scorecardresearch Skip to main content

At Cummings Properties, all share in holiday giving

Bill CummingsChris Morris for The Boston Globe

This might be the best time of the year for Bill Cummings.

His Woburn company, Cummings Properties, hands out checks to a long list of local charities starting every Thanksgiving week. The unusual part: Each of the company’s 370 employees gets to pick where a small slice of the money goes and can hand-deliver the checks.

Employees designate $1,000 donations to a charity of their choosing, or $2,000 if they’ve been with Cummings for at least 10 years. This week, the Cummings Community Giving Program will dole out $553,000 — a new record.

The real estate mogul-turned-philanthropist gets a kick out of watching his colleagues get into the annual tradition, which the company launched in 2012. Many families rope their kids into the decision-making and in the check deliveries.


“It gives them an opportunity to really feel what it’s like to be a significant donor,” Cummings says. “Most of their contributions are going to the places they know — it’s the soup kitchen their church or temple operates, it’s the day care center at the YMCA.”

Cummings knows a thing or two about what it feels like, too. His family foundation, which he founded with his wife Joyce, has awarded $256 million since its formation in the 1980s. The foundation now has $2 billion in assets, including two-thirds of the Cummings office-and-lab real estate empire, which spans more than 10 million square feet across 11 communities north of Boston. (The entire portfolio will eventually end up in the foundation’s ownership, and all profits from leasing activity go back to the foundation.)

Cummings no longer runs the day-to-day operations of the company. That is left to Dennis Clarke (chairman and CEO) and Eric Anderson (president). But he’s still involved in most major deals.

For much of the past two years, Cummings has been talking up his self-published autobiography, “Starting Small and Making It Big.” It’s a book tour that shows no sign of ending. Cummings has always enjoyed writing — he once published community newspapers — and wanted to tackle this project himself, without a ghostwriter.


His most recent stop: the Metro South Chamber of Commerce. He trekked to Brockton last Wednesday, to talk about Cummings Community Giving, among other topics. He hopes he can persuade other companies to follow his lead.

He was among the first billionaires to sign the “Giving Pledge” back in 2011, alongside the likes of Warren Buffett and Bill & Melinda Gates, to set an example for others.

“The only reason most of us joined it was to serve as an example for other people,” Cummings says. “My wife and I decided a long time ago we had far more than we were ever going to use, or that our kids could use.”

Dell invites Hub coders

It’s hard to meet with alums of the Resilient Coders boot camps at 50 Milk St. and not hear inspiring stories. Just ask Michael Dell.

The chief executive and namesake of Dell Technologies invited four Resilient Coders alums to Austin, Texas, this month for one of the company’s Dell Technologies Summits. Dell holds these events twice a year but this one was unusual because the company unveiled an ambitious slate of goals “for societal change” by 2030.

Among the targets: women would make up half of the company’s global workforce and 40 percent of its management ranks, and at least half of Dell’s products would be made from recycled or renewable materials. (David Lear, Dell’s vice president of corporate sustainability, says the company already has one of the largest corporate recycling programs in the world.)


During his keynote speech, Michael Dell pointed out the four Resilient Coders in the audience. The alums had won a Dell Technologies-sponsored contest at the HubWeek festival last month, with their concept of using blockchain technology to distribute medical records. As a result, Dell paid for their trip to Texas.

Resilient Coders is a nonprofit that accepts promising young adults of color and, within 15 weeks, turns them into skilled software engineers. Most don’t have college degrees, or previous programming skills. But they typically land good-paying jobs.

The alums who attended the Dell summit now work at EverQuote, Constant Contact, Humana, and Wayfair. Michael Dell singled out Charles De Farias, who worked as a hotel doorman as recently as January and is now a software engineer at Wayfair.

It was a proud moment for David Delmar Sentíes, founder and executive director of Resilient Coders. He didn’t even realize the alums were participating in the contest until just before it happened.

“I think it’s phenomenal,” Delmar Sentíes says. “There’s a difference between a movement and an organization: People who are not in positions of leadership find each other and do the work [and] ‘leadership’ has nothing to do with it.”

Healing for heroes

For Patricia Lewis, her company’s Vantage Heroes trips are always emotional experiences. This year was no exception. Vantage Deluxe World Travel offered free cruises along the Rhine River in Germany earlier this month to a group that included family members of several police officers who died in the line of duty.


Boston-based Vantage started the trips more than a decade ago for veterans but expanded them after the 2013 Boston Marathon bombings to include families affected by horrific circumstances. The hope is for survivors to bond with people who have been through similar situations.

This year, the beneficiaries included family members of four fallen Massachusetts officers: Sean Gannon (Yarmouth Police Department, died in 2018), Jeremiah Hurley (Boston police department, died in 1991), Alain Beauregard (Springfield police department, died in 1985), and Kevin Ambrose (Springfield police department, died in 2012). Ryan Moore of the Falmouth Police Department, shot in 2018 and forced to retire, also attended.

“It’s really amazing to see somebody open up,” says Lewis, whose husband Henry Lewis runs the company. “People came on board, they were very enclosed, but slowly and surely they opened up with each other, mending wounds, healing, laughing.”

Once foes, now friends

They say politics can make for strange bedfellows. Bill Weld and George Regan can attest to it.

Regan, you might remember, had been then-mayor Kevin White’s press secretary, in the 1980s when an ambitious US attorney by the name of Bill Weld pursued a corruption probe at City Hal l . White was never charged, but there were bad feelings all around.

Weld went on to be governor, and Regan launched his own PR shop.


Now, the two men have an intertwined interest: beating President Trump in 2020. Weld, an executive at lobbying firm ML Strategies, is challenging Trump in the Republican primary – and he’s hired Regan to get the word out.

“There’s no comparison between the brainpower of Bill Weld and Donald Trump,” Regan says. “Bill Weld speaks six languages fluently and Donald Trump has trouble with the English language.”

C’mon, George. No hard feelings from the ‘80s?

“That was then,” Regan says. “This is now. . . . Whatever happened in the past, happened in the past.”

Can’t keep a secret? Tell us. E-mail Bold Types at