In high school, Bill Hobbs attended Milton Academy where he was named the fullback on the all-New England prep team. After his freshman year at Harvard he made the 1968 Olympic team, stroking the pair-oared shell that finished fifth at Mexico City. While at Harvard he rowed in the eights that won the 1969 and 1970 Eastern Sprints, and then later rowed the eight at the 1972 Olympics.
After college, Bill Hobbs briefly taught math at Milton Academy, and then earned an M.B.A. from Harvard. He later worked as a corporate planner, starting out with MC Corp, for whom he worked in Brazil and Kentucky. He later became CEO of Bridon American, then founded Certex Distribution. He was then CEO of Trend Technologies and JC Whitney, and near the end of his business career he was an operating partner with High Road Capital Partners. Hobbs is a member of the National Rowing Hall of Fame and the Harvard Athletic Hall of Fame.