Carving a Path to Success David Barry

A recent Walker Webcast featured an incredible conversation with David Barry, CEO of Pursuit, a hospitality and adventure company connecting people to iconic destinations. David’s leadership journey—from ski instructor to CEO—offers powerful insights into corporate culture, experiential travel, and the mindset required to build and scale world-class businesses. Here are some key takeaways from my lively conversation with David.

Leadership starts with humility

David emphasized that leadership isn’t about being above anyone else—it’s about being in the trenches alongside your team. He believes in leading by example, never hesitating to clean a room, wash dishes, or jump in where help is needed. This hands-on approach fosters a culture of mutual respect and teamwork, where every employee feels valued and empowered.

“Leadership can shine a light, and it can cast a shadow. If you keep humility in mind and remember that you’re no better than anyone else, you create a workplace where people want to be.”

Culture isn’t claimed—it’s earned

At Pursuit, culture isn’t dictated from the top down; it’s built through shared experiences and values. Their simple yet powerful mission—to connect team members, guests, and staff to iconic places through unforgettable experiences—guides every decision.

David also shared four core values that define Pursuit’s culture:

• Safety first – This applies to both guests and employees.
• Honor place – Everyone is encouraged to respect and protect the pristine destinations they operate in.
• Anticipate – His advice to his employees is to always be on your toes, ready to serve.
• Bring your best – Hold yourself accountable to excellence.

These values aren’t just slogans; they are modeled daily. “You can put words on a wall,” David said, “but if leaders don’t embody them, they aren’t real.”

Learning is a mindset, not a credential

David’s path to success wasn’t conventional. He didn’t have an Ivy League degree or a business background, but he had something more valuable: an insatiable curiosity and willingness to learn.

“If someone tells you that you can’t do something, ignore them. If you decide to learn, you can learn. I sat in a room with Harvard and Wharton grads, and I figured it out, chapter by chapter.”

His story is a testament to the power of perseverance and self-education, proving that success is built on effort, not pedigree.

Experiences create demand for more experiences

Pursuit thrives on a simple insight: when people have an incredible experience, they search for their next adventure. Whether it’s Banff, Alaska, or Iceland, the company’s network connects guests to new destinations, each delivering the same level of excellence and authenticity.

David explained that Pursuit operates with a ‘refresh, build, buy’ strategy. The company refreshes existing experiences, builds new ones, and buys iconic properties that will still be relevant 500 years from now.

Final thoughts

David Barry’s leadership style—rooted in humility, curiosity, and experience—has driven Pursuit’s growth and success. His focus on culture, team empowerment, and delivering unforgettable experiences provides a roadmap for any leader looking to build something lasting.

Want more?

As host of the Walker Webcast, I have the privilege to converse with fascinating people like David Barry every week. Subscribe to the Walker Webcast to see our upcoming guests.