Hard Work and Giving Back

Businessman Bill Cummings shares the secrets of his success and the joys of lending a helping hand in a new memoir

Bill Cummings signing his new book

What does it take to succeed in business? Hard work, always being on the lookout for opportunities, and knowing you are part of a larger community. Those are some of the lessons that William S. Cummings, A58, H06, J97P, M97P, shares in his new book Starting Small and Making it Big: An Entrepreneur’s Journey to Billion-Dollar Philanthropist.

A trustee emeritus, Cummings reflects in his memoir on an extraordinary career that began just around the corner from Tufts. He grew up in a two-family in Medford, and went gradually from early money-making enterprises like selling ice cream from the back of his bike as a kid to running Cummings Properties, a large commercial real estate firm with properties throughout the Greater Boston area.

No less important, though, for Cummings is helping make the world a better place. He and his wife, Joyce, H17, J97P, M97P, were among the first to join the world’s wealthiest people in the Giving Pledge, a commitment to dedicate the majority of their wealth to philanthropy. They focus their attention these days on bettering the world through Cummings Foundation, which has awarded grants totaling more than $200 million in Greater Boston and around the world, focusing on human services, education, health care, social justice, and education.

Tufts Now recently reached out to Cummings to talk about his memoir and how values and convictions guided not just a career, but a meaningful life.

Tufts Now: Why write this memoir, and why now?

Bill Cummings: Over the years, a number of people have suggested that I write down my thoughts on starting and running businesses, what it takes to be a successful entrepreneur, and why it’s important to give back to the local community. Now that Cummings Properties is being run by a talented and experienced senior leadership team—and has a solid succession plan—I finally felt that I had the time to start writing.

What are two or three key lessons you hope that students who aspire to a career in business or who are considering working for themselves take from the book?

In the book, I write about three key takeaways: on-the-job experience, loving what you do, and the value of community.

I think entrepreneurs should never underestimate the value of on-the-job learning, and should not blindly follow a path to an M.B.A. simply for the prestige that might come with it. While an advanced degree may be beneficial for some business owners, others will gain so much more practical knowledge—like I did—by launching their careers and actually experiencing the world of business.

As I built my early businesses, an essential resource was dedication. I loved what I was doing—opportunistically creating value and jobs—more than any financial return. Would-be entrepreneurs who launch into something merely for the money will inevitably struggle to muster the requisite commitment.

And as much as entrepreneurs might like to think they are going it alone—or that their teams are going it alone—companies do not exist in bubbles; they co-exist as part of communities. In the spirit of the saying that “a rising tide lifts all boats,” remember that money spent improving the lives of local residents will pay dividends by enhancing the entire community as a place to live, visit, and do business.

Another audience for the book is readers who appreciate a compelling personal story. You rose from modest family background in Medford, paid your way through Tufts, and achieved business success and are now a philanthropist. What do you attribute your success to?

Myriad factors contributed to my and Joyce’s success, but much is owed to the values our parents, who had lived through the Great Depression, instilled in us from a young age. Work hard. Don’t waste. Seize on good opportunities. Help your neighbors. These ideals combined with a genuine love for building things—companies, structures, teams—proved to be an excellent recipe for achievement in business and philanthropy.

You write that you first heard the word “entrepreneur” in a sophomore French class at Tufts and you remember feeling empowered by it. What was it like to be a student at Tufts, and why has the university remained a big part of your life?

I arrived at Tufts with a good amount of “street smarts” and more experience selling and negotiating than most students. The university, however, provided a tremendous base of fundamentals that supplemented the less formal—but quite valuable—business education I had been receiving, mostly from my father. Courses in writing, business law, and industrial psychology proved extremely beneficial when I entered the corporate world, and especially when I began buying and creating companies of my own.

And I cannot overlook the marvelous friendships I made at Tufts. It says a lot that, sixty years later, I still keep in touch with a number of the people who were significant in my life during those pivotal years.

I am grateful for the role Tufts played in helping to shape my career and my life, and it is an honor to now be in a position to give back so that young people today can have a similar meaningful experience.

Your father pointed you to your first company, a “funny old business,” as you call it, in West Medford that made fruit-punch concentrate. You write that he also dispensed wisdom, saying “Life is mostly what we make of the opportunities that come our way.”

It is so unfortunate that the word “opportunist” has negative connotations for many people. My father taught me that taking advantage of opportunities is really the essence of how and why businesses exist. Businesses thrive by recognizing a need as an opportunity and then filling the need.

This advice has served me well at all stages of my life. As a teen, I sold ice cream novelties from the back of my bicycle to hot, hungry factory workers. As a businessperson, I keep an eye out for properties that, once developed, will add great value to the community. And most important, after meeting a young woman during a sales call to Mass Eye and Ear Infirmary in 1965—and not being able to get her out of my mind—I drove back to Boston the same day to ask her out. I am so glad I did not let that opportunity pass me by, as Joyce and I have now been married for fifty-one wonderful years.

You and your team have taken on very complex projects that involve transforming neglected buildings and factories into modern, thriving workplaces. What gets you excited about these projects that many other developers might be reluctant to take on?

Cummings Properties has a highly successful track record of buying undervalued properties, retaining the best parts of them, and renovating them to create facilities that fill a need in the local business community. Two factors allow us to do this in situations when other developers might consider the project too risky. First, we have extensive in-house expertise, which allows us to handle such jobs more quickly and cost-effectively than other firms that would have to engage third-party vendors for design and construction.

Second, we do not feel the need to make elaborate plans and we do not necessarily need to know the endpoint before we begin. Tufts’ economics professors probably will not be happy about my admitting this, but despite starting many businesses in my life, I have never written a business plan. Once we decide to embark on a new endeavor, such as when we created Beacon Grille restaurant in Woburn, three weekly newspapers, or, more recently, Elliott Landing luxury condominiums in Beverly, we get to the work of actually building quickly. Not having a strict plan to follow allows us the freedom to adjust our course as we go—as we learn by doing and as circumstances change, as they inevitably do.

What drives your personal generosity for wide-ranging causes—from Boston to Rwanda?

Impact. It is so rewarding to know that Cummings Foundation’s grants are having a meaningful impact on real people’s lives. We do not want these funds to be drops in the bucket of bureaucracies that have endowments larger than ours. Rather, they are intended to be put to use immediately to help educate, heal, empower, or meet the most basic of needs, depending on the nonprofit. Seeing the positive changes that result from our philanthropy—and that of others—inspires us to keep giving.

Laura Ferguson can be reached at laura.ferguson@tufts.edu.

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