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The investment: Bono is a managing director and co-founder of the private equity firm Elevation Partners, a firm dedicated to large-scale investments in "media, entertainment and consumer-related businesses."
The firm made some solid investments early on, purchasing stakes in Yelp and Facebook, and turning a $300 million investment in video game creators BioWare and Pandemic Studios into more than $620 million when Electronic Arts purchased it from Elevation in 2007.
The dive: Their subsequent investments were less prescient, as the company reportedly sank around $460 million into Palm, and $264 million into Forbes Inc. Elevation faced huge losses on Palm until HP bought Palm in August 2010 -- giving Elevation a paltry $25 million return on its investment. In 2010, the website 24/7 Wall Street dubbed Bono "the worst investor in America." But he may have had the last laugh after all: Before Facebook went public, Elevation Partners' stake in Facebook increased by an astounding 400 percent after another investor sold his share, according to London's Daily Mail. And the sale of a majority stake of Forbes to a media company in 2014 likely netted him millions.