Bill Cummings

Starting Small and Making it Big BookFounder and Charter Trustee, Cummings Properties, LLC
Local real estate magnate, philantropist, and author of "Starting Small and Making It Big: An Entrepreneur's Journey to Billion-Dollar Philanthropist".

October 2, 2018
1600, Admiral's Hall


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.

Bill’s parents—a housepainter and a homemaker—encouraged his entrepreneurial nature by instilling in him the desire to get ahead and to become “somebody.” He started small by washing windows for his neighborhood’s storekeepers and selling ice cream from the back of his bike, and then went on to build a 500-person firm near Boston with a debt-free commercial real estate portfolio of 11 million square feet.

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. Through Bill’s unique voice, readers experience his setbacks and personal tragedies during the seven-decade story as well as 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 through the Giving Pledge.