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Kyle Wilkinson's mother was a fashionable eccentric. A model for Geoffrey Beene during the designer's 1960s heyday, "She ran around Greenwich Village and practiced séances," says Wilkinson. The only thing her bohemian worldview had no tolerance for were bankers. When Wilkinson entered Chase Bank's training program out of college, in 1985, he and his mother "didn't talk for months. What I was doing was anathema to everything she stood for."
Wall Street wasn't everything Wilkinson stood for, either. Over 20 years, he left to work on startups twice, only to return. By 2008, "I could see the whirlwind around me," he says. "I was the oldest guy on our desk, and I was very tired."
When he left banking for good, the fashion world was in a tailspin. According to consulting firm Bain & Co., nearly half of all luxury goods went unsold in the fourth quarter of 2008. Wilkinson saw an opportunity: "I remembered the theory of comparative advantage. This is one of those situations—designers can sell excess goods or last season's fashion, and consumers pay far less than in stores." He decided to start a flash sale website offering men's goods at discounts to a private online community. The model had already proven viable; online retailer Gilt Groupe claimed $170 million in revenue for 2009.
That year Wilkinson founded Urbanbloke with a "low- to mid-six-figure" investment. About half came from him, half from friends and family. His first vendor, Alara dress shirts, "liked that we were a startup and was willing to take a chance." Finding a warehouse that took vendor shipments, made quality-control checks, matched items with orders, and shipped them was an "early feather in the cap," he says. As of June, the site had 10,400 members and partnerships with 100-plus companies. Top sellers include Tom Ford sunglasses and BedStü accessories.
Urbanbloke hired a buyer in February, but Wilkinson's wife still helps select clothing while his son interns and models between semesters at Wesleyan. Although now a "garmento," Wilkinson says his facility with numbers is what will steer Urbanbloke into the black. "Math is creative," he says. "My vision of the world is not my mother's."
Approximate number of total transactions on the site as of mid-August: 1,000
Low end of the minimum monthly amount it takes to run Urbanbloke.com: $10,000
Responses to craigslist ad to take over the intern job Wilkinson's son held: 150
Price range for items (from Original Penguin hats to Joseph Abboud suits) on the site: $20-$375