Holly was trained by Danny Davis, Doug Basham and Jim Cornette before making his wrestling debut in 1999 as the Damaja. On January 6, he and David C. were awarded the OVW Tag Team Title when Nick Dinsmore no-showed and Rob Conway was counted out. He was also a three-time OVW Champion, defeating the likes of Dinsmore, Flash Flanagan, and Nova.
In 2003 he was given the managerial services of Tough Enough II winner Jackie Gayda, and then on May 29, made his WWE television debut (as Danny Basham), teaming with Doug Basham to form the tag team from Columbus, Ohio, the Basham Brothers. They were later given a valet, Shaniqua.