Out in the World

It’s an early morning in mid-June, the first day of a new job for Will Gallahan ’24, and he’s having trouble getting in the office. He’s at the base of Davenport & Co.’s downtown location in Richmond, but he hasn’t been given a key card yet. Excitement and apprehension build. The first day of a weeklong internship under the tutelage of alumni Will Hershey ’94, Ginny Wortham Kehlenbeck ’03 and Chris Pearson ’02. In fact, it’s his first day in any office, a big developmental moment. Outside the building, another Davenport employee happens to come by and lets him in. Then he finds his floor, greets Hershey, a Managing Director at Davenport, and he’s off to a week of firsts. 

First meetings, first strategic investment conversation, first lunch break, first Bloomberg terminal, first balance sheets. Finally stepping into that world was thrilling to him, like a fan moving from a spectator’s vantage at a baseball game to the pitcher’s mound. The experience was part of this summer’s Trailblaze, a program established by the Upper School, the Institute for Responsible Citizenship and the Alumni Association to connect students with Collegiate alumni who work in various professions. “I felt like a world opened up to me,” Will says of his internship. “To be totally immersed in the business and finance world was incredible.” 

Will had always had an interest in economics, how one moment can ripple throughout the United States and international markets. In his Junior year, his focus became more refined when he took a macroeconomics class with Rob Wedge. “Everything we learned in macroeconomics felt applicable to the real world,” Will says. “We would be learning about interest rates, and then we’d read the news and see how the Federal Reserve was treating interest rates. You learned how the economy operated in the world, and that was really exciting.” 

In the spring of 2023, students like Will submitted a Trailblaze interest form to participate and were placed with businesses and organizations that fit their potential career interests. He jumped at the opportunity, eager to learn more about the intricacies of finance. In this sense, Collegiate prepared him for the world, and now alumni were bringing him into it, creating an extension of a Collegiate education. “Getting connected with three alumni to show you the ropes of something I’m interested in was great, and I feel like you really can’t get that at most places other than Collegiate,” he says. “I became aware of so many different departments — operations, ventures, legal — that I knew very little about. I feel like I have a much better understanding of the world I want to get into after college.”

Trailblaze, then, provides space for students to explore. The program both expands and specifies students’ focus; they become more familiar with the jobs within a field and the opportunities available to them. “I was really surprised by the number of jobs within a financial firm and the alumni really helped enlighten me,” Will says. “And I’m looking forward to applying those lessons in the future.”

For the first time this year, Will is now a member of Collegiate’s Darr-Davis Investment Advisory Board, where students manage a sizable portfolio of stocks and allocate its income to support other clubs. After working at Davenport, he’s approaching his work with Darr-Davis confidently. He’s ready for another challenge, another set of firsts. “I know so much more about stocks now and what to look for in investments,” he says. “I’m really excited about what lies ahead for me.”