Jay graduated with honors from St. Ignatius, winning the prestigious Bellringer Award and the accompanying $10,000 scholarship and going on to Villanova University, where he was recognized as one of the 12 most promising minority male college students in America; he worked for both the National Hispanic Institute and the World Bank; won fellowships to study at Georgetown, Cambridge and Harvard; and co-founded The Paragon, an on-campus organization at Villanova dedicated to developing and teaching leadership in the African-American community.