Year sold: 2008

Clek Media brokered a deal that few people believed was real: The URL was purchased by a company called Fund.com in an all-cash deal in 2008.

After the flashy sale, Fund.com ran into a lot of trouble. It had to declare most of its financials unreliable in 2009 and continuously failed to file reports. The man behind it — Jason Galanis — reportedly has an interesting history. If you go to the site now, it won't load.