After graduating from high school, he attended the Australian Institute of Music while working with other musicians to develop his unique sound and artistry. He had performed in countless local churches, clubs, cafes and music festivals throughout Australia and the UK, mostly singing Christian gospel songs he had written.
During a breakdown in 2016 when he was banned from singing at church and dismissed by his evangelical leaders for composing gospel music, Jesse was woken by a horrible but enlightening, prophetic dream one night to establish himself as a mainstream artist instead. Everything about what he thought he knew about his faith and belief changed. That night, Jesse officially "took his cut from high" and moved into the pop scene. This is the idea behind his song, What I'm Tryna Tell Ya, in which he penned in 10 minutes.