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C-Suitephilanthropy

Every year, a billionaire CEO doles out $1,000 checks to local college grads—with a catch: They have to give half the money to charity

Sydney Lake
By
Sydney Lake
Sydney Lake
Associate Editor
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December 29, 2025, 10:16 AM ET
Recipients of Rob Dole's gifts have to donate half to charity.
Recipients of Rob Dole's gifts have to donate half to charity.Getty Images—Mario Tama/Getty Images

One of the best gifts you can give a recent college grad is cold, hard cash. It can serve as a launching pad for establishing themselves as an adult, equipping them to get their first apartment, start paying off those sky-high student loans, and maybe enough to get them some well-earned drinks at their favorite local watering hole. 

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And one billionaire makes that wish come true each year: Rob Hale, founder and CEO of telecommunications company Granite Communications, annually doles out $1,000 checks to local recent college graduates in Massachusetts. He’s worth about $6 billion and helms the $1.8 billion company that provides voice, data, internet, mobile, and video services for businesses and government clients. 

But these college graduates don’t just get to take the money and run. They have to pledge they’ll give at least half of it away to charity. 

“The turmoil in our country has increased the need for caring, sharing and compassion,” Hale said during a commencement address at Bridgewater State University in May. “Our community needs—needs—your help, your leadership and your empathy more than ever.”

Hale started this annual tradition in 2021, so he’s been able to see how some of his beneficiaries used their gift. His ritual began at Quincy College in 2021, and he’s also donated to students at Roxbury Community College, UMass Boston, and UMass Dartmouth. 

“These are students who are busting their butts to earn a diploma, and I am so proud to be able to support them,” Hale told Leaders Magazine in October.

One beneficiary, now 24, donated half of her cash to Northeast Arc, an organization helping individuals with disabilities.

“There were some pretty significant federal funding cuts right around the time of my graduation,” Gene Symonds told local news publication WBUR. “A lot of the people they serve, they rely on that federal funding. I really wanted to contribute to that.” Others gave back to local schools and youth organizations.

And while students can spend their remaining $500 how they choose, many use it toward paying off student loans. The cost of higher education is rapidly increasing and the average student loan balance amounts to $28,775 (public school) and $42,449 (private school), according to the Education Data Initiative. So being able to make a dent in those can be beneficial for recent grads. 

Why Hale is instilling a philanthropic habit

Hale’s motive isn’t just to get these students to donate to charities once and forget about it. Instead, he told Leaders Magazine he hopes to pass on the spirit of philanthropy.

“When you look at the backdrop of who these kids are, many of them have most likely not had the chance to do this before,” he said. 

And there’s evidence that starting to donate to charity early in one’s career can be habit-forming. A 2013 study by Jonathan Meer at Texas A&M University shows how people who give small, frequent gifts when they’re young make them more likely to keep giving—and giving more—later in life, regardless of gift size.

Connie Collingsworth, former COO and chief legal officer of the Gates Foundation, also said during Fortune’s Most Powerful Women conference in Washington, D.C. this fall role-modeling is important in instilling habits of charitable giving and financial planning.

“[If] we show [our daughters], and we talk to them about these issues, I think they will have a sea change,” Collingsworth said. “They want to listen. They want to be like the women that have independence and the power that comes from knowing what your plans are. The key to all of this really is intentional.”

Storied billionaire philanthropist MacKenzie Scott—who donated billions to charity this year alone—also said she was inspired by her college years to donate the vast majority of her wealth. Her college roommate loaned her $1,000 so she wouldn’t have to drop out, which she says inspired her pattern of philanthropic giving.

“It is these ripple effects that make imagining the power of any of our own acts of kindness impossible,” Scott wrote of giving in an Oct. 15 essay published to her Yield Giving site. “Whose generosity did I think of every time I made every one of the thousands of gifts I’ve been able to give?

“It was the local dentist who offered me free dental work when he saw me securing a broken tooth with denture glue in college. It was the college roommate who found me crying, and acted on her urge to loan me a thousand dollars to keep me from having to drop out in my sophomore year.”

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Sydney Lake
By Sydney LakeAssociate Editor
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Sydney Lake is an associate editor at Fortune, where she writes and edits news for the publication's global news desk.

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