Why Winners Win

Here's what the pros do, why they beat you, and how you can get there.

There’s a tendency in our sport to overcomplicate things, especially when it comes to stringing together a series of top finishes in a regatta. We wonder why our competitors beat us time and time again and chalk it up to better boatspeed, better sails, or maybe having a few professionals onboard. While some that may be true, the reality, however, is pretty simple: they win because they’ve learned by making mistakes. In my experience there are a few obvious things that winners do to win. In other words, the beat you because they . . .

Have Marks on their sheets and use them to repeat fast settings.

Speed is essential to winning in sailboat racing, and a big component of speed is how you trim your sails. Before the race starts, tune upwind with another boat and try different amounts of sheet tension on the main and jib. When you find the fastest trim, look at your marks on the sheets so you can repeat them off the starting line and again at the leeward mark. Having marks allows you to not only go faster, but also get your head out of the boat to look around for more wind and big lanes.


Do Practice Starts before each race to dial in their time and distance.

Top sailors know that time and distance is crucial to a good start, and that it’s difficult and requires practice. It is something that changes with wind and wave conditions and also line bias. As the pin gets more favored, for example, it takes longer to get to the line. If the boat is favored, closing speed is much faster. Therefore, top sailors do a few runs at the line before each start. With 10 minutes before the first warning, I like to start a 5-minute sequence and start near the committee boat at 3 minutes, and again at zero, that way you keep your watch set for the actual 5-minute gun but can get two starts during that 5-minute practice time.

Run Spinnaker Tapes as much as possible to avoid twisted sets.


Nothing seems more painful than setting your spinnaker with high expectations of a great run, and then having a massive twist. Simply running the tapes before each set helps avoid this painful and slow scenario.

Have Defined Roles on the boat and do the same jobs every time.

Most teams violate this simple rule all the time. When you are involved in someone else’s job you’re not only interrupting them, you are not doing your own job well. To win in sailboat racing you have to trust your teammates and let them do their job. To help alleviate the need to do others’ jobs, put people in positions where they have strengths. It’s also important to do the same jobs all the time, even when rigging the boat before racing.


Look for Wind more often than you do, and work hard to be in it.

When I sail with top sailors their biggest concern is “where is the wind.” After all, wind makes sailboats move, and more wind makes sailboats move faster. If you are impressed with a top sailors boatspeed, I guarantee a large portion of that speed is due to them putting themselves in more wind and working hard to have big lanes. To find wind, look around for darker texture on the water, wear polarized sunglasses to reduce glare, and get as high up in the boat as possible. Once you’ve spotted the wind, make it a priority to put your boat in it.

Have A Lane all the time, and know it equates to speed.


Since we know that having more wind is crucial to doing well, make it a priority to sail in big fat lanes. Wind likes to go up and over big groups of boats, and sails create wind shadows. So, if you are in a tight lane, or sailing in a pack of boats, you are guaranteed to have less wind. Thus, make it a priority to have big lanes. In doing so, you have to anticipate what others will do and base your tactics on keeping a nice big lane.

Sail Toward The Mark as much as possible.

When you’re racing, where are you actually going? The answer is to a mark or the finish line. Therefore, after putting their boat in the most wind on the course, top sailors focus on sailing toward the mark. I always teach to “lead on the long tack,” which implies you should sail toward the mark. If you can lead others while doing so, even better. While sailing toward the mark, you’re setting yourself up for more wind rolling down the course, and/or the next shift. The goal is to be in wind and sail toward the mark. Use your compass to help you sail the lifted tack upwind and the headed jibe downwind. Lifts always lift you toward the top mark, and headers head you toward the bottom mark.

Research The Starting Line more than you before the start.

Because starting well allows you to have a big lane and go the way you want—toward more wind and the mark—starting is critical to success. Take a page from match racers and research the heck out of the line. If you ever watch match racers they run the boat and pin laylines over and over while practicing time and distance. They also run the line and time how long it takes. They also “grade the line” by repetitively going head to wind and noting the line bias.

Practice More, even if it’s just an extra 30 minutes on race day.

Practicing helps you define who does what on the boat and figure out how to get the sails up and down without issues. Most people don’t make the time to practice as much as needed because of work and family obligations so do the best you can.

An hour of sailing beside the yacht club after work is better than nothing. And, if you can’t make that happen, leave the dock 30 minutes earlier and spend a little more time warming up before the first start. You can even practice a little on the way in from sailing to set yourself up for the next day. When practicing, focus on sets, douses, tacks, jibes and time and distance.

Have Team Chemistry and resist the urge to complain and condemn.

The championships I’ve won were always with teams that got along well. If you have internal drama and smaller “alliances” forming with people talking behind each other’s backs, it’s going to be very difficult to succeed. Being on a team is tough and every team has issues, so I’m not suggesting everything has to be perfect, but try to put a team together that respects each other, tries to have fun, and avoids blaming each other when things go wrong.

Avoid Drama on the racecourse and visualize all low single-digit finishes.

The third rule of tactics, beside sailing in more wind and sailing toward the mark, is to keep it simple. Keeping it simple means don’t tack or jibe too much, and avoid protests and clumps of boats. Try not to be the boat sticking it in at the weather mark on port tack layline, or the boat barging at the starting line or leeward mark. Keeping it simple requires discipline and good judgment, and is crucial to doing well. To help make solid decisions I like to visualize a scorecard of all low single-digit numbers, meaning no “letters” like OCS or DSQ. When thinking about your regatta, picture a clean, almost boring event. No drama, just good starts, big lanes, and clean mark roundings.