The Entrepreneurs of the Decade: 2000 to 2009

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Nick Denton of Gawker Media

“I'd rather be wrong and thriving than right and dead,” the founder of Gawker Media wrote on his blog in July 2009. He was referring to a prediction he had made nine months earlier that, before the recession was over, media companies would experience a decline in advertising revenue of as much as 40 percent. So Denton promptly (and rather dispassionately) shut down several underperforming sites and trimmed his staff. The moves seem to have paid off, assuming Gawker's revenue closely tracks its surging Web traffic. But we're not adding Denton to this list because his business is doing well. We like him for those matter-of-fact, I-told-you-so blog posts and memos. Many, many entrepreneurs believe they can see farther down the road than the rest of us (and many of them can). It's fun to see one of them document what that feels like.