In Episode 14 of The Incredible Machines Podcast, hosts Jon Oliff and Luke Holden sit down with a true force of nature—Oscar Chalupsky. A world-renowned athlete, Oscar is a 12-time winner of the prestigious Molokai Surf Ski World Championship, an Olympian, and a man who has defied medical odds in his battle with multiple myeloma, a form of bone marrow cancer.
From dominating surf ski racing for over four decades to challenging conventional medical wisdom through fasting and alternative treatments, Oscar’s story is one of relentless determination, adaptability, and an unbreakable competitive spirit.
From Junior Champion to Global Legend
Oscar's athletic journey began early. At just 15 years old, he made history by winning both the junior and senior Ironman titles on the same day at the South African National Life Saving Championship. This was just the beginning. Over the years, he would go on to revolutionize surf ski paddling, blending technique, endurance, and a strategic mindset to conquer the Molokai race a record-breaking 12 times—his last victory coming at the age of 49.
His career has not been without its challenges. Banned from Molokai for seven years due to political restrictions and later facing obstacles in the business world, Oscar never let setbacks define him. Instead, he embraced change, whether by pioneering new training techniques, adapting to different sports, or transitioning into coaching and mentorship.
The Power of Mindset and Adaptability
A key theme in the conversation is Oscar’s belief in the power of mental strength. When he was diagnosed with multiple myeloma in 2019, doctors gave him six months to live. Instead of accepting his fate, he researched alternative therapies, practiced extended fasting, and maintained his rigorous training schedule. Despite multiple relapses and being given days to live in 2023, Oscar refused to surrender.
His approach to life is summed up in his philosophy: No retreat, no surrender. Whether in sport, business, or health, he emphasizes adaptability, resilience, and a refusal to accept limitations imposed by others.
Lessons from a Life of Competition
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Question Everything
Oscar believes in challenging conventional wisdom, whether it’s in medicine, sports training, or business. When doctors told him there was no hope, he researched and tested new methods to fight his illness. Similarly, he changed the way athletes approached training, introducing new paddling techniques and gym routines that are now standard practice.
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The Importance of Networking and Relationships
Throughout his career, Oscar has built strong networks in sport and business. He emphasizes the value of authentic connections, sharing how he has maintained relationships with global athletes and business leaders. His belief? "Give, and you will receive."
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Sport and Business Require the Same Mindset
Oscar draws parallels between sport and entrepreneurship, stressing discipline, consistency, and the ability to read the game. Just as in paddling, where reading ocean swells is crucial, in business, understanding market trends and adapting quickly can be the difference between success and failure.
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Resilience Over Everything
Whether facing a rough ocean crossing or a cancer diagnosis, Oscar’s unshakable resilience has defined his journey. He trains, he studies, and he fights—every single day.
The Future: Chalupsky Surf Skis and Beyond
As a lifelong innovator in the sport, Oscar has launched Chalupsky Surf Skis, his own brand of surfskis designed with decades of experience in mind. His goal is to make the sport more accessible while continuing to push the boundaries of performance.
Despite ongoing health battles, Oscar remains an active competitor, coach, and mentor, inspiring a new generation of athletes to embrace the no retreat, no surrender mentality.
Final Thoughts
Oscar Chalupsky’s story is one of unwavering determination, a refusal to accept limits, and a deep love for the ocean and competition. Whether you’re an athlete, entrepreneur, or simply someone looking for inspiration, his journey is a testament to the power of mindset and perseverance.
Tune in to The Incredible Machines Podcast for the full episode and prepare to be inspired by a man who refuses to back down—no matter the odds.
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