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 that Douglass was the first student he would ever encourage NOT to go to college and instead pursue his passion full time — advice Douglass ran with.
Douglass's evocative, alternative sound has been compared to Tori Amos, Jeff Buckley and Rufus Wainwright. His numerous accolades include being a finalist for both the 2005 International Songwriting Competition and the 2004 Independent Music Awards; he was the winner of the 2003 Grammy Fest Awards in New York City, as well as the inaugural performer on the American Red Cross "Save A Life Tour" in 2003. Douglass actively appears at listening rooms, clubs, festivals, and campuses throughout the United States and has shared the stage with artists like They Might Be Giants,Grace Potter, Melissa Ferrick, Jason Mraz, Regina Spektor, Third Eye Blind and Margaret Cho. Douglass' music video for "Hang Around" charted for six consecutive months on LOGO TV's "Click List" Top 10 Video Countdown in 2008, following similar success on LOGO TV with his video for "I Wanted To Run".