Former PayPal co-founder and CEO Peter Thiel has built a reputation as one of the most iconoclastic figures in Silicon Valley. A libertarian and futurist, Thiel invested $500,000 in Facebook in 2004 for a 10% percent stake in the company. Last year, Thiel announced a new initiative to pay 24 college-aged students $100,000 to skip college for two years and instead focus on developing business ideas in areas such as biotechnology, education and energy.
Facebook stake: $2.5 Billion