In this episode, I’m thrilled to sit down with Jesse Itzler, an unstoppable entrepreneur, ultra-endurance athlete, and master of unconventional experiences. Jesse's journey is built on facing down fear, embracing challenges, and doing what most people would never attempt. From creating Marquis Jet and selling it to Warren Buffett’s Berkshire Hathaway, to venturing into the unknown time and time again, Jesse’s story is proof that success is found on the other side of risk.

Jesse dives into the art of tackling “the wall” — that point where fear, doubt, and hesitation threaten to stop you. He talks about how he built a mindset that not only pushes through but thrives in uncertainty. When he realized he wanted to experience private jet travel but couldn’t afford it, Jesse and his partner went straight to NetJets with nothing but a vision and unshakeable conviction. Against the odds, they secured a deal with Buffett’s team, setting the foundation for what became a game-changing business.

We also get into why Jesse believes routine kills creativity and how he designs his life around extraordinary experiences. He shares his practice of "Kevin's Rule," a commitment to creating meaningful experiences every two months. Jesse has made it his mission to build a “life resume” filled with unforgettable moments and deep connections.

This episode is packed with strategies to turn ambition into action. Jesse’s journey reminds us that life is too short to play it safe. Start building the life you want—one bold step at a time!

Learn more about your ad choices. Visit podcastchoices.com/adchoices