At age twenty, Lieb left his hometown of Fairfield, Iowa to pursue music professionally in New York City. In addition to attending classes at The New School, Lieb began singing at local open mic sessions, where he was introduced to Jonathan Daniel of Crush Management.[1] Together, the two began meeting with record labels and Lieb began collaborating with other songwriters.[1] At the height of those meetings, Lieb's father passed away and he abruptly stopped his music career altogether.[1] Lieb moved back to his hometown of Fairfield, Iowa, and went more than three years without playing or writing a song.[1]