Tom Matlack '86 still remembers the moment Wesleyan's varsity eight dropped its blades into the Connecticut River in perfect unison, and the boat surged forward, the eight oarsmen and one coxswain as one, the boat seeming to hover above the river. As captain, he learned a rule that has guided every venture since: when talented people find one rhythm, the boat moves forward smoothly.
The lesson resurfaced when, fresh from Yale School of Management, Matlack became chief financial officer of The Providence Journal. In 1994, he spun off the cable division and sold it for $1.4 billion; two years later, he took the rest of the company public at $1 billion and negotiated a $2 billion sale just ninety days later. Outsiders picture brutal 5 a.m. practices, but Matlack laughs: sessions seldom started that early, and the early alarms were far from the toughest challenge. What mattered, he says, was Coach Will Scoggins' fixation on poise. "At the starting line, we felt total focus and ease, so in negotiations that looked crushing on paper, I could stay in the zone while the other side sweated." That calm let him see angles others missed—and close deals measured in billions.
Not long after, the same calm led him to see something at Art Technology Group, an e-commerce start-up, weeks from running out of cash. Venture giants had walked away, but Matlack, seeing things with different eyes, noticed a promise they missed. He raised $2 million from friends in 1997, kept ATG alive, and watched it go public in 1999, peak at a $5 billion market cap, and later sell to Oracle for $1 billion. It remains the best raw return of his career.
ATG launched Matlack's venture capital firm Megunticook Management and, in the latter third of his career, drew Matlack into the search-fund ecosystem—backing recent top-MBA graduates who buy and run mid-size businesses. In those settings, he reminds bright yet green CEOs that "the only thing that's important is building a management team around you." The leaders who thrive, he says, are the ones who can find, recruit, train, and retain people who are way smarter than they are in each specialty, then meld that talent together through culture, mission, and shared values. "It's always about teamwork," he concludes—get everyone rowing in the same direction and the company will fly."
His view of teamwork extends to leadership. As people gain power, he warns, the instinct is to think they have all the answers. The best leaders counter that impulse with humility, listening first and serving always. He often cites Jim Collins's Good to Great, noting that enduringly successful companies are steered by servant CEOs. Authority, he says, should grow only as fast as humility.
Stories of purpose inspired The Good Men Project, launched in 2008 after Matlack and partner James Houghton collected a hundred essays on modern masculinity. Twelve made an anthology that opened conversations from Sing Sing Prison to a Hollywood stage with Mad Men creator Matt Weiner. When volunteers proposed a website, Matlack stepped back; today, the platform draws about three million readers a month.
Over the last decade, his search for ventures that blend profit and impact led him south to investments in Mexico, Guatemala, and the Dominican Republic. He has backed and mentored Yale- and Harvard business school-trained founders whose mission was to return home to make money but also help their people. His call center business in the DR and door factory in Guatemala now each employ more than a thousand people at wages several times the local norm, proof that business and community can pull in stride, and profit and purpose are not at odds. The CEOs of those successful companies don't talk about the money they have made; they talk about the smiles on the faces of the employees whose lives, along with their families, they have changed.
Matlack still signs up for what he calls "stupid-hard" challenges—hundred-mile trail runs, open-water swims, long rides—but says the real draw is returning to his roots. "As a high-school kid, I spent hours running through the woods, and at 60 I'm back on those same trails," he explains. The effort is physical, mental, and spiritual: the woods—and the long hours of ultra-running—are "kind of my church." His mind starts to get busy, then "shuts down" and opens up to the silence and beauty of his surroundings. He finishes feeling, he says, "a different person, a better person. That's why I keep doing it."
Math is his native tongue, allowing him to grasp at once the implications of a business strategy or investment. But that language is always in the service of a larger purpose. That blend of rigor and reflection shows up on his LinkedIn page, where four action words—Husband, Dad, Mentor, Adventurer—rest on a single base: Contemplative. That foundation reminds him—and anyone starting—to weigh meaning alongside money.
Matlack has led a pilot group of Wesleyan athletes this summer through his course "An Introduction to Business, Finance, and Life," in which he advises the students to think for themselves, find their voice, and get curious. If the idea of investment banking or working for a big consulting firm truly fires you up, pursue it, he says—but those paths suit only a sliver of graduates. Most will be happier and grow faster by chasing what genuinely interests them, even if that means stepping off the well-worn track.
Just as in the boat, Matlack advises that meaning in business and life is built on connection, collaboration, humility, and ultimately deepening our capacity to love. A winning boat is one where teammates love each other, just like a winning business. And success, joy, and purpose flow from that, not the other way around.
