Episode #28 Tyler Boyd Betting on Yourself and Your Own Skills

Every year, the Masters Water Ski tournament is held in Callaway Gardens in Pine Mountain Georgia. It is THE most prestigious tournament in water skiing. This year, my friend Cyndi Benzel was chief judge and asked me to be the judge’s assistant. During the officials meeting the first night we got there, I ran into Tyler just to say hi. We have been connected on Linkedin for years -  because water skiing is that kind of sport. You just connect with everyone involved in the sport.  

Somehow Tyler and I started talking business and leadership and books that changed our lives.It was one of those moments where I wanted to capture the conversation – so we set the earliest date we could to record this podcast. 

This conversation gets going very quickly. Before we are five minutes into it, Tyler starts sharing some of his ideas on leadership and performance. He was deeply affected by Carol Dweck’s book Mindset and Annie Duke’s book Thinking in Bets. Both caused him to think differently – and act differently - and those themes are woven into this conversation. 

We also cover a lot of other ground on his thoughts on applying his life principles to investing and to sports.  

Of course, the conversation would not have been complete if we didn’t talk about the Master’s and some of the incredible stories from the event a few weeks ago. One thing I learned without a doubt: Tyler pours his heart into giving every athlete their moment in the limelight. I also learned how he has spent his whole life preparing to be behind the mic, whether in water skiing or announcing football. I was captivated by his stories about he learned to be so good on the microphone.   

Here’s what he has to say about himself. 

Tyler Boyd started water skiing as a child 30 years ago. His exceptional speaking skills gave him the motivation to become an announcer for water skiing events over ten years ago. For the last three years, he was the commentator for the Masters of Water Skiing. Tyler has also spent time announcing football events for Houston Baptist University. 

A licensed attorney, he brings exceptional speaking and negotiating skills to the table, along with a high level of focus, creativity, and value to every interaction. He stands out from the crowd by combining talent and passion in his professional pursuits. As a Houston attorney, he handles a wide range of legal issues in commercial, contract, business, and employment law. 

Tyler is a four-time USA National Water Ski Champion and remains active in the sport where he continues to compete. In his free time, Tyler enjoys traveling with his wife and three children, researching, skiing, diving, biking, and working out. 

Additional Links:

Jump Thinking 

Annie Duke – Thinking in Bets 

Carol Dweck – Mindset 

Warren Buffett 

Charlie Munger 

Berkshire Hathaway 


Andy Mapple  


Masters Water Ski 

Freddy Krueger 

Freddie Winter 

Joel Poland 

Chelsea Mills 

Jon Travers 

Matt Rini 

Hugh Jackman on Tim Ferriss Podcast 

Patricio Font 

Wayne Grimdich 

Will Mills 

Matteo Luzzeri 

Dano the Mano 

Britt and Tawn Larsen 

The Water Ski Broadcasting Company 

Wade Cox 

Corey Vaughn 

Tony Lightfoot 

Marcus Brown 


Waterski Nation 

Waters Ski Nationals 

Liz Allen Reed 

Jimmy Siemers 

Preston Fish – Podcast