“That’s part of my job, learning how to be comfortable in rooms where I am, by far, the person with the lowest net worth.”
He is a writer at New York magazine where he covers business and technology. Before that, he worked at The New York Times, where he covered Wall Street and the culture of finance. He has written for GQ, Esquire, and SPIN.
In 2014, Kevin published Young Money, Inside the Hidden World of Wall Street’s Post-Crash Recruits which follows eight young Wall Street bankers in the first years of their careers. It debuted on the New York Times bestseller list. His first book, published in 2009, was The Unlikely Discipline, “a memoir of the semester I spent undercover at Jerry Falwell’s ultra-evangelical Liberty University.”
Kevin talks about his upbringing as a Quaker, encountering persons with wealth for the first time in boarding school, and going on to become a journalist covering Wall Street.
I grew up in Oberlin, Ohio, a tiny college town in the Rust Belt of northern Ohio. My father is a small town lawyer; my mom was an administrator at Oberlin College. It’s a town of about 5,000 people. Very small town. It was an interesting time to grow up there because it was this little, liberal oasis in the middle of one of the most conservative parts of Ohio.
In my time, there was not a lot of wealth, and there was certainly not ostentatious wealth. I remember gossiping about when somebody’s dad bought a Lexus. That was the talk of the town for weeks. It was not something that was done. I’m sure plenty of people had money. Oberlin College was for kids with rich parents, but the town itself is still sort of modest and conspicuously so.
My family is Quaker, so we had an especially interesting relationship to money. One of the core tenants of Quakerism is simplicity. It doesn’t mean that it’s Amish, but certainly there was a value growing up that money was not the be-all, end-all. There was not a whole lot of emphasis placed on driving me or my brother into high-paid industries. I didn’t feel a ton of pressure to make money.
When I was like twelve, I did go through a little Alex P. Keaton phase. I was convinced that I was going to be a real estate investor. I think it was because I read some book about how to get rich. My family sort of chuckled. I was wearing, you know, sweater vests. It was not a very long-lived phase, maybe a couple months, before I realized that actually it’d be an incredibly boring thing to do.
I think other than that, there was never a time where I thought I was going to become a capitalist or make a ton of money. I think actually I would have been scared to think that because, in my family, it would almost be worse to be extraordinarily wealthy than to be poor. At least there was some nobility in being a poor artist. I would almost be embarrassed to come home in a fancy suit and be driving a Mercedes. It would not endear me to anyone that I grew up around.
But when I was sixteen, that changed, because I went to boarding school. It was a Quaker boarding school, but it was outside Philadelphia, and a lot of the people there were wealthy. Some of the wealthy Philadelphia families would send their kids to this private school because it was better than the public schools. So there was a Quaker backdrop to it, but my roommate there, his dad was like the North American President of Ikea. Just unfathomably wealthy. Much more money than I’d ever been around before. Kids had Lexus; they got them for their sixteenth birthday. It was not uncommon for people to use summer as a verb or talk about Martha’s Vineyard. That was never something that I’d been around.
What was your initial reaction to that?
It was shocking. But I didn’t want to act shocked. I was trying so hard to fit in. It took a lot of work for me to be able to feel like I fit in. People would ask me where I spent my summers, and I would say, Oh, I go up to my family’s beach house in Michigan. Which was true, my grandparents had a place in Michigan, but it was not the kind of beach house that everyone there was talking about.
I also remember feeling like I needed to get new clothes because my clothes weren’t designer. And I needed to figure out new ways of spending free time. I just didn’t quite know what I was doing. It wasn’t so much just the money, it was the money plus the geography. Being from the Midwest and feeling like this is a much different culture than I was used to, and also just being in a new place away from my family for the first time — it was all disorienting on multiple levels.
Did you ever feel resentful of their wealth?
I was certainly jealous. I mean, I was jealous of the kids who had fancy cars, jealous of the kids whose parents took them away. But I became good friends with a number of these kids, so I would get to go to their beach houses. I would tag along with them when they went to their parents’ country club for dinner. So I got to see some of this stuff and benefit from it. But I always felt a little bit like an outsider looking in, because I was getting a scholarship. It was clear that I was not nearly as well off as a lot of the people at my school.
But I think I felt much more comfortable [when I got to] Brown because I had spent a couple years being sort of primed for that and learning how to pass in socioeconomic class situations, trying to figure out how to be comfortable with what money I had and what status I had.
While working on his book, Young Money, about eight early-career Wall Street bankers, Kevin decided to pursue the“one question that proved stubbornly elusive: what happened to Wall Streeters as they climbed the ladder to adulthood?”So he crashed the party of a Wall Street “secret society”and reported on it in the book. He writes, “I hadn’t counted on getting into the Kappa Beta Phi dinner, and now that I had gotten past security, I wasn’t sure quite what to do. I wanted to avoid rousing suspicion, and I knew that talking to people would get me outed in short order.”
(Read an excerpt from the book his New York magazine article: “Inside the exclusive annual dinner of Kappa Beta Phi” here.
I am wondering how much of 16-year-old Kevin Roose walked into that secret society that night.
I think my entire life up to that point had prepared me to be extraordinarily skeptical of people with wealth. At the time that I joined that party, I’d been working at New York Times covering Wall Street. That’s a job that puts you in contact with many of the wealthiest people in the world. I was of the opinion that these people were not that special; they were smart and they were well-educated, and they were good at their jobs, but they weren’t any smarter than my parents or the parents of my friends growing up. They had achieved enormous financial success basically by luck.
And [what I saw at the party] was really affirming, in a way. I mean, it was terrible, obviously, to see these people acting extraordinarily badly, but it confirmed my priors to see that they were just these immature, sort of grotesque people who were no more sophisticated under the hood than any of the people that I knew. It sort of convinced me of that. If I needed anymore proof, that was the proof.
Have you found that it’s true that, as F. Scott Fitzgerald said, the rich are different from you and me?
It’s a language, right? They speak a different social language than we do, and I think I’ve learned to speak that. That’s part of my job, learning how to be comfortable in rooms where I am, by far, the person with the lowest net worth. And to be able to pass in that class. Journalism is really interesting in that regard. You eventually come to sort of be social equals with the people you cover, even if your situations are completely different. I have people who are much richer than me who call me for advice or who are my friends now, and I don’t think the economics come between us as much because I have this sort of weird role as an insider in their world.
Making money is a very specific skill. This stuff is not easy, and I probably couldn’t do it. But it’s a trade like any other. You study it; you get good at it. It’s not like you have to be born with some acumen that you can’t replicate any other way, that carries you to success. You study it and you apprentice with people who are really good at it, and eventually you start doing it yourself. A lot of it comes down to just being willing to put in the effort. This is something that’s been confirmed to me subsequently by the reporting I’ve done on tech billionaires, too. These people are lionized, and I think sometimes unfairly attributed. Certain people imbue to them all these characteristics that they don’t have in any great quantity.
I know a lot of people who make a lot more money than I do but are less successful than I am, if that makes sense. And that’s the screwed up thing about inequality and relative wealth. The richest, most successful writer you can think of is probably like, someone like J.K. Rowling or Stephen King whose books have had unfathomable success. And yet they are probably still making about as much money as a mid-level, relatively-good-at-his-job, second stringer hedge fund manager. Or tech CEO. It is just such an unequal playing field. And that’s totally crazy. You can muddle along in an industry like finance or tech and still become generationally wealthy. And that doesn’t bother me… I mean. Well, it does bother me. I wish we put a premium on the arts and creative expression. Something’s off there.
I feel like one of the things that is most unfair about income inequality is the real disparate opportunities it gives to people coming out of college. I talked to one magazine editor just yesterday who was saying, I don’t know how our interns do it. We pay them $30,000 a year. They have to live in the Bay Area. He said, they must all be from wealthy families. And that’s true. There’s an assumption, at least tacitly understood by my friends who are aspiring writers, that they need to have a fallback plan. They need to go to law school; they need to work for money.
Something weird happened to me economically when I was 19 — I got a book deal. And like this big pile of money dropped in my lap. It wasn’t millions of dollars. Itwas enough that I felt like I could help my parents pay for the rest of my college. But it wasn’t a life-changing amount; it was more money than I’d ever expected to make at such a young age, and it was very stressful. You know? My first instinct was to put it away and just pretend it didn’t exist, but then I realized I should probably use some of this to move to New York and try my best at starting a journalism career, so that’s what I did.
The way that you are able to become an artist or an actor or a photographer is that you don’t need the money. If your parents would help you well into your twenties, then you could take that gamble. I was very lucky. I didn’t have that kind of a [family] safety net, yet I was still able to move to New York, not make much money right away, but was able to support myself. It bought me time. It wasn’t a windfall, more like a wind drop, but it bought me time and it bought me risk-tolerance.
I wouldn’t trade my upbringing for anything. I think it gave me a wonderful foundation. I never want to lose that perspective. I see a lot of my friends spending so much time around people of means that it sort of becomes their worldview. I really don’t want that to happen to me.
I’ve talked to a lot of [wealthy people] in my career, and they don’t seem happier than the people that I know who are not wealthy. In some ways, what it buys you is flexibility. It buys you never having to worry. You don’t stay up at night wondering if you’re going to be able to pay next month’s rent. But you have this other host of problems that pop up. I think money is not the sort of cure-all that people would like it to be.
When you have children, what do you want to teach them about money?
I think that ultimately, I don’t want them to be scared of money. There are some elements of the way I was raised that I think might have been too cynical. I think ultimately, I would rather give them the education that I had and the experience that I had than have them grow up as a child of privilege and never know the value of a dollar.
But it’ll be interesting. A lot will depend on where I am in my life at that point. In some ways, environmental forces are more powerful than the origin story, and that’s what I’m worried about. If I raise kids in an area where there is a lot of money, even if I don’t have a lot of money, if they’re around that, if I’m living in a big city and there’s a lot of money in it, my concern is that they’ll pick that up from the environment no matter what I tell them. I hope that I will be able to shield my kids from that in some ways, and raise them with the values that I grew up with.
Well, we’ll see. (Laughs)
See Kevin’s appearance on The Daily Show with Jon Stewart here.