Entrepreneur Jesse Itzler Says Winners Are Bold, So Rip Up the Playbook

The author and entrepreneur was the second-day keynote speaker at The HFA Show in San Diego.

If you ripped up the playbook, how would you do your business? Jesse Itzler, business entrepreneur and author, asked that question during his keynote address yesterday at The HFA Show in San Diego.

Sponsored by Matrix, Itzler’s keynote, “The Spiritual Billionaire,” revealed several lessons he learned during his life. One of those lessons stemmed from his father’s mastery of checkers and unwillingness to let Itzler win a game as a child. It taught him how to deal with disappointment in life and business, Itzler said.

Armed with that early lesson in resilience, Itzler pushed through a string of setbacks that would have stopped most people. He started up multiple businesses that failed, including one in which he cleaned meat trucks. He worked as a kiddie pool attendant. He slept on friends’ couches as he tried to launch a rap career. He finally launched a successful business—Marquis Jet—that he sold to businessman Warren Buffet after the company earned $5 billion in cumulative sales over 10 years.

He has founded multiple businesses and has had five successful exits.

Because of his unwillingness to be defeated by failure, he learned to embrace deviation from the plan.

“The things that had the biggest impact in my journey are things that were not in my business plan,” Itzler said. “They were opportunities that I just took by doing things differently. By being bold. The universe rewards the bold.”

He often challenges his employees with this question: If no one taught you how to do your job, how would you do it?

He asked the audience these questions: “If you ripped up the playbook that everybody in the industry has been using for the last 50 years, how would you talk to your customers? How would you retain them? How would you welcome them into your fitness facility? How would you write thank you notes? What would your fitness club look like?

“That’s where innovation comes from. That’s where destruction comes from. That’s where separating yourself from the competition comes from.”