Fitzsimmons was born the youngest child of two blind parents, and was raised in Pittsburgh, Pennsylvania. He is said to have developed his multiple instrument abilities from his mother and father, both of whom were recreational musicians. His childhood home even housed a fully functional pipe organ, said to have been built by hand by his father. He was taught the piano and trombone during elementary school, and began teaching himself guitar during his Jr. High years. He is also proficient at the banjo, melodica, ukulele, and mandolin, and is known for mixing folk music with electronica in some of his production. In addition to performance abilities, Fitzsimmons is credited as the engineer and producer of all his recorded music. He is often compared to contemporaries Iron & Wine, Sufjan Stevens, and the late Elliott Smith.