Simon is the Executive Director of Schools for Lee Montessori Public Charter Schools in Washington, DC. He is the author of "What If I'm Wrong? and Other Key Questions for Decisive School Leadership." He was the founding principal of DC International School, a public charter school in Washington. The school is an authorized International Baccalaureate World School and a Tier One high-performing school. Simon is a 2004 Mitchell Scholar. He received a Master's Degree in Anglo-Irish Literature from University College Dublin. Simon's thesis research examined masculinity and comedy in the work of Kavanagh, Beckett, Durcan, McCabe and Behan. He spent a year as an Urban Scholar at Harvard where he obtained a Master's Degree in Technology, Innovation and Education. At Harvard he examined innovative models of schooling that could close gaps in achievement among students from underprivileged communities. Simon believes the traditional schooling model does not adequately serve all sections of the community and that the economic and social demands of the twenty first century require innovation and a commitment to helping every child learn. Simon obtained his undergraduate degree from Yale.