Boeckner began his career in the Victoria, Canada music scene, playing in multiple bands including Atlas Strategic.

Since that time, he has been part of projects including Handsome Furs and Divine Fits with Spoon frontman Britt Daniel.

[2] In 2022, Boeckner joined Arcade Fire in a session capacity, touring and performing with the band in support of their sixth studio album, WE.

Making his live debut at the Toulouse Theatre in New Orleans, Boeckner subsequently appeared in the video to the band's twenty-fourth single, "The Lightning I, II".

[4] In 2000, Boeckner co-founded notable British Columbian band Atlas Strategic with organist/vocalist John Pollard, and recorded their debut Rapture, Ye Minions!.

[6] Boeckner contributes his guitar skills, while also splitting songwriting duties and the role of lead singer with band-mate Krug.

[14] The podcast focuses primarily on Canadian politics from a left-wing perspective and is broadly a part of the so-called Dirtbag left, featuring frequent guest appearances from figures associated with that scene.