Sale price: $580 million
In 2005, as Myspace was just starting to lose its mojo to Facebook and was reduced to the Web's largest depository of pre-teen poetry and glittery unicorn GIFs, it found a savior. News Corp ( NWS) -- led by no less an Ashton-like hipster as Rupert Murdoch -- acquired Myspace and its parent company Intermix Media for $580 million. Things looked good for a while, and until 2008 Myspace held on to its place as the top social networking platform in the world. Then Facebook finally blew past it in Web traffic. Murdoch reportedly grew increasingly frustrated that the site failed to meet revenue projections and that it never materialized as an entertainment hub. Worst of all, it was adding little or no value in pushing Fox-produced content. Massive layoffs began in 2009 and continued until the company was sold in June of this year to Specific Media (who counts among its owners the far more Ashton-like Justin Timberlake) for nearly $35 million.