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# Lessons from Jesse Itzler
- URL: https://www.antoinebuteau.com/lessons-from-jesse-itzler/
- Published: 2025-12-26T23:47:18.000Z
- Updated: 2026-07-18T22:08:54.000Z
- Description: Jesse Itzler—entrepreneur, former rapper, Marquis Jet co-founder, and ultramarathoner—approaches life with an “all-in” philosophy, connecting mental toughness, time management, unconventional business tactics, and the 40% Rule in a demanding study of personal commitment.
- Author: Antoine Buteau
- Tags: Profile, Personal Development, Sports & Athletics Profiles

Jesse Itzler—entrepreneur, former rapper, co-founder of Marquis Jet, and ultramarathoner—is known for his "all-in" philosophy on life. His teachings focus on mental toughness, time management, and unconventional business tactics.

![Visual summary of operating lessons from Jesse Itzler.](https://www.antoinebuteau.com/content/images/2026/07/image-74-optimized.webp)

---

### **On Mindset and the "40% Rule"**

1. **"When your brain says you’re done, you’re only at 40%."** – The core philosophy taught to him by David Goggins.
2. **"If it doesn't suck, we don't do it."** – On the importance of seeking discomfort.
3. **"The mind is the strongest muscle in the body."**
4. **"I don’t negotiate with myself. If I say I’m going to do something, I do it."**
5. **"You have to be willing to be misunderstood if you want to be successful."**
6. **"Get comfortable being uncomfortable."**
7. **"Pressure is a privilege."** (A mantra Jesse often repeats regarding high-stakes business).
8. **"Everything you want is on the other side of fear."**
9. **"The only way to get better is to do things that make you sweat."**
10. **"Your brain is always trying to protect you. It wants you to stop. You have to tell it to keep going."**

### **On Time Management and "18 Summers"**

1. **"You only have 18 summers with your kids. Make them count."** – His famous philosophy on intentional parenting.
2. **"Don't wait for a life-changing event to change your life."**
3. **"We spend so much time planning our businesses, but so little time planning our lives."**
4. **"The goal isn’t to live forever, the goal is to create something that does."**
5. **"I want to have a resume of experiences, not just things."**
6. **"Time is the only thing you can't get back. Guard it fiercely."**
7. **"We overestimate what we can do in a day, but underestimate what we can do in a decade."**
8. **"My 'Big Ass Calendar' is how I ensure I actually live my life."**
9. **"I live my life in 'laps.' Every year is a new lap, and I want to run it faster than the last."**
10. **"Routine is the enemy of time. It makes life go by faster. Break the routine."**

### **On Business and Success**

1. **"I didn’t have the best resume, but I had the most hustle."**
2. **"If you want to get someone’s attention, do something that doesn’t scale."**
3. **"You don’t get what you want, you get what you negotiate."**
4. **"Business is about relationships, not transactions."**
5. **"Complacency is the kiss of death."**
6. **"I’m not a fan of the ‘what if.’ I’m a fan of the ‘what is.’"**
7. **"Don’t be afraid to ask. The worst they can say is no."**
8. **"I focus on the journey, not the exit strategy."**
9. **"If you aren't waking up excited, you're in the wrong business."**
10. **"Every 'no' gets you closer to a 'yes.'"**

### **On Resilience and Growth**

1. **"You can’t improve what you don’t measure."**
2. **"Self-doubt is the biggest killer of dreams."**
3. **"You have to be your own biggest fan."**
4. **"The silver lining is always there; you just have to look for it."**
5. **"Stop overthinking and start doing."**
6. **"Success is not a destination, it’s a way of life."**
7. **"Life is short. Do the things that make you feel alive."**
8. **"Don't let your past define your future."**
9. **"Be the person you want to meet."**
10. **"Your environment dictates your output. Surround yourself with winners."**

### **Core Life Learnings**

1. **"The Power of the 'Bold Move':"** Sending a pizza to a CEO’s office or waiting in a lobby for hours—Jesse teaches that one bold move can bypass years of traditional climbing.
2. **"Fit on the Fly:"** You don't need a 2-hour gym block. You can get fit in 10-minute bursts throughout the day.
3. **"The Brownie Story:"** Don't focus on the obstacles (the calories); focus on the goal (the taste).
4. **"Living with a Monk:"** Peace doesn't come from a lack of activity; it comes from a lack of mental clutter.
5. **"The Kevin Garnett Lesson:"** Always be the most intense person in the room.
6. **"Experience Over Gifts:"** Give people memories, not sweaters.
7. **"The 10x Rule of Networking:"** Give 10 times more value than you ask for.
8. **"Keep your overhead low and your dreams high."**
9. **"Wellness isn't a hobby; it's a prerequisite for success."**
10. **"You are the CEO of your own life. Fire the bad habits and hire the good ones."**

### **The "Life on Offense" Planning System**

1. **"The Misogi Rule:"** Do one big, year-defining challenge every year. It should be so hard that it has a 50% chance of failure. This becomes the "anchor" of your year.
2. **"Kevin’s Rule:"** Plan one "mini-adventure" every 8 weeks. That’s only 6 days a year, but it ensures you never go more than two months without something to look forward to.
3. **"Winning Habits (1-a-Quarter):"** Don't do New Year's resolutions. Instead, commit to one new habit every 90 days. By the end of the year, you have four permanent life changes.
4. **"The Big-Ass Calendar Philosophy:"** "If it’s not on the calendar, it’s not a priority; it’s just a wish." Jesse uses a physical 3-foot wall calendar to see the entire year at once.
5. **"Play Life on Offense:"** "Most people play life on defense—reacting to emails, meetings, and other people's requests. Put your big goals on the calendar first, then let the world fit in around them."
6. **"The Blender Test:"** To review your life, imagine putting your health, work, and relationships in a blender. Rate the result from 1-10\. If it’s a 6, identify the 2-3 specific things dragging it down and fix them first.\[[1](https://www.google.com/url?sa=E&q=https%3A%2F%2Fvertexaisearch.cloud.google.com%2Fgrounding-api-redirect%2FAUZIYQHRgbNy9NS530Gsmaa9TIThMRQ0RUulCE5EIN9BsCRZblq%5FsnFByAjUFMK2jD4Lt9inJlfIlr59TxSW3eSqzzRs1JkL0GnG8D899W0uq1t-6vvdvd%5FxvCzn15JqmDOyRQsj-jU%5F1fE%3D&ref=antoinebuteau.com)\]

### **On Productivity and "Time Richness"**

1. **"Daily Vitamins:"** Jesse spends 2–3 hours every day on "loves"—activities that energize him (running, reading, music). He calls this "taking his daily vitamins" so he doesn't burn out.
2. **"The 20-Hour Rule for Learning:"** "I don’t learn from books; I learn from immersion. Spend 20 hours with an expert, and you’ll learn more than reading 20 books on the subject."
3. **"Single-Tasking is a Superpower:"** "Multitasking is a lie. The monks taught me that if you're washing a cup, wash the cup. Be 100% where your feet are."
4. **"Net Zero Inbox:"** Every December, Jesse clears his inbox to zero. "Don't carry last year's baggage into next year's opportunities."\[[2](https://www.google.com/url?sa=E&q=https%3A%2F%2Fvertexaisearch.cloud.google.com%2Fgrounding-api-redirect%2FAUZIYQFZRk3LgMkeXco98ykgxXLIFn9SOB0MOE5Q9RxF8WkvKK0t9LmbTZx-QBhU0BSYKr3AcPBsH-P09R5mLtIeotjXtcasxF1Bll4up0W05GGbhb7yPSGEVpr-Wr30rY-sdPC6-7GYx8M%3D&ref=antoinebuteau.com)\]\[[3](https://www.google.com/url?sa=E&q=https%3A%2F%2Fvertexaisearch.cloud.google.com%2Fgrounding-api-redirect%2FAUZIYQE1rTTCcnzYyNLSRGSpQYW5epzLt8MuMCeUOU-4cY%5FslUGxZim2X5jUPYzsZ3dbzhmK0JZyey0IcUU3fhsn%5FTeeFvUcX6TqlIxqyCLAg%5FHd1KY2aqvILCFkId6ElHP4MxmvVtXWydILQ3Urc1dAvOMhXcFs1nx3LfTstjAU81LsW7ZFvlLeaNa5wWCvaJvyMRGHjqrOTGcpwwOADaHnbpf9zxJcNdCFhrDS6UHWTPm7Y2Q0RZUGbDQ%3D&ref=antoinebuteau.com)\]
5. **"Routine is a Rut:"** "Routines are efficient, but they make time disappear. Newness and adventure are the only things that slow down the clock."
6. **"If you don't have a seat at the table, make one."** (His advice on how he got into the private jet business without experience).

### **On Wealth and Perspective**

1. **"The Billionaire's Trade:"** Jesse tells a story of a billionaire who said, "I would trade every penny I have to be your age again." Jesse's takeaway: **"Youth is the only currency that matters. Don’t spend it all trying to get the other kind."**
2. **"Friend Reduction:"** "Curate your inner circle for energy, not drama. If someone consistently drains your battery, they shouldn't have a key to your time."
3. **"The Underdog Mentality:"** "I still fly commercial and stay in basic hotels sometimes. I never want to get so comfortable that I lose my edge."
4. **"Money doesn't buy happiness, but it buys options. Use those options to build memories, not just buy things."**
5. **"You find your true purpose at the intersection of: What you love, what you're good at, and what helps people."**

### **Impactful One-Liners for 2025**

1. **"Don't f\*cking waste 2025."** (His viral 2024 year-end mantra).
2. **"If you don't challenge yourself, you don't know yourself."**
3. **"Patience is the key to success, but urgency is the key to life."**
4. **"I don't stop when I'm tired; I stop when I'm done."**
5. **"The best gift you can give yourself is getting over the fear of embarrassment."**
6. **"We all have a 'reserve tank'—the 40% rule applies to your patience and your kindness, too."**
7. **"Be 'Adventure Ready'—keep your health in a place where if a friend calls for a spontaneous hike or trip, you don't have to say no because of your fitness."**
8. **"Your calendar is your scorecard.\[**[**4**](https://www.google.com/url?sa=E&q=https%3A%2F%2Fvertexaisearch.cloud.google.com%2Fgrounding-api-redirect%2FAUZIYQFM3myffCsVKPl%5FdHvNRANqLZTbV0vmEyfCsFl%5FEcI2fnZQqoHvwH-TYRHxydm8U5fufu78WTBTxDZiAlxHMMOv0CqOKhDJXU7hBXQ4VTqYdYu0QCXjOeK7di-Fb%5FuFoK0Fk6BBOlM9vQ7Po2hTL%5Fd-Rv7yaCcdlu6J7vksR3F2qNrHyex6WSRk1jw5VbhG24dQX5nWbSJtAspGx2mYSTx-g-4%3D&ref=antoinebuteau.com)**\] At the end of the year, it tells the story of who you actually were, not who you wanted to be."**

---

### **Primary Sources and Links**

To hear Jesse explain these concepts in detail, these are the primary sources:

1. **Book: Living with a SEAL**
  - Core Theme: The 40% rule and mental toughness.
  - [Amazon Link](https://www.google.com/url?sa=E&q=https%3A%2F%2Fwww.amazon.com%2FLiving-SEAL-Days-Training-Toughest%2Fdp%2F1455534684&ref=antoinebuteau.com)
2. **Book: Living with the Monks**
  - Core Theme: Stillness, perspective, and time management.
  - [Amazon Link](https://www.google.com/url?sa=E&q=https%3A%2F%2Fwww.amazon.com%2FLiving-Monks-What-Learned-Staying%2Fdp%2F1478923382&ref=antoinebuteau.com)
3. **The Build Your Life Challenge / Jesse Itzler’s Official Site**
  - Core Theme: The "Big Ass Calendar" and the "18 Summers" philosophy.
  - [JesseItzler.com](https://www.google.com/url?sa=E&q=https%3A%2F%2Fjesseitzler.com%2F&ref=antoinebuteau.com)
4. **Impact Theory Interview with Tom Bilyeu**
  - Core Theme: Resilience and "Misery creates memories."
  - [Watch on YouTube](https://www.google.com/url?sa=E&q=https%3A%2F%2Fwww.youtube.com%2Fwatch%3Fv%3Df9N7XGid%5F68&ref=antoinebuteau.com)
5. **The Ed Mylett Show**
  - Core Theme: Business hustle and the "18 Summers" rule.
  - [Watch on YouTube](https://www.google.com/url?sa=E&q=https%3A%2F%2Fwww.youtube.com%2Fwatch%3Fv%3DXhYpUvD00lA&ref=antoinebuteau.com)
6. **Jesse’s Instagram (@jesseitzler)**
  - Core Theme: Daily motivation and "Fit on the Fly" tips.
  - [Instagram Profile](https://www.google.com/url?sa=E&q=https%3A%2F%2Fwww.instagram.com%2Fjesseitzler%2F&ref=antoinebuteau.com)
7. **Joe De Sena’s Spartan Up Podcast**
  - Core Theme: Pushing physical limits and the origins of Marquis Jet.
  - [Spartan Podcast Link](https://www.google.com/url?sa=E&q=https%3A%2F%2Fwww.spartan.com%2Fblogs%2Fpodcast%2Fjesse-itzler&ref=antoinebuteau.com)
8. **The Big-Ass Calendar (Official Site):** Where he sells the physical planning tools and hosts the "Big Ass Calendar Club."
  - [BigAssCalendar.com](https://www.google.com/url?sa=E&q=https%3A%2F%2Fjesseitzler.com%2Fproducts%2Fthe-big-ass-calendar-2025&ref=antoinebuteau.com)
9. **"My First Million" Podcast (Dec 2024 Interview):** A deep dive into his 2025 planning system.\[[1](https://www.google.com/url?sa=E&q=https%3A%2F%2Fvertexaisearch.cloud.google.com%2Fgrounding-api-redirect%2FAUZIYQHRgbNy9NS530Gsmaa9TIThMRQ0RUulCE5EIN9BsCRZblq%5FsnFByAjUFMK2jD4Lt9inJlfIlr59TxSW3eSqzzRs1JkL0GnG8D899W0uq1t-6vvdvd%5FxvCzn15JqmDOyRQsj-jU%5F1fE%3D&ref=antoinebuteau.com)\]
  - [Watch on YouTube](https://www.google.com/url?sa=E&q=https%3A%2F%2Fwww.youtube.com%2Fwatch%3Fv%3Dff1z3GUcfO8&ref=antoinebuteau.com)\[[5](https://www.google.com/url?sa=E&q=https%3A%2F%2Fvertexaisearch.cloud.google.com%2Fgrounding-api-redirect%2FAUZIYQHplPSk3nNq41eSL-YHTrFUykCbHA5vZ-ObMODHoqQGhwrBwXUJLVszMO%5FjW3Sdt9UKcxi-xnIFPLzV0tc4SZvChNTRrxbNoC5SbP4yrUKTma6EvJyQMaHLClzWuZD6bJSubYYw8tC1-7xvqgf9-7HmB6Pk-XANNcsTs75DbitgkEo1AheZYT-mKTlwVFA%3D&ref=antoinebuteau.com)\]
10. **The BYLR (Build Your Life Resume) Course:** A digital program where he teaches these specific systems.
  - [BYLR.com](https://www.google.com/url?sa=E&q=https%3A%2F%2Fbylr.com%2F&ref=antoinebuteau.com)
11. **"The Midlife Male" Podcast:** Jesse discusses "Friend Reduction" and staying motivated after age 45.
  - [Listen here](https://www.google.com/url?sa=E&q=https%3A%2F%2Fmidlifemale.com%2Fpodcast%2Fjesse-itzler-planning-2025%2F&ref=antoinebuteau.com)
12. **29029 Everest:** The endurance event company Jesse co-founded based on the "Misogi" principle.
  - [29029everest.com](https://www.google.com/url?sa=E&q=https%3A%2F%2F29029everest.com%2F&ref=antoinebuteau.com)
13. **We Do Hard Things:** Jesse’s community platform for monthly challenges.
  - [wedohardthings.com](https://www.google.com/url?sa=E&q=https%3A%2F%2Fwedohardthings.com%2F&ref=antoinebuteau.com)