Born during America’s Great Depression, Bill Cummings grew up poor, but through a series of highly successful business ventures, became one of the wealthiest individuals in Massachusetts and, more importantly, one of the most prolific philanthropists in Massachusetts history.

Cummings first tried his hand at being an entrepreneur when he was six or seven years old and all the way through high school with a dozen small (and successful) businesses. A decade later, he talked his way into Tufts University, and was able to pay all his tuition and expenses by continuously working and by being forever frugal. After graduating from college and then working all over America with two national consumer products firms, he became a serial entrepreneur in earnest.

In 1964, Cummings spent $4,000 to purchase his first real business, a hundred-year-old manufacturer of concentrated fruit-juice-beverage bases, which he quickly expanded and then sold for $1 million. With the proceeds from the sale, he founded a suburban-Boston commercial real estate firm in 1970. Cummings Properties quickly grew from one small building of 110 modern buildings today. Along the way, Cummings accumulated uncommon wealth, much of which he and his wife, Joyce, have begun actively disbursing through Cummings Foundation.

Cummings and Joyce were the first Massachusetts couple to join The Giving Pledge, an international philanthropic organization founded by Cummings and Melinda Gates and Warren Buffett. They have been honored to receive dozens of community accolades, from organizations as varied as American Red Cross, Archdiocese of Boston, The Boston Globe, Friends of Israel, Boston Business Journal, and NAIOP, the association for the commercial real estate development industry, and they have both received several honorary doctoral degrees and have four times served as college commencement speakers, and have been named to the Society of Distinguished Bostonians by the Greater Boston Chamber of Commerce.

Cummings has served as a director of Tanners National Bank, two community hospitals, the Woburn Boys and Girls Club, and as a member of many other community and professional organizations. He served as well as an elected member and chair of the Winchester Planning Board. Cummings has held appointments as a licensed real estate broker, a licensed auctioneer, and as a Justice of the Peace. He has traveled with his wife in 70 foreign lands including Zimbabwe where he swam to Devil’s Pool at the top of Victoria Falls, and in New Zealand where he bungy jumped off the Kawarau Bridge into the Kawarau River Gorge.

In 2018, Cummings released his self-written memoir, "Starting Small and Making It Big: An Entrepreneur’s Journey to Billion-Dollar Philanthropist," which includes thoughtful reflections on the lessons he has learned about business, entrepreneurship, and philanthropy. Since then, he has been booked to speak at dozens of colleges, including Harvard University, Massachusetts Institute of Technology, and Tufts University, locally. Other schools include University of Global Health Equity and University of Rwanda in Rwanda, as well as University of Oxford (England) and University of Alabama. Other talks have included keynote addresses at Boston Foundation and Associated Industries of Massachusetts, and for Forbes Magazine at the Forbes 400 Summit on Philanthropy.

Cummings and Joyce have lived together in Winchester, Massachusetts, for fifty years. They have four children and five grandchildren.

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