In The Wake

JUPITER, FL – January 5, 2017 – It’s lunchtime on a sunny day in Jupiter and I mosey on down to Nature’s Way Café to meet a man who has crafted a career by launching himself off the wake of a boat: Sean O’Brien. A force to be reckoned with, O’Brien is regarded by many within the inner esoteric circles of the sport to be as good as anyone who has ever claimed the best-in-the-world spot. He has a well-established reputation as an innovator; his level of skill while attached to the board can only be superseded by his dedication in promoting and pushing the sport of wakeboarding forward.

Prior to meeting O’Brien, I already know he’s the real deal. Someone who has been immersed in everything that wakeboarding has to offer and that has been inside the wakes of both success and stagnation, and came out of both with the same smile on his face. He is fully committed to continuing a career that is solely reinforced by the same passion he’s had for wakeboarding since he first got on a board at age 13. During that time span, O’Brien has found himself pulling in big money from big name sponsorship endorsements while traveling and competing in events, teaching the sport to others, and other times where he’s struggled to keep business ventures relating to wakeboarding going, but it’s all the same to him as long as he’s able to do what he loves.

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O’Brien arrives to the restaurant with his 10-month-old son, Pierson, in his arms. The ice is broken with a brief discussion about Floridian weather, namely how it’s always ideal for getting wet. This is a topic that immediately prompts O’Brien to inject his water sports lore.

“Living in Jupiter allows me to do what I love whenever I want, but there’s also a lot of crossover potential for other water-related activities that I like doing,” O’Brien notes. “I can wake up in the morning, check the surf report, and if there’s waves, I’ll take my board to the beach. If there’s no surf, I’ll check the wind report, and if there’s wind, I’ll go kiteboarding. If you can’t do either, I’ll get my boat out and go wakeboarding. Wakeboarding is usually my first choice anyway.”

A Central Florida native, O’Brien lived and worked out of Orlando most of his life, until a few years back when he and his wife, Alissa, visited her parents in Jupiter during Thanksgiving and made the decision to stay while hanging out by the Jupiter Inlet.

“We show up and it’s head-high glassy waves, Bahamian-blue water, the sun is setting… you should have seen the glow on her face,” O’Brien points out. “I understood in that moment that this was our home.”

Naturally, the next query had to be about his favorite local wakeboarding spot. “On the Intracoastal south of the Indiantown Bridge all the way to Donald Ross,” he replies. He elaborates that this is his favorite spot because it has the proper depth and it’s long, so much so, than when he gets to the end and the boat turns around, there’s no longer any trailing wake and the water is smooth and flat again. He points out that he prefers going out during the weekdays to avoid the weekend boat traffic.

At the moment, O’Brien holds two jobs: First, he is a marketing associate for O’Brien Watersports (no relation), one of his sponsors for 12 years and running. His position mainly consists of filming and photographing other wakeboarding athletes and then wrapping up the day with his own session, where others will document his ride. When he’s not doing that, he is a stay-at-home dad. The latter of the two positions keeps him more grounded than what he has been accustomed to for the greater part of his life. In fact, O’Brien has been mobile ever since he began making a name for himself in the wakeboarding profession. This dates back to 2002. Fresh out of his high school graduation, O’Brien had been working as a wakeboarding instructor during the summer in Orlando for four years, giving lessons and riding on a daily basis. Even though coaching had led to recognition from local professionals throughout the years, the major impact on his career came when a compilation video showcasing his best tricks surfaced on the Internet that same year.

“I had made some waves locally, but I really put myself on the map of the industry via this video that I put out,” O’Brien paints the picture. “It was a compilation of tricks that included pretty much all the tricks that the pro guys were doing, plus some other tricks that they weren’t doing, that nobody had done before. I sent it to people that ran wakeboarder.com and wakeworld.com and, when it went up, people went crazy for it.”

The timing was key, O’Brien recalls, because it was right before that year’s Surf Expo, the premier global watersports and beach lifestyle tradeshow. The video had caused such a stir that professional wakeboarders that O’Brien personally praised approached him at Surf Expo and commended him on his unique repertoire of daring, elusive tricks. It wasn’t long after that that O’Brien was backed by several sponsors and began competing in the Pro Wakeboard Tour. O’Brien juggled coaching and competing with education throughout those years – he graduated from Florida State University in 2005, at which point, his focus turned solely to his wakeboarding career. Although he hasn’t claimed a championship yet, O’Brien is known in the wakeboarding world as a true original and a pioneer of tricks.

“I don’t consider the tricks I do to be better executed than the other professionals, I just found ways to do those tricks differently or just tried new tricks altogether. I simply focused on variety; I got bored of doing the same thing over and over again so I wanted to do things that no other rider had done.” says O’Brien. “That’s how I exceled in the sport and made a name for myself, by being a unique rider that thought outside of the box.”

At this point in the interview, O’Brien is halfway done with the wrap that he ordered for lunch, Pierson is asleep, and I’m too curious not to ask what exactly is the trick that put him outside of the box; the one that captures his prowess to the fullest; the one that coins O’Brien’s trendsetting. With a low chuckle, he goes into the trick: It’s called an Osmosis 7. It entails pulling a 720º degree spin but instead of passing the handle behind his back during the first 360º, he tosses it into the air, spins a 540º, catches the handle with the same hand, and continues to rotate the last 180º while passing the handle behind his back.

“There was a point where no one had done that trick but me,” O’Brien notes with no small degree of pride. “If an Osmosis 5 (540º degree spin) is a hard enough trick to pull off, executing a 7 puts you on a different plane.”

Asked about what exercise helps to be a better wakeboarder, O’Brien says without hesitance: “Jumping on the trampoline.” A sensible practice, yet I’m sure it’s easy for O’Brien to say, he can actually do a flip while on the outside of a wake.

In conjunction with professional competitions, O’Brien’s coaching ability also progressed. Point in fact: O’Brien finds that coaching can be much more rewarding than the contest scene, therefore it has been a consistent pursuit throughout his career. This avenue of the trade led him to running his own company, Orlando Wakeboard Academy, for five years before transitioning into the role of a traveling coach in 2010. Time again, he has been summoned to run “clinics,” or wakeboarding schools, all over the world. He has passed down his knowledge of the sport and his trademark tricks to students in the Bahamas, the U.K., Germany, Luxembourg, the Czech Republic, Sweden, Denmark, Japan, South Africa, and Singapore, to name a few of the countries in which he has taught. Through his tutelage, some of these students have moved on to achieve competitive success.

“I get to go to different parts of the world and hang out in the boat with great people,” O’Brien says. “It’s incredible to have the opportunity to travel so much and do something that you love all the time.”

Lately, O’Brien has taken an extended break from running clinics internationally and turned his focus to life at home with his family here in Jupiter, but that does not come with breaking away from wakeboarding. Aside from riding every day, he is very excited about the construction of Greg Norman Jr.’s cable-powered wakeboard park that is taking shape at Okeeheelee Park in West Palm Beach and is set to open late next year. It will be the first of its kind in Palm Beach County.

“It’ll be great for the sport because it gives it more of a presence in Palm Beach County,” O’Brien says.

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