Sims was born in Minnesota to American parents who were former musicians. He first began creating music at an early age when his father bought him a Casio SK-1 keyboard. At a young age, he began writing lyrics, not necessarily rap. By the time he was 14, Sims was freestyle rapping and was also in various non hip hop bands as well. He attended Hopkins High School in Minnetonka, Minnesota where he met P.O.S and Cecil Otter, (and later other Doomtree members) who would sell beats to Sims. Following graduation, he studied at the University of Minnesota, before dropping out with seventeen credits remaining. Although he was younger than his cohorts, after a while he was invited to become an official member of Doomtree, being the last one to join.
Sims' first release was False Hopes Number Four EP, the fourth in a series of fifteen Doomtree member releases (such as Dessa's and Cecil Otter's), and was released locally. His first national appearance was on P.O.S's debut album Ipecac Neat in 2004, on the song "Lifetime...Kid Dynamite." In 2005, he released his first solo album, Lights Out Paris, in 2005. The album was given very favorable reviews, with URB Magazine giving it a 4.5 out of 5, saying: “As if you needed another reason to lend an ear to Minneapolis hip hop.” It features verses from all Doomtree rappers, Crescent Moon and Toki Wright. The album was released without the help of a record label or distribution, instead using money earned from Doomtree's shows, who would release the album independently.
In 2009, he released False Hopes XIV. Later that year, he featured on P.O.S's album Never Better on the song "Low Light Low Life".
His second solo album, Bad Time Zoo, was released in 2011. It is entirely produced by Lazerbeak. The album was released with music videos for the tracks "One Dimensional Man,", "LMG", and "Burn It Down." The album features a guest appearance from P.O.S. Drew Beringer of AbsolutePunk described the album as "one of the most bombastic hip-hop albums of 2011." On June 24, 2011, "Burn It Down" was named KEXP's sog of the day. Sims released Wildlife EP later that year. The same year, he featured on Astronautalis' album This Is Our Science on the song "Thomas Jefferson."
In 2013, he featured on P.O.S's album We Don't Even Live Here on the song "They Can't Come".
The next year, he released the EP Field Notes, which features production from Cecil Otter and Icetep, among others. It also features Astronautalis.
In 2016, Sims released his full-length solo album More Than Ever. The album announcement also featured news of Sims' More Than Ever tour, featuring Air Credits and taking place in late 2016 and early 2017.
In 2010, Sims' wife Sarah (then girlfriend) needed an emergency pancreas transplant. During the Doomtree's Blowout Three concert, she was in a coma. Sims' experience is documented in a hidden song on "Hey You" on Bad Time Zoo's CD and vinyl release. In 2011, they married.Lights Out Paris (2005)Bad Time Zoo (2011)More Than Ever (2016)False Hopes Number Four (2003)False Hopes XIV (2009)Wildlife (2011)Field Notes (2014)"Burn It Down" (2011)"This Is the Place" (2013) (with Astronautalis)"Uh Huh" (2014)"Triple 6's" (2016)"One Hundred" (2016)"Icarus" (2016)"Brutal Dance" (2016)P.O.S - "Lifetime...Kid Dynamite" from Ipecac Neat (2004)Dessa - "Press On" from False Hopes (2005)Mel Gibson and the Pants - "Landmarked" from W/ Guitar (2005)Mel Gibson and the Pants - "Dead Baby Joke" from Sea vs. Shining Sea (2007)P.O.S - "Low Light Low Life" from Never Better (2009)Astronautalis - "Thomas Jefferson" from This Is Our Science (2011)Culture Cry Wolf - "Second Wind" from Dia de los Muertos (2011)The Hood Internet - "One for the Record Books" from FEAT (2012)P.O.S - "They Can't Come" from We Don't Even Live Here (2012)Big Quarters - "Grown Up" from Somos No Joke (2012)Transit - "Monster See Monster Do" from Occupy Tall Trees (2015)Air Credits - "Gear Shiftn" and "No Limits" from Broadcasted (2016)