He then studied English at Queens University of Charlotte,[2] and received an MFA in fiction writing from the School of the Art Institute of Chicago.

[3] Lindsay began his career playing and singing in Benji Hughes, as well as fronting his own rock bands The Catch Fire and The Young Sons.

[7][8] The title is a reference to the Plaza-Midwood neighborhood where Lindsay lived and a failed suburb by University of North Carolina at Charlotte where he grew up.

[11] Shawn Haney for Performer wrote, "One of the best records to come out of the Southeast over the course of the decade, it’s full of life, bleeding with happiness and melancholy at the same time.

He also signed a music publishing deal with North Star Media, performed at several festivals, and began preparations for his next releases: the EP Could It Be Christmas?, which has a loose holiday theme (November 29, 2011); Rumormill, the debut LP of Lindsay's side project The Catch Fire (No More Fake Labels, December 6, 2011).

[4] On December 22, 2017, File 13 released "Zebulon", a single from Lindsay which features a horn arrangement written and performed by Matt Douglas of The Mountain Goats.

In related interviews, Lindsay shared details about his forthcoming fourth full-length album, "Big Stage", recorded in Hollywood at Barefoot Studios, set for release in 2025.

[37][38] Caitlin Cary reached out to Lindsay to form the group after watching the video for his song "NC GOP Just Don't Know Me" on YouTube.

The group included musical luminaries like Rhiannon Giddens, American Aquarium, Hiss Golden Messenger, The Love Language, Chris Stamey, Pierce Freelon, and members of the Mountain Goats and Black Crowes.

[35][43][44] In December 2016, Lindsay organized and performed at "Hate Free By The Sea" in Wilmington, NC, a benefit concert in support of a UNCW student who received threats after being bullied by a faculty member because of her race, religion, and sexual orientation.