Jerry Yang

Loss this year: $11 billion.

Normally it is the founders who sell their companies who have the most regrets. The new guys come in, pile on the debt, and mess everything up. But lately shareholders are hopping mad at Yahoo.com co-founder Jerry Yang for not selling out to Microsoft (MSFT). The software giant pursued the Web portal for three months, raising its offer from $31 to $33 a share, a total value of some $45 billion. But the 40-year-old Yang held out for more. Then Microsoft gave up, the economy went south and took Yahoo's stock price right along with it. Microsoft CEO Steve Ballmer says he's uninterested now, even with Yahoo's share price having fallen by more than half. In mid-November, Yang announced that he was stepping down as CEO and returning to his job as "Chief Yahoo." His Loss this year: $11 billion.