Risky Routes

Long before Seth Schorr became a casino owner and entrepreneur, Steve Wynn sent him to Macau with a pretty unusual assignment: figure out how the market worked.

There were no consultant reports or market studies to rely on. Macau was essentially a black box. So Seth spent months on the ground - staying in the hotels, eating in the restaurants, talking to operators, watching customers, and collecting data himself.

That experience help...

What if having kids didn’t mean traveling less?

In this episode of Risky Routes, I sit down with Joe O’Connor, co-founder of Global Family Home Rentals, who packed up his life in Buffalo in 2022 and moved to Portugal with his wife and three-year-old daughter. What started as a leap into location-independent family life turned into more than four years of slow travel across Europe and beyond.

We talk about raising kids acr...

When Amit Brandon Kadosh started his company, he wasn’t trying to become a founder. He saw a problem (millions of dollars of food going to waste) & decided to solve it. With no technical background and no outside funding, he bootstrapped OnCourse into a multimillion-dollar business serving thousands of locations.

Then, everything changed.

Just days before returning to the US, war broke out in Israel. Amit was called back in...

When you meet someone who has built companies across aviation, oil and gas, shipbuilding, and hospitality, you expect them to have one defining story - the moment that changed everything.

So I asked Germán Efromovich exactly that.

What was the trip, the flight, or the experience that changed the way you lead?

His answer caught me off guard.

“There wasn’t one,” he said. “It was an evolution.”

The more we tal...

The future of work isn’t just changing…it’s becoming increasingly uncomfortable.

In this episode of Risky Routes, I sat down with Zara Ali to talk about why the traditional career ladder is disappearing and what replaces it. Rather than chasing certainty, Zara argues that the next generation of professionals will need to become comfortable with ambiguity, continuous learning, and creating their own opportunities i...

Elena Levine has spent the last 12 years building technology companies, helping founders bring products to market, and now raising a venture fund focused on AI and fintech. But one of the biggest lessons that shaped her leadership came during a Christmas trip home to Russia.

After missing an overnight train to see her family, Elena found herself stranded in St. Petersburg exhausted, without cash, and convinced the trip was over. The...

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 mental weight of comparing herself to e...

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 testing. What started as an exciti...

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 would happen next.

In this e...

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 challenge she remembers most had nothing to do wi...

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 learn...

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 (like travelers) must constantly ev...

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 executives into nature to reconnect with th...

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 founders and high performers face, how w...

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, with no clear way out.

What follows i...

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 escalated into something far more inten...

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 the quiet, challenging mome...

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 becoming a New York T...

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 instincts, embracing chaos, and learni...