In 1969, just two years after graduating from a Tampa, Florida high school, Henry took his guitar and moved to New York City. He ended up downtown in Greenwich Village retracing the footsteps of many popular musical icons playing folk music in coffee houses and working as a street musician. Within six months Henry caught the ear of a CBS record executive who got him an audition for then Epic Records A&R director Don Ellis. Don liked Henry’s original songs and his vocal sound and took him into the Columbia recording studio to record his music. In meetings that followed the idea of Henry moving to Nashville to continue his career was suggested. While discussions with Epic continued a talent manager from Tampa offered Henry an opportunity to come back to Tampa and play a hometown concert.