The Boston Billionaire

Forbes profiles entrepreneur and philanthropist Rob Hale ’88, Conn’s largest benefactor

 

In 2002, Rob Hale ’88 P’20 built a 21st-century telecommunications empire on the back of 150-year-old technology: the landline. Now, while his company, Granite Communications, looks toward the future, Hale and his wife Karen Hale P’20 are giving away $1 million a week to grassroots nonprofits, Forbes reports in two daily cover stories this week. 

Forbes journalist John Hyatt profiles Hale, Boston’s second-richest entrepreneur, in an October cover story, detailing his path from Connecticut College, where he served as class president and earned a degree in history, to CEO of a company that generated $1.6 billion in sales last year and philanthropist with a reputation for “giving big.” 

“Hale’s vibe—fist bumps, small talk and self-deprecating jokes—is more back-slapping politico than aloof tycoon. He’s a big presence on New England’s philanthropy scene. He and Granite have collectively given over half a billion dollars to various hospitals, universities, schools and local charities,” Hyatt writes.

Mass. Gov. Charlie Baker, a close friend of Hale’s, told Hyatt, “There may be people [in Boston] who give more than Rob, but I would be surprised.” 

Connecticut College has benefited significantly from that generosity. Hale serves on Conn’s Board of Trustees, and he and his wife have given more than $50 million to Conn. The couple set the record for the largest gift in Conn’s history with a $20 million donation in 2015 and then broke their own record with an additional $30 million gift in 2021. 

“This College changed my life, and Karen and I believe deeply in its mission, in its innovations as a liberal arts educator and the leadership skills it builds in students,” Hale said. “More than ever, our society needs the kinds of graduates that this College helps develop, and we are honored to help do our part to stand with them. We hope others will join us.”

The Hales pledged $10 million of their gifts to create the Hale Scholarship Challenge, through which they match one-to-one—up to a total of $10 million dollars—all gifts of financial aid of $250,000 or more to boost the College’s financial aid endowment by another $20 million during the campaign. Only one year in, the fund has already turned $6 million in new scholarship gifts into $12 million. 

This year, the Hales are challenging themselves to give $52 million to 52 different nonprofits, creating endowments that sustain the organizations long-term. 

“These are great, impactful organizations, but they're on a wing and a prayer. They have no financial certainty,” Hale told Hyatt.