Stephen graduated from Hampden-Sydney College with a B.A. in Political Science. In 2006, he graduated from Thomas M. Cooley Law School in Lansing, Michigan. During law school he clerked for Glassen, Rhead, McLean, Campbell & Schumacher, at a small Lansing firm where he focused on criminal defense and collections work. Additionally, he clerked in the Norfolk Commonwealth Attorney's Office where he realized his desire to serve the public interest as a prosecutor for the Commonwealth