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How to Become a Spiritual Billionaire
Methods of Prosperity newsletter no. 113: Jesse Itzler
Sean Allen Fenn
August 14, 2025
Most of my successes in life have come from learning how to be comfortable with being uncomfortable.”
Most entrepreneurs focus on traditional metrics like ROI, market analysis, and business performance.
That’s not how Jesse Itzler calculated his downside protection.
You’ve heard of vibe coding. What about experience investing?
Consider his approach to investing in a bar called “Trust”. It was with Roger Clemens’ associates in the early 2000s.
Jesse Itzler invested around $100,000.
But reasoned: “If this place stays open for two years, I can easily eat and drink $100,000 worth of food and alcohol. So, my downside is covered.”
He did the math. $1,000 per week in food and drinks over two years would cover his investment.
Other investors analyze weekly revenue and business plans.
Itzler was more concerned with his personal consumption quota than traditional financial metrics.
Most people try and build their paper resume.
Not Jesse Itzler.
He’s building his life resume.
Typical entrepreneurs focus on financial accumulation.
Itzler emphasizes building a “life resume” filled with experiences and personal challenges.
Jesse Itzler is an American entrepreneur, author, and endurance athlete.
This philosophy led him to:
• Live with a Navy SEAL for 30 days to push his limits
• Complete ultramarathons and endurance challenges
• Take on unconventional business ventures for the learning experience
Many entrepreneurs want to earn a billion dollars in net worth.
Not Jesse Itzler.
He’s shooting for becoming a “spiritual billionaire”.
Itzler learned this concept from his father. He recognized the importance of being a spiritual billionaire. That is, prioritizing spiritual wealth.
Which included social, intellectual, physical, and purposeful well-being over pure financial accumulation.
This shaped his investment decisions to value experiences and connections. As well as personal growth alongside monetary returns.
The lesson?
Create value beyond financial returns.
Jesse Itzler’s investment philosophy is this:
“Sometimes, the value you get out of a venture isn't just about the financial return. It can be about the experiences, the connections, and the enjoyment you get along the way.”
Jesse Itzler is:
Co-founder of Marquis Jet. It’s one of the world’s largest private jet card companies. Which was later acquired by Berkshire Hathaway/NetJets.
Partner in ZICO Coconut Water, which Coca-Cola acquired.
Founder of The 100 Mile Group, a brand incubator and accelerator.
Part-owner of the Atlanta Hawks NBA team.
Early in his career, Jesse performed as the rapper “Jesse Jaymes”. He released the hit single, Shake It Like a White Girl. He wrote over 50 theme songs for major sports teams. including the New York Knicks’ anthem, Go New York Go, and the NBA’s award-winning theme, I Love This Game. He also managed legendary hip-hop group Run-DMC and won a Grammy as a producer in the 1990s.
Jesse is a #1 New York Times bestselling author. Books he wrote include, Living With a SEAL. Which details training with Navy SEAL David Goggins. Another book of his is Living With the Monks, about lessons learned in a monastery.
He’s a globally recognized keynote speaker. He delivers talks on business, mindset, endurance, and personal growth.
Jesse has completed over 50 marathons and multiple 100-mile races. Not to mention Ultraman events, and even biked across America.
He co-founded 29029 Everesting. Which is a challenging endurance event. It’s where participants climb a mountain. But not any mountain. They climb until reaching the elevation of Mount Everest!
His wife is Sara Blakely, the founder of SPANX, and they have four children. We love him for his unconventional approach to life. He blends bold entrepreneurship, athletic pursuits, and personal development.
Jesse Itzler’s estimated net worth is between $200 million and $250 million. In October 2021, Sara sold a majority stake in Spanx to Blackstone in a deal that valued the company at $1.2 billion.
I like you,
– Sean Allen Fenn
PS: Notice there’s only one action for you to take. The purpose of wealth is freedom. You can have financial freedom, but not by yourself. That’s why we’re building our core group of people. It’s a community to help each other achieve financial freedom. One way is by pooling our resources to invest in Multifamily real estate together. Whatever method of prosperity you choose, don’t go at it alone. You can now join our Methods of Prosperity community on Telegram here:
