7. Rupert Murdoch’s MySpace misfire
Rupert Murdoch came a cropper in 2005 when his company parted with a hefty $580 million to gain MySpace which, as you may recall, was the hottest social media site at that time. He wanted to make some money on internet advertising by using MySpace to drive traffic to its newspaper sites. Yes, it seemed like a sure bet, but Facebook happened.
Facebook thrived in popularity and MySpace began losing users in their droves. MySpace was eventually offloaded by News Corp in 2011 for just $35 million.