Bob James sailed Flying Dutchman with his younger brother, David James, at the 1968 Mexico City Olympics. They grew up learning to sail on the Chesapeake Bay in Virginia. James represented the Yacht Haven Club at the Olympics. He attended Georgia Tech, graduating with a degree in aeronautical engineering in 1955. He started working for the Martin Corporation, where he helped develop missile technology. He later became an aerospace engineer at NASA Langley Research Center, working there for 30 years on spaceflight and aircraft design. He was a founding member of the Ware River Yacht Club (WRYC), serving as Commodore and Race Committee Chairman.