James Lawrence, better known as The Iron Cowboy, is a world-renowned keynote speaker, bestselling author, and endurance athlete who redefined human potential by completing 50 Ironmans in 50 days across all 50 states — and then doing the unthinkable — 100 full-distance triathlons in 100 consecutive days. Before becoming the greatest endurance athlete in history, James was a successful entrepreneur, running a thriving mortgage company and helping hundreds of clients build wealth through homeownership and strategic refinancing. That same relentless mindset that powered him through thousands of miles now fuels his ventures in multi-family real estate and ownership of Crumbl Cookie franchises. He’s been named one of Sports Illustrated’s “Fittest 50,” featured in two acclaimed documentaries, and honored alongside icons like LeBron James and Conor McGregor. But James’s story isn’t just about athletic records — it’s about purpose, resilience, and refusing to settle for average. In this episode of In the Know, Chris Hampshire and James examine the importance of risk-taking in any successful career, techniques for transferring fear to excitement, and the possibilities that are available to those who are brave enough to tackle the unknown.
James will be the closing keynote and conferment speaker at this year’s In2Risk event, taking place November 3‒5 in New Orleans. For more information and to register, visit In2Risk.org. Register by Sept. 5 to take advantage of early bird rates.
Key Takeaways
James’s pivot from the mortgage industry to extreme sports.
The importance of risk-taking in any successful career.
Calculating which risks bring the greatest rewards.
The suffering is worth it when you show up prepared.
The future is filled with possibilities for those who are willing to take risks.
AI leverage has the potential to bring greater joy to the workforce.
Techniques for transferring fear to excitement.
Breaking monumental accomplishments down into manageable tasks.
Personal development and risk-taking.
Staying healthy while achieving incredible goals.
What to expect from James’s keynote presentation at In2Risk.
A five-year look at the rapidly changing future.
James’s encouraging advice to his early career self.
In the Know podcast theme music written and performed by James Jones, CPCU, and Kole Shuda of the band If-Then.
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Quotes
“Sometimes hitting rock bottom can be the greatest gift.”
“What is the risk that I have to take? And what is the benefit to myself, my family, my community?”
“The suffering is always worth it if you show up prepared.”
“For people who understand and leverage AI, it’s going to bring a lot of joy and happiness in their lives.”
“Am I going to allow fear to dictate my decisions, or am I going to continue to chase my dreams?”
“Taking risks and personal development go hand in hand.”
