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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:
🎤 Memorable Moments from the Episode:
📚 Projects, Thinkers, and Ideas Mentioned:
🌍 See All of Rupert’s Programs and Shows:
Website: https://rupertisaacson.com
📲 Follow Us:
Long Ride Home:
Website: https://longridehome.com
Facebook: https://facebook.com/longridehome.lrh
Instagram: https://instagram.com/longridehome_lrh
YouTube: https://youtube.com/@longridehome
New Trails Learning Systems:
Website: https://ntls.co
Facebook: https://facebook.com/horseboyworld
Instagram: https://instagram.com/horseboyworld
YouTube: https://youtube.com/newtrailslearningsystems
📊 Affiliate Disclosure:
Links to books and products may include affiliate tracking. We may earn a commission if you make a purchase, at no extra cost to you. Thank you for supporting the show.
By Rupert Isaacson5
1010 ratings
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:
🎤 Memorable Moments from the Episode:
📚 Projects, Thinkers, and Ideas Mentioned:
🌍 See All of Rupert’s Programs and Shows:
Website: https://rupertisaacson.com
📲 Follow Us:
Long Ride Home:
Website: https://longridehome.com
Facebook: https://facebook.com/longridehome.lrh
Instagram: https://instagram.com/longridehome_lrh
YouTube: https://youtube.com/@longridehome
New Trails Learning Systems:
Website: https://ntls.co
Facebook: https://facebook.com/horseboyworld
Instagram: https://instagram.com/horseboyworld
YouTube: https://youtube.com/newtrailslearningsystems
📊 Affiliate Disclosure:
Links to books and products may include affiliate tracking. We may earn a commission if you make a purchase, at no extra cost to you. Thank you for supporting the show.

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