November: Living with a SEAL: 31 Days Training with the Toughest Man on the Planet

by Jesse Itzler

Book Description

“Entrepreneur Jesse Itzler will try almost anything. His life is about being bold and risky. So when Jesse felt himself drifting on autopilot, he hired a rather unconventional trainer to live with him for a month-an accomplished Navy SEAL widely considered to be “the toughest man on the planet”!
LIVING WITH A SEAL is like a buddy movie if it starred the Fresh Prince of Bel- Air…and Rambo. Jesse is about as easy-going as you can get. SEAL is…not. Jesse and SEAL’s escapades soon produce a great friendship, and Jesse gains much more than muscle. At turns hilarious and inspiring, LIVING WITH A SEAL ultimately shows you the benefits of stepping out of your comfort zone.”

Book Club Review

Thanks for being a part of the Modern Leadership Monthly Book Club. If you happened upon this page and are not a member you can join for free here .

The book club is designed to explore books that will help us on our leadership journey. It is a part of the Modern Leadership Podcast where we breakdown a book weekly in each episode. You can catch the podcast here.

This month’s book is Living with a SEAL: 31 Days Training with the Toughest Man on the Planet by Jesse Itzler

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Brief Summary

Hitting a plateau or finding yourself in a rut can be challenging. With work, family, social and recreation demands pulling us in different directions we can find ourselves burned out. When you feel overwhelm coming on and you fight the desire to put it on autopilot, how do you get yourself out of the rut? For Jesse Itzler, former MTV VJ, rapper, successful jet rental leader and husband to the youngest female self-made billionaire, Sara Blakely, found himself floating to autopilot, he went extreme. Intentionally creating an experience that would test his commitment, his drive, his resiliency and his sanity, he hired a Navy Seal to live with him for 31 days and put him through the most grueling, physically and mentally demanding “workout” of his life.

About the author – Jesse Itzler

Jesse Itzler only eats fruit until noon, loves Run-D.M.C., and enjoys living life “out of the box,” actually, he doesn’t even have a box. He cofounded Marquis Jet, the world’s largest prepaid private jet card company in 2001, which he and his partner sold to Berkshire Hathaway/NetJets. He then helped pioneer the coconut water craze with Zico coconut water, which he and his partners sold to The Coca-Cola Company in 2013. He is a former rapper on MTV and he produced both the NBA’s Emmy Award-winning “I Love This Game” music campaign and the popular New York Knicks anthem “Go NY Go.” When he is not running ultra marathons or being a dad to his three kids, Jesse can be found at the NBA’s Atlanta Hawks games, where he is an owner of the team. He is married to Spanx founder Sara Blakely and the couple and their 3 boys live in Atlanta, Georgia.

You should read this book if:

  • You are ready to disrupt your thinking
  • You want inspiration that is unconventional
  • A rare look into business operations of a successful leader
  • A few good laughs and “oh my” moments

Who shouldn’t read this book

  • You just want the facts- no fluff. This book is entertaining and inspirational, not your typical business book
  • Language: I admit to struggling with the language. Let’s just say you shouldn’t listen in the car with the kids
  • You can’t take a little off-color humor.

What surprised me

I guess I didn’t know what to expect. I have heard Jesse on podcast episodes and had a gist of the book, the adventure and the experience. He sounded tough to me, the experience sounded “hard”. And then I read the book. “Hard” doesn’t even begin to describe the experience that Jesse writes about. Crazy might be more relatable. But he impressed me. Jesse is in a position financially where he can have and do most anything he wants. He can take his foot off the gas and he can enjoy the fruits of his efforts. HE DOESN’T.

Jesse is an executive with drive, passion and commitment. He is authentic. This book inspires.


I hated the language of this book. Some of you may not agree, but I felt it wasn’t needed and really took away from the message. I am referring to many four-letter words throughout and mostly I felt it distracted, it didn’t add to the book.


  • [R]esearch shows that stepping out of our routine in life is great for the body and spirit… the brain too.
  • His no rhyme or reason approach to our workout schedule actually brought a lot of clarity into my life.
  • Most of my successes in life have come from learning how to be comfortable with being uncomfortable.
  • Every day do something that makes you uncomfortable. —SEAL
  • This is a habit I have. When I see or read about someone interesting, I call them up and basically ask them to be my friend.
  • The part of me that would grow up to hire a Navy SEAL, that came from Mom.
  • don’t think about yesterday. I think about today and getting better. —SEAL
  • It doesn’t have to be fun. It has to be effective. —SEAL
  • I eat only fruit until noon. That’s been my thing since I read Fit for Life by Harvey Diamond in 1992. For over twenty-five years, just fruit till noon.
  • Any success I have ever had in my life usually occurred when I was not chasing the money but was doing things out of passion.
  • “Failure is just life’s way of nudging you and letting you know you’re off course.”
  • I just like to go to sleep hungry… so I wake up hungry. Life is all about staying out of your comfort zone.”
  • SEAL built his career around honor. At a minimum I have to honor my commitment to him.
  • “Never let them boo you,”
  • If you’re hungry, run faster. You’ll be home quicker. —SEAL
  • Know what’s important to you and protect it at all costs. —SEAL
  • The simplicity that SEAL has is one of the most important things in life. He gets to do what he loves every day. He lives stress-free.

My Key Key Key Takeaway

  • My key: “Never let them boo you”

As I read this book, I asked myself what my level of commitment to success is. I wondered often during my reading if I could do it. Would I do it? Probably not, it isn’t my journey. But Jesse’s discussion of embarrassment and going after what you believe in with passion and confidence stands out as my key learned lesson. You might not always succeed. But never let them boo you.

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Podcaster | Speaker | Leadership Mentor

Jake Carlson is a popular speaker, accountability partner, and host of the Modern Leadership podcast. Jake built his business while traveling with his family around the world. Follow him on Facebook, Twitter, Instagram or LinkedIn. Read more about him here.