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Dare to Win

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Wisdom from Jim Kilroy's book Kialoa US-1 – Dare to Win:


Leadership is not being obviously dominant. It is not being hard on your crew. It is a show of strength in maximizing the talent and participation of all of those aboard, with a common focus on the primary objective, sailing hard and fast, and managing the variable weather and sea conditions.


As I built a business, I found it essential to develop techniques to motivate my associates. I asked for and tried their ideas; gave them broader responsibility and authority; and requested their input on how to create new opportunities. It was a great and mutual success. As a result, I gained more free time for other activities.

I found that our clients were exceedingly interested in following and even participation in the sport of sailing and other projects in which I was involved. I would take them sailing and some clients would even join us as racing crew. They became enthusiastic about the decisions and teamwork required in racing and cruising. Lifetime relationships were established along with mutual confidence.

Character and leadership count. They are essential ingredients to successful sailing and successful business.

In business, and much of life, focus is essential to victory. We would have our crew work together to develop individual and collective focus for every maneuver.


While at sea, there is much time for reflective thought about life, about family, about business, about the future and about your true objectives. It’s an environment that cultivates fresh ideas about how to approach problems and issues, and above all, to sort out which are the important matters and which are the non-issues.


One cannot enjoy the sea aboard a racing sailboat without being a participant. It is not a spectator sport for those onboard. And one cannot be at sea on a racing sailboat without understanding the essential mutual independence of your fellow sailors.

At sea, life becomes elemental. You become one with the simple beauty of the sky, of moonlit clouds, of the ocean’s rhythm, or reflections on the water, of phosphorescent waves. You also realize that you’re not in charge. You are part of that beauty, and yes, you are sometimes engaged in the violence of nature, as well. In coping with extreme conditions, two things are essential: teamwork, and facing reality. Sailing is like life. It teaches the essential necessity for humility in mankind.


(The unpredictability) is what makes yacht racing such a challenging, rewarding sport. You can race the same course a hundred times and never see the exact same conditions. How we play the cards Mother Nature deals us is what’s ultimately most important.


Aboard Kialoa, we didn’t pay our crewmen. They had to be accomplished in some other walk of life, not as professional sailors. We did have many recent college graduates sail with us, who had “temporarily deferred” an ongoing career. We let them know – as we did with all our crew – that they could sail with us as long as they were making defined progress in making and fulfilling a plan for their future. In the meantime, we welcomed their input and ideas on how to improve our performance and results. We’d try them in practice. Some were great, some didn’t work out – just like my ideas. But the very process was productive and inclusive, and in the end, the consistently good results spoke for themselves.

We’ve followed our crew’s post-Kialoa journeys and careers, which have been outstanding. Their many successes have been our rewards.


We divided the 24 hours into what’s known as a Swedish system. This called for three four-hour watches from 6 p.m. to 6 a.m. that would alternate: during one night, your watch would stand two four-hour watches; and the next night, one four-hour watch. The day was split into two six-hour watches.


About three quarters of the way through the (Molokai) Channel, . . . we caught the longest surfing ride imaginable. The entire crew was hooting and hollering. The bow wave was back at the main shrouds and fully five feet above deck level. There was a kind of eerie, harmonic singing coming from the hull and rudder, which seemed a dissonant mix with the more violent and tumultuous roar of the water. We were carried along in the outstretched hands of this mighty wave for a most unbelievable length of time, all the while the log was pegged at 20-plus knots.

— Jim Kilroy

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