Bill Cummings: Lessons and Legacy — A Worthy Path in Business and Life

We had the great pleasure of speaking with Bill Cummings, founder of Cummings Properties, a developer, owner, and operator of commercial real estate. Since its founding in 1970, Cummings Properties has grown to 11 million square feet of commercial real estate in 11 cities and towns north of Boston.

Bill’s charitable foundation has roughly $2 billion in assets. Bill and his wife Joyce are signatories of The Giving Pledge. Read their pledge letter.

Bill is also the author of the book, Starting Small and Making It Big: An Entrepreneur’s Journey to Billion-Dollar Philanthropist, published in 2018.

The interview was conducted by Alex Gilchrist, research director at MOI Global.

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Bill Cummings founded Cummings Properties in 1970, serving as president and, later, chairman. Although he is in the office most days, he currently spends more of his time on the work of Cummings Foundation.

Bill grew up in Medford and, in 1958, graduated from Tufts University. After holding sales positions with Vick’s VapoRub of Greensboro, North Carolina and Gorton’s Seafoods of Gloucester, he acquired, built up, and eventually sold Old Medford Foods, a well-established firm manufacturing fruit juice beverage bases. He got his start in commercial real estate with just one small building, which he built next door to Old Medford Foods, and then led Cummings Properties’ expansion into a 11 million-square-foot portfolio, now managed by more than 350 team members.

In 1986, Bill and his wife, Joyce, established Cummings Foundation, which has grown to be one of the three largest private foundations in New England. They were the first Massachusetts couple to join the Giving Pledge, an international philanthropic organization founded by Bill and Melinda Gates and Warren Buffett, and they have been honored to receive dozens of community accolades and honorary degrees.

Among Bill’s many honors are Real Estate Entrepreneur of the Year for New England from Ernst & Young, Edward H. Linde Public Service Award from the National Association of Industrial and Office Properties (NAIOP), and Real Estate Visionary of the Year from Boston Business Journal. He and Joyce were also inducted into the Greater Boston Chamber of Commerce’s Academy of Distinguished Bostonians.

In 2020, Bill released the latest edition of 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.