Twelve world titles. A lifetime forged on the open ocean. A man shaped by wind, waves, and adversity. A master whose presence has illuminated the path for generations of paddlers. Few stories inspire as deeply, or resonate as powerfully. Oscar Chalupsky is far more than a living legend of our sport. He is a force of nature — someone who has turned the lessons of the sea into a philosophy of life.
SEGT: Oscar, your battle over the past six years against multiple myeloma — both in terms of how you’ve faced the illness itself and your campaign to raise awareness and inspire others — has impressed us all. Not only those of us in the global paddling community who know and follow you, but also many others who have recently discovered your story. Where do you draw so much strength from? Do you believe your experience as a competitive ocean paddler has influenced the way you deal with this challenge as well?
Oscar Chalupsky: Thank you, I really appreciate those words.
My strength comes from a few places. First and foremost, my family, Clare, my Children Luke and Hannah, my 2 brothers Herman and Walter and my sister Alma. When you’re fighting something like multiple myeloma, you realise very quickly that you’re not doing it alone. Their belief in me has kept me going on the days when my body simply didn’t want to cooperate. This doesn’t really happen to me ever.
Secondly, I draw a lot of strength from the paddling community. For almost 50 years I’ve been part of this incredible global family, and now, in ways I never imagined, the community has become part of my treatment. Every message, every story, every person who says, “You helped me once, now I’m cheering for you” that gives me energy.
And yes my life in the ocean has absolutely shaped the way I face this battle. Ocean racing teaches you things you can’t learn anywhere else. You learn to stay calm when everything around you is chaos. You learn not to fight the wave, but to read it, adapt to it, and keep moving forward no matter how long the grind is. You learn that the bad patch never lasts forever there’s always another run waiting if you just keep going.
In paddling, as in life, I’ve always believed in Stability Before Ability, and this cancer journey has been the ultimate test of that. Some days the ocean is flat, some days it’s a storm but your mindset is the boat you’re sitting in. If that’s stable, you can survive the roughest conditions.
So yes, multiple myeloma has taken a lot from me, but it’s also shown me what really matters: love, resilience, community, and the decision every day to keep showing up.
SEGT: During this period of your life, you also published your book “No Retreat, No Surrender.” What are the main messages you wanted to convey through it? Do you think your message resonates mainly with athletes facing challenges, or does it also reach people beyond the world of sport?
Oscar Chalupsky: Publishing No Retreat, No Surrender during this chapter of my life was incredibly important to me. When I started writing it, I didn’t want it to be just another sports autobiography. I wanted it to be a book about mindset, about navigating adversity, and about finding strength when life hits you harder than any opponent ever could.
The main message is simple:
You don’t get to choose the challenges life throws at you, but you always get to choose how you respond. That applies whether you’re racing across an ocean, running a business, fighting cancer, or just trying to get through a tough day. I wanted people to understand that resilience isn’t something you’re born with it’s something you build through experiences, through setbacks, through small daily decisions to keep moving. I’ve lived that principle in sport, but cancer forced me to live it on a completely different level.
And what’s been amazing is seeing how the message has reached far beyond the paddling world. Yes, athletes connect with the competitive side, the discipline, the lessons from racing. But I’ve had messages from people battling illnesses, business leaders, parents, teenagers, even people who’ve never touched a kayak in their lives.
What they all tell me is that the book helped them realise they’re stronger than they think that there is always hope, there is always a next step, and there is always a way forward if you refuse to give up. So while the ocean shaped a lot of my story, No Retreat, No Surrender is really about the human experience. It’s a reminder that whatever your wave looks like, you can face it and you can overcome it.
“But maybe the most important thing paddling gives is healing. For many people including myself, the ocean is therapy. When life is heavy, paddling lightens the load.”
SEGT: As a 12-time Molokai Surfski World Champion — your last win being in 2012 at the age of 49 — do you think that paddling in open ocean conditions, often extremely demanding, shaped your perception of what’s possible in life as we grow older? And has it also influenced how you handle other aspects of your everyday life?
Oscar Chalupsky: Without a doubt. Paddling in the open ocean especially in Molokai conditions has completely shaped how I view what’s possible as we get older. Winning my last Molokai at 49 wasn’t supposed to happen. Everyone told me I was past my prime, that younger athletes had the edge. But the ocean doesn’t care about your age it cares about your mindset, your preparation, and your ability to adapt.
In the ocean, you learn that there is no “ideal age” for greatness. There is only experience, resilience, and the willingness to keep pushing when the conditions turn against you. That’s what Molokai taught me: you can still perform at the highest level if you respect the elements, listen to your body, and sharpen your mind.
That perspective has carried into every part of my everyday life especially now, battling cancer. Ocean paddling teaches you that the hardest sections often come right before the breakthrough. You learn patience. You learn problem-solving. You learn to stay calm when chaos hits. And you learn that progress isn’t always fast, but it’s always possible if you keep moving.
Most importantly, the ocean teaches humility. Out there, you’re never in full control, I was in more control then most, and that’s a good thing. It forces you to respond rather than react, to work with what you have, and to trust that you can find a way through.
So yes, those years on the open ocean don’t just shape how I race they shape how I live. Whether it’s business, recovery, relationships, or health challenges, the lessons are the same: Respect the conditions. Keep your balance. Make good decisions. And never, ever stop paddling.
SEGT: What do you personally think paddling — whether surfski or sea kayaking — gives to people?
Oscar Chalupsky: I think paddling gives people something incredibly rare in today’s world: a sense of freedom and connection. When you’re out on the water whether it’s surfski, sea kayaking, flatwater, it doesn’t matter you’re removed from all the noise of everyday life. You’re present. You’re in rhythm. You’re part of something bigger than yourself. I think people feel that immediately, even on their very first paddle.
Paddling also gives peopleconfidence. The ocean can be intimidating, but once you learn how to work with it not fight it, you start to realise you’re capable of far more than you thought. That feeling is powerful. It carries into people’s work, relationships, health, everything. And then there’s the community. I’ve travelled the world for decades, and paddlers everywhere share the same spirit: supportive, curious, adventurous, a bit crazy in the best way. You can land in almost any country, find a local paddling group, and instantly feel at home. Very few sports create that kind of connection.
But maybe the most important thing paddling gives is healing. For many people including myself, the ocean is therapy. The movement, the salt air, the focus, the quiet… it resets you. When life is heavy, paddling lightens the load.
So, what does paddling give people?
Freedom. Confidence. Community. And a place to breathe.
That’s why once people fall in love with it, they never let it go. My father is 88 and just paddled the world championships of 34km.
SEGT: What can surfski offer to a sea kayaker? Do you think that by practicing surfski, a sea kayaker can improve certain skills such as balance or the forward stroke?
Oscar Chalupsky: Surfski can offer a huge amount to a sea kayaker far more than most people expect. The two disciplines complement each other brilliantly, but surfski brings a few unique advantages that can genuinely elevate a sea kayaker’s skills and overall experience.
First, balance. Because you sit on top of the ski with nothing enclosing you, every movement of the ocean is transmitted directly through the boat. That develops dynamic balance, core strength, and reaction timing far more quickly than an enclosed cockpit. When sea kayakers return to their boats after training on a ski, they usually feel noticeably more stable and confident.
Second, the forward stroke. A surfski is brutally honest if your technique isn’t clean and efficient, the boat tells you immediately. This forces you to refine your catch, rotation, timing, and connection to the water. Sea kayakers who cross-train on surfskis almost always develop a smoother, more powerful, and more economical stroke.
Third, water-reading and downwind skills. Surfski paddling is about flow — catching runs, linking swells, and using the ocean’s energy. Even if a sea kayaker never does extreme downwinds, learning to read the sea like a surfski paddler dramatically improves safety, confidence, and comfort in rough conditions.
And then there’s safety, which is a big one. When you fall off a surfski, you simply remount and carry on. No Eskimo roll, no spray skirt, no flooded cockpit. For many paddlers, that alone removes a huge amount of anxiety around capsizing and opens the door to exploring more challenging water.
Surfski also brings practical advantages: The boats are often half the weight of a sea kayak, which means easier loading, carrying, and most importantly you can paddle for much longer without fatigue. Modern surfskis now even come with hatches for day trips and overnight adventures, so they’re no longer limited to racing. The hull shapes are far more efficient, designed for speed, glide, and performance in rough ocean conditions.
And let’s not forget the fun factor. A surfski is light, fast, responsive, and incredibly rewarding once you get the feel for it. Many sea kayakers who try it say it reignites their passion for paddling. So yes surfski absolutely enhances balance, technique, speed, ocean awareness, and safety. And it opens up a whole new side of the ocean that many sea kayakers never knew they were missing.
“The Atlantic there has a very different character, heavier, colder, steeper water. And places like Nazaré are in a league of their own. The ocean’s power there is unlike anything I’ve ever experienced, anywhere.”
SEGT: Many years ago, you co-founded Epic Kayaks and later collaborated closely with Nelo, introducing several improvements in their boat designs. More recently, you launched your own brand — ChalupSki — which seems to embody all your experience and know-how.
How do these new surfskis differ from the rest? And are there plans to export them to Europe or other parts of the world?
Oscar Chalupsky: That’s a great question, because for me, ChalupSki isn’t just another brand, it’s the culmination of almost five decades of designing, racing, and living in the world of surfskis. My first “Chalupski” surfski, many years ago, 49 years ago to be exact, was actually the first ever mass-produced long-distance surfski. At that time, nobody was building skis on a proper production line, so that alone changed the sport.
Later, when we founded Epic Kayaks, we made another big step forward: the first relatively stable, high-performance surfski and importantly, the first adjustable foot-length system. That one innovation allowed paddlers of different sizes to fit a ski properly something we take for granted today, but it genuinely revolutionised the industry.
My time with Nelo was different. There, we simply refined design we polished ergonomics, adjusted shaping. Nothing radical, just making good ideas better.
But with ChalupSki, for the first time, I could take everything I’ve learned from Molokai wins to decades of coaching and paddling and build the skis exactly the way I believe they should be.
Here’s what sets them apart:
Stability Before Ability. This has always been my philosophy. You can only paddle at full power when you feel secure. All ChalupSki models use full waterlines for exceptional stability without losing speed.
True Formula-1 construction. We manufacture with Pei Sheng in China using prepreg carbon in a full autoclave process the same technology used in Formula One.
That gives exceptional stiffness, incredible durability and industry-leading weights (7.9 kg carbon / 9.9 kg carbon-glass).
Designs built on real ocean experience. Decades of Molokai and downwind racing shaped every detail: Wide, glove-friendly handles, a full-carbon footrest with my original 2004 adjustment system, balanced cockpits, bailer placement that actually works, deck shapes tuned for rough water, wave deflectors, on the go foot length adjustments, built in side handles.
A model for every paddler:
- Tarifa – ultra-stable entry ski
- Waikiki – beginner/intermediate
- Maui – intermediate
- Molokai – intermediate racer
All with the same DNA: stable, fast, and fun in real ocean conditions.
Built for rough water first
ChalupSkis are born in chop, swell, and downwind which is why they feel so alive and predictable in the ocean.
Are there plans to export them? Yes absolutely. We are already expanding globally: Australia receiving the first boat in November. France establishing our main European warehouse. Dealers being finalised in all over Europe and Scandinavia. USA and Canada. New Zealand and Japan next in line.
And to make sure paddlers never have to wait months for a surfski, we’re building a proper global distribution network. Our plan includes: A USA East Coast warehouse. A USA West Coast warehouse. A dedicated European warehouse in France. A Perth warehouse for Western Australia. An East Coast Australia warehouse for NSW/QLD/Victoria and Tas.
The goal is simple:
Wherever you are in the world, you can demo, test, and get your ChalupSki quickly with no long delays and no long distance shipping headaches.
We want the experience to match the performance:
Fast, smooth, and world-class.
SEGT: In recent years, we’ve noticed a trend toward shorter surfskis — from the traditional 6.4 meters down to around 5.5 meters — and often with slightly wider beams. What is driving this trend?
Oscar Chalupsky: You’re absolutely right there’s a clear trend toward shorter surfskis, moving away from the old 6.4-meter “traditional” length down to around 5.2–5.6 meters with a bit more width. And this shift isn’t just fashion it’s driven by real performance gains and decades of practical ocean experience.
Modern design shows shorter can be faster. For years people believed longer boats were automatically faster. But performance actually comes down to: 1. Waterline length, 2. Wetted surface area, 3. Drag. Shorter skis dramatically reduce wetted surface area, which reduces drag. With better shaping and smarter hulls, a 5.2–5.6m ski can be just as fast or faster than a 6.4m ski, especially in real ocean conditions.
And I’ve proven this myself: I won seven Molokai World Championships in a 5.6-meter surfski. That was decades ahead of this trend and it worked.
Downwind performance is better. A shorter ski:1. Accelerates quicker, 2. fits between swells, 3. turns more easily, 4. links runs smoother. This is why I still say stability is speed. If you can stay in control, you’ll catch more runs and go faster.
Shorter skis suit modern ocean conditions. We now paddle in more varied conditions side chop, rebound, messy wind swell. Shorter skis: 1. Pitch less, 2. pearl less, 3. sit more comfortably on the ocean, 4. feel more “connected” to the water, 5. they give paddlers confidence and confidence equals power.
Practicality plays a big role. Paddlers want skis that are: Easier to load onto cars, easier to carry in wind, easier to store, more durable and manageable. A 5.2–5.6 m ski ticks all those boxes. The results speak for themselves. One of the performances I’m most proud of was 80 km in 4 hours 37 minutes an average of 17.7 km/h at age 58, in a 5.5-meter ski. To this day, I doubt anyone will beat that time on that distance in those conditions. It proves that length alone does not equal speed, good design does.
The real driver of the trend?
A mix of: Better understanding of hydrodynamics, improved construction methods, real world ocean performance, what paddlers actually enjoy paddling, and the universal truth that stability is speed. Shorter skis aren’t a compromise they are the evolution of surfski design.
And that’s exactly the philosophy behind the new ChalupSkis.
“When the ocean wants to remind you who’s boss, it doesn’t matter how many titles you’ve won, you give it respect, and you stay humble.”
SEGT: You’ve paddled in some of the world’s most awe-inspiring and challenging waters — from the Atlantic coast of Portugal, including Nazaré with its giant waves, to your home waters in South Africa and the Pacific swells of Molokai.
Where have you encountered the most demanding conditions?
Oscar Chalupsky: That’s a tough one, because every ocean has its own personality, its own way of humbling you and the challenges are very different from place to place. But a few stand out in very distinct ways.
Molokai, for example, has the most consistent big conditions. That channel is raw, powerful, and completely unpredictable. The swells come from multiple angles, the currents shift underneath you, and the wind can go from perfect to brutal in minutes. It’s not just physically demanding it’s mentally draining. You have to read every piece of water for hours. Molokai is a pure test of endurance, skill, and resilience.
Then there’s Portugal, where I used to live part of the year. The Atlantic there has a very different character heavier, colder, steeper water. And places like Nazaré are in a league of their own. The ocean’s power there is unlike anything I’ve ever experienced, anywhere. Even on a “small” day, you feel the weight of those underwater canyons. You don’t mess around at Nazaré, you respect it.
But if I’m honest, the most demanding conditions of my life weren’t in Molokai or Nazaré they were in South Africa, at home. The Indian Ocean can be absolutely relentless. I’ve had days off Durban where the wind was howling, the swell was huge and standing up, and it literally felt like the ocean was trying to shake me off the ski. South African conditions force you to be 100% switched on or they will catch you.
So the short answer?
Most powerful ocean (waves and size): Nazaré, Portugal.
Most consistently challenging: The Molokai Channel.
Most unpredictable and technical: South Africa home.
Each of these places has taught me something. But they all share one truth: when the ocean wants to remind you who’s boss, it doesn’t matter how many titles you’ve won, you give it respect, and you stay humble.
SEGT: In your opinion, what are the three most important qualities that a paddling coach or instructor should possess?
Oscar Chalupsky: For me, the three most important qualities a paddling coach or instructor should have are actually very simple but they make all the difference.
1. Patience and empathy. Every paddler learns at their own pace. Some people grasp things instantly, others need more time. A great coach never becomes frustrated, never rushes someone, and never forgets what it felt like to be a beginner. You have to meet paddlers where they are physically, mentally, and emotionally and guide them forward with encouragement, not pressure. One of my most important coaching principles is this:
Don’t pretend to understand me you must actually understand, or you’ll never remember. A coach should never move on until every paddler truly understands the lesson.
2. The ability to simplify. You can know everything about technique, hull design, biomechanics, downwind theory… but if you can’t explain it simply, then it’s useless. A great coach takes something complex and breaks it down into clear, digestible actions: one stroke, one movement, one improvement at a time. That’s how I coach. I break down the forward stroke body part by body part, legs, hips, core, shoulders, hands so the paddler can absorb each element without feeling overwhelmed. Small chunks. Simple steps. And when I’m out paddling, I’m not thinking about me.
I’m thinking about how to make other people better.
3. Passion a genuine love for the sport. Passion is contagious. If you love paddling, if you love the ocean, if you truly enjoy seeing someone catch their first run or find balance for the first time, the paddler feels it. Passion builds confidence. Passion inspires. And passion makes people fall in love with the sport for life.
When you combine those three qualities patience, clarity, and passion you can help anyone become a better paddler, from absolute beginners to elite athletes. Everything I teach is designed to help people paddle easier, smoother, and with fewer injuries. Even when I say everyone should paddle with zero feather it’s not for me, it’s because I’ve worked it out to make things easier for them.
That’s what coaching is: not teaching people to paddle like you, but helping them paddle better than they ever imagined.
SEGT: Oscar, thank you. We wish you continued health and strength — you truly inspire us with your example. We would be honored to host you in Greece or Cyprus one day and paddle together in our seas. One final question: what has been the most beautiful or memorable paddling experience of your life so far?
Oscar Chalupsky: Thank you that really means a lot to me. And paddling in Greece, which I’ve visited once, with those unbelievable winds, or in Cyprus one day, would be an honour. Your waters are spectacular, and I genuinely hope my health allows me to share a paddle with you there.
As for the most beautiful or memorable paddling experience of my life… that’s a difficult question, because the ocean has given me thousands of moments I’ll never forget. But a few stand out above the rest.
Most people expect me to pick one of my Molokai wins and of course those were special. Winning seven in a row, and then coming back at 49 to win again, those were defining moments in my career. Wining the Sella Descent in Spain with my bother Herman, after my dad had won it was very special.
But the most beautiful moment wasn’t a race.
It was something much more simple paddling downwind with my heroes and family like Tont Scott, my dad and Herman, Walter and Alma.
Another memorable paddle was in the Straits of Gibraltar where I paddled with Clare, Hannah, paddled with Boyan Zlatarev and Luke in a single I think we did 24km out first time everyone of my family paddling together.
A close second happened recently: swimming the Midmar Mile with my 87-year-old father, helping him finish the biggest open-water swim in the world as the oldest novice. After everything I’ve been through with cancer these past years, that moment meant more to me than any world title.
Another incredibly meaningful part of my journey has been teaching people the joy of downwind paddling watching their faces light up when they catch their first proper run, when they suddenly feel the ocean moving with them instead of against them. Helping others experience that magic has become one of the greatest pleasures of my life.
And then there’s the constant in all of it: my wife, Clare. She has been at the finish of every race, every paddle, every challenge no matter how I performed, no matter what happened out there. Just knowing she would be waiting for me on the beach gave every paddle deeper meaning.
And finally, there are the moments only paddlers truly understand being alone in the middle of the Indian Ocean on a huge downwind, flying from swell to swell, totally in flow, totally at peace. Those runs are like meditation. You’re not thinking you’re just part of the ocean. Even today, despite everything, I still dream of long downwinds. They make me feel at one with the ocean and with nature.
So the most memorable experience?
It’s not one event it’s the combination of family, teaching, the ocean, and the feeling of being exactly where you’re meant to be.
That’s what keeps me going.
That’s what I hope to share with others.
And that’s why I still say: No Retreat, No Surrender.