The Daily Stoic - Why Andrew Ross Sorkin Spent 8 Years Chasing One Story

Episode Date: December 3, 2025

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 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, a financial news service published by The New York Times. He wrote the bestselling book Too Big to Fail 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. You can grab signed copies of 1929 by Andrew Ross Sorkin at The Painted Porch: https://www.thepaintedporch.com/Follow Andrew Ross Sorkin on Instagram @SorkinSays and on X @AndrewRSorkin 🎥 Watch the video episodes on The Daily Stoic YouTube channel: https://www.youtube.com/@DailyStoic/videos🎙️ Follow The Daily Stoic Podcast on Instagram: 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🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us: Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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descriptions to make those ads go away. 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. 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 I'd get in. And we forgot that there was a huge car festival in fast trip.

The whole main street was blocked. They were very loud, classic cars up and down the road. there was a snow cone or a lemonade stand in front of the Daily Stoak Studios. Actually, that's something we've been doing. We took this storefront offline. It used to be a barbershop, 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 this 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, it set up like this lemonade, snow cone vendor person, so they were doing their thing. And I was like, oh, my God, 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. We were 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 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 markets at an all-time high. Things are going amazing. It's time of peace, prosperity mostly, and then the music stops. Maybe it takes a couple 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 of the Second World War. It led to in many ways that reinvention, the reticulation of the social contract here in America, 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 Soros. 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. I was 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 going to wait.

I was going to savor it. It's a big book. And then found out he was coming. I said, all right, can I read this book in 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 going to 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. It's the co-anchor of CNBC's Squawk Box.

He is the founder and editor of Deal Book, which is a financial news service published by The Times. He wrote the best-selling book, Two Book to Fail, co-produced a movie adaptation of it for HBO. It'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 going to like this episode. Thanks to Andrew for coming out.

I wanted to split it up because it was such a great episode. episode, and let's get into it. I feel like the best question to start with is probably one you've never been asked. Please. Which is, so do you think we're in the middle of a bubble right now? You and Leslie Stahl. How many people have asked you that? I'm actually more interested in how often you've been asked that question on this book tour

than the actual answer. Oh, invariably, almost every time. Right. So, yeah, dozens of times. And people think probably that it's a somewhat original question. 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. I don't want to read the book. Just tell me do I need to be worried. Pretty much. Yeah. Give me the clip. The clip notes version is, should I sell everything I own?

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. The same thing. 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? Oh, like in that, you lost your bearings completely. I was so lost. Yeah. I happened to be in London. Yeah. So I think the time difference got me.

And I was like, did I just say? Now, happily, I had not said it prior. Right. I mean, in this particular, I had said it prior or something similar. So, yes, you are right. That's a thing. 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. Oh, clothing.

Yes. You're, like, outfit tracking yourself because, like, you don't want it to seem like you own one shirt. This is true. I, you know, I wear a lot of suits because I want to be, 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 for me

this is actually how I like to dress up for your stuff. This is like how I like to dress but yeah do I have to dress up?

I think people think on that on squat box in the morning that we should be wearing ties. Why? Who cares? 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. 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 to. I was like, whoa. You look good.

I thought you're all right. You're always looking good. 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 squat box? Like, no, no, no, no, no. I actually find writing, okay, a couple things because I love watching you and listening to you talk about actually about the craft of writing. Okay. I find writing very hard. Sure. Like super hard. Yeah. 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 blow. I, lock 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.

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'm writing a night, airplanes without Wi-Fi, always turn the Wi-Fi 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? Right. And I would say, I'm writing the book and enjoying myself. Yes.

And they couldn't contemplate how that could be a vacation. No, this is the thing that I don't get to do because of my jobs. Right. And it's what I actually like to do. 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. I was just trying to figure it out. Yeah.

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 acknowledgments, you took a bunch of books about the crash on a vacation. Yeah, that's how it started. I 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 like, that's the part that's just for you. But the truth was, I was scared the whole time. Of writing it? Well, two things.

I was scared that I wasn't going to be able to find the kind of granular detail that I needed to make each character pop in a consistent way. Sure. 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 going to either I was going to find it in some art. archive somewhere, or it just doesn't exist. It's a different kind of reporting that you hadn't really done before. Totally.

It was completely new to me. I mean, even just learning my way around the 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 when I wrote Too Make 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. 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, like about whether you can actually do this for real. Also, if it's not intimidating, it probably means you're not doing anything good. But I also think I was so scared because I thought that book worked. I didn't want to do something.

didn't work. Yeah. So it's sort of like, 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. The tricky part there is that it's a bar that you don't actually control. Right.

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 because you don't control what's happening in the world, then you don't control what other people think about what you do. Right. No.

So that's scary. Yeah. 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. You worked on it for 10 years? More like eight-ish. And the truth is, on and off. There were periods of time where I was like full peddled to the metal.

Yeah. And then there were periods, especially we had the pandemic, 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. Yeah. 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. 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 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, financial or otherwise, to be like, I'm going to work on something with no payoff for a decade?

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. Yeah. So this book is finished. Yeah. 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.

Yeah. I forgot. And I was even thinking about that at one point. maybe if I 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. At some point, yeah.

I think I probably would have taken even more time. 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 McCuller or whatever, where they, 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. 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. Yeah. 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. Yeah.

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

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it's impermanence because you're not you're never going to retype the sentence like if you had to retype your book multiple times right you would have a different sense of the rhythm of it it would be coming in like do you do did do the audiobook for this i did 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 Just had the experience you had I'd never done it before. And I found a whole bunch of things that I was not pleased with myself about this was nobody else's fault with my own.

I was able to make a couple of changes, but frankly, I couldn't make too many changes because sort of the... They have to redesign the whole thing. Yes, the train was leaving the station. I will say, having done it 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. Have you ever, because I've been thinking about this even recently, have you ever updated a book just in the Kindle form before a second printing? No, like, so what I did, I did the audiobook. And a lot of the things you notice would 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 small, 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 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, and then let's throw in another couple weird sports,

and then this balances 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 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 ebook right now. So they can definitely do that. But I'm sure I do when people want me to do stuff, I'm like, ah, it'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, okay, so I'm just curious about your schedule because you must have to get up incredibly early for swap. So I wake up about 4.30-ish, by the way, which is late in morning TV land. Yeah. I usually work on Deal Book, which is this newsletter that I published for The New York Times before then. Before, the show starts to six. Okay. So I'm usually sort of doing last minute little changes and things to it.

So you're up at 430 and you're on. live television by six. 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 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, including people like you, And then I spend a lot of the day planning and writing and editing and, you know, deal book, you know, we publish dealbook six days a week. Do you go home and work from home or do you go to an office? So the New York Times office is literally just a couple blocks away. Right. 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. I used to write just about anything there and fast pre-pandemic. Yeah. 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 in a room that's quiet by myself, even when I have my kids around. Sure. 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, I either commandeer like a conference room at the office or I go home. Okay. 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, I was constantly, you know, trying to go to various different libraries all over the country to, you know, sort through things. I had a. researcher very early who really actually taught me how to use a library. She just graduated from Princeton with the 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 on material because you weren't allowed in a lot of these places. Yeah. 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 do. And then I would literally pay them. I would say, go find, you need to find box 152. Yeah. I need you to take your iPhone and take a picture of every single page in the box. Yeah. 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. 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. 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. Yeah.

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. or 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. Getting a document might be the whole day. That's a day's work, but it actually is way more valuable than having written 15 pages. 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. I mean, it did tens of thousands of pages and I literally created like a Dropbox system. unfortunately AI was too late for me in this project to translate them because I didn't really have true OCR meaning like to be able to like make them searchable properly 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 I 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'm going to do a lot of handwritten letters right now Yeah, no, that's what I, a lot of it is handwritten. 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. Interesting. So it's still, it would be wonderful if there was some shortcut that made it magically better, but I don't think. But I found myself even finding stuff three and four years later, meaning documents that I had found in 2018.

Yes. 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. Yes. 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. Yeah. 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 going to work. So we live on a Halloween street. We knew it was a Halloween street when we moved there. And then it has quickly become a Thanksgiving and then a Christmas street. Everyone's vying to outdo each other with their decorations. And I'll admit it sneaks up on us, especially as the competition gets more and more. The holidays are here. And if you're looking for holiday decor or last minute refreshes around the house, get what you need fast with Wayfair. where we got a bunch of our Christmas decorations and a bunch of essentials because we have some of my wife's family visiting us for the holidays, blankets, linens, all that kind of stuff. You can get all of it at Wayfair. You can also get big stuff like sofas and dining tables, beds,

desks, and more all shipped for free. They don't have huge delivery fees for furniture. Find all your must-haves from furniture and decor to appliances and cookware all in one convenient place. Get last-minute hosting essentials, gifts for all your loved ones, and decor to celebrate the holidays for way less, head to Wayfair.com right now to shop all things home. W-A-Y-F-A-I-R-D-com, Wayfair, every style, every home. 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 if 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 through all the documents that you know which of the documents you needed. Right. Right. So you're like, or there's just allusions and references in the letter. Like, yes. 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 most interesting thing. The whole book is pivoting around in this letter that I put in the don't need pile. Exactly. So that happens a lot.

Yeah. And I think even just trying to understand the characters 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? Yeah. What was that insecurity thing that he, you know, what was he trying to prove to himself or to somebody else?

Yeah. And I think I was looking for, I was looking for those things in all the characters, but 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 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. It's consistent and logical to them.

To them. Yeah. Exactly. That must be what takes Robert Carrow 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 always I mean at least for me I'm always I do this and I think am I reporting today with people who are alive but in this case people who were live

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 yeah 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 to somehow. Yeah, like the complicated contradictoriness of the, like, the senator who's both like the guy who's like, the banking system is rigged and it's fucking over the little guy. Right.

is also like fucking over the little guy 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 complicatedness of people is hard. 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. a true race 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 completely yeah 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 because his name is on we don't know him we just know the name on the bills exactly yeah but I think back then he divided his I don't think he thought of these things in the same context. 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, it's not considering most of the things that make for an amazing book. 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 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 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 likely would have been doing X.

I need to go find out, were they doing X? Yeah. Were they thinking that? Were they not thinking that? I got to go see how similar or different they are. And the truth is, I guess, one of the big lessons from me is we're all the same. But I mean, in the present moment, the reporter's like, so-and-so said this. 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.

They didn't know. It is always gray. It's never black and white. But I do think there are some reports. 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, contextually, that sort of get you to understand why some of these things may be happening, even when you think the whole thing is crazy. 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. Yes, exactly. 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. They're almost like remnants of the old system. Well, look, I've been covering the same thing for now 30 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 and 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. Yeah. But it's harder to be super deep

as a result. And what I meant about your schedule is 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 and 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 from the New York Times. 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, given a couple of weeks at a shot, maybe longer. Like this afternoon, I'm probably going to work from home. Yeah. 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, time blocking. Yeah. I'm a big time blocker. Okay. So if you were looking at my calendar for many years, there would be lots of 1929 in orange in boxes. Okay. And those were my boxes.

And so I knew Saturday afternoon, I was. you know, from one to five, 1929, 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. Yeah. Working on 1929.

Yeah. Are you reading documents? Right. Yeah. So theoretically, you could go back to your calendar and add up the hours. I've thought about doing that. I'm too scared to put my calendar into chat GPT, but I actually thought it would make it a lot easier

to actually map it all out. But I have it for years. So yes, I could see. It would clearly be thousands of hours, but I don't know what it would ultimately. Yeah, I wonder if you would be proud of the number or you'd be like, oh, I thought I worked on this more. 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, got to do it, got to do it. 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.

Yes. It would take me two or three days to find it. 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. Yes. For about a year, I had a researcher who I worked with who was super helpful. But as the project continued and just obviously metastasized, I was sort of on my own. own. That's the tough part is the, it would be wonderful if everything was neatly organized, but you can't do that because you're doing other things in your life. Right. 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? 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. Yeah. 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. Yes. And maybe you'll think I'm ADHD because of the jumping around, it actually keeps me engaged and excited in all of them.

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 sort of at odds with the sort of plugged in. The plugged in, there's no question that you're texting people back, back and forth. I have reporters that work on my team. I got to call them back. I'm editing their work. They're 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. Yes. Well, they do not disturb prevents other people from disturbing you, but it doesn't prevent you from disturbing yourself by looking for things. By looking for it. Yes. Yes. I fully cop to that problem. No, 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 because I dicked around for a large chunk of it.

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. Thank you.