Too Big To Fail - Interview with Andrew Ross Sorkin - Zing Talk


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Today our guest is Andrew Ross Sorkin, a journalist, and columnist for The New York Times as well as the founder and editor of Dealbook. How ya doing today Andrew?

Great to be here, I'm good.

Could you start off by telling us a little bit about your role at The New York Times and Dealbook?

I have a couple roles in the New York Times, I'm a columnist; I started originally as a merger & acquisitions reporter, and then started a little mini business called Dealbook, which started as a daily email and has now grown into a full fledged website. We actually have a mobile app and a host other products.

Now it's no hiding the fact that you're one of the youngest people around cited as an authority on Wall Street, economics, etc and that's in a leadership position of such a major media outlet. Could you talk a little about that rapid ascension and what you think brought you to where you are today?

I started here when I was 18 years old as an intern if you will, and I used to Xerox and staple. I had no intention of putting two words together, let alone a sentence. I got lucky very early on; an editor who didn't know how old I was assigned me a story to write, and didn't realize I was still in high school.

I've been doing this now for way over a decade, and when I graduated from school, I moved over to London, and the New York Times gave me a job out there where I covered mergers and acquisitions. This was during the M&A bubble around 1999, so it was really a trial by fire and a remarkable education. I moved back to the states in 2001, and one of the first things I did when I got back here was to start this thing called Dealbook, which was this email I used to send at 7 AM. I'd send it out to bankers, CEOs, hedge fund managers, and it really just grew. In the first year we had 30,000 readers, then 80,000, to over 200,000 getting the email every morning. Now we have the website, which gets over 2+ million people on it. It's been a remarkable little ride over the past few years.


I want to talk to you a little bit about your book, Too Big to Fail: How Wall Street and Washington Fought to Save the Financial System — and Themselves. It's truly incredible that you were able to chronicle the behind-the-scenes dealings in the financial sector. How were you able to do that?

I decided to write this book almost within a week or two from when Lehman Brothers failed. In many ways I think I was well suited. Having covered wall street for over a decade at that point I knew a lot of people on the street. I didn't actually know a lot of the main characters, but I was able to, through some old school traditional reporting, getting in front of the right people and asking questions, getting people to tell me stuff they weren't supposed to. The great thing about reporting is that you can get more information from talking to people, and then go back to the people who don't want to talk to you.

So I think a third of the people wanted to talk to me for the right reasons – sense of history, wanted to be helpful – another third probably talked to me for the wrong reasons – rewrite their legacy, and rewrite history – and I kept them honest. The last third, typically the group who doesn't want to talk to you – internal investigations, litigation – but once you end up talking to the first two thirds, the other third decides ‘oh my goodness, this guy has actually talked to a lot of people and done a lot of work, maybe I should talk to him.'

Highlight some of the most interesting experiences you write about in the book for our listeners.

I thought there were a couple big revelations for me. The first was the original TARP plan, was really written back in April, and the government had seen this train barreling down the track and had written an 11 page memo on what to do called “break the glass” as in “in an emergency, break the glass.” I remember doing some reporting and finding out Hank Paulson had actually held a meeting with the board of Goldman Sachs in Russia, in June 2008 at night in his own hotel suite, and I remember being somewhat shocked that something like that could happen. The real revelation more than anything else, was just how bad things were in September 2008.

I thought it was bad just looking at the tape every day, and the stories I was writing. When you really get into the room, it was worse, and that there was a real sense of panic. We were talking about not 10% unemployment, but 25% unemployment, that Morgan Stanley & Goldman Sachs were on the verge of bankruptcy, that General Electric was going to go bankrupt. As a merger guy I was just surprised at the role of government, and how the invisible hand became much more visible.

And the book was just optioned recently by HBO for a film. Are you getting ready to show the world that you can act in addition to being a superb writer?

They are pursuing the film, and they just hired William Hurt to play Hank Paulson. I don't have a role in it so far, there's no character called Andy Ross Sorkin. I'll be a spectator like everyone else.

Are you planning on playing any major role in that, behind the scenes or on camera?

I'm a consulting producer, so I participate in various conference calls, and I talk often with the screen writer, producers, and director for suggestions, and dialogue, and questions of accuracy. It's been a great education and very exciting.

I want to talk to you about Dealbook. That was one of the first sites of its kind when it started. What prompted the idea?

Two things happened, and it really goes back to the email. When we started the email it was really about “how can we get in front of this community?” We had this newspaper that got in front of a lot of people, but we wanted to truly get in front of them, and make sure people were reading everything. I was also spending an inordinate amount of time on the internet every day finding stories. I figured if we could aggregate stories that would be a really great service, and at the same time show off what we felt was our great competitive content.

The big issue was how do we take this audience, that is really only having that touch point with us once a day, how can we migrate this and have a tighter relationship with this community, and that's where the website came in.

With Dealbook or separately, what was the most interesting story you've ever covered as a reporter for The New York Times and why?

I'll give you three. The most interesting business story I covered by a mile was the vote upon management for a hostile takeover for $183 billion. It went on for six months, and I was flying from London to Dusseldorf in Germany, and it was a transformational deal in so many respects. The two actual stories that to me were more interesting; I was sent down to Cornwall England where the last eclipse of the century was happening. I got there, and it rained, so I went around and spoke to all the people there who had traveled there for this horrible experience.

The other one; I desperately wanted to see the Rolling Stones in concer, so I pitched a story for a technology behind the Rolling Stones and their concert series, as at the time they were the only ones doing these computer powered tours. So I ended up traveling with the band and doing all these things behind the stage.

Alright, we're giving you the loudspeaker now to break any piece of news or put out any opinion you feel is not getting enough attention or hasn't been sufficiently reported.

There's two things to me that haven't been sufficiently reported. It's really about what's happened to the country over the past year or two, and the civility, or lack of civility, that has really transformed the conversation and frankly its transforming the business conversation. It's become very personal. When I look at all the Wall Street titans that supported President Obama, and so many have turned on him, and you try to understand why. It has less to do with policy changes, and more of the personal nature of the rhetoric. It's around the sense that the President has called them fat cats, and vilified them in the press.

It's a larger issue of how we're all dealing with each other, and I worry that it has devolved. I don't remember it being at this very base level when I started writing, and its something that worries me irrespective of the implications on business. On the issues, I think one that while reported on again and again that we're not paying enough attention to because it seems so far down the road, is that I'm a debt hawk. When I wrote the book, it was about financial institutions. But I think about it in the context of California, or countries like Greece. Think about what happened with Lehman Brothers. At some point the confidence gets sucked out of the system. The banks decided they were no longer good for the money and wouldn't trade with them anymore. I'm worried that would happen on a larger score, and that's' a story we need to keep running down.

Alright, now that we've got the hard questions out of the way we have a few more light-hearted ones we ask all our first-time guests. What was your first, and what was your worst job?

That's hard for me, because my first job was at the New York Times, and I haven't had an opportunity to truly have a worst job, because I love my job. I guess I don't like shoveling snow? I've been remarkably blessed.

Tell us something about yourself that no one's asked you about in an interview.

Nobody ever asks me about my mother. I often get asked about my father, because people think of my father is either Aaron Sorkin, the screenwriter, which he's not, or they think he's Ira Lee Sorkin, the lawyer for Madoff, who he isn't either. My mother is a woman named Joan Ross Sorkin, and she's actually a playwright. If I had writing chops, or my interest in dialogue, narrative, or story structure probably came from her.

Okay – this last one is Benzinga's trademark question: What was the best, and what was the worst investment decision you've ever made?

That's a hard one, because I'm not allowed to invest in individual stocks. From an investment standpoint, my best decision was I bid on some mutual funds and got them out in September 2008, but I was stupid enough to not do anything with them after.

Thanks Andrew. That'll do it for this episode of Zing Talk. Remember to check out the latest market-moving information, commentary and trading ideas on

Posted In: Movers & ShakersGeneralAndrew Ross SorkinBenzinga PodcastdealBookNew York TimesToo Big To Fail