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Starting Small and Making It Big

An Entrepreneur's Journey to Billion-Dollar Philanthropist

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"My friend Bill writes that he rejects the phrase ‘give until it hurts’ because he and his wife, Joyce, think the better advice is to ‘give until it feels good.’ It's a fitting observation from a man whose extraordinary business success is outmatched only by his deep commitment to lifting up those around him. After many conversations with Bill and Joyce, I've learned their perspective is not only compelling; it's contagious — and their warmth comes across on every page."

          – Melinda Gates, Co-Chair of the Bill & Melinda Gates Foundation

"No business school or business majors should conclude their studies without reading this book. Nor should any humanitarian, committed to charity and structural justice, not take a few hours to read this very readable, personable and memorable book. What is most amazing in this orderly, incremental life of business, joy and community spirit by Bill and his spouse, Joyce, is that you come away believing that 'the best is yet to come.'"

          – Ralph Nader, Esq., National political leader and author of Unsafe at any Speed

"Bill is a serial entrepreneur and an embodiment of the American Dream. His fascinating story is rich with lessons for aspiring entrepreneurs and for anyone interested in the role business can play in strengthening community and society."

          – Peter Drobac, MD, Director, Skoll Centre for Entrepreneurship, Saïd Business School, University of Oxford

"Bill Cummings never stopped counting his blessings, and neither did his wife. Neither did they tire of sharing these blessings with a widening circle of beneficiaries—from the Boston area to Rwanda. This refreshing memoir reminds us that starting small and making it big is best done by doggedly pursuing values, not riches."

          – Paul Farmer, MD, PhD, Founder, Partners In Health Kolokotrones University Professor, Harvard Medical School

"My reactions to the book ran the gamut. I was engaged by the historical aspects, inspired and entertained by the personal stories, brought to tears by a tragic event, instructed in leadership, business and human nature—and profoundly grateful to be in a position to take it all in."

          – Deborah Kochevar, DVM, PhD, Dean, Tufts Universi\


Bill Cummings never aspired to be a billionaire—and never acknowledged he was one until long after it happened. That’s because it is not money that motivates him, but rather the immense enjoyment he gets from building and growing successful businesses. He thrives at being an opportunist and believes that this often-misunderstood trait is one of the key characteristics of successful entrepreneurs. They see opportunities where others overlook them. And they act swiftly to adopt them before someone else does.

Although perhaps not intentionally, Bill’s parents encouraged his entrepreneurial nature by instilling in him the desire to "get ahead" and to become "somebody." His father painted houses, raising a family in a one-bedroom apartment atop a liquor store and a taxi stand on the outskirts of Boston. Bill’s mother was a neighborhood fixture, building friendships as she knocked on doors to collect coins for large charities that once operated that way.

From his parents, Bill learned the value of hard work, kindness, and fiscal responsibility. Year-round he washed windows for his neighborhood’s storekeepers, and for three summers as a young teen he sold ice cream from the back of his bike at a nearby Ford Motors assembly plant. Later he purchased and sold dozens of small boats using Boston Globe classified ads. Eventually, he built a 500-person firm near Boston with a debt-free portfolio of 11 million square feet of commercial real estate.

This fascinating self-written autobiography shares not only how he got there, but also his singular dedication to giving back to the communities and institutions so vital to his success. In Massachusetts alone, the cash donations from Cummings entities to local charities already total more than $200 million.

Through Bill’s unique voice, readers experience his achievements and adventures—including a stint at Fort Dix with Ralph Nader and, much later, meeting and working regularly with some of the world’s greatest philanthropists—as well as his setbacks and personal tragedies during the seven-decade story.

For anyone studying business, building a business, or running a business, Bill’s journey also offers keen insights, cautionary observations, and the pioneering thinking that produced great prosperity and a multibillion-dollar enterprise. For everyone else, it offers a new and engrossing twist on the classic American success story.


Author Bio: Bill Cummings

My autobiography is not a Horatio Alger story, or maybe it is a little bit. Born during the Great Depression, I grew up poor but first tried my hand at being an entrepreneur when I was six or seven years old. I sold bottles of soda pop each afternoon at a neighborhood construction site, and there are still so many similar opportunities for kids today.

A decade later, I talked my way into college, though perhaps I did not really belong there. I was able to pay all of my tuition and expenses by always working and by being forever frugal. Soon after graduation, I made a point of paying back a single $50 scholarship award by making a $50 contribution to my alma mater, and I have continued giving to the university—and many other recipients—ever since.

I became a serial entrepreneur in earnest, and then a philanthropist, after first working all over the country with two national consumer-products firms. In 1964, I spent $4,000 to purchase my first real business, a hundred-year-old manufacturer of fruit-juice-beverage bases, which I quickly expanded by providing refrigerated dispensers and drinks to several hundred colleges and universities.

With the million-dollar proceeds from the sale of that business in 1970, I founded a suburban-Boston commercial real estate firm. Cummings Properties quickly grew from one small building to a portfolio of more than 100 modern buildings today. Along the way, we accumulated uncommon wealth, much of which my wife, Joyce, and I have been actively disbursing through Cummings Foundation, which we established together in 1986.

Joyce and I were the first Massachusetts couple to join the Giving Pledge, an international philanthropic organization founded by Bill and Melinda Gates and Warren Buffet. We have been honored to receive dozens of community honors and accolades, including those from Ernst & Young, the Irish International Immigrant Center, the Archdiocese of Boston, and NAIOP, the association for the commercial real estate development industry. We have both received several honorary doctoral degrees and have three times served as college commencement speakers. In 2012, the Boston Globe named Joyce and me runners-up as Greater Bostonians of the Year.

We also received a Friend of Israel award, and Boston Business Journal named me the Real Estate Visionary of the Year in 2014. More recently, in 2017, the Greater Boston Chamber of Commerce named Joyce and me to its Academy of Distinguished Bostonians. We have lived together in Winchester, Massachusetts, for fifty years.

Sample Chapters

OUR SALEM STREET home was a one-bedroom apartment in an old three-story wooden tenement above a liquor store, a coin laundry, and a taxi stand. My sister and I shared the apartment's only bedroom, and our parents slept in the living room. I remember them often struggling to pay the $10 or $12 monthly rent.

My Dad, Gus Cummings, was considered too old for military service during World War II. He spent the war years working for Bethlehem Steel Company at Fore River Shipyard in Quincy, Massachusetts, and took great personal pride in his work: painting the interiors of destroyers and light cruisers. (more)

By accessing the sample chapters, you acknowledge that the reproduction or transmission, in any form or by any means (electronic, mechanical, photocopying, recording, or otherwise), is prohibited without the prior written permission of the copyright owner.


News & Events

Medford-raised business leader Bill Cummings releases memoir Medford Transcript – February 16, 2018
Cummings named Top Charitable Contributor in Massachusetts Woburn Advocate – September 12, 2017
From humble beginnings to multimillion-dollar donors Boston Globe – June 5, 2017
Bill Cummings, unleashed Boston Globe – June 16, 2016


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Bill Cummings’ Upcoming Public Appearances

Date Event Location
March 10, 4 PM Q&A with Bill Cummings Book Ends
559 Main Street Winchester, MA
April 25, 5:15 PM Cutler Center Thought Leadership Series Babson College, Winn Auditorium

4 Babson College Drive, Wellesley, MA

May 18, 11:30 AM Associated Industries of Massachusetts Vision Award The Westin Boston Waterfront
425 Summer Street Boston, MA
May 24, 12 PM Woburn Business Association Lunch & Learn Series TBD
Spring 2019 Skoll Center for Entrepreneurship Distinguished Speaker Series University of Oxford, England