From the rugby fields of London to the Merchant Navy, Special Forces, skydiving, aviation, and entrepreneurship—Paul Illingworth’s life has been defined by risk, resilience, and relentless drive. In this episode of Live Free Ride Free, Rupert Isaacson sits down with Paul to trace a journey that spans fear, family, and the search for tribe.

Paul shares how being bullied as a child forged his fighter’s spirit, how rugby and the Navy honed his leadership, and why fear should never be allowed to rule your life. From building successful businesses—including skydiving operations and escape rooms—to exploring how community can heal a generation lost in gaming, Paul offers raw insights into courage, discipline, and finding purpose.

✨ “Fear is something you build up inside you. Push it aside—and deal with life.” – Paul Illingworth

✨ “It always comes back to tribe. Whatever your tribe is, find it and commit to it.” – Paul Illingworth

🔍 What You’ll Learn in This Episode:

• How a childhood accident and bullying sparked resilience ([00:07:00])
• The lessons rugby taught about teamwork, leadership, and belonging ([00:19:00])
• Joining the Merchant Navy and confronting storms at sea ([00:29:00])
• Why fear must be faced head-on rather than avoided ([00:47:00])
• The leap from oil rigs to aviation and skydiving ([00:58:00])
• Lessons from flight school and pushing limits in the air ([01:00:00])
• Navigating life-and-death moments and mastering discipline ([01:06:00])
• The importance of camaraderie in high-risk environments ([01:10:00])
• Building a successful skydiving business from scratch ([01:20:00])
• Creating escape rooms as a new form of entrepreneurship ([01:41:00])
• Why gaming culture points to a deeper hunger for tribe ([01:45:00])
• Fatherhood, resilience, and passing strength to the next generation ([01:50:00])
• Why tribe and community remain central to a fulfilling life ([01:53:00])

🎤 Memorable Moments from the Episode:

• Paul describes being bullied and deciding to fight back ([00:07:00])
• Discovering rugby as a space for belonging and leadership ([00:19:00])
• Facing storms during Merchant Navy service ([00:29:00])
• Learning to control fear through discipline ([00:47:00])
• Stories of flying and skydiving adventures ([00:58:00])
• Building and selling businesses, from skydiving to escape rooms ([01:20:00])
• Reflections on tribe, community, and resilience ([01:50:00])

📚 Projects, Thinkers, and Ideas Mentioned:

• Paul Illingworth – Entrepreneur, Navy veteran, business innovator (skydiving, escape rooms, aviation)
• Rupert Isaacson – The Horse Boy, The Long Ride Home, The Healing Land
  https://longridehome.com/books

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Website: https://rupertisaacson.com

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