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Milo performing in San Antonio, Texas in November 2018
Originating in Kenosha, Wisconsin, Ferreira received modest popularity and a cult fanbase following the release of his first two projects, I Wish My Brother Rob was Here and Milo Takes Baths, both of which receiving attention on blogs like The Needle Drop and mainstream publications like Forbes. The recognition led to Ferreira being noticed by rappers Busdriver and Open Mike Eagle, later going on his first tour with them and signing to their label, Hellfyre Club.
Ferreira's debut studio album, A Toothpaste Suburb was announced in March 2014 though it underwent numerous hiccups during rollout and problems with its release, eventually getting released in September 2014. The issues around release resulted with Hellfyre Club folding and Milo founding his label, Ruby Yacht (stylized RBYT), which he currently runs out of his record store, Soulfolks Records in Biddeford, Maine.
He was introduced to hip hop through his uncle, a battle rapper who goes under the name NIZM who showed him Nas. For high school, Ferreira moved with his father to Kenosha, Wisconsin. He participated in theatre in school and was always working on hip hop out of school. His father was often not home and at work so Ferreira frequented online forums to make friends, often on ProBoards. By the time he got to college, Milo had been to 13 different schools.
He first began rapping as part of the Kenosha and a Wisconsin hip-hop trio Nom de Rap, which additionally consisted of rappers Nicholas J and AD the Architect. Following high school, he attended St. Norbert College in De Pere, Wisconsin for Philosophy.
Milo has said he came up with his name at age 16 after reading the book The Phantom Tollbooth by Norton Juster, although in a separate interview with everydejavu he states that his name is an acronym for "maybe i like owls", in reference to his first rap name being "wise owl, himself".
In 2010, Nom de Rap released their first joint mixtape, Greatest Hits Vol. 1.
Milo released his first solo mixtape, I Wish My Brother Rob Was Here in 2011. According to Ferreira, the project was recorded in his bedroom with gear he got over time and he called the quality of the recordings "rubbish." The mixtape, which title is a reference to Del the Funky Sapien's I Wish My Brother George Was Here and Ferreira's deceased friend Robert Espinosa. The mixtape got attention from numerous blogs including Anthony Fantano's The Needle Drop, SputnikMusic and publications like Forbes giving Ferreiara recognition.
Milo Takes Baths was released on February 2, 2012. 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. The EP was once again praised by The Needle Drop and Forbes 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. Following the release, Ferreira caught the attention of rapper Nocando and his label Hellfyre Club which included Ferreira's role-model's Busdriver and Open Mike Eagle. Ferreira had been talking to Busdriver and Open Mike Eagle since 2012 and they had notified Nocando of his presence when he was considering quitting rap music. He later signed and was taken on his first tour, which had Ferreira going to 25 cities. 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. 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. Upon arriving in the state, the "Moving to LA" tour was commenced, starting in St. Louis and ending in Sacramento.
His first official album, A Toothpaste Suburb, was released on Hellfyre Club on September 23, 2014. 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. After leaving Hellfyre Club, Ferreira had the choice to try to convince major label interest but decided to start his own imprint, Ruby Yacht which name comes from the Persian word for a collection of poems, rubaiyat. He later said, "I don't have another option. No one wants to invest money in the art that I'm making, no one out here, except listeners, and that's really dope."
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. The two spent seven days recording (Boyle) and Piles, an EP they finally mixed on the seventh day and released on December 17, 2015 under the name "RED WALL." The two used the sales from (Boyle) and Piles to move to Oakland swiftly and then the full week sales to move back to Milwaukee to start working on his second album, So the Flies Don't Come, mainly due to the cheapness of Milwaukee and Los Angeles "[breaking] my spirit".So The Flies Don't Come was released on September 25, 2015 and wwas entirely produced by Kenny Segal.So The Flies Don't Come was followed with his first headling tour.
In 2017, Ferreira announced his third studio album, titled Who Told You to Think !!?!?!. The project was slated with an August 11 release date and was subsequently called one of the most anticipated albums of 2017 by Rolling Stone. His third studio album entitled "who told you to think!!?!?!?!", was released through the Ruby Yacht label on 11 August 2017. In 2018, Ferreira performed in Europe for the first time His fourth LP, Budding Ornithologists are Weary of Tired Analogies was released on September 21, 2018.
Ferreira founded his label, Ruby Yacht (stylized as RBYT) in Milwaukee, Wisconsin. Named after the Rubaiyat of Omar Khayyam and Ferreira's grandmother, it is entirely self-owned by Ferreira and self-financed Ruby Yacht is currently ran out of Ferreira's record store, Soulfolks Records in Biddeford, Maine, which opened in April 2018. The store sells cassettes, vinyls and CDs and mainly sells independent rap music. It is also the only record store in Biddeford, Maine.
There are two other artists signed to Ruby Yacht, Ferreira's childhood friend and musician Safari Al and reowned Los Angeles recorder producer Kenny Segal. Ferreira hasn't signed any other artist, mainly due to indie rap's lack of numerous album deals and his personal beliefs.
Ferreira is a vegetarian and currently lives in Biddeford, Maine. He moved to Los Angeles with his friends and frequent collaborators Safari Al and Nedarb Nagrom in 2014 to be closer to his then-label Hellfyre Club and moved to Boyle Heights and later, a storage shed in Echo Park following the break-down of the collective and the label being made defunct. Ferreira moved back to Wisconsin before deciding on Maine after his first headline tour. Speaking on his move to Maine, Ferreira said, "It's far away from everything. I'm a bit of a wild person. I like to be free, run around, holler, do weird shit. I don't like people looking at me. I need space." He also said in an interview with Vulture that his marriage and his wife's pregnancy were big reasons for the move to Maine.
Ferreira attended St. Nobert College in De Pere, Wisconsin, a liberal arts institution, studying Philosophy. Ferreira dropped out of college after moving to Los Angeles, saying he was "trapped in college" to LA Weekly in 2013.
Ferreira is married in 2016. In July 2017, Ferreira announced on social media that he had a son who was born in December 2016, later confirming in an interview with Vice.