Risky Routes

S2 Ep 16: The Risk that Built a Pepsi CEO with Craig Weatherup, former CEO of Pepsi North America

Craig Weatherup [https://adkcommunityfoundation.org/team-member/craig-weatherup]spent nearly 30 years at Pepsi, rising to become CEO of Pepsi-Cola North America and later Chairman and CEO of the Pepsi Bottling Group. When Pepsi offered him a role in Tokyo, he and his wife Connie made a decision that would shape the rest of their lives. They left comfortable careers, packed up their family, and moved to Japan without ever having visited the country. Then, on Craig’s very first day, he learned his boss had been fired. Two months later, he was given the job. He had 200 employees, barely spoke the language, and was trying to rebuild a business where Pepsi held just 10% market share. In this episode of Risky Routes, Craig reflects on culture shock, learning to lead through uncertainty, and why the opportunities that define your life rarely arrive with guarantees attached.

Ep 15 Climbing Mount Fuji and Escaping Comfort with Keyonna Taylor

On this episode of Risky Routes, Olivia sits down with Keyonna Taylor [https://www.linkedin.com/in/keyonnataylor/]to discuss the parallels between travel, entrepreneurship, and adaptability. Keyonna reflects on climbing Mount Fuji in Japan and how the experience mirrored the realities of business the hardest parts of a journey are often not where you expect them to be. Together, they explore agility, customer experience, and why businesses (like travelers) must constantly evolve, pivot, and stay intentional to succeed. The conversation also dives into Keyonna’s perspective on today’s “outcome-based economy” and the danger of companies becoming too comfortable.

Ep 14 How Sleeping Alone in a Danish Forest Changed Her Life with Dorte Krogh

On this episode of Risky Routes, Olivia sits down with Dorte Krogh [https://www.linkedin.com/in/dorte-krogh-52b0991/] for a conversation about fear, reinvention, nature, and the power of stepping into discomfort. Dorte shares how a lifelong fear of darkness unexpectedly led her on a transformational journey from sleeping alone in a tent during COVID lockdowns to hiking across Greenland and eventually building leadership retreats that bring executives into nature to reconnect with themselves and others. The episode explores: * Overcoming fear through small acts of courage * Why nature strips away ego and creates authentic connection * How high performers benefit from slowing down and being present * Building trust and relationships through shared challenge * The idea that it’s never too late to redesign your life around what truly fulfills you Together, Olivia and Dorte discuss how immersive travel experiences can create lasting personal and professional transformation with many participants leaving Greenland making major life changes, launching businesses, deepening friendships, or rediscovering purpose. At its core, this episode is about intuition, self-discovery, and finding the courage to build a life aligned with who you really are.

Ep 13 The Cost of Crossing Borders for Work and Family with Jennifer Sertl

On this episode of Risky Routes, Olivia sits down with Jennifer Sertl [https://www.linkedin.com/in/jennifer-sertl-922177/] for an honest conversation about ambition, identity, entrepreneurship, and family. Jennifer reflects on the emotional whiplash of flying from speaking in front of 2,000 people in Osaka, Japan to immediately stepping back into everyday family life at Lambeau Field with her children. Together, we discuss the hidden trade-offs founders and high performers face, how work can become deeply tied to identity, and why success doesn’t always look the way we think it does. The episode explores balancing career and family, redefining significance, and learning that sometimes the riskiest route is simply believing you are enough.

Ep 12: Surviving a mob in East Timor with Brett Miller

A riot, a locked gate, and a split-second decision that could have meant life or death. In this episode of Risky Routes, Brett Miller [https://www.linkedin.com/in/brettdavidmiller/] shares the story of being 23 years old and running the largest security operation in East Timor when a routine day turned into chaos. Called into a UN compound where his own guards had sparked a riot, Brett finds himself surrounded by an angry mob, weapons in hand, with no clear way out. What follows is a raw, high-stakes moment of fear, instinct, and survival. As panic sets in, Brett leans on a simple but powerful question to shift the dynamic, uncover the real issue, and ultimately defuse a situation that could have ended very differently. This episode goes beyond the adrenaline. It’s about perspective, communication, and the ability to step into someone else’s reality, even when everything in your body is telling you to run. Because sometimes, the difference between escalation and resolution comes down to whether you choose to react… or to understand.