May 28, 2026| By Kerri Braly

Ah, the freewheeling days of youth, when the world beckons with adventure and the lure of “a really cool job.”

Such was the life Greg Koehlert (SFGI99) remembers from his twenties, a period during which he was independent and self-employed, traveling across the United States and Asia—“hustling,” as he puts it—to promote the clothing company he had started with a friend. “It seemed like a romantic job to anyone on the outside looking in,” Koehlert says. “And maybe it was.”

But he also recalls feeling an inexorable pull toward “literature, history, and the intellectual life,” and the entrepreneur eventually decided that he truly longed for the even more romantic job of teaching.

“I had an entrepreneurial spirit, but with that came a curiosity about how other people think, how they approach ideas and information,” he explains. “And I felt the best way to understand how to teach was to have the same kind of education as the people I was reading and thinking about.”

Koehlert, who earned his bachelor’s degree from College of the Atlantic in Bar Harbor, Maine, had grown up in Baltimore; St. John’s Annapolis had always been on his periphery. His mother also had a friend who attended the college. As Koehlert began searching in earnest for a graduate program that fit his ideals, St. John’s—specifically, its campus in Santa Fe—came even more clearly into focus. It ended up being his first and only choice.

Looking back, the Annapolis Graduate Institute was “the right place to go,” he reflects, thanks to its curriculum and its emphasis on shared inquiry. “To hold a book in common and still glean something very different from the other people in the room … to not be focused solely on my own efforts … I got a lot out of that,” Koehlert says. “It allowed me to grow beyond my own means, and I think that really shaped me as a teacher.”

After earning his Master of Arts in Liberal Arts, Koehlert began teaching, first in Atlanta and then in New York City, where he taught English and history to middle and high school students with non-verbal learning disability, ADHD, dyslexia, and various learning differences. “The way I approached education, even to children who had difficulties with learning, was through exploration: helping them to be comfortable with ideas that felt remote and inaccessible, to ask questions and not demand certainty,” he says. “I tried to make my classroom a place where students could deepen their understanding step by step, just as we do at St. John’s. There’s a nature to that kind of pursuit that serves everyone, in any circumstance, who is trying to learn something bigger than themselves.”

Koehlert remained in his New York-based teaching position for more than a decade before being asked to serve as head administrator for a campus the school was building in New Jersey. It was difficult work that offered a firsthand lesson in the impact of philanthropy: “I realized just how important it is for an organization to know what its financial outlook is going to be so it can develop and grow. And I started to think about how I could give St. John’s that same freedom to plan.”

Koehlert also began reflecting on what the college personally meant to him. “St. John’s was really good to me. Because of tuition assistance, I was able to pay off my debts, which weren’t overwhelming,” he says. “I’ve always appreciated that. If people hadn’t given to St. John’s before me, the college could not have been so generous, and I might not have been able to go.”

Koehlert had been making gifts to St. John’s for more than a decade, but in 2021, he formalized his commitment with a quarterly recurring donation he has sustained ever since. The sums are modest yet meaningful, and when paired with gifts from others, he says, they “add up to something big.” Koehlert also amplifies his impact on special giving days, when matching challenges are often available. More than 500 alumni and friends joined him on March 31 for the 2026 Johnnie Day of Giving; they collectively raised $134,000, including $25,000 from matching funds.

“Most people can’t give huge gifts. But I’m certain they can give small ones, and when a lot of people do what they can, it’s very meaningful to the school,” Koehlert notes—and he’s quick to add, to St. John’s tutors, who have chosen to work in a “really special place” despite the high cost of living in Annapolis and Santa Fe. “When people are willing to signify that what you are doing is important, that the choices you have made are valued,” he adds, “that gives you energy.”

Koehlert thinks that St. John’s requires this type of energy as much as it does financial support, and that it arises from an actively engaged community. “I’m doing Year of Classics for the second time, online, and it’s great,” he says, referring to the once-a-month program that, along with seasonal opportunities like Summer Classics, opens St. John’s seminars to lifelong learners. Courses like these are imbued with the Program’s traditional spirit of inquiry, helping participants develop a valuable skill in modern times.

“To learn how to hold competing ideas in your head and explore them with somebody else who is trying to come to their own understanding,” Koehlert stresses, “and to move forward, together, without trying to score points … that is what everybody in a democratic society needs to do.”

Does that mean St. John’s is especially relevant in our current social climate, as the value of liberal education is increasingly called into question? Yes, Koehlert agrees, but with one clarification: it always has been relevant.

“I would say St. John’s is relevant now, and before, and forever,” he concludes. “Because this kind of learning doesn’t flit away with the next book or idea or the next year or the next decade. It stays with you. It was the experience I needed to fulfill a dream—to be a teacher, to be a good teacher—and if your own experience means just as much to you, then help out in any way you can. Make sure the college is here for even more of us in the future.”

Visit www.sjc.edu/giving to learn more about philanthropic opportunities at St. John’s College.