Peter Thiel

Peter Thiel placed $500,000 into Facebook in 2004 at a $5 million valuation, becoming the company's first outside investor and ultimately cashing out over $1 billion—a 2,000x return. His hallmark was contrarian conviction; while many dismissed social networks, Thiel saw the flywheel effect of network dominance. Compared to Andy Bechtolsheim's $100,000 Google check (which yielded 10,000x), Thiel's outcome had a lower multiplier but a deeper strategic bet: he secured 10% of Facebook ahead of any venture capital firm. Beyond Facebook, Thiel co-founded PayPal and backed Palantir, cementing a reputation for betting on outliers before mainstream validation.