Born in Chicago, Illinois, Milo grew up in Saco, Maine. He first began rapping as part of the Kenosha, Wisconsin hip-hop trio Nom de Rap, which additionally consisted of rappers Nicholas J and AD the Architect. The group released their first joint mixtape, Greatest Hits Vol. 1, in 2010.

Milo released his first solo mixtape, I Wish My Brother Rob Was Here in 2011. Milo Takes Baths was released in 2012. The song “Kenosha, WI” was published by Johns Hopkins University Press in a 2012 issue of the journal Postmodern Culture.

Milo released two EPs, Things That Happen at Day and Things That Happen at Night, in January 2013. The Cavalcade mixtape followed in July 2013. In November 2013, he appeared on Hellfyre Club’s compilation Dorner vs. Tookie. He released Poplar Grove (or How to Rap with a Hammer) under the moniker Scallops Hotel in November 2013. His first official album, A Toothpaste Suburb, was released on Hellfyre Club on September 23, 2014. In 2015, he released So the Flies Don’t Come, which was entirely produced by Kenny Segal.