Douglass was born and raised in rural Vermont, performing in musical theater and winning local talent shows in his early teens.
He taught himself to play the piano and guitar by age 14, and began writing his own original songs throughout junior high.
[citation needed] His roles included "Hero" in A Funny Thing Happened on the Way to the Forum, alongside actor Topher Grace who played "Pseudolus", while attending Brewster Academy.
[citation needed] Douglass is an independent musician with eight and a multitude of digital singles and music videos.
Douglass has been compared to artists like Tori Amos, Jeff Buckley, Patty Griffin and Rufus Wainwright.