Greg Gretsch of Sigma Partners has reason to feel confident about his future as a venture capitalist. He backed the storage company EqualLogic, which sold to Dell in 2008 for a tidy $1.4 billion in cash. He led an investment in the Web services management company TalkingBlocks, which raised $9.5 million from VCs and sold to HP. (Details weren’t disclosed but Gretsch says it was a 2x for Sigma).
Gretsch has also seen some nice exits from angel investments made long ago. The audio player company Slim Devices, founded in 2000, was one of those deals. It raised $5 million and sold to Logitech for $23 million in 2006. Gretsch was also an early backer of Postini, which raised $26.45 beginning in 1999. It sold to Google for $625 million in 2007.
Even still, Gretsch says that as he enters his 10th year in the business, he’s worried about a tipping point. To wit, Gretsch doesn’t think that the longer you’re a VC, the more skilled you become in picking winners. Instead, he theorizes that if you’re a VC for more than 10 years, you’re likely to grow worse at your job over time.