5) Two bubbles are one too many. Yahoo was one of the survivors of the bursting of the late-1990s Internet bubble. The company was weakened but emerged to remain one of the Web's leaders. Granted, the more recent real estate bubble had little to do with technology and the Internet. But Yang saw firsthand how widespread the destruction was from the Internet collapse. And there were loud warnings of a probable crisis in real estate values and the economy at the time that Microsoft made its offer for Yahoo. It's hindsight, of course, but a more cautious Yang would have been seen as a hero.