[6] After his parents died, he converted the farm to row crops, which he leases to a neighboring farmer so he can be on the road to perform.

[7] In addition to playing locally with a cousin, Whitmore, after a short stint in San Francisco, moved to Iowa City and got involved in the punk rock and the DIY scene, forming a band called Lost Cause.

The song "Civilizations" off his 2015 record, Radium Death, is about how an oil pipeline running from South Dakota to Illinois was going to go through his grandmother's property on their farm.

[17] The record garnered favorable reviews by critics and a video shot in downtown Los Angeles featuring Patterson dancing to her cover of Whitmore's song.

Covers include songs by Bad Religion, Bill Withers, Captain Beefheart, Johnny Cash, The Magnetic Fields, and ZZ Top.

[21] Whitmore has toured with Chris Cornell, City and Colour, Murder by Death, Clutch, Lucero, Converge, Red Sparowes, Modern Life is War, Frontier Ruckus, Frank Turner, Esmé Patterson and The Low Anthem.

[7] Whitmore has a long-term musical relationship with his cousin Luke Tweedy, head engineer and producer at Iowa City's Flat Black Studios.