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Lessons from the Kentucky Derby

May 16, 2024

Earlier this month marked the 150th anniversary of the Kentucky Derby. Known as “The Most Exciting Two Minutes in Sports,” it’s the oldest continuously-held sporting event in the United States! While it has been rescheduled to different parts of the year on a few occasions, it has never been canceled in its entire history.

Over the last century-and-a-half, the Derby has seen its fair share of upsets, memorable moments, and photo finishes. Every year, twenty horses and their jockeys gallop at a neckbreaking pace for a little over a mile, each striving for a goal they have planned for, practiced for, and dreamed of for years. While reading about them, I realized the race can teach us all a few lessons about how to reach the finish line of our own dreams.

1. SUCCESS REQUIRES PLANNING AND PREPARATION TO ENSURE PERFORMANCE. When we think about our most cherished goals, we all love to close our eyes and picture ourselves enjoying a cocktail on the beach, surveying the landscape from the top of a mountain, or holding the winner’s trophy. What we really should be picturing, though, is what it takes to get there. You see, while horses race the entire length of the Derby track in a little over two minutes, it takes two years to actually win.

It all starts when the horse is young. A horse must be three years old to race in the Derby, so early on, they must be well-bred, well-fed, and well-housed. Then, when they turn two, the actual training begins. First, they are trained to follow their rider’s commands. Next, they are taught how to gradually build up speed. Then, the focus turns to building stamina. Finally, horses will compete in less high-profile races to gain experience. All these steps must go right for a horse to stand a chance at winning the Kentucky Derby.

We have to follow a similar process to reach our financial goals. We must train ourselves to develop good financial habits. We must save and invest consistently, gradually building up our wealth for when we need it most. We must have a step-by-step plan that details exactly what to do and when to do it…so that we can take that dream vacation, build that dream home, start that dream business, enjoy that dream retirement.

Racing in the Kentucky Derby is simply the last step in a long and methodical process. Our own personal race requires nothing less.

2. NEVER LET ANYONE DEFINE WHAT YOU CAN ACCOMPLISH. As a financial advisor, I often meet with people who believe that certain things will simply be out of their reach forever. No matter how much money we have, society often tries to fit us into boxes based on background, race, gender, job, social status, or any of a dozen other things.

The Kentucky Derby teaches us that this is all nonsense. Anyone can accomplish their dreams if given the opportunity. For proof, take the story of 44th winner of the Kentucky Derby, a horse named Exterminator.

Exterminator was owned by Willis Kilmer, a man who didn’t think very highly of his horse. He frequently referred to Exterminator as “a goat” or a “truck horse.” In his eyes, all Exterminator was good for was to give the “real” racehorses something to practice against. But when the 1918 Kentucky Derby drew near, Kilmer’s main horse picked up an injury. Despite having no other choice, Kilmer still had to be convinced to enter his “goat” into the race. Even the jockey grumbled as he mounted the unfavored horse, who had not actually raced since the age of two.

You can probably guess where this is going. That morning, the track was muddy from persistent rain. Probably the only person who felt confident was Exterminator’s trainer, who knew the horse had heart, intelligence, and a tremendous work ethic. When the flag went up, the horses were off…and two minutes and ten seconds later, Exterminator became one of the unlikeliest of winners in the competition’s history. He would even go on to win fifty more races before retiring at the ripe old age – for a racehorse – of nine.

The lesson: You alone are in control of your financial future. No matter who you are or where you come from, you have the ability to reach whatever goals you set for yourself. Never let anyone tell you otherwise!

3. SUCCESS TAKES TEAMWORK. While we rightly give the horse most of the credit for winning the Derby, it actually takes an entire team of professionals. There’s the jockey, of course, but also the trainer, assistant trainer, grooms, veterinarians, stable hands, farriers – they make horseshoes – and many more.

Financial success comes from teamwork, too. No matter how much money a person makes, they will always benefit from the help and support of family members, friends…and yes, financial professionals like advisors, tax preparers, estate attorneys, and more. The lesson here? When working toward your financial goals, you don’t have to do it alone. Always make sure you have a good team that can help you reach the finish line.

4. SUCCESS TAKES PERSEVERANCE. In horse racing and in life, it’s not always the most talented person who succeeds. Or the smartest, or the most well-connected. It’s the one who simply never, ever quits. For example, take the story of a horse named Giacomo. When the 2005 Kentucky Derby began, Giacomo began slowly. For much of the race, he ran near the back of the field. Even after three-quarters of a mile, he was still in only 18th place. But then, something happened. One by one, the other horses began to retire. One by one, Giacomo began passing his competitors. As his jockey put it, “He just kept grinding and grinding and wouldn’t stop until he got it.” And guess what? He got it.

There will be many obstacles in your way as you work toward your financial goals. At times, you may feel like you’re behind schedule. But it doesn’t matter how you start. It only matters that you keep going.

5. YOU NEVER KNOW WHEN YOUR OPPORTUNITY WILL COME. The horse wasn’t even supposed to be in the Kentucky Derby. But on the morning of the race, another horse had to be removed from the competition at the last minute, giving an opportunity to a little-fancied colt named Rich Strike. What followed was the single biggest upset in the event’s history. Shocking every expert and onlooker, Rich Strike won the 2022 Kentucky Derby despite being given odds of 80 to 1.

In life, we never know when an opportunity will come around. That’s why we must always be ready for it. If you are prepared, if you are confident, if you have the right team around you, and if you never give up, you can seize even the most unexpected of opportunities…and prevail no matter what the odds.

I hope you enjoyed this little look at the history of the Kentucky Derby. As you run your own race, always remember that Tina, Kara and myself are here to help…and that we are cheering for you all the way!