Leadership Giving Officer Values His Life-Changing Role

Growing up in West Point, Virginia, on the small peninsula where the Pamunkey and Mattaponi Rivers converge to form the York, Jason Chestnutt developed an early passion for biology. Even now, he’d rather read a science textbook than a novel, and he loves National Geographic.
When he graduated from the University of Virginia with a degree in biology in 1998, however, the booming stock market lured Jason from a career in science to the world of finance. At the time, financial planning was the purview of big institutions, but it would soon become a critical tool for individuals and small businesses. For Jason, that shift spawned nearly a decade of work as a financial advisor at Morgan Stanley and Merrill Lynch in Atlanta.
A Certified Financial Planner, Jason now serves as Collegiate’s leadership giving officer and director of planned giving. He started last July, along with Head of School Penny Evins and Middle School Head Tung Trinh.
“It feels good,” he said. “I’m meeting the team, and they love this place. They treat donors right, they treat each other right. It’s great to be part of a community that takes care of people who dedicate their lives to something.”
Jason is a member of an unofficial but growing club of faculty and staff who have “married in” to the Collegiate family. His wife, Amy Koonce Chestnutt, graduated from Collegiate in 1993. Her sister, Cara Koonce McDaniel ’90, is also an alumna, whose daughter, Ella McDaniel ’22, is a sophomore. Jason and Amy have fraternal twin boys, William and Henry, who are 4 ½ years old and hope to be Cougars soon.
For now, the twins have redirected Jason’s free time from fishing and duck hunting to playgrounds and soccer fields. Toying with numbers he also finds fun; he likes following stocks and staying current on tax laws and techniques of portfolio construction.
“I love investments,” he said. “It’s a huge hobby of mine; I don’t think of it as work.”
Keeping up with friends from West Point, Atlanta and Charlottesville is a priority, and something he’d rather do by phone than on social media.
Wishing to return to Virginia, Jason and Amy moved from Atlanta to Charlottesville in 2007. Jason pivoted from financial advising to fundraising, working at University of Virginia for six years as associate director and another six as director of gift planning.
Raised by an educator (his mother worked as a teacher, then a guidance counselor), Jason found that he enjoys educating donors about a place and its needs, and helping them navigate the process of planning gifts that align with their passions. Through estate planning, he says he gets to help people consider what values they want to leave behind, what lessons, what family stories. It’s one of the most rewarding aspects of his work.
Jason believes philanthropy can change an entire culture. “Whether it’s within a family, an institution, a nation,” he said, “when money goes from a number … to having the power to change and save lives – that’s amazing.”
At Collegiate, he hopes to continue to demystify development, and secure gifts to the School that will change lives. There’s no monetary amount that makes a gift meaningful, he says. “No one’s better than anyone else. That’s the way I was raised. If someone chooses to give the most they can give, it’s going to have impact and be gratifying to them.”
– Haley Nolde ‘92