[2] Originally from Meriden, New Hampshire, he is also a founding member and co-songwriter (along with former Okkervil bandmate Jonathan Meiburg) for Shearwater (2001–2009), another Austin band.

Sheff attended Kimball Union Academy, where his creativity was encouraged by a teacher named Simon Harrold,[3] and was an English major at Macalester College in Saint Paul, Minnesota.

Sheff has collaborated with The Mendoza Line on the duet "Aspect of an Old Maid" and played the piano on the Palaxy Tracks album Cedarland.

With Okkervil River, he produced Roky Erickson's 2010 album True Love Cast Out All Evil and provided backing musicianship.

Sheff contributed a large amount of original music writing to the articles section of Audiogalaxy before the service was shut down.