Fred Wilson and his partners have turned Union Square Ventures’ Web site into a controversial blog about entrepreneurialism that hits both the lofty (social impact, reputation management) and the gritty (deal size, board strategy, due diligence). As a result, Wilson has become an irreplaceable resource and debate starter. “This is an industry that’s been very secretive forever,” says the early-stage VC veteran. “When you change the way a business works, a lot of people take notice. We’re having very public conversations.” And very public success: The firm’s portfolio swells with hot startups, including Twitter, Boxee, Etsy, and Zynga. The strategy is not without risk. When Wilson, 48, shared his opinion that Foursquare could be as powerful as Facebook or Twitter, “it woke up a lot of people. The financing got very competitive.” But Union Square won the day and the deal. “It validated us with their team, that we were willing to go public with our belief.”
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