Multiple International athlete and World Champion Oscar Chalupsky is a once-in-a-lifetime high-performance machine. Few will ever be like him, but almost all of us can learn some valuable lessons from the man.

Whilst still at school, he played South African schools water polo, was a springbok lifesaver, became the youngest Springbok canoeist, played provincial schools rugby, was the South African Iron Man champion, and South African ocean kayak champion.

He went on to become 12 times World Champion paddle ski or ocean kayak champion, winning his 12th title at the age of 49, 29 years after winning it for the first time.

Throughout, he was an amateur athlete who also worked full-time and built successful businesses. In the year South Africa was banned from participation due to apartheid policies, he took up golf, and a year later had a scratch handicap. For aspiring golfers, he shares how he did this, whilst remaining married and holding down a full-time job.

In November 2019 and at the age of 56, Oscar was diagnosed with multiple myeloma cancer and given 4-6 months to live. Today (April 2022) he is still running, swimming, kayaking, working and competing against the world’s best, whilst taking this cancer, plus a more recent diagnosis of skin cancer, head on and with a glass of wine in his hand.

This is one hell of a conversation with Oscar Chalupsky.

Young Oscar 3.30

Mindset during a race 13.00

The Molokai 17.30

Brain Training 22.40

The Science Behind the Sport 25.00

Entrepreneurial Mindset in Sport 29.40

Out of the Box 33.00

Pushing the Body 34.50

Winning (12th) Molokai  37.50

The Switch to Golf 42.30

1992 Olympics 48.30

Disappointments 49.45

The Diagnosis 51.50

Message to Cancer Patients 58.10

What's Next? 1.02

The Big Question 1.07.40