Free began his career in education over 20 years ago in Richmond, Virginia where he taught both Math and English at multiple public middle and high schools in the area.  Upon his transition to independent schools he has taken on a number of roles, including Admissions Associate, Director of Student Activities, English Teacher, Assistant Athletic Director, and Associate Director of Admissions. He has coached Boys’ Basketball, Track and Field, and Girls’ Tennis as well. Free is currently the Director of Admissions at De La Salle High School.  

Originally from New York, his career path has guided him from Fairfax County, Virginia, to Tokyo, Japan with stops in Maryland, Santa Cruz, San Francisco and Concord, California.  Free received his Masters Degree in Independent School and Nonprofit Leadership from the Klingenstein Center, Teachers College at Columbia University.  His undergraduate studies were at the University of Maine, Orono, where he played wide receiver and was a founding member of the Student Heritage Alliance Center. He is currently the co-chair of the Vanguard Conference for young Black men and their families in independent schools in the Bay Area.  An avid basketball player, Free enjoys playing at San Quentin State Prison where he has used the game to build lifelong relationships and make a greater impact in the community.