Milo was born Rory Ferreira in Chicago in 1992. Born to young parents with complicated lives, Ferreira changed schools and relocated often during his young life, living in Maine, Wisconsin, and Illinois before finishing high school. He became interested in rap after hearing Nas for the first time as a preteen, and by high school, he was part of the Wisconsin hip-hop collective Nom de Rap under the stage name Milo. Ferreira alluded to several different origins of the name Milo, stating in some interviews that it stemmed from an early moniker, "Wise Owl, Himself," and in others that it stood for "Maybe I Like Owls." In addition to appearing on projects with Nom de Rap, Milo released his first mixtape, I Wish My Brother Rob Was Here, in 2011. Taking a defiantly grassroots, anti-commercial stance from the beginning, Milo chose to release his music independently and build up a devoted fan base by focusing on honing his craft and atypical personalized style rather than chasing fame with a traditional team of managers, producers, stylists, and the like. His audience grew with each project he released, and a slew of new music came from Milo in the form of mixtapes like 2012's Milo Takes Baths; EPs such as 2013's companion pieces Things That Happen at Day/Things That Happen at Night; and more solidly conceived albums such as 2014's A Toothpaste Suburb, 2015's So the Flies Don't Come, and many others. He also released several albums of more experimental hip-hop under the name Scallops Hotel. Milo's recordings were often released on limited-edition cassettes, usually via his own Ruby Yacht imprint, that quickly became out of print collectibles. Milo released his most ambitious album to date, Who Told You to Think??!!?!?!?, in 2017. The full-length Budding Ornithologists Are Weary of Tired Analogies arrived the following year.