The Insane Productivity of Andrew Ross Sorkin

Transcript: (disclaimer: may contain unintentionally confusing, inaccurate and/or amusing transcription errors)

David: Hello, Acquired listeners. We are coming to you today with a very fun ACQ2 interview with our buddy, Andrew Ross Sorkin. We got to know Andrew over the summer for our Radio City show where we had a delightful cameo with us, and he’s got a new book—1929. He’s doing a book tour and we said, hey, do you want to come on ACQ2 given you’re doing the book tour and rather than just talking about the book, why don’t we talk about how the heck do you do all of this that you do? We’re dying just making one show. You do four things every day.

Ben: So there’s The New York Times’ DealBook, the daily newsletter, there’s the DealBook Summit, which happens every December. There’s of course that he co-created the show, Billions. He is every single morning from 6:00 AM to 9:00 AM Eastern on CNBC doing Squawk Box. He’s written Two Big to Fail and 1929.

David: Two major books, yeah. This was a very fun conversation.

Ben: Today’s conversation is a little bit how does he do it all, but also we realized Andrew’s never actually told this story before of how it all came to be. How did he start a business daily email newsletter in 2001? This is over a decade before Stratechery, I don’t know, 15 years before the era of Substack, doing it inside, now the biggest newspaper in the US (I think) in the world, and now every December doing DealBook Summit, which to me is the flagship canonical business interview forum in the world. That’s more than that. Business technology politics.

Listeners, this conversation was especially interested to David and I for naval gazing reasons, but we think Andrew’s story is just fascinating. It really illustrates the shift in the media landscape, and I am just so interested in how he maintains the quality bar that he does across such a wide, wide set of activities. Please enjoy our conversation on the insane productivity of Andrew Ross Sorkin.

Andrew, you’re wearing something different than you are wearing on Squawk Box this morning. How does that work?

David: What’s your wardrobe change throughout the day look like?

Andrew: I did that for you to be honest with you.

Ben: Really?

Andrew: Yes. Usually, I’m in a suit basically all day. I sleep in a suit with a tie. Then I thought to myself for doing this podcast, there might be video. These guys are probably going to wear sweaters or look cool and I’m going to look like some old man in a suit. I’ll put a sweater on. That’s what’s going on here.

Ben: Okay. Andrew, I’ve always thought of you as a New York Times reporter. I’ve thought of you as the founder of DealBook. You also do Squawk Box. How do you think about that? Especially since that’s over by 9:00 AM.

Andrew: It is over by 9:00 AM but it’s a full three hours, which oftentimes feels like a lot longer than that. Not in the moment; I think we have a ball in the moment. But for me it’s the way I begin my day and all the things that I try to do. In many ways I’m doing DealBook, oftentimes finishing it up even before Squawk Box starts, and then doing Squawk Box, and then going back to DealBook and going to other projects. They all inform each other in interesting ways.

About 15 years ago, I want to say, in 2011, I used to be a guest on Squawk Box often. They called me up and they said, hey, would you want to be the host of the show? I thought, that’s crazy. I can’t read a teleprompter, I’ve never done this before. This is insane.

David: Was one of the other hosts retiring? Or how did this…?

Andrew: A couple of things had happened, actually. I don’t know if you remember a legendary journalist named Mark Haines, who was the original host of Squawk Box, and then was on a show called Squawk on the Street, passed away. They were going to reshape Squawk on the Street.

Carl came to me, who was one of the three hosts of Squawk Box, was going to move to that show. They were looking for somebody to put in his chair. I thought, I love my job at The Times. I’ve been there since I was 18 years old, and they were willing to have me do the show in the morning and also allow me to continue doing a lot of the other work that I enjoy doing. I could have the best of both worlds. This would be great, and as long as I could be awake at that hour.

Now, I was always up early, so the up early was not the hard part. Though I don’t think I was up early with makeup on and lights. I was always up early because I was publishing DealBook, our newsletter, which typically was going out between seven and eight o’clock in the morning. I always did have to get up early, but I was often in my pajamas. I wasn’t interviewing people.

Ben: And if you need that time to publish DealBook, now you don’t have that time.

Andrew: Yes and no. A couple of things. The DealBook team has grown, so that actually was a huge benefit. Also, I end up spending usually about an hour in the morning before Squawk Box starts, making last tweaks and things to the DealBook newsletter. That’s actually one of the great ways that I read in as they say in the TV business, to learn about everything that’s going on as I’m doing my last licks at the newsletter to make sure everything’s in order.

David: What time are you getting up? What time is your day starting?

Ben: This is 5:00 AM to 6:00 AM now that you’re doing the last minute tweaks, 5:00 AM to 6:00 AM Eastern.

Andrew: My day usually begins around 4:30 in the morning. That’s usually when I wake up-ish, I’d say. I lie in bed with my phone under the covers looking at email, texts that came in overnight, Slacks oftentimes around DealBook and things like that. Then I’m oftentimes writing.

If you read DealBook at the top, it says good morning, Andrew here. I’m writing that in the morning, every morning. That’s because I need to see where we are in terms of what we’re going to really lean into for the top of the newsletter. Oftentimes trying to change the subject line or other things like that as we try to get more readers.

Ben: It is very clear whenever I open it up that that is a lead. That is a hook, this is a pitch to me of the rest of this newsletter is interesting. Here’s why. Read on.

Andrew: That’s the goal. If that’s working for you, knock on the wood. That’s great.

Ben: Are you sending that from the news desk at CNBC?

Andrew: No. The button is being pressed actually in Europe by two of my colleagues. Michael de la Merced who’s actually been with me in DealBook for about 20 years now, and Bernhard Warner who work overnight. He lives in Italy, actually. They’re working with a copy editor doing some of the last minute changes, and then usually we’re doing a little bit of Slacking back-and-forth in the morning before things go out.

David: They’re later in the day, they’ve had their coffee when they’re hitting the button.

Andrew: They’ve had their coffee. They’ve been fixing, adding, sometimes completely rewriting and changing the mess that we’ve made out of New York, overnight.

Ben: How do you think about the content of the newsletter? Are those stories created in service of creating a cohesive newsletter, or are you trying to create a newsletter out of the most interesting business stories of yesterday?

Andrew: Combination of both. I think for the purpose of the newsletter, we’re thinking about how we can make the reader armed and dangerous before their nine o’clock meeting, or their breakfast in the morning, or wherever they’re headed off to.

DealBook actually transformed itself over the last, we’re coming up on 25 years of doing this. In the beginning it was really for the world of deal makers. It was M&A bankers, lawyers, accountants, and people in that ecosystem. Then increasingly CEOs started to read it, board members and strategic dev groups, and then regulators and politicians started to read it.

I think we shifted our focus, especially after the financial crisis of 2008, to really try to capture the intersection of business and policy, and really connect the dots between lots of different storylines. So every morning I think we’re trying to find as much scoopy original stories, but also be able to try to take a story that’s in the news and spin it forward if we can.

Ben: We’re starting in media’s rest here. Let’s go back to the beginning. Let’s go back to the start of DealBook, the newsletter, before there was a summit. I don’t think people realize how early you were to the email game.

David: Or to The Times. You made the quip earlier in our conversation about you started when you were 18 at the time. You literally started at age 18 at The New York Times. That’s not a joke.

Ben: All right, let’s go there. How’d that happen?

Andrew: Backstory is I’m 15 years old. I got to go back three years. All I wanted to do was be in media. Not necessarily as a journalist. Actually, the business side of media was more interesting to me. I was selling ads for the school newspaper, and then ultimately created my own magazine in my high school in Scarsdale, New York called The Sports Page Magazine.

The purpose of the magazine was as much about sports journalism as much as it was about selling ads and trying to capture a particular audience. In this case, high school–aged boys, which were harder to get to than high school–aged girls at the time. The magazines would be distributed across the country inside high schools, advertisers would pay, kids would write the articles about professional sports as if they were writing Sports Illustrated.

We did it, and about a year into this project, The New York Times wrote a little article about this little endeavor. My mother used to drive me down to New York City to different advertising agencies because I’d have to go sell my ads. They were cheap. Cheap on a relative basis, like $900, $1200 for a full page ad, blah-blah-blah.

David: Yeah, but for you as a high school student, this is amazing.

Andrew: Huge. Anyway, it succeeded and failed by the time I was about 18 years old. It succeeded in that we had gotten all of these high schools to agree to take it. Some schools were getting it. Some schools weren’t. I’ll be honest. We made a whole bunch of rookie errors that a great business leader would not have. We used to send mail by Federal Express, for example, because we thought that that would make it look like we were really professional.

David: Meanwhile, your mail bills are…

Andrew: Which is a great mistake. Then we had hired a printer, actually the same printing company that was printing Wired magazine at the time. We were supposed to drop ship. We were moving from black and white to full color, and we totally just misestimated what the cost was going to ultimately be, and that was the end of that. But it was one of the great educations of my life.

As a result it helped me (I think) get my little foot in the door of The New York Times. When I was 18 years old, I used to read a guy named Stuart Elliott, who was the advertising columnist at The New York Times. He was like a god to me.

Most people read the front page of the paper, the sports section. I would go to page C6 to read what Stuart had to say, so I could go down to these meetings with the advertising agencies and pretend like I knew what I was talking about. All I wanted to do was work for this guy.

I was trying to find all these different ways to get into The Times and get to him. I used to go home during high school and call him on the telephone, to try to get a gig. Then finally he took me out to lunch, and somehow convinced him to let me stay.

Then there was a guy named Glenn Kramon who was running the business section, and he let me stay. I used to come every day with a visitor pass. There’s a union at the time. They didn’t really like this whole idea, so they didn’t really know about it, actually. I just would come every day and I’d stand. I’d xerox and staple. I had no intention of putting two words together, let alone a sentence.

This is 1995. Happily, an editor who had no idea how old I was—I was wearing a suit with a tie back then—she thought I was a real person and she assigned me a story to write. And that’s how it all started.

Ben: No way. A mistaken identity thing is how you wrote your first piece at The Times.

Andrew: I think she thought I was a young, maybe newsclerk graduate from college. She overheard me talking about this thing called the Internet back in 1995. She thought, oh he may seem to know what’s going on.

Ben: Do you remember the piece?

Andrew: Oh, absolutely. It was the silliest piece, but I love it so much. You’re going to laugh. It was a piece about the noise that modems make back when we used to… Well, we actually used to write the word ‘modem, a device that transmits data over a phone line,’ and all these adults…

David: Well, now you need that again. Nobody knows what it is.

Andrew: Nobody knows. My kids don’t know what a modem is. She wanted to understand what that noise was, that high-pitched noise. I was trying to explain to her that the noise was, they were mating. The two modems were talking to each other. That was the first article out of the gate.

David: Wow. So did you start full time?

Andrew: No, sorry. I went to Cornell, I was going to be a camp counselor that summer, and then they asked me to stay for the rest of the summer. Then I went off to Cornell. At Cornell, I would continue writing for the paper, freelance stories and things.

Then my junior year, I went off to London School Economics for part of the year, and ended up writing a lot in the afternoons because school, as you might imagine, was like over in London at two, three in the afternoon, which was like nine or 10 in the morning. I would often be writing articles almost every day. Little articles, but it was just a great education for me.

Ben: I want to go to the beginning of DealBook. I am still astonished at how early this was in email. When did Substack start, 2016–2017, somewhere there?

Andrew: I think 2016–2017, yeah.

Ben: Ben Thompson started writing, 2011–2012?

David: 2012–2013. I think it was 2013, yeah.

Ben: I had no idea that DealBook predated all of this.

Andrew: That was a really remarkable period. Yeah, it’s 2001. I had lived in London after I went to Cornell. I’d been covering mergers and acquisitions, trying to break stories, and be as competitive as we could be. I get back to New York. I’m supposed to cover M&A. I am thinking, okay, this is going to be easy pickings. I thought it was hard in London because The New York Times wasn’t the local paper.

I started to meet bankers, lawyers, and people in that whole nother world. They’d say, Sorkin, you seem like a nice kid, but we get The Times at home. I read the front page, sometimes the sports section, and then I leave it with my wife. I take the Wall Street Journal with me on the train.

That was like dagger to the heart. It was like dagger to the heart. I was like, oh my God. How am I going to make this work? I thought, well you know what? I spend an inordinate amount of time racing around the Internet trying to find little bits and nuggets of things. Everybody else is doing the same thing. If I could put that in a report every day and then effectively almost bypass the physical paper and go straight to their inbox, since they seem to be claiming that they’re leaving the paper at home, maybe this is the answer.

David: There’ve been a history of newsletters on Wall Street, but they were faxes, right?

Andrew: Yeah. You could get all sorts of analyst reports back then. People would fax the analyst reports for the most part. A lot of stuff was going by fax. In fact, when we first started DealBook, if I remember correctly, there was a number of subscribers who had their assistants—back then they called them secretaries—call and say, could you fax us DealBook? That was a regular thing. Could you please fax us DealBook? I remember always being like, well, but there are links in it and if you click on the links you can read the whole story. And they didn’t really get that. That was the original conceit.

Inside The Times, I will say there was support but marginal because (I think) most people didn’t understand what we were trying to do. The other piece was part of the conceit was we were going to link you oftentimes to our competitors. We were going to provide links to The Wall Street Journal or The Financial Times, or oftentimes back then there were a lot of local papers that were doing actually incredible business coverage.

When Alcatel was buying Lucent, we would translate parts of Le Monde, we would send you to The Trenton Times, give you what they were saying about a deal or what the local issue was in Dallas, if there was something going on in the oil patch or something like that.

We were linking people all over the place and into SEC filings and other things like that. But I think as a newsroom, there was a little bit of discomfort, let’s just say, about that whole concept for a while.

David: There must also have been an ad sales and business model question, too, right?

Andrew: A couple of things. I was really trying to launch this thing in the ashes of the dot-com bust that had just happened. It wasn’t that we were still in the boom. The bust had happened, and there were real concerns, just about the economics of everything. The New York Times actually had what was going to be a tracking stock for its dot-com business. That looked like it was starting to go off the table, if you will, given what was happening in the marketplace.

In any event, their view, if I got to go back and look—I was actually trying to find some of these old notes—I think they thought that the TAM—I don’t think we ever used the phrase TAM back then—was 30,000 subscribers for free.

Ben: What is it today, if you’re willing to share?

Andrew: We’re over a million subscribers.

David: This sounds very like in my own journey. In the early days we used to be like, oh, there can’t be more than 10,000.

Ben: There are 10,000–20,000 people who will listen.

David: Who would listen to this, yeah.

Andrew: I had this thought that we get the whole thing paid for by advertising. I was not looking to charge for it. Really the whole goal was to get the brand of The New York Times out in front of this audience more than anything else. I told them that we were going to make money on day one. I said we would not do this unless we made money on day one. And we did.

Our original advertiser was Brooks Brothers, is our first advertiser. Brooks Brothers is still in business, but only by a hair, I think. I think they’ve gone in and out of business a couple of times.

David: Were you doing the ad sales?

Andrew: I was not doing the ad sales. The good news about The New York Times at that point, and continues to be the case, but there really is a church and state wall between the two.

We also had a currency exchange, if I remember, was another advertiser that was one of the early ones. But anyway, within a couple of months it felt like the thing had caught fire and all of a sudden there were people who were sending me emails saying how do I subscribe? I’d like to subscribe. We get the (as I said) the phone calls from different CEOs saying, can you fax it to my boss or whatever it is. And we were off to the races.

David: Was there a cool dynamic where people who you were covering would subscribe and then would reply to the email?

Andrew: Oh yeah. Even to this day, that’s the coolest part about it, which is just the audience is so crazy. Crazy in some of the names that get it every day, that oftentimes they would reply.

People used to send us—they still do—I get PDFs of decks about a deal that’s going to be coming within two days or ahead of time. Someone’s leaking us something or people are replying to this saying, I’m involved in this transaction. By the way, you didn’t get this right. I want to tell you what actually really happened.

David: What a great reporting channel. Just the replies to…

Andrew: The replies are a huge sense, just that immediate feedback that you get. That actually was a huge plus. It’s funny. Now that is so common and normal. But back then, 25 years ago, there was no feedback loop in that way. This really was one of the first.

We didn’t have Twitter or X. Any of these other social media platforms didn’t exist back then. This was like an original way to do that.

Ben: All right, I got to ask. What is the meta game here? What’s going on when you do get a reply that said, actually I’m involved in this deal. You’re not getting this right. Here’s the real thing. Obviously, there’s an incentive at play to share that with you. How does that enter into how you decide to absorb information when you get it?

Andrew: My view is that every source has some motivation for why they’re talking to you. Oftentimes, if not all the time, it is self-motivated. There is something that they believe benefits them.

I think it’s important to understand what their motivation is. But ultimately, as long as I can confirm the information—typically from 2, 3, 4 different sources—or I can get documentation of the issue, I try not to worry too much about what their ultimate incentives are because some of the best sources have completely terrible and ulterior motives.

I can’t tell you how many times I’ve had people who want to screw somebody else over. Even people that you thought were their friends, people in offices that literally were next to each other and somebody’s ratting out the other. I had situations where I’ve talked to board members.

I remember 11-member board. Ten people want to do a deal. One of them thinks the deal is a terrible idea. Thinks if the deal is somehow in the public domain that they’re even considering it, the public shareholders will freak out, rebel, and that will turn on the company.

I’ve had the opposite happen. I’ve had CEOs who thought that their board was against them but was convinced that if the public markets understood that they were contemplating this, they would cheer and the board would actually be put into a corner the opposite way to do a deal.

David: We just finished recording our Coca-Cola episode. I don’t know if you remember this. The CEO of Coca-Cola struck and announced a deal to buy Quaker Oats.

Andrew: I worked on it that night. I remember that night. I remember that night like it was yesterday.

David: Quaker Oats owned Gatorade, which was the reason to do it.

Andrew: The press releases were ready.

David: The two CEOs did a joint announcement, and then the Coca-Cola board killed it, after the announcement. Unbelievable. Then Pepsi ended up buying Quaker Oats and Gatorade, and it’s been a home run grand slam for them.

Ben: David, I love that you’re telling Andrew this. I’m pretty sure Andrew knows.

Andrew: No, but it’s a great story and it’s an example of just how these things happen, where from the outside it all looks very organized. Oftentimes, you see a big announcement and there’s a press release, but behind the scenes, invariably there are a lot of different egos and personalities that have their own plans, if you will.

As a reporter, that’s where most of the stories come from. Sometimes very senior people, sometimes junior people. By the way, junior people who hate their boss or people who love their boss. It’s up and down. I think people have this view that maybe you talk just to the most senior people. That’s typically not the case. Oftentimes, a great story starts at a very junior level. Oftentimes, a great story starts with, I call the jilted somebody.

There could be an auction for something. Someone’s now lost the auction. Now they’re jilted. The jilted lover. Now, if they have any incentive in life, they have no skin in the game except maybe to upset the situation.

Or maybe there’s a banker or a lawyer or an accountant or somebody else who thinks they’ve spent the last 10 years sending Christmas cards to some CEO thinking that this is their client, taking them on some annual conference or ski trip or something, and then all of a sudden finds out that Goldman Sachs got the business and not them. Well now they have no skin in the game, so they may be more inclined to say, hey Sorkin, you should look into this.

By the way, it’s very rare that someone just calls you up and tells you this stuff. But I think if you’re in the flow calling around, talking about different things, sometimes it just comes up in conversation. People are maybe willing to say, or it’s like one of those they’re having a bad day. You might be talking about something else and you might say, well, what else is going on? And they might say, well I got to tell you. I just got totally screwed on this situation. You should check out this other thing because… And that’s a lot of stories like this start.

David: You get a beat like that, you say you need to confirm it with 2, 3, 4 other sources. How do you decide who to then call next?

Andrew: Well then I start to think through, okay, who in my network that I’ve tried to develop relationships with might know about this. Before going to the tippy top, I always think if you go straight to the top, you will probably not—

Ben: I know X. Can you confirm or deny?

Andrew: Yeah, that doesn’t really work. You need to get enough information, usually at lower levels, to know where the meetings are happening, when they’re planning on announcing, what’s the price. If it’s a stock for stock deal, what’s the ratio? Is there a collar to the ratio? I always say you want to get 80%–90% of the way there before asking the company for comment, if you will.

I will say that if you get to 90% of the way there, oftentimes it behooves the company in some way to tell you what’s actually happening at that point.

David: They’d rather have a hand in shaping the narrative versus not.

Andrew: Typically. Most companies do want a hand in at least to tell you what’s going on. Look, my view is it makes a story stronger. I want to know what folks think. I want to know what folks think in a positive story. I definitely want to know what folks think in a negative story. I think it makes it a better story to include whatever the other side of the story is.

Ben: Okay, we could talk about this forever and I’m interested in part because David and I don’t think about ourselves as journalists, and yet what we do rhymes as this business historian, even though we’re not really—

David: We’re just doing it about the past. But it’s similar. Different people remember things very differently, as you know, you’re a historian too.

Andrew: It’s very interesting to try to think back. I just finished this 1929 book.

Ben: Which is fantastic, by the way. I’m in the middle of it for anyone who hasn’t read it yet or listened. It’s great, by the way. I love that you narrate it too in the audiobook.

Andrew: You guys are in the audiobook. I’d never done anything like that before. But what I was going to say is stories about today you can go obviously talk to people who are involved in them, and they can give you their perspective in the moment.

Stories 100 years ago, you’re dependent on letters, diaries, memos, notes, and all this archival material, which you guys have unearthed a whole number of times when you guys have been working on projects around companies that have lengthy histories.

I always try to put myself in the shoes of the people who are living, and I found myself trying to put myself in the shoes of the people who were not living back then. What would they be thinking? Why would they be thinking it? How would that relate to somebody who’s alive today? I don’t know if you guys ever think about that, but…

David: We definitely try to, modernize is the wrong word, but make these characters real. Talk about them reenact conversations in the way that people would naturally have them today, as opposed to you read a history book and it sounds very stilted. I’m trying to think of an example. Maybe like Standard Oil. It really is incredible drama, ruthless stuff that’s happening.

There’s a way to talk about that in the language they were using at the time that might be a little less accessible today. There’s a way to talk about it of, you’re not going to believe what Henry Flagler did next. What an animal, that guy.

Ben: Well, Andrew, I was going to ask you, how many years was it of the newsletter before starting the DealBook Summit?

Andrew: We started the summit in 2011, in fact. We’d basically been doing it 10 years, 10 years in. Really the summit was just the idea of could we bring the pages of DealBook to life? Could we actually take all these characters who we were writing about every day, who oftentimes were replying to us on the email, put them on a stage and talk to them in a really human way so that people and the public could see them and see the way they think about the big issues of the day?

I always love conversations about ultimately why people think what they think. I care about the information they’re imparting, but I feel like especially when you think about people of great influence and power and all of that, even if you disagree with them, understanding why they think what they think, I think has huge value just to our collective understanding.

Ben: I’ve thought that watching the last few years of DealBook Summit interviews, whether it’s Elon or Sundar or Jeff Bezos, it’s not like they’re sitting there breaking news. It’s not an act of reporting to do the summit, but you really do get inside the psyche. You get a much richer texture of why they’re doing what they’re doing from an hour-long interview.

Andrew: A lot of them go between a half hour and an hour. In terms of the reporting, you’re right. It’s not oftentimes news of the moment, though sometimes they do make news in that moment that make headlines,

Ben: Alex Cooper dropped her energy drink.

Andrew: She did. But to me, ultimately it’s reporting that ends up explaining what they did in the past and oftentimes gets used later in what they do in the future. Sometimes you’ll see little nuggets, little quotes, little other things that end up in the newspaper six months later after they’ve announced something else that they’re doing, or something happens and those quotes are used as a way to explain them.

Ben: It’s funny. I haven’t had a chance to read today’s DealBook yet, but I’m very curious in the story that you helped report around Jeff Bezos’s new venture that I saw, just a headline of this morning. Does that call back at all to your interview with him, where he’s talking about all the heavy industry that they want to move off or then what’s going to be necessary to accomplish all of that?

Andrew: Yes, because he made a particular point of leaning in to AI. I remember being a little surprised about his interest in artificial intelligence and how he clearly wanted to talk more and more about artificial intelligence. I remember thinking to myself, well Amazon doesn’t have its own large language model right now. Arguably it’s behind. I think a lot of people thought that at the time. Here’s a guy who’s says he’s focused on space, so why is he all of a sudden talking about AI and talking about how he thinks AI is like fire? I remember him saying, he thinks it’s that important.

Last night when I learned about this, I thought, oh, okay. This all makes a little bit more sense now. He is going to become the co-CEO of the company, which to me is remarkable. He was not the CEO of Blue Origin. He was the founder, but he had hired someone to be the CEO. The last time he’d been the CEO of a company obviously was Amazon. The idea that this is what he’s effectively doubling down on and where he’s going to focus his own personal energy (I think) is pretty interesting.

David: When you were starting the summit back in 2011, did you think about it as, we have this amazing readership and engagement of people replying. Let’s bring it to life. Let’s make something really amazing around this. Or did you think about it as like, hey, there are a bunch of these business summits out there to varying degrees of great, and maybe there’s an opportunity for us to become the premier version of this?

Andrew: I think it was a combination of both of those things. The truth was back then there weren’t nearly as many conferences either. The biggest at the time was probably what was the Wall Street Journal D Conference, which ultimately turned into ReCode, and that was focused really on tech more than anything. I think we thought the opportunity was the confluence of finance and Wall Street tech and policy out of Washington.

Our first DealBook, Jamie Dimon (I think) was the opening speaker. Lloyd Blankfein, Marc Andreessen, Eric Schmidt, Dick Costolo who’s running Twitter at the time, those were some of the big leaders back then who we had.

Then I think the second year, Ken Griffin, Dan Loeb, Preet Bharara who was at that point running the Southern District of New York. That was really the backstory of what we were trying to do. We thought there was an opportunity to elevate all of this, but I don’t think we knew where it could all go.

Ben: To me, this is the flagship set of interviews for the year. Each interview that you do is on par with the one big interview that David and I would do for the year. We will maybe do two. You do eight of them back to back in one day. How do you prep for that? What does this process look like?

Andrew: I would say each interview usually takes me anywhere between 15 and maybe 30 hours of prep, typically. First of all, I keep a little notes app in my phone for all sorts of people. Some of the people who make it to the stage, some people who are sort of my wishlist that for whatever reason don’t happen. But I keep little notes throughout the year of little quotes, of little articles, little notes and things about them so that I can go back to that later on.

I ended up spending a lot of time talking to other people who know different individuals about them. Sometimes it’s as much about knowing certain facts as it is about their disposition, what’s really driving them or motivating them, just trying to understand them. Some of these people I’ve known myself for many years, some of them I’ve never met in my life before.

I do try to talk to them if I have never met them before, prior, like on a Zoom or something, or maybe try to meet them. Oftentimes, they do have PR teams and other people who reach out. I do like to understand them if I can, so that it’s not totally cold for the first time.

I never share questions with anybody as a policy and as a rule as a journalist. We do often talk about themes thematically, probably want to touch a couple of things, just because you also want to get them thinking a little bit in that moment ahead of time so that they’re not coming to all of this completely cold. I don’t know if you ever interviewed somebody where they had no clue why you’re planning to talk to them.

David: The closest was Barry Diller at Radio City, but he’s so great. We kept trying to reach out like, hey, do you want to chat? You want to prep? We can send you stuff. He’s like, no, no, no.

Ben: We did ultimately do a quick call from our dressing room when we were in rehearsal.

Andrew: Even that, by the way, I often think that the most important time of an interview, oddly enough, and it’s actually hard in the context of DealBook because I’m on stage most of the time, and I’m only coming off for a minute or two in between sets sometimes, is in those two minutes prior.

On TV when we’re doing Squawk, I often think that the most important time is while the commercial break is happening and someone’s sitting in the chair. People come in. They’re a little anxious, a little nervous. Trying to get them to settle and trying to get them to be the best they can be (I think) is almost more important than what ultimately I end up asking them on the stage. However you can meet them where they are before it begins (I think) is a huge thing that I try to do.

David: That’s so true. Chase Center. Ben made our conversation with Mark Zuckerberg at Chase Center. It was all in the wings beforehand. Andrew, I’m sure you have this every time in the wings.

Andrew: No. It’s like, how do you meet that other person where they are. Everybody comes to it totally differently. There are some people who come either with great energy, there are other people who come completely scared out of their mind. You can learn a lot by shaking a hand, by the way, you get a sweaty hand, you know what’s about to happen.

Ben: David and I are business historians. We’ve watched so much tape of Squawk Box. Walking onto the set almost felt like this weird Disneyland experience. Like, whoa. This is what it looks like in real life. So there’s a little bit of this heightened energy for me walking in. You guys did a great job of making us feel very at ease.

We had another TV appearance where we walked in and the host just stared down at his iPad the whole time and literally ignored us one foot away. It was a complete night and day experience.

Andrew: Well, thank you for that. We always say we think we should start a streaming show during the commercial breaks because what happens during the commercial breaks is oftentimes as fun, if not crazier than what happens. And we’re all on. It’s very rare where we’re just looking down an iPad.

Sometimes, I will empathize or sympathize with whatever that person was that your experience was with. There have been times where some news is breaking or something’s happening, and you feel like you have this 90 seconds between commercials and then you have to study the thing so you know what’s going on. I don’t know if that was your circumstance.

Ben: This was not that, but I could see that being a very valid reason.

Andrew: I’ve had that and I’ve felt bad about it. There’ve been a couple of times where I’ve stared straight at the screen, not really looked up and I probably should have. Maybe the person next to me was like, what is going on here? And I’ve been in my own thoughts.

David: You guys in Squawk Box put a lot of thought and effort into the guest experience. You had a car pick us up. We were greeted in the waiting room. It’s very nice there. We’re offered something to drink. We’re escorted in, we all say hi.

Ben: Oh, you don’t have to do your own makeup.

David: Yeah, you don’t have to do your own makeup. This is night and day versus the rest of the industry.

Andrew: We want it to be fun. I think actually one of the reasons people keep coming back and want to come on the show is for the most part, I think people have a ball doing it. Even by the way, when we have disagreements or debates or whatever it is, the experience is a fun experience.

David: Well I can tell you, as guests it felt like you really valued our time and experience. It didn’t feel like we were the commodity filler for that 10 minute segment.

Andrew: But that’s the thing. There is no commodity filler. Honestly, whether you’re Barry Diller or Jamie Diamond or an analyst who’s studying a stock, I think we all think that each of these component parts over the course of the three hours has huge value to the broadcast.

Ben: Going back to prep, give us the lineup for DealBook this year. It’s about to happen. We’re recording this. I think we’re going to release it right after the video comes out.

Andrew: We’ve got everybody. From Secretary Bessent, which I imagine is going to be a conversation about (obviously) our economy, what’s going on in Washington, tariffs. We’ve got an interview coming up with David Ellison, who of course is in the middle of having just bought Paramount, trying to buy Time Warner Discovery, and whatever you think the rest of the chess board looks like. Obviously, his father at Oracle is involved with all sorts of AI efforts. They’re getting involved with TikTok.

I’m going to be talking to Erica Kirk, the widow of Charlie Kirk, which I’m really looking forward to. I actually knew Charlie. I remember watching her at the funeral. I think her words and the way she talked about wanting to forgive the killer of her husband, I thought was unbelievable. She’s now going to be running Turning Point, which is hugely influential in the conservative Republican movement. I think trying to understand the way she’s thinking about that could be really, really interesting.

Mary Barra, probably the most influential, powerful female CEO in America, runs General Motors. She’s in the middle of it all, talk about manufacturing in America and the whole tariff story.

Dario Amodei who runs Anthropic, I think he’s one of the most personally interesting people in artificial intelligence. He’s been willing to speak out and say things that I think a lot of others have not. He has some very provocative views about the implications of AI, even what some of the things like Nvidia and others and the political class is doing. President Trump has made some comments about him. I’m very curious.

David: He’s also had a large hand in every single one of the major foundational AI players—Google, OpenAI, Anthropic, all have his fingerprints on them.

Andrew: All have his fingerprints. I think spending some time with him is going to be really interesting.

Alex Karp, who’s the co-founder with Peter Thiel of Palantir, runs Palantir. I think that’s been considered one of the hottest stocks clearly, but also one of the most interesting stories in companies in the country. We’re going to do a conversation with what I call the Young OG and the old OG of finance. We’re going to put Brian Armstrong and Larry Fink together.

Ben: Are you doing every one of the interviews you mentioned so far?

Andrew: I do all of the interviews. Every interview on the stage, I do. We started doing that maybe in the third year of the conference.

Then we’ve got arguably the most influential, powerful influencer in the world. Jimmy Donaldson, better known as Mr. Beast. My children want to come to DealBook this year for that very reason.

Then we’re going to have a conversation with Gavin Newsom, of course, the governor of California, who’s probably been the most outspoken and vociferous politician when it comes to being on the other side of the Trump administration.

Ben: Okay, you’re doing all this in one day.

David: It sounds insane.

Andrew: Oh, and Halle Berry. Halle Berry, Halle Berry, Halle Berry.

Ben: How could you forget Halle Berry?

Andrew: Can’t forget Halle Berry. Yeah, so I’m going to do this. I’m usually on stage from (call it) nine in the morning to six or 6:30 PM, and it’s an all-day marathon. It’s like sprinting a marathon.

David: I assume you’re going to take the day off from Squawk Box.

Andrew: I take the morning off. I usually go on for five minutes in the morning and tease what’s going on all day.

David: You go on Squawk Box before all this. This is insane.

Ben: I’m just thinking about the amount of prep. Truly, the CPU of my brain is redlining going into a Zuckerberg interview or a Ballmer interview or a Jensen interview, where my job—and David’s job; David’s job is more of the story—is to more the reflection and the analysis is to make sure that we leave that interview with, did we give the listener important takeaways? Do they have something where they’re like, whoa, I learned something new I didn’t know before. I understand this at a deeper level.

It takes everything I have to do that. I really do feel the DealBook interviews are of that caliber, where you get to indulge in this person’s psyche for that period of time. What are your tips and tricks?

Andrew: For me, I have to absorb all of the information in advance. I need to almost know it at a visceral level, so that it’s not about notes or anything else. It’s just like you know it. There often isn’t a lot of time, even between interviews to recalibrate and rethink, okay, I’ve got to start this new one. It really is for me about feeling it, if you will, and having read so much and having spent so much time thinking about the different ways it could go.

I do think a little bit. The analogy I often use is I try to plot out in my mind and on paper, actually, what the flight path is, knowing that the weather’s going to change. But I know that I’m starting at JFK and I know I’m ending out at LAX. I know I’m probably going to land at O’Hare, maybe Atlanta, Denver, and Dallas.

Ben: And we may not pay ATC along the way, so who knows what detours are going to happen.

Andrew: But I also know the weather’s going to change. So my ambition to get to O’Hare first might get upended pretty quickly and we might have to divert to Atlanta first. Then how am I going to pivot back if I want to go back there?

For me, it’s like having a little bit of a path, but then listening. You guys do this so brilliantly. I think the whole trick is to listen because there’s going to be so much new information that’s going to come up that’s going to surprise you. But then if you’ve prepped, that new information is going to inspire you to then maybe drop some other piece that you had read about or thought about before in that moment.

Ben: And if you can get the subject to smile and be like, wait, you knew that? Or you were able to connect that dot? Then the whole rest of the interview is going to be much more interesting because suddenly they’re a fan.

Andrew: I remember interviewing Bill Gates many, many years ago, and I’ll tell you what the tell was. It wasn’t a smile. It was he slouched in the chair. At one point in the conversation, it was as if he had turned the chair into a hammock and he was just lying there. I thought, okay, we’re here now we can do this.

Ben: I just feel like I’m never as smart or as maniacal or as empire building or as any of these people, but I can be better researched about their journey than just about anyone out there. If you can get that game recognized game moment where they’re like, oh, you really did a lot of work on this, I just feel that that’s where a lot of the beauty comes from after that.

Andrew: Well, I think that a lot of people have an enormous amount of mutual respect for you guys because they see it. They see the work, and the work is so evident when they listen to you. Embedded both in questions when you’re doing interviews or obviously embedded in the storytelling that you do, is all of this information which can only be acquired by demonstrable research that frankly can’t be done by AI.

David: That’s a great point. You’re bringing your whole body of work to the interview, and your subjects have that experience too.

Andrew: Hopefully, yeah. That’s what you want.

Ben: All right. Let’s talk logistics and then I want to talk about the business. At CNBC, you have a producer team. We got to interface with some great people who helped us prepped, who prepped you. There are teleprompters, there are notes. What does the producer side of DealBook Summit look like?

Andrew: We do have a fantastic events team that’s doing a lot of the organizational work just because there are obviously hundreds of people in the audience. There are all of the participants who are on the main stage. We also have a series of these things called task forces and groundbreakers. There are a lot of moving pieces for the interviews that I do.

Most of the notes I’m creating myself, I do have a producer who helps me with some things, some early research as I’m gathering to put things together. But that’s really the extent of the setup. It’s not like there’s some huge apparatus that’s building notes or questions.

I often, by the way, do lean on, there are some great, great beat reporters at The Times who obviously live and breathe particular topics, CEOs, and businesses. I’ll reach out to them and say what are the five questions you think absolutely need to be asked? Or are there particular places that you think I can go or different ways to get there? Sometimes it’s about knowing where the speed bump is for the other person, and then figuring out a way how to get to the same place without them feeling that bump.

Ben: I know exactly what you’re talking about. There’s an area of sensitivity for a person that is adjacent to a topic that’s really interesting. How do you get to that really interesting topic without making the whole thing awkward and depriving the audience of a good interview.

Andrew: And I want the other person to hit the ball back. I always say—here talking about airplanes—it’s also a little bit like a tennis rally. You want the ball to go back and forth. Even if I hit the ball into the corner of the court, and yeah, we’re seeing the person run to go get the ball, I’m still rooting for them to hit the ball back. I do want them to hit the ball back.

It’s a question of how do you place the ball there so that they can hit it back in many ways? And that you’re going to get a really revealing, interesting answer as a result. Sometimes it’s complicated because I do feel, again, and I’m curious how you guys think about it in the context of I’m a journalist, you guys say you’re not journalists, and sometimes there are questions or issues that are really difficult that I want to and feel like I want the interviewee to grapple with. How do you get them to grapple with it in a way where they don’t necessarily either feel defensive or they don’t feel they’re being attacked or what have you, but that you’re actually learning about the way they think about that particular issue.

I find, by the way, one technique that does work. Sometimes I’ll find a quote that somebody else has written or said that’s critical either about the company or the person or some issue or raises an issue. I’ll read the quote aloud. By doing that, two things are happening.

One is, it’s not me saying this. It’s not here I am accusing you of something. It’s, there’s this thing, it’s in the public domain. The public is thinking about this. Also, everybody’s thinking about this. How do you think about it?

The other reason why I find it’s actually very effective is typically the other person has thought about it a lot, even if it’s somewhat triggering or painful. They’ve read the quote, they’ve grappled with that quote oftentimes for weeks on hand because they’re either annoyed by it or they think there’s another… So it’s not an impossible question to answer.

Ben: David’s over there chuckling because I have tried to steal a very specific phrase from you, which is you depersonalize it. You bring something up and it’s not Andrew saying it. It’s, there’s this quote. When you hear that, you would say what?

David: You would say what? Yeah, yeah, yeah.

Ben: I just love it.

David: You literally call it the Angie Roth star kid phrasing.

Andrew: My wife is going to laugh when she listens to this part of the podcast.

Ben: Why? Tell us.

Andrew: Because I use that with a lot of things.

David: I could imagine if you are your spouse, that would be extremely annoying.

Andrew: What would you say? How do you think about that? I have a whole bunch of friends who always mock little phrases.

David: How do you guys think about the set and setting for these. You have a whole set of choices that you could make about number of attendees, who those attendees are, the stage design. You’re like, it’s very sparse, but you could be more intricate. I’m sure these are all intentional choices.

Andrew: I think the audience is as important as who’s on the stage. I often say that people in the audience could clearly be on the stage. One of the reasons that I think people who are on the stage want to be on the stage and oftentimes want to win over the people in the audience, is because they’re peers in many ways.

I think we try to have a good mix between business leaders, the political class, the academic universe, the journalist, public intellectual culture group. That there’s a really interesting mix in the room. I think every year we’ve tried to elevate that.

I love the Appel room at Jazz at Lincoln Center. I think it’s just one of the most beautiful rooms in New York City. It overlooks Columbus Circle, it has natural light. There’s something super intimate about it. You can put close to 400 or 500 people in that room and it doesn’t feel like that. I think there’s something very special about that. Then the truth is we just use a massive LED screen behind us because you can almost paint whatever you want on it at any moment. And that’s the set.

Ben: And yet it mostly has this one particular graphics package that is heavily identifiable, has been this way for a decade or more, and I feel like I can spot a photo from the DealBook Summit a mile away.

Andrew: That’s just branding because in those pictures get used repeatedly throughout the year. I think now people look at that background and they just know, oh, that happened at DealBook.

David: I was actually at a gala dinner in that room a couple of months ago, and it was the most bizarre thing. It’s a totally different setup. There are all these round gala tables there. This feels very familiar but an entirely different context.

Ben: For a certain business political technology segment of the world, it’s almost like that room is typecast, that that room can’t have another role in the world.

Andrew: For our crowd, yes.

Ben: Okay, so this is Acquired. What we do is we analyze businesses. What is the business of DealBook and the DealBook Summit? How does it play a role?

Andrew: The business of DealBook is the newsletter franchise, which we publish six days a week to effectively over a million of what I think of as some of the most influential people in the world. Both business leaders, policy people, cultural leaders. It’s just a spectacular audience. It’s driven by advertising. It’s not a separate paid subscription.

Ben: Is it a DealBook-specific advertising team or part of The Times all up advertising?

Andrew: It’s part of The Times, but there are people who are more focused on selling advertising and sponsorship related to DealBook. But clearly across the board there are people in the advertising department that work on that.

Then the event itself is really, as I said, a manifestation of the newsletter. That unto itself also has a huge sponsorship component. A lot of the sponsors who are involved in that are involved in the newsletter and other parts of The Times and things like that. That is the business.

Ben: So 100% sponsor-supported, no direct monetization of the entire thing.

Andrew: There’s no subscription model for the newsletter. For me, the truth is we’ve always wanted, if we could, punch above our weight in terms of reaching the most influential people in the world. That was really our goal more than anything else. It was about reach. We found that we can make the economics of the business work pretty well under this scenario.

David: And does that apply to Summit too? Can you buy a ticket to Summit? Or you don’t buy tickets, it’s only sponsorships?

Andrew: Our readers can apply effectively to buy a ticket for the event. We do maintain a group of tickets that are available for readers and the public who want to participate.

David: But you’re still curating the room.

Andrew: But we’re still curating the room. We’re also super intent on making the event as public and available as possible to the public. So within 24 hours of the event, all of the interviews are available for free, not just on NY Times, but on YouTube and other platforms.

Ben: I was thinking about what David and I have done, and people will often describe us as founders or entrepreneurs or talk about taking the leap, leaving venture capital to take the leap to do this. I really don’t feel we ever took a leap. I feel we are the least risk-tolerant founders I’ve ever met. This all happens slowly, accidentally, and with almost no risk. other than our time.

I’m curious for you, Andrew. What to you has been a leap? When have you really put yourself out there? When have you bet on yourself versus it was actually a pretty conservative choice and it just happened to work out well?

Andrew: I think for me, probably the biggest leaps were writing too big to fail. I think that was a leap for me. I remember when I first got the advance for the book, I thought, I remember telling my wife, we’re going to have to give money back. I wasn’t sure I could write a book. I didn’t know if it would work. I just thought there’s just no way that I’m going to be able to do this. I think writing that book was a leap.

I think actually writing 1929 was a leap. You might not think it was a leap, but for me it was a huge leap because I had never actually really written about history and people that weren’t alive. I was super scared the whole time. Really, the first couple of years I wasn’t even sure I was going to really write the book. I didn’t know what I was doing. I think my kids thought I was wasting an extraordinary amount of time.

I think one of the leaps, when I co-created Billions, I wrote that with Brian Kaufman and Dave Levine, and we did that all on spec. That original pilot script was total leap. Like we had no idea whether we were going to get anyone to buy that thing.

Ben: On spec means you do all the work to write it.

David: You didn’t have a studio giving you a development fee.

Andrew: No, didn’t have a development deal or something in advance. It was literally you were writing and hoping that somebody would buy the work, would buy the project once you had it all on paper. I think those things were probably a leap.

By the way, to me maybe even going on TV was a leap. I didn’t know whether that would work or not. That could have failed pretty miserably. It still could.

David: Seems unlikely at this point, but…

Ben: Well actually, I thought this was the direction you were going to go because I was going to ask. It seems like a risk to become a celebrity. Before you were a journalist, your face wasn’t everywhere. Now you’re Andrew Ross Sorkin. Did TV do that?

Andrew: It’s a little complicated for me to answer this only because I was going on TV to talk about my articles for a very long time. Back in 2002, 2003, and 2004, I was going on the Today Show back when Katie Kirk and Matt Lauer were the hosts and back with Charlie Rose. I remember during the Martha Stewart trial sitting at the desk there with Katie. For a long time I felt like there were times I would get on the subway and someone would say, oh, I just saw you on such and such or this thing or that thing.

It’s probably elevated today to some degree. I think there are more people who saw me on the subway now. I don’t think I ever really thought about that part. I don’t think I’ve ever really thought about that part.

It’s maybe to my own detriment. If we were to go out to dinner, I don’t really realize that there are people who know who you are. I find it weird, so I don’t even really think about it or acknowledge it until I have to, I guess.

I used to have people come up to me on the street. I’d be with my kids and my kids would always say, dad is that a friend of yours? How do you know that person? I’d be like, I don’t know. I think maybe they watch the show in the morning. I’m not sure.

David: Well, hopefully you have the same version of this that we have, which is our audience are super smart, super curious, super wonderful people who we’re always happy to talk to.

Andrew: Totally. I find it so exciting when people come up to you and they want to give you a high five, or they say this to you on the show or this or that.

Ben: While we’re on the topic of TV, I do want to ask you about Billions. I loved Billions, especially the first few seasons I think are some of the best television that has ever been created, that succession. I’m a sucker for that genre, but God, Bobby Axelrod is such an amazing character.

How did you work that into your life? What was your level of involvement in Billions? How did you work it into everything else you were doing? And did you think in any way that it was a risk?

David: You might start getting some replies from your sources being like, you rip me off for this pseudo character.

Ben: Or that affects your brand as someone who covers the truth, not who makes up these fantastical worlds.

Andrew: I had been a co-producer of Too Big to Fail. We’d made a movie of Too Big to Fail for HBO. Paul Giamatti, who ends up in Billions obviously is Chuck Rhodes, was Ben Bernanke in Too Big To Fail. I loved that whole process of being on set and working on that film. I thought I learned more. I thought the people at HBO were amazing. Everything about that was such an extraordinary experience.

I was thinking to myself, is there some other project I could do that’s in the television world? At the time, I had not really seen a show that put the world of hedge funds on its feet, and I thought that could be a really exciting genre in the world.

The truth is actually when I first went to LA to visit with my agent, he told me this was a terrible idea because people hate people on Wall Street. They just look at computer screens all day. It’s going to be boring. Blah-blah-blah. Back then, I was just really thinking more about maybe a character that’s like Bobby Axelrod, around a hedge fund and their family.

Then I remember coming home and my wife was watching a rerun of Law & Order on USA Network. I said to her, you know what shows work? Legal shows work. People love a great procedural. Why is that? They just eat these shows up. Then I thought, okay, what happens if you could set these two worlds against each other and maybe you’d fall in love with the hedge fund guy?

By the way, I covered a lot of white collar crime too, where sometimes the prosecutors who you thought were doing things in the name of right weren’t always doing things right. I thought that was a unique way to approach the issue.

I don’t think I was so worried about the fictional nature of it. My role was really in helping put the whole thing on its feet. Then of course I met Brian and David. They were the showrunners of the program. They really took the whole thing and ran, and were really great. If you love the show over all those seasons, give them the credit.

Ben: Was it strange casting yourself?

Andrew: Strange casting myself?

Ben: There is a character that seems to rhyme with what you do.

Andrew: No, I didn’t think he really was me. I never thought about that way.

Ben: No?

Andrew: No, I never really did. I know who you’re talking about. For whatever reason, I never thought he was pertaining to be me.

David: Okay, so we got DealBook, CNBC, the summit, the books, Billions. How do you think about the business that you are running? What is the business of Andrew Ross Sorkin?

Ben: There is a media empire here.

Andrew: I don’t know if it’s an empire. I think of it more as I’m a journalist. I’m writing, reporting on, and talking about what’s happening in real time in this fascinating universe of business meets policy, both in terms of what I do on television, what I do with The New York Times. And then are there things I can do that layer on top of those things?

They’re all interrelated, really, whether it be a fictional TV show or a book project or something else. It’s just another way of telling the story, reaching more people, and reaching them in different ways. I love when someone comes up to me on the street and tells me about a story that they read that I wrote in The New York Times like a decade ago that somehow meant something to them.

But I also love the idea that somebody could watch Too Big to Fail on HBO, on the streaming service now, you go back and watch it and they’re like, I’ve watched it 10 times. I remember this and this and this and this. Or someone who reads 1929 and learns about these different characters and people.

I’m just trying to take this lens that I have on the world, which is typically the lens of people and characters, and trying to understand what incentivizes people and motivates people to do things, and trying to apply that to all sorts of things.

An economist might look at the world of 1929 or 2008 or a lot of things that are going on our world and talk about in the context of economic cycles and systems and all sorts of things like that. I don’t really think about it like that. I think that people make decisions, some good decisions, some bad decisions that lead to economic cycles and systems and all sorts of other things. If you can understand the people, why they do what they do, and you can really feel them, it’ll change your outlook on everything and make it a lot more understandable.

David: We get to meet amazing folks like you in the media world, and the people who are the very best, the most respected produce the great work across different mediums, basically have the same answer as you of, no. I’m not thinking about this strategically of, oh, my agent said I should add a podcast, so that’ll amplify it. It’s like, no, no, no, no. There’s a thing that I’m trying to do. I’m trying to get to some aspect of the human experience, and I can paint in some different campuses doing that, but I’m always doing the same thing.

Ben: What are some recommended best practices that you disagree with? What are some things that is canonical wisdom like David threw out?

David: Oh, you should have a podcast. Amplify what you’re doing.

Andrew: You guys probably think I do a lot of things.

Ben: I think you did a tremendous amount of things and I’m trying to figure out what the trade-offs are. There seems to be no trade-off anywhere.

Andrew: Well, no. What I was going to say is I, I feel like I do a lot of things and then I say no to a lot, a lot, a lot of things. I can’t do anything well unless I spend an extraordinary amount of time on each of the things.

People have said, oh, should you do a podcast or something like that. I’m like, how would I do a podcast? That takes an extraordinary amount of time. Could you do more DealBook Summits around the world or something? I’m like, well, how are you…?

What I’m trying to do is it took me eight years to write that book, 1929. I feel like in my own way, each thing takes a remarkable amount of focus for me to do it well. People say all the time, you should not take things personally. You hear that a lot, don’t take it personally. I think you have to take everything personally. I think that the people that I know who are the most successful people in the world take everything personally, and it’s because they care. They care so deeply.

I know that for me, I take it all personally. And it hurts sometimes to take it that personally. But I think that it’s the only way. If you’re not taking it personally, I don’t know what you’re doing.

David: I’ve already tried to think of like, what a common criticism of Andrew Ross Sorkin could be. What do you hear?

Andrew: Within the journalistic world, there are people who think that you shouldn’t know your sources. Or not know your sources but some people would say you know your sources too well. You’re too close to your sources. I’d say within the world of journalism, one critique is you’re too close to your sources.

My view is that the only way to tell the truly human nuanced story of the way they think is to know them. You have to know them somehow. I think you can do that and still be objective. And it’s complicated for me.

There are lots of times where I have to write stories that are negative or critical or where I even myself just fundamentally disagree with the other person on a particular issue. I like to think that the people that I report on respect that and actually respect it more, one man’s view, but—

David: I’ve had conversations with people who you’ve reported on where they have said that to me of like, yeah, man. I hate that. I understand it. If they were talking about a piece on them by somebody else, they’d be like, ah, that SOB or whatever. But with you, they respect you.

Ben: They don’t understand.

Andrew: I think a great journalist in a way is a fairweather fan. What that means though is if they do something right, you should say attaboy. And if they do something wrong, you should explain why it’s wrong. Now if you’re just doing one or the other, that’s where I think journalists get into trouble.

Ben: That’s a great framework. On the take everything personally, when you said what are you doing, it gets at what is the purpose of all this? Is it to do great work? Like on your tombstone, do you want to die and it says he did great work? Is that he lived a great life? Like he had a lot of fun, he spent time with his family, he did the things he enjoyed. Or he made the world better?

Whether the don’t take it personally advice really depends on which of those things you think this is all for. If the goal is do great work, you have to take everything personally.

Andrew: Yeah. I hope I’m trying to do a little bit of each of those things, but I think one of them clearly is doing great work. Hopefully, one of them is having a lot of fun doing that great work. And if I can leave the world a little bit better off at the end of the day, even better. I think it’d be very hard to accomplish any of those things if you didn’t take it personally.

Ben: Well Andrew, I just want to thank you so much for having this conversation with us. We said we would love to have you on right when 1929 came out, and I realized I had no unique angle to talk about 1929 because I was woefully behind on reading the pre advanced copy.

Hopefully, listeners you learned something from this because this was our attempt to say, Andrew’s so interesting. We loved having you at Radio City. We love getting to spend time with you this summer. What could we do together that would feel timely, cool, unique, and this is what we came up with.

Andrew: Well, this has been a ball for me, and you guys know, I’ve been listening to you for a very, very long time. I think it’s remarkable what you’ve created, and it’s just such a privilege to now know you and to call you friends. So thank you.

Ben: Thanks, Andrew.

David: Likewise. Thank you.