Until last year, Boston-area billionaire Rob Hale and his wife, Karen, practiced philanthropy as billionaires often do, parceling out big donations to big organizations.

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Since 2018, they have given more than $125 million collectively to three premier medical-research institutions: Boston Children’s Hospital, Brigham and Women’s Hospital, and the Dana-Farber Cancer Institute. Each, they believe, will find disease cures. The couple also has showered more than $50 million on Connecticut College, Rob’s alma mater.

But in 2022, the Hales (No. 36) decided to try funding the minnows of the nonprofit world rather than its whales. At the year’s start, they set out to give away about $1 million a week to groups often overlooked by superwealthy philanthropists. “Our vision was: Let’s find small organizations for whom this gift is going to be truly impactful,” Rob says.

Adds Karen: “It was really trying to take these little organizations that struggle for footing and financial independence and give them some longevity and room to pursue their mission.”

A year later, the Hales have discovered a new joy in philanthropy. Giving to large organizations is satisfying, they say, but big gifts to small groups come with a special joy. “There’s more energy,” Rob says. “For these organizations, it’s life altering. The positive feedback you get is immense.”

Typically, the leaders of the groups had no idea what was coming. Some cried. “And when they cry, and you see that sincere gratitude, you cry, too,” Karen says.

Friends and Family

The Hales started this philanthropy journey from their home outside Boston in Quincy, Mass., where the company that Rob co-founded, Granite Telecommunications, is headquartered. Rob, Granite’s president and a co-owner of the Boston Celtics professional basketball franchise, has twice made the Forbes list of the 400 richest Americans. His estimated wealth: $5 billion.

When they started, the Hales met the $1-million-a-week challenge with gifts to 20 or so organizations that they already knew well. To widen the net, they researched groups, consulting with friends such as Peter Lynch, the philanthropist and former Fidelity money manager, and their three grown children.

Ultimately, the Hales gave $52 million to 75 nonprofits. Groups were mostly based in Boston or Quincy but ranged far afield as well. There was a home for individuals with intellectual disabilities. Programs to help disadvantaged youth through lacrosse and former convicts through weight lifting. And groups that build houses in the Dominican Republic and protect manatees in Florida.

As they researched organizations, the Hales discovered leaders whose organizations are their life’s work. Mel Lambert, a former intensive-care-unit nurse, started Sunshine Farm Sanctuary about an hour south of Boston to help children in group homes and foster care who’ve suffered abuse or trauma. The farm — built largely by her husband and run by volunteers who include her children and grandchildren — features miniature horses and donkeys to pet and ride, a koi pond, and a large house where they host as many as 80 children at a time for Thanksgiving and Christmas meals.

It was really trying to take these little organizations that struggle for footing and give them some room to pursue their mission.

The Hales and their daughter, Brett, a recent Boston College graduate, visited the farm before making a gift that’s enough to fund the operation for roughly 18 months, Lambert says. “They were awesome,” she says. “Just super nice.” The gift, she adds, “really helps me to continue my work and help the children to heal from trauma.”

With midsize organizations, contributions sometimes went toward a specific program. The $1 million gift to the Fish and Wildlife Foundation of Florida will cover almost half the cost of an effort to restore sea grass in manatee feeding areas.

The Hales made the gifts to many organizations as an endowment. Their $1 million contribution to the volunteer-run Kerry Jon Walker Fund, which takes underprivileged Boston high-school students on service trips to Rwanda, will spin off earnings that will roughly double its annual budget of less than $50,000. With the new revenue, the group has said it plans to launch service trips to Native American reservations.

“We have worked with many great organizations that operate on a shoestring,” Rob says. Leaders were sometimes hesitant. “They would say: ‘This is wonderful, but we don’t have an endowment.’” In those instances, the Hales would connect the organization to pro bono financial advisers.

Envelopes With $1,000

The Hales have tweaked their philanthropy before. About a decade ago, Rob told one of his staff at Granite that he would give $1,000 to charity if the employee would shave his free-range beard. That evolved into a “Saving by Shaving” annual fundraiser spearheaded by Granite that has raised nearly $47 million in nine years for disease research and patient care.

In the past two years, after delivering commencement speeches at area colleges, Rob has surprised each graduate with an envelope filled with $1,000 cash. Give half of the money, he told the gowned students, to someone or some organization that needs it more than you.

“The greatest joys that Karen and I have experienced in our life have come from giving,” he told the more than 150 graduating students at Roxbury Community College in May. “We want you to experience that.”