Olympic Sailing

The passionate pursuit of excellence across generations

The Olympics—a competition that conjures thoughts of patriotism, athletic prowess, and the passionate pursuit of a dream. These elements are undeniably part of the formula that makes the Games so compelling. But for those who have coached and competed in this vaunted sporting event, another equally important factor is relationships—with oneself, one’s coaches, one’s teammates, and one’s competitors. And nowhere is this more evident than in elite sailing.

“Sailing is all about relationships—with yourself as well as with those you sail alongside and against,” observes Rob Hurd, Tabor’s sailing coach for the past 34 years, the last 25 as head coach. Personal interactions are particularly important to athletes pursuing Olympic gold, he continues. “In order to chase a medal, you’ve got to finance a training campaign and keep people interested in your efforts, so you need to be smart about relationships. Your reputation is critical. You need to be someone others want to hang out with, on and off the water.” To illustrate the point, Hurd cites the observation a competitor’s coach once made about Tabor’s sailing team. “He said our guys were ‘politely vicious,’” Hurd recalls with a chuckle. “I took it as a great compliment. We wanted to win, but we were going to do it the right way.”

No one embodies the ideal of winning the right way better than Zander ’02 and Jesse ’06 Kirkland. “Tabor has attracted a great many gifted Bermudian sailors over the years, and the Kirklands are outstanding examples,” remarks Hurd. Student sailors from Bermuda have a good sense of their sailing skills and a good sense of self, he explains. “They know what they’re good at and what they need to improve, they accept coaching, and they exude a leadership quality.”

The Kirklands exemplified the Bermudian sailing tradition during their time at Tabor, and in 2008, they decided to extend their commitment to the sport and make a bid for the 2012 Games together in the 49er, a two-person racing dinghy and the newest boat in the Games. “It was an exciting boat—cuttingedge and at the time—and given our size and desire to compete, it worked well for us,” Jesse explains. “The 49er was the Ferrari of the Olympics,” agrees Zander. “It was very athletic, went fast, and had lots of crashes.” Indeed, the boat’s characteristics prompted the brothers to dub their Olympic campaign “Taming the Beast.” While the brothers were already accomplished sailors when they set their sights on the Olympics, they admit they did not fully appreciate the demands inherent to the campaign until they were in it. “Our dad taught us to sail when we were kids— I was racing by age 12 and Jesse was at it by age 8,” says Zander. In fact, he notes, Jesse was such a natural that he became something of a child prodigy in Bermuda sailing circles. Still, learning to sail the 49er competitively was humbling. “We succeeded because we’re stubborn and gritty and possess an inner belief in ourselves,” says Zander. “You’ve really got to want it and no one’s going to give it to you—you need tenacity.” Jesse concurs. “You’ve got to let the passion carry you for a while—that’s what fuels the discipline and the sacrifice.”

But the brothers also realized that grit alone wouldn’t carry the day. To fund their Olympic dream, they needed to generate excitement around their venture, secure sponsors, and convince others to believe in their dream and join them on their journey. So, they treated their campaign like a start-up. “We wrote a business plan, secured seed money, got a boat, and set milestone goals,” recalls Zander. They sought advice from others who had done similar campaigns and got creative to secure world-class coaching. “When you’re starting out, you have a bit of a chicken-and-egg problem—you need the best coaching you can get to improve your skills and prove yourself, but you can’t afford a coach without having a campaign budget to draw upon and you typically don’t get that until you get results, so it’s tough to break through in this regard. Biggest advice here is to be a sponge when hanging out with your competitors in the boat park and prioritize coaching for every spare dollar you don’t desperately need for the boat or logistics,” says Zander.

The brothers got creative, sharing a top-tier coach with a Mexican team for a time to reduce costs, and trained relentlessly, qualifying for the Olympics with a top-10 finish in the 2012 World Championship in Croatia. “Getting to the starting line

of the 2012 [London] Games was a huge battle,” adds Zander. “I had never been tested so hard,” Jesse concedes. “Everything is stressful—the workouts, the fundraising. You’ve really got to dig deep and lean into the passion.”

In the end, the brothers didn’t have the Olympic event they would have hoped for, but both insist they wouldn’t trade the experience. “Losing was tough at that event, but our crescendo in that lead-up in late March through May of 2012, which secured our qualification, were (some) of the best months of our lives. To say we got top 10 at the world championship in an Olympic class in an Olympic year was a huge achievement for us,” says Zander. “We were sailing great and really in sync. We saw some high highs and low lows, and we came away with some incredibly special shared memories.” Jesse echoes that assessment. “Being able to compete in the Olympics with Zander was very special—from here on out, everything is a breeze for us.”

The brothers also note that the lessons they learned while sailing have transferred handily into their post-Olympic lives. “The ability to articulate your mission and evangelize for your cause is a valuable skill, whether you’re running an Olympic campaign or pursuing start-up capital,” observes Zander, today a strategic partnerships manager, working with key relationships in the small business lending industry for Funding Circle. “And in business as in sailing, you learn that although things don’t always go to plan, you keep your head down and keep working.” Jesse agrees. “As an underwriter at Chubb, I need to stay poised while managing my responsibilities as well as work effectively in a team environment. Our Olympic run gave me the experience necessary to succeed in my career—I learned the importance of staying calm and continuing to execute, even in the face of adversity.”

Sailing legend Gus Miller ’53 is also intimately familiar with the importance of building relationships, training hard, and working smart, and he knows firsthand the extended benefits of a life spent on the water. “Sailing offers all kinds of life lessons,” he asserts. “The sport is an instrument of broad self-expression—you must master yourself before you can master the part of nature that is sailing.”

Miller has spent decades sharing the knowledge and experience he has gleaned from countless hours on the water. A coach spanning eight Olympiads, he has taught sailors from 49 countries and all the Olympic and Pan American classes except the 49er. He is legendary in the Finn Class—a notoriously demanding boat—taking first in the 1992 Finn Gold Cup race at the age of 57. Now in his 80s, he still sails regularly.

“My father was very involved in sailing and introduced me to the sport at the age of three, teaching me to steer by wading along the beach pulling a small punt that had steering ropes attached to a yoke on top of the rudder,” shares Miller. “I quickly graduated to a punt with leeboards, a small Sliding Gunter rig, and a tiller, but on my first solo sail, I had to beach the punt and walk back so an adult could show me how to sail upwind,” he recalls with a chuckle.

This ability to explore, experiment, and learn is one of the things that has kept the sport fresh all these years, says Miller. “You develop an intense intimacy with the sky, wind, clouds, waves, and landforms,” he observes. “I grew up in a culture of seamanship where acceptance was being called a good seaman who was able to take care of the boat and himself.” Sailing a Finn is very physical, but you must also be alert to what’s going on around you with the weather, he explains. “If something needs to be taken care of, you must address the situation immediately or you could be in real trouble. It’s like a deep meditation—you let go of everything else and exist in the moment.”

Relationships are also an integral part of the sport of sailing, Miller continues. “I’ve had the opportunity to enjoy the shared intimacy of sailing with many exceptional people around the

photo: Robert Deaves

photo: Finn Class Archive

world.” The sport offers common ground and demands that participants get down to basics very quickly, he explains. “The Finn has a highly evolved hull, with a powerful, sophisticated rig that races well in anything from a whisper of air to rough water and high winds; an awful lot of smart, good sailors get in the boat. We race hard, but we’re very friendly and open with one another on shore. At the end of the day, we’re really competing against ourselves rather than each other.”

Asked what advice he would offer young Olympic hopeful Thad Lettsome ’20—currently working to qualify for the British Virgin Islands Laser class team at the 2024 Summer Games—Miller doesn’t hesitate. “Enjoy the journey you’re on for all it’s worth, regardless of the numerical result,” he counsels, “because that’s what you will remember.” In the end, the biggest challenge Lettsome or any other competitor faces is himself, Miller concludes. “To succeed, you must stay well-motivated, train yourself to accomplish excellence, and share the joy of your experience— you can’t do it without others.” 

MILLER’S LIST OF SUGGESTIONS TO OLYMPIC HOPEFULS:

Learn to keep centered whenever obstacles occur and find a way to achieve the mission or task.

The Olympic chase inspires people to do and say stupid things—don’t get sucked in.

Be willing to train with those who are better than you are so you can rise to their level.

Practice your weak points much more than your strong points.

Learn to be your own coach by keeping a detailed written training log and reviewing it often.

Have a clear goal for what you want to accomplish after the Olympic journey.