The leadership team at MassMonopoly has a history of experience in design, illustration, finance, organizational behavior, law, and economics. They have worked at various companies such as Weymouth Design, FI Fox News, Institutional Investor Magazine, Civil Air Patrol, Answerthink, Stratus Computer, and Yankee Atomic Electric Co. They have also received education from well-known institutions such as Pratt Institute, Babson College, and Universite de Paris.