Douglass was born and raised in rural Vermont, winning local talent shows in his early teens. He taught himself to play the piano and guitar by ear and took up songwriting in junior high. While attending Brewster Academy, a college-preparatory boarding high school in New Hampshire, Douglass composed and recorded the material for his first two albums. On graduation day, Brewster Academy's headmaster presented him with a music award, publicly announcing Read more on Last.fm