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.