Entrepreneurial Workshops and Speaker Events

The Cummings Way: Fireside Chat With Bill Cummings

Bill Cummings, A58, H06, J97P, M97P, a successful real estate entrepreneur and renowned philanthropist, returned to Tufts to chat with students and alumni in November 2023. Bill is the founder of Cummings Properties. In 1986, Bill and Joyce Cummings 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. The fireside chat was moderated by Professor Usha Pasi of Tufts University.

Q&A with Bill Cummings

Where does your philanthropic mindset come from? How do you stay so grounded while achieving business success?

Joyce and I were both raised by parents who believed in giving back to the community. In those days, the amounts our families gave were dramatically smaller, but the thought and care behind those acts were no less significant.

As regards staying grounded, we try to surround ourselves with people who share our values. In many cases, we have known these individuals for decades. For example, our kids attended the same elementary school, or we have worked alongside each other at Cummings Properties for many years.

What principles/values guided your development and growth as a man?

Very much a product of the Great Depression, I learned the importance of frugality, hard work, and saving money from a young age. These characteristics have been integral to the success of Cummings Properties. My dad taught me to always be on the lookout for opportunities and to act quickly when they presented themselves.

When you met your wife, how did you know that she was the one for you? As a high-performing, highly ambitious individual. How did she align with your goals.

Fortunately, we each aligned with the other’s goals.

There is a saying: “Show me a great man that is a son of a great man.” You have kids. How did you raise them to ensure they share your ambition and passion?

Above all, Joyce and I tried to raise kids who would be good citizens and would be happy. None of them have chosen the entrepreneurial path, yet they are all doing something they find rewarding. Watching them create happy, full lives of their own has been a source of great joy.

Do your children work for you? Are they in the same business?

Some of our four children have worked in our real estate and senior living organizations in the past. Although I would have loved for one or more of them to take over the family business one day, Joyce and I are proud that they have followed their owns paths.

What do you believe are the important entrepreneurial qualities kids today should have to succeed in the current economy?

Hard work, risk-taking, and long hours pretty much define entrepreneurship, along with leadership abilities, and surrounding oneself with other smart people who crave being part of a successful and worthwhile firm. Entrepreneurs must lead by example and truly be available with an open mind each time there are jobs to be done, including the less attractive ones. They must be constantly looking for and thinking of ways to make their company or another venture better and stronger.

How do you define the impact of the Cummings Foundation?

Cummings Foundation has awarded more than half a billion dollars to date in greater Boston. To some extent, its impact is defined by the effectiveness of the nonprofits it funds. Beyond this, however, we have been delighted to see our “democratized” model spread the spirit of philanthropy. By really involving hundreds of community members in deciding where funds will go, these individuals learn more about the needs of the community and the nonprofits meeting them. They often tell family and friends about what they learn, and many of our volunteers have made donations of their own to organizations that resonated with them.

How do you make sure the money you donate is used for its intended purpose?

Grant recipients provide brief annual impact reports describing how the funds were used and any variances, challenges, or major organizational changes. Our volunteers also conduct annual site visits with most grantees, allowing us to stay connected and apprised as they evolve to meet the needs of those they serve.

Do you think scalability is important for nonprofits? Are multi-national nonprofits more or less effective than small local nonprofits?

That would certainly depend on innumerable factors, including the organization’s mission. Hyperlocal nonprofits can often capitalize on relationships to gain the momentum and support necessary to successfully address a specific community need.

On the other hand, when addressing issues that are widespread, a nonprofit with a proven history of success and a strong leadership team could be quite effective in adapting and scaling its programs for the benefit of a much larger population. 

Any cautionary advice to a foundation interested in starting participatory grant making?

Be clear with your volunteers not only about your funding priorities but also your mindset. It can be easy to approach the process with the intent to judge, playing into the power dynamic inherent between those seeking funds and those with funds to give. At Cummings, we view the nonprofits as the experts, and we seek to learn from them. Respect and gratitude are at the forefront of our decision-making process.

How does the Cummings Foundation view the situations in Congo and Israel/Gaza and what strategies are needed to aid/revolve these conflicts?

We are careful at the Cummings organization not to purport to be experts beyond our core business, real estate. Even when it comes to philanthropy, we effectively outsource the decision-making to the real experts: a diverse group of local community leaders.

Although it would be presumptuous of us to recommend strategies to resolve complex international conflicts, we stand on the side of peace and hope that diplomacy will lead to an easing of tensions and greater understanding and respect for all humankind.