Artwork for podcast Good Dirt: Conversations with Leaders in Real Estate & Beyond
Bill Cummings - Cummings Properties
Episode 114th October 2023 • Good Dirt: Conversations with Leaders in Real Estate & Beyond • Mike and Tom Greeley
00:00:00 01:05:51

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Bill Cummings is the founder and past president and chairman of Cummings Properties, one of the New England region’s most prominent private real estate investment firms. Since its founding in 1970, Cummings Properties has amassed a staggering portfolio of over 11 million square feet across 11 cities and towns north of Boston, and has built a reputation as a value-oriented, long-term holder of well-located real estate. While Bill is widely associated with this impressive collection of commercial properties (all owned debt-free), he now focuses most of his time and energy on The Cummings Foundation, the charitable juggernaut he oversees with his wife Joyce. Bill and Joyce made headlines as the first Massachusetts family to sign The Giving Pledge, a campaign started by Warren Buffet and Bill and Melinda Gates to encourage billionaires to give away at least half of their fortune to charity. Until then, the Cummings family had been largely flown under the radar, and this news led to many headlines with a “billionaire next door” theme.

Our conversation with Bill starts with his upbringing in Medford and he shares with us anecdotes of the early entrepreneurial bug which never left him. We hear about his career start in sales, his successful journey in the fruit juice business, and his first forays into the real estate investment arena.

He got his start in commercial real estate with just one small building, which he built next door to Old Medford Foods, and then led Cummings Properties' expansion into an 11 million-square-foot portfolio, now managed by more than 350 team members.

In 1986, Bill and his wife, Joyce, established Cummings Foundation, which has grown to be one of the three largest private foundations in New England. The Cummings family today is known widely for their remarkable philanthropy and dedication to improving the communities around them.

Among Bill's many honors are Real Estate Entrepreneur of the Year for New England from Ernst & Young, Edward H. Linde Public Service Award from the National Association of Industrial and Office Properties (NAIOP), and Real Estate Visionary of the Year from Boston Business Journal. He and Joyce were also inducted into the Greater Boston Chamber of Commerce's Academy of Distinguished Bostonians.

In 2020, Bill released the latest edition of his self-written memoir, Starting Small and Making It Big: An Entrepreneur's Journey to Billion-Dollar Philanthropist, which includes thoughtful reflections on the lessons he has learned about business, entrepreneurship, and philanthropy.

Bill’s incredible generosity is legendary in the Boston area, and we feel privileged to have him join us for an episode of Good Dirt.

Tom Greeley

Mike Greeley




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