After college, he started a Chicago-based band called Milano, a "gypsy prog-rock" indie group with co-members Valerie Strattan Guerra, Steve Enison, Justin Ferwerda, Hans Moscicke, and Alissa Strattan,[7] which broke up in 2013 after having created three studio albums[8] (several singles of which were remixed by EMD artist Hanzel).
[10] Guerra's next releases would be under Essential Records that, at the time, had a distribution deal with Sony Music.
First, a quiet release of an extended play, Working Demos, that found an audience on NoiseTrade.
[11] This would be the precursor to his first major label full length album, released on April 21, 2015, Little Songs, with Essential Records (Sony).
[14] In April 2020, Guerra released his second full-length album of devotional music, Keeper of Days.
"[20] In May 2023, Guerra released his third devotional music album, Ordinary Ways, to widespread critical acclaim.
"[23] Guerra again self-produced his album, with his long-time musical collaborator, his wife, Valerie, on strings.