Hiking along Hadrian’s Wall
Walk the Long Walk, talk the long talk
Discovering resilience, ideas, connection along Hadrian’s Wall
In July 2025, Danny Briere, Ruane Family Executive Director of the Trinity Entrepreneurship Center (TEC), launched a new TEC program experiment: a rugged hike across England where long miles left room for big conversations and alumni/student engagement. TEC Entrepreneur-in-Residence Rick Cleary ’85 also took part and wrote about the journey. Read on for his recap.
Seven days. Eighty-four miles. 809,632 steps. Four people. One wall.
One long, historic wall. Hadrian’s Wall.
The Trinity Entrepreneurship Center (TEC) trek across England was more than a walk. It became a living case study in resilience, discovery, and ideas tested in real time. It wasn’t about miles, blisters, or even the Roman occupation of England and its clashes with northern tribes. It was about the spark that ignites when seasoned alumni and students power down their phones, trade screens for open skies, and spend a week heading west—on foot, together.
This long walk was about ideas exchanged, stories revealed, and lessons earned, one step at a time. The seven-day journey set the stage for what comes next: a new route, new voices, and more ideas, measured not in spreadsheets but in life’s lessons.
The Pitch
The idea surfaced in a winter planning session on campus. Danny Briere, Ruane Family Executive Director of the Trinity Entrepreneurship Center, no stranger to alpine treks, tossed out the idea half seriously: “Why not just take a walk? Not a program, not a panel, not another Zoom call. Just a long walk together. Students and alumni. See what happens.”
Recent graduate Nathan Sykes ’25 didn’t hesitate. “Some of my best Trinity moments came from conversations with alumni,” he said. “I wanted more. If that meant hiking boots and a little rain, I was in.”
Soon enough, gear lists circulated, flights were booked, an itinerary took shape, and in early July, they arrived at Segedunum near Newcastle upon Tyne in the United Kingdom. Alongside Danny, the crew included Rick Cleary ’85, start-up founder and one of TEC’s entrepreneurs-in-residence; Nathan Sykes ’25, founder of The People Company; and Noah Lenz, a young New York City start-up builder and friend of Nathan’s.
Two mentors. Two founders in the making. One live experiment.
A Walk, A Wall, A Plan
Walking Hadrian’s Wall is anything but a walk in the park. Built in AD 122 from the North Sea to the Atlantic, it remains a living, albeit craggy, path of stone and turf underfoot, ancient forts at your side and sheep-dotted hills always on the horizon. Hadrian’s Wall is more of an archaeological and heritage site than a traditional park. It’s just a really long and narrow site—84 miles (135 kilometers) from Fort Segedunum at Wallsend in the east to Fort Maia at Bowness-on-Solway in the west. It’s also a UNESCO World Heritage Site.
Day one began with clear skies, high spirits, and easy miles, passing through Newcastle along the River Tyne, all the way to Keelman’s Lodge, a charming and cozy inn attached to a welcoming pub, The Big Lamp Brewery. By day two, rhythms set in: pairs formed, stretched out, re-formed again, over and over. Unspoken rules emerged: Watch out for one another, look right (not left) at intersections, don’t let a good debate distract you in a cow pie.
By day three, the wall revealed its teeth: an ascending trail, rocky ridges, sweeping horizons, milecastles half buried by time. Bike pathways changed to pastures, and our legs started to groan on their own.
“Think this is hard today?” Danny asked. “Imagine the resilience and fortitude it took to haul those stones up these hills day after day. Every founder begins their journey with confidence. What matters is to be still building at mile 50.”
Strident Ideas
Like the trail, conversations twisted and turned: when to scale, how to break with a co-founder or investor, and constant new ideas, including virtual reality tours of Hadrian’s Wall, AI-enabled tools to help actors practice their lines, even a laser-outfitted bike accessory to let hikers ahead know a bike is coming up from behind. Conversations ranged from the philosophical—what makes an idea worth chasing and how (survivable) failure is a good teacher—to the playful—Noah describing how he trained an AI model to generate jazz riffs only to discover it preferred predictable four-chord pop. Rick shared stories of spotting opportunity in an underground storage facility and launching Iron Mountain’s digital archive. Nathan talked about the endorphins released upon hiring his first employee at The People Company.
Perhaps one of the livelier discussions: “Is art art if AI is used to create it?” Around Sycamore Gap, the trek’s halfway point, Danny said, “AI is not going away. We need to rethink everything in light of that, including possibly core definitions of art. “Disney animators use all sorts of digital tools to create animated movies today . . . do you think they consider themselves artists? I bet they do!” Nathan retorted, “Yeah, but they created those movies themselves—not had AI do it for them.” Danny ceded that point, but it started a long discussion about disruptive technologies and what AI can and can’t do.
In Sync, One Step at a Time
The group shared, debated, joked, pressed on. Each mile became a moving thought experiment.
As with gravity, weather always won. Fog swallowed landmarks, rain claimed hiking boots, wind stole easy conversation. Yet each setback carried its own quiet gift.
At Vindolanda, a major Roman fort and archaeological site, they paused over tablets where soldiers had scribbled notes about birthdays, shoe sizes, and supply shortages. “Ahh, logistics,” Nathan grinned. “It always comes back to logistics.”
Day five’s stop at Abbey Farm House became one of the trek’s highlights, with a long wooden table where strangers became companions: Oklahomans tracing ancestry, a British couple on holiday, a German biker roaming the moors. By night’s end, conversation flowed easily, proof that shared miles can turn chance encounters into lasting connections.
“A lot of the time it’s about showing up,” Danny reflected later. “People miss opportunities by turning in early or staying home because of the weather. The hardy entrepreneurs who keep showing up are the ones who get the deals.”
Zig, Zag, Repeat
By day six, the path had turned to mud, but their stride held firm. Danny shared stories of challenges past: a Caribbean airline venture tested by partner fraud, a near unicorn stalled by tough merger negotiation. “Failure is a checkpoint,” Rick reminded them. “Think of it as a signal. Sometimes it means refine the model, sometimes pivot the team, sometimes call it a day. If you listen, a signal can point you toward the next breakthrough.”
“Zig, zag, repeat,” Nathan quipped, delivering it like a breakthrough. The group cracked up, but by nightfall, the phrase had taken hold.
Finishing Strong
The final day delivered a classic Northumberland send-off: pelting rain and howling winds. Heads down, coats flapping, they trudged into Bowness-on-Solway. The upside was passing all the west-to-east hikers just starting their long journey. At the end of the wall, a weathered shack at the edge of a seaside cow-pie meadow. There was no tape to break, no brass band.
“This is it,” Danny said at the crest above the Solway. “End of the wall, and the start of—”
“Better zig-zaggin’,” Noah cut in, grinning.
The remark landed with unexpected weight. It marked a milestone: They had crossed a country, made history beside history, and now looked toward what lay ahead. At Fort Maia, the end point, the group posed for a victory photo—muddy, exhausted, but grinning ear to ear. That photo, captioned “The Other Long Walk,” now hangs in the TEC.
After the Wall
Back at the Entrepreneurship Center, Danny’s mud-caked boots took their place on the TEC trophy shelf. He thought back to that winter’s planning session and smiled. “Hypothesis validated,” he said. “Lessons measured in miles aren’t just memorable, they chart a course ahead.” Nathan went home invigorated with new ideas to expand his start-up. Noah rolled out a new AI feature built for improvisation. Rick returned to advising start-ups in the TEC orbit.
Perhaps the best billboard for the hike’s success: a trailside brainstorm turned into a marketing campaign, launched by Noah and Nathan in partnership, which generated contracts and revenue for Nathan’s venture, The People Company. Words became action.
The trek proved TEC’s purpose: Entrepreneurship isn’t just ideas and pitch decks. It’s the grit to navigate ambiguity, the empathy to lead, and the vision to turn setbacks into fuel.
Entrepreneurship at Trinity is inseparable from the liberal arts. Both demand curiosity, resilience, empathy, and the ability to see patterns others miss. Both flourish in community, not isolation, and both thrive when alumni and students engage in real, sustained dialogue.
Innovation begins with a single step,” Danny said. “A walk into the unknown. Stay with the questions. Keep moving, keep probing, until clarity not only finds you but carries you farther than you imagined.”
What’s next? Danny wants to do it again next year. New route, new and old crew, same spirit. Alumni and students side by side, testing ideas against miles, terrain, and anything nature throws their way, discovering truths that surface only when phones are silenced, boots are laced, and the horizon keeps moving.
Because sometimes big ideas don’t come from another meeting.
They come from walking the long walk.
Join us for the next long walk in summer 2026. Walk, talk, and trade hard-won lessons with students while helping map our route. To get involved, contact Danny Briere at the Entrepreneurship Center.
