OUR CREW
Hand-selected by owner and skipper Rob Appleyard, the Moneypenny crew is a dynamic mix of talent and experience, with some members having sailed alongside Rob on his previous boat, Secret Weapon (a Fast 40+), while others bring fresh energy and a new perspective. The team spans a wide range of ages and experience levels, from seasoned veterans who have raced around the world, to younger sailors bringing modern techniques and enthusiasm to the boat. Together, they bring a perfect balance of precision, teamwork, and determination to keep Moneypenny at the forefront of competitive racing.
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OWNER & SKIPPER
Rob began sailing junior dinghies at age 12, but his passion for big boats started just a few years later when, at 15, he answered a newspaper ad looking for crew members on two recently acquired 12-metre yachts – Gretel 1 and 2. These boats had been purchased by local legend Alan Bond to launch Australia’s bid for the America’s Cup - it really was that simple back then! Though school eventually got in the way, this early experience set the foundation for a lifelong love of offshore racing, particularly Quarter Ton, Half Ton, and One Ton yachts.
Fully immersed in the sailing industry, Rob went on to own and run Alspar WA, a renowned spar-making business – perhaps staying in school wasn’t the best call after all! One of his career highlights was working across multiple teams in the America’s Cup during the iconic Fremantle campaign – an experience he considers unforgettable.
Among his many sailing achievements, one of the standouts was serving as principal helmsman on the One Tonner Prime Minister during the 1987 Southern Cross Cup. Against a highly competitive international fleet, Prime Minister consistently ranked at the top, finishing as the third One Tonner over the line in the Sydney Hobart Yacht Race that year.
Despite this success, Rob eventually stepped away from both the sport and the industry – though that’s a story best saved for the book! After more than three decades away, a casual sail on the Swan River with a good crew reignited his love for the sport, particularly the camaraderie of big-boat sailing.
That lead to his return with Secret Weapon, a Fast 40+ - a boat that introduced him to high-performance, asymmetric downwind sailing. Now, Rob has taken the leap into the Mini Maxi world with Moneypenny, embracing the complexity, teamwork, and sheer thrill that come with sailing at this level. For him, success isn’t just about results – it’s about building a strong team, pushing the limits, and mastering every challenge together.
Without the exceptional team he’s gathered, this campaign wouldn’t be possible – it’s a massive team effort, and mastering the complexities of this kind of sailing takes everyone working together.
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Alan’s lifelong sailing journey began when his father moved the family to the city to pursue boating. Over 50 years, he has raced across nearly every class and discipline, even competing at the 2000 Olympics. He loves the challenge of racing in new places and brings his experience, tactical expertise, and a big-picture approach to Moneypenny. As tactician, he helps keep the team focused while still making the process enjoyable for everyone. Alan’s motto is “Always apply the KISS theory!”
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After nearly four decades of racing dinghies and skiffs, keelboats, mini maxi's, and superyachts, Ant has experienced the highs and lows of sailboat racing at local, national, and international levels. A versatile crew member, he brings trimming expertise, enthusiasm for success, and his sense of humour to the Moneypenny team, not to mention good looks. As a professional engineer, Ant knows that any day on the water is a great day. "There's a joyous synergy in working together to make these big, beautiful mechanical birds fly!"
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Billy got into sailing through his parents and started on the water at the age of seven. With 33 years of experience (not that he’s counting), he’s raced everything from junior dinghies to high-performance skiffs and multihulls. His sailing resume includes Pelicans, Flying 22s, Flying Ants, 125s, Skaters, 49ers, Tornado catamarans, F18s, Maxis, and Supermaxis. One of his most memorable races was the Fremantle to Bali, but his biggest achievement to date is taking 2nd place in the 2021 Tornado Open World Championships. Billy previously served as boat captain for Secret Weapon, Rob’s previous race yacht, and now brings his experience to Moneypenny, where he takes on multiple roles across the pit, driving, and boat management – making sure everything runs smoothly on and off water. His motto? Simple: “Don’t f**k up.”
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Caedric started sailing as a child at the New England Sailing Club before moving to Sydney to complete a sailmaking apprenticeship, which led to a wide range of inshore and offshore racing opportunities. With over 25 years of experience, he has competed on various boats, including Ray Roberts’ Team Hollywood, and now runs Evolution Sails Australia. As a skilled trimmer, Caedric brings a deep understanding of sail shape and performance to Moneypenny. His favourite race is the Cones Race at Airlie Beach – especially last year on Secret Weapon. “I guess I can trim sails okay!”
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Dan’s sailing journey started with a simple choice – his Dad told him he could play any sport he wanted. After a brief and unsuccessful attempt at rugby, he turned to the next best thing Kiwis are known for: sailing. He quickly fell in love with the sport and has never looked back. With 15 years of experience racing around inflatable marks and seven years competing in F18s, Dan has built a strong background in high-performance sailing. He’s raced Lasers, 29ers, Nacra 15s, Tornados, and F18s, with his biggest achievement being two appearances at the Mixed World Championships in the Tornado class. More recently, he’s spent the last four years honing his skills as a bowman, with his longest race to date being the Fremantle to Exmouth race. When it comes to favourite races, Hamilton Island Race Week tops the list. As a bowman, Dan brings agility, precision, and a steady head under pressure to the front of the boat. With his boat-building experience and hands-on approach, he’s always ready to get his hands dirty and take on the toughest jobs – someone’s got to do them!
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David began sailing at age 10 on International Cadets, then moved on to Kitty Catamarans, Laser, Moth, Tornado, and International 14s. His ocean racing experience includes the 1978 Melbourne to Hobart Westcoaster race on a Carter 33 and the 1987 Sydney to Hobart on a Van der Stadt one-tonner. In 1985, he won the Ben Lexcen / Modern Boating magazine yacht design competition, leading him to joining Lexcen / Lowe Yacht Design and later Challenge Naval Architects, where he contributed to designing Syd Fischer’s Challenge 92 America’s Cup yacht. David’s favourite sailing locations are anywhere warm, with flat water and 15 to 18 knots of breeze. On Moneypenny, David fine-tunes the boat’s performance, adjusts runners, and manages water ballast to ensure the crew stays balanced and the boat runs smoothly.
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Graeme has been sailing for over 30 years and competing professionally for nearly 20. Career highlights include competing for the America's Cup with Oracle Team USA in Bermuda and INEOS Team UK in Auckland. One of the last generation of America's cup Grinders, Graeme will likely be found grinding away aboard Moneypenny, carrying sails, or looking for the lunches or snacks. "It's exciting to sail with a great bunch of West Australian sailors on Moneypenny and to share my knowledge and experience whilst learning from those around me."
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Jack started sailing at the age of seven, introduced to the sport by his parents, and he’s been racing ever since. With 14 years of experience, he’s competed across a variety of classes, including Minnows, Flying Ants, 29ers, Windfoils, Fast 40s, and of course the RP69. His love for high-performance sailing and pushing the limits on the bow has made him a natural fit for offshore racing. When it comes to favourite sailing destinations, Lake Garda and Hamilton Island stand out as the ultimate spots. On Moneypenny, Jack takes on the critical role of bowman, where agility, fast decision-making, and resilience are key. Whether launching sails, calling the timing, or hanging on for dear life at the pointy end, he thrives on the chaos up front.
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James didn’t grow up sailing, instead dedicating his junior years to middle- and long-distance running, alongside intense fitness and strength training. When the opportunity arose to bring that athletic background to Moneypenny as a grinder, he embraced the challenge of ocean racing. The physical demands of the role, combined with the strategy and teamwork involved, have made sailing an exciting new pursuit. While still new to the sport, James is quickly learning the technical aspects of racing and refining his skills. He's looking forward to future events where he can gain more experience on the water and continue to grow as a sailor.
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Sailing has been in Josh’s blood from the start. With his father being a boat builder, yachts were always part of his life, with some of his earliest memories are of Christmas holidays on the water. He began sailing Optis at age six, and by 12, while watching the Whitbread Round the World start from Auckland Harbour, he told his father, “That’s what I’m going to do”, and he did. His sailing career has been filled with remarkable achievements. His biggest was competing in the Volvo Ocean Race on Assa Abloy, his fastest ride was aboard the Trimaran Team Australia, where they set the record for the fastest trip to Hobart, and his most enjoyable was the Kenwood Cup, racing around the Hawaiian Islands. As the former Moneypenny boat captain, Josh brings invaluable experience to the team and is focused on one goal – helping secure a podium finish in the 2025 Sydney to Hobart. “Once a bowman, always a bowman.”
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Justin has always thrived on the teamwork aspect of sailing, which has led him to race on a wide range of boats, from 470s and Vipers to Fast40s, Extreme40s, TP52s, Volvo70s. A versatile and experienced sailor, he was part of Neptune Racing, which topped the World Match Race Rankings in 2017. Now joining Moneypenny, Justin brings his skill, competitive drive, and passion for high-performance racing to the team.
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Kieran has been sailing for as long as he can remember. His first time sailing was just at 18 months old, and he’s been hooked ever since, drawn to the speed and the feeling of being out among the elements. With 19 years of experience across a range of high-performance classes, including Minnows, Lasers, 29ers, Moths, 49ers, IQ Foils, and Flying Ants, he has developed a versatile skill set. Over the past two years, he has transitioned into offshore racing through the Secret Weapon and Moneypenny programs. His biggest sailing achievement to date is taking 1st place in the under-17 category at the 29er Worlds in Gdynia. When it comes to favourite racing destinations, Long Beach in California holds the top spot. On Moneypenny, Kieran plays a key role on the mast, backing up the bow with sail changes and occasionally working the pumps. But just as importantly, he considers himself an integral part of the all-important snack team. His sailing motto? “Lick it, stamp it, send it.”
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Mark started sailing as a forward hand on Flying Ants, then progressed to 16' Skiffs, 420's, 470's, and LW Sharpies - with many club, state, and national championships. His first overnighter was the 1979 Fremantle to Bali, where wind speeds peaked at 60 knots. Mark went on to compete in 12 Sydney to Hobart races starting in 1981, participated in two America's Cup campaigns, and raced in international match racing and offshore events across the east coast of Australia, Europe, and the US. His favourite race is probably the Sydney to Hobart - "the hardest way to get between two parties!”
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Phil was born into sailing, with his grandfather, father, and uncle all deeply involved in the sport. He started young, racing Mudlarks at Perth Dinghy Sailing Club at just six years old, before moving on to Cherubs and Javelins. Over the years, he has crewed on many boats including Secret Weapon (Fast40+), and currently also sails on an International 14, Stealth. As a part of the Moneypenny team, Phil is excited to race out of Fremantle and Sydney with a top-tier crew.
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Simon has been sailing for 28 years, having grown up in a family passionate about the sport. His background is rooted in one-design racing, with experience in Etchells, J24s, S80s, and S97s, along with offshore campaigns on Fast 40s, TP52s, and Cookson 50s. Once of his biggest achievements was campaigning a J24 in his 20s, competing at state, national, and world championships. As Moneypenny’s main trimmer, Simon plays a key role in the speed loop, constantly fine-tuning the sails to maintain the boat’s balance and efficiency. Whether maximising performance in offshore conditions or pushing the limits on the racecourse, he’s focused on keeping Moneypenny fast and competitive.
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Will’s sailing career spans over four decades, with an impressive list of achievements across offshore and inshore racing. As a WA representative skipper, he finished sixth overall in the Australia Cup and has competed in three Australia Cups as crew, securing a first-place finish in one. He has also claimed victory in the Blue Water Championship twice and the prestigious Big Boat Series in San Francisco. His offshore experience is extensive, having completed two Sydney to Hobarts, the Southern Cross Cup, and the China Sea Race Series, including the Hong Kong to Manila Race. Closer to home, he has competed in the Fremantle to Bali and Fremantle to Cocos Island races, along with ten Fremantle to Geraldton races and four Fremantle to Albanyraces. In addition to his offshore success, Will is a former Laser Club Champion, demonstrating his versatility across different classes. Beyond racing, Will has been a dedicated sailmaker in Sydney, Auckland, and Perth for over 40 years, combining hands-on craftsmanship with a deep understanding of sail performance.