Wired has a profile of Jason Calacanis of Weblogs, Inc. (and now AOL). It is … mildly entertaining, albeit in a bratty sort of way.
The main lesson worth walking away with is that contrarianism and stubornness can pay. When other people might have gone underground after their prior high-profile venture (Silicon Alley Reporter, in Calacanis’s case) failed publicly and noisily, and after the market he celebrated tanked, he came back, as abrasive as ever, and was able to create and sell his new company. Sure, Weblogs, Inc.’s sale price to AOL was three-quarters froth, but that doesn’t make the money any less spendable.