title: "The Insane Productivity of Andrew Ross Sorkin"
author: "ACQ2 by Acquired"
source_type: podcast
content_hash: d8ca242d5f08887d1557f8e8414e403e7e2f322668f15fe146cc7053c2552e72
extraction_method: generic_website
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?
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?