Originally from California, where he studied with mandolin great David Grisman, Colby migrated to the Midwest to attend Oberlin College and then stayed to escape the tech boom.
Colby moved to Chicago in 1995 to work with The Special Consensus bluegrass band where he rubbed elbows and shared the stage with many of his heroes like Tim O’Brien, Scott Nygaard, Sally Van Meter, Laurie Lewis, Slavek Hanzlik, J.D. Crowe and John Hartford. Along the way Colby studied fiddle with Missouri State Champion Charlie Walden and played for a short time in a duo with young banjo wizard Noam Pikelny.
Colby teaches at the Old Town School of Folk Music now, and in 2006 he won first prize at the Rocky Grass mandolin competition in Lyons, Colorado. Recent side projects include raising two kids, releasing, managing the Resource Center at the Old Town School of Folk Music, editing the Old Town School of Folk Music Song Book and playing around town with Charming Axe, Barb Silverman, Steve Dawson, Chris Walz, and Lisa DeRosia as well as recording Civil War songs for the Newberry Library.