Risky Routes

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 learning to stay grounded through both the highs and the crashes because the moments where you take real risks are the ones that actually stick.

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 entirely by his wife becomes a series of unknowns from a mystery destination to a physically intense experience in Iceland that pushes him far outside his comfort zone.

But beneath the adventure is a deeper insight: the same mindset that allows you to embrace uncertainty in travel is what defines great founders and operators. You make plans but you hold them loosely. You trust the people around you. And when things don’t go as expected, you adapt quickly and move forward.

Because whether in business or life, the best outcomes rarely come from having all the answers upfront. They come from being willing to step into the unknown.

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 boardrooms or balance sheets it’s about the moments that reshape how you see success.

From riding elephants through remote terrain to crossing rivers on bamboo rafts that weren’t built to last, Dan shares how a formative trip to Southeast Asia reframed everything: risk tolerance, identity, and what it really means to build a meaningful life.

We get into:

• Why the most valuable lessons come from uncomfortable, unpredictable environments

• The dangerous trap of tying your identity to your career

• What it feels like to walk away from Wall Street and build something on your own terms

• The “three jobs” framework for creating freedom and optionality

• Why entrepreneurship is less about certainty and more about figuring it out mid-journey

This episode is a reminder that sometimes the raft will fall apart and that’s exactly the point.

Because risk creates perspective. And perspective creates success.

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 off course into a deserted industrial area, Ellie had to rely on instinct, quick thinking, and the local knowledge she had picked up from friends to escape a potential kidnapping.

What follows is a gripping story of composure under pressure, the power of community, and how people often show up when you need them most. Ellie reflects on the lessons she carried forward from that moment - about calculated risk, trusting your instincts, and building networks of people who have your back.

The conversation also draws parallels between navigating uncertainty while traveling and the realities of entrepreneurship: the importance of resilience, perspective, and the courage to move forward even when things don’t go according to plan.

A wild story from Colombia becomes a powerful reminder that sometimes the most uncomfortable journeys shape us the most.

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 out of gas in the middle of the lake, a midnight bat encounter inside their hotel room, and a final escape via what Milbert describes as a “Volkswagen with wings.”

Milbert brings more than 25 years of experience in financial services, with leadership roles at Bank of America, Standard & Poor’s, and Bear Stearns, most recently focused on digital engagement for small businesses and middle-market banking. A Cornell graduate and entrepreneur who has also founded a small business in New York City, she shares how this travel experience mirrors lessons from the corporate world: trusting your instincts, doing your due diligence, understanding incentives, and knowing when to take control of a situation.

What unfolds is more than just a wild travel story. It becomes a conversation about risk, leadership, decision-making, and the importance of asking the right questions before you get on the boat both literally and metaphorically.

If you’ve ever ignored your gut while traveling or in business this episode will hit close to home.

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, and decision-making.

At just 24 years old, Rafael found himself walking for over an hour through an unfamiliar industrial corridor in Guanajuato - unknowingly the Mexican state with the highest homicide rate at the time. With no Uber, no signal, and no clear plan, he had one option: keep moving forward.

What unfolds is a story about youthful confidence, trust in the unknown, and the surprising clarity that can emerge when you stop catastrophizing and start focusing on the next step in front of you.

We talk about:

• Why fear in your mind is often worse than reality

• How uncertainty can sharpen judgment instead of paralyze it

• The difference between reckless risk and grounded optimism

• And how that experience still shapes how Rafael navigates life, leadership, and travel today

Rafael Campiz is the Vice President of Business Development at SeedMEDX, a medical technology company focused on life-saving patient monitoring solutions. With a background in biochemistry, he works at the intersection of science, business growth, and healthcare innovation.

Beyond his professional work, Rafael is deeply committed to community service. He serves on the board of the Rotary Club of Albany, where he is one of the youngest board members in the organization’s history, and is also a board member of the Albany Rotary Foundation. He actively advocates for institutional change and improved support systems for survivors of human trafficking, driven by a belief in building confidence, independence, and long-term positive impact.

This episode is a reminder that sometimes the most defining journeys aren’t planned and that growth often begins the moment you realize standing still isn’t an option.

About Rafael

Rafael Campiz is the Vice President of Business Development at SeedMEDX, a medical technology company focused on life-saving patient monitoring solutions. With a background in biochemistry, he works at the intersection of science, business growth, and healthcare innovation.

Beyond his professional work, Rafael is deeply committed to community service. He serves on the board of the Rotary Club of Albany, where he is one of the youngest board members in the organization’s history, and is also a board member of the Albany Rotary Foundation. He actively advocates for institutional change and improved support systems for survivors of human trafficking, driven by a belief in building confidence, independence, and long-term positive impact.

This episode is a reminder that sometimes the most defining journeys aren’t planned and that growth often begins the moment you realize standing still isn’t an option.

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 her.

Rather than letting fear shrink her world, the experience becomes a source of confidence.

Sophia reflects on how that night taught her to:

• Trust her instincts under pressure

• Ask for help without hesitation

• Stay calm and adaptable when plans collapse

• Move through unfamiliar places with awareness not fear

Now a community builder and startup ecosystem operator working closely with founders and investors, Sophia connects this experience to the way she leads, plans, and executes in high-stakes environments today.

Risky Routes tells stories of travel moments that force growth where discomfort creates perspective, and perspective creates confidence.

🎧 New episodes explore risk, resilience, and the journeys that shape how we show up in our lives and careers.

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 clarity that only comes when everything familiar falls away.

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 moments when risk created perspective and perspective changed everything.New episodes coming soon!