Nick Denton Smarter, Richer Than You

Gawker Media chieftain Nick Denton is making a whole lotta money off his links-and-jokes empire. Shylock Blogging pegs it at $52 million a year, while Greg Allen puts it at closer to $20 million. Whatever. The guy is rich, and he's making enough that he'd rather have the cash flow than the price he'd get from whatever sure-to-be-insane valuation Gawker would fetch in a sale.

Denton is a seriously smart individual, and I don't just say that because Gawker is his third successful startup, or because he once tried to hire me, or because his brainpan is so very, very capacious. The guy is constantly thinking two steps ahead of his competition. He's a master of the low-risk, high-reward strategy: Start a site with a couple of freelancers; if it catches fire, keep it; if it fizzles, fold it fast. His latest launch, Jezebel, is already drawing as many visitors as many of its established competitors, thanks in large part to an extremely canny publicity stunt.

Unlike a lot of entrepreneurs, Denton's not a huckster or a press whore. He's too clever to share his best ideas with the world, but get him going and you'll realize that no one understands blogging better. He has an intuitive feel for the values his blogs should embody—informed but outsider; angry but not bitter—and a keen sensitivity to the changing tastes of readers. It's not that Denton never makes a false step; he does. But he's a little like the velociraptors in Jurassic Park, hurling themselves against the electrified fence, intent on a goal, always learning. Also, evil.