Then, the unwinding hit. It didn't help that Thiel had a $6.5 million mansion in San Francisco and a $27 million oceanfront spread on Maui. He became more active in his hedge fund, going long as the market tanked, shorting stocks that subsequently rose. Ultimately, his hedge fund's assets were down from $8 billion to $350 million, a colossal loss signifying a rare failure from such a bright star in the technological landscape. That represents an almost 96% loss in three years. Those of us in an S&P index fund only suffered a 7% loss in that timeframe, and, by buying and holding through all the unwinding, are now up nearly 43% compared with 2007 (before the Great Recession).