Risky Routes

Lauren Molenda , co-owner of Riveter Design , has trekked to Everest Base Camp, summited Kilimanjaro, run a marathon through the Alps, and spent years intentionally putting herself in uncomfortable situations. But one of the most important lessons she learned came from a moment when she was convinced she was failing. While trekking to Everest Base Camp, Lauren struggled with the altitude and the m...

What do you do when something feels wrong but everyone else seems convinced it’s right? In this episode of Risky Routes , I sit down with Harry Leider to discuss one of the most infamous corporate failures in recent history: Theranos. As Chief Medical Officer at Walgreens, Harry had a front-row seat to the partnership between Walgreens and Theranos as the company promised to revolutionize blood te...

Most people experience history through headlines. Christian Caryl experienced it firsthand. When Christian arrived in Iraq in August 2003, the war was technically over. The future was not. The country was in a strange in-between state. The old regime had collapsed, the new Iraq had not yet emerged, and nobody—from military leaders to journalists to ordinary Iraqis—could confidently explain what wo...

The most dangerous part of Tatiana Fofonova 's trek through Nepal wasn't the mountain. Before setting off on a year of solo travel, Tatiana (CEO and Cofounder of Koda Health ) spent months preparing herself physically and mentally for the adventure ahead. After hiking roughly 860 miles in New Zealand, she arrived in Nepal ready to tackle the legendary Gokyo Ri Three Passes Trek. But the ch...

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 Cr...

On this episode of Risky Routes, Olivia sits down with Keyonna Taylor 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...

On this episode of Risky Routes, Olivia sits down with Dorte Krogh 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 executi...

On this episode of Risky Routes, Olivia sits down with Jennifer Sertl 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 foun...

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 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,...

A $2,500 honeymoon, a one-way leap into the unknown, and a front-row seat to political upheaval. In this episode of Risky Routes , Adrian Erlinger shares the story of moving to Ukraine with his wife right after getting married armed with little more than a phone number, a few thousand dollars, and a willingness to figure things out as they went. What began as an unconventional adventure quickly es...

She spent years dreaming about climbing Kilimanjaro through setbacks, surgery, and doubt until she finally stood above the clouds. In this episode of Risky Routes , Leslie Woodward shares a deeply personal journey of resilience, healing, and perseverance as she takes on one of the world’s most iconic climbs. But the real transformation didn’t happen at the summit - it happened along the way, in th...

A 22-year-old with no plan moves to post-Soviet Moscow. What starts as a reckless, “nothing to lose” decision turns into a front-row seat to one of the most chaotic moments in modern history and nearly costs him his life. In this episode of Risky Routes , Otto Pohl shares how instinct, curiosity, and a series of borderline bad decisions led him from sleeping in a stranger’s childhood bedroom to be...

He quit his job, spent his savings, and flew to 30 cities in 30 days during a recession with no real plan beyond documenting the moment. In this episode of Risky Routes , Clark Dever shares how a spontaneous, borderline reckless idea turned into a national media story, reshaped his career, and led to unexpected opportunities that still define his path today. It’s a story about trusting your instin...

He didn’t know where he was going, what he was doing, or why he needed a medical clearance until he found himself snorkeling between tectonic plates in freezing water. In this episode of Risky Routes , Tony Coretto shares a story that starts with complete uncertainty and unfolds into a lesson in trust, adaptability, and letting go of control. What begins as a surprise birthday trip planned entirel...

What happens when a Goldman Sachs managing director trades structure for uncertainty and realizes the most important lessons didn’t come from Wall Street, but from a jungle in Thailand? In this episode of Risky Routes , I sit down with Dan Strack, COO of AMYNA Systems and a seasoned operator with decades of experience across finance, tech, and entrepreneurship. But this conversation isn’t about bo...

In this episode of Risky Routes , Olivia Goldstein sits down with Ellie Rusling , CEO and co-founder of MicroEra Power, to unpack the travel story that helped inspire the series itself. While studying abroad in Bogotá, Colombia in the late 1980s (a time marked by political unrest and cartel violence) Ellie found herself in a situation every traveler hopes to avoid. When a taxi ride suddenly veered...

What starts as a peaceful family getaway to the Ssese Islands on Lake Victoria quickly spirals into one of those travel stories that feels almost too chaotic to be real. In this episode of Risky Routes , Olivia Goldstein sits down with financial services veteran Milbert Kiggundu Bentham to unpack a journey through Uganda that included a stormy boat ride with only one life vest on board, running ou...

What do you do when you step outside a factory in rural Mexico, lose cell service, and realize you’re stranded on a highway alone, in a suit, with no clear way back? In this episode of Risky Routes , I’m joined by Rafael Campiz , a medical technology leader and civic advocate, who shares a formative travel moment from his early twenties that quietly reshaped how he approaches fear, uncertainty, an...

In this episode of Risky Routes , host Olivia Goldstein talks with her close friend Sophia Marshall about a moment that forever changed how she approaches risk, travel, and decision-making. While living and working in Italy , Sophia leaves a club late at night and realizes a man is following her. What begins as unease turns into a full sprint through steep cobblestone streets as he starts chasing...

What happens when burnout pushes you far beyond a reset and straight into the Amazon rainforest? In this episode of Risky Routes , Ron Skylstad shares a raw, unforgettable story about walking away from the grind, venturing deep into the Amazon, and confronting the limits of ambition, identity, and control. What began as an escape turned into a profound reckoning with nature, fear, and the quiet cl...

Before the company workedBefore the confidence clickedThere was a trip that changed everythingWelcome to Risky Routes - the stories of risk, travel, and becoming. Risky Routes is a short interview series about the trips that force you to grow up fast. The chaotic, uncomfortable, borderline bad-idea journeys that reshape how people think, lead, and live. Founders, operators, and leaders share the m...