On paper, Victoria and I probably should not be friends. I’m 37 and have spent most of my adult life in fairly credentialed, professional worlds. College, grad school, startups, venture capital, office settings. Most of the people around me have followed some version of the same script - college, a career, a desk job, and a conventional definition of success.

At 17, I was getting ready to go off to the University of Pittsburgh. At 17, Victoria became internet famous.

And I still don’t totally understand why she’s famous. I even tried to explain it to my mom.

How We Met

I first met Victoria when I was airbnb’ing in Miami. One night, someone knocked on my door, which was already weird because who knocks on a stranger’s door in 2026? I answered wearing an oversized Bills t-shirt to Victoria. She immediately lit up, introduced herself and started asking me questions. She said she had just moved in and wanted to meet the neighbors. I remember thinking, who does this? It reminded me of living in Syracuse when my 70-year-old neighbor brought over a plate of cookies to welcome me to the neighborhood, except this was a 25 year old woman in Miami.

I indulged her because I do, after all, like meeting random people. She was incredibly friendly and kept complimenting me, including my Bills shirt. For a minute I thought I had cracked the code. Maybe she was a Bills fan. Nope.

She kept chatting and asking me questions about the neighborhood until she finally admitted that she had just moved in and her wifi wasn’t set up yet. Could she use mine?

Aha. There it was. I figured out the mystery.

I gave her my Wi-Fi password and she then asked me if she could follow me on Instagram. Sure. As she turned to leave, her friend looked at me and said, “You know she’s an influencer, right?”

This is Miami. Everyone is an influencer.

Then I shut the door, opened Instagram and saw her profile.Who the hell is this chick?

Millions of followers. Viral videos. Headlines. Feuds. An entire internet history I knew absolutely nothing of minutes earlier when I handed her my Wi-Fi password.

A few days later she invited me over for a Haitian smoothie. I do, admittedly, sometimes make decisions for the plot. So I went. Somewhere in that first real conversation, we figured out that we had a shared love of travel. And not really travel in the vacation sense. We both like going places we don’t know much about, meeting people we weren’t supposed to meet and figuring things out once we get there. We both travel impulsively. We both talk to strangers. We both have a tendency to say yes before figuring out the logistics.

As I got to know her, I started realizing that as bizarre as the friendship might look from the outside, and the very obvious 12 year age gap, there were actually some similarities between us.

One of the biggest is that we are both deeply curious. We will go somewhere where we don’t know anybody. We talk to the person next to us and we both like seeing where a random conversation goes.

One day we were walking on the beach when Victoria saw someone crying. Most people probably would have noticed and kept walking. She went over to talk to her. Half an hour later, we had made a new friend.

That kind of thing happens around her a lot.

Victoria vs Woah Vicky

Sometimes I forget she’s famous until we go somewhere in public and people start recognizing her. It’s strange watching someone I know as the girl who knocked on my door suddenly become “Woah Vicky” to someone else.

I think the fact that I met Victoria before I knew anything about Woah Vicky probably matters. I had no preconceived opinion of her when I opened that door. I didn’t know her internet history, what people thought of her, or what kind of person I was supposed to think she was. I just met her.

And as I got to know her, I started noticing how comfortable she is being herself. She is fuller of life than many people I know. Constantly smiling and laughing as often as a toddler. She has strong opinions (including plenty I don’t agree with) but she will actually listen when someone thinks differently. She doesn’t seem particularly concerned with making sure everyone approves of her.

There is something freeing about that, especially because so much of adult life seems to involve deciding how we are supposed to act, where we are supposed to go and who we are supposed to know.

Leave Your Bubble

This friendship has made me think about how often we presort people as adults. We gravitate toward people our age, in our industries, with similar educations, backgrounds, and lifestyles. It makes sense though and there are practical reasons for it. Your life naturally creates your social circle. But it can also make your world incredibly small.

That is probably one of the reasons I love traveling so much. Travel messes with all of those normal filters. You end up talking to someone because you are sitting next to them on a bus, because you got lost together, or because you ended up at the same bar or maybe because neither of you has any idea what’s going on. You don’t know their resume. You don’t know whether you have mutual friends. You don’t know whether they make sense in your world. You just meet them.

Some of the most interesting people I have met in my life are people I never would have gone looking for, Victoria included.

I’m not writing this to convince anyone to love Woah Vicky. That would probably be a very ambitious goal. I’m writing it because this relationship reminded me how much more interesting life can be when you make room for people who are completely different from you.

If Victoria had never knocked on my door, I probably never would have met her. And if I had known who she was before she knocked, maybe I would have made assumptions and I wouldn’t have answered. Instead, she was just some random girl in Miami asking for my wifi.

And maybe there is something to that. We spend a lot of time deciding who people are before we actually know them.

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.

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. 🎲

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

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Then, everything changed.

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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.

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.

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We also discuss:

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• 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.

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.

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.

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.

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.

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.

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The episode explores:

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• Why nature strips away ego and creates authentic connection

• How high performers benefit from slowing down and being present

• Building trust and relationships through shared challenge

• The idea that it’s never too late to redesign your life around what truly fulfills you

Together, 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.

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.

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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.