In this deeply inspiring conversation, I sit down with paddling legend and 12-time Molokai champion Oscar Chalupsky. Oscar’s story is one of resilience, mental toughness, and relentless optimism—from world-class athletic feats to facing cancer. Whether you’re an athlete, entrepreneur, or anyone seeking strength in adversity, this episode will leave you energised and empowered.

We explore what it means to truly have the will to win—how Oscar has applied this mindset not only in competitive sport but also in his battle with cancer.

Oscar discusses his unconventional approach to treatment and staying mentally strong while undergoing therapy. He shares lessons about sacrifice, consistency, and the inner engine that drives self-belief.

This episode also highlights Oscar’s passion for mentoring others and how he instils the values of resilience, preparation, and humility in those he coaches. We discuss why emotional discipline is essential for success and how learning from failure can become a superpower.

Finally, Oscar shares a memorable story about fellow paddling legend Grant Kenny, revealing what true greatness, respect, and competition look like at the highest levels.

 Key Takeaways

• Resilience is built daily—through habits, mindset, and choosing to act in the face of adversity.

• True champions are forged not just in competition, but in how they deal with life’s hardest challenges.

• Mental discipline, emotional control, and consistency matter more than raw talent over time.

• You can face even life-threatening situations with purpose, clarity, and belief in yourself.

Connect with Oscar below:

⁠(2) Oscar Chalupsky OLY | LinkedIn⁠

⁠Oscar Chalupsky – Corporate Speaker⁠

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Clint