Cuba With EO: A Once-in-a-Lifetime Experience

Sometimes the most meaningful experiences begin with simply saying yes.

When EO Cincinnati President Shanna Novosel invited chapter members to travel to Cuba together, about 50 people decided to take the leap. The timing was uncertain, Venezuela had cut off oil supplies to Cuba, geopolitical tensions were rising and there were real concerns the trip might be canceled. But being part of EO often involves stepping outside the comfort zone. 

Landing in Cuba certainly felt like one of those moments.

What we discovered was a country filled with contrast, extraordinary beauty, vibrant culture, stunning architecture and incredible resilience.

My personal description would be “beautiful ruins.”

Here is a video from one of my fellow EO Cincinnati members, Tim Rettig, that captures the beautiful architecture and the massive disrepair.

Havana feels like a living museum, with colorful buildings and historic streets that tell stories from another era. Yet alongside that beauty are reminders of the challenges many people face every day. 

Seeing it firsthand opened our eyes to the things we often take for granted, and to the power entrepreneurs have to shape opportunities for others. Here are three experiences that were truly OIL, once-in-a-lifetime:

Learning Passion From a Cuban Organic Farmer

One of the most inspiring moments was meeting a local organic farmer who had built his business from the ground up. What started as a small operation has grown into a thriving enterprise employing more than 50 people.

Hearing his story reminded me that personal passion can support success against all odds. Even with limited resources and unpredictable conditions, such as a government that could take it all away at any moment, this entrepreneur found a way to innovate, lead and create opportunity for others. He was passionate about sharing organic farming methods and healthy food with his country. He made it happen beautifully.

Learning to Dream Without Limits From the Cuban Entrepreneur Panel

We had the opportunity to meet with a panel of three Cuban entrepreneurs who shared what it’s like to build a business when the odds are genuinely stacked against you: private business enterprises only allowed since 2011, no big-box hardware stores, no venture capital, no safety net.

Their stories hit differently.

One entrepreneur's goal is to become the largest dried mango exporter on the continent. Not in his city. Not in his country. The continent. And he's doing it in a place where mango grows so abundantly it goes to waste every year,  entire harvests rotting because they all ripen at once and there's no infrastructure to process them fast enough. He saw that waste as an opportunity nobody else had figured out yet.

His first prototype? A friend's pizza oven and whatever drying equipment he could borrow. His startup capital? A student loan from a friend. No Home Depot run. No equipment supplier. No SBA loan. Just a vision big enough to outlast every obstacle between him and it.

That's the thing that stayed with me: It wasn't that these entrepreneurs were working without resources, it's that the size of their dreams had nothing to do with the size of their resources. They weren't waiting for the right conditions. They were building in spite of the obstacles.

It was a powerful recalibration for our group and for me. Most of us have access to tools, capital and each other: These entrepreneurs can only work around. Yet how often do we let smaller obstacles slow us down or shrink our thinking? 

Learning the Power of Community From an Elder Care Center

One of the goals of going to Cuba with EO was to give back. In the end, we left having received more than we gave.

During our stay on the island, we visited an elder care center that operates on one idea: Nobody should be alone. About 60 elderly residents without families live together, share meals and attend cultural programs, art exhibitions and talks that keep them engaged and connected. Workers' children go to school on-site. Volunteers build eyeglasses from recycled parts with over 1,000 pairs distributed last year to people who couldn't see without them.

We brought art supplies and backpacks. They gave us a virtual masterclass in community and what actually makes life worth living. After all, the research is clear: Loneliness shortens lives and belonging extends them. These residents aren't just surviving their later years; they're thriving in them.  

In a world that increasingly isolates people by age, circumstance and geography, this place is proof that community makes life worth celebrating.

The Cuba With EO Difference: Shared Experiences

What made this journey to Cuba with EO truly special wasn’t just what we saw, it’s who we experienced it with.

Traveling together creates a different kind of connection. Conversations happen naturally. Perspectives are shared. Ideas are sparked. These shared experiences deepen our relationships and strengthen friendships. 

Why EO Creates Once-in-a-Lifetime Moments

Looking back, each of these experiences, would have been meaningful on their own. Together, they became something extraordinary.

EO creates opportunities for entrepreneurs to learn, grow and see the world through a different lens. Sometimes those opportunities come in the form of conversations with fellow members. And sometimes they come from traveling halfway across the world to experience something completely new.

This trip was truly a once-in-a-lifetime experience. And I’m so glad I said yes.

About the Author

Margee Moore is the founder and CEO of BigOrange Marketing, a Midwest-based digital marketing agency that helps growth-focused companies turn strategy into measurable results. With decades of experience in branding, storytelling, and digital marketing, Margee works closely with entrepreneurs and leadership teams to build websites, content strategies, and marketing systems that drive real business growth. She is an active member of EO Cincinnati and passionate about supporting the entrepreneurial community through connection, learning, and shared experiences. Learn more at https://bigorange.marketing.