Having lost his father at a young age, Jennings' childhood was marred by hardship, receiving a ten-year prison sentence for arson at the young age of 14. His time spent in jail helped to change his life around, developing a deep passion for music, finding solace in the honest and emotive sound of Erykah Badu, which would be reflected in Jennings' own musical style. Being in jail led to Jennings to develop a very introspective and deeply conscious sound, reflecting upon the hardship he endured and the lessons learned. Upon his release in 2002, he recorded a four-song demo and began to perform live, appearing at the famous Apollo nightclub.

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