James grew up in a musical family, starting with the violin when he was four years old. He focused on small ensemble playing, performing and winning in string quartet competitions across the United States, as well as playing in jazz, rock, and folk bands. As a teenager he picked up mandolin, banjo, and guitar, eventually dedicating the majority of his time to the banjo. James was a 2017 FreshGrass Banjo Award finalist, and plays in several bluegrass and folk bands around Boston.