Henry Woodman is a seasoned entrepreneur whose career spans from a fascination with video games to becoming an influential tech business owner, and now, circling back to his passion for storytelling and filmmaking. In our conversation, we discussed his eclectic journey, marked by both strategic decisions and serendipitous opportunities.

Henry starts with an engaging anecdote about his early experiences that shaped his entrepreneurial spirit. "When I was in college, I was doing video game machines and laundromats because I was addicted to Pac-Man," he recounts, illustrating his knack for recognizing and seizing opportunities. This early venture led to significant advancements in virtual tour technologies and a dominant presence in the travel industry's online landscape, showcasing his ability to leverage personal interests into viable business solutions.

Highlighting the theme of personal challenges morphing into professional opportunities, Henry advises, "Don't just sit there and say, wow, somebody really needs to do something. Maybe that somebody is you." This advice encapsulates his journey and serves as a guiding principle for aspiring entrepreneurs.

Throughout our discussion, Henry addresses the learning curves and adaptations required in his career, including tackling imposter syndrome and embracing lifelong learning. "I went back to school in my fifties to get my MBA in entrepreneurship," he shares, underscoring the importance of adaptability and continuous education in today’s fast-paced business environment.

The conversation also explores Henry’s return to his first love—filmmaking. After years of technological entrepreneurship, he is now focusing on producing a series based on a novel, a project he describes as the closing chapter of his professional life. "I'm going full circle," he reveals, as he plans to adapt the book into a series that delves into themes of reincarnation and soulmates, blending historical and contemporary narratives.

Key takeaways from our talk include:

• The importance of aligning personal passions with business endeavors.
• The need to recognize and capitalize on emerging trends and technological shifts.
• Building resilience and learning from failures as critical components of long-term success.

Henry's journey is a compelling narrative of transformation, resilience, and the full-circle return to creative roots, offering profound insights for anyone navigating their own path in entrepreneurship or creative endeavors. As he aptly puts it, "Mindset is hugely important. Your thoughts create your life," a mantra that resonates through all stages of his career and life ambitions.