Oscar Chalupsky - Episode 133

There’s always something good in somebody at any time”

Few people have the mental strength and positive outlook on life like Oscar Chalupsky. We can all do ourselves a favour and take a leaf out of his book.

His sporting prowess is comparable to many greats in sport. He is a multiple-times global surfski champion, having won the internationally famous Molokai to Oahu World Surfski Marathon championships a record twelve times.

In 2019, he was diagnosed with multiple myeloma, an incurable bone marrow cancer and told he had six months to live. A combination of medical treatment, exercise, iron determination and unconquerable optimism, he has defied every doctor’s prediction to date and is still going strong and competing in races around the world.

It’s a huge privilege for me to have such a raw and fun conversation with a man like Oscar.

Discussion Topics: What you will discover from listening to this Podcast:

  • Balance between competing in sport and growing a career
  • Competing in sports with low cash prize money
  • Different perceptions people have of you
  • What it’s like being a polarising person
  • People confusing confidence and arrogance
  • Why networking and sharing your story are important
  • Why you should speak about your problems
  • Can Sportsmanship be taught?
  • Why planning is your key to success
  • What it’s like being a jack of all trades
  • Not dwelling on the past
  • Tools to help you worry less
  • Respect people, but don’t idolise them
  • Stop saying “You Can’t”
  • Sacrifices it takes to be best in the world
  • Winning Molokai at 49 years old
  • Helping grow the Dusi Canoe Marathon
  • Doing Business with Integrity
  • Managing life with Bone Marrow Cancer
  • Maintaining lifetime self-belief
  • Future goals of Paddling a 100ft wave


I hope you enjoy this conversation as much as I did.

Your fellow being



Background, Context & Reference

Connect with Oscar Chalupsky:







Discussion Links

Surf Lifesaving Ironman

Texan Race / PE2EL Challenge

Molokai Surfki Race

Apartheid, South Africa

Dusi Canoe Marathon

Nazaré, Portugal – Big Wave

Books Mentioned

No Retreat, No Surrender – Oscar Chalupsky

People Mentioned:

Naas Botha

Clive Barker

Dr Khumalo

Music By

Matthew Parker

Right Hook Request


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