What I learned about Living Life from Jesse Itlzer – author, rapper, entrepreneur

Not that Jesse Itzler has it all figured out. He just seems like he’s figured out more than the rest of us. He’s figured out how to live. The post below is a collection of nuggets I’ve picked up from multiple interviews and Jesse’s breakout book “Living with a SEAL” in which Jesse tells the story of living with high-endurance athlete and all-around badass David Goggins.

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The three most memorable nuggets are:

  1. Send hand-written letters.
  2. Take the path with the best story.
  3. Use math to decide how to spend time.

Send hand-written letters

At one point in his life, Jesse Itzler was spending 1 hour per day hand-writing letters of gratitude. Those letters shifted his mindset and led to profitable business relationships.

This is why it works. Writing letters by hand is out of fashion. And, most people don’t bother to express gratitude.

Writing the letter feels good, and receiving the letter feels good. Since almost no one takes the time to hand-write letters, by doing so you immediately stand out from the crowd. Since you took time to compose a sincere message, you express genuine care for the person you write to.

Take the path with the best story

Jesse has lived more than most of us. From launching businesses, to crazy 100 mile endurance runs, to living with monks. He seems to use a story-tellers mental model for deciding how to live.

The mental model is a guide on how to live a more exciting life.  When given an opportunity, consider the story as part of the reward.  Usually, the worst thing that can happen is nothing.  You may miserably fail, but you will have a story to tell.  If instead you choose to stay home on the couch, you won’t even have the story. So get moving!

Use math to decide how to spend time

Itzler talks about how, as he turns 50, he re-evaluates how he spends his time, using math. I’m certain a 25 year old who takes this advice to heart will live a vastly different life.  He uses math to re-frame decisions in the bigger picture.  For example, if you spend 2 hours a day watching TV, that’s 700 hours a year, or 7,000 hours over the next 10 years. What would you rather do with those 7,000 hours?

The other way Jesse uses math is to better appreciate relationships.  The average american life span is 78 years.  If your parents are already 65, they may only have 13 years of life remaining.  If you only visit them twice a year, you have only 26 visits left.  Make the most of every single visit.

Books by Jesse Itzler

Living with the Monks: What Turning Off My Phone Taught Me about Happiness, Gratitude, and Focus

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

I’ve read Living with a SEAL, and highly enjoyed it. It is a very entertaining and inspiring read.


This post is written in honor of the great master, Banri Hoshi.

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