In 2006, Wales was courting Marc Bodnick, a cofounder of Silicon Valley private-equity firm Elevation Partners, in an effort to find a way to profit from Wikipedia, despite its nonprofit status and volunteer contributors. Bodnick and an assistant had traveled to St. Petersburg, Fla., where Wikimedia was then based. The talks went nowhere, but Wales, his wife, Bodnick, and Bodnick's assistant had a $1,300 meal at one of the city's finest restaurants. ($600 of the bill was spent on wine.)

At that point, the Wikimedia Foundation had confiscated Wales's corporate card, so he paid for the meal himself. But he then sought to have it reimbursed by Wikia. Michael Davis, Wikia's chief operating officer, became enraged and reported the expense to Jeremy Levine, a Wikia board member and partner at Bessemer Venture Partners, which had invested $4 million into the company only a month before.

Levine then told Wales he was fired as CEO, and found Penchina, who had already made a fortune at eBay. Wales must hate that: Every time he sees Penchina, he must ask himself, "Why is this guy rich and I'm not?" Penchina, meanwhile, must be asking why Wikia is still paying Wales a salary.