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

By November 29, 2015May 23rd, 20195 Comments

“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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Thanks to this week’s sponsors:

Thrive Market’s mission is to make healthy living easy and affordable for everyone. Thrive is giving Rich Roll Podcast listeners a special deal – one grand-prize winner will walk away with a 1-year membership and $1,000 to spend at Thrive Market. And that’s not all—10 other runners up will win a free 1-year membership too! Enter at

Note: Promotion only applicable for first time Thrive members A superior shave at an affordable price. Type in my coupon code “ROLL” at purchase for $5 off your starter set and get an entire month’s worth of shaving for just $10 when you visit


Connect With Jesse: Website | Facebook | Twitter

Background, Context & Reference:

Notable People Discussed in today’s podcast:

Related Podcasts You Might Enjoy:

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

*Disclosure:Books and products denoted with an asterisk are hyperlinked to an affiliate program. We are a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for us to earn fees by linking to and affiliated sites.

The Plantpower Way  is available at these fine retailers!

Amazon*  |  Barnes & Noble  |  IndieBound  |  Penguin

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  • Hilary Bumm says:

    Podcast fodder for your consideration-
    The Pease brothers live by a personal motto, Where There’s a Wheel, There’s a Way, which also happens to be the title of their new book*.
    Capturing hearts across the nation, Kyle, who has Cerebral Palsy, and his clean-eating brother Brent, who serves as Kyle’s assistance athlete, demonstrated their “can do” attitude during the recent 2015 New York City Marathon. Despite a disintegrated wheelchair tire, the team heroically crossed the finish line, after more than 7 hours, thanks to the kindness of fellow marathoners Amy, of Frederick, MD and Kamran Zokai of New York. This incredible, yet happenstance, team effort demonstrates the message that the Kyle Pease Foundation strives to spread; everyone can achieve their goals with that ‘anything is possible’ through heart, hard work, team work and determination.

  • Andrew Mead says:

    I loved this episode. I haven’t read the book yet, but it’s on the way.

    It gave me a little kick in the pants to remember the habits I’ve been working hard to build, but have let slide. I used to also only eat fruit before noon, but started to fade away from that. Now I’m back and feeling great.

    I don’t want to be Goggins, but I love some of the ideas he appears to stand for. Grit, perseverance, not feeling sorry for yourself.

    Thanks for putting the time is Jesse and Rich.

  • Camille says:

    I loved this podcast and have now read Jesse’s book twice in a week. It may be odd, but I find it to be one of the most inspirational books I have read to get me moving. I am quite active anyway, as I teach 13 classes of yoga each week at my studio in the little town I live in. I have completely fallen into a rut, and sadly furnished it as well. Time to change it up to things I don’t like. I am completely in love with SEAL. I have gone on to research him and watch interviews and videos. I love people like David Goggins, hard work and ethics, so thank you for introducing us by having Jesse on your show. I have now incorporated nickels and dimes into my life, the dimes are sit ups, not pull ups though! And even though I hate running I plan on adding a 1 mile run to my daily routine. Awesome podcast Rich, thank you!

  • Tommy F says:

    90% Vegan.. 10% Weasel??? (Sorry.. I’m being 100% judgmental.. my bad)

    David Goggins seems like he’d be a great RRP guest.


  • Mary-Ellen Landry says:

    Loved this podcast, Rich. I think it is all in what you need to hear in the moment. NYE, I felt depleted, unmotivated, and paralyzed towards taking on any of the tasks needed to continue to build our plant-powered health coaching business. This is a vital time in our new career that we are so passionate about and I listened intently to what Jesse had to say. It resonated fully. Energy soared and back on track to help others in this wonderful opportunity in a career of service and health. Namaste and love from Canada.

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