Masterman earned his B.A. in economics and mathematics from Vassar College in 2013. He is a Vanderbilt Law & Economics Scholar. He was granted an ABA Janet D. Steiger Fellowship in 2015. Masterman has earned Vanderbilt Scholastic Excellence Awards for Administrative Law, Federal Courts and the Federal System, International Trade Law, and Patent Law. He served as a staff member for the Vanderbilt Law Review in 2015-2016 and as an articles editor in 2016-2017. During summer 2016, he worked as a Legal Intern at the Federal Trade Commission’s Bureau of Competition. He was a member of the Vanderbilt Moot Court Board in 2015-2017.