Thoughts on Leadership: Lessons from the Kentucky Derby

By Gino Blefari

This week my travels find me participating in my typical WIG calls on Monday, joining an early Berkshire Hathaway Energy call on Tuesday, and on Wednesday, going to the California Theatre in San Jose, California for The Dwight Clark Legacy Series: Playmakers. The event featured round table conversations with San Francisco 49ers greats, including Fred Warner, Bryant Young, Jerry Rice and John Taylor. Today, I sat down to write this post to you.

Over the weekend I was entranced – as I am each year – by the Kentucky Derby. (Berkshire Hathaway HomeServices network members will remember 2022 when the network took over historic Churchill Downs for an incredible Sales Convention celebration.) I love the Kentucky Derby not only because it’s exciting, but also because it always provides important leadership lessons. Here are a few from the 2023 races:

Read more: Thoughts on Leadership: Lessons from the Kentucky Derby
  • You can win against all odds. Mage entered the Winner’s Circle as a new champion in the 149th year of the Kentucky Derby, racing against tremendous 15-1 odds and eventually, getting that coveted garland of roses. Before the race, Mage was far from a favorite. In fact, he only had three starts this spring. Mage’s success proves that it doesn’t matter what the odds are, what happened in the past or whether people doubt you. Only you can make the outcome yours.
  • You only fail when you fail to keep going. The jockey riding Mage, Venezuelan Hall of Famer Javier Castellano, was far from a trending name in the race. He was 0-15 before he broke his streak by this Kentucky Derby win. “I never give up,” Castellano said. “I always try hard to do the right thing. It took me a little while to get there. I finally got it.”
  • You can use your critics as motivation. As Castellano was in the jockey’s room preparing for the race, he said he looked up and saw NBC’s pre-race broadcast where the network had written: “0-15, Javier Castellano” below his name. When he saw the not-so-encouraging stat, Castellano told himself, “This is the year … I’m going to win the race.” Well, we all know what happened next.
  • You must write down your goals so they become etched into your subconscious. When asked, Mage’s assistant trainer and co-owner Gustavo Delgado Jr. said the win was a fulfillment of a dream – or we could say a Wildly Important Goal – that he had written down a year-and-a-half ago. Delgado said: “I wrote a note: ‘We’re going to win the Derby next year.’” Then, he won. Delgado’s story reminds me of my own start in real estate and a box I still have in my storage closet that has my old 3×5 index cards inside. On each card, I had written out my goals and affirmations. Re-reading those years later, it’s surreal to me that they all came true. As an example, in 1985, I set a goal of making $60,000, noting that it would be in direct proportion to the service I give. Even though it took me six months to get my first pending sale, I still hit my goal by the end of the year.
  • You can’t stop until you reach the finish line. In the backstretch of the race, Mage focused on the horse in the leading position and passed him at the eighth pole, going on to win the Kentucky Derby. Imagine if he gave up when he was behind? Instead, Mage didn’t stop until he was ahead of them all. “He’s a little horse with a big heart,” Castellano said.
  • You should always remember those who support you on your way up the ladder (or around the racetrack) of success. According to, Castellano’s win was as much about loyalty as it was about fate. For the last five years, Castellano has been sponsored by restaurateur Jeff Ruby, proudly sporting the Jeff Ruby Steakhouse brand. But in a tweet by Ruby, the restaurateur said Castellano almost didn’t wear the brand during the race. Why? Castellano was originally set to ride a horse called Raise Cain but the owners of that horse told him “at the eleventh hour” that he couldn’t wear the Jeff Ruby Steakhouse pants. Castellano said if he couldn’t support his sponsor, he simply wouldn’t race. He was going to give up a chance to be in the Kentucky Derby! Then in April, Castellano switched from Raise Cain to Mage so he could represent his sponsor. And when he triumphantly crossed the finish line with Mage, he was proudly sporting the Jeff Ruby Steakhouse pants. (Castellano also went to dinner at Ruby’s Louisville steakhouse after the win, where diners gave him a well-deserved standing ovation.)

So, what’s the message? Berkshire Hathaway HomeServices California Properties President Martha Mosier said it best when she shared her experience attending the Kentucky Derby this year. From the horses to the friendships to the leadership lessons this race contains, it is truly, as she wrote: “The experience of a lifetime.”

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