Oscar Chalupsky is a watersports legend in South Africa and around the world. Oscar is best known for his exploits in the fields of open ocean surfski, lifesaving and paddling. You can read about Oscar’s many sporting achievements here

Successful Businessman


Oscar has always brought that same determination and will to win into his working life. Oscar has been a phenomenally successful salesman and representative for companies such as Sanlam and Chalupsky Properties. Oscar has established and managed his own financial investment company, Chalupsky & Associates, is a founder member of Citadel Investment Services, SA and a co-founder and Vice President of Epic Kayaks, USA, establishing facilities in China and the Philippines.

Oscar’s belief in himself together with his exceptional interpersonal skills and attention to detail has ensured that he is always on top of his game… on and off the water.


Currently juggling three different portfolios: consultant at Nelo Surfskis, Portugal; Coach here at CoachChalupsky and sales and marketing at NuMobile, SA; Oscar is also embroiled in the fight for his life against a cancer with no known cure.

Cancer Fighter



From when Oscar was first diagnosis with Multiple Myeloma and given 4 to 6 months to live, Oscar has openly shared his journey of radiation, chemotherapy and a bone marrow transplant with his loyal and supportive global fan base on his social media pages.



Oscar Featured on Carte Blanche

Carte Blanche visits the legendary champion and coach at home in Cape Town as he regains his strength.

"Chalupsky is now embroiled in the fight of his life – against a cancer with no known cure. He’s taken his adoring global fan base along with him on his social media pages, as he grappled with the pain of chemotherapy and a bone marrow transplant."


Source: Carte Blanche

Knowing Oscar and how he charges at the challenges thrown at him I was keen to see how he balanced his infamous confidence with this new challenge that I could not pretend to comprehend. I heard an Oscar that balanced the sheer force of his personality with a sense of humility and gratitude that was inspiring. The challenging humour leveled at his competitors was delivered with both a sense his inimitable confidence and respect. The balance of wit and win was great and clearly paved the way for his biggest challenge ever. He made something that would have broken the best of us somehow uplifting and reassuring and that there are two ways to tackle seemingly insurmountable hardships.....either throw in the towel or draw on all your inner strength, and those close to you, and stare it in the eye. That’s what Oscar did. - Dale Tomlinson

Keto/Banting and Intermittent Fasting

A close friend of well-known South African scientist Professor Tim Noakes, Oscar has followed the Banting and Ketogenic lifestyle combined with intermittent fasting for many years. He believes that these eating habits have helped him manage his cancer treatments with far less side effects than other patients.

Professional Speaking

Oscar now also offers motivating and uplifting talks where he candidly shares how his determination has made him a winner and a survivor. Contact Oscar to schedule one of his talks either online via Zoom or Teams or in-person (area and travel limitations dependent) which can focus on:

• Sports

• Successful Selling

• Attitude

• Diet & Lifestyle

• Battling Cancer




Having experienced literally hundreds of speakers-live and on YouTube-over the last 20 or so years. it takes a lot to wow me but that's exactly what happened when I attended Oscar's talk in Durban a short while ago. He really is a one-of-a-kind human being and an athlete with the sort of self -belief and achievement which makes one think of Ali and Armstrong. His presentation was engaging and well delivered and his story compelling and inspiring. I can recommend him to anyone who wants their audience to feel uplifted and go away with some practical knowledge for living life more fully. - Vernon O’Connel


Multiple Myeloma Fund

Oscar has set up a Multiple Myeloma Fund South Africa together with the assistance of Stuart Lowe and Campaigning for Cancer. This fund is to raise money for Multiple Myeloma patients in South Africa as this cancer is extremely expensive to treat. Oscar will be donating a percentage of all income generated from his talks to this fund.