Interview with Dan Doctoroff
Contents
Dan Doctoroff is the CEO of Sidewalk Labs. He was the CEO and President of Bloomberg L.P. and the Deputy Mayor of New York City for Economic Development and Rebuilding.
NYC’s Hidden Gem
Max Raskin: I read you met your wife in your first year of college and you’ve stayed married to her all this time, which I think is pretty remarkable for the circles you run in. Combining that with all the development you did in the city, I wanted to ask: If you were a young guy in New York right now, of all the places you helped develop, where would you take someone out on a first date?
Dan Doctoroff: Probably Governors Island – it’s a romantic in its own way. It’s a new park lots of people haven’t been to – you can even do glamping (although maybe not for a first date!). And it is pretty undiscovered. Only about a million people go a year now. The High Line had 8.6 million people before Covid. People don’t really appreciate Governors Island yet.
MR: You were instrumental in the High Line – did you expect it to be as popular as it is?
DD: We thought it would be great, but never expected that it would be the phenomenon that it was. I will tell you the first time I went up there, I was actually disappointed. It was a cold February day – it was freezing and everything up there seemed grey to me. Even though I had actually used the High Line in the very first pitch I had done to bring the Olympics to New York, when I got up there six years later, it was like, I didn't quite get it. That said, it formed a key part of our strategy for the West Side. And so, I did become a big believer in it and figured out how to get it done. But I never expected to be like that.
What was interesting, though, is it illustrates a rule that I have about how cities copy other cities. Within the first six months after it opened, there were probably 35 High Lines under development around the world.
MR: Do you ever go there now?
DD: My office is right on it. So literally when I have 15 or 20 minutes, I'll go out and sit on the High Line and just either make calls or read stuff. So I'm there all the time.
MR: Do you exercise during the day? How do you break up your day?
DD: I don't get breaks during the day enough – it's actually a problem. My schedule is literally meeting after meeting after meeting after meeting. I think in the first quarter this year, I added it up, and there was something like 700 meetings. So, I don't have a lot of time during the day.
MR: Have you always been like that?
DD: Yes. Particularly once I entered government, I was just underwater the whole time. Even then at least you were able to get out and you had to go see people. Now with Covid, it’s literally physical or digital meetings back-to-back.
Doctoroff’s Dunbar Number
MR: Do you ever get nervous before meeting a dignitary?
DD: No. But I’m weird in that way. I don't get nervous when I feel prepared for a meeting, or I know what I'm going do or say. But I still consider myself half introvert, half extrovert. If I went to a cocktail party, and I didn't know anybody, I would be very reluctant to go up and introduce myself to someone. I really don’t quite understand myself.
MR: Do you think that’s common?
DD: I think there are a lot more introverts than it appears. But that introversion manifests itself in lots of different ways.
MR: How do you manage your time? Do you use your phone or a printed schedule?
DD: I just look at my phone. I try and leave a couple minutes between every meeting so at least I can read or reread what I was supposed to for the meeting.
In general, I get up really early, I work out, and then I leave myself maybe an hour to read through everything I needed to read through for the day. My assistant, Marla Pardee, and I have a running Google Doc where she writes down all the stuff I'm supposed to do, and I take it off when I finished. She's been with me for 29 years, so we get each other. She generally knows what I've done and what I haven't done.
MR: What’s the equivalent of eating your vegetables – is there something she’s hocking you to do that you don’t want to do?
DD: Signing anything. I have to say that DocuSign has been a huge boon. Before that, Marla would give me dozens of things to sign, and I just hated doing that. I remember when I was in government I oversaw the Department of Environmental Protection, and we were constantly buying pieces of land in the upstate watershed. Each one came with all these maps and documents, and anytime we had a purchase, I had to sign what would be dozens and dozens of signatures. I always resisted doing it. Anything that’s truly repetitive and time consuming, I don’t like.
MR: So I’m not blowing smoke here, but truly everyone who I know who knows you really likes you and feels a connection to you. Even before we started doing this you remembered a conversation we had like 10 years ago. How do you manage all those relationships in your head?
DD: It's very nice of you to say – I’m not sure it's true.
MR: It is – people do say that.
DD: I don’t know. I do care about other people. Part of the reason I have like 12 to 14 meetings a day is I probably over-accommodate peoples’ desires to see me. I have people from every phase of my life who I still advise on their careers. That extends to friends of friends. Probably for my own sanity I should make myself less available.
MR: How do you remember so much? Do you have a phonebook with notes for people?
DD: No – I think I have a pretty good memory for people I've had some kind of relationship with. The other thing that helps is Marla, who literally knows every single person I know. I’m 63 years old – we started when I was 34, five careers ago.
MR: Is she older or younger than you?
DD: She is a couple years younger than I am.
Interestingly, we're both from Detroit. She's been through the private equity days, the Olympic bid days, the government days, the Bloomberg days, the Sidewalk days – all the other stuff that I’ve done over time. She tries to enforce a little bit of discipline but often doesn’t succeed.
MR: A lot of people look up to you as a mentor – is there someone you really get excited about meeting with?
DD: I don’t know if it’s about getting excited about meeting with someone. I think I've been extremely fortunate to have several mentors throughout my life and career – interestingly, all roughly around the same age. There's Mike Bloomberg – we’ve had now a 20-year relationship.
MR: How often do you talk to him?
DD: Probably every couple of months.
MR: What’s the kind of thing you go to him for?
DD: Usually it's just to talk – nothing specific.
There’s was my first boss out of college, who was a well-known political pollster [Robert Teeter] – he and I remained friends until he died. There was Jay Kriegel, who was the executive director of the Olympic bid and a legend in New York. He died in late 2019.
But the person who most consistently has been a mentor is Peter Solomon. He hired me at Lehman Brothers. He let me leave Lehman to go work in private equity in a firm Lehman had helped to form. He happened to have been a deputy mayor of New York for economic development in Koch Administration. He convinced me to take the job in the Bloomberg Administration. He has consistently advised me in my life and career for 37 years.
I have been really fortunate to develop these relationships with people who are like a half a generation or more older than me.
MR: What is your preferred method of communication or staying in touch with people?
DD: Getting together. I’m not great on the phone – I don’t really like to talk on the phone. Video is better.
MR: Do you text?
DD: I’m not a super avid texter other than with my kids, my wife, and my family.
MR: Do you have a group chat with your family?
DD: We do have a group chat.
MR: Are you an active participant?
DD: I’m pretty active. I am generally ranked as the fourth funniest out of five.
They are pretty much the only people I FaceTime with.
MR: During the day if a kid calls you or texts you, do you drop everything?
DD: Pretty much, yeah.
The Sidewalks of New York
MR: What about meditation or yoga?
DD: I think that’s something I probably should do, to be honest. As I get older, I should do yoga.
MR: What do you do for exercise?
DD: A bunch of different things – I exercise almost every day. I probably do the elliptical three to four times a week early in the morning. I have a trainer that I see once or twice a week, mostly remotely now.
I ride my bike outside when the weather's okay.
MR: Where do you ride?
DD: It depends. If it’s during the week, around Central Park. If it's the fall or the spring, and we're here in the city, I love to ride around the city. I like to leave early. My favorite ride is down the West Side bike path, over the Brooklyn Bridge, through Brooklyn, around Prospect Park, back through Brooklyn, over the Manhattan Bridge, and then come up Third Avenue, believe it or not.
MR: How long will that take you?
DD: It's about 25 miles. If I go early enough, it'll take an hour and a half or something like that. I love it. I truly draw energy – even when there’s not a lot of people out – from the streets of New York.
MR: Do you know the song “The Sidewalks of New York”?
DD: Vaguely.
MR: I notice you have a Garmin on your wrist – what kind of watch is that?
DD: Fēnix 6.
MR: And you like it?
DD: I do. I like it a lot. I’m not a big Apple Watch kind of guy.
MR: What kind of bike do you have?
DD: It’s a Parlee, which is custom made.
MR: Where’s your favorite slice in New York?
DD: It’s probably what’s most convenient. I wouldn’t go dramatically out of my way. Roberta’s in Brooklyn I think is great, I love it.
MR: Is there anything you’ll go dramatically out of your way for food-wise?
DD: No, definitely not. I’m not really a food person. The reason for that is sort of a funny story. I grew up as a totally reformed Jew. I met my wife in college and she was (and is) much more observant. She keeps kosher and observes Shabbat for the most part. When we got married, I said I was going to keep kosher with two exceptions – one is sporting events and the other is when I’m with someone I knew before we got married and she’s not there. As a result, when I go out to eat, unless I’m with one of my brothers or an old friend, there’s not that much to eat. I’m just not a big food person.
MR: Do you keep Shabbos?
DD: If I have something I need to do, I will go do it.
MR: But generally will you schedule meetings for Saturday?
DD: No.
MR: Do you believe in God?
DD: I would say yes, but I wouldn’t say I’m a spiritual person.
MR: What about the afterlife?
DD: No.
MR: You think there’s a God, but no afterlife?
DD: I think there’s a divine presence, but I don’t think there is an afterlife.
General Manager Dan Doctoroff
MR: I don’t know if this is a sore subject, but are you watching the Olympics right now?
DD: Probably not as avidly as I would have in the past – part of that is the time zone thing. But I watch it.
MR: Do you have a favorite sport?
DD: In the summer Olympics, I’ve always loved track and field. When I was a kid, the NCAA Indoor Championships were always held in Detroit. My father would take my brother and me every year, so I've always loved track and field.
MR: Did you run?
DD: Not competitively.
MR: You played football.
DD: Up through ninth grade. In the ninth grade in the span of four weeks, I broke both thumbs, my collarbone, and my arm, and that was the end of my football career.
MR: In college you managed Harvard’s baseball team.
DD: Yeah, something I regret doing.
MR: Why?
DD: I don’t know, it was just a waste of time. I could have done a lot more. It’s one of my few regrets actually – not like a big one. Although I had made great friends. One of my college roommates went on the play in the Major Leagues.
MR: Who was it?
DD: His name was Mike Stenhouse. His dad was also one of the few rookies to start the All-Star Game.
Professor Scalia
MR: You were at the University of Chicago Law School during a pretty heady time.
DD: In a way I was. My contracts professor was Antonin Scalia.
MR: Wow. What was he like?
DD: He was great; he was funny. Here’s a story – and you’ll appreciate this as a law school professor and former law school student – it’s literally on the third day of contracts, and we're reading some case from the 19th century. And, of course, everyone is intimidated by everybody else. Scalia asked a question and this guy sitting in the first row, Mr. Miller, raises his hand. By the way, he’s now a professor of law.
MR: Sounds like a gunner.
DD: So he raises his hand and he gives his answer and he cites something in the footnote from this case from the 19th century. And Scalia says, “Miller!” And Miller puffs up his chest, and says, “Yes, Professor Scalia?” And Scalia says, “Miller – what are you doing!?” And Miller says, “Well I just cited the case in the footnote.” Scalia said, “Ah Miller! I never read the footnotes!” Which endeared him to everybody in the class.
But he was also a little lazy in other ways. When we had contracts, the 4th edition of the casebook had just come out Scalia would not use the new edition, forcing everybody to scurry all over Chicago and find used copies of the 3rd edition. This was in the days before there was the Internet and a market for used books. Now in fairness to him, he had just been appointed to the U.S. Court of Appeals for the D.C. Circuit, and so he wasn’t really too focused on teaching. We had amazing professors – Richard Posner, Frank Easterbrook.
The Sexton…Chopped Salad?
MR: Was Richard Epstein there?
DD: I had him for torts. I thought he was the smartest human being I had ever met.
MR: I interviewed him!
DD: I loved him, actually. He’s just so interesting. I bump into him on the streets sometimes.
I did my third year of law school at NYU because my wife took a job in New York.
DD: So did you graduate from NYU?
MR: No, from Chicago. For the last ten years I’ve been on the board of the University of Chicago. But I did become extremely close, later on, with John Sexton.
DD: Me too. He and I are really, really good friends. He credits me with his expansive vision of NYU as the Global Network University.
MR: Really?
DD: I don’t know if that’s true, but he credits me all the time.
MR: John is my rabbi in all things.
DD: Yeah, I love John.
MR: You both have this aura. Do you think you two are similar?
DD: Somewhat. I think we think strategically in the same way. I think he’s smarter than I am. I think he’s more outgoing than I am. But there are similarities, which is the basis for the friendship.
MR: What did you get at Volare?
DD: A salad.
MR: Do you remember what kind?
DD: It was chopped but I don’t remember what kind.
MR: You didn’t get the Sexton Veal Chop?
DD: No, because he doesn’t fall within one of the kosher exceptions. I didn’t know him before I was married. I got married before law school.
Burns the Midnight Oil
MR: Do you floss?
DD: No. I refuse. My dentist now insists that I come in every three months as compensation.
MR: Why do you refuse?
DD: I think it’s kind of gross. I don’t like it.
MR: When do you go to sleep at night?
DD: I’d say 10:30 to 11:00.
MR: Do you watch TV?
DD: Since I’ve been 10, I’ve watched TV to fall asleep.
MR: What do you watch now?
DD: Mostly it’s boring historical documentaries you can find on YouTube.
MR: Do you like Ken Burns?
DD: Love Ken Burns.
MR: The best.
DD: So I watched The Roosevelts in three-minute increments. I’d start watching and then fall asleep – even if I woke up in the middle of the night I’d have to go back and figure out where I was.
MR: Peter Coyote is the narrator. He ran with the Grateful Dead. He has such a calming voice.
DD: Oh, he’s got the greatest voice ever. I’ve watched every Ken Burns (and Ric Burns, too) documentary. I just watched the Hemingway one. Now I’ve started going back and reading all of Hemingway’s novels. I had read like one before.
MR: Just to show you I had the same idea after watching it. [Shows copy of Ernest Hemingway’s A Moveable Feast]. I just took my copy from my parents’ house all marked up from high school.
DD: That may be next for me. I just finished For Whom the Bell Tolls over the weekend.
MR: Do you read fiction?
DD: Yeah, a fair amount.
MR: Do you have a favorite novelist?
DD: Yeah, at different times, it's been somebody different. I love John Updike because I love those portraits of America at a certain time. Probably not popular to say, but Philip Roth for the same reason. My favorite novel is probably Robert Penn Warren’s All the King’s Men.
MR: Did you know Saul Bellow when you were in Chicago?
DD: I did not, but his son’s ex-wife is a very close friend of mine.
MR: I think he’s my favorite novelist.
DD: Yeah he’s great. I read a mix of fiction.
MR: Did you watch The Vietnam War?
DD: Uh-huh. I think the one I liked best was Baseball.
MR: Did you ever see The Ghosts of Flatbush Avenue?
DD: I have seen it – and I’ve seen John Sexton in there too. I’ve read, at least two times, maybe three, The Boys of Summer.
I'm losing interest in baseball now. I think it's just gotten boring, and the games take too long. But I love historic baseball. I could probably still name every winner of the World Series up to 1980.
MR: What team was your team? To me, I grew up with the late-90s Yankees.
DD: I grew up in Detroit, so up until I had been in New York for about 10 years, I rooted for the Tigers. The highlight of my youth was going to the fifth game of the World Series in 1968, where they came from behind being down 3-1. And the series was 3-1 for the Cardinals, and so it was the turning point in the World Series. I have even gone back and watched that game on YouTube. I was there with my dad and my brother, so it brings back lots of memories.
But then in the mid-90s – like ’94 – I switched to the Yankees.
MR: That’s a good time to switch.
DD: Yeah, it was great.
I’m quite frustrated by them this year.
MR: I know. I was a big Sanchez fan which also doesn’t help.
DD: I don’t like big hitters who hit for low averages. That’s the problem with the Yankees – they don’t hit against great pitching.
The Bloomberg 10
MR: How do you read books?
DD: It’s gone in waves. I’m back to hardcopy.
MR: Do you write marginalia?
DD: Only nonfiction.
MR: What’s the last nonfiction book you read?
DD: King Leopold’s Ghost and These Truths.
MR: I wanted to ask about your dieting bets because I do something similar with a friend of mine.
DD: My weight vacillates in part because I really like junk food. When I get to the upper end of the range, I have to lose it. I have forced my way back through a series of different diets to get back to the lower end of the rage. Those diets have included something called the GM Diet, which is crazy. In fact, I was golfing yesterday with Steve Ross, the real estate developer who’s a very good friend of mine – he was going on the GM Diet yesterday because I introduced it to him. But I have found the best way to diet for me is simply to count what I eat and write it down. It forces me to eat very simply and not eat crap.
MR: But do you still make the bets where you have to donate to a charity if you don’t hit your weight goals?
DD: I haven’t done that in a while – I used to do it a lot.
MR: My good friend Jack and I do those bets.
DD: We’d do it where you have to pay some odious charity if you lose.
MR: Ours are not just about weight.
DD: Like what else?
MR: We sometimes tie them to writing goals – you know, you have to write at least 10,000 words of your law review article by a certain date or else you have to give the other person or a charity some significant amount of money.
By the way – how did you work at Bloomberg given how much you like junk food?
DD: Well, you know, they say when you first start there you gain weight.
MR: Isn’t it called the Bloomberg 10?
DD: Exactly. That was probably the period in which I gained weight, but then I also had the most diet bets.
MR: What kind of junk food do you like?
DD: I like anything – literally anything. Candy is best. Any kind of candy.
MR: Do you like sour candy?
DD: No. If you asked me to eat one candy every day for the rest of my life it would be Tootsie Rolls.
MR: What!? And you don’t floss!? Do you get cavities a lot?
DD: No. I’ve had one or two.
MR: Wow. How does that work?
DD: I don’t know. What do you mean, “How does it work?”
MR: They say don’t eat sugar and floss.
DD: I have good teeth and I have good eyes. Literally my eyes have not changed since I was a freshman in college.
MR: Do you wear glasses?
DD: Only for distance – like driving at night. But that has been the same since I was 19. My solid teeth and consistent eyes are my two best features.
MR: Did you wear braces when you were younger?
DD: Yep.
MR: Was that traumatic back then?
DD: It was so traumatic – I cannot tell you. I got them maybe the end of seventh grade, and my mom knew I was going to get braces and did not tell me. I felt like I was strapped down there being tortured.
MR: Did you have to wear headgear?
DD: I did. Not during the day, just at night. I wore two headgears to get it over with faster.
MR: Was it painful?
DD: The thing that was painful was getting the braces adjusted. That was horrible – that was the worst.
MR: This is a very bizarre question – do you wear a retainer now?
DD: You know, I actually do. The reason is because I have mild sleep apnea.
MR: Do you grind your teeth at night?
DD: I didn’t know I did, but apparently I did. I don’t anymore – well I do – but the mouthguard protects them.
MR: Do you wear it every night? Are you pretty diligent about it?
DD: Yeah.
MR: Do you dream?
DD: Occasionally, but not that I remember much.
Find Yourself a City to Live In
MR: As someone who spends so much time thinking about cities, what are some of your favorite cities in the world other than New York?
DD: I’d say probably Paris and Tokyo. I really admire the way those two countries – France and Japan – resist the homogenization of modern culture. They just so fiercely – probably not successfully – seek to preserve their uniqueness. I find that struggle heroic in a weird way.
MR: I know you wrote a book about New York coming back after 9/11 – what will be the markers of New York coming back after the pandemic?
DD: I think there’s a couple. Until the fall we’re not going to know what the office work environment is really going to be like. It’s not going to be the same because most employers are going to offer some degree of flexibility. The numbers of people in these office districts are going to be lower, which is hard for the retailers and others who depend on those employers.
The other thing that is not back yet is tourism – I know a lot of New Yorkers think this is good, but I think it's bad. It's coming back, but it's not back. Hundreds of thousands of people in this city depend on tourism. The other thing that's not really back yet is culture. I’m the chair of The Shed, and we’ve been through a really difficult period.
MR: What’s the deal with The Shed?
DD: It’s an amazing institution. I think we can really reemerge from Covid as the paradigmatic post-pandemic cultural institution. We're incredibly flexible and adaptable. The Shed was the first performing arts institution to actually hold live events, which was great. We could do it because of the flexibility of our space.
We’ve been through this incredibly difficult period, but I think we're coming out of it stronger than we ever were. You asked about New York and how you'll know – I think you’ll see packed houses in the cultural institutions – that in many ways is the heart and soul of New York City and we need that back.
MR: We’re gonna try to help you out with that one.
DD: I appreciate that.