Growing up around St. Louis, MO, Shepherd was a water bug and spent his summers on the Mississippi River. When he and his family later moved to Stephens City, VA, he made time to go down to the Potomac River and Lake Anna. He ended up graduating from George Mason University and in 1993 made his way to Nashville, a place he still spends a lot of his time today. Eight years passed, but in 2001 he and veteran song writer Wood Newton wrote “Riding with Private Malone”, performed by David Ball, which shot up to the #2 US Billboard Country Chart spot and #36 on the Billboard Hot 100. With the success of this song, Shepherd was sought out by both up-and-coming performers and old, established acts alike.