Jason Caldwell + Emily Harrington

Emily Harrington – Lessons from the Wall

Emily Harrington, one of the most accomplished climbers of her generation, took the stage and immediately drew the audience into the intensity of her journey up El Capitan’s Golden Gate route. Her story was not simply about scaling 3,000 feet of granite. It was about resilience, failure, risk, and the lessons learned when everything feels impossible.

Emily described the grueling preparation and the setbacks she endured—falls that left her battered and shaken, moments of doubt when even her body seemed to give out, and the constant mental battle to keep moving upward. “It’s the pursuit of a goal that makes you better,” she reflected, “even when you fail.” That framing set the tone: success, for her, was not defined by the summit but by what she became along the way .

She spoke candidly about fear—how it never fully goes away —and how choosing to continue in its presence is where growth occurs. At one point, she recalled the chilling aftermath of a major fall when she hit her head and nearly gave up:

“I didn’t want to do this. I had no confidence. I wanted to quit. But then another voice whispered, ‘That’s why you’re here.’”

Throughout her keynote, Emily emphasized the power of the people around her. Before showing a clip from her documentary, she read a line from her presentation slide:

“Do not underestimate the power of your own mind and the ability of others to uplift you when everything feels impossible. That trust in yourself and those you surround yourself with can be the magic that makes impossible dreams possible.”

That reminder—that resilience is not a solo act—echoed across the room.

Emily also reflected on the importance of presence, of anchoring herself in the moment rather than being overwhelmed by the scale of the climb. She described the terrifying “A5 Traverse,” where a single mistake could end her climb—and her life—but also where clarity and focus mattered most. “If it was easy,” she said, “we wouldn’t get out of it the same type of substance that we do.”

Her closing thoughts carried both vulnerability and empowerment. Now a parent, Emily acknowledged how her approach to risk has evolved. “My priorities have shifted,” she admitted. “But my passion hasn’t. I want my child to see me pursue the things I care deeply about—so that he learns to find something to care about too.”

Her keynote was not about heroism, but humanity. She left the audience with a universal truth: we are all capable of far more than we think, especially when we surround ourselves with the right people and when we remember our “why” in the darkest moments.

“Do not underestimate the power of your own mind and the ability of others to uplift you when everything feels impossible. That trust in yourself and those you surround yourself with can be the magic that makes impossible dreams possible.”

Jason Caldwell - Lessons from the Sea

Jason Caldwell, world-record-holding ocean rower and leadership coach, delivered a keynote that left the room hushed and deeply moved. Rather than recounting his fastest world-record row, Jason chose to tell the story of his first Atlantic crossing—a journey that many would label a failure, but which he described as the foundation for all his future success.

From the outset, Jason made clear that the true lesson of his story was about people and purpose, not performance. “I realized maybe for the first time,” he admitted, “that there’s a difference between the best people and the right people.” On paper, some teammates looked weaker. But in the crucible of the Atlantic, what mattered most was not raw strength, but commitment, grit, and clarity of why.

One of the most powerful moments came as Jason described teammate Tom, who had emigrated from Soviet-era Azerbaijan and carried with him a burning desire to represent the United States. Jason recalled the night Tom asked to join the team:

“On paper, he’s not the best. Quite frankly, he doesn’t have any business being on this boat. But he’s absolutely, 100% the right person.”

That distinction—choosing the right people rather than the most talented—became a thread through the entire talk.

As the race unfolded, disaster struck. One teammate fell violently seasick, another unraveled emotionally, and by day five, Jason’s carefully built team was fracturing. He told of the harrowing evacuation of two teammates, leaving only him and Tom on a boat designed for four. At that point, few believed they would even survive, let alone finish.

What followed was a storm both literal and personal. Jason described nights of rowing alone in pitch-black seas with 20- to 30-foot waves crashing over the boat, salt sores tearing at his body, and exhaustion so deep he questioned why he had ever chosen this path. “I was absolutely done,” he said. “I wished I had never suggested we stay.”

And yet, in that darkest hour, an unexpected act of leadership occurred. Tom emerged from the cabin and asked a simple, almost absurd question:

“Hey, what do you want for breakfast?”

At first, Jason was furious—he needed encouragement, not jokes. But then he realized: he was starving. That breakfast became their turning point. Sitting side by side in the middle of the Atlantic, Jason and Tom shared a hot meal, traded small stories, and for the first time in days, reconnected as teammates and friends.

From that morning on, they made a ritual: every day at 8 a.m., they ate breakfast together. Jason explained:

“It was our chance to re-answer our question ‘why’ to each other. Said another way, it was our way of re-committing to one another. Before breakfast, we were scared of failing, of dying, of letting people down. After breakfast, we became more afraid of letting each other down than anything else. And that is the most powerful human emotion you can imagine.”

Together, against all odds, the two men not only finished the race but climbed from 24th place to finish 11th, breaking the American record for a four-man crossing despite being only two. Jason described it as a paradox: their greatest “failure” had actually forged their deepest strength.

He closed with a reflection that tied his rowing to the entrepreneurial journey of those in the room:

“If you choose to give all of yourself to someone or something, you are also choosing to be changed by it. Some people don’t want to be changed—and that’s okay. But for those of us in this room, that is exactly what we’re here for. That’s the power of why, and that’s what makes impossible things possible.”