Stanley Druckenmiller loves a big bet. Both as a money manager and as a philanthropist, Druckenmiller has built his career on taking big risks—and very often, reaping big rewards. As founder of Pittsburgh-based Duquesne Capital Management, Druckenmiller posted an average annual return of 30 percent without a single money-losing year.

While managing Duquesne, he also enjoyed a 10-year stint as manager of the Soros Funds. There, Druckenmiller developed his interest in philanthropy. George Soros, who had hired Druckenmiller to manage his money so he could focus on his own giving, matched employee giving 4:1. “I was highly, highly influenced by that,” recalls Druckenmiller, who also credits his wife, Fiona, and Paul Tudor Jones with motivating his philanthropy.

In 2009, The Chronicle of Philanthropy recognized the Druckenmillers as the most charitable couple in America. Most of their giving has been in education, poverty, environment, and health—and most of it has taken the form of big bets, including a $100 million grant for a neurological institute at New York University’s Langone Medical Center.

To reinforce his bets, Druckenmiller invests in leaders he trusts. Take for example Geoffrey Canada, who managed to interest Druckenmiller in his vision for the Harlem Children’s Zone (HCZ) at a time when Druckenmiller wasn’t sure if it would be possible to raise the money to fund the plan. Today, HCZ is one of the most well-known initiatives combating poverty in the US. But in that decision-making moment, it was not the idea so much as Canada who moved Druckenmiller to get behind the effort. For Druckenmiller, there are many times when he thinks he may get a “zero out of [his] investment,” but if he can win on just a few big bets and enrich the lives of lots of people, that’s “sheer joy.”