Risky Routes

What happens when you’ve spent decades building a successful career, reached the C-suite, and realize it’s time to do something entirely different?

Tonia O’Connor spent more than 25 years in media and entertainment, helping transform major brands like TV Guide and Univision before making the leap into health and wellness, where she served as CEO of Chopra Global and Tone It Up. But along the way, she discovered something unexpected: she loved building people more than building businesses.

We sat down in Saratoga Springs to talk about the decisions that shaped her career, starting with a family adventure through Colombia that took her far beyond the typical tourist destinations. Her curiosity for the unfamiliar has been a constant throughout her life, including her willingness to walk away from the security of established companies to bet on herself.

Today, as co-founder of The Kite, Tonia works with CEOs, founders, and leadership teams to help them think bigger and reach their next level.

We explore why the very things that made you successful can eventually hold you back, why imagination is a muscle we need to keep exercising, and how self-awareness, shared values, and accountability can transform teams.

It’s a conversation about reinvention, finding purpose beyond a job title, and having the courage to start a new chapter, even when you’ve already built a successful one.

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-old
• How travel has shaped their daughter
• The realities of slow travel as a family
• Why nothing has to be permanent
• Turning a personal travel problem into a business
• Building 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.