Risky Routes

Kimberly Trueba has built a career around one core idea: the environments we create shape how people think, feel, and lead.Today, she is the CEO of Girl Scouts of Southern Nevada. Before that, she spent more than a decade at Walt Disney Imagineering, then went on to build a design firm working on hospitality and lifestyle projects around the world.In this episode of Risky Routes, Kimberly shares how those experiences shaped her approach to leadership, decision-making, creativity, and risk.We talk about the question that helped open the door to Disney, what she learned from working alongside world-class architects and designers, and why some of her most valuable leadership lessons came from simply observing people and understanding how they experience a space.Kimberly also shares how working across different countries and cultures expanded the way she thinks about experience design, why curiosity remains one of the most important qualities for any leader, and how she carried those lessons into her work with Girl Scouts of Southern Nevada.We also get into confidence, taking calculated risks, building a personal board of directors, creating opportunities for the next generation, and why exposure to new people, places, and experiences can fundamentally expand what someone believes is possible.It’s a conversation about leadership, creativity, and the experiences that shape the way we see the world.

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 helped shape how he approaches business today: don't assume you understand a market. Go learn it.Seth went on to co-found Fifth Street Gaming and today serves as Chairman of the Downtown Grand Hotel & Casino in Las Vegas. His career has also put him unusually early to several major shifts in gaming—from attempting to build online gaming with Steve Wynn around 2000, to esports, sports betting, and now AI.Not every bet worked. Some were simply too early.We also talk about buying his first casino just as the 2008 financial crisis hit and watching revenues fall 60%, why he thinks young founders may be too quick to skip the experience of working inside established organizations, and why founders should be very careful about whose money they take.And, of course, I had to ask a lifelong Las Vegas casino operator his favorite game.Spoiler: we agree. 🎲

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 across different cultures, the challenges of building community on the road, and why Joe and his wife think about life in seasons rather than permanent decisions. We also get into how their experience helping hundreds of traveling families led them to launch Global Family Home Rentals, an invite-only community built specifically for families who want to live and travel differently.In this episode:Why they moved to Portugal with a three-year-oldHow travel has shaped their daughterThe realities of slow travel as a familyWhy nothing has to be permanentTurning a personal travel problem into a businessBuilding community wherever you are

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 into military service, leaving the company he’d spent years building. While serving on the front lines, he received an unexpected acquisition offer with just 72 hours to decide. After a life-altering combat experience forced him to rethink what mattered most, he signed the paperwork from a hospital bed.In this episode, we talk about building a company without chasing investors, why curiosity is a founder’s greatest advantage, how surviving war reshaped his priorities, and the unconventional LinkedIn message that ultimately led him to his wife.It’s a conversation about entrepreneurship, perspective, and what happens when life completely rewrites your plans.

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 talked, the more that answer made sense.Germán doesn’t think in defining moments. He thinks in accumulated experiences.He told me about growing up in South America after his parents rebuilt their lives following the Holocaust. For a period of his childhood, his family lived in a shipping container. He laughed while telling stories about accidentally blowing up his mother’s brand-new stove because he didn’t understand the difference between 110 and 220 volts, then nearly burning down the apartment after trying to wire a lamp himself.Most people would call those failures.He called them education.That curiosity, and the willingness to learn by doing, became the thread that ran through his entire career.When we started talking about Avianca, one of Latin America’s oldest airlines, I expected a story about aviation. Instead, he talked about pattern recognition.“I’ve always believed that where there’s a crisis, there’s an opportunity.”It’s a philosophy he’s lived over and over again. Before Avianca, he built businesses during periods of hyperinflation. Later, when the airline entered bankruptcy, almost no one wanted it. He made what he thought was an intentionally low offer just to end the conversation.The offer was accepted.Listening to him, I realized he doesn’t run toward risk because he enjoys uncertainty. He runs toward it because he’s trained himself to see what might exist on the other side.That may have been my biggest takeaway from our conversation.We often think great careers are built around one bold decision.Germán reminded me they’re usually built through thousands of small ones—staying curious, solving the next problem, and seeing opportunity a little earlier than everyone else.Maybe that’s what separates entrepreneurs from everyone else.Not that they take bigger risks.They simply see different possibilities.

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 instead of waiting for someone to hand them one.We explore why AI is accelerating this shift, how work is moving from credential-based to outcome-based, and why adaptability may become the most valuable skill anyone can develop. The conversation isn’t about predicting which jobs disappear—it’s about understanding how to build a career in a world where the rules are constantly being rewritten.We also discuss:Why discomfort is becoming a competitive advantage.How AI changes what employers actually value.The difference between collecting credentials and creating proof.Why building relationships and solving real problems matter more than sending hundreds of applications.How young professionals can create leverage by making themselves impossible to ignore instead of competing in broken hiring systems.It’s a conversation about embracing uncertainty, redefining success, and realizing that the future belongs to people willing to bet on themselves even when there isn’t a clear roadmap.

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. Then a ticket agent предложed (see what I did there, haha) an unexpected solution: board a high-speed train to Moscow, race ahead of her original train, and intercept it several hours later. Against all odds, it worked.That story became a metaphor for how Elena approaches entrepreneurship. Missing one opportunity doesn't mean the journey is over. Sometimes the fastest path forward is the one you never planned.

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 everyone around her. She became convinced she was slowing the group down and falling behind. Then she learned the truth: she wasn't at the back of the group at all. She was near the front.That experience revealed the "Everest Base Camp Lie" a story our brains tell us when we're tired, uncomfortable, or uncertain. Often the narrative in our heads is far harsher than reality.In this episode of Risky Routes, Lauren shares how adventure, endurance, and discomfort have shaped her leadership style, why confidence is built through evidence rather than motivation, and what challenging experiences can teach us about self-perception. We also discuss fear, resilience, and why some of life's biggest breakthroughs happen when you're willing to be uncomfortable for longer than everyone else.

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 exciting vision for the future of healthcare eventually became a lesson in skepticism and leadership.We talk about decision-making under uncertainty, asking difficult questions, and why experience often teaches you what success cannot.

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 episode of Risky Routes, Christian reflects on reporting from Iraq during one of the most consequential geopolitical moments of the 21st century. We talk about the gap between perception and reality, the absurdity and uncertainty of the early occupation, and what daily life actually looked like beyond the headlines.More than two decades later, Christian returned to Baghdad and found a city that was dramatically different from the one he first encountered. The contrast became an opportunity to reflect on how countries, conflicts, and people evolve in ways that outsiders often miss.Along the way, we discuss the lessons journalism teaches about leadership and decision-making: trust your instincts, seek firsthand experience, question conventional wisdom, and pay attention to the stories nobody else is telling.This episode is about uncertainty, curiosity, and the value of getting close enough to the world to see it for yourself.

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 with altitude, weather, or the terrain.During the trek, Tatiana found herself dealing with severe altitude sickness while simultaneously becoming increasingly uncomfortable with the behavior of her guide. What began as subtle warning signs escalated into a situation where her instincts told her something was wrong. Ultimately, it was the support of local villagers who stepped in and helped her navigate the situation safely.Our conversation explores the difference between fear and intuition, why many people wait too long to ask for help, and how communities often show up for us when we least expect it.Years later, Tatiana still travels, still hikes, and still embraces adventure. The experience didn't make her smaller, it made her wiser.This episode is about trusting your instincts, building confidence through adversity, and learning that courage often looks less like fearlessness and more like taking the next step anyway.

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.

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 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.

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 themselves and others.The episode explores:Overcoming fear through small acts of courageWhy nature strips away ego and creates authentic connectionHow high performers benefit from slowing down and being presentBuilding trust and relationships through shared challengeThe idea that it’s never too late to redesign your life around what truly fulfills youTogether, 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.

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 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.

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 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.

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 intense, as Adrian found himself reporting on a contentious presidential election, navigating rising political tension, and eventually stepping into a role as an interpreter for international election monitors.From freezing up in a high-pressure moment of imposter syndrome to finding his footing in a chaotic, unfamiliar environment, Adrian reflects on what it really means to operate when there’s no playbook. This conversation goes beyond travel. It’s about learning that communication isn’t just about words, embracing ambiguity, and realizing that sometimes the most defining experiences don’t give you clarity in the moment… they just push you forward.

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 moments that forced her to keep going, step by step.It’s a story about trusting yourself, leaning on community when you need it most, and redefining what success actually looks like because the most meaningful breakthroughs don’t happen at the top, they happen in the climb.

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 Times photographer and eventually, to a near-death experience in the middle of a violent coup.It’s a story about risk, survival, and what happens when everything goes sideways. But more than that, it’s about perspective and how the moments that almost break you can redefine how you see time, opportunity, and what really matters.Because sometimes the most irrational decisions end up shaping exactly who you become.

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 environmentsThe dangerous trap of tying your identity to your careerWhat it feels like to walk away from Wall Street and build something on your own termsThe “three jobs” framework for creating freedom and optionalityWhy entrepreneurship is less about certainty and more about figuring it out mid-journeyThis 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 realityHow uncertainty can sharpen judgment instead of paralyze itThe difference between reckless risk and grounded optimismAnd how that experience still shapes how Rafael navigates life, leadership, and travel todayRafael 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 RafaelRafael 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 pressureAsk for help without hesitationStay calm and adaptable when plans collapseMove through unfamiliar places with awareness not fearNow 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!