Stapleton served as President of Marsh and McLennan Real Estate Advisors of New York from 1982 until 2001.

[2] He has served on the board of directors for several companies including Allegheny Properties, Metro PCS, TB Woods, Winston Partners and Abercrombie & Fitch.

[4] Stapleton is a Senior Advisor to Stone Point Capital and a Director of Tenax Aerospace.

He serves on the boards of the Vaclav Havel Foundation, the American Friends of Compiegne, the United Way Tocqueville of France, the 9/11 Memorial & Museum, the World War I Centennial Commission, and the Trust for the National Mall.

He and his wife live in North Palm Beach, Florida and have two adult children; his son Walker Stapleton was elected Colorado State Treasurer in 2010.