Brad Gilbert & Sam Zell: working Hard & Having Fun
Coco Gauff is having one hell of a year at the US Open and, with that, a lot of attention has been paid to the newest addition to her coaching team, Brad Gilbert. Gilbert is famous in the tennis world having coached tennis greats like Andre Agassi and Andy Roddick to major wins. However, as a relatively new tennis fan, Gilbert’s name and approach was new to me.
Gilbert wrote about his tennis philosophy in the 1993 bestseller, “Winning Ugly: Mental Warfare in Tennis - Lessons from a Master.” He contends:
“...when you get down on yourself—start beating yourself up mentally—there are now two players on the court trying to take you down. And one of them is you.”
Key to Gilbert’s philosophy is learning how to win when you are playing “average” and far away from what you feel is your best. I’ve been inspired by just how much fun Gilbert seems to have with the game as he teaches his players what it means to do that. His practices are known to be relaxed and full of jokes. He takes his players to dinner and talks strategy. He doesn’t yell or focus on negativity. Instead, his focus is often on helping players see the positive and build confidence so they don’t become their own worst enemy on the court.
His approach had me wondering: How often do we make ourselves feel like having fun is off limits in pursuit of chasing our dreams?
It’s so much easier to believe that achieving them will require suffering and misery and beating ourselves up. And yet, when I think about what’s possible in business and in life when we allow for the fun, I immediately think of Sam Zell.
Zell is a famous real estate investor and entrepreneur who sadly passed away earlier this year. He is commonly thought of as the father of the public real estate investment trusts (known as REITs) and had a phenomenal knack for timing market cycles. In a piece for Barron’s following Zell’s passing, investor Oscar Schafer wrote this:
“Sam recognized the importance of having fun. He threw elaborate parties and told dirty jokes. He had a giant personality. He was a serious investor, but he never took himself too seriously. When he was negotiating the largest deal of his life—the $39 billion sale of his office REIT—he famously tempted one bidder with an email written as a poem.”
Zell also rode motorcycles, created t-shirts for IPO road shows that often reflected tongue in cheek jokes, and gave out musical boxes with customized lyrics in lieu of traditional holiday business gifts. I’ve read many biographies of successful business leaders and have read few that reflected a work ethic so infused with fun.
I’m not asking you to stop working hard. I definitely can’t promise that you’ll never be stressed again. But I do want to challenge you to have more fun with your work and chasing your dreams. Maybe you’ll have a breakthrough moment at your version of the US Open.
