What the Kentucky Derby Teaches About Winning

By Team Hirschel

This weekend, millions will tune in to the Kentucky Derby, a race steeped in tradition, glamour—and yes, gambling. But behind the champagne, big hats, and fast horses lies a brutal truth that businesses should take to heart: Winning isn’t luck. It’s preparation, strategy, and risk management.

At the Derby, the winning horse isn’t the one who “got lucky.” It’s the one with the right bloodline, the right trainer, the right jockey, and the right conditioning. Months, sometimes years, of strategy and preparation go into those two minutes on the track. Business is no different. Companies that bet on luck instead of planning their moves usually find themselves watching from the sidelines.

Build the Right Team
No horse wins the Derby alone, and no business wins big without the right people. Owners choose trainers who have a track record of success. Trainers pair their horses with jockeys whose style matches the horse’s strengths. It’s a highly strategic selection process.

In business, you need to be just as intentional. Hiring isn’t about filling seats. It’s about building a team where each player’s strengths amplify the others. You don’t need a stable full of superstars; you need the right combinations of talent, chemistry, and drive. Bet on people who can take you across the finish line, not just look good on paper.

Play the Long Game
A Derby winner doesn’t peak overnight. Successful horses are carefully managed from the start—choosing the right races, building stamina, and avoiding burnout. They’re developed with the end goal in mind.

Businesses that chase short-term wins at the expense of long-term strategy often flame out. It’s easy to get caught up in the next shiny opportunity, but true success comes from consistent investment in the things that matter—your people, your culture, your customer relationships. You can’t sprint your way through a marathon.

Manage Risk Like a Pro
Betting on the Derby is gambling. Competing in it is calculated risk. Owners and trainers assess bloodlines, analyze performance metrics, and decide where and when to enter their horses. Every decision weighs reward against risk.

Smart business leaders do the same. Expansion, product launches, new hires… all require calculated risks. It’s not about being reckless. It’s about doing your homework, preparing for different outcomes, and knowing when to pull the trigger.

Luck Is What Happens When Preparation Meets Opportunity
The horses that make it to the starting gate didn’t get there by chance. They earned it through relentless preparation, smart strategy, and smart risk-taking. Business leaders who want to build lasting success should be taking notes.

This Derby weekend, enjoy the spectacle and place your bets if you want. But when it comes to your business, leave luck at the door—and bet on preparation instead.