Q: Do you find it ironic that Gen Xers—the same people who cried “Die, yuppie scum!”—have since become what they hated most?
A: Well, when I was making a living playing punk-rock music for a bunch of years in my twenties, they knew I was the guy in the band with the college degree and that I was looking around to do other things too. So they called me the yuppie. My response was, “Why, because I’m young and I live in the city?”

Q: If there’s nothing inherently wrong with having ambition, why does the term yuppie have such a bad rep?
A: Because at the time it was coined, it meant more like characters who aspired to be Gordon Gekko in Wall Street. But the weird thing is, a lot of my clients like to be successful, but they wouldn’t sacrifice any kind of integrity just to be successful. I think if you do anything purely for money or comfort, you’re doomed to fail.

Q: Some say new yuppies consume just as much but aren’t as conspicuous. Do you agree?
A: Yes, yuppies in this day and age are much more crafty. I’m conscious of which frequent-flier programs give the most back so I can travel in comfort without paying the full premium. We love getting one over the system, whereas in the eighties, the stereotype was the guy who said he didn’t fly coach because he didn’t have to, and he was proud to pay $6,000 for a plane ticket.

Q: What do you think of these guys who covet status through nice cars, clothes, and apartments but refuse to admit they’re yuppies?
A: That sort of sounds like me, I guess. I don’t really make an effort to dress up, but in a way, it’s kind of a reverse flaunting of the wealth. You’re making high six figures and owning property and doing all these things associated with success, but it’s flaunting of the wealth in an inverse manner by saying “Fuck it, I can go to work in cargo pants and a dirty shirt that smells like cat piss.” I was on a flight once in business class and the stewardess said, “You have profanity on your shirt.” I didn’t even think about it, but I was wearing a hip-hop shirt that said FUCK ALL Y’ALL.

Q: Is there anything really so bad about being a yuppie today?
A: I guess where you draw the line is whether it’s obnoxious or not. If you earn your success and don’t fuck anyone over to do it . . . I think that’s the main problem with the term yuppie. It conveys an image of people who screwed people over and robbed them. It connotes people more like from Enron than anyone who owns their own business.

Q: Would you consider yourself a yuppie?
A: In terms of someone who was young, urban, and professional, I wouldn’t deny it. I was always striving for success and working hard toward it. But if you mean yuppie in the sense that I’m an eighties stereotype of the greedy, fuck-over-your-friends-and-family-and-clean-out-Grandma’s-pension-funds-to-get-rich, then no. No way.