He was born in 1949 in New York, New York to Winthrop H. Smith and Vivian G. Brown. Smith is now an entrepreneur, private investor, and chairman and CEO of Summit Ventures NE, LLC, which owned and operatedSugarbush Resort in Warren, Vermont from October 2001 until it was sold to Colorado-based Alterra Mountain Company in January 2020. Smith is credited with restoring Sugarbush to the status it originally had when founded by Damon and Sara Gadd in 1958. He also serves as a director of Eaton Vance Corporation and is Chair of the Board of The Nature Conservancy in Vermont. He is currently the past chairman of The National Ski Areas Association and a member of the Board of the Vermont Ski Areas Association. Previously, he served on the Boards of AGF Management in Canada, the Richardson Financial Group, and Richardson-GMP in Canada. He was also Chairman of The Vermont Business Roundtable and the Lake Champlain Regional Chamber of Commerce. He is also an Honorary Commander of the Vermont Air National Guard. His former philanthropic duties included serving on the Boards of Deerfield Academy, the , The Winthrop H. Smith Memorial Foundation, the New York City Ballet, The Economic Club of New York, Outward Bound USA, The Japan Society, The United Nations Association of the United States and The Americas Society. He was a former member of the Council on Foreign Relations. Smith authored Catching Lightning in a Bottle: How Merrill Lynch Revolutionized the Financial World, about the history of Merrill Lynch, which became available on December 5, 2013, the fifth anniversary of the final Merrill Lynch shareholder meeting. He married twice. His first marriage was to Maggie Smith, and they have four children and seven grandchildren. His eldest child, Heather Smith Winkelmann, is managing director of sister properties Pitcher Inn and Winvian, in Litchfield, Connecticut. The latter property was purchased by Smith's parents, Win and Vivian, in 1948, and named Winvian, after their combined names; then later expanded into a boutique hotel by Smith and his wife, Maggie who is full owner. He is currently married to Lili Ruane, the daughter of investment professional William J. Ruane and the sister of Boston music impresario Billy Ruane, both deceased. She has four daughters of her own. His stepfather was Charles B. McVay, the Captain of the Indianapolis. A recent book entitled The Indianapolis: The True Story of the Worst Sea Disaster in the U.S. Naval History and the Fifty-Year Fight to Exonerate an Innocent Man, by Lynn Vincent and Sara Vladic, recounts the tragic story of The Indianapolis and the disgraceful treatment of Captain McVay by the U.S. Navy in 1945.
