Jesse Itzler

“I don’t remember anything from college,” Jesse Itzler said.

Then he went back.

“I remember, specifically, one lesson,” he said. “I actually call it the $160,000 lesson. But I don’t…”

“What was the lesson?” I had to interrupt. See, he was going to fly right by that. But I stopped him. And you can thank me later.

I can’t explain Jesse Itzler as just one thing. He’s not just an “author” or “entrepreneur.”

He’s an energetic fireball. And contagiously motivating. Because he’s always finding new ways to win the race against normalcy, regret, getting trapped by failure or getting stuck in a day-in and day-out rut. He knows how to escape all these things. And he told me how on my podcast.

We were talking about his new book, “Living with the Monks: What Turning Off My Phone Taught Me About Happiness, Gratitude, and Focus.”

Jesse moved to a monastery to live with monks. He wanted to fully immerse himself in a new way of life. When he got back everyone asked him, “What’d you miss the most?” But no one asked him, “What didn’t you miss?”

Jesse was looking for the unknown. He wanted to get out of his usual pattern, strip himself of everything he relies on (family, home life, technology) and rediscover his instincts.

Life was becoming a distraction.

“I felt like I was losing my superpower, which is my intuition.” he said.

“How did you sense you were losing it?” I asked.

“Little things in the past would lead me in the right direction. And that voice wasn’t talking to me anymore.”

Jesse needed to get his superpower back. He was committed. So he moved into a monastery.

Five days in, he was ready to quit.

“I was resisting,” he said.

And you can see this in the book. He shows you the “before” and “after” of his mind. In the “before” scenes, Jesse focuses on annoyances. But in his observations after, he’s focussed on his interactions with people, which showed he really shifted.

I didn’t ask if he got that voice back. Because we had so many conversations going on at once. Jesse is full of stories. So I’ll get back to the $160,000 lesson. But I also really recommend you check out his other stories in the podcast. I think you’ll find them just as valuable.

THE $160,000 LESSON:

“I was taking an advertising class my senior year. And I was at a crossroads in my life. I was either going to go into the music business, which I loved, or I was going to sell a product called Aunt Frannie’s Brownies.”

Every month, his roommate’s Aunt Frannie sent brownies. “I don’t know what she put in these brownies, but…”

“Pot?”

It wasn’t pot.

But Jesse fell in love with the idea of selling these. He could see the success. So he tested the idea (smart business move) in class for his final exam. He said, “If the professor likes this campaign, then I’m going to roll it out and go into the brownie business.”

He told me about the project. Every student had to create a fake brand from scratch: slogan, advertising campaign, packaging, jingle, etc.

All the students wrote papers. But five would have to pitch their idea in front of the whole class.

“Nobody prepared for the oral presentation. You didn’t want to get picked. You just wanted to hand it in and go enjoy the summer,” he said.

“What were the odds?”

“There was a 5% chance I’d get picked.”

He got picked. The teacher passed around a hat. Told everyone to put their name in it.

“Sitting to my right in the classroom was this guy—let’s call him Ronnie. And Ronnie was a professional jackass. Ronnie bullied half of this class for four years of college. So I took 20 pieces of paper and wrote ‘Ronnie, Ronnie, Ronnie.’ I overloaded the hat with Ronnie’s name.”

Ronnie did the same thing…

But with Jesse’s name.

So Jesse went first.

He goes up in front of the class and starts pitching Aunt Frannie’s Brownies.

“Thirty seconds in, the professor says, ‘Stop.’ He goes, ‘Son, I want to know, what is your point of differentiation?’”

Jesse said, “I’m a brownie, I’m moist, I’m delicious, I can be gluten-free if you want me to be gluten-free. I’m home-baked.”

The professor stopped him again.

“’No. Son, there are a thousand brownies that come out every day.”

“This is the lesson,” Jesse said. “Substitute brownie for restauranter, author, manufacturer, lawyer, whatever you’re going to do—there are a thousand of them coming out every day. If you want to be great and make it in this world, you better be a much different brownie than everybody else.”

Jesse thinks about this all the time. “How am I different?”

He lives this.

You can see it in his books, his businesses.

• He founded a jet company, Marqui Jet, and sold it to NetJet. And profited.
• He became one of two white rappers in the early ‘90s by making an appointment at a big music mogul’s office. Except, he didn’t make the appointment as Jesse Itzler. He pretended to be someone else. Someone who the music industry would never say “no” to. Jesse showed up to the appointment and played his own music for the producer while they “waited” for this other rapper.
• He got a music deal.
• Then, later on in his rap career, Jesse invented a new genre of music: sports music (it’s what you hear in the stadiums).
• Jesse got into coconut water. The category didn’t exist. They had to create it.

The list goes on.

Jesse is always first.

It’s part of his edge. But, I think that’s just a small part. The real lessons from Jesse are about action. You can tell from the way he thinks.

Jesse asks questions like, “If no one taught you how to do your job, what would you do?”

And says things like, “I don’t look at anything in my life as achievements. I look at them as experiences.”

And does things like… live with monks.

It’s all part of his “life resume.”

And I think that’s what this podcast is really about. Finding the moments in life that you can always tap into.

“We put so much emphasis on our work resume, which is important, but if we turn the model upside down, and we focus on our life resume…”

He kept going. But I think I’ll let you fill in the idea.

Show Notes:

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

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

My first interview with Jesse Itzler: Ep.163: 6 Simple Steps to Becoming Self-Made

Vanilla Ice (rapper)

Marquis Jet(a company Jessie founded, which was then sold to NetJets)

Zicococonut water (Jesse’s a partner)

My interview with Shane Snow, author of Smartcuts [Ep. 355 – Make The Breakthrough You Need (With These “Smart Cuts”]

President Obama

Dwight Eisenhower

John F Kennedy

Lyndon B Johnson

Richard Nixon

Spanx(invented by Sara Blakely who Jesse is married to and who I got to interview on this podcast: Episode 211: How To Get a Billion Dollar Idea)

Philip Roth who wrote “American Pastoral” a Pulitzer Prize winning book

Steve Jobs

Game of Thrones

Monasticism 

Silent retreat

Thich Nhat Hahn and his monastery  which is Buddhist

Jesse stayed with Orthodox Christian monks

Vipassana (silent retreat)

“Fit for Life” by Harvey Diamond and Marilyn Diamond

Jesse turned some of the highlights from his book into an animated series. Check it out here