Bill Cummings: Starting Small and Making It Big, in Real Estate and Then Philanthropy

Bill Cummings

Founder of Cummings Properties and Cummings Foundation to be Honored With the Lifetime Achievement Award for 2023

BOSTON- In recognition of both his 50-plus-year career in commercial real estate, as well as his tireless personal dedication to philanthropy, Boston Real Estate Times will honor Bill Cummings, the founder of Cummings Properties and the Cummings Foundation, to receive the 2023 Lifetime Achievement Award on Sept. 13 at Burlington Marriott Hotel in Burlington, MA, at its annual Excellence Awards Gala.

Photo: Bill Cummings, Founder of Cummings Properties & the Cummings Foundation

“I am delighted to accept this generous honor on behalf of so many great colleagues and client firms who have contributed to Cummings Properties’ success and Cummings Foundation’s legacy of giving,” said Mr. Cummings. “As much as I love buildings and construction, I have learned through my six decades in the industry how much impact commercial real estate truly has in promoting innovation, job creation, economic growth, and philanthropy.”

To buy tickets for the gala on Sept. 13 at the Burlington Marriott in Burlington, MA, please click here.

Mr. Cummings founded Cummings Properties in 1970, serving as president and, later, chairman. He currently spends most of his time on the work of the Cummings Foundation, which awards at least $30 million each year, and has awarded $500 million in total to date, to a widely diverse group of nonprofits in Massachusetts.

In 1986, Mr. Cummings and his wife, Joyce, established the 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.

They also established New Horizons, not-for-profit assisted and independent living communities in Woburn and Marlborough, Massachusetts. These communities currently provide homes for some 500 seniors.


Photo: Bill & Joyce Cummings

Bill and Joyce are a source of inspiration for all of us and Massachusetts is lucky to count them as their distinguished and most important couple.

The large majority of Cummings-managed buildings are owned by Cummings Foundation. The Cummings have gradually donated these buildings to the Foundation since its establishment, with all net income from all the firm’s real estate going directly to the Foundation.

“Bill is a self-made man. He started with nothing and built a real estate empire that is second to none. The better thing he and his wife Joyce did was to put the newfound wealth to good use,” said Desh Deshpande, MIT Corporation Life Member, Trustee and Co-Founder of the Deshpande Foundation, and Chairman of Sparta Group. “They are easily the most philanthropic couple in Massachusetts and have had a profound impact on hundreds of organizations.  Bill and Joyce are a source of inspiration for all of us and Massachusetts is lucky to count them as their distinguished and most important couple.”

Mr. Cummings grew up in Medford, MA and, in 1958, graduated from Tufts University. After holding sales positions with Vick Chemical Company of Greensboro, North Carolina (known, among other things, for Vick’s VapoRub) 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 an 11 million-square-foot portfolio, now managed by more than 350 team members. Cummings Properties has built or restored dozens of large and very large, and sometimes historic, commercial structures, totaling more than 11 million square feet. Based in Woburn, Cummings Properties currently provides business homes to some 2,000 companies and organizations.

“Over my more than 30 years with Cummings Properties, I’ve witnessed firsthand the impact Bill Cummings has had on the region’s commercial landscape,” said Cummings Properties Chairman & CEO Dennis Clarke. “The scope of his business achievements is impressive. Far more remarkable, however, is the purpose he has put them to through the unique philanthropic model he pioneered. By donating the majority of his buildings to Cummings Foundation, Bill has created an organization that both literally and figuratively builds communities.”

Photo: Joyce Cummings Center at Tufts University

Cummings’ portfolio includes more than 100 large and very large buildings, totaling 11 million square feet in 11 suburban Boston communities. It provides more than 2,000 companies with a wide range of commercial space, including first-class office, laboratory, R&D, retail, medical, and distribution space. Cummings has never engaged in selling or “flipping” properties, preferring to build and foster robust business communities as a long-term property manager.

Photo: 48 Dunham Ridge, Beverly, MA

The firm’s two landmark campuses are TradeCenter 128, a modern 600,000-square-foot business park that directly fronts Interstate 95/Route 128 in Woburn and is home to Middlesex County Superior Court; and the 2 million-square-foot Cummings Center, the North Shore’s largest office and technology campus, which serves more than 570 diverse businesses.

Among Mr. Cummings’ 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.

Photo: Bill & Joyce Cummings at Endicott College

The scope of [Bill Cummings’s] business achievements is impressive. Far more remarkable, however, is the purpose he has put them to through the unique philanthropic model he pioneered. By donating the majority of his buildings to Cummings Foundation, Bill has created an organization that both literally and figuratively builds communities.

The Cummings have received joint honorary degrees from—and in most cases, given commencement addresses at—Tufts University, Salem State University, Endicott College, Anna Maria College, Massachusetts School of Law, Merrimack College, Regis College, Roger Williams University, and UMass Amherst.

Photo: Bill Cummings, with his book ‘Starting Small and Making It Big’

In 2020, Mr. Cummings released the latest edition of his self-written memoir, “Starting Small and Making It Big: Hands-on Lessons in Entrepreneurship and Philanthropy,”, which includes thoughtful reflections on the lessons he has learned about business, entrepreneurship, and philanthropy.

As has been its hallmark for decades, Cummings Properties plans to continue its practice in the next five years of opportunistic purchasing of high-value acreage or buildings to achieve the same kind of gradual, organic growth that it has enjoyed for the past 50 years, both now and in the future.

Mr. Cummings’s highly acclaimed book about business and philanthropy is available electronically to all viewers without charge. Download an electronic version of the book at

Here is a brief Q/A with Mr. Cummings:

BOSTON REAL ESTATE TIMES: Can you provide a brief overview of your background and early life? 

BILL CUMMINGS: My earliest memories come from the immediate post-Depression days and the early days of World War II. My sister and I slept in a single bedroom in the family’s one-bedroom apartment on busy Salem Street in Medford, and my parents slept in the living room.

I attended public schools in Medford and then was able to pay my own way through Tufts University, when entrance was much easier. After graduating from Tufts in 1958, I unsuccessfully applied to Harvard Business School. Although, much later, I was featured in the Harvard Business Review as a case study (“Bill Cummings, the Cummings Way”). I have also lectured at the Harvard Business School many times. Both my wife, Joyce, and I have jointly given many commencement addresses at area colleges.

BRET: What inspired you to pursue your current field or career?  

BC: Before age 30, I built a very profitable business, manufacturing and selling concentrated fruit juice drinks in a niche market consisting of several hundred college and university food service departments from Maine through the Carolinas.

Soon after building my first commercial building to lease to others, however, I realized that the professional opportunities in real estate yielded a far more interesting future than fruit punch, as well as a very strong career path. With the income from our first three buildings, I could have comfortably retired before age 35, but the great satisfaction and enjoyment I derive from working in this industry has kept me going for 50 more years.

BRET: As a writer who recently published his first book, what was the experience of writing ‘Starting Small’ like?

BC: I wrote “Starting Small” by myself, and mostly by hand on yellow legal pads over a period of more than two years. Office staff typed most of it, but, not surprisingly, I found it extremely enjoyable to be involved with all the details of layout, cover design, pictures, printer negotiations, fulfillment, etc. It took all my spare time while at home and away on winter vacations and such as well as many hours while still working full time, both then and now.

After I self-published the book, an extended speaking program brought me to more than 100 colleges as far from Boston as University of Alabama, Duke University, and University of Global Health Equity in Rwanda, as well as at Oxford University, in London. I spoke at locations as diverse as the United Nations Headquarters in Manhattan and the Holton Rotary Club in far northern Maine, and many times at Harvard Business School. We have sold more than 20,000 copies of the book for the benefit of Cummings Foundation and have authorized many more free electronic copies via

BRET: What’s the biggest mistake business-wise you have made, and what did you learn from that?

BC: When I put this question to my bride of 57 years, she immediately replied that my biggest mistake was owning and operating Beacon Grille, a 300-seat upscale steakhouse we built directly fronting Interstate 95 in Woburn.

Using sheer willpower, I forced the restaurant to be successful, and it was lots of fun to operate (most of the time). Beacon Grille was extremely well built and offered fare that attracted both community residents and a strong business-based clientele. Although we developed an abundance of goodwill for the entire Cummings brand in greater Boston, the operation of the facility gobbled up far too much personal and professional time.

BRET: You and your wife signed the Giving Pledge in 2011. Did Bill [Gates], Melinda [Gates], and Warren [Buffett] approach you? What have been your interactions with them—and have they offered any business advice?

BC: My wife, Joyce, and I joined The Giving Pledge organization during its first year after learning about it from an accounting executive who acted as an intermediary. He was, of course, very familiar with not only the substantial funds we were accumulating but also our early philanthropic interests.

There were especially pleasant interactions and welcomes from all founders when we first joined, and certainly all three are typically present during annual meetings. Warren Buffet also specifically taught us so much about how things operated in the Republic of Rwanda, where Joyce and I were, at the time, just starting to become philanthropically active (in a proposed major project with the late Dr. Paul Farmer).

BRET: While you are well known for your philanthropy, there is often criticism of ‘billionaires’ “not doing enough” or “only engaging in philanthropy for tax breaks.” Do you believe that these people have a responsibility to do more?

BC: On this, I can speak only for myself. There are very few things more enjoyable than giving away large sums of money to worthy organizations. When Joyce and I determined that we would have far too much wealth for our needs, we formed Cummings Foundation to begin giving most of it away. And that was more than 35 years ago.

One of the most important aspects of The Giving Pledge organization has been to encourage more donors to be more public about what they are doing so as to inspire others to give in whatever ways they can.