In 2017, country singer Jake Owen discovered Fleet performing cover songs at a wedding, and booked him as an opening act.
Fleet also competed on Real Country, a singing competition on the USA Network where Owen serves as a judge.
Fleet placed second on the show, which led to him recording a number of independent releases prior to signing with Big Loud.
[3] Fleet co-wrote his debut single "Where I Find God" with Nashville-based songwriter Connie Harrington.
She had discovered Fleet through his social media accounts, where he would post a cover of a gospel song every Sunday.