[4][5] Ferreira received moderate popularity and a cult following after the release of his first two projects, I Wish My Brother Rob Was Here and Milo Takes Baths.
He was noticed by rappers Busdriver and Open Mike Eagle, later going on his first tour with them and signing to their label, Hellfyre Club.
[7] Due to challenges he had faced in the album's rollout, Ferreira subsequently founded his own record label, Ruby Yacht (stylized RBYT).
[11] He was introduced to hip hop when his uncle, a battle rapper who goes by the name NIZM, showed him music by Nas.
[16] The mixtape's title is a reference to Del the Funky Homosapien's I Wish My Brother George Was Here and Ferreira's deceased friend Robert Espinosa.
[26] Released three months after I Wish My Brother Rob Was Here and was a lot more refined than the mixtape, spending more time crafting it and attempting to stray from the nerdcore lane he had established himself into with his first project.
[29] The song "Kenosha, WI" had already been published by Johns Hopkins University Press in a 2012 issue of the journal Postmodern Culture.
[34] In June 2014, Ferreira moved with his friends Nedarb Nagrom and Safari Al to Los Angeles to be with his label and collective Hellfyre club.
[36] Ferreira left Hellfyre Club shortly afterwards, stating his dissatisfaction with the rollout of his debut studio album A Toothpaste Suburb which led to him not getting paid from the preorder.
[37] After leaving Hellfyre Club, Ferreira had the choice to try to convince major label interest but decided to start his own imprint, Ruby Yacht, the name of which comes from the Persian word for a collection of poems, rubaiyat.
"[39] After leaving Hellfyre Club, Ferreira remained in Los Angeles, moving from his previous apartment to a storage shed in Echo Park with friend Safari Al.
[44] The album was included on the year-end lists by Rolling Stone,[45] Spin,[46] The New York Observer,[47] The Boston Globe,[48] and Impose.
[53] On October 1, 2018, Ferreira announced that Budding Ornithologists Are Weary of Tired Analogies would be his final rap album as Milo.
[62] There are two other artists signed to Ruby Yacht, Ferreira's childhood friend and musician Safari Al[63] and renowned Los Angeles recorder producer Kenny Segal.
[64] Ferreira hasn't signed any other artist, mainly due to indie rap's lack of numerous album deals and his personal beliefs.
[10] Ferreira attended St. Norbert College in De Pere, Wisconsin, a liberal arts institution, studying philosophy.
[42] In July 2017, Ferreira announced on social media that he had a son[69] who was born in December 2016,[38] later confirming in an interview with Vice.