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Starting Small and Making It Big

An Entrepreneur's Journey to Billion-Dollar Philanthropist

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Cover Praise

“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 Jamie’s death, 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 University

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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.


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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.

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Sample Chapters

Chapter 1

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. (Read 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.

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Here is what readers are saying about this engrossing story of how a local youth became an extraordinary success and is now giving back in a major way.

Doing What's Right

by Heather Lauten, Esq.

Today's corporate temperament prizes decisions made on the basis of a simple opportunistic edict: do what will produce the greatest revenue while consuming the fewest resources. There's nothing wrong with that thinking, per se, but there's a vital piece missing from those broad strokes: doing what's right.

Read more

This value system (not to mention our current political discourse) has clouded the confluence between opportunity and opportunism, promoting thinking in which the latter is the province of the prosperous and the former describes a concept that people feel has escaped them. What remains is a society in which too many believe they're helpless to effect change, compelling children to march for their lives in Washington in the face of public apathy, and allowing the civic void to be filled by those who mask intolerance and ignorance by calling it innovation.

In his new memoir, "Starting Small and Making It Big: An Entrepreneur's Journey to Billion-Dollar Philanthropist," Bill Cummings offers a welcome rejoinder to this diminished thinking, showing us not only that hard work and diligence can lead to success but also that success can foment fundamental justice and genuine structural change along the way.

When Cummings first went into business for himself, negotiating a good deal to purchase a hundred-year-old beverage enterprise in 1964, his dad gave him some advice about opportunity that stuck with him: "The most important thing about being lucky," he said, "is recognizing good luck when it comes along, and then taking advantage of it. Life is mostly what we make of the opportunities that come our way."

"Starting Small" details Cummings' story of how, with a practical sensibility and belief in himself and others, along with an eye for making his own luck, he worked his way from conventional working-class beginnings to founding a real estate company with a portfolio of more than 11 million square feet of debt-free space in his totally unleveraged style.

What makes Cummings' self-made-man narrative unique, and worthy of attention, though, is the rest of the story. With the kind of detailed guidance that budding entrepreneurs will earmark for reference, and the charming conversational tone of a man who enjoys telling a tale, Cummings' book describes not only the life he and his wife, Joyce, have created by making the most of the opportunities that have come their way, but also how they have become philanthropists on a scale few accomplish, having already given more than a billion dollars to charitable causes.

Members of the Giving Pledge, established by Warren Buffett and Bill and Melinda Gates, Cummings attributes his and Joyce's extraordinary dedication to giving back to their community—to institutions large and, mostly, small—to what he describes as their "belief in the goodness of all humanity."

That strong-held belief, Cummings illustrates from the beginning of "Starting Small," comes from his and Joyce's strong family backgrounds, and life-long association with like-minded people who shared their values and supported their endeavors, but it's also clear that Cummings genuinely likes people and has the gift to recognize their best qualities.

"At Cummings Properties, one of our major goals is to find out what good employees do best and then keep them busy doing it," Cummings writes. In "Starting Small," Cummings paints convivial portraits of his colleagues, many of whom have long tenures with his company, the average length of service for the 360-person firm being more than 11 years.

On the occasion of one colleague's 40th anniversary of service with the company, Cummings describes how equipment operator George Holland received not only an engraved rocking chair celebrating the milestone, but was shocked to be handed the keys to the company's first brand-new backhoe, which had his name painted prominently on the door.

Other stories are tender, and at the heart of the book is a tragedy, when Cummings' protégé, 41-year-old Jamie McKeown, was stricken by a fatal heart attack. Cummings' account of his more than 17 years spent mentoring Jamie, and his profound pleasure in having cultivated a person who cared as much about improving his community as he did about growing a company, explains how the loss served as a sort of turning point for Cummings' altruistic views.

In describing Jamie at his funeral service, Cummings said "no man I have ever met cared more about doing the right thing," and that Jamie "led by example." Cummings writes, "Although Joyce and I had formed Cummings Foundation 10 years before Jamie died, his death was a stark reminder to me that if she and I were to do meaningful good things, together with the foundation, we really needed to get started."

Doing the right thing, leading by example, and incorporating charitable giving into every aspect of his immensely successful business is how Bill Cummings has honored Jamie and others who have impacted his and Joyce's thinking, some on a grand scale, and many, many others on a small, local level. In some ways, "Starting Small" is a textbook on how—and why—to give, as individuals, and, importantly, as an integral part of the corporate culture.

Ms. Lauten, an attorney, is a member of the Cummings Properties team.



Big Things Can Start Small

by Deirdre Sartorelli, Director,
Angle Center for Entrepreneurship, Endicott College

It's easy, when making plans for goals, to get caught up in the lofty. Well, let me be more specific...lofty goals are fine. It's just been my experience that the lofty goals are reached in incremental small steps. By breaking it down, important things can be achieved.

Read more


Sister Janet Eisner, Sisters of Notre Dame
President, Emmanuel College

Yours is a fascinating account, full of valuable lessons for readers ranging from aspiring entrepreneurs to experienced managers. Yet the book's appeal reaches far beyond the business world. In your reflections about relationships, principles, and the nature of success, you offer wisdom that will benefit people in all walks of life. I certainly recognized many of the names noted in the book and I felt resonance with the struggles and joys of leading an organization in Boston over the past several decades.

I have recommended your memoir to our faculty for discussion with our students, particularly our management students. I am sure these conversations will be most engaging.

Congratulations on another major accomplishment!


The Cummings Connection: A Modern Philanthropist with Echoes of Franklin and Carnegie

by Chris Morss

Unlike the other framers of the Constitution, Benjamin Franklin grew up poor, as did steel magnate Andrew Carnegie. Through shrewdness and hard work, both accumulated substantial fortunes. In 1790, Benjamin Franklin left a legacy to the citizens of Boston that Andrew Carnegie matched in 1906, leading to the founding of today's Benjamin Franklin Institute of Technology. Mr. Carnegie accumulated a far greater fortune than he could ever use and sought—albeit unsuccessfully—to give it all away before he died.

Read more

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News & Events

Real Estate Billionaire Bill Cummings Is Giving It All Away 90.9 WBUR / NPR, Boston – May 8, 2018
Cummings Foundation Donates $10M To Boston Area Nonprofits WBZ Channel 4 News, Boston – April 20, 2018
Bill Cummings' appearance on "Nightside with Dan Rea" WBZ AM 1030 Radio podcast – April 17, 2018
Bill Cummings on "Greater Boston" with Jim Braude WGBH channel 2, Boston – April 14, 2018
Singer Island resident known for real estate, philanthropy pens first book Palm Beach Post – April 9, 2018
Bill Cummings on "Off the Shelf" with Veronica Andrews Danvers Community Access Television – April 6, 2018
Philanthropist discusses importance of social responsibility NECN Business – April 4, 2018
Hard Work and Giving Back Tufts Now – April 4, 2018
Philanthropist Bill Cummings adds a new title to his portfolio: author The Boston Globe – March 20, 2018
Cummings draws standing-room-only crowd to first book event in Winchester Cummings Properties Blog – March 20, 2018
A foundation for giving: how this real estate mogul has built his philanthropy Inside Philanthropy – March 18, 2018
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


Bill Cummings’ Upcoming Personal Appearances

Last updated May 7, 2018 with the most current information available.

Date Event Location
May 24, 2018,
12:00 PM
Woburn Business Association
Lunch & Learn Series

300 Trade Center
Suite 5550, Woburn, MA

May 31, 2018 The Giving Pledge  
June 6, 2018,
12:00 PM
Medford High School Graduation
Commencement Speaker

Tufts Gantcher Center
161 College Ave
Medford, MA

June 12, 2018,
6:30 PM
Woburn Historical Society
"Transforming Woburn into the 21st Century"
Woburn Memorial High School
88 Montvale Avenue, Woburn, MA
June 13, 2018 The Philanthropy Connection
Distinguished Speaker
June 20, 2018 Bentley University Alumni Summit Keynote Speaker:
"An Afternoon Focus On Entrepreneurship"
LaCava Center
175 Forest St, North Waltham, MA
June 20, 2018 Merrill Lynch
After Hours Event
June 26, 2018
5:30 PM to 7:30 PM
Dimock President's Council Reception
Conversation hosted by WBUR's GM Charlie Kravetz
Eastern Bank, Boston
June 27, 2018 New Horizons at Marlborough
Book Talk
New Horizons at Marlborough
June 28, 2018
3:00 PM to 5:00 PM
Cummings Center
Meet Founder and Author Bill Cummings
Community Conference Room
100 Cummings Center, Beverly
July 10, 2018
7:30 AM to 9:00 AM
McLane Middleton
Guest speaker
300 Trade Center, Woburn
Suite 7600
September 2018 Mass Maritime Academy
Distinguished Speaker
September 18, 2018
7:00 PM
Medford Public Library
"Starting Small and Making It Big"
111 High Street
Medford, MA
September 20, 2018 The Jenks Center
"Bill Cummings Presents: Starting Small and Making It Big"
Winchester Jenks Center
109 Skillings Rd, Winchester, MA
October 9, 2018 Westford Business Association
Distinguished Speaker
October 19, 2018

Tufts University
Founders Workshop Keynote Speaker

419 Boston Ave
Medford, MA

Fall 2018 Boston College
Carroll School of Management Speaker Series
Spring 2019 Skoll Center for Entrepreneurship
Distinguished Speaker Series
University of Oxford, England

Prior Appearances


Date Event Location
March 10, 2018 Author Event at Book Ends bookstore Winchester, MA
April 4, 2018 and
April 5, 2018
Tufts Entrepreneurship Leadership Program Awards Ceremony Tufts University
April 4, 2018 NECN Business with Brian Burnell

New England Cable News

April 6, 2018 "Off the Shelf" with host Veronica Andrews

Danvers Community Access TV broadcast

April 17, 2018 "Nightside with Dan Rea" on WBZ AM 1030 Radio WBZ AM 1030 Radio podcast
April 20, 2018 WBZ-TV Channel 4 News feature WBZ-TV Channel 4 broadcast
April 24, 2018 "Greater Boston" with host Jim Braude WGBH Channel 2 broadcast
April 25, 2018 Babson College: Cutler Center Thought Leadership Series:
Babson College - Olin Hall
May 1, 2018 WBZ AM 1030 Radio news coverage

WBZ AM 1030

May 14, 2018 Anna Maria College
Bill and Joyce Cummings accepting honorary degrees
Hanover Theatre, Worcester, MA
May 18, 2018 Associated Industries of Massachusetts
Vision Award
The Westin Boston Waterfront

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