The term, “Big Daddy,” hails from Black Southern culture where grandfathers are called “Big Daddy” to connote a larger perspective than a father. Big Daddies have more resources and are more generous with these than daddies; they have more patience than daddies and more time to talk to boys. They are favorite staples in the Black community in southern states. Our program is based on this cultural tradition. We recruit and screen successful urban men who want to make a difference in the lives of young males. These “Big Daddies” serve as online mentors who engage young males weekly for dialogues reflections, and success planning for the future. “Big Daddies” engage their mentees via email and Zoom for weekly meetings where male discussion and guidance take place. These include personal concerns, career explorations, and academic tutoring.