Founders Files: Jessie Itzler

November 15, 2024

The Unstoppable Force of Creativity

Imagine a guy who rapped in front of stadiums, co-founded a private jet company, lived with a Navy SEAL for 31 days, and is now redefining endurance culture. That’s Jesse Itzler, a man whose life feels like a string of impossible adventures stitched together with grit, vision, and sheer willpower.

From Rapping to Reinventing Private Aviation
Jesse Itzler wasn’t your typical college graduate. Born in Roslyn, New York, in 1968, Jesse’s early life gave no hint that he’d soon become an entrepreneurial powerhouse. A kid with a wild imagination and a relentless drive, he often did things differently, even as a student at American University.

After college, Itzler broke into the music industry as a rapper—yes, a rapper. Under the name Jesse Jaymes, he scored a record deal with Delicious Vinyl and released a hit single, Shake It Like a White Girl, in 1991. While his music career didn’t define him for the long term, it became his first lesson in branding and persistence.

But music wasn’t his true calling. In 2001, Itzler co-founded Marquis Jet with a radical idea: make private jet travel accessible without owning the jet. It was an audacious plan in an industry where luxury meant exclusivity. Marquis Jet sold fractional jet cards, letting people buy hours of flight time on private jets—no ownership required. His vision paid off, turning the company into a multi-billion-dollar business that was eventually sold to Berkshire Hathaway’s NetJets in 2010. Jesse’s knack for thinking outside the box helped him navigate and disrupt industries others wouldn’t touch.

The SEAL Who Transformed His Life
Itzler didn’t just build businesses; he built mental toughness. One of the more legendary stories of his life involves Navy SEAL David Goggins, a man known for pushing human endurance to its limits. In 2010, Jesse invited Goggins to live with him for 31 days to shock his life into a new gear of discipline and growth.

The experiment turned into a life-changing experience and later became the best-selling book, Living With a SEAL: 31 Days Training with the Toughest Man on the Planet. Goggins didn’t just introduce Itzler to extreme workouts, he taught him how to embrace discomfort, break mental barriers, and push beyond what most would consider impossible. Jesse adopted Goggins' ethos of “getting comfortable with being uncomfortable”—a principle that has influenced everything he’s done since.

Fail Fast, Fail Often—And Keep Going
But Jesse’s life wasn’t all smooth skies and success. He’s candid about the failures and missteps along the way. There were plenty of business ideas that fizzled out before they could take off, from failed tech ventures to concepts that never gained traction. One of his well-known misses was Alphabet City Sports Records, a company that created theme songs for professional sports teams. While some of their work, like the New York Knicks anthem, gained local popularity, it didn’t reach the national level of success Itzler had hoped for.

Through it all, Jesse’s resilience stood out. He doesn't view failure as defeat—he views it as feedback. He’s constantly learning, iterating, and pushing forward.

All Day Running Co. – Building a Culture of Movement
More recently, Jesse has embraced his love for endurance sports by co-founding All Day Running Co. in 2022. The company isn’t just about selling running gear or organizing races—it’s about cultivating a lifestyle centered on pushing limits and embracing discomfort. The brand's mission is to encourage people to run not just for fitness but to build mental fortitude and community. They host events like the “Run For It Challenge,” which has brought together thousands of people from all over the world to tackle personal running goals. It’s less about winning and more about showing up, day after day, with that same relentless drive Jesse himself embodies.

29029 – Climbing Everest, No Passport Required
Jesse’s latest venture, 29029, is the ultimate endurance challenge for those looking to test their limits in an entirely different way. Named after the height of Mount Everest, 29029 challenges participants to climb the equivalent vertical height of Everest—29,029 feet—but on a single mountain, within 36 hours.

The event, co-founded by Itzler, takes place on ski resorts in places like Utah, Vermont, and Idaho, where participants hike up the mountain repeatedly until they reach that symbolic Everest height. The beauty of 29029 is that it’s not a race against others—it’s a race against yourself, testing your endurance and willpower. It’s a reflection of Jesse’s ethos: life is about taking on hard challenges and seeing how far you can go.

Husband, Father, and Still Dreaming Big
Beyond his wild ventures, Jesse’s personal life is equally impressive. He’s married to Sara Blakely, the billionaire founder of Spanx, and together they have four children. Their family life is a testament to balancing ambition with meaningful connection. While Jesse’s entrepreneurial fire burns bright, he’s also a devoted dad, teaching his kids the same lessons of resilience and grit that have guided him.

So, what’s next for Jesse Itzler? One thing’s for sure: he’ll never stop dreaming up new challenges, building communities, and helping people embrace discomfort as a way of life. Whether he’s building companies, running ultra-marathons, or inspiring others to reach their potential, Jesse is living proof that creativity, persistence, and a willingness to do what others won’t are the keys to success.

Key Takeaways from Jesse Itzler’s Journey

  • Creative Roots: Start where you are and don’t be afraid to pivot. Jesse went from rapper to serial entrepreneur by staying open to opportunities.

  • Resilience: Fail fast, learn faster. Jesse’s path wasn’t without its stumbles, but each one brought him closer to his next big win.

  • Endurance for Life: From living with Navy SEAL David Goggins to starting endurance companies like All Day Running Co. and 29029, Itzler shows us that the real race is with yourself.

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