Sterling was born in 1989 in Uniondale, New York to Jamaican parents, Cleveland and Sophia Sterling. He grew up with seven full siblings and at least 12 half-siblings. To stay away from the prevalent gang life in which some of his brothers joined, Sterling started wrestling at Uniondale High School in 2004.
Sterling opted to enroll at Morrisville State College where he continued wrestling. During his time in Morrisville, Sterling met Jon Jones and trained on the wrestling team. After his freshman year, Sterling transferred to Cortland and eventually became a two-time NCAA Division III All-American with a record of 87-27. He developed a serious interest in MMA his sophomore year when he saw pictures of Jon Jones doing BJJ matches and fighting.
He earned the nickname “The Funk Master” from his unorthodox wrestling style.