO hit and um and then the world shut down and all of the stuff I’d spent two years reporting came out in the Leticia James trial. Um and so and no one from the NRA or places like that would do interviews. I had to be they wanted to be in person. No one wanted to do Zoom back then. Now I think people would but like back then it was like it was a new totally new thing. So I had to put the book on hold and then once we came back from co I felt like it was I’d have to re for it to be a good book. I’d have to redo it and it was such a dark world that I don’t want to live in it. So now I’m just like trying to find my next narrative non-fiction book. So if you have ideas, so this is great. What what we should do is in the YouTube comments get some ideas. But now here’s this leads into a great question. You got to guide us. What makes for a great narrative non-fiction book? Like what are the things that if you see check check check check check you’re like okay now we’re on to something. I have this belief that there are two kinds of stories. Okay, there are big stories that are about something very small like yourself, right? So, for example, an inconvenient truth is a huge story about climate change that is completely overwhelming to to figure out like, well, where’s my part in this? But it makes it you see, oh, if I don’t drive a Range Rover and if I don’t use plastic bags and if I if I, you know, try to do this, this, and this, I can have an impact on this big story. And then there are small stories about something much bigger. So, for example, uh Tiger King on Netflix was a small story about four people or five people in this world to collect exotic cats. And really, it’s about the American dream and business. And it’s either a big story about something small or a small story about something big. There is no story in the middle. There is they do not exist. They exist, but they’re terrible. Stories in the middle are bad. That’s just a fact. like they are populist, quite frankly dumb, and they just I I just don’t think that they should exist because it’s just like it’s like a halfass of one or the other. And I think that you you have to really put the work in to figure out which story it is. Well, as I were to think about say I was trying to give you recommendations, here’s how I would think of it. Is there a person who’s can be around this that we can follow and you can let me know where I’m wrong or missing something. Is this a story? You were talking about NRA, talk about the Silk Road that has been big, but it doesn’t feel like someone has really done a good job synthesizing what is going on. Yeah. And what else would you say as part of the checklist? I’ve been part partially been thinking about, it’s funny you said about biographies. Partially I’ve been thinking about like doing a biography next. Um, and maybe one that has been done but hasn’t been done. You know, I don’t know like if I apply like my narrative non-fiction style of writing to a biography, like would it be interesting? You know what kind of biographies I like is biographies of people who are a little bit out of the spotlight, but it’s like this person is super important. There’s a book called The Box that just tells the story about container shipping. Oh, that’s cool. And through the guy who developed the container ship and you think of these just container ships, like what could the big deal be? But if you think about it, it used to be that every single piece of cargo would have to be taken off of a ship individually, then put on say the train individually. And now what you could do is you have now have container shipping. It could be on the ship, on the train, on the truck, same thing. Massive efficiency gates. Totally. But it has to be about something bigger. You know, the Silk Road is about this moment in time where anyone could create a world and then they could become God in that world, right? And that world could kill people. And you have a line in there about how somebody who could be running a multi-million dollar drug kingdom from just a little library in Glenn Park. Yeah. And it could be anyone from anywhere. Um and then the Twitter story is a big story. It’s a bit this big thing, but it’s about these small little people that created it and they’re in fighting and backstabbing to to to to take power and control of it. And so whatever it is, it h it always has to have a big theme. All right. Two questions. Yeah. First one, if I were to ask you to teach a class on narrative non-fiction, what’s on the syllabus? What do you need people to understand about how to do this? Well, Gabriel Garcia Marquez, I um just read a book about his writing and how he did it. And he was like, you shouldn’t start writing till you’ve read 2,000 novels. And um uh and that’s one of the things that’s really interesting. Like I have a home office that I go in my office and I’m like, I got to sit at my computer and type until it becomes words, right? or till becomes, you know, a story. And no, you don’t. You can go in your office and you can just sit and read a book and you’re working like you’re you’re processing. You’re like, and it’s so hard in today’s day and age to kind of do that. It’s really hard and it shouldn’t be. How consciously are you trying to cultivate your voice on the page? It’s like a dog on a one of those long leashes, right? And eventually they just come back. You can’t create, you can’t manufacture a voice. You can, it’s not going to be very good. Your voice just becomes your voice. But you can um dilute your own voice or prevent something from who you are from showing up on the page. Maybe through fear or you have to tell the person in your head that’s like Mr. or Mrs. Doubt to go to hell. I don’t have Mr. Mrs. Doubt. It’s like I’m just very lucky that I just don’t. And it’s partially because it was all an accident. Never wanted to be a writer. It was never my goal in life. It just happened through like a series of accidents. So when I w when I became a reporter of the New York Times, I was like, “Someone’s going to figure this out and they’re going to come tap me on the shoulder and say it’s time to leave.” So for me it was always like I get to drive the Ferrari for a little while. Like this is really fun and then next thing I know I like had been doing it for 20 years. Um but I know for a lot of people the doubt is the thing that pulls them back and you just got to you you have to ignore it. You have to it’s hard but you just have to you have to say it’s just it’s just a bunch of words. There’s another piece tomorrow. Another piece tomorrow. Well, you did always love books. And I think that comes from your mom. And I really like this. I guess in a copy of War in Peace that she gave you. Every year she’d give you a gift and they’re often in books. And I like this note. Dear Nick, never live without beautiful books. Love, Mom. She used to blow dry her hair and she would have a book on her knee and she would blow dry it and but she had the blow dryer in a way that wouldn’t flap open the pages. But she had a really unique thing. She always read the last page first because she couldn’t deal with the tension of what would happen. She needed to know and then she would read it, then she would go back to the she always did that. But her house in England was um like I remember like just going up the stairs or just books everywhere and a lot of the books in my office are hers. um she taught these kids in prisons in the north of England and she was like they were like rough kids, you know, like like people that were like in jail for quite a long time for things they’ done and they like and she said she remembers like moments when she would be like explaining like the story of like Hamlet or something and they would like be paying attention and they would be asking questions and uh and I think that’s what the power of storytelling is all about. It’s like what that’s why we’re here. One thing I forgot to mention that is the most important thing to me in writing is that you don’t tell the reader what to think. You present them with the good and the bad and the ugly and let them decide. I did not tell you what to think about Russ. I intentionally did not in any way, shape or form. I presented him and one of the biggest questions I get all the time, it’s like over and over and over is did he deserve the sentence that he got? And I don’t know I and everyone has a different answer. So yeah, if you have any book ideas, put them in the comments below. Don’t forget to subscribe, like, and comment. If someone If someone finds me a book idea, I will pay them for it. Oh, there we go. Yeah, I I No, I just How’s this? They’re in the acknowledgement section. They’re in the acknowledgement. You get to come over for dinner and play with my dog. I have a very cute dog. Take it. So that was fun. Yeah, it was great. Thank you very much. Yeah.