4. Microsoft Enters The Video Game Market

In 2001, Sony and Nintendo were the undisputable players in gaming consoles. Sony upgraded its original PlayStation to PS2 and Nintendo upgraded its 64 to Gamecube. It was being looked as a foolish move when Microsoft decided to make consoles considering it had just entered the hardware market. Though, Microsoft took a loss of $4 billion on the first console, today, with the XBOX 360, it has created a multi-billion dollar entertainment business.

3. Richard Johnson Mortgaged His House to Buy A Superbowl Ad

HotJobs, a job search engine was struggling in 1999. So, CEO Richard Johnson decided to mortgage his house and buy a $1.6 million Superbowl ad. He was trying to do what Apple does, except he was spending his personal cash. The gamble paid off when 2 years later Yahoo acquired it for half a billion dollars. He has since moved to North Carolina where he lives with his family and does philanthropies.