Born and raised in Asheville, Jackson graduated from Asheville High School. While there, he met and began dating his eventual wife, Sally. After graduating from the University of North Carolina at Greensboro, Jackson attended the University of Miami School of Law, located in Coral Gables, Florida. After obtaining his Juris Doctorate from the University of Miami, Jackson practiced law in Coral Gables with Falk, Waas, Hernandez, Cortina, Solomon & Bonner, P.A. However, Asheville beckoned and Jackson and Sally decided to come home.