During his early years, Jackson began his career as a talent agent for the Hubert Long Agency. He later worked with Loretta Lynn and Conway Twitty until becoming the road manager for Johnny Rodriguez. Jackson went on to work as an agent for Charley Pride at the late Country Music Hall of Fame member’s booking agency, Chardon, in Dallas. While working with Pride, Jackson discovered the new talent of both Neal McCoy and Janie Fricke. Later, Jackson went on to manage Fricke and later they married. He later married Sherry Jackson and returned to his college alma mater, Sul Ross University, in Alpine. Along with his wife Sherry, they tutored the football athletes while supporting the the Lobos football team. Jackson loved coon dogs and wrote and published a popular book of poetry, inspired by his love of the breed, titled The Coon Dog Chronicles. He lived out his dream by returning to Alpine and his Sul Ross University, producing and promoting music concerts throughout Florida and Texas. Sul Ross University gave him the honorary title “Mr. Sul Ross” then went on to name the athletic field house after him. He once said, “A promoter is only as good as his last show.” Jackson’s final concert was only three days before he passed: Asleep at the Wheel at the Cailloux Theater in Kerrville, Texas. The show was a sell-out.