What it’s Like to Be (Very) Rich in NYC

Anne Kadet's interview of me in which I disclose more than I intended.

Back in early September when summer seemed endless and the election wasn't yet casting such an enormous shadow,

Anne Kadet

published an interview with me in her unique, madcap, and wonderful

CAFÉ ANNE

Substack.

In the excerpt below from Anne’s interview, my answer, although still quite vague, made me feel exposed. This is something I plan to explore in a future post.

“So this is the worst question I'm going to ask, because it's the most awkward...

Ask away, and I'll tell you however I'm comfortable responding.

Ok...HOW RICH ARE YOU?!?!?!

I was thinking you might ask and I would be hesitant to just blurt out a number.

The way I would say it is, I've built up enough wealth that I don't have to work, and can pretty much do what I want within reason. I would say we're within the top 0.1%, if that gives you a sense.”

With Anne’s gracious permission, below is her full interview of me along with pictures she took while visiting with me at my home as well as pictures she took at a gathering the first time we met.

Anne’s interview starts here.

David Roberts at his writing desk

David Roberts first came on my radar last fall when he bought a classified ad in

CAFÉ ANNE

to promote his own newsletter “Sparks From Culture,” which at the time covered things like politics and movie recommendations.

I heard from him again a month later. I’d just co-hosted a little potluck party for Substack writers and readers in my Brooklyn apartment, and David offered to co-host another party with us at his place after the holidays.

Sounds like fun! I didn’t think much about it until he sent the proposed invite, which included his address.

Hmmm! Being a real New Yorker, which means super nosy about real estate, I went straight to Google Maps. Not only did David live on Fifth Avenue, he lived across the street from Central Park. And not just across the street from Central Park, but directly facing the Metropolitan Museum of Art. On StreetEasy, I learned his address is “one of the original great luxury apartments on Fifth Avenue.” Units typically sell for $20 million. Cash only!

It was then that I knew that this wasn’t going to be party. It was going to be a par-tay! David said he’d have it catered, complete with waiters and an open bar.

Haha. You can imagine how bonkers it felt to be co-hosting an event at such a swanky address. Here are a couple pics from the party, in January:

Me, fist-bumping Substack transportation writer Sam Sklar

The spread!

It was a fun night. And not just because it was oh-so-classy. David turned out to be a real sweetheart—kind and down-to-earth, in a very Upper-East-Side way.

I got to know him a little better in May when he invited me and a few other writers to a little dinner party. But of course I wanted to know more. What’s it like to be super rich in NYC? I needed an excuse to ask him a whole bunch of prying questions.

So I was very pleased when he agreed to an interview, which took place last Tuesday afternoon in his sitting room, which is roughly four times the size of my entire apartment. I had fun chatting with David, and hope you enjoy the read.

Please note that the following Q&A was drastically condensed from a two-hour convo, and edited for clarity.

I texted you on my way over to warn that you’d better be feeling chatty, because I had three pages of questions for you! Why are folks so curious about rich people?

Part of it is that wealthy people don't like to talk about their wealth. And if they do, it's usually very performative—not something that is relatable.

Also, if you think about how wealthy people are portrayed on television, it's Succession or Billions. It might as well be Lord of the Rings, right? It's fantasy.

I think people are curious because they don't really get an authentic look inside.

So this is the worst question I'm going to ask, because it's the most awkward...

Ask away, and I'll tell you however I'm comfortable responding.

Ok...HOW RICH ARE YOU?!?!?!

I was thinking you might ask and I would be hesitant to just blurt out a number.

The way I would say it is, I've built up enough wealth that I don't have to work, and can pretty much do what I want within reason. I would say we're within the top 0.1%, if that gives you a sense.

You're retired from a long career in finance and have a delightful wife, Debbie, plus three grown kids who are doing great. And you're only 62. So what's your typical day?

I get up really early, around 5:30, because I like the morning—just to be able to read. I read a lot of Substacks. And then today, I had a breakfast with somebody I knew from a not-for-profit. Then I came home and took a nap because I was tired.

I love a morning nap!

Then I went to my standing physical therapy appointment. Nothing is bothering me now, it's a maintenance thing. And I got to walk back-and-forth through Central Park. I came home, had lunch, did some reading and tried not to think about the post I haven't written. And then you! So that's a pretty typical day for me.

I also have responsibility for—I manage our money. I look over what the kids are doing, just to make sure they're being treated the right way by our bank. I have a father who is 87, so he looks to me to help manage some transactions. So I have those sorts of things to do.

What will you do this evening?

I'm tempted, because it's so nice out, to go for a run. And I'll probably do some writing. And when Debbie comes home, we'll probably eat dinner and watch TV together.

Do you watch Succession and Billions?

We watched all of Succession. I thought it was brilliant. Right now we are watching Industry, which is not so brilliant.

Why do you live in New York?

It just feels like home. I grew up here. Debbie grew up here. Our entire family is here. We're very rooted in New York.

David walking the mean streets of NYC with his wife Debbie and, from left: son Michael, son Andrew and daughter Lauren.

How do you feel about the city?

I was born in '62. In the late 70s and early 80s, I didn't realize how rough it was. I knew, "Don't go to Central Park," particularly at night. You know, there were definitely boundaries. But I stayed pretty close to the Upper East Side.

I haven't really seen the New York Post version of the city. The major negative change that I've seen are the bicyclists who don't always obey traffic lights.

That's me!

Okay, and that's me—yelling at you in my mind or giving you a stern look.

Not the finger, but a stern look!

A steely-eyed glare!

But yeah, this is a nice neighborhood. You go to the park, everyone's happy. It feels really good. My younger son loves New York and explores all over. I'm very much a homebody. I don't really take advantage of all the different neighborhoods and the diversity.

You're not alone. There are people living in Brooklyn who haven't been to Manhattan in 40 years.

Yeah, but I don't wear it as a badge of honor. I'm a little bit embarrassed about it.

Any idea how much you spend a year as a New York City resident?

I know precisely! I guess that's a number I'm a little loathe to reveal.

Maintenance and the costs of our houses [in Manhattan and East Hampton]—that takes up a big chunk of the budget. We do give away a fair amount of money, and we have a lot of personal services. We have a full-time housekeeper. We have fitness people we go to. If we are going on a car trip, we will sometimes use a driver. We don't have a full-time driver, but it adds up.

It's a lot of money. It's kind of a trap that you fall into if you can afford pretty much whatever you want, if you think about everyday things or services. If we want to go to a restaurant, we don't think about what that is going to cost. At least, I don't. Debbie grew up differently than I, so she's more price conscious. She doesn't want to know what certain things cost, like hotels. I have to keep that hidden from her.

Do you go on super fancy trips or drive fancy cars?

When we go away, I do splurge on hotels. I like to be in a nice place. Our favorite hotel is the Aman chain, and those rooms are really expensive. They cost like $4,000 a night.

We don't have fancy cars. We have whatever the entry-level Tesla is, that my wife actually doesn't like. And I drive a Mini Cooper, which I love.

That's a good city car!

It's great for someone who's a bad driver, because it's really hard to dent somebody else in a parking lot, because it's so small.

What's the most foolish thing you've splurged on?

When the Barclays Center opened, I decided it would be really good to get great seats to the Nets. We were in the second row, so you could really see the action. It was fun when we went, but we really had no interest in going to every game, and I'd made a two-year commitment. So that was an exorbitant expenditure. The second season, I gave the entire set of tickets away to a charter school network.

The median household income in New York City is $74,000. If you had to live on $74,000 a year, would you still live here?

I don't think I could. Because New York, to me, means a certain way of living.

What percentage of your spending every year is giving?

It's about 25%

Are you a big tipper?

Yes, I'm a big tipper because I just feel like it's the right thing to do. Even if the service is bad. Because maybe I'll be the only person to leave this person a tip.

What percent do you tip when you eat out?

It depends on the check size. I don't want to tip less than $10 a person. And I basically tip at least 20%, usually more, even if it's a fairly expensive meal.

Do you give to panhandlers?

No, because I don't know where the money is going. And I try to be really thoughtful. We tend to get really involved in the organizations that we support, so we have a pretty good idea of what the impact is.

Occasionally I'll give money when I'll read about something in the newspaper. About ten years ago, I read an article about a quirk in the pension laws where someone's husband died at a very early age. Because of the quirk, she was denied her husband's pension payout. It made me really upset. So I was able to get in touch with her, anonymously—I still don't think she knows who I am. And I've been paying her pension every month, and that gives me a lot of satisfaction. I've done something similar to that a few times.

What is something you're glad that you don't have to do because you have a lot of money?

Well, let's say I have a very limited spectrum of household chores. Here in the New York apartment, it's pretty much restricted to taking out the garbage. That's pretty much my beat.

I love that you've reserved just that one chore.

I haven't reserved it. It's been given. My wife runs all the households. She basically told me that the garbage is my domain, and it's very important that I be proactive. If she has to say, "David, did you take the garbage out?” I have failed.

And then in East Hampton, not only do I have the garbage, she's also told me it's my job to make sure that there are paper towels in the paper towel holders.

So that's a long way of saying that I don't do a lot of household chores. And it's a real privilege that I don't have to spend my time doing that, because I wouldn't be good at it, and wouldn't enjoy it.

David does walk his dog, Sophie.

You wrote in your newsletter that you were once part of a group of wealthy people who met monthly to discuss "having more money than is necessary." Can you tell me about that?

It was a series of groups over ten years, people discussing what was going on in their life. It gave me a lot of insight into how wealthy people thought.

One of my takeaways is that people become wealthy for a whole variety of reasons. They could have inherited money, been in the right place at the right time or just been really good at a particular thing.

But if anything, I thought being wealthy can make people worse at other parts of their lives, because they spent so much time on the business side of things. I think the incidence of divorce was higher. I think the incidence of strained relationships with children was higher.

If I compare them with people that I've met at Substack, a million times over, I'd rather be with the Substack people. Because they have, from my point of view, much more balanced, self-aware lives.

There are, of course, exceptions. But a lot of the wealthy people I've met generally don't have much introspection or broader cultural interest. Many of them say, "I don't read. I don't have time to read books." If they read, they'll read whatever the correct biography is to read, or some titan's manifesto. Some of them still cite Atlas Shruggedas their favorite book.

Earlier today, I got my hair cut, and I told my hairdresser, "I'm going to talk to a very rich person about what it's like to live in New York City." And my hairdresser said, "If the guy says he's feeling sorry for himself, that his life is terrible, I don't think I would like him. But if he said, 'Everything's awesome, I love my life!' I don't think I'd like that either. I'm not sure what he could say that would make me like him!'"

Well, I certainly wouldn't fall into the first category of feeling sorry for myself. And as far as everything being awesome, you adapt to your surroundings, right? You get used to certain things. No matter how wealthy you are, you can get very frustrated with things. You can still be frustrated with yourself.

Like when you write, your wealth doesn't matter. You can still be really frustrated that you're stuck or don't like the sentence you just wrote. Or I love to play tennis and still get really upset at myself for making a stupid shot.

So I guess I would say that money doesn't take away all the natural human frustrations or grief. When someone close passes away, your grief is not going to necessarily be different.

Is hating the rich any different from prejudice targeting any other group of people?

It's understandable. First off, going back to the portrayal of rich people, it's not very flattering, okay? I was trying to think of a movie or television show or book that showed rich people in a really flattering light. The best I could come up with—and I did love the show—was Downton Abbey. Lord Grantham is a nice guy. He cares!

Second, it’s true, from my experience, that if you're wealthy and you're not introspective or self-aware, you have an unfortunate tendency to feel that you deserve to be wealthy, that it's because of your merit.

It's the Protestant work ethic, right? That still resonates here in the United States. And there's also a vestige of, if you're not wealthy, well, maybe you didn't work hard enough. I think a lot of wealthy people comfort themselves with that.

One thing I know for sure, from having been a NYC journalist for 25 years, is that just about everyone here is working really hard. The rich people are working really hard, and so are the poor people! I also know that a lot of poor people think that the rich people aren't working hard.  

I would imagine, if I were working in a physically demanding job, I might not give credit to someone who is sitting at a desk moving money around.

Do you think people can tell that you're wealthy?

I think so. I don't try to portray that, but I maybe have a certain way of speaking, perhaps an air of some confidence.

I also think it's a responsibility to be polite to everyone, but also not to think that just because I'm being polite to someone who's helping me, that all of a sudden that makes me a great person. And some people do think that, you know.

Were you taught to have a lot of respect for others?

I think that was part of it, although my parents were certainly not perfect models. But I got married really young, so if I exhibited bad behavior, I heard about it. Debbie was really good. And my kids, oh my goodness. If I was brusque with a waiter, they would get so angry at me.

You wrote that your family has been rich for several generations. How is that different from having made your own fortune?

I think it is very different, because although I did very well with what I was given, I also wouldn't have had that opportunity. Not only the money to start out with, but the connections and the social capital. The first job that I got was through my uncle, and that led me to the job [at Angelo Gordon] where I spent the longest part of my career.

And now you're in such a great situation, right? You've got a lot of money, you don't have a lot of responsibilities, and you're healthy. Do you see yourself just continuing what you're doing?

Substack's a new thing for me, and writing is a new thing. I'm interested to see where that takes me.

How has your newsletter evolved?

At first, I had no idea what it was. I just sent it out to 50 people, and I'd write about whatever struck me. It wasn't until November last year when I wrote about My Personal Myth that I started to risk writing about things from the point of view of a wealthy person—because I realized that no one else was. I decided to keep the name. Although a fellow Substack writer has suggested the name, "I'm Rich—Don't Hate Me."

That's a great name!

She said it as a joke.

Any insights you've gotten from reader comments on your newsletter?

Just hearing different people's stories, definitely. I think I've taken a much more critical view of capitalism. I see much more clearly some of the defects that can be reformed.

But I also sort of have an insider's point of view, so I see people making good general points, but then coming up with solutions that I know won't work or won't be as effective as they think.

My last question is, what would you like people to say at your funeral?

I would hope that they would say I was a good son, husband, brother, father, grandfather. That I helped people, that I was a person of good character and a good role model.

So let's say right after I leave, you keel over, and your funeral is this weekend. Is that what people would say?

Well, my grandson is only 19 months, so he might not say that. But yes, I think most people would.

So you must be happy!

Yeah, most of the time. But when you say I must be happy, the first thing that comes to my mind is, "My goodness, am I complacent?"