Blog #6 - The Traveling Entrepreneur Part #1: Searching for the American Dream

The Traveling Entrepreneur – Part #1: Searching for the American Dream

I’ve never been the kind of person who truly enjoyed vacations. As a kid, I loved my one trip to Disney World and summers visiting my grandparents in Prince Edward Island, but the idea of laying on a beach doing nothing all day has always felt like a waste of time to me, I would much rather explore.

Lately, my perspective on travel has undergone a meaningful transformation. I used to view it as a break from routine—a way to unwind or escape. But now, I no longer see travel as a waste of time; instead, I’ve come to understand it as an opportunity for growth and learning. As I’ve matured a bit and my entrepreneurial mindset has taken shape, travel has evolved into something much more purposeful. It’s no longer just about relaxation—it’s about exploration and inspiration.

Every new city I visit sparks fresh ideas and challenges me to think creatively. I find myself constantly observing and asking questions: What's the cities history? What does this place need? What kinds of businesses succeed here? How do culture, community, and environment shape opportunity? Travel has become a way for me to understand not just the world, but the potential and ambition within it. It sharpens the ability to see gaps in the market, to imagine new ventures, and to envision how different contexts demand different approaches.

I’ve also realized that success in business isn’t just about identifying a need or filling a gap—it’s about understanding the setting. The environment matters and building that environment to always be better is important. A great idea in the wrong place can fail, while a simple concept in the right place can thrive. Travel teaches me to pay attention to these nuances, to notice not just what’s missing, but why it matters—and where it could actually work.

Work is at the heart of this mindset shift. Growing up in Canada, I always admired the American Dream: the belief that no matter who you are or where you come from, you can achieve success through hard work and determination. It’s a powerful idea—one I’ve rarely seen reflected in Canada with the same intensity or scale. In my travels over the last few years, I’ve started searching for this American Dream in real life. Two cities I’ve visited and will be using as examples today stand out, both for different reasons—Chicago and San Francisco

Both cities inspired me, not just for their energy, but for how they framed work—not as something to endure, but as a vehicle for building, shaping, and thriving. Seeing these differences has pushed me to rethink what kind of work I want to do, and more importantly, where and how I want to do it.

Chicago and San Francisco—each offering a very different interpretation of what the American Dream looks like today.

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Chicago: Big Energy and Bigger Possibilities

In September 2023, I took a trip to Chicago. I’ll admit—I was a little nervous. I’d heard the horror stories about crime and danger in the city, and I didn’t know what to expect. But my experience couldn’t have been more different from the stories I'd heard. As long as I stayed downtown and avoided the South Side, I felt completely safe—even walking around and exploring the city at 1 or 2 a.m. I was never looking over my shoulder or uneasy about where I was. Even the few homeless individuals I encountered were kind and polite, often offering a friendly greeting as I passed.

Chicago blew me away. The city is clean, energetic, and visually stunning. Its iconic architecture, rich history, diverse food scene, and cultural energy sparked something inside me. I felt inspired. I found myself dreaming bigger, rethinking my business ideas, and imagining bold new possibilities. Chicago made me want to build—want to accomplish things I hadn’t dared to consider before.

There’s something magnetic about the city—an intensity that lives in the streets, the people, and the rhythm of everyday life. Chicago carries a legacy of boldness and reinvention, rooted in its working-class history and shaped by bold and big decisions, businesses that people will migrate to the city to be a part of, creativity, and commerce. The city blends tradition with ambition while honoring and celebrating it's history. There’s a strong sense of place and community, but also a hunger to grow, adapt, and do more. The entrepreneurial spirit here doesn’t feel performative—it feels authentic and earned. I met people who weren’t waiting for ideal conditions or outside validation; they were simply making things happen because they imagined the impossible and decided to go for it.

In one word, I’d describe Chicago as inspiring. It’s a place that made me believe more strongly in the power of vision, determination, and work. The American Dream feels alive here—not as a cliché, but as something real and tangible. You can see it in the pride of the people, the energy of small businesses, and the way the city keeps pushing forward. Chicago didn’t just surpass my expectations—it reshaped them.

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San Francisco: Opportunity Meets Reality

In March 2024, I visited San Francisco. It took a few days to realize, but by the end of my trip, the city had dazzled me—walking across the Golden Gate Bridge, riding the iconic cable cars, visiting Alcatraz, and seeing the Full House house were all unforgettable experiences. I even toured the Walt Disney Family Museum and visited Industrial Light & Magic, which, as a creative entrepreneur, was deeply inspiring. There’s no question that San Francisco still holds magic, especially for dreamers and builders.

But San Francisco is also a city of contradictions. The homelessness crisis is impossible to ignore. I saw drug use in broad daylight, including right in front of police officers who did nothing. Crime and poverty have scarred what once was—and I believe still could be—one of the world’s greatest cities. Retail spaces downtown sit empty, and the infrastructure is visibly crumbling. San Francisco has potential, but it’s buried beneath complex, unresolved problems.

I couldn’t imagine building a business there—not without first investing a fortune just to clean things up. High taxes, a broken social system, and visible homelessness and crime make it a high-risk environment. Where Chicago inspired ideas, San Francisco triggered caution. It didn’t make me want to build. It made me want to fix.

San Francisco had always loomed large in my imagination—a city synonymous with innovation, disruption, and limitless potential. And in many ways, that spirit still lingers. The culture encourages you to move faster, and challenge convention. People don’t just talk about ideas—they act on them. You can almost breathe in the belief that anything is possible with the right pitch, the right platform, the right timing.

But beneath that energy is a sobering truth. San Francisco is a city of extreme contrasts. The tech-fueled wealth sits uneasily beside visible suffering. The American Dream here feels sharper, more competitive, and undeniably more exclusive. Where as Chicago felt more like having a dream and making it work no matter what, San Francisco felt more like having a dream is possible if you know the right people.

And yet, I left San Francisco with a more grounded perspective. The city reminded me that opportunity is never evenly distributed—and that chasing big ideas comes with real-world trade-offs. Success here requires more than just hustle; it demands resilience, awareness, and often, privilege. San Francisco didn’t inspire me in the same way Chicago did, but it challenged me. It made me ask harder questions about access to opportunity, and what kind of entrepreneur I want to be.

Opportunity is available in San Francisco—but so is reality. And that balance, while uncomfortable, offered me clarity. It taught me that while chasing dreams is essential, so is staying grounded in the human side of the work: the people, the systems, the consequences. It’s not just about building something new—it’s about building something that matters.

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What Is the American Dream—And What Could It Be?

The American Dream has always been more than just an economic concept—it’s a cultural identity. At its core, it promises that anyone, no matter their background, can achieve success through hard work, determination, and a willingness to take risks. It’s the driving force behind Silicon Valley, Wall Street, Hollywood, and small-town Main Street. It’s what has drawn people from all over the world—not just to chase opportunity, but to build something meaningful.

But the modern reality is more complicated.

In places like Chicago, the American Dream still pulses through the city’s heartbeat. You can feel it in the architecture, the hustle, the ambition, and the pride of the people. There, it feels earned, alive, and inclusive. But in San Francisco, the Dream feels fractured—buried under the weight of homelessness, crime, broken infrastructure, and a skyrocketing cost of living. The potential is still there, but access to it feels increasingly gated, reserved for those with the right connections, capital, or simply luck.

So, what could the American Dream become?

Honestly, I don’t think it needs to be reinvented. I think Americans need to return to what they’ve always done at their best: strive for greatness, overcome hardship and differences, and work toward building what once seemed impossible. Then, once that dream is accomplished—keep going. Keep building. Keep believing that progress is not a finish line, but a mindset. The American Dream doesn’t have to be perfect to be powerful. It just has to remain open, evolving, and fueled by the same spirit that built it in the first place.

What Travel Teaches Entrepreneurs

These two cities showed me something important: the environment you build in matters. The American Dream still exists—but how it manifests varies by location. In Chicago, the dream is bold, aggressive, and full of energy. In San Francisco, it feels fragile, buried beneath layers of social and economic decay.

As an entrepreneur, you can’t switch off your mindset—but you have to be realistic. In some cities, success means simply surviving. In others, it means thriving.

This journey is far from over. I plan to visit more American cities—Boston, New York City, Miami, anywhere in Texas, etc—and see how the American Dream lives on there. I’ve seen the American Dream in both small and large ways. But one thing has become clear:

Maybe what I’m really looking for isn’t just the American Dream.

Maybe, because of where I live and where I’m from, what I’m really searching for and trying to figure out is how to take the American dream and adapt it into what the Canadian Dream could be.