Cleveland was born in Memphis, TN, after Dr. Kings assassination in 1968, his Mom moved him and his other siblings to Decatur, IL. He graduated from Stephen Decatur High School in 1975. He went on to Lakeland Jr. College to get his Associated degree in Radio & TV Broadcasting. He later got his Bachelor degree in Radio Broadcasting from The American Broadcasting school in Oklahoma City, OK. Cleveland moved back to Memphis in 2015 to pursue his dream in broadcasting. He started working at WLOK in May of 2015.