After earning his Bachelor of Arts degree from Michigan State University, Dylan went to law school at Wayne State University, where he graduated cum laude and was active as a senior member of Moot Court and in the Entrepreneurship and Business Law Society. During law school, Dylan worked as a transfer pricing intern at General Motors, drafting contracts to handle the transfer of vehicles, parts, and accessories across international borders. He also performed legal and economic research for law school faculty regarding the use of bonding in the principal-agent relationship, and spent time as a member of the Wayne State Disability Law Clinic, where he provided free legal services to underprivileged citizens of Detroit who suffer physical and mental disabilities.