When Leonard was 15 years old, he began leading worship at the college ministry services on the campus of the University of Arkansas at Monticello.

Leonard credits the events of that night as the inspiration for a song he wrote later in his career, "Good Lord".

[3] After graduating from college, Leonard began playing in the Christian Southern rock band, Jackson Waters.

[4] When Jackson Waters disbanded, Leonard began touring regularly with the rock band NEEDTOBREATHE, playing keyboard.

"[8] With the disbanding of All Sons & Daughters, Leonard started The Creak Music with friends Seth Talley and Brad King, a new production group and independent label.