Starting Small and Making It Big

Hands-on Lessons in Entrepreneurship and Philanthropy

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Library of Congress number 2018941733
Paperback ISBN 978-0-692-99546-4
Hardcover ISBN 978-0-692-06407-8
E-book ISBN 978-0-9998951-1-5

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 French Gates, co-chair, Bill & Melinda Gates Foundation; founder, Pivotal Ventures; author, The Moment of Lift


“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, American political leader and consumer advocate; author, 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, co-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, DACVCP, MGBA, Dean, Tufts University


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 grants from Cummings entities awarded to local charities already total $500 million as of June 2023.

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.


Sample Chapters

Chapter 1

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.

Sometimes he would spend a week just painting the intricate interior of a major gun turret, and he always stressed to me how important it was that he did his job correctly—even when his work couldn’t be seen. Dad abhorred the waste, theft, and inefficiency he saw daily at the shipyard, and I remember him frequently telling my mother how lax the company was about workers repeatedly stealing tools and supplies by carrying them out under their coats or in their lunch boxes at the end of the day. (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.


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

Book Review...“Starting Small and Making it Big”

by Nils A. Shapiro, Boca Club News

Bill and Joyce Cummings'personal philosophy about charity is not to "give until it hurts," but to "give until it feels good." They have already given more than $200 million, and don't feel good enough yet.

Read more

Letter to the Author

by Sister Janet Eisner, Sisters of Notre Dame de Namur
former 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!

Meet Bill Cummings

by Michaela O'Shaughnessy, with contributions by Bill Cummings

As if Bill Cummings hasn't accomplished enough, he can now add book author to his long list of achievements. Bill's new book, Starting Small and Making It Big, is a true entrepreneur's blueprint designed by a man who has spent a lifetime spotting opportunity where few can see it.

Read more

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