[2] After graduating from high school in three years, Ashby attended the Ithaca College music program on scholarship at age 16.

During his time at university, Ashby helped to produce several local jazz festivals.

In 1987 Ashby left the Pittsburgh Symphony and founded MCG Jazz, a program of the Manchester Craftsmen's Guild.

[3] As a guitarist, Ashby performed and recorded with Slide Hampton, Claudio Roditi, Nancy Wilson, Paquito D'Rivera, Herbie Mann, Phil Woods, The Dizzy Gillespie All-Star Big Band.

Ashby is the EPP Goldman-Sachs fellow at the National Museum of American History (NMAH).