Urban Legends

An Internet image search for Greg Selkoe yields dozens of photos of the 32-year-old CEO clowning with celebu-friends, pouting, and making various hand gestures for the camera; in one snapshot, he clutches a Chihuahua while making a kissy face. The images display a fratty jackassery that does little to suggest the master’s degree from Harvard (in public policy), or the canny marketing strategy that’s making him rich. In Karmaloop’s downtown office, the couple’s two dogs roam free, their only responsibility being to pee on taped-down paper squares and not on the white backdrop in the fashion photography room. (Back at home, they have their own bathroom.) But the pets and the posturing are all part of the idea behind Karmaloop and the juvenile (or at least youth-oriented) fashion it sells. “We’re just having a lot of fun,” he says. “I had no idea that it’d get as big as it has.”

Selkoe will tell you that his background as a rich white kid is somewhat “soft,” to use the parlance. “Yeah, I used to break dance for money, like in first grade, on the streets of Nantucket,” he jokes. He grew up in Jamaica Plain, the son of renowned Alzheimer’s researcher Dennis J. Selkoe (once featured on the cover of this magazine) and Polly Selkoe, a Brookline town planner. He and Dina met as 14-year-olds at Brookline High. “Then I went to reform school for bad children,” he says, smiling. After turning things around, he went on to graduate from Rollins College in Florida, and got a suit-and-tie job as an urban planner at the Boston Redevelopment Authority (BRA)—a position that would become a surprising complement to his future rise as a streetwear mogul.

“As an urban planner, you have to know how cities work, what draws people to them, who is shaping them,” says Prataap Patrose, deputy director for urban design at the BRA, who remembers Selkoe as “always on the go.” Right now, he adds, youth culture is doing most of the shaping. “Greg understands the urban milieu very well.”

Selkoe’s long-standing love for urban culture—he wasn’t entirely kidding about the break dancing—was Karmaloop’s catalyst. (The name came from an erstwhile logo, which incorporated the Buddhist symbol for karma. “It kind of looked like a volleyball,” Selkoe says, “which was cool but impractical. And it had a loop, loop, loop, so we said Karmaloop.”) When he founded the company in 1999, as a side project while he was still at the BRA, he and Dina—then pursuing a dual degree at Harvard Law School and Tufts’ Fletcher School—were living with his parents in Jamaica Plain. He’d decided to quit the BRA to study public policy at Harvard’s Kennedy School, and thought he might as well focus on the store at the same time. Which he did, with $50,000 in stocks saved up from when he was a kid, support from Dina, and periodic small sums from his dad, who’s still an investor. “The Internet bubble had just burst, and most people I talked to said they wouldn’t touch e-retail with a 10-foot pole,” says Selkoe père. “But Greg knows how to do cool.” (“He’s been very supportive,” says Greg. “Obviously he doesn’t know anything about streetwear, but he knows about life and business, and it’s paying off for him.”)

At the beginning, the couple sold a limited inventory out of the elder Selkoes’s basement. To impress the labels they liked, whose specialty lines they wanted to sell—particularly in the case of major players like Puma, Reebok, and Adidas—they focused on small but intense brand representation. “The Internet wasn’t the newest, craziest thing,” says Selkoe. “So I developed a new paradigm. I said, ‘Look, we’re not going to be your biggest customer right now, but we’re going to represent your brand better than anyone else, we’re going to represent your brand online, and yeah, we might not sell that much at first, but we’re going to basically be a free online magazine ad for your clothes.” The corporate sneakerheads bought it, although revenue was, unsurprisingly, slow in coming at first. “There’d be three or four orders a day, and Dina and I would package them up and drop them off in the mail on our way to work or school,” he says. “It was sometimes a mystery to me how people even found our site.” Yet such are the vagaries of his chosen market that by not doing anything to baldly lure customers, he was almost guaranteed to bring them in.