T.R. Hildebrandt graduated from Kiel High School in 1999. He went on to attend (in order) Lakeland College, UW-Milwaukee and Lakeland College, thus achieving junior classman status in just over fifteen years. He was a longtime resident of Milwaukee, where he dabbled to varying degrees of success in art, music, addiction, heartbreak, activism and the bottom rung of the upscale hospitality industry. He is known to a tiny subset of the population for his zine, Boyish Hips.