Aquila Capital Partners

Austin &
New York City

5 Leadership Lessons I Learned from Competitive Sailing

It’s interesting how I got into sailing, which was completely accidental. My dad gave me a Sunfish at age 10, which is pretty easy to sail. I was scared to death to capsize it, but my dad wouldn’t allow me to sail on my own until I flipped the boat over then back up. When he showed me how, I realized, “I can do this on my own!”. It was a moment of independence, exactly like when you first learn to ride a bike. At age 11, I was invited to a racing clinic that got me interested in racing. Later that summer, I won one of the biggest regattas in Texas at the time, the Navy Regatta at the Corpus Christi Naval Air Station. At that moment, I realized I’d become as good as everybody else!

That race ignited a lifelong passion, and ever since, I’ve been racing boats, both large and small –– sometimes even out in the ocean for days in a row. I’ve learned countless lessons from sailing that I’ve used in leadership and business –– here are the 5 most valuable.

1. Confidence

Sailing taught me early on that I can conquer challenges, and gave me the confidence to take the lead and figure it out. This experience has instilled in me a valuable lesson: you can accomplish far more than you initially think if you’re committed and passionate. Our limitations are often a lot further away than we think, especially once we’re determined to achieve our goals. Putting your head down and focusing can lead to remarkable achievements. 

However, in business, just like on a boat, there needs to be a strong, confident leader in charge, directing, and guiding. But it’s essential to strike a balance: while leadership requires a certain level of independence, it’s also crucial to be collaborative and adaptable. Overly-confident individuals might find it challenging to fit within organizational frameworks, whether they are in leadership roles or as team members, since they tend to do things themselves instead of guiding and teaching. So while the essence of leadership stems from understanding how to accomplish tasks independently, the key is building and managing a team that works together effectively, ensuring that everyone is aligned in pursuit of a common goal.

2. Interdependence

Interdependent teamwork, not just regular teamwork, is paramount. Everyone on your team needs to be on the same page in order to succeed. If one person slips, the whole project is in jeopardy. This is especially true in sailboat racing where someone could get injured. For example, imagine your job is to be in charge of the line that helps keep up the mast. You forget to keep your line taut and the next thing you know, the rig goes down. You’re now out of the race and you may have hurt someone. Depending on the size of the boat, it may have also been an awfully expensive mistake (a million dollars).

3. Recognizing what high performance looks like

Being on a winning team means getting exposure to high performance regularly. A winning team is the outcome of preparation, training, and practice, practice, practice –– in business it is no different. You don’t show up knowing everything, you hone your skill set with time. You learn to evaluate your team and the environment and adapt accordingly. Like I mentioned earlier, this requires a strong leader and an interdependent team working in sync. People can try to describe high performance to you, but until you’ve experienced it for yourself, it’s difficult to fully grasp and attain. Once you have reached that level, however, you’ll always want to perform that way.

4. No one remembers who came in second

Like it was said to Queen Victoria when Britain lost the very first America’s Cup, there is no second place. This rings true in many industries in business where the winner takes all –– there is no prize if you lose a deal or contract, you’ve simply lost the deal. Strive for the win, but do it smartly with an exceptional team and airtight plan. When you get to the finish line, you’ll see that all the hard work, planning, and synchronization has paid off.

5. Resourcefulness

When you’re on the water, things don’t always go well, and you have to be resourceful and figure it out. Sailors have been navigating troubled waters since long before cell phones and GPS. Maybe your rudder breaks or the wind drops, you will have to figure out how to get in on your own. You find you’re also more captive to the environment, more in tune with it, when you need to solve a problem. These types of challenges as a young boy instilled a deep-seated sense of confidence and independence within me. It’s an exhilarating realization – when faced with daunting challenges, and you learn to rely on your wit and resilience, your confidence soars, making you all the more resourceful for future endeavors.

You don’t need to be a competitive sailor to learn and implement these tips — listening and absorbing valuable lessons from mentors and teammates can help you tackle your business in the most effective ways.

We don’t always realize it, but sometimes childhood hobbies and experiences teach us extremely useful lessons in business. In my case, my experience with sailing taught me that I can right a sinking ship, build and depend on an exceptional team, and lead that team with confidence to reach our goal. This is exactly what happened when I became CEO of a regional, $300 million underwriting organization that was nearly insolvent. With the right strategy and team, we were able to right the ship and became a $3.5 billion world leader after a few years.

Image by Artem Verbo from Unsplash.