Information / Education

Book Review

  • October 2025
  • By Nils A. Shapiro

Starting Small and Making it Big: A Lifetime of Lessons in Entrepreneurship and Philanthropy

      Of the more than 200 books I have reviewed in this column over the past 19-plus years, this is the first that I can recall wanting to bring to your attention a second time. There are several reasons for this.

      The first, of course, is that I am confident you will find it exceptionally interesting. Secondly, if anyone you know or really care about is starting out in a career or planning to open a business, these pages are filled with so many invaluable tips for success that you will want to pass a copy along. Among the quoted excerpts on the back of this paperback, from such sources as Ralph Nader, Richard C. Ockerbloom (the retired president of the Boston Globe) and Adele Fleet Bacow (First Lady of Harvard University) are: “No business majors should conclude their studies without reading this memorable book. Nor should any humanitarian, committed to charity and structural justice … There are so many lessons in this book. I thank Bill for taking the time to document and summarize the many life and business lessons he has to share.”

      Perhaps most importantly, at a time when our nation is divided on so many issues—including those between the “haves” and the “have-nots”—this feel-good, inspiring, completely non-political autobiography will remind you of what has always made America so wonderful a land of opportunity.

      When I first reviewed this book, I had never heard of the author, Bill Cummings, a native of Massachusetts who, with his wife Joyce, spends a part of each winter at their Palm Beach County home. A mutual friend gave me a copy with no review commitment on my part. I began to skim through the first few pages and immediately enjoyed the writer’s warm and inviting style. By the time I had turned the last page I admired and respected the man enormously, and through his remarkable story felt better about the state of our nation: about the opportunities, entrepreneurship and charity that have always, to me, made America the greatest nation on Earth. My rave review reflected my feelings about the book, which has since gone through many printings as evidence of its wide appeal.

      Cummings was born during the Great Depression. He grew up in Medford, Mass., in a modest but loving family, in a one-bedroom apartment above a liquor store, a coin laundry and a taxi stand. His sister, Marion, and he slept in the bedroom, his parents in the living room. Bill’s father, Frank, was an honest, hardworking house painter who instilled in his son the lessons of thrift and value that would guide Bill’s lifelong business success.

      When young Bill received his weekly 25-cent allowance he deposited every penny in the bank. At the age of 7, when a construction crew showed up for street repairs in his neighborhood he loaded up his wagon every day with soda pop and orangeade from a grocery store at a nickel a bottle and sold it to the crew at a dime each, then deposited all of those profits in the bank, as well. At Tufts University in Boston, he helped pay his way through school by renting a patch of outdoor space and selling Christmas trees.

      In early 201l, Bill Cummings and his wife, Joyce—whom he married in 1966, and who has been his true life partner in every possible way—were invited by Bill and Melinda Gates and Warren Buffet to join their newly formed Giving Pledge, a small and exclusive group of billionaires who pledge to donate at least half their wealth to philanthropic causes.

      So typical of Bill and Joyce is the fact that when the Boston Globe announced their invitation to the Giving Pledge the news came as a shock to Bill and Joyce’s group of close friends with whom they met regularly to play Bridge card games, none of whom had the slightest idea that the Cummings couple were particularly wealthy. Indeed, when Bill’s and Joyce’s three grown children moved out to enjoy their own successful careers—one a pediatrician and none of them taking the easy path of joining the company business—the Cummingses had sold their now “empty nester” large house in favor of a smaller one.

      Upon graduating from college, Bill’s first steps took him along the more traditional path of working as a salesman for two major companies. When the opportunity arose for a promotion he knew he deserved, even though it was finally offered to him Bill felt under-appreciated and made the life-changing decision that it was time for him to start a company of his own.

      From that moment on it has been a business story no movie studio would ever accept as a script: “too good to be true; nobody would believe it.” But it is true. And it couldn’t have happened to a more deserving man. It all began in 1966 when he learned that the owner of a local company that made and distributed a fruit juice drink from a special recipe was looking to sell; he was asking $40,000. Bill offered $4,000, stuck to his price and signed the contract. The business grew dramatically when Bill came up with creative ways to increase distribution. Still in his twenties he needed a small bank loan and the bank insisted that his mother co-sign. It was the last time Bill would ever need a bank loan on his way to becoming a billionaire. When he sold the juice firm four years later—including the small office building it came with, which made it his first real estate deal—he received one million dollars from his $4,000 investment!

      Half the pages in this 260-page paperback, which contains many wonderful photos, are devoted to the business side of Bill’s career: the sure, steady growth of Cummings Properties into a major developer of more than 100 high-rise projects focused around the suburbs of Boston with millions of square feet of office, research, retail, hospital and medical, restaurant, health club, school, courtroom space—you name it, including in some cases condominiums that serve the concept of a convenient “live here and work here” environment.

      At a time in our nation when income inequality, wage stagnation and corporate-employee relations are major issues—none of which are discussed in this non-political book—Cummings Properties offers an example of what enlightened management can achieve. Bill promotes from within, naming managers and even his own successor from among those who have served his company loyally and well.

      Every Thanksgiving since 2012 each of the more than 400 full-time colleagues at Cummings Properties and New Horizons (the not-for-profit, non-sectarian assisted living facilities built by the company as a way to help senior citizens), in addition to receiving a fresh or frozen turkey, also receives $1,000 from the company to donate to a local charity of his or her choice. (That’s more than $400,000 a year.) Recipients have included schools, libraries, parent-teacher organizations, Boy and Girl Scout troops, animal shelters, and more.

      The other half of the book is devoted to the charities which have touched the hearts of Bill and Joyce Cummings, and to which they now devote most of their lives. The philanthropic Cummings Foundation they formed has to date issued grants totaling more than $600 million to young and deserving charitable causes, many of which have not yet drawn the attention of the giant philanthropic agencies … and Bill Cummings has even placed his real estate company and its profits into the foundation to ensure its ongoing philanthropy.

      Over and above all of these are Bill and Joyce’s own personal donations. Here are just several of many examples of what that means.

      When Massachusetts decreased funding for his alma mater, Tufts University’s, renowned College of Veterinary Medicine, Bill personally purchased the veterinary college for $50 million and contracted with Tufts to permanently operate the school, thereby never again having to worry about funding. It is now officially named the Cummings College of Veterinary Medicine at Tufts University.

      In 2009, after Bill and Joyce were emotionally affected by a visit to the Holocaust Museum in Jerusalem, Bill set up an interfaith Cummings/Hillel Program for Holocaust and Genocide Education and established long-term programs in this subject at two Boston colleges, each with a $1 million commitment.

      In 1994, when Bill and Joyce visited Rwanda 10 years after a genocide had swept across that African nation and resulted in the slaughter of more than 800,000 men, women and children, he committed a $15 million matching grant to establish The University of Global Health Equity, a unique three-part health sciences institution consisting of a treatment hospital, a research laboratory and a medical college, all drawing upon the best minds from Africa. (When that remarkable institution opened, I received an email from Bill with a photo of him smiling happily and a street sign, “Cummings Way,” over his shoulder. He was there to deliver the opening address, and the main street had been named after him.)

      If such a book will make you feel really wonderful—and would be a helpful and inspiring guide filled with success tips for someone you care about—and you still need one more reason to order a copy, just know that all proceeds from this book go to the Cummings Foundation fund. Copies are available from either Cummings.com/book or from Amazon.com.