[1][2] Fly started coaching as a student at the University of Kentucky, assisting at NAIA Georgetown College for one season.
After graduation, Fly became a video coordinator assistant for the NBA's Charlotte Bobcats for one season before taking a one year internship at NCAA's corporate offices.
[2] He returned to coaching joining Leonard Hamilton's staff at Florida State where he served as a video coordinator for three seasons.
On April 5, 2018, Fly was promoted to become the fourth head coach in Florida Gulf Coast history, replacing Dooley who accepted the same position at East Carolina.
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