Why Andrew Ross Sorkin Spent 8 Years Chasing One Story

How do you stay locked in on one project for eight years? Andrew Ross Sorkin shares what he learned while writing his bestselling book 1929: Inside the Greatest Crash in Wall Street History and How It Shattered a Nation https://www.thepaintedporch.com/products/1929-the-inside-story-of-the-greatest-crash-in-wall-street-history-1?_pos=1&_sid=4d3da5615&_ss=r in today’s conversation with Ryan. They talk about what it really takes to write a massive, deeply researched book while juggling a demanding career and family life. Andrew opens up about the fear, insecurity, and obsession that fueled his eight year journey into the world of 1929. Ryan and Andrew get into why writing still feels hard for him, the surprising reality of how much of history comes down to human behavior, and the strange process of trying to understand people who lived a century ago. Andrew Ross Sorkin is a financial columnist for The New York Times and a co-anchor of CNBC's Squawk Box. He is also the founder and editor of DealBook https://www.nytimes.com/section/business/dealbook, a financial news service published by The New York Times. He wrote the bestselling book Too Big to Fail https://www.thepaintedporch.com/products/too-big-to-fail-the-inside-story-of-how-wall-street-and-washington-fought-to-save-the-financial-system-and-themselves?_pos=3&_sid=4d3da5615&_ss=r and co-produced a movie adaptation of the book for HBO Films. He is also a co-creator of the Showtime series Billions. His new book is 1929: Inside the Greatest Crash in Wall Street History--and How It Shattered a Nation https://www.thepaintedporch.com/products/1929-the-inside-story-of-the-greatest-crash-in-wall-street-history-1?_pos=1&_sid=4d3da5615&_ss=r. You can grab signed copies of 1929 https://www.thepaintedporch.com/products/1929-the-inside-story-of-the-greatest-crash-in-wall-street-history-1?_pos=1&_sid=4d3da5615&_ss=r by Andrew Ross Sorkin at The Painted Porch: https://www.thepaintedporch.com/ https://www.thepaintedporch.com/products/1929-the-inside-story-of-the-greatest-crash-in-wall-street-history-1?_pos=1&_sid=4d3da5615&_ss=r Follow Andrew Ross Sorkin on Instagram @SorkinSays https://www.instagram.com/sorkinsays/?hl=en and on X @AndrewRSorkin https://x.com/andrewrsorkin?lang=en 🎥 Watch the video episodes on The Daily Stoic YouTube channel https://www.youtube.com/@DailyStoic/videos: https://www.youtube.com/@DailyStoic/videos https://www.youtube.com/@DailyStoic/videos 🎙️ Follow The Daily Stoic Podcast on Instagram https://www.instagram.com/dailystoicpodcast/?hl=en: https://www.instagram.com/dailystoicpodcast https://www.instagram.com/dailystoicpodcast ✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail https://dailystoic.com/dailyemail 🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/ https://store.dailystoic.com/ 📱 Follow us: Instagram https://www.instagram.com/dailystoic/, Twitter https://twitter.com/dailystoic, YouTube https://www.youtube.com/@DailyStoic, TikTok https://www.tiktok.com/@daily_stoic?lang=en, and Facebook https://www.facebook.com/dailystoic See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:06Ryan Holiday?

  Welcome to the Daily Stoic Podcast where each weekday we bring you a meditation inspired by the ancient Stoics, a short passage of ancient wisdom designed to help you find strength and insight here in everyday life. And on Wednesdays, we talk to some of our fellow students of ancient philosophy, well-known and obscure, fascinating and powerful. With them, we discuss the strategies and habits that have helped them become who they are, and also to find peace and wisdom in their lives.

• 0:51Ryan Holiday?

  Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. I usually record the podcast during the week, try to keep the weekends free for doing stuff with the family, reading, hanging out, relaxing, whatever. But a couple of weeks ago, I came in to do one over the weekend. And I got here and there was just like tons of traffic. And I was like, what's going on? And then I could hear all this noise. I barely found a parking spot to get in. And we forgot that there was a huge car festival in Bastrop. The whole main street was blocked. There were very loud, classic cars up and down the road. There was a snow cone or a lemonade stand in front of the Daily Stoic Studios. Actually,

• 1:36Ryan Holiday?

  that's something we've been doing. We've been, we took this storefront offline. It used to be a barber shop. John the Barber, he passed away. And now it's the studio. And it's sort of like, what do we do with the storefront? We let sort of vendors on the weekends just kind of camp out there and it's helped support like little small businesses and stuff. So someone from the Painted Porch, not knowing I was doing this podcast, had set up like this lemonade, snow cone vendor person. So they were doing their thing. And I was like, oh, my God, this is a, this is not going to be good for this podcast that I am very excited about because it's going to be crazy noisy. Thankfully, it was all right. Able to sort of remove some of the noise and my guest was very understanding when he managed to find his way into the studio. But it was also a nice, you know, like sort of picture

• 2:19Ryan Holiday?

  of small town life as it had been for many years. It was packed, all the people actually kind of segues nice. Imagine it's October 1929, you're walking down Main Street in Bastrop, stock market's at an all time high, things are going amazing, it's time of peace and prosperity mostly, and then the music stops. Maybe it takes a couple of days for the news to make it this far, or maybe not, right? Because it was an interconnected world then. But the market crash of 1929 changed everything, led in many ways to the events

• 3:04Ryan Holiday?

  of the Second World War. It led to in many ways that reinvention, the rearticulation of the social contract here in America, many, many market reforms. And also, it led to this fantastic book that I just read, 1929, Inside the Greatest Crash in Wall Street History, How It Shattered a Nation by Andrew Ross Sorkin. He has been on book tour all over the country the last month. And so I was really excited while he was in Texas that he swung by, really excited to do this in person. And I loved the book. It was a book I was planning to read anyway, but I was gonna wait, I was gonna savor it. It's a big book. And then found out he was coming. I said, All right, can I read this book in

• 3:48Ryan Holiday?

  a day and a half? And I did. And it was fucking great. It is a fantastic, super well researched book. I really enjoyed it. I think you will like it. And in the first part of this episode, Andrew takes us behind the scenes at how it took him eight years to write it, and a lot of the lessons that went into writing it. And I think you're really gonna like it. If you don't know who Andrew Ross Sorkin is, you've almost certainly experienced his work over the years. He's a financial columnist for the New York Times, co-anchor of CNBC's Squawk Box. He is the Founder and editor of Dealbook, which is a financial news service published by The Times. He wrote the bestselling book, Two Book to Fail, co-produced a movie adaptation of it for HBO.

• 4:32Ryan Holiday?

  He's also the co-creator of the Showtime series Billions. And this new book, 1929, Inside the Greatest Crash in Wall Street History and How It Shattered a Nation, is a must read. He signed a bunch of copies of 1929 while he was here. You can follow him on Instagram at Sorkin Says or on Twitter, Andrew R. Sorkin. I think you're gonna like this episode. Thanks to Andrew for coming out. I wanted to split it up because it was such a great episode. And let's get into it.

• 5:04Ryan Holiday?

  I feel like the best question to start with is probably one you've never been asked.

• 5:07Speaker 01

  Please.

• 5:07Ryan Holiday?

  Which is, so do you think we're in the middle of a bubble right now?

• 5:12Speaker 01

  You and Leslie Stahl.

• 5:13Ryan Holiday?

  How many people have asked you that? That's, I'm actually more interested in how often you've been asked that question on this book tour than the actual answer.

• 5:21Speaker 01

  Oh, invariably, almost every time.

• 5:23Ryan Holiday?

  Right.

• 5:24Speaker 01

  So, yeah, dozens of times.

• 5:25Ryan Holiday?

  And people think probably that it's a somewhat original question.

• 5:30Speaker 01

  I don't know if they think it's original or not. I think that they think it's the question that people want to know even more than they want to know about what actually happened in 1929. They want to know about whether this is going to happen to them now. I get it. I get it.

• 5:46Ryan Holiday?

  I don't want to read the book. Just tell me, do I need to be worried?

• 5:48Speaker 01

  Pretty much.

• 5:49Ryan Holiday?

  Yeah.

• 5:50Speaker 01

  Give me the clip. The Cliff Notes version is, should I sell everything I own?

• 5:53Ryan Holiday?

  That is the weird part about the book tour part where it's like you're answering the same questions and then you, it almost becomes impossible to give an original answer to a question anymore because you've said it all the ways that it's possible to be said. And then I feel, I don't know about you, but I feel like, I feel phony just saying bits.

• 6:16Speaker 01

  The same thing.

• 6:17Ryan Holiday?

  Yeah.

• 6:17Speaker 01

  Oh, I do too. And I will admit to this now, and maybe I shouldn't admit to this. I did an interview a couple of days ago where I thought to myself, am I repeating myself? Like, did I say earlier in the conversation the exact same thing?

• 6:33Ryan Holiday?

  Oh, like in that, you lost your bearings completely.

• 6:37Speaker 01

  I was so lost.

• 6:38Ryan Holiday?

  Yeah.

• 6:39Speaker 01

  I happened to be in London. So I think the time difference got me. And I was like, I just said, now happily, I had not said it prior.

• 6:46Ryan Holiday?

  Right.

• 6:47Speaker 01

  I mean, in this particular, I had said it prior or something similar. So yes, you are right. That's a thing.

• 6:54Ryan Holiday?

  The other weird one is like, you have to be somewhat conscious of whether you're just wearing the same things and all the like.

• 7:02Speaker 01

  Oh, clothing.

• 7:03Ryan Holiday?

  Yes, you're like outfit tracking yourself because like you don't want it to seem like you own one shirt.

• 7:09Speaker 01

  This is true. I, you know, I wear a lot of suits because I'm on TV, so I get the different ties. I'm sort of like cognizant of that. So like this, by the way, I don't think I've actually worn sneakers casually or anything at all. So this, this for me, this is actually how I like.

• 7:24Ryan Holiday?

  Dress up for your stuff?

• 7:25Speaker 01

  This is like how I like to dress, but yeah, do I have to dress up? I think people think on that, on Squawk Box in the morning that we should be wearing ties.

• 7:35Ryan Holiday?

  Why? Who cares?

• 7:36Speaker 01

  Because most of the, because you're oftentimes interviewing a politician or a CEO who shows up with a tie on. I don't know. It makes us look more official or something.

• 7:52Ryan Holiday?

  I walked in here the other day. I was interviewing someone and they were like, did you just go for a run? That's what they said. I was like, whoa.

• 7:59Speaker 01

  You look good. You look good.

• 8:00Ryan Holiday?

  I look all right.

• 8:01Speaker 01

  You're always looking good.

• 8:02Ryan Holiday?

  Thank you. Okay. So I'm, I am reading this book. Here's what I was, obviously the book's very interesting. But when the fuck did you write a 600 page book? Do you write like in between commercial breaks on Squawk Box?

• 8:14Speaker 01

  No, no, no, no, no, no. I actually find writing, okay, a couple of things because you, I love watching you and listening to you talk about, actually about the craft of writing.

• 8:21Ryan Holiday?

  Okay.

• 8:22Speaker 01

  I find writing very hard.

• 8:24Ryan Holiday?

  Sure.

• 8:25Speaker 01

  Like super hard.

• 8:26Ryan Holiday?

  Yeah.

• 8:27Speaker 01

  Like I have visions of people like Michael Lewis playing the computer keyboard like a piano, cackling to himself. I am not cackling to myself. I am in pain as I am typing. Somebody said a writer is someone to whom writing does not come easily. So I think it's a compliment. But to your question about timing, I actually find that I always need to block out at a minimum two hours. Yeah. And possibly as much more than that, in part because really, for me, the first 30 minutes, even 40 minutes, is almost like a ramp up to get my brain into the right space, to almost reacquaint myself with where I left off last, to sort of reorient sort of how I'm going to tackle. Right.

• 9:13Speaker 01

  Things. So that was actually the hardest part. So a lot of times writing at night, I mean, a lot of times writing at night. Because this is like your fourth job. I got a couple. Yeah. I got a couple. So I writing at night, airplanes without wifi, always turn the wifi off on the airplane. Don't even try to, I mean, it hardly works to begin with, but don't even play that game. Yes. Vacations, though I know people would think that I, that's not a vacation. My children would say, Dad, you're sitting on the beach with a laptop on your lap. What are you doing? And I would say, I'm writing the book and enjoying myself. Yes. And they couldn't contemplate how that could be. No, this is the thing that I don't get to do because of my job. Right. And it's what I actually like to do.

• 9:58Speaker 01

  For the first couple of years, by the way, it actually did feel like a true hobby. Because you're just in this own world, you're exploring and learning.

• 10:04Speaker 01

  I was just trying to figure it out. I was just trying to figure it out. I wasn't even sure whether I could make it work. I had no real concept or conceit of how it was all going to go. Well, you said, I think you say in the acknowledgements, you took a bunch of books about the crash on a vacation. Yeah, that's, yeah, that's how it started. I was, literally went on vacation with my wife. And I had a Kindle, I brought some, I brought some books and I remember downloading a couple of books. And there's some great books about this period. And they sort of made me obsessed about the period, but also made me think that there was a white space to craft the book that I wanted to write. Right. Yeah, it's the falling in love with a world or a time period. That's, that's like.

• 10:47Ryan Holiday?

  That's the, the part that's just for you.

• 10:50Speaker 01

  But the truth was, I was scared the whole time.

• 10:52Ryan Holiday?

  Of writing it?

• 10:53Speaker 01

  Well, two things. I was scared that I wasn't gonna be able to find the kind of granular detail that I needed to make each character pop in a consistent way.

• 11:04Ryan Holiday?

  Sure.

• 11:04Speaker 01

  Because these people aren't alive. So unlike when I wrote Too Big to Fail, I couldn't go back to people or try to like find, there wasn't extra material. Either was gonna, either I was gonna find it in some archive somewhere, or it just doesn't exist.

• 11:17Ryan Holiday?

  It's a different kind of reporting that you hadn't really done before.

• 11:21Speaker 01

  Totally. It was completely new to me. I mean, even just learning my way around a library was new to me, to be honest with you. So there was that. And then, I don't know if I should say this, I felt like, um, when I wrote Too Big to Fail, it sort of felt like lightning in a bottle had happened. In a way that didn't feel real, and I wasn't sure was all really like my own doing. Like you say to yourself, it worked. Like that book worked.

• 11:44Ryan Holiday?

  Sure.

• 11:45Speaker 01

  But maybe it worked for lots of reasons that I wasn't always sure had to do with me. Meaning like the timing of it. There was sort of like a crazy interest in what had just happened. And so you get insecure about these things.

• 11:59Ryan Holiday?

  Yeah, yeah.

• 11:59Speaker 01

  Like about whether you can actually do this for real. So I think-

• 12:03Ryan Holiday?

  Also, if it's not intimidating, it probably means you're not doing anything good. Like-

• 12:10Speaker 01

  But I also think I was so scared because I thought that book worked. I didn't want to do something that didn't work.

• 12:15Ryan Holiday?

  Yeah.

• 12:16Speaker 01

  So it's sort of like, it was, it felt like there was like a different bar that I was trying, I was trying to clear my own bar, but then I was also like trying to clear some other bar that I didn't really-

• 12:25Ryan Holiday?

  The tricky part there is that's a bar that you don't actually control.

• 12:28Speaker 01

  Right.

• 12:28Ryan Holiday?

  Like if you're like, hey, I want to be better. I want the reporting to be better and the writing to be better and all that. That can be intimidating. But if you're like, well, I just want the vibes to be the same or better. And you're like, you don't control the vibes. Cause you don't control what's happening in the world and you don't control what other people think about what you do.

• 12:46Speaker 01

  Right. No. So that's scary.

• 12:48Ryan Holiday?

  Yeah.

• 12:48Speaker 01

  And I think that weighed on me. I mean, I think that like, that was like a little thing in my head the whole time.

• 12:54Ryan Holiday?

  You worked on it for 10 years?

• 12:55Speaker 01

  More like eight-ish. And the truth is on and off. There were periods of time where I was like- Full pedals in the metal.

• 13:02Ryan Holiday?

  Yeah.

• 13:02Speaker 01

  And then there were periods, especially we had the pandemic.

• 13:05Ryan Holiday?

  Yeah.

• 13:05Speaker 01

  Threw things into a bit of a mess. And just other periods where I had to, you know, be super intense in my day job.

• 13:11Ryan Holiday?

  Yeah.

• 13:12Speaker 01

  So I don't want to say, I mean, I have this view that, you know, Caro, when he writes a book, that's all he does for eight years. I was doing other things at the time.

• 13:21Ryan Holiday?

  I don't know how that's possible. Like, I mean, I'm a huge Caro fan and like, obviously you can see it in the book. You're like, this every sentence was sweated over and truly magnificent and obviously worth it. But I just, I honestly don't know how you could show up and work on something for 15 years, every day. I don't understand in a couple ways. Like, I don't understand, like, cumulatively that many man hours, like, how you wouldn't get done faster. Like, I just, I just can't wrap my head around it. Like, the pacing that you, the holding yourself back of it almost is impressive. And then the other thing is like, how do you have the sense of self and security,

• 14:03Ryan Holiday?

  financial or otherwise, to be like, I'm gonna work on something with no payoff for a decade?

• 14:11Speaker 01

  Well, that part would be hard for me, but the actual continuing to try to like, improve it, you know, sort of even incrementally all the time.

• 14:19Ryan Holiday?

  Yeah.

• 14:20Speaker 01

  So this book is finished.

• 14:21Ryan Holiday?

  Yeah.

• 14:21Speaker 01

  Now, like, it's there in print. And I still think about, I want to make this sentence better. I wish I had added this little thing. The other day, literally somebody emailed me about something and I was like, shit, you're right.

• 14:37Ryan Holiday?

  Yeah.

• 14:38Speaker 01

  I forgot and I was even thinking about that at one point. Maybe if I had just added one little hint towards that, it would have done something to the, to the reader in some other way. So I could see a sort of an obsessive nature to it. And frankly, if I didn't have a publisher that was telling me, you know, we would like to publish it this fall.

• 14:57Ryan Holiday?

  At some point, yeah.

• 14:59Speaker 01

  I think I probably would have taken even more time.

• 15:02Ryan Holiday?

  No, I think that's it. You have to become so obsessed by it that you live in a world where, yeah, each one of those, like, I've got to imagine for someone like Robert Caro or David McCullough or whatever, where they're like, they spent three weeks on this sentence. Or something, or like, just over and over and over again. And like, that's probably incredibly satisfying and torturous at the same time.

• 15:28Speaker 01

  So I don't know about you. For me, when I'm writing, whatever goes down on the page the first time, I can only really upgrade by one letter grade through editing unless I start over. So it's like an anchoring situation. So if it goes down on the page as a B, I can get it to an A. If it goes down on the page as a C, it will never get better than a B unless I start over. And it's usually because there's something imprecise or wrong conceptually about either the idea or the language. And I sort of trap myself in some way that I'm unhappy about.

• 16:11Ryan Holiday?

  Yeah.

• 16:12Speaker 01

  And I say that only because I know some people who sort of splatter, what I call this, they splatter on the page and then they're, they're, they think they're just gonna like, fix, fix, fix, fix, fix, fix, fix.

• 16:21Ryan Holiday?

  Yeah.

• 16:21Speaker 01

  I'm incapable of that. And as a result, it sort of can also hold me back in a way because I'm sometimes, like, the gears are turning for too long about what I even want to put on the page.

• 16:45Ryan Holiday?

  I wonder if part of that is that, like, a lot of those old school guys, they do it on a typewriter. So I really do think they're forced to put it on the page multiple times. Like, they write it longhand and then there's this, so there's this process of transferring and writing and rewriting that I wonder if actually is an advantage in how inefficient it is? Because, like, sure, I mean, you could very easily fix that sentence because you could delete it or redo it, but you, there's something- It's weirdly more permanent despite its impermanence because you're not, you're never going to retype the sentence. Like if you had to retype your book multiple times.

• 17:22Speaker 01

  Right.

• 17:23Ryan Holiday?

  You would have a different sense of the rhythm of it. It would be coming in like, do you do, did you do the audiobook for this?

• 17:28Speaker 01

  I did.

• 17:28Ryan Holiday?

  So like, that's a weird, I did, I've done five audiobooks, I think, in this room. My publisher hates it because I am like sending significant notes back. When it's supposed to be done, like you do the audiobook like a month before it comes out.

• 17:42Speaker 01

  I had the experience, just had the experience you had, I'd never done it before.

• 17:45Ryan Holiday?

  Yeah.

• 17:46Speaker 01

  And I found a whole bunch of things that I was not pleased with myself about. This was nobody else's fault, it was my own.

• 17:52Ryan Holiday?

  Yeah.

• 17:53Speaker 01

  I was able to make a couple of changes, but frankly, I couldn't make too many changes because sort of the.

• 17:59Ryan Holiday?

  They have to redesign the whole thing.

• 18:01Speaker 01

  Yes, the train was leaving the station.

• 18:03Ryan Holiday?

  I will say, having done this a lot of times, they always make it seem like it's too far gone. And that's only because it means work for them.

• 18:14Speaker 01

  Have you ever, because I've been thinking about this even recently. Have you ever updated a book just in the Kindle form before, or before a second printing or something?

• 18:22Ryan Holiday?

  So what I did, I did the audiobook and a lot of the things you notice to be like, I say the word, I don't know, astonishment, three times on the same page. I just never noticed that because, you know, for most of the time I was writing it, it wasn't on this page. The page was bigger or smaller, you know? So you're, you're just seeing things. I remember when I did Daily Dad, I read it and I was like, every sports example in the whole book, I'm saying soccer for some reason, like, because I wrote it in pieces and then it came together. And it's like, I just, I have to like be, I had to write to the, the editor and be like, look, I don't really care that much, but like, you got to swap, if there's 50 soccer mentions, like 10 of them have to become basketball and 10 of them have to become baseball.

• 19:05Ryan Holiday?

  And then let's throw in another couple of weird sports and then let's balance this out. There are just things that you wouldn't notice until you found yourself saying soccer practice a lot over the course of four days. But they're usually go like, hey, like we've already printed the first however many thousands of copies. So this can be. In the second edition, but you can go up in the in the ebook right now. So they can definitely do that, but they I'm sure I do with when people want me to do stuff. I'm like, that's not possible, you know, because you're really just trying to gauge how adamant they are about wanting it to happen or not. But so, OK, so I'm just curious about your schedule because you must have to get up incredibly early for.

• 19:44Speaker 01

  So I wake up at 4:30 ish.

• 19:47Ryan Holiday?

  Yeah.

• 19:47Speaker 01

  By the way, which is late in morning TV land.

• 19:49Ryan Holiday?

  Yeah.

• 19:50Speaker 01

  I usually work on Deal Book, which is this newsletter that I published for the New York Times before then, before the show starts at 6.

• 19:57Ryan Holiday?

  OK.

• 19:57Speaker 01

  So I'm usually sort of doing last minute little changes and things to it.

• 20:01Ryan Holiday?

  So you're up at 4:30 and you're on live television by 6?

• 20:05Speaker 01

  Yes, so it's a race. It's a sprint. I only live about 10 minutes from the studio, so that's not so hard. And I do the makeup as if I'm in a pit stop at the NASCAR, whatever. And then I do the show till 9:00 in the morning, three hours. But it goes by so quick, you don't even know. And it's like having breakfast with some of the most interesting people in the world and basically asking people whatever you want.

• 20:30Ryan Holiday?

  Yeah.

• 20:31Speaker 01

  Including people like you, which is.

• 20:33Ryan Holiday?

  Yeah.

• 20:33Speaker 01

  And then I spend a lot of the day planning and writing and editing and, you know, Deal Book, you know, we publish Deal Book six days a week.

• 20:44Ryan Holiday?

  Do you go home and work from home or do you go to an office?

• 20:46Speaker 01

  What do you? So the New York Times office is literally just a couple of blocks away.

• 20:50Ryan Holiday?

  Right.

• 20:50Speaker 01

  I often go there. Sometimes I go home. If I need to do real writing, I need to go home. The pandemic did something very bad to my brain. I used to be able to sit, we have a big newsroom with, you know, cubicles.

• 21:05Ryan Holiday?

  Yeah.

• 21:05Speaker 01

  I used to be able to write just about anything there and fast. Pre pandemic.

• 21:10Ryan Holiday?

  Yeah.

• 21:11Speaker 01

  For some reason, working practically from home for, I don't know, six months a year, I don't know if I became spoiled or what. I have a door at home, so I can be, you know, I can be in a room that's quiet by myself, even when I have my kids around.

• 21:25Ryan Holiday?

  Sure.

• 21:26Speaker 01

  By the way, sometimes I even have my daughter who, you know, I think actually sat on the floor while I was writing a lot of this book, you know, in late afternoons. But anyway, so as a result, when I have to do like what I call real writing,

• 21:36Ryan Holiday?

  Yeah.

• 21:37Speaker 01

  I either commandeering like a conference room at the office or I go home.

• 21:41Ryan Holiday?

  Okay.

• 21:42Speaker 01

  And then sometimes, you know, late afternoons, I would write the book, maybe into the night, I would write the book. If I went on trips, I'd write on airplanes, you know, obviously I'm constantly, you know, trying to go to various different libraries all over the country to,

• 21:56Ryan Holiday?

  Yeah.

• 21:56Speaker 01

  sort through things. I had a researcher very early who really actually taught me how to use a library. She'd just graduated from Princeton with a PhD in American Studies and that was super helpful. And then there was a period of time during the pandemic, actually, where I wasn't sure the pandemic was ever going to end. And I was worried I wasn't going to be able to get all the material because you weren't allowed in a lot of these places.

• 22:18Ryan Holiday?

  Yeah.

• 22:18Speaker 01

  So I would befriend actually with the help of this other researcher at different librarians, find out what kids, students were allowed in the libraries because they had their dissertation due. And then I would literally pay them. I would say, go find, you need to find box 152.

• 22:35Ryan Holiday?

  Yeah.

• 22:35Speaker 01

  I need you to take your iPhone and take a picture of every single page in the box.

• 22:40Ryan Holiday?

  Yeah.

• 22:40Speaker 01

  Happily, I was able to go back to a lot of those libraries afterwards, but I wasn't sure I'd ever, I didn't know what was going to happen.

• 22:45Ryan Holiday?

  Of course. Okay. So as I imagine you both have, you have a lot of constraints in that you have like the show is this time to this time and you can't really be doing-

• 22:52Speaker 01

  Yes, but it's a forcing mechanism for me. It's a, meaning I would say to myself, I have two hours and I really, there's no procrastinating. It's two hours. You know, I know some people, you know, use timers and the Pomodoro technique and all of these things. This is like my version of that. This is like, you have two hours, you have to use all two hours. Having said that, a lot of times, the two hours would go by and I wouldn't have a lot of actual writing done, but I would have maybe figured something out in my head.

• 23:21Ryan Holiday?

  Yeah.

• 23:21Speaker 01

  Meaning this character is going from here to here and I wasn't sure how I was getting them there from one place to the other. What was the transition? Or is there something else I was supposed to put in between it? A lot of it was, by the way, still going through research and documents.

• 23:34Ryan Holiday?

  Getting a document might be-

• 23:36Speaker 01

  The documents was it.

• 23:36Ryan Holiday?

  The whole day. That's a day's work, but it actually is way more valuable than having written 15 pages.

• 23:42Speaker 01

  Completely. And sometimes it was even- Rereading things. So I also scanned, anytime I'd go to a library, I'd literally use my phone and I would take pictures of, I mean, tens of thousands of pages and I literally created like a Dropbox system. Unfortunately, AI was too late for me in this project.

• 23:59Ryan Holiday?

  To translate them?

• 24:00Speaker 01

  Because I didn't really have true OCR, meaning like to be able to like make them searchable.

• 24:04Ryan Holiday?

  It's not, just to, just to help you with that. It's not, because I'm in the middle of doing a very research-heavy book right now. It's not really that usable. Like, you think it would be and then you're like, you know what? I need to have a person do this. Like, you can't trust it. You think you'd be able to trust it and you can't. That's really the problem. Especially, I can go through a lot of handwritten letters right now.

• 24:25Speaker 01

  That's what I, a lot of it is handwritten.

• 24:26Ryan Holiday?

  And it's like, I just can't, I can't, it hallucinates 30% of the time. You know what I mean? It's just not good. So it's still, it would be wonderful if there was some shortcut that made it magically better, but I don't think.

• 24:37Speaker 01

  But I found myself even finding stuff three and four years later, meaning documents that I had found in 2018.

• 24:46Ryan Holiday?

  Yes.

• 24:47Speaker 01

  That I thought I had read and understood. And then two or three years later, because I had gone back to them, because I needed something from one of them, I'd see something and go, oh shit.

• 24:57Ryan Holiday?

  Yes.

• 24:58Speaker 01

  That, I forgot about that. Or I didn't realize that. Or I hadn't connected the dot between something there and some new document that I had found that really explained what these two characters were really doing with each other.

• 25:09Ryan Holiday?

  Yeah.

• 25:10Speaker 01

  And those were the moments where I would have a smile on my face during this project, where I felt like, oh goodness, this is, now this is gonna work.

• 25:30Ryan Holiday?

  That's a philosophical paradox, like I think Plato was talking about this, where it's like, how can you be looking for something if you don't know what it is? Like, how are you knowing that you found it if you've never seen it before, right? It's like this paradox of you're searching for something you don't know and yet you're like, I found it, right? Like, I'm struggling with this myself because you're going through the documents, trying to learn about this thing, and then it's not until you've gone. On through all the documents that you know which of the documents you needed.

• 26:00Speaker 01

  Right.

• 26:01Ryan Holiday?

  Right? So you're like, or there's just allusions and references in the letter like.

• 26:05Speaker 01

  Yes.

• 26:05Ryan Holiday?

  You're like, oh, this person was, they were talking about this thing and these letters are 16 years apart or whatever. And you're reading it and you're like, this one's not interesting. This one's not interesting. This one's not interesting. And then months later, you're like, oh, they mentioned this.

• 26:20Speaker 01

  Right.

• 26:21Ryan Holiday?

  Most interesting thing. The whole book is pivoting around in this letter that I put in the don't need pile.

• 26:26Speaker 01

  Exactly. That's, that happens a lot.

• 26:28Ryan Holiday?

  Yeah.

• 26:29Speaker 01

  And I think even just trying to understand the characters, it took me years to really feel like I understood them. So there's this guy Charlie Mitchell, who's the main character. For a very long time, I don't think I understood what really motivated him. Like, what was the hole that he was trying to fill?

• 26:47Ryan Holiday?

  Yeah.

• 26:48Speaker 01

  What was that insecurity thing that he, you know, was, what was he trying to prove to himself or to somebody else?

• 26:54Ryan Holiday?

  Yeah.

• 26:55Speaker 01

  And I think I was looking for, I was looking for those things in all the characters, but I, some of those things did not reveal themselves to me. For a very long time. And it wasn't until I sort of had some of those breakthroughs where then I felt like I could then set the character up. In a way so that when they did things later on, as the reader, you could understand where it was coming from. Even if you thought that they were wrong or it seemed completely irrational. When you understand sort of them as people, all of a sudden things, well, they may not be right. They no longer seem as completely irrational.

• 27:30Ryan Holiday?

  It's consistent and logical to them.

• 27:33Speaker 01

  To them.

• 27:34Ryan Holiday?

  Yeah.

• 27:34Speaker 01

  Exactly.

• 27:35Ryan Holiday?

  That must be what takes Robert Caro so long, right? Like he's, most of it is just figuring the person out. And the different people out over the course of all those years, like the essence of it.

• 27:47Speaker 01

  Always, I mean, at least for me, I'm always, I do this in, I think in my reporting today with people who are alive. But in this case, people who were alive 100 years ago, trying to put myself in their shoes and trying to think through, okay. You know, why did they think what they think? By the way, certain things that they were doing then today would be completely illegal. You would think

• 28:09Ryan Holiday?

  Yeah.

• 28:09Speaker 01

  clearly immoral. We would, you know, be very judgmental about those things. And I would try to think, okay, well, is there some level of empathy that I can have for them? Also, sort of given the distance of today and then try to think, how did they rationalize and justify these things to themselves? Because invariably, they would have had you somehow.

• 28:31Ryan Holiday?

  You know, like the complicated contradictoriness of the, like this, the senator who's both like the guy who's like, the banking system is rigged and it's fucking over the little guy.

• 28:41Speaker 01

  Right.

• 28:42Ryan Holiday?

  Is also like fucking over the little guy.

• 28:44Speaker 01

  Yes.

• 28:44Ryan Holiday?

  If they have a different skin color. So like, how do you wrap your head around this sort of moral kind of compass and commitment with this? You know, this sort of worldview that's so impossible to wrap your head around that that complicatedness of people is hard.

• 29:00Speaker 01

  And I think, by the way, you're talking about Carter Glass, who was a senator in Virginia, who's sort of responsible for, to some degree, the creation of the Federal Reserve and then later breaking up the banks, who was a racist. I mean, a true racist.

• 29:13Ryan Holiday?

  A segregationist and not like, oh, it's the old ways. But it's like, no, no, I want to steal. I want to disenfranchise black people. That's my main reason for being a politician.

• 29:22Speaker 01

  Completely.

• 29:22Ryan Holiday?

  Yeah.

• 29:23Speaker 01

  And yet, by the way, today, he's sort of held up by probably, you know, the most progressive left as some kind of, you know, great bastion of, you know, regulating the banks.

• 29:35Ryan Holiday?

  Because his name is on, we don't know him, we just know the name on the bills.

• 29:38Speaker 01

  Exactly.

• 29:39Ryan Holiday?

  Yeah.

• 29:39Speaker 01

  But I think back then, he divided his brain. I don't think he thought of these things in the same context.

• 29:45Ryan Holiday?

  Yes. When you realize the time it takes to like actually get into someone's brain and the logic of why they're doing it, there's something about that that journalism is just fundamentally incapable of doing because of the rapidness of it. It's like the first draft. It's like, by nature of it being a first draft of events.

• 30:05Speaker 01

  Yes.

• 30:05Ryan Holiday?

  It's not considering most of the things that make for an amazing book.

• 30:11Speaker 01

  Yeah, but I do think, or at least I tell myself this. I like to believe that having now reported on this world of sort of business and policy leaders for so long, and then also in the context of the crisis of 2008. That I tell myself that it's sort of like keyed me in to the way people like this think and the different kinds of emotional reactions that they were having and like the way they approached certain moments and that that's sort of educated me in terms of then how I at least approached or thought about the reporting about these other people, meaning what kind of material did I need to go find? Oh, they would likely would have been doing X. I need to go find out, were they doing X?

• 30:55Ryan Holiday?

  Yeah.

• 30:55Speaker 01

  Were they thinking that? Were they not thinking that? I gotta, I gotta go see how, how similar or different they are. And the truth is, I guess, one of the big lessons for me is, we're all the same.

• 31:05Ryan Holiday?

  But I mean, in the present moment, the reporters like so and so said this.

• 31:09Speaker 01

  Yes.

• 31:10Ryan Holiday?

  This happened. They're not like, let me think about their childhood and let me, you know, like it's, it's this sort of snapshot and it's not the sort of all the factors swirling around. And it's just, it's weirdly, it's like the books, like when you read history, it's like you actually know what's going to happen. So you'd think it could be more black and white, but actually great history is gray and it shows you, like David McCullough talks about how the one thing you can never forget when you're writing history is that they didn't know.

• 31:40Speaker 01

  They didn't know.

• 31:40Ryan Holiday?

  It was gonna happen.

• 31:41Speaker 01

  It's never black and white. But I do think there are some reporters, I was thinking of Peter Baker at the New York Times or Maggie Haberman, who I think actually write daily journalism that because they're so steeped in it and have covered these people as long as they have, there's sometimes these little hints and things in certain sentences contextual that that sort of gets you to understand why some of these things may be happening, even when you think the whole thing is crazy.

• 32:09Ryan Holiday?

  But even that, it's not that they're the exception that proves the rule, but that is what happens when you have 20, 30, 40 years on a beat.

• 32:17Speaker 01

  Yes, exactly.

• 32:17Ryan Holiday?

  And, and so they're churning out breaking news, but it's like the tip of the ice or it's the, you know, the inverted iceberg thing or whatever that Hemingway was talking about. And we don't necessarily celebrate that as the virtue or set people up to be in that position.

• 32:33Speaker 01

  Right.

• 32:34Ryan Holiday?

  They're almost like remnants of the old system.

• 32:36Speaker 01

  Well, look, I've been covering the same thing for now thirty years. Peter and Maggie have probably similarly, but you're right. For whatever reason, in journalism, most people go from beat to beat to beat. They sort of do two or three or four years in one beat. And then they jump to another thing and another thing and another thing. And arguably, they come maybe a lot more well rounded than I am, for example.

• 32:57Ryan Holiday?

  Yeah.

• 32:58Speaker 01

  But it's harder to be super deep as a result.

• 33:01Ryan Holiday?

  And what I meant about your schedule, so on the one hand, you have a lot of constraints, like the show takes this long. And then you have this to get out and whatever. But then you also probably have a lot of freedom in that you sort of can decide how you want to do things. Are you just like winging it day to day? You're like, you know, today I want to go work from home or today I want to go work for the New York Times.

• 33:20Speaker 01

  No, I map it out. I map it out, meaning because also I'm traveling oftentimes for work. I would sit with a calendar and I can usually tell you for, you know, a given couple of weeks at a shot, maybe even longer. Like this, like this afternoon, I'm probably going to work from home.

• 33:36Ryan Holiday?

  Yeah.

• 33:36Speaker 01

  This morning, I have meetings at the office. This day I'm doing this, this day I have to be so, you know, this weekend, I would even write on the weekends. My calendar is like, there's a phrase productivity hackers use, blocking.

• 33:50Ryan Holiday?

  Time blocking?

• 33:51Speaker 01

  Time blocking.

• 33:51Ryan Holiday?

  Yeah.

• 33:51Speaker 01

  I'm a big time blocker.

• 33:53Ryan Holiday?

  Okay.

• 33:53Speaker 01

  So if you were to look at my calendar for many years, there would be lots of nineteen twenty nine in orange.

• 34:01Ryan Holiday?

  Yeah.

• 34:01Speaker 01

  In boxes.

• 34:02Ryan Holiday?

  Okay.

• 34:03Speaker 01

  And those were my boxes. And so I knew Saturday afternoon, I was, you know, from one to five, nineteen twenty nine.

• 34:12Ryan Holiday?

  Wow.

• 34:13Speaker 01

  That's what it's going to be. But it would also say morning, you know, taking my daughter here and, you know, lunch with my kids or my other son plays tennis. We got to go. By the way, I would take him to play tennis and he might be taking a lesson and I'd be sitting there with my laptop.

• 34:29Ryan Holiday?

  Yeah.

• 34:29Speaker 01

  Working on nineteen twenty nine.

• 34:31Ryan Holiday?

  Yeah, or you're reading documents or yeah. So theoretically, you could go back to your calendar and add up the hours.

• 34:37Speaker 01

  I've thought about doing that. I, I'm too scared to put my calendar into chat GPT, but I actually thought that it would do a better, it would make it a lot easier to actually map it all out. But I have it for years. So yes, I could, I could see, it would clearly be thousands of hours, but I don't know what it would ultimately.

• 34:53Ryan Holiday?

  Yeah, I wonder if you would be proud of the number or you'd be like, oh, I thought I worked on this more.

• 34:58Speaker 01

  Yeah, I don't know. I think my wife would say that I probably did it super inefficiently. And she's probably right because there were days where even though I told myself, gotta do it, gotta do it.

• 35:07Ryan Holiday?

  Yeah.

• 35:07Speaker 01

  That I would have these moments where I'm doing the reporting or the research and I couldn't find the thing. Oh, by the way, that would happen all the time. I thought of something that I knew that I needed. I thought I even saw it like two years earlier.

• 35:19Ryan Holiday?

  Yes.

• 35:19Speaker 01

  It would take me two or three days to find it.

• 35:21Ryan Holiday?

  This is research assistance. You need to have a second person who can be like, we have something like that, right? You need to have a document fetcher.

• 35:28Speaker 01

  Yes. For about a year, I had a researcher who I worked with who was who was super helpful. But as the project continued and just obviously metastasized, I was sort of on my own.

• 35:37Ryan Holiday?

  That's the tough part is is the it'd be wonderful if everything was neatly organized, but you can't do that because you're doing other things in your life.

• 35:45Speaker 01

  Right.

• 35:46Ryan Holiday?

  Do you feel like that's the thing you get lit up by doing and all the other things are distractions? Or do you think they all kind of feed into it?

• 35:54Speaker 01

  Oh, the truth is they all feed each other. So squawk box in the morning feeds the way I think about my reporting all day.

• 36:02Ryan Holiday?

  Yeah.

• 36:03Speaker 01

  A lot of the reporting all day feeds what I do on television. Working on all of those things, I think fed a lot of what ultimately ends up in the book. I mean, a lot of all of the nonfiction work I've done helped me when I was involved in things like billions and other things to think about sort of worlds. So yeah, it probably looks or feels like I'm doing a lot of things, but to me, they're all sort of in the same vein.

• 36:29Ryan Holiday?

  Yes.

• 36:30Speaker 01

  And maybe you'll think I'm ADHD because of the jumping around. It actually keeps me engaged and excited in all of them.

• 36:38Ryan Holiday?

  But is your phone just going off all the time? I feel like the hardest thing about the large blocks of uninterrupted concentration that a book like this would require would be it's sort of at odds with the sort of plugged in.

• 36:50Speaker 01

  The plugged in, there's no question that you're texting people back.

• 36:54Ryan Holiday?

  Yeah.

• 36:54Speaker 01

  Back and forth. I have reporters that work on my team. I got to call them back. I'm editing their work. They're.

• 37:00Ryan Holiday?

  Right.

• 37:00Speaker 01

  Giving me tips. I'm giving them tips for sure. And that was the thing that probably, you know, would throw me the most. I did occasionally try to use, there's now the do not disturb function on the phone. That only works to a degree. That's why weekends are great.

• 37:16Ryan Holiday?

  Yes. Well, they do not disturb prevents other people from disturbing you, but it doesn't prevent you from disturbing yourself by looking for.

• 37:23Speaker 01

  By looking for it, yes. I, yes, I, I fully cop to that problem.

• 37:27Ryan Holiday?

  No, that, that's the, I'm like, don't, don't call me. And then I'm like, I'm not using this two hour block. I'm using 30% of it because I dicked around for a large chunk of it.

• 37:41Ryan Holiday?

  Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us and it would really help the show. We appreciate it and I'll see you next episode.