DonorsChoose.org has since raised $36 million for 2.2 million students and drawn luminaries like Stephen Colbert to its board.
Regrets: Picking the name Donors-Choose: "It works as a literal indication of how our website works, but it doesn't stick in people's brains."
Missed career: Best took the NYPD entrance exam while a senior at Yale but opted for teaching instead. The NYPD was still holding a spot for him until a few years ago.
NEXT: Gina Bianchini