A former special ed teacher, Randy was an administrator at a residential treatment center in the Berkshires for many years. In 1997, he established North Star Rare Books and the Museum of Civil Rights Pioneers, which was designated the nonprofit W.E.B. Du Bois Center in 2006. Randy has published works on Black history, including "Against the Tide: Commentaries on a Collection of African Americana", with a foreword by Henry Louis Gates, Jr.
Together with co-chair Gwendolyn VanSant, Randy helped to establish the town-appointed W.E.B. Du Bois Legacy Committee in 2018.