A singer with a strong R&B influence, Cobi was eight years old when one of his parents' friends showed him a few basic chords on the guitar. He eventually developed a passion for blues, R&B, and classic rock, and when he was in his teens, jumped from fandom to performing when he formed a blues band with friends. He went on to study at Boston's prestigious Berklee College of Music, and in 2008, he teamed up with five other young musicians in Boston to form the group Gentlemen Hall.
Melding hooky pop melodies with polished harmonies, Gentlemen Hall quickly became one of the hottest acts on the Boston music scene. The group scored a record deal with Island/Def Jam, but in 2014, Cobi opted to leave to pursue a solo career and a different creative direction. (Roughly a year later, the group split up.) In 2015, Cobi released a self-titled four-song solo EP, and later the same year, he toured as a guest vocalist with the British electronic act Above and Beyond. In 2016, he dropped the solo single "Don't You Cry for Me."