A 5 ft 10 in (178 m) guard born in Bedford, Indiana, Shepherd played at Carmel High School, where he was coached by his father, Bill Shepherd, Senior He scored 2,465 points in four years and was selected as Indiana"s Mr. Basketball in 1968.
He then played at Butler University, also his father"s alma mater, from 1969 to 1972, and set school records for highest career scoring average (241 points per game) and highest scoring average in a season (278 points per game). He averaged 5.7 points per game in his professional career, and led the American Bar Association in three-point field goal percentage (420) during the 1974-1975 season. Afterward, he worked as a scout for Marty Blake.
Shepherd was inducted into the Indiana Basketball Hall of Fame in 1997.
From 1972 to 1975, Shepherd played in the American Basketball Association as a member of the Virginia Squires, San Diego Conquistadors, and Memphis Sounds.
