8. eBay Buys Skype

Sale Price: $2.6 billion
Year: 2005

eBay was ahead of the game when it acquired Skype in 2005 for a surprising $2.6 billion. By 2009, the VoIP and video calling service was making appearances on Oprah and Who Wants to be a Millionaire. That same year, eBay sold a majority stake in the company to a an investment consortium at a profit. In 2011, Skype was sold again to Microsoft for a whopping $8.5 billion.