Herb Chambers

Herb Chambers dominates the Massachusetts auto sales market, with $2.5 billion in revenues per year selling Hondas, Chevys, Cadillacs and Bentleys. Chambers grew up in Boston's working-class Dorchester neighborhood, where he got his first job as a cart collector at the local supermarket. He later dropped out of high school during his senior year and joined the U.S. Navy. After returning, he borrowed $500 from his mother to start his first company, a copy distributor, which he sold for $80 million in 1983. Chambers then stumbled into the car sales business, purchasing a Cadillac dealership that had given him poor service.