[6][7] In 2002, Goldsmith formed a post-punk band called Simon Dawes with high school classmate and guitarist Blake Mills.

The band's first album, North Hills marked a sharp departure from the punk-inspired tunes of their youth and embraced a subtler folk rock that has been called the Laurel Canyon sound, reminiscent of Crosby, Stills, and Nash and Jackson Browne.

In 2010, Goldsmith joined Matt Vasquez of Delta Spirit and John McCauley of Deer Tick to form the band Middle Brother.

[14][15] In 2014, Goldsmith was asked by producer T Bone Burnett to join a project called The New Basement Tapes that wrote and recorded songs based on recently uncovered lyrics written by Bob Dylan in 1967.

[16] Goldsmith joined Marcus Mumford of Mumford and Sons, Jim James of My Morning Jacket, Rhiannon Giddens of Carolina Chocolate Drops, and Elvis Costello during the recording sessions, which resulted in an album, Lost on the River: The New Basement Tapes, and a Showtime documentary, Lost Songs: The Basement Tapes Continued.

[17] Goldsmith received co-writing credit for the songs "Kansas City," "Liberty Street," "When I Get My Hands on You," "Florida Key," "Card Shark," and "Diamond Ring."