From Switchblades to Startups to Soulmates: The Wild Ride of Henry Woodman

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Henry Woodman’s story reads like a screenplay, which makes this episode feel like it comes full circle, because a screenplay is exactly what he’s working on now.

In this episode, Henry takes us on a wild ride through his entrepreneurial journey: from smuggling and reselling switchblades at 13, to launching a virtual tour company, to building and selling his startup to a global tech platform used by hotels around the world, and lots of lessons in between.

But this isn’t your typical startup success story. Along the way, Henry battled burnout, bootstrapped through trade show hustle, learned hard lessons in business discipline, and ultimately sold his company right before the pandemic decimated the travel industry. Now? He’s back to his creative roots turning a forgotten family manuscript into a feature film and tv show about reincarnated love.

We talk about:

• Spotting opportunities (even when you’re broke and lost)
  
• What founders get wrong about traction, vision, and culture
  
• Why "wash, rinse, repeat" is the real secret to growth
  
• How to hire when you can’t afford top talent
  
• Why timing is luck but staying in the game is everything
  
• How Henry’s latest venture blends romance, time travel, and the very real future of AI-powered storytelling
  

If you’ve ever wondered what happens after the exit or how to keep reinventing yourself across decades, this one’s for you.

Check out The Reincarnation of Marie

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Each week, we interview founders, business leaders, and experts in their field about how to grow a business and the personal growth that comes with the journey. #LetsGrow !