Glenn Kelman

In 1996, after earning an English degree at Berkeley, he gave up on being a novelist and co-founded Plumtree Software, which got acquired for $200 million in 2005. Newly wealthy, Kelman quit and turned to caring for his older brother, who was an alcoholic. Kelman, inspired, decided to become a doctor himself. He took the MCAT and was accepted at the University of Washington School of Medicine. But hi identity crisis was exacerbated when a venture-capital firm backing Redfin asked Kelman if he would want to be its CEO. When Kelman joined Redfin, it was a small start-up best known for its pioneering use of online maps for home listings. Kelman was obsessed with the idea of making Redfin the world’s first fully automated online brokerage.