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NYC's Top VC Fred Wilson Is Rich . . . and Grumpy

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While USV was building its roster, Wilson was blogging every day—mostly about investing and technology—and becoming increasingly engaged with social media, which has made him beloved by the CEOs and founders of USV’s portfolio companies, who emphasize Wilson’s passion for Web 2.0 technology and his commitment to product development.

"Everybody reads his blog; he’s a celebrity, so I’m thinking he’s probably overhyped," Ted Livingston, the founder of Kik, a group-messaging application that got $8 million from USV and two other firms, recalled thinking before he met Wilson. "But he’s not. He uses the product, cares about the product, works with you on the product—whereas most investors just look at the numbers."

Though it’s USV partner Albert Wenger, not Wilson, who sits on the board of Foursquare, which USV helped fund,  co-founder Dennis Crowley says, "I get emails from Fred on the weekends or in the middle of the night. He’ll say, ‘At dinner, I was talking with my son about [Foursquare], and we thought of a great idea.’"

At least one CEO in USV’s portfolio thinks Wilson’s engagement will set the standard for venture capital going forward. "Guys like Fred will make the standard, prototypical VC endangered at some point," says Michael Yavonditte, the CEO of Hashable, a business networking service. "If you lack the desire to use these technologies over time, it’s going to be nearly impossible to compete with guys like Fred."

But Wilson’s passion doesn’t always get channeled in such positive ways. Sometimes, instead, there are tirades against California’s Internet titans. Facebook is "a photo-sharing site." Google hasn’t produced anything great since Gmail. Apple is "evil" because "they believe they know what is best for you and me." (In January 2009, Wilson announced that he was selling his shares in Apple, then trading at $91.36, because he didn’t believe Apple was being honest with investors about its CEO’s health. Twenty-seven months later, Apple’s stock was at $338.08.)

Watching Wilson attack these success stories can be a little like watching an emotional adolescent get angry because his older brother won’t acknowledge his opinions. At one point during the Web 2.0 Summit, while arguing that Facebook hadn’t invented anything original recently, Wilson choked up and looked like he was about to cry.

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