Guest: Henry Woodman
Many aspiring entrepreneurs find themselves stuck between their creative passions and the practicalities of running a business. Henry Woodman’s journey from a video game-loving college student to the founder of a tech company that revolutionized hotel photography offers a fascinating blueprint for turning creativity into a successful entrepreneurial endeavor. His story is not just about following a passion but identifying opportunities when they present themselves and knowing when to pivot.
The Unexpected Start: A Pocket Full of Quarters and a Love for Pac-Man
Henry Woodman’s entrepreneurial journey didn’t start with a grand vision—it started in a laundromat with a pocket full of quarters. While he was in college in the late 70s and early 80s, he found himself frequently spending time at laundromats where he couldn’t resist playing Pac-Man. “I was addicted to Pac-Man,” Woodman recalls, “and I was sitting in a laundromat with a pocket full of quarters.” This simple but relatable scenario led to his first business venture: setting up video game machines in laundromats.
Rather than letting this opportunity pass by, Woodman acted on his instinct. He called local laundromats and asked if they would be interested in having video games on site. “Some of them said yes,” he says. With his college funds, he purchased his first machine, setting the stage for a business that allowed him to pursue a passion while solving a problem others didn’t even know they had.
Connecting the Dots: From Travel Films to Tech Innovation
After selling his video game business, Woodman shifted gears, pursuing his dream of working in film. He found himself in the world of travel films, traveling the globe as a production assistant and later as a producer. This experience introduced him to the emerging digital technologies of the time, including nonlinear editing systems and 360-degree virtual tours. In a chance encounter during a project in Chile, he discovered the power of digital editing and virtual tours, which sparked a new idea.
“I can look all around a destination or a room with a computer—I don’t even have to go,” Woodman remembers thinking.
The light bulb moment came when he realized that this technology could reshape the travel industry, allowing hotels to showcase their properties online without the need for large production crews.
Building ICE Portal: From Production to Distribution
What started as a passion for producing virtual tours quickly evolved when Woodman identified a bigger market gap: distribution.
“The production is not the value—it’s the distribution,” he emphasizes.
As hotel websites became more sophisticated, there was a growing need for consistent, high-quality images and virtual tours. However, there were no industry standards for distributing this content across various booking platforms. Seizing the opportunity, Woodman founded ICE Portal (Internet Content Exchange), a company that specialized in managing and distributing visual content for hotels worldwide.
Woodman’s approach was anything but conventional. He openly admits to learning through trial and error, often grappling with what he calls “imposter syndrome.” “I look around the room, there’s a bunch of MBA students auditing these CEOs, and I’m thinking, who the hell am I? I know nothing,” he recalls. But rather than being paralyzed by doubt, he went back to school in his 50s to earn an MBA in entrepreneurship, enabling him to strengthen the business foundations he had already built.
Lessons in Entrepreneurship: Mindset, Pivoting, and Resilience
Woodman’s story is full of practical advice for aspiring entrepreneurs, particularly those struggling to reconcile their creative ambitions with the demands of building a business. He underscores the importance of having the right mindset, stating, “Your thoughts create your life.” This is more than just positive thinking; it’s about recognizing opportunities and having the resilience to push through obstacles, whether they’re technological challenges or moments of self-doubt.
He also emphasizes the importance of pivoting. When he realized that producing virtual tours wasn’t where the value lay, he shifted focus to distributing images and content. “If I can connect to all these places, that’s a huge moat,” he notes, highlighting the competitive advantage of building a network that major hotel chains like Hilton and Hyatt wouldn’t want to leave.
Woodman’s journey also illustrates the power of surrounding yourself with the right people. “You’re the average of the five people you hang out with,” he says. By keeping company with accomplished, driven individuals, he was constantly motivated to push his own boundaries.
Coming Full Circle: Back to Creativity with a New Perspective
Now that he has the financial freedom to choose his projects, Woodman is returning to his original dream of storytelling. He is currently developing a historical fiction series based on a book he acquired the rights to 40 years ago. The project reflects not just a creative passion but a deep understanding of how stories can be told in today’s digital and content-rich environment.
Key Takeaways for Aspiring Entrepreneurs
Henry Woodman’s story is a reminder that successful entrepreneurship is rarely a straight path. It’s about identifying opportunities, taking risks, and knowing when to pivot. Whether it’s through solving a problem or finding a niche, creativity can be the foundation of a thriving business if combined with persistence and strategic thinking.
Start with a Problem, Not a Product: Woodman didn’t set out to build a tech company—he simply wanted to play Pac-Man. The key is to identify problems in your environment that others may share and address them creatively.
Embrace the Learning Curve: You don’t need to know everything from day one. Whether it’s battling imposter syndrome or learning business fundamentals, continuous learning is crucial.
Pivot When Necessary: The ability to pivot, as Woodman did from production to distribution, can be the difference between a good idea and a sustainable business.
Surround Yourself with the Right People: Your environment heavily influences your growth. Seek out mentors and peers who inspire and challenge you.
For those curious about balancing creative pursuits with entrepreneurial ambitions, Henry Woodman’s journey offers a roadmap. The steps may be unpredictable, but with the right mindset and willingness to learn, creativity can indeed lead to entrepreneurial success.
For aspiring entrepreneurs wondering, "How does a creative turn entrepreneur?" the answer lies in a mix of curiosity, adaptability, and resilience. Whether you’re just starting or looking to pivot, the lessons from his story remind us that opportunities often emerge where passion meets perseverance.
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