1. EachPod

$20 Million Loss to a Billion-Dollar Vision – Lessons in Risk, Resilience & Reinvention with Damion Lupo #115

Author
Paul Ryan
Published
Thu 14 Aug 2025
Episode Link
https://theinnerentrepreneur.podbean.com/e/20-million-loss-to-a-billion-dollar-vision-%e2%80%93-lessons-in-risk-resilience-reinvention-with-damien-lupo-115/

In this episode, Paul sits down with serial entrepreneur Damion Lupo — founder of nearly 80 companies, author of 12 books, and co-founder/CIO of FrameTec, closing in on a $1B valuation.


Damien shares the raw truth about starting (and ending) dozens of businesses, losing $20 million in 12 months, going homeless, and rebuilding from scratch. Together, we explore:



  • Why “failure” is just feedback and how redefining it will change your entrepreneurial game

  • The mindset shift from chasing money to building lasting impact

  • How to decide when to quit a venture vs. push through

  • The dangers of over-leverage — and how to use debt wisely

  • Why resilience, vision, and environment are more important than IQ

  • The 10-minute, 10-step plan to reach $10M in 10 years (and why that number matters more than $1M or $100M)

  • How to find your calling — even if you think you don’t have one yet

  • Why surrounding yourself with the right people is the ultimate wealth hack

  • The three relationships every entrepreneur should maintain: mentors, peers, and mentees


Whether you’re scaling, starting over, or simply trying to think bigger, Damion’s story is a masterclass in perseverance, strategic thinking, and self-awareness.


Download Damion’s free resource: TurnkeyRetirement.com


 


About the host:


Paul Ryan is an entrepreneur, 8 figure business owner, mentor, podcaster and creator of the 1-Hour CEO and Life Code Program. As a CEO, Paul has a depth of 'real life' experience of what it takes to be successful in business and life.


 


Connect with the host:


https://www.theonehourceo.com/


 


https://www.linkedin.com/in/paul-ryan-9a98774/

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