[3] After graduating from University High School in 2001,[3] at the age of seventeen he hitchhiked to the west coast and earned a living as a busker on streets, sidewalks, and pedestrian malls.

He met Ryan Koenig and Joey Glynn of the St. Louis band The Rum Drum Ramblers while he was playing on a street in Asheville, North Carolina.

Riverboat Soul, the first album with The South City Three, was recorded in July 2009 at the Nashville studio of producer Phil Harris using vintage instruments and electronics.

[15] The group is thought to be "artfully dodgy ambassadors for old-time music, presenting and representing the glories of hot swing, early jazz and ragtime blues" who have "made riverboat chic cool again.

"[27] His repertoire consists of a mix of Americana, early jazz, ragtime for string instruments, country blues, Western swing, Vaudeville, and Appalachian folk.

[6] Musicians that have influenced him include Howlin' Wolf, Jimmie Rodgers, Bill Monroe, Milton Brown and the Musical Brownies, Modern Mountaineers, Sleepy John Estes, Henry Townsend, Frank Fairfield, Fats Waller, Emmett Miller, Marc Bolan, Peter Lafarge, and Willie Dixon.