Go Big with Gib Podcast
Go Big with Gib is a podcast for professionals, business owners and entrepreneurs to talk about their big wins.
Go Big with Gib Podcast
Ep 92. How Jesse Itzler Built a Life Without Limits
We share why Jesse Itzler’s nonlinear path—music, aviation, endurance, ownership—works because it’s guided by better questions, not a stricter plan. The takeaway is simple: stack experiences, build culture before profit, and design a life that lets you choose.
• unconventional career arcs that compound into advantage
• running business like an ultra marathon
• culture as a performance multiplier
• humility as an operating system for learning
• identity stacking across work, family, sport, creativity
• freedom and optionality over status and valuation
• permissionless action through small, repeatable experiments
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Welcome to the Go Big With Gibb Podcast, where we talk to professionals, business owners, and entrepreneurs about their big wins. Welcome back to Go Big With Gibb. I'm your host, Gib Irons. Today we're diving into the story of someone who's built a life that defies all convention, Jesse Itzler. Now, Jesse's resume doesn't fit in any one box. He signed a rap deal, wrote an anthem for the Knicks, co-founded a billion-dollar private jet company that Warren Buffett later acquired. He's an endurance athlete who ran 100 mile races. He's lived with Navy SEALs and even with monks. Jesse co-owns the Atlanta Hawks with his wife. That's not a linear path. That's a life of curiosity, courage, and saying yes when most people would say no. So what ties it all together? It's a refusal to accept normal. Jesse didn't follow a formula. He asked different questions. What if I ran my business in the way I run an ultra marathon? What if I built culture before profit? What if I leaned into humility as a strength? That mindset turned every pivot from music to aviation to coconut water into a launch pad. And here's the lesson for you and me. Success doesn't have to look one way. You can be a professional, a parent, an entrepreneur, an athlete, a creator at the same time. The real win isn't just the money. It's the freedom to design a life on your own terms. When you stop asking for permission, when you stack experiences instead of accolades, that's when life begins. That's when life becomes unforgettable. Because sometimes the more unconventional path, the more extraordinary the outcome. Thanks for tuning in to this episode of Go Big With Gibb. I'm Gib Irons reminding you to stop following the herd and start building a life that's truly yours. Thank you for listening to this episode of Go Big With Gibb. If you haven't already, go follow us on social media at GibIons. We'll see you next time.