Makonnen was born in Los Angeles, California and moved to Atlanta in 2002 when he was 13 years old. He is of mixed race background, having African, Indian, Irish, Belizean, German, and Chinese heritage. His mother was a nail instructor and has worked in the beauty business for over 30 years. His grandmother was an opera singer, which influenced his musical career. He described his childhood as "semi-nice, semi-poverty". During his high school years, Makonnen was inspired by local rappers Young Jeezy and Gucci Mane to try out making music. His early songs were a mix of pop, rock and hip-hop.
In March 2014, Mike Will was able to reply to Makonnen and brought him to DTP studios, where he played some of his songs to producer Metro Boomin. Metro instantly liked Makonnen and stayed in touch with him. Later, after recording six songs together, Metro brought fellow Atlanta producers Sonny Digital and 808 Mafia, who were all unusually impressed with him. Two days later, Makonnen recorded the song "Don't Sell Molly No More" with Sonny Digital, which would later help launch his career. Sonny Digital introduced him to other Atlanta producers such as DJ Spinz and Dun Deal. He started gaining local fame within the community with songs such as "Living On The Southside", "Sneaky Lady" and "My New Friend".
In July 2014, the singer released his self-titled EP ILoveMakonnen, which included the singles "Club Goin' Up on a Tuesday" and "Don't Sell Molly No More". The latter reached pop singer Miley Cyrus, who shared it on her Instagram. The post got over 210,000 likes and counting that brought a lot of new fans to Makonnen. On August 15, 2014, Vice included his song "Whip It" in their Staff Picks for the Week list, commenting: "Makonnen's voice is incredible! ... How could you not have a good time listening to this song? If there is anyone I trust to teach me how to whip it, it is definitely my friend Makonnen."
In late August 2014, after hearing "Club Goin' Up on a Tuesday", Drake reached out to one of the song's producers, Sonny Digital, to ask to remix the song. Makonnen quickly agreed to send the beat to Drake, but didn't think much of it. However, two days later Drake released a remix to the song, much to Makonnen's surprise. The Atlanta singer later commented: "Yeah, I surprised. Shocking. Drake listens to Makonnen. It was great. I was excited. Surprised, shocked. Just overwhelmed." The remix, simply titled "Tuesday" went viral and led to increased media interest in iLoveMakonnen.
In late August 2014, Makonnen was featured in XXL 's The Come Up section, which focuses on blowing up artists. He later stated that he is not looking for a major label deal and instead plans to go touring and recording music independently: "I'm not too thirsty to sign a deal. Cause a label will really just take all your free music down and you have to be somebody's bitch." He is also working on a collaboration project with Mike Will, which is set for release before the end of 2014. On September 1, 2014, it was announced that Makonnen, in a contradiction of his previous stance, had signed to Drake's label OVO Sound, which is distributed by Warner Bros. Records.