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Bill Cummings

Founder Cummings Properties, Founder Cummings Foundation, Author

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Bill Cummings grew up poor but first tried his hand at being an entrepreneur when he was six or seven years old. He sold bottles of soda pop each afternoon at a neighborhood construction site.

Bill became a serial entrepreneur in earnest, and then a philanthropist, after first working all over the country with two national consumer-products firms. In 1964, he spent $4,000 to purchase his first real business, a hundred-year-old manufacturer of fruit-juice-beverage bases, which he quickly expanded by providing refrigerated dispensers and drinks to several hundred colleges and universities.

With the million-dollar proceeds from the sale of that business in 1970, Bill founded a suburban- Boston commercial real estate firm. Cummings Properties quickly grew from one small building to a debt-free portfolio of more than 100 modern buildings with 10 million square feet of space and 500 employees.

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Bill Cummings - Entrepreneur, Philanthropist, Author

Bill and Joyce Cummings - Keynote at Giving Common laun ...

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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.

Bill 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, Bill 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, Bill accumulated uncommon wealth, much of which he and his wife, Joyce, have begun actively disbursing through Cummings Foundation.

Bill and Joyce were the first Massachusetts couple to join The Giving Pledge, an international philanthropic organization founded by Bill 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.

Bill 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. Bill 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, Bill 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.

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

Bill Cummings grew up poor but first tried his hand at being an entrepreneur when he was six or seven years old. He sold bottles of soda pop each afternoon at a neighborhood construction site.


Bill became a serial entrepreneur in earnest, and then a philanthropist, after first working all over the country with two national consumer-products firms. In 1964, he spent $4,000 to purchase his first real business, a hundred-year-old manufacturer of fruit-juice-beverage bases, which he quickly expanded by providing refrigerated dispensers and drinks to several hundred colleges and universities.


With the million-dollar proceeds from the sale of that business in 1970, Bill founded a suburban- Boston commercial real estate firm. Cummings Properties quickly grew from one small building to a debt-free portfolio of more than 100 modern buildings with 10 million square feet of space and 500 employees.


Entrepreneurs must focus on not only what is in front of them right now but also on what their business might become.


“Getting to yes” summarizes the creative and committed problem-solving approach that has led to his success. This requires strong analytical skills, as well as scrupulous attention to key details to avoid unforced errors. Those who are most able to “get to yes” are in a position to reinvest in themselves, their employees, and the communities to which they often owe so much – a goal to which every business should aspire.


Life can change in an instant. To the extent possible, entrepreneurs (or change to “leaders”) must prepare themselves for a business’ inevitable ups and downs by thinking through a “plan B.” Business leaders must be nimble, and they must almost always be ready to adapt to changing circumstances.


Bill has become well known for his singular dedication to giving back to the communities and institutions so vital to his success. He is known for saying, “Give until it feels good,” and he and his wife, Joyce, were the first Massachusetts couple to join the Giving Pledge.


Each year, Cummings Foundation awards $25 million in grants, with $260 million awarded to date. This level of giving earned him and Joyce a spot on the latest Forbes’ Top 50 Givers List.


Bill and Joyce were the first Massachusetts couple to join the Giving Pledge, an international philanthropic organization founded by Bill and Melinda Gates and Warren Buffet.