Kenny comes from a bluegrass family. His grandfather plays the button box and his father plays the banjo. He has been singing his whole life with cousins and sisters. In 2015, Kenny moved to Nashville from Cleveland to pursue music. He lives in a homemade 294-square-foot house on wheels and plays six nights a week at Rippy's and various places along the Broadway strip. His wife has sacrificed the most, taking a huge pay cut to move to Nashville.