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- [00:00]
Ben Gilbert
Hello, acquired listeners. We are coming to you today with a very fun ACQ2 interview with our buddy Andrew Ross Sorkin.
- [00:10]
David Rosenthal
Yep.
- [00:10]
Ben Gilbert
We got to know Andrew over the summer for our Radio City show where he had a delightful cameo with us. And he's got a new book, 1929, and 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? Like, we're dying just making one show. You know, you do like four things every day.
- [00:39]
David Rosenthal
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 6am to 9am Eastern on CNBC doing Squawkbox. He's written Too Big to fail and 1929.
- [00:59]
Ben Gilbert
Two major books. Yeah, this was a very fun conversation.
- [01:03]
David Rosenthal
So today's conversation is a little bit how does he do it all? But also we realize 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? I mean, this is over a decade before Stratecheri. Don't know, 15 years before the era of substack. Doing it inside, now the biggest newspaper in the U.S. i think, in the world. And now every December, doing Dealbook Summit, which to me is kind of the flagship canonical business interview forum in the world. I mean, that's more than that. Business, technology, politics. So, listeners, this conversation was especially interested to David and I, for navel gazing reasons. But we think Andrew's story is just fascinating. It's, 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. So please enjoy our conversation on the insane productivity of Andrew Ross Sorkin. Andrew, you're wearing something different than you were wearing on Squawkbox this morning. How does that work?
- [02:13]
Ben Gilbert
Yeah, what's your wardrobe change throughout the day look like?
- [02:16]
Andrew Ross Sorkin
So I did that for you, to be honest with you.
- [02:19]
David Rosenthal
Really?
- [02:20]
Andrew Ross Sorkin
Yes. Usually I'm in a suit basically all day. I kind of sleep in a suit with a tie. And then I thought to myself, we're doing this podcast, there might be video. These guys are probably gonna wear like sweaters or look cool and I'm gonna look like some Old man in a suit. I'll put a sweater on. So that's what's going on here.
- [02:43]
David Rosenthal
Okay, so, 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 by Box. How do you think about that? Especially since that's over by what, 9:00am.
- [02:55]
Andrew Ross Sorkin
It is over by 9:00am but it's a full three hours, which often times 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 Squawkbox and then going back to DealBook and going to other projects, and they all sort of inform each other in interesting ways. About 15 years ago, I want to say, in 2011, I used to be a guest on Squawkbox often. And they called me up and they said, hey, would you want to be the host of the show? And I thought, that's crazy. I can't read a teleprompter. I've never done this before. This is insane.
- [03:44]
Ben Gilbert
Was one of the other hosts retiring or like, how did this.
- [03:47]
Andrew Ross Sorkin
A couple things that happened, actually. I don't know if you remember a legendary journalist named Mark Haynes, who was the original host of Squawk Box and then was on a show called Squawk on the street passed away, and they were going to reshape Squawk on the street, and Carl Quintanillo, who was one of the three hosts of Squawk Box, was gonna move to that show. And so they were looking for somebody to put in his chair. And I thought, you know, I love my job at the Times. I'd 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. So I always did have to get up early, but I was often in my pajamas. I wasn't interviewing people.
- [04:51]
David Rosenthal
And if you need that time to publish Dealbook now, you don't have that time.
- [04:55]
Andrew Ross Sorkin
Yes and no. So a couple of things. The Dealbook team has grown, so that actually was a huge benefit. And also I end up spending usually about an hour in the morning before Squawkbox starts, sort of making last tweaks and things to the DealBook newsletter. And that's actually one of the great ways that I sort of read in, as they say in the TV business to learn about everything that's going on, sort of as I'm doing my last licks at the newsletter to make sure everything's in order.
- [05:29]
Ben Gilbert
What time are you getting up? What time is your day starting?
- [05:31]
David Rosenthal
Right, this is 5 to 6am now that you're doing the last minute tweaks, 5 to 6am Eastern.
- [05:37]
Andrew Ross Sorkin
So 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 like looking at email texts that came in overnight, slacks oftentimes around DealBook and things like that. And 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.
- [06:14]
David Rosenthal
Yeah, it's very clear whenever I open it up, 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.
- [06:25]
Andrew Ross Sorkin
That's the goal. So if that's working for you, knock on the wood. That's great.
- [06:31]
David Rosenthal
So are you sending that from the news desk at cnbc?
- [06:36]
Andrew Ross Sorkin
No. So the button is being pressed actually in Europe by two of my colleagues, Michael Dillemar said, who's actually been with me in DealBook for about 20 years now, and Bernard Warner, who work overnight, he lives in Italy actually. And 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, before things go out.
- [06:59]
Ben Gilbert
They'Re later in the day, they've had their coffee. When they're hitting the.
- [07:02]
Andrew Ross Sorkin
They've had their coffee, they've. They've been fixing, adding, sometimes completely rewriting and changing the mess that we've made, you know, out of New York overnight.
- [07:12]
David Rosenthal
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?
- [07:26]
Andrew Ross Sorkin
Combination of both. So I think for the purpose of the newsletter, we're thinking about how can we make the reader armed and dangerous before their 9 o' clock meeting or their breakfast in the morning or wherever they're headed off to. Deal book actually transformed itself over the last. We're coming up on 25 years of doing this. You know, in the beginning, it was really for the world of dealmakers. It was M and A bankers and lawyers and accountants and people in that ecosystem. And then increasingly CEOs started to read it, and board members and strategic dev groups and then regulators and politicians started to read it. And so I think we sort of shifted our focus, especially after the financial crisis of 2008, to really sort of try to capture the intersection of business and policy and really connect the dots between lots of different storylines. And 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.
- [08:34]
David Rosenthal
We're sort of starting in media stress 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 or to the Times.
- [08:49]
Ben Gilbert
I mean, you made the quip earlier in our conversation about you started it, you know, when you're 18 at the time. You literally started at age 18, right at the New York Times. That's not a joke.
- [09:00]
David Rosenthal
All right, let's go there. How'd that happen?
- [09:02]
Andrew Ross Sorkin
Okay, so backstory is, I'm 15 years old, I gotta 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. And 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. And 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. So we did it. And about a year into this project, New York Times wrote a little article about this little endeavor. My mother used to drive me down to the New York City to different advertising agencies because I'd have to go sell my ads. And they were cheap. I mean, cheap on a relative basis, like 900 bucks, 1200 bucks for a full page ad, blah, blah, blah.
- [10:06]
Ben Gilbert
Yeah, but for you as a high school student, this is amazing.
- [10:10]
Andrew Ross Sorkin
Huge. Anyway, it succeeded and failed. By the time I was about 18 years old, it succeeded in that we had gotten all these high schools to agree to take it. Some schools were getting it, some schools weren't. And 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, like, professional.
- [10:40]
Ben Gilbert
Meanwhile, your mail building was a great mistake.
- [10:43]
Andrew Ross Sorkin
And then we had hired a printer, actually the same printing company that was printing Wired magazine at the time. And 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. And 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. I mean, he was like a God to me. I mean, most people, you know, read the front page of the paper, the sports section. I would go to, like, page C6 to read what Stuart had to say. So I could go down to these meetings with the Advertising Age agencies and pretend like I knew what I was talking about. And all I wanted to do was work for this guy. And I was trying to find all these different ways to get into the Times and get to him. And I used to go home during high school and call him on the telephone to try to try to get a gig. And then finally he took me out to lunch and somehow convinced him to let me stay. And then there was a guy named Glenn Craymond who was running the business section, and he let me stay. And so I used to come every day with a visitor pass to. There's a union at the time. So 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 and I'd xerox and staple. I had no intention of putting two words together, let alone a sentence. This is 1995, and happily, an editor who had no idea how old I was. I was wearing a suit with a tie back then. And she thought I was like a real person. And she assigned me a story to write. And that's how it all started.
- [12:23]
David Rosenthal
No way. Like a mistaken identity. Thing is how you wrote your first piece at the Times.
- [12:28]
Andrew Ross Sorkin
I think she thought I was like a young maybe news clerk graduate from college. She overheard me talking about this thing called the Internet back in 1995, and she thought, oh, he may. He seems to know what's going on.
- [12:40]
David Rosenthal
Do you remember the piece?
- [12:41]
Andrew Ross Sorkin
Oh, absolutely. It was the silliest piece, but it was. I mean, I love it so much. It was. You're gonna 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, comma, a device that transmits data over a phone line. And all these adults.
- [12:59]
Ben Gilbert
Well, now you need that knows what it is.
- [13:02]
Andrew Ross Sorkin
Nobody even knows. My kids don't know what a modem is. And she wanted to understand what that noise was. That like, you know, that high pitched noise. And I was trying to explain to her that the noise was. They were mating. The two modems were talking to each other.
- [13:20]
And that was the first article out of the gate. Wow.
- [13:23]
Ben Gilbert
So did you start full time?
- [13:26]
Andrew Ross Sorkin
No, sorry. I went to Cornell. I was gonna be like a camp counselor that summer. And then they asked me to stay for the rest of the summer. Then. Then I went off to Cornell. And then at Cornell I would continue writing for the paper, freelance stories and things. And 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 like 2, 3 in the afternoon, which was like 9 or 10 in the morning. So I would often be writing articles almost every day, little articles. But it was just a great sort of education for me.
- [14:00]
David Rosenthal
I want to go to the beginning of Dealbook. I am still astonished at how early this was in email. I mean, you look at. When did substack start? 2016, 17, I think.
- [14:12]
Andrew Ross Sorkin
2016. 17. Yeah.
- [14:13]
David Rosenthal
Ben Thompson started writing 2012. 2013.
- [14:16]
Ben Gilbert
2012. I think it was 2013. Yeah.
- [14:18]
David Rosenthal
I had no idea that Dealbook predated all of this.
- [14:22]
Andrew Ross Sorkin
That was a really remarkable period. So, yeah, it's 2001. I had lived in London after I went to Cornell. I'd been covering mergers and acquisitions, trying to break his stories and be as competitive as we could be. I get back to New York, I'm supposed to cover M and A. I'm thinking, okay, this is going to be easy pickings. I thought it was hard in London because the New York Times, you know, wasn't the local paper. And I started to meet bankers and lawyers and people in that whole netherworld. And they'd say, sorkin, you seem like a nice kid. But, you know, we get the Times at home. And I read the front page sometimes the sports section, and then I leave it with my wife and I take the Wall Street Journal with me on the train. And 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? And 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, and everybody else is doing the same thing. And 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.
- [15:35]
Ben Gilbert
And there'd been a history of newsletters on Wall street, but they were faxes, right?
- [15:40]
Andrew Ross Sorkin
Yeah. I mean, you could get all sorts of, you know, 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 Deal, 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 like a regular thing. Could you please fax us Dealbook? And 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.
- [16:11]
And they didn't really get that. So that was the sort of original conceit. And inside the Times, I will say there was sort of support, but sort of marginal because I think most people didn't understand what we were trying to do. And the other piece was part of the conceit was we were going to link you oftentimes to our competitors. So 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. So, you know, when Lucent was buying Alcatel, or rather I should Say Alcatel was buying Lucent. You know, we would translate parts of Le Monde. We would send you to the Trenton, you know, Times, give you what they were saying about a deal or what the local issue was in Dallas, if there was some, you know, something going on in the oil patch or something like that. So 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.
- [17:18]
Ben Gilbert
There must also been a ad sales and business model question too, right?
- [17:22]
Andrew Ross Sorkin
Well, in the beginning, so a couple of things. I was really trying to launch this thing in the ashes of what was. This was the dot com bust 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. And 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. I think 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 to put it in a mod. I don't think we ever used the phrase TAM back then, was 30,000 subscribers for free.
- [18:11]
David Rosenthal
And what is it today, if you're willing to share?
- [18:14]
Andrew Ross Sorkin
We're over a million. We're over a million subscribers.
- [18:17]
Ben Gilbert
This sounds very like Ben and my own Journey. In the early days, we used to be like, oh, there can't be more than 10,000.
- [18:25]
David Rosenthal
There's 10, 20,000 people who will listen to this?
- [18:27]
Ben Gilbert
Who would listen to this? Yeah.
- [18:29]
Andrew Ross Sorkin
So, you know, and I had this thought that we get the whole thing paid for by advertising. I was not looking to, you know, 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. And 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. We did. Our original advertiser was Brooks Brothers. It was our first advertiser.
- [18:56]
David Rosenthal
Awesome.
- [18:56]
Andrew Ross Sorkin
Brooks Brothers is still in business, but only by a hair, I think. I mean, I think they've gone in and out of business a couple times.
- [19:03]
Ben Gilbert
Were you doing the ad sales?
- [19:05]
Andrew Ross Sorkin
I was not doing the ad sales. So 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 months it felt like the thing had sort of 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'd 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.
- [19:43]
Ben Gilbert
Was there a cool dynamic where people who you were covering would subscribe and then would reply to the email?
- [19:52]
Andrew Ross Sorkin
Oh yeah. I mean that was actually, I mean even to this day, that's the coolest part about it, which is just the audience is so crazy. Crazy. I mean, in some of the names that get it every day that oftentimes they would reply. I mean people used to send us. They still do. I get PDFs of decks, you know, about a deal that's going to be coming within two days or you know, ahead of time, someone's leaking us something or people are replying to this saying, you know, I'm involved, I'm involved in this transaction. And by the way, you didn't get this right. I want to tell you what actually really happened.
- [20:21]
Ben Gilbert
What a great reporting channel. Just the replies to.
- [20:24]
Andrew Ross Sorkin
Yeah, no, the replies are a huge sense, just that immediate feedback that you get. And that actually was a huge sort of plus. I think it's funny now, I think 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 because, you know, we didn't have Twitter or X or any of these other social media platforms didn't exist back then. So this was sort of like an original way to do that.
- [20:50]
David Rosenthal
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?
- [21:11]
Andrew Ross Sorkin
So my view is that every source has some motivation for why they're talking to you. And oftentimes, if not all the time, it is self motivated. Meaning like 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.
- [21:40]
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, 10 people want to do a deal. One of them thinks the deal is 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.
- [22:43]
But was convinced that if the public markets understood that they were contemplating this, they would cheer and the board would actually be sort of put into a corner. The opposite way to do a deal.
- [22:55]
Ben Gilbert
We just finished recording our Coca Cola episode. I don't know if you remember this. The CEO of Coca Cola struck and announced. Announced a deal to buy Quaker Oats.
- [23:05]
Andrew Ross Sorkin
I worked on it that night. I remember that night. I remember that night like it was yesterday.
- [23:09]
Ben Gilbert
Yeah. And Quaker Oats owned Gatorade, which was the reason to do it.
- [23:12]
Andrew Ross Sorkin
The press releases were ready.
- [23:14]
Ben Gilbert
The two CEOs did a joint announcement, and then the Coca Cola board killed it after the announcement. Unbelievable. And then Pepsi ended up buying Quaker Oats and Gatorade. And it's been a home run grand slam for them.
- [23:28]
David Rosenthal
David, I love that you're telling Andrew this. I'm pretty sure Andrew knows.
- [23:32]
Andrew Ross Sorkin
No, but it's a great story, and it's an example of just how these things happen, where, you know, from the outside it all looks, you know, very organized. Oftentimes you see a big announcement and there's a press release, but behind the scenes, invariably there's a lot of different egos and personalities that have their own sort of plans, if you will. And 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, you know, 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. So there could be an auction for something. Someone's now lost the auction. Now they're jilted, the jilted lover. And now if they have any incentive in life, you know, 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, you know, 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. And 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 sort of like in the flow, calling around, talking about different things, sometimes it just comes up in conversation where, you know, people are maybe willing to say, it's like one of those, they're having a bad day, you might be talking about something else and you might say, what else is going on? And they might say, well, you know, I gotta tell you, I just got totally screwed on this situation. You should check out this other thing because that's, you know, and that's how a lot of stories like this start.
- [25:35]
Ben Gilbert
You get a beat like that. You say, you know, you need to confirm it with 2, 3, 4 other sources. How do you decide who to then call next?
- [25:44]
Andrew Ross Sorkin
Well, then I start to think through, okay, who in my sort of network that I've tried to develop relations 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.
- [25:59]
David Rosenthal
I know X. Can you confirm or deny?
- [26:01]
Andrew Ross Sorkin
Yeah, that doesn't really work. You sort of need to get enough information, usually at lower levels, to know, you know, where the meetings are happening, when they're planning on announcing. What's the price? If there's a. If it's a stock for stock deal, what's the ratio? Is there a collar to the ratio? I mean, I always say you want to get 80 to 90% of the way there before asking the company for comment, if you will. And I will say that once you, if you get to 90% of the way there, oftentimes it behooves the company in some ways to tell you what's actually happening at that point.
- [26:36]
Ben Gilbert
Yeah, they'd rather have a hand in shaping the narrative versus not typically.
- [26:42]
Andrew Ross Sorkin
Yeah, Most companies do want a hand in at least to tell you what's going on. And look, my view is it makes the 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. And I think it makes it a better story to include whatever the other side of the story is.
- [27:08]
David Rosenthal
Yep. Okay, so 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 we have a lot of the same. What we do rhymes as sort of this business historians, even though we're not.
- [27:24]
Ben Gilbert
We're just doing it about the past, not the. But it's similar, you know, different. People remember things very differently, as you know. You know, you're a historian, too.
- [27:32]
Andrew Ross Sorkin
Well, it's very interesting to try to think back. I mean, I just finished this 1929.
- [27:36]
David Rosenthal
Book, 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.
- [27:45]
Andrew Ross Sorkin
You guys are in the audiobook. I'd never done anything like that before. But what I was gonna 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 know, you're dependent on letters and diaries and memos and 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, you know, 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.
- [28:26]
Ben Gilbert
Think about that, but 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 trying to think of an example, maybe like Standard Oil. It really is, like, incredible drama. Right. And, like, ruthless stuff that's happening. And 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. And there's a way to talk about it of, like, you're not going to believe what Henry Flagler did next. Like what an animal, that guy, you know?
- [29:06]
David Rosenthal
All right, listeners, now is a great time to thank one of our favorite companies, Shopify.
- [29:12]
Ben Gilbert
Yes, and this is really fun because we have been friends and fans of Shopify for years. We just had Toby on ACQ2 to talk about everything going on in AI and everything that has happened at Shopify in the six years now since we covered the company on acquired.
- [29:28]
David Rosenthal
It's been a pretty insane transformation for them.
- [29:31]
Ben Gilbert
Yeah. So back at their ipo, Shopify was the go to platform for entrepreneurs and small businesses to get online. What's happened since is that is still true. And Shopify has also become the world's leading commerce platform for enterprises of any size. Period.
- [29:48]
David Rosenthal
Yeah. So what's so cool about the company is how they've managed to scale without losing their soul. Even though companies like Everlane and Vuori and even older established companies like Mattel are doing billions of revenue on Shopify, the company's mission is still the same as the day Toby founded it. To create a world where more entrepreneurs exist.
- [30:08]
Ben Gilbert
Oh yeah, Ben, you got to tell everyone your favorite enterprise brand that is on Shopify.
- [30:13]
David Rosenthal
Oh, I'm saving that for next episode. I have a whole thing planned for episode two of this season.
- [30:18]
Ben Gilbert
Okay. Okay, great. Anyway, the reason enterprises are now also using Shopify is simple. Because businesses of all sizes just sell more. With Shopify they built this incredible ecosystem where you can sell everywhere, obviously your own site. That's always been true. But now with Shopify, you can easily sell on Instagram, YouTube, TikTok, Roblox, Roku, ChatGPT, Perplexity, anywhere. Plus with shop pay their accelerated checkout, you get amazing conversion and it has a built in user base of 200 million people who have their payment information already stored with it.
- [30:56]
David Rosenthal
Shopify is the ultimate example of not doing what doesn't make your beer taste better. Even if you're a huge brand, you're not going to build a better e commerce platform for your product. But that is what Toby and Shopify's entire purpose is. So you should use them.
- [31:11]
Andrew Ross Sorkin
Yes.
- [31:11]
Ben Gilbert
So whether you're just getting started or already at huge scale, head on over to shopify.com acquired. That's S-H-O-P-I F Y.com acquired and just tell them that Ben and David sent you.
- [31:24]
David Rosenthal
Well, Andrew, I was going to ask you, how many years was it of the newsletter before starting the Dealbook Summit?
- [31:30]
Andrew Ross Sorkin
So we started the summit in 2011 in fact. So we'd basically been doing it 10 years, 10 years in. And really the summit was just the idea of can we bring the pages of DealBook to life? Right? Could we actually take all these characters who we were writing about every day, who oftentimes were replying to us on the email and put them on a stage and talk to them in a really human way so that people could, and the public could sort of 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 less about. I mean, I care about, you know, 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.
- [32:28]
David Rosenthal
I've thought that watching the last few years of DealBook Summit interviews, I mean, 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 a hour long interview, a lot.
- [32:51]
Andrew Ross Sorkin
Of them go between a half hour and an hour. And in terms of the reporting, you're right, it's not, you know, oftentimes news of the moment, though sometimes they do make news in that moment that make headlines.
- [33:02]
David Rosenthal
Alex Cooper dropped her energy drink.
- [33:05]
Andrew Ross Sorkin
She did, 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. So 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.
- [33:34]
David Rosenthal
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 Earth and what's going to be necessary to accomplish all of that?
- [33:56]
Andrew Ross Sorkin
Yes and yes. And because he made a particular point of leaning in to AI and I remember being a little surprised about sort of his interest in Artificial intelligence and how he, he clearly wanted to talk more and more about artificial intelligence. And I remember thinking to myself, well, you know, Amazon doesn't have its own large language model right now. You know, arguably it's behind. I mean, I think a lot of people thought that at the time. And here's a guy who 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, you know, it's that important.
- [34:40]
So last night when I learned about this, I thought, oh, okay, this all makes a little bit more sense now. And he's going to become the co CEO of the company, which to me is remarkable because he hasn't been. He was not the CEO of Blue Origin, he was the founder, but he had hired someone to be the CEO. And the last time he'd been the CEO of a company obviously was Amazon. So 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.
- [35:08]
Ben Gilbert
When you were starting the Summit back in 2011, did you think about it as like, we have this amazing readership and engagement of people replying and like, 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.
- [35:39]
Andrew Ross Sorkin
I think it was a combination of both of those things. And 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 this sort of confluence of finance and Wall street, tech and policy out of Washington. So our first deal book, Jamie Dimon, I think was the opening speaker. Lloyd Blankfein, Marc Andreessen, Eric Schmidt, Dick Costello, who's running Twitter at the time, those were some of like the big leaders back then who we had. And then I think, you know, the second year, Ken Griffin and Dan Loeb, Preet Bharara, who was at that point running the Southern District of New York.
- [36:39]
So that was really the backstory of what we were, we were trying to do. And we thought there was an opportunity to elevate all of this, but I don't think we knew where it could all go.
- [36:49]
David Rosenthal
To me, this is the flagship set of interviews for the year. I mean, 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, and you do eight of them back to back in one day. How do you prep for that? What does this process look like?
- [37:11]
Andrew Ross Sorkin
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 the people who make it to the stage, some people who are set on my wish list 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 sort of 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, like, their disposition and sort of 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 teams, you know, PR teams and other people who reach out. And so I do like to sort of 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 like 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, you.
- [38:52]
Ben Gilbert
Know, 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. And he's like, no, no, no.
- [39:02]
David Rosenthal
We did ultimately do a quick call from our dressing room when we were in rehearsal.
- [39:06]
Andrew Ross Sorkin
Right. But it's just 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 sort of coming off for a minute or two after, you know, 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. Because people come in, they're a little anxious, a little nervous, and 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. Like, however, you can sort of meet them where they are before it begins, I think is a huge thing that I try to do.
- [39:53]
Ben Gilbert
That's so true. Chase Center. Mark. 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.
- [40:06]
Andrew Ross Sorkin
No. And it's like, how do you meet that other person where they are? And everybody comes to it totally differently. There's some people who come, you know, 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, sweaty hand, you know what's about to happen.
- [40:28]
David Rosenthal
So our squawk box experience, we felt very. I mean, look, David and I are business historians, and we've watched so much tape of Squawkbox, and walking onto the set almost felt like this weird, like, Disneyland experience. Like, whoa, this is what it looks like in real life. And 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, like, literally ignored us. One foot away. And it was complete night and day experience.
- [41:03]
Andrew Ross Sorkin
Well, thank you for that. We always say we think we should start a streaming show during the commercial breaks because we. What happens during the commercial breaks is oftentimes as fun, if not crazier than what happens. And we're all on. It's, like, 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. Because there have been times where I've. Some, like, news is breaking or something's happening, and you feel like you have this, like, 90 seconds between commercial and you have to, like, study the thing so you know what's going on. I don't know if that was your circumstance.
- [41:39]
David Rosenthal
This was not that. But I could See, that being a very valid reason to.
- [41:43]
Andrew Ross Sorkin
I've had that and I've felt bad about it because there have been a couple of times where I've like stared straight at the screen and not really looked up. And I probably should have. And maybe the person next to me was like, what is going on here? And I've been like, in my own thoughts.
- [41:56]
Ben Gilbert
You guys in Squawkbox, you put a lot of thought and effort into the guest experience. Like you had a car pick us up. You know, 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. Like, it's just, oh, you don't have.
- [42:12]
David Rosenthal
To do your own makeup.
- [42:13]
Ben Gilbert
Yeah, you don't have to do your own makeup. Like, this is night and day versus the rest of the industry.
- [42:17]
Andrew Ross Sorkin
We want it to be fun. And I think actually one of the reasons people keep coming back and wanna come on the show is like, 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.
- [42:33]
Is a fun experience.
- [42:34]
Ben Gilbert
Well, I can tell you, I mean, as guests, it felt like you really valued our time and experience. It didn't feel like we were the commodity filler for the that 10 minute segment. It was like.
- [42:48]
Andrew Ross Sorkin
But that's the thing. There is no commodity filler. I mean, honestly, whether you're Barry Diller or Jamie Dimon or an analyst who's studying a stock, I think we all think that each of these component parts over the course of three hours has huge value to the broadcast.
- [43:05]
David Rosenthal
Okay, so 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 videos come out.
- [43:14]
Andrew Ross Sorkin
So we've got everybody from Secretary Besant, 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 chessboard 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, you know, 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.
- [44:07]
And she's now going to be running Turning Point, which is hugely influential in the conservative Republican movement. So I think trying to understand the way she's thinking about that could be really, really interesting.
- [44:17]
Mary Barra, probably most influential, powerful female CEO in America, runs General Motors. She's in the middle of it all. I mean, talk about manufacturing in America and the whole tariff story. Dario Modi, who runs Anthropic, I think he's one of the most personally interesting people in artificial intelligence. And 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 in the political class is doing. President Trump has made some comments about him, so I'm very curious.
- [44:54]
Ben Gilbert
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.
- [45:06]
Andrew Ross Sorkin
All have his fingerprints. So I think spending some time with him I think is going to be really interesting. Alex Karp, who's the co founder with Peter Thiel of Palantir, runs Palantir, and I think that's been considered one of the hottest stocks, clearly, but also one of the most interesting stories and companies in the country. We're going to do a conversation with what I call the young OG and the old OG of finance. So we're gonna put Brian Armstrong and Larry Fink together.
- [45:34]
David Rosenthal
Are you doing every one of the interviews you mentioned so far?
- [45:37]
Andrew Ross Sorkin
I do all the interviews. So every interview on the stage, I do. We started doing that maybe in the third year of the conference.
- [45:46]
David Rosenthal
Okay, so keep going.
- [45:47]
Andrew Ross Sorkin
And then we've got arguably the most influential, powerful influencer in the world, Jimmy Donaldson, better known as Mr. Beast. So my children want to come to Dealbrook this year for that very reason.
- [46:03]
And 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.
- [46:18]
David Rosenthal
Okay. You're doing all this in one day?
- [46:22]
Ben Gilbert
It sounds insane.
- [46:23]
Andrew Ross Sorkin
And Halle Berry. Halle Berry. Halle Berry. Halle Berry.
- [46:27]
David Rosenthal
How could you forget Halle Berry?
- [46:28]
Ben Gilbert
Forget Halle Berry.
- [46:28]
Andrew Ross Sorkin
Can't forget Halle Berry. So, yeah, so I'm gonna do this. I'm usually on stage from call it 9 in the morning to 6 or 6:30pm and it's an all day marathon. It's like sprinting A marathon.
- [46:41]
Ben Gilbert
I assume you're gonna take the day off from Squawk Box.
- [46:44]
Andrew Ross Sorkin
I take the morning off. I usually go on for, like, five minutes in the morning and sort of tease what's going on all day.
- [46:49]
Ben Gilbert
But, yeah, okay, you go on Squawkbox before all this. This is insane.
- [46:53]
David Rosenthal
I'm just thinking about just the amount of prep and, like, I mean, truly, the CPU of my brain is redlining going into a Zuckerberg interview or a Ballmer interview or a Jensen interview, where, like, my job and David's job. David's job is more of the story. My job is more the reflection and the analysis is to make sure that we leave that interview. And with. Did we give the listener important takeaways, like, 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, and it takes everything I have to do that. And 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?
- [47:40]
Andrew Ross Sorkin
For me, I have to absorb all of the information in advance. I need to almost, like, know it at a visceral level so that it's not about notes or anything else. It's like, you know it. Because there often isn't a lot of time, even between interviews, to sort of recalibrate and rethink, sort of, okay, I've got to start this new one. So it really is, for me, about sort of feeling it, if you will, and having read so much and having spent so much time thinking about the different ways it could go. And I do think a little bit, the sort of 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 gonna change. But, you know, I know that I'm starting at jfk, and I know I'm ending at lax, and I know I'm probably going to land at o', Hare, maybe Atlanta, Denver, and, you know, Dallas.
- [48:37]
David Rosenthal
We may not pay ATC along the way, so who knows what detours are gonna happen?
- [48:41]
Andrew Ross Sorkin
But I also know the weather's gonna change. And so, you know, my ambition to get to o' Hare first might get upended pretty quickly, and we might have to divert to Atlanta first. And then how am I gonna pivot back if I need to, if I wanna go back there? So I think that, for me, it's sort of like having a little bit of a path, but Then listening to me. And 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're 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.
- [49:27]
David Rosenthal
And if you can get the subject to sort of 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.
- [49:40]
Andrew Ross Sorkin
I remember interviewing Bill Gates. It was 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. And I thought, okay, we're here now. We can do this.
- [50:04]
David Rosenthal
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. And so if you can get that game recognized game moment where they're like, oh, you, you really did a lot of work on this. I just feel like that that's where a lot of the. The beauty comes from. After that.
- [50:29]
Andrew Ross Sorkin
Well, I think that a lot of people have an enormous amount of mutual respect for you guys because they. They see it. They see the work. And the work is so evident when they listen to you. Because the 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.
- [50:53]
Ben Gilbert
That's a great point. You're bringing your whole body of work to the interview. And your subjects have that experience too, hopefully.
- [51:04]
Andrew Ross Sorkin
Yeah. I mean, that's what you want. Yeah.
- [51:06]
David Rosenthal
All right, let's talk logistics, and then I want to talk about the business. So at cnbc, you have a producer team. We got to interface with some great people who helped us prep. Who prepped you? There's teleport prompters, there's notes. What does the producer side of Dealbook Summit look like?
- [51:23]
Andrew Ross Sorkin
So the producer side of DealBook is we do have a fantastic events team that's doing a lot of sort of the organizational work. Just because there's obviously hundreds of people in the audience. There's all the participants who are on the main stage. We also have a series of these things called Task Forces and Groundbreakers. There's a lot of sort of moving pieces for the interviews that I do.
- [51:49]
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 sort of 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's some great, great beat reporters at the Times who obviously live and breathe particular topics and CEOs and businesses. And I'll reach out to them and say, you know, what are the five questions you think absolutely need to be asked? Or are there particular places.
- [52:32]
That you think I can go or different ways to get there? Because 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.
- [52:46]
David Rosenthal
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. And how do you get to that really interesting topic without making the whole thing awkward and depriving the audience of a good interview?
- [53:02]
Andrew Ross Sorkin
You know, and I want the other person to hit the ball back. Like I always say, you know, here we are talking about airplanes. It's also a little bit like a tennis rally. You want the ball to go back and forth. So 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. Like, I do want them to hit the ball back. And so it's a question of, you know, 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. And sometimes it's complicated because I do feel, again, I'm curious how you guys think about it in the context of, you know, I'm a journalist, you guys say you're not journalists. And sometimes there's questions or issues that are really difficult that I want to and feel like I want the interviewee to grapple with. And 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 is 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, and I'll read the quote aloud. And 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. There's this thing. It's in the public domain. The public is thinking about this. So it's also. We're all. Everybody's thinking about this. How do you think about it? And 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, it's that they've read the quote. They've grappled with that quote, oftentimes for weeks on end, because they're either annoyed by it or they think there's another. And so it's not an impossible question to answer.
- [55:09]
David Rosenthal
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?
- [55:25]
Ben Gilbert
You would say what? Yeah, yeah, yeah.
- [55:28]
David Rosenthal
I just love it.
- [55:29]
Ben Gilbert
You literally call it, you know, the angioth Sarkid. Phrasing.
- [55:35]
Andrew Ross Sorkin
My. My wife is going to laugh when she listens to this part of the podcast.
- [55:39]
David Rosenthal
Why tell us?
- [55:41]
Andrew Ross Sorkin
Because I use that with a lot.
- [55:42]
Ben Gilbert
Of things I could imagine. If you are your, you know, your spouse, that would be extremely annoying.
- [55:49]
Andrew Ross Sorkin
What would you say? How do you think about that? Yeah, no, I have a whole. I have a whole bunch of friends who always sort of mock little phrases that I use.
- [55:59]
Ben Gilbert
How do you guys think about the set and setting for these? Like, you have a whole set of choices that you could make about number of attendees, who those attendees are, the stage design, you know, like, it's very sparse, but you could be more intricate. I'm sure these are all intentional choices.
- [56:15]
Andrew Ross Sorkin
So I think the audience is as important as who's on the stage. And I often say that a lot of the people in the audience could clearly be on the stage. And 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 are peers in many Ways I think we try to.
- [56:36]
Have a good mix between sort of business leaders, the political class, the sort of academic universe, the sort of journalist, public intellectual culture kind of group, so that there's sort of a really interesting mix in the room. And I think we've every year 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 four or five hundred people in that room, and it doesn't feel like that. So I think there's something very special about that. And then the truth is we just use a sort of massive LED screen behind us because you can almost paint whatever you want on it at any moment. And that's the set.
- [57:38]
David Rosenthal
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.
- [57:50]
Andrew Ross Sorkin
That's just like a branding like we. Because in those pictures get used, you know, repeatedly throughout the year. And I think now people look at that background and they just know, oh, that happened at Dealbook.
- [58:01]
Ben Gilbert
I was actually at a gala dinner in that room a couple months ago. And it was like the most bizarre thing of like, you know, it's a totally different setup. There are all these round gala tables there. There's, you know, like a. And it's like this feels very familiar, you know, but an entirely different context.
- [58:20]
David Rosenthal
For a certain business, political, technology, segment of the world. That. It's almost like that room is typecast like that. That room can't have another role in.
- [58:30]
Andrew Ross Sorkin
The world for our crowd. Yes.
- [58:32]
David Rosenthal
Yes.
- [58:33]
Ben Gilbert
Yeah.
- [58:34]
David Rosenthal
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?
- [58:43]
Andrew Ross Sorkin
So look, I think 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, culture leaders, and it's just a spectacular audience. It's driven by advertising. It is not a. It's not a paid, you know, separate, paid subscription.
- [59:12]
David Rosenthal
Is it a Dealbook specific advertising team or part of the Times? All up advertising?
- [59:17]
Andrew Ross Sorkin
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's People in the advertising department that work on that. And then the event itself is really, as I said, a manifestation of the newsletter. And 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. So that is the business.
- [59:49]
David Rosenthal
So 100% sponsor supported, no direct monetization of the entire thing.
- [59:54]
Andrew Ross Sorkin
There's no subscription model for the newsletter. For me, the truth is we've always wanted, if we could, to punch above our weight in terms of reaching the most influential people in the world. That that was really our goal more than any anything else. It was, it was really just, it was about reach. And we found that we can make the economics of the business work pretty well under this scenario.
- [60:21]
Ben Gilbert
And does that apply to Summit too? Like, can you buy a ticket to Summit? Or you don't buy tickets. It's only sponsorships.
- [60:27]
Andrew Ross Sorkin
Our readers can apply effectively to buy a ticket for the event. And so we do maintain a group of tickets that are available for readers and the public who want to participate.
- [60:42]
Ben Gilbert
But you're still curating the room.
- [60:45]
Andrew Ross Sorkin
But we're still curating the room. And we're also super intent on making the event as public and available as possible to the public. So, you know, within 24 hours of the event, you know, all of the interviews are available for free, not just on NY Times, but on YouTube and other platforms.
- [61:06]
David Rosenthal
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 sort of least risk tolerant founders I've ever met. This all happens slowly, accidentally, and with almost no risk. And 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, you know, it was actually a pretty conservative choice and it just happened to work out well.
- [61:46]
Andrew Ross Sorkin
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 gonna have to give the money back. Like, 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 gonna be able to do this. So 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. And I was super scared the whole time. And really, the first couple years, I wasn't even sure I was gonna 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 Bryan Kopman 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 gonna get anyone to buy that thing.
- [62:48]
David Rosenthal
On spec means you do all the work to write it.
- [62:51]
Ben Gilbert
You didn't have a studio giving you a development fee.
- [62:53]
David Rosenthal
No.
- [62:53]
Andrew Ross Sorkin
You 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. Once you had it all on paper. So 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 miserable. Still could, right?
- [63:18]
Ben Gilbert
Seems unlikely at this point.
- [63:20]
David Rosenthal
Well, actually, I thought this was the direction we 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?
- [63:33]
Andrew Ross Sorkin
So 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. So, you know, back in 2002, 2003 and four, I was going on the Today show back when Katie Couric and Matt Lauer were the hosts, and back with Charlie Rose. And I remember during the Martha Stewart trial, sitting at the desk there with Katie.
- [64:01]
And so 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. So it's probably elevated today to some degree. I think there's more people who sat 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 because I don't realize, I think a lot of people, 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. And so I don't even really think about it or acknowledge it until I sort of 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?
- [64:50]
Ben Gilbert
Yeah.
- [64:50]
Andrew Ross Sorkin
And I'd be like, I don't know. I think maybe they watch the show in the morning. I'm not sure.
- [64:54]
Ben Gilbert
Well, hopefully you have the same version of this that we have, which is our audience are, like, super smart, super curious, super wonderful people who we're always happy to talk to.
- [65:07]
Andrew Ross Sorkin
Totally. I mean, I find it so exciting when people come up to you and they want to give you a high five or they say they see you on the show or this or that.
- [65:13]
David Rosenthal
And while we're on the topic of tv, I do want to ask you about Billions. I loved Billions especially. I think the first few seasons are some of the best television that has ever been created. That succession. I mean, 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?
- [65:44]
Ben Gilbert
Yeah. You might start getting some replies from your sources via, like, you ripped me off for this character or that affects.
- [65:52]
David Rosenthal
Your brand as someone who covers the truth, not who makes up these fantastical worlds.
- [65:58]
Andrew Ross Sorkin
So I had been a co producer of Too Big to Fail. We had made a movie of Too Big to Fail for hbo. Paul Giamatti, who ends up in Billions, obviously, as Chuck Rhodes, was Ben Bernanke in Too Big to Fail. I loved that whole process of.
- [66:18]
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. And so I was thinking to myself, you know, is there some other kind of project I could do that's in the television world? And at the time.
- [66:36]
You know, 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 and 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 gonna be boring, Blah, blah, blah, blah, blah. And back then, I was just really thinking more about maybe a character that's kind of like Bobby Axelrod and sort of like around a family, a hedge fund and their family. And then I remember coming home and my wife was watching a rerun of Law and Order on USA Network, and I said to her, you know, what kind of shows work? Legal shows work. People love a great procedural. Why is that? They just, like, eat these shows up. And 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 and maybe. And I had, by the way, 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. So I thought that was sort of like a unique way to. To approach the issue. I don't think I was so worried about the fictional nature of it. And my role was really in helping sort of put the whole thing on its feet. And then, of course, I met Brian and David, and they were the showrunners of the program, and they really took the whole thing and ran and were really great. I mean, if you love the show over all those seasons, give them the credit.
- [68:07]
David Rosenthal
Was it strange casting yourself?
- [68:10]
Andrew Ross Sorkin
Strange casting myself.
- [68:11]
David Rosenthal
There is a character that seems to.
- [68:14]
Andrew Ross Sorkin
Rhyme with what he did. I didn't think he really was me. I never thought about it that way. No, I never really did. I know who you're talking about, but I never, for whatever reason, I never thought he was pretending to be me.
- [68:27]
Ben Gilbert
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?
- [68:41]
David Rosenthal
There is a media empire here.
- [68:43]
Andrew Ross Sorkin
I don't know if it's an empire. I think of it more as I'm a journalist. I'm writing and 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 at the New York Times, and then are there things I can do that layer on top of those things? And they're all interrelated, really, whether it be.
- [69:14]
A fictional TV show or a book project or something else. It's just another way of telling the story and 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 and it gave me. I remember this and this and this and this. Or someone would read 1929 and learns about these different characters and people. I think I'm just sort of 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. You know, an economist might look at the world of 1929 or 2008 or a lot of things that are going on in our world and talk about in the context of economic cycles and systems and all sorts of things like that. And 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. And if you can understand the people and why they do what they do and you can really feel them.
- [70:41]
It'Ll change your outlook on everything and make it a lot more understandable.
- [70:45]
Ben Gilbert
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 like, no, I'm not thinking about this strategically. Of like, oh, my agent said I should add a podcast and so that'll amplify it. It's like, no, no, no, no, I'm doing like, there's a. 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 canvases doing that, but I'm always doing the same thing.
- [71:15]
David Rosenthal
What are some recommended best practices that you disagree with? What are some things that is canonical wisdom like David threw out?
- [71:24]
Ben Gilbert
Oh, yeah. Oh, you should have always good authors amplify what you're doing.
- [71:28]
Andrew Ross Sorkin
Well, so you guys probably think I do a lot of things.
- [71:31]
David Rosenthal
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.
- [71:37]
Andrew Ross Sorkin
Well, no, what I was gonna say is I feel like I do a lot of things and then I say no to a lot, a lot, a lot of things. And that I can't do anything well unless I spend an extraordinary amount of time on each of the things. So, you know, people have said, oh, should you do a podcast? Or something like that? And 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? And I'm like, well, how are we? So what I'm trying to do is it took me eight years to write that book, 1929. So I feel like in my own way, each thing takes a sort of 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, like, don't take it personally.
- [72:31]
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. And 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.
- [73:01]
Ben Gilbert
I've already tried to think of what a common criticism of Andrew Ross Sorkin could be. What do you hear?
- [73:07]
Andrew Ross Sorkin
So, you know, within the journalistic world there are people who think that you, you shouldn't know your sources or not know your sources, but some people would say, you know your sources too, too well.
- [73:19]
You're too close to your sources. So I'd say within the world of journalism, you know, one critique is you're too close to your sources. You know, my view is that the only way to tell this sort of truly human, nuanced story of the way they think is to know them. You have to know them somehow. And I think you can do that and still be objective. You know, there's lots of times, 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.
- [74:01]
And I think, or I like to think that the people that I report on respect that and actually respect it more. One man's view.
- [74:11]
Ben Gilbert
But I've, I've had conversations with people who you've reported on where they have said that to me of like, yeah, man, hate the, like, I, you know, I understand it, you know, like if they were talking about a piece on them by somebody else, I'd be like, ah, that, you know, SOB or whatever. But like with you, it's like they respect you.
- [74:30]
David Rosenthal
They don't understand.
- [74:31]
Ben Gilbert
Yeah, yeah, yeah.
- [74:32]
Andrew Ross Sorkin
You know, I think a great journalist in a way is a fair weather fan and what that means, though Is, you know, 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.
- [74:52]
David Rosenthal
That's a great framework on the take everything personally. And when you said, you know, what are you doing? It sort of 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 it? 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 like, don't take it personally advice kind of really depends on which of those things you think this is all for. And if the goal is do great work, you have to take everything personally.
- [75:28]
Andrew Ross Sorkin
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. And I think it'd be very hard to accomplish any of those things if you didn't take it personally.
- [75:50]
David Rosenthal
Yeah. 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 kind of had no unique angle to talk about 1929 because I was woefully behind on reading the pre advance copy. So 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.
- [76:21]
Andrew Ross Sorkin
Well, this has been a ball for me. And you guys know I've been listening to you for a very, very long time, and 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.
- [76:32]
David Rosenthal
Thanks, Andrew.
- [76:32]
Ben Gilbert
Likewise. Thank you.