Stephanie Cuba, who is married to Cunningham, and been attending Berkshire Meetings with him for more than a decade, is a real estate consultant based in New York City. Her real estate career spans development at Avalon Bay, investing at State Street Global Advisers, and legal advisory at Paul Hastings.

A graduate of the University of Pennsylvania and Cardozo Law School, writing accomplishments range from prize-winning non-fiction to freelance editing and popular advice columns for women. A serial entrepreneur, projects have included the Fireball Network, specialising in networking skills training, and MomUp, a coaching and mentoring program for young mothers. Cuba serves on the Board of Brooklyn Excelsior Charter School and the Advisory Council of Montefiore Medical Center/Einstein College of Medicine.