Bono — Elevation Partners & Facebook Stake

Bono co-founded Elevation Partners in 2004 and invested $86 million in Facebook in 2009 — a pre-IPO gamble that, at IPO in 2012, was worth $1.5 billion. That single bet dwarfs his entire music career, which earned an estimated $700 million over four decades, making it 2.1 times larger. He also bet on Yelp and Forbes Media, though Palm faltered. Forbes puts his net worth at $1.8 billion, making him the richest rock star alive — and richer than #5 Diddy's peak valuation by 80%.