Entrepreneur and Philanthropist Bill Cummings Speaks at Wentworth

January 30, 2019

Joyce and Bill Cummings


Just outside of his family’s one-bedroom apartment above a liquor store, an enterprising young boy named Bill Cummings once gathered bottles of soda in his wagon to sell at a neighborhood construction site. From those humble beginnings, Cummings would become a highly successful entrepreneur and philanthropist, a story that he shared with the Wentworth community Feb. 5.

Cummings recounts that his parents told him to “get ahead” in life. At six years old he noticed construction workers laboring away in the sun and found a way to refresh them with the sodas he sold. He did that all summer, also selling ice cream and lemonade, and fueling an entrepreneurial spirit within him. As an adult, Cummings would found Boston real estate company Cummings Properties and establish one of the largest charitable foundations in New England.

“Life is mostly what we make of the opportunities that come our way,” he writes in his new memoir, Starting Small and Making It Big. Cummings is what most people would deem the American Dream, a Horatio Alger story that began in the Great Depression and ended with billionaire status.

Throughout his life, Cummings has demonstrated entrepreneurial qualities; from selling bottles of sodas to sweeping bullets at a rifle range as a way to sell lead to a recycling plant as an ROTC Air Force Student at Tufts University, Cummings has grown up making the most of even an inkling of opportunity. At the same time, he made sure to save pennies by doing jobs himself, spending money only when necessary.

Cummings used the money he made from selling his first business (which sold fruit punch to colleges and universities) to delve into his real passion: real estate. His company Cummings Properties built and restored more than 10 million square feet of commercial structures. But Cummings spent less time thinking of ways to make more money and more time thinking of ways to give it away. He and his wife Joyce established the Cummings Foundation in 1986, through which they have gradually contributed $2 billion of their assets.

 “They’ve almost behaved as if the money really wasn’t theirs from the very beginning,” former Tufts University President and Incumbent Harvard University President Lawrence Bacow told the Boston Globe in a 2011 article.

Bill and Joyce earned a spot on the Forbes list of the Top 50 Givers for 2018.


--Sarah Sherard

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