My First Million Wiki

Jesse Itzler

6 min read

Jesse Itzler

Most people who sell a company for $16 million at 27 would optimize for the next exit. Jesse Itzler optimized for the number of times he could say “I can’t believe that actually happened.”

Itzler is a serial entrepreneur who sold a jingles business to SFX, co-founded Marquee Jets and sold it to Berkshire Hathaway, invested in Zico Coconut Water before Coca-Cola acquired it, and became a part-owner of the Atlanta Hawks. But what makes him unusual among the wealthy founder class is his framework for converting money into memory.

The Misogi

Every year, Itzler commits to one defining adventure. He borrowed the concept from an old Japanese purification ritual. In 2015, his misogi was inviting David Goggins—a Navy SEAL he’d seen running a 100-mile ultramarathon—to live in his house for 30 days and train him. That experience became the bestselling book Living with a SEAL.

The math is simple. Start at 35, do one misogi per year until 85, and you have 50 extraordinary experiences baked into your life. Most people have three or four stories worth telling at their funeral. Itzler is engineering fifty. watch the full breakdown

Another year, he wanted to climb Mount Everest but couldn’t commit the time. So he climbed a hill near his house fourteen times in a row to match Everest’s elevation gain. It’s the kind of creative constraint-breaking that reveals how arbitrary most of our limitations are.

Kevin’s Rule

The misogi handles the annual epic. But what about the months in between?

Itzler’s solution: every other month, do something you normally wouldn’t do. Camp in the snow. Attend a random conference. Take your kids fishing on a Tuesday. These aren’t bucket-list items—they’re pattern interrupts.

The compound math is striking. Six mini-adventures per year, sustained over 50 years, equals 300 experiences that wouldn’t have happened otherwise. And the time cost is roughly 2% of your year.

Shaan Puri adapted this into what he calls “20 unscripted days”:

“I love my routine, I love my normal day, but any extreme strength carries with it an extreme weakness. I can just live a routine life and all my days blend together… So creating these 20 unscripted days where I’m going to throw away the routine and plan out 20 unscripted days this year.” — Shaan, Talking to Tim Ferriss

The Three C’s

Itzler maintains his network through a three-minute daily practice. Each day, he sends one message that falls into one of three categories: a compliment, a congratulations, or a consolation.

Three minutes per day, 365 days per year, equals roughly 1,000 touchpoints annually. He calls these “permission slips”—moments that give him standing to reach out later when he needs something or wants to reconnect.

Most networking advice focuses on events and introductions. Itzler’s approach is slower but compounds indefinitely. After ten years, he has 10,000 deposits in his relationship bank.

Will vs. Can

Early in his career, Itzler asked a mentor named Lou Katz for $10,000 to start his jingles business. Katz asked a question that reframed everything:

“Will you make this business work without the 10 grand? … I didn’t ask you can you. I said will you. There’s a big difference between can and will.” — Lou Katz, as recounted by Jesse on MFM

The distinction matters. “Can” is about capability. “Will” is about commitment. Most founders have the capability to succeed. Far fewer have the commitment to persist through the part where it stops being fun.

The First Customer Trap

Itzler’s first jingle deal was with the New York Knicks. He got paid 4,800 to produce. On paper, a terrible business model.

But that Knicks logo opened every other door:

“For most people, they’d be like, ‘That’s a terrible business model.’ It was the best business model in the world for me because once I had the Knicks, those phone calls to get into the other sports teams became very easy.” — Jesse on MFM

He lost $800 on the deal and gained a career. The first customer is often the product, not the revenue.

Finding White Space

When Itzler co-founded Marquee Jets, the private aviation market had two options: buy a plane (expensive, complicated) or charter flights (unreliable, inconsistent). Itzler found the gap.

“We found the ‘white space.’ People who only want to fly 25 hours a year and don’t want the responsibility of ownership. That was the idea: a 25-hour jet card that works like a debit card.” — Jesse on MFM

He and his partner pitched NetJets founder Rich Santulli directly. First-year sales: $200 million. Eventually, Berkshire Hathaway acquired the company.

The pattern: look for customers stuck between two existing solutions. They’re often underserved and overlooked.

The Big Rocks

Shaan frequently references Itzler’s time management philosophy using the jar analogy:

“You have a jar… you have sand, small rocks and big rocks… If you put the sand in the jar first and then you say, ‘Great. Now I’m going to fit the big rocks in,’ they don’t go in at all. But if you put the big rocks in first… turns out you can fit all the things into the container if you do it in the right order.” — Shaan on MFM

Schedule the misogi first. Then the mini-adventures. Then the three C’s. Routine fills whatever space remains. Reverse the order and routine fills everything.

Friend Reduction

At a certain level of success, Itzler has stopped chasing high-aggravation opportunities:

“I’m at a point where if it’s ‘high aggravation for high reward,’ I’m not doing it. I’m on ‘friend reduction’ right now. I don’t want high-aggravation friends. I want to maximize incredible experiences and relationships.” — Jesse on MFM

This is the luxury of compounding: eventually, you can afford to optimize for low-friction joy rather than maximum return.

MFM Appearances

  • Jesse Itzler’s Exact Playbook For Creating HIT AFTER HIT (#504) — Primary episode covering his frameworks and business history
  • The 2023 Milly Awards (#531) — Shaan names Jesse as his “Billy of the Year”

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