 He then returned to Kentucky, entering a JD/MBA dual-degree program at the University of Kentucky, where he was one of the first Kentucky MBA scholars and one of the first two Bert T. Combs Scholars, the College of Law's top scholarship.After earning both degrees in 1998, he worked as an attorney with Greenebaum Doll & McDonald and later Keating, Muething & Klekamp, where he focused on estate planning and corporate law.Although a member of the Democratic Party during his collegiate years, shortly after graduating Grayson became a member of the Republican Party, citing his conservative beliefs.