His autobiography is not a Horatio Alger story, or maybe it is a little bit. Born during the Great Depression, Bill 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, and there are still so many similar opportunities for kids today. He did not play sports, but had a dozen entrepreneurial ventures before he graduated from high school.
A decade later, Bill talked his way into Tufts University where he was able to pay all of his tuition and expenses by always working and by being forever frugal. Soon after graduation, he made a point of paying back a single $50 scholarship award by making a $50 contribution to his alma mater, and he has continued giving to the university–and many other recipients–ever since. Bill and his wife, Joyce, have given away more than $260 million in the last dozen years.
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, before he sold the firm for just under a million 1972 dollars.
He used the proceeds from the sale of that business to found a suburban-Boston commercial real estate firm. Cummings Properties quickly grew from one small building to a portfolio of more than 100 modern buildings today. Along the way, he accumulated uncommon wealth, much of which he, and his wife Joyce, have been actively disbursing through Cummings Foundation, which they established together in 1986.
Joyce and Bill 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 honors and accolades, including those from Ernst & Young, the Irish International Immigrant Center, the Archdiocese of Boston, and NAIOP, the association for the commercial real estate development industry. They have both received five honorary doctoral degrees and have four times served as college commencement speakers. In 2012, the Boston Globe named Joyce and Bill runners-up as Greater Bostonians of the Year.
They also received a Friend of Israel award, and Boston Business Journal named Bill the Real Estate Visionary of the Year in 2014. In 2017, the Greater Boston Chamber of Commerce named Joyce and Bill to its Academy of Distinguished Bostonians. They have lived together in Winchester, Massachusetts, for fifty-three years.
All fees earned by Bill are always paid directly to Cummings Foundation, Inc. of Woburn, Massachusetts.