This weekend, we were down in Virginia Beach at the annual paella party of our good long-time friends.

At some point, everything stopped. Because it was time for the Kentucky Derby.

To me, the Derby is the same each year. For about two minutes, everyone becomes a horse racing expert. People pick winners, talk odds, act like they’ve been following these horses for months.

Others sit it out. Some question the tradition altogether over a whole host of reasons.

Regardless, the race goes on and has for 152 years!

And if you watched closely, the 152nd running of the Derby tended to say more about investing and life than people expect.

It’s Not Where You Start, But Important That You Do

The Derby rarely plays out clean. Take the prerace. Horse Great White, ridden by jockey Alex Achard, appeared to get spooked and never even started. Never even getting the chance to win. Lesson: To finish, you must first start.

As the race started, certain horses jumped out to the lead. As is common, the early leaders faded. Lesson: It is not where or how you start.

Favorites disappoint. Lesson: Run your own race. If outcomes were obvious, there’d be no need to take the risk of running the race in the first place.

And this year, in a particularly exciting finish, Golden Tempo, a 23-1 longshot came not only from behind, but from dead last, and made a BIG move when it mattered.

Lesson: You don’t always see it early. Well at least I don’t. But if you don’t quit or get forced out and stay in the race, you still always have a chance.

Investment markets feel like that.

What’s leading today won’t always lead tomorrow. The narrative that feels obvious now is usually the one that gets tested next.

Right now, parts of the market feel like horses sprinting too early—priced for a perfect race, with very little room for anything to go wrong. While other parts seemingly down and out make a seemingly miraculous move of late.

That doesn’t mean they won’t win or that they will win.

Unlike the Derby which ends quickly, with investing, the race is longer than it looks.

Down Doesn’t Mean Out

In the Derby, horses get boxed in. They lose position. They fall behind.

But they’re still in the race. In investing, those stretches just last longer.

Underperformance. Drawdowns. Periods where nothing seems to work.

That’s not failure. That’s part of the process.

Because even if you’re right in the long run, being forced out in the short run ends the game.

Most investors don’t lose because they picked the wrong thing. They lose because they couldn’t stay in it.

The Race Evolves. The Preparation Remains Steadfast.

One of my favorite storylines this year was another barrier continuing to fall— Cherie DeVaux became the first female trainer to win the Kentucky Derby. You have love to see female trainers gaining ground in a sport that historically didn’t make space for them.

To my daughters a quote from Cherie "By doing this, I am inspiring other young women, and that, I am proud of," DeVaux said. "Women —young, old, whatever age — can look up to me and say, 'If she can do it, I can do it." Kai and Sam, go change the world and don’t let anyone tell you otherwise for any reason.

Preserve values and respect traditions but challenge them as well. Challenging the status quo is a good thing. Because not everything about traditions deserves to be preserved.

The Derby evolves. It has to. But not everything changes.

The preparation. The discipline. The respect for the process. The understanding that the race is longer than it looks.

Those stay. Same in investing. You don’t preserve everything.
You preserve what works and evolve what doesn’t.

Timing Matters More Than Speed

The Derby isn’t about always being the first horse. It’s about when you make your move.

Too early, and you fade. Too late, and you run out of track.

Investing works the same way. It’s not about always being right immediately. Or getting there fast. It’s about structuring things so you can act when the opportunity is actually there.

That requires patience and restraint. Two things that don’t show up on a statement.

Final Thought

The Kentucky Derby lasts about two minutes.
Investing lasts decades.

The winner is rarely obvious at the start.
The middle is where conviction gets tested.
And the finish only matters if you’re still in the race.

Right now, many investors are leaning into momentum… pressing, chasing, even adding leverage to keep up.

But very few are asking the more important question:
What happens if the pace changes?

That’s where races are actually decided.

Not at the break.
Not at the headlines.
But in the ability to stay in the race when conditions shift.

Because in investing, like in life, starting matters but staying in the game is everything.ⁱ

Lesson: “To finish first, you must first finish.” — Rick Mears

If you’re thinking more about how your financial plan holds up across the entire race—not just what’s winning right now—that’s where we spend our time.

 ⁱ https://www.memberswealthllc.com/insights/from-nixons-inflation-to-trumps-fed-pressure-can-investors-survive-the-short-term   

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About the Author

Dane Czaplicki, CFA®

Dane Czaplicki is CEO of Members’ Wealth, a boutique wealth management firm that offers a comprehensive approach to serving individuals, families, business owners, and institutions. The firm’s goal is to preserve and grow its clients’ wealth to endure over time, while thoughtfully evolving its strategy to suit an ever-changing world. With over 20 years of wealth management experience, Dane and the Members' Wealth team thrive on bringing clarity and confidence to clients' unique situations. He believes everyone needs sound financial advice from someone whose interests are aligned with theirs, and is determined to put service before all else.

Dane received his MBA from The Wharton School of Business at the University of Pennsylvania and his bachelor’s degree from Bloomsburg University. Outside work, he enjoys spending time with his wife and kids, hiking and camping, reading, running, and playing with his dog. To learn more about Dane, connect with him on LinkedIn.

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