By Taylor Jenkins

Twenty-six years ago, my uncle Peyton Jenkins (‘00) walked across the stage at Collegiate’s graduation, shook then-Head of School Keith Evans’ hand, and stepped into the world beyond North Mooreland Road. Since that moment, his path has been anything but linear. He earned his master’s degree, graduated from the University of Virginia, worked in commercial real estate, co-founded a national menswear brand, and today is helping build an AI startup. Along the way, he and his wife, Becky Arneson Jenkins, have built a family of their own: Peyton (‘31), Jack (‘34), and Robert (‘39). 

When asked about his time at Collegiate, Jenkins’ mind went straight to a fall night in 1999, under the stadium lights at the University of Richmond. The varsity soccer team was warming up for its rivalry match against St. Christopher’s when Hunter Lansing (‘00) walked out to the field, blasting Australian rock legends AC/DC through the speakers. Collegiate went on to win 5–0. “It was an incredible night,” he said. “One of those moments you never forget.”

Photo credit: Collegiate Class Notes.

But Jenkins is quick to point out that his Collegiate experience was defined by the people who surrounded him. Coaches like former Middle School Head Charlie Blair, and teachers like Neil Weiser (Upper School history), Wortie Ferrell (Middle School history teacher, advisor, and coach), Helen Obenchain (4th Grade), former Lower School Head Debbie Miller, Ginny MacKenzie (Lower School homeroom teacher), Bill Rider (Middle School math teacher and coach), and others, “were giants in my life,” he says. They were the figures who instilled in him a love of learning, competition, and mentorship; values that would follow him long after graduation.

When asked about a particular class, Jenkins hesitated for a second, smiled, and replied, “Mr. Weiser’s ‘America in the 60s.‘” The course opened his eyes to history in a way that stuck with him. It sparked a curiosity that would later influence the way he approached college, travel, and even business.

And, above everything else, it was the friendships across grades and years that remained the most important part of his Collegiate experience. “Hands down, #1,” he said, “I’m so fortunate those friendships have lasted.” 

Photo credit: Collegiate Class Notes.

After Collegiate, Jenkins attended UVA, where he majored in economics. Jenkins explained, “In retrospect, I wish I had had a mentor to guide me to be more thoughtful about my major and my studies. I defaulted to economics. I didn’t enjoy, it but felt like I needed to do something related to business. I know I’d have been a better young professional had I excelled in topics I loved.” Despite this, he spent much of his time in Charlottesville exploring classes that sparked his curiosity. He took everything from Renaissance art and theology to courses like “Thomas Jefferson the Architect,” “The Spy in Eastern Europe,” along with storytelling. These courses broadened his worldview and helped ignite in him a sense of wanderlust. 

After graduation, he took a teaching fellowship in England, his first major step into the wider world. When he returned to the United States, Jenkins moved into commercial real estate at The Bernstein Companies, following a path similar to his older brother, my father Scott Jenkins (‘94), and his eldest brother Howard Jenkins (‘92), as well as their father, L. Howard Jenkins. But he soon realized this work didn’t inspire him. So when a college friend approached him about starting a menswear brand in 2009, Jenkins explained, “I took the leap.” 

That leap became Alton Lane, a custom menswear company built on the idea of combining technology, craftsmanship, and a personalized experience. Jenkins and his co-founder had to learn everything from scratch: supply chains, fabrics, manufacturing, investors, customers, and how to open and run their own stores. Two young adults, with no background in fashion, zero experience with running a business, and the odds stacked against them, refused to give in. The challenges and obstacles only fueled their desire to succeed.

Jenkins with former President George H.W. Bush. Photo credit: Peyton Jenkins.

When asked about the greatest hardships he and his company faced, Jenkins answered, “That’s a hard question. There were so many,” but one in particular was COVID-19, since the demand for suits evaporated, and stores were forced to close. “It nearly broke our backs,” he said. “Getting to the other side was a true blessing.” Jenkins eventually stepped away from Alton Lane in 2021 as he moved into new ventures, but Alton Lane continues to operate today. When asked about what he loved most about Alton Lane, Jenkins reflected, “I was able to see the world, meet so many people, and pursue something off the beaten path.”

Today, Jenkins is beginning a new chapter in the world of artificial intelligence. His new Stealth AI startup company focuses on using AI and machine learning to help companies hire more effectively and more fairly. By using this technology, companies can analyze applications more effectively, support interviews with better insight, and make stronger and more consistent decisions. Jenkins explained: “It’s a whole new challenge in a whole new field. I love the challenge and the opportunity. And I’m so fortunate to be doing all of it with amazingly talented people.” When asked about the future of AI, Jenkins answered, “technology is moving at a pace we can’t quantify or really predict consistently, and while it has the ability to elevate individuals, schools, and businesses, it also has the ability to do the opposite.” 

The debate around AI is growing louder and louder each month. Some experts warn that rapid advances in artificial intelligence could soon automate jobs that people are dependent on for their livelihoods, raising real concerns about job security and the future of work. Others see AI as a powerful assistant that can advance humans by helping them work faster, smarter, and more creatively. 

Regarding his company’s approach to artificial intelligence, Jenkins explained they operate with one core philosophy: Just do the right thing. Jenkins remarked, “Our belief is that the best uses of AI are cases where the underlying tech enables humans who are working for the good of their school, family, business, etc., to fulfill their mission more effectively, more accurately, and at a faster pace… It helps humans see things and do things that they otherwise would not see or be able to do.” Jenkins emphasized that we should use technology to empower humans, rather than replace them. 

When he reflects on his journey, Jenkins returns again and again to the lessons he learned at Collegiate: curiosity, mentorship, friendship, and compassion. Jenkins explained that every morning he prays with his sons that they would “look out for the overlooked and misunderstood.” To him, that mindset matters everywhere, whether it’s in school, sports, social life, or the arts, because those things are really hard for so many people. His advice is simple: “See them. Let them know you do. And make them feel seen.” These small, daily actions can change people’s lives. 

Photo credit: Becky Jenkins.

Jenkins does his best to put his words into action. He volunteers to coach his son Jack’s basketball and soccer teams, where he tries to teach the same mindset he teaches at home. He is an active member at Third Church, where he serves as an elder and has taken part in mission work in Haiti. He also has remained involved in the Collegiate community, serving as president of the Alumni Association in 2025. In each of these commitments, Jenkins tries to live out the values he preaches.

25 years after walking across the stage at Collegiate, Jenkins’s path has taken him from Richmond to England, from real estate to fashion, and now into the rapidly growing world of artificial intelligence. Throughout it all, the values he learned as a Cougar have helped him propel himself and those around him forward.  

Jenkins is many things: an entrepreneur, a friend, a father, a husband, a brother, and my uncle. To me, he is also an inspiration. And throughout his life, he has shown me what it looks like to carve your own path with courage, curiosity, and heart.

Featured image courtesy of Peyton Jenkins.