Born in Manhattan, New York, and raised in Miami, Florida, Caldwell’s life and career was a mixture of one part providence, two parts talent, and ambition. His first professional break came when he landed the gig as Little Richard’s rhythm guitarist at the age of 17, along with his working band, Katmandu. Growing weary of the touring circuit and believing the band could strike out on its own, Caldwell and Katmandu left the Little Richard gig.