Never Fear Failure: Jesse Itzler on Living With A SEAL, Tackling Life Plateaus & Getting Comfortable With Being Uncomfortable

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“The only way to really get better is to experience pain, to get uncomfortable, go to places that you don’t want to go, and improve.”

Jesse Itzler


Jesse Itzler fast-talked his way right out of college into a recording contract, ultimately taking his music all the way to MTV, the Billboard 100 and even an Emmy.

Jesse Itzler then took an entrepreneurial left-turn, creating and selling big companies — companies like Marquis Jet, the world’s largest prepaid private jet card company, and Zico Coconut Water — before wooing Spanx founder Sarah Blakely (worth over $1 billion) all the way to the altar.

Jesse Itzler eats only fruit before noon. And when he’s not raising three kids, he runs 100 mile races, raises millions for charity and can be found court side supporting the Atlanta Hawks — the NBA team he recently purchased with some friends.

What I’m trying to say is that Jesse Itzler is a quite the character. An amazing life highlighted by one predominant theme:

never be afraid to fail.

But there is one thing that scares Jesse Itzler: stagnation.

Despite all his success, in 2010 Jesse felt his life had settled into a too-comfortable routine. So he did what any rational human would do: he invited a Navy SEAL to move in with him.

But this was no ordinary SEAL (as if any such thing exists). This was David Goggins — perhaps the most intense, taciturn individual walking planet Earth. A one man metaphor for adversity destruction, Goggins’ example and words formed the original inspiration behind my own journey:

When you think you are done, you’ve only accomplished about 40% of what you are truly capable of.

Goggins military record is astonishing. As a Navy SEAL, he was one of an elite group of men regularly sent on some of the toughest missions in the world. He is the only member in the U.S. Armed Forces to complete SEAL training, Army Ranger School (where he graduated as Honor Man), and Air Force tactical air controller training. Not only has he faced combat in Iraq, he served as the body guard for Iraqi Prime Minister Ibrahim al-Jaafari.

To honor his brother soldiers felled by battle and to raise money for charity, David lost 100 pounds in 60 days and went on to tackle the 10 most rigorous ultra-endurance challenges on the planet, compelling his 260-pound frame to top finishes at races like Badwater– a 135 mile jaunt across Death Valley in 130 degree heat (finishing 5th as a novice) — and Ultraman– 1 320-mile 3 day triathlon circumnavigation of the Big Island of Hawaii he completed with his tennis shoes duct taped to the pedals of an ill-fitting loaner bike to a 2nd place finish overall. He even completed 203.5 miles in the 48-Hour National Championship endurance foot race, earning a spot among the top 20 ultra-marathoners of the world.

Just another training day for Goggins, topped off with a recent Guinness World record for most pull ups in a single day: 4,025.

Goggins accepted Jesse’s invitation with just one rule: for 31-days, Jesse had to do every thing David asked him to do. No exceptions.

What happened next would change Jesse’s life forever. An adventure chronicled in his new book, Living With A Seal: 31 Days Training With The Toughest Man On The Planet. I found the book super fun and highly entertaining. So when my travels took me to Atlanta, I jumped at the chance to meet up with him.

This is a fun conversation about about Jesse’s dynamic, extraordinary life. His success equation. Why growth is crucial to happiness. Why we must always be willing to get uncomfortable. Why it’s important to never settle, never stagnate, and most of all, why we must never, ever be afraid to fail.

Specific topics include:

  • living outside your comfort zone
  • the benefits of consistent discipline
  • the Goggins 40% Rule
  • evaluating self-challenge
  • the biggest life lessons living with a Navy SEAL
  • putting yourself first pie chart
  • fearlessness and confidence in business
  • the importance of giving back
  • running as meditation
  • Atlanta Hawks ownership and community focus
  • balancing work and family
  • why Jesse eats only fruit before noon
  • the value of authentic relationships for advancement
  • the Goggins accountability mirror

Question: Are you living on a plateau? What are you willing to do to continually grow?

I’d love to hear all about it in the comments section below.

I sincerely hope you enjoy the exchange.

Peace + Plants,

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SHOW NOTES

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Background, Context & Reference:

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Production & sound design this week by me (Tyler is still sick!). Additional production by Chris Swan. Graphic art by Shawn Patterson.

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