Interview with Oscar Chalupsky – Paddle Sports Show 2024 Conference & Talks

Oscar Chalupsky, a living legend in ocean racing and surf-ski, and 12-time winner of the prestigious Molokai Challenge, will be sharing his incredible story at this year’s Paddle Sports Show. In his talk, Oscar will discuss his relentless battle against cancer, demonstrating the same tenacity and determination that made him a champion on the water. He will also present his book, “No Retreat, No Surrender,” offering further insight into his remarkable journey. Don’t miss this opportunity to meet the legend himself, Oscar Chalupsky, and be inspired by his story of courage and resilience.


Paddle Sports Show: Oscar, you are coming to the Paddle Sports Show this year, what is the main message you will send across to the audience?
Oscar Chalupsky: Paddling is about more than just the water beneath our boats—it’s about resilience, determination, and the will to keep going, no matter the challenges. I’ve faced fierce waves in the ocean and even fiercer ones with my health, but the lesson remains: never give up. Whether racing, exploring, or battling personal struggles, the key is to stay focused, passionate, and keep moving forward. The paddle sports community is a powerful force—together, we can overcome any obstacle, inspire each other, and keep the spirit of adventure alive. Let’s keep paddling, not just for ourselves, but for each other.


Paddle Sports Show: Tell us how competitive paddling background helps you fight and keep your spirits high in the fight against cancer?
Oscar Chalupsky: My competitive paddling background has been crucial in my fight against cancer. Paddling teaches you to endure, push through pain, and stay focused on your goal, no matter how tough the conditions. These same principles apply to battling cancer. Each day presents new challenges, but paddling has taught me that if you keep pushing, you can make it through. The discipline, mental toughness, and sheer will to win developed over years of paddling have been vital in my cancer journey. It’s about taking things one stroke at a time, focusing on the task at hand, and believing that persistence will get you through. Paddling has also given me a supportive community, reminding me I’m not alone. When things get tough, I draw on the strength I’ve built on the water, knowing that, like in a race, the finish line is within reach if you keep moving forward.

Paddle Sports Show: You wrote a book about your story; what was your goal when you wrote it? Are you surprised by its success, and how many copies have you sold worldwide?
Oscar Chalupsky: When I wrote my book, my goal was to share my journey—the highs and lows of both paddling, business, family and battling cancer—to inspire others to face their challenges head-on. I wanted to show that resilience, determination, and a positive mindset can help you overcome even the toughest obstacles.
I’m incredibly grateful and a bit surprised by the success of the book. It’s humbling to see how many people have connected with my story. As of now, we’ve sold over 30,000 copies worldwide, and it’s still going strong.


Paddle Sports Show: It seems like your mission now is to send a positive message to those facing difficulties worldwide, similar to the mental challenges athletes face in endurance races like surfski. Is that your focus?
Oscar Chalupsky: My main mission now is to inspire people facing tough battles, whether it’s illness or any other challenge, to embrace the fight with the same mental toughness and determination athletes use in endurance races like Surfski. It’s about accepting the pain, staying focused, and never giving up, no matter how difficult the journey gets. The mindset that carries you through a long race can also carry you through life’s toughest moments.


Paddle Sports Show: These days, you work with Nelo Kayaks and also run conferences worldwide. What kind of audiences and countries do you speak to?
Oscar Chalupsky: I speak to a diverse range of audiences—from corporate groups and sports teams to schools, school principals, and cancer patients. My talks focus on resilience, mental toughness, and overcoming adversity. I’ve had the privilege of speaking in countries around the world, including South Africa, Australia, the United States, and various parts of Europe. Each audience brings its own unique energy, but the core message of perseverance and positivity resonates universally.


Paddle Sports Show: is there anything better than paddling?
Oscar Chalupsky: For me, golf comes a close second!