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Gary Brecka hosts Jesse Itzler, entrepreneur and author of Living with the Seal, alongside Devin Levesque, founder of Sweet Honey Farms and ProMix Nutrition. Jesse has exited $5 billion in companies including Marquee Jet and is part-owner of the Atlanta Hawks. Devin is a 33-year-old wellness entrepreneur focused on regenerative farming and clean nutrition products.
The conversation explores Jesse's life design philosophy, including the Japanese concept of Masogi (one big yearly adventure) and intentional time management. Jesse's upcoming book Die Young as Late as Possible embodies his approach to maintaining youthful energy throughout life. The discussion covers their friendship forged through extreme adventures like 29029 mountain challenges, cycling across America, and visiting the world's best saunas.
Key topics include the spiritual billionaire mindset, building meaningful relationships through shared experiences, and practical systems for designing an adventurous life. The conversation takes place in Gary's biohacking-optimized home, with hydrogen water enhancing the energy and flow of discussion throughout the session.
The Masogi System: Designing Life Through Adventure
The Masogi, an old Japanese ritual, requires doing one big year-defining thing annually - "if you don't have one thing to show for your year, your work-life balance is so out of whack" - Jesse
Combined with Kevin's rule of six mini-adventures every other month, this creates 400+ experiences over a lifetime starting at age 30, versus just routine work years
"You start to stack adventures - that's freaking amazing. Without that, I don't want to look back and be the 80% version of myself" - Jesse
Living with David Goggins: Seven Years of Lessons
Goggins lived with Jesse's family for seven years as security, not just the 30 days described in Living with the Seal, after Jesse met him at a 24-hour race in 2006
"He was 280 pounds, had no aid team, just crackers and water, was peeing blood at mile 70 and duct-taped his feet - I wanted whatever secret sauce he had" - Jesse
The biggest takeaway was simplicity: "I love the simplicity of how he lived his life. There's so much ego in business - the earlier you can simplify and figure out what you love to do with people you love, that's a great journey" - Jesse
The Muffin Strategy: From Zero Experience to $5 Billion
Jesse started Marquee Jet with no aviation experience by buying all the muffins in Monterey to meet wealthy TED attendees who couldn't get their usual coffee shop order
His first customer, Josh Koppelman who had just sold half.com to eBay, bought a jet card after Jesse offered him a muffin - "those 200 muffins turned into a $5 billion company"
"When you have no experience, your secret weapon is caring the most. I cared so much about this guy's experience that he gave me a referral, then the next guy gave me a referral" - Jesse
The Big Ass Calendar and Intentional Time Design
The big ass calendar shows all 365 days on one piece of paper, allowing you to "track towards goals, see gaps in time, and get a visual of where you're spending and not spending time" - Jesse
Gary implemented this system, scheduling family time, holidays, and adventures first: "This is the first time we've ever done this - I've been so much more intentional about my time with my kids"
"People aren't lacking time, they're lacking a system. If you can get a system, then it starts to really click" - Jesse
The Spiritual Billionaire Philosophy
"If you have a billion dollars but your spirit is zero, a billion times zero equals zero. But if you have one dollar and your spirit is a billion, one times a billion" - Jesse
Spiritual wealth includes enthusiasm, caring, integrity, and kindness - "those aren't skills you learn in college, those are attitudes. Attitudes are free, those are decisions" - Jesse
"You bond so much more with people through experiences than sitting at a cubicle. One adventure and you can learn more - I only knew one of 10 guys ten years ago, now it's a whole new friend group" - Jesse
Devin's Five-Bucket Life Design at 33
Devin's five non-negotiable values: family, health, community, freedom of time, and giving back - "if a person, place, or thing isn't adding value to your life" in these areas, he won't do it
"I took a red marker and green marker to my calendar - everything that didn't hit those values got a red X, and half my day was gone" - Devin
"Every single person 80, 90, 100 years old has the same common denominator - regretting what they did with their time, not maximizing it" - Devin
Die Young as Late as Possible
Jesse's upcoming book title Die Young as Late as Possible encapsulates his philosophy: "I want to stay young as long as possible, squeeze as much out of life as I can"
The ultimate human means "being as good as you can be in the buckets that matter most to you - not the best in the world, but as good as you can be" - Jesse
For Devin, it's daily improvement: "I'm comparing myself to who I was yesterday - did I work out harder, call my mom, have integrity, do the right thing?"
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