Oct 15, 2024 · 1h 21m · bigdeal
How Millionaire Entrepreneur Jesse Itzler Balances Business, Family, and Adventure
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In this wide-ranging interview on The Big Deal Podcast, entrepreneur and endurance athlete Jesse Itzler joins host Codie Sanchez to discuss shattering mental limitations, building multi-million-dollar ventures, maintaining an eighteen-year marriage with Sara Blakely, and intentionally designing a life rich in memorable adventures.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Codie holds 27.7% of the talking time here. How this is scored →
Codie as informed peer 4.0 Guest teaching 3.6 Guest disagreement 0.5 Codie pushing back 0.4
speaking balance: gold is Codie, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 42:36 Jesse challenges pessimistic wealth statistics
Jesse directly pushes back against the premise that becoming wealthy is mathematically improbable by doing rough population math on millionaire ratios.
Hardest push from Codie ▶ 42:08 Codie challenges simplistic grit definitionsCodie pushes back against romanticized views of entrepreneurship by noting that the math of eight-figure scaling is punishingly rare.
Biggest teaching moment ▶ 25:17 Jesse outlines fractional jet card mechanicsJesse educates Codie on how Marquee Jet operated without purchasing planes by slicing NetJets inventory into marked-up 25-hour cards.
Codie holds their own ▶ 33:59 Codie articulates venture fund legal obligationsCodie draws upon her experience running an institutional cannabis fund to explain the legal constraints and moral hazards of refunding investor capital.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Codie as informed peer | Guest teaching | Guest disagreement | Codie pushing back | Why |
|---|---|---|---|---|---|---|
| Breaking Limitations and Realizing What Is Possible | 1 | 0 | 0 | 0 | Codie introduces the podcast, previews Jesse Itzler's background and achievements, and delivers a mid-intro sponsor read for Riverside. | |
| Overcoming the Fear of Public Embarrassment | 3 | 3 | 1 | 0 | Codie asks Jesse about overcoming the fear of public embarrassment, prompting him to share his teenage breakdancing hustle in Washington, D.C. | |
| Navigating Public Failures and Humiliating Situations | 4 | 4 | 0 | 0 | Jesse describes public failures in rap and sports music before detailing his Big-Ass Calendar system and annual Misogi concept. | |
| Running Man Festival and Defining True Fulfillment | 3 | 4 | 0 | 0 | Jesse explains how his Running Man festival operates and recounts stories illustrating how fulfillment stems from connections rather than status. | |
| Maintaining an Underdog Mindset and Financial Perspective | 4 | 4 | 1 | 1 | Codie and Jesse discuss retaining an underdog mindset and how wealth shifts your relationship with money and time without changing fundamental problems. | |
| The Beverly Hills Hotel Salads and Observing Mentors | 3 | 5 | 0 | 0 | Jesse shares how he used to observe high-profile executives at the Beverly Hills Hotel and study wealthy clients' habits at Marquee Jet. | |
| Pioneering the Private Jet Card with Marquee Jet | 5 | 5 | 0 | 1 | Codie asks about margins and business models in private aviation, and Jesse details how Marquee Jet structured 25-hour jet cards with NetJets. | |
| BizScout Marketplace for Small Business Acquisitions | 3 | 4 | 0 | 0 | Following an ad read for BizScout, Jesse recounts the wild story of 50 Cent interning for him before becoming an international superstar. | |
| The Sheets Strips Failure and Investor Responsibility | 7 | 3 | 1 | 1 | Jesse details the failure of Sheets energy strips, and Codie shares her own institutional investor experience managing a cannabis venture fund. | |
| Product Quality, Virality, and Evolving Life Priorities | 3 | 4 | 1 | 1 | Jesse discusses product-market fit, viral marketing loops, and explains why he no longer wants to spend his remaining decades launching startups. | |
| Entrepreneurial Realities and Breaking Wealth Stereotypes | 6 | 4 | 3 | 2 | Codie cites national statistics on small business success, while Jesse playfully counters by calculating millionaire ratios to argue wealth is attainable. | |
| Coaching, Mentorship, and Empowering Others to Win | 4 | 5 | 0 | 0 | Jesse lists former interns and partners who achieved major commercial exits, attributing success to extreme coaching, observation, and self-belief. | |
| Fostering Resilience and Positive Self-Talk in Children | 4 | 3 | 0 | 0 | Jesse shares how he and Sara Blakely emphasize intentional self-talk and persistence when helping their kids work through challenging homework. | |
| Marriage Dynamics and Conflict Resolution with Sara Blakely | 4 | 3 | 1 | 0 | Jesse humorously breaks down the differing emotional needs between him and Sara Blakely, including a recent argument over a steam room door. | |
| Codie Sanchez Announces Main Street Millionaire Book | 5 | 3 | 0 | 1 | Codie plugs her upcoming book and shares therapy experiences, while Jesse discusses using targeted coaches to resolve specific couple issues like nutrition. | |
| Grief, Mutual Support, and Leading Family by Example | 4 | 3 | 0 | 0 | Jesse reflects on family grief, mutual support in marriage, and teaching resilience by setting personal daily examples in front of children. | |
| Turning Entrepreneurial Wish Lists into Immediate Reality | 4 | 3 | 1 | 0 | Jesse explains how his earliest entrepreneurial milestones evolved from modest wish lists into actionable immediate lifestyle choices. | |
| Rapid-Fire Wisdom on Marriage, Assets, and Keynotes | 5 | 4 | 1 | 0 | In a rapid-fire round, Jesse discusses purchasing a farm, martial arts, and key principles for delivering engaging, story-driven keynote speeches. | |
| The Grandfather's Safe and Building a Life of Stories | 4 | 5 | 0 | 0 | Jesse concludes with the story of finding his grandfather's secret autobiography in a hidden safe, underscoring the importance of building a legacy of stories. |
Statements from this episode (18)
Itzler: Entrepreneurs must deliberately put themselves in embarrassing situations
“I think if you want to be an entrepreneur, part of being an entrepreneur is you have to get over the fear of being embarrassed. You know, it's like the best gift you can give yourself in anything, entrepreneur or not. Once you get over the fear of being embarr…”
Itzler: Running Man wellness festival featured a 5,000-square-foot sauna
“We had a thousand people there. It's a three-day like wellness festival in the middle of Georgia. And it's kind of like the Woodstock of wellness. There's speakers and breakout sessions and music, and bands, and we built the world's biggest sauna. It's almost …”
Itzler: Warren Buffett says private jets are the one luxury people never give up
“I remember Warren Buffett saying that's like the one thing you'll never get rid of is, is private jet.”
Itzler: Marquis Jet flew 3,000 cultural and business leaders
“When we had Marquee Jet, which is my first successful, second successful company, but the biggest. We flew 3000 of the who's who of pop culture, entertainers, CEOs, whatever. I was 2829 years old when we started the company”
Itzler: Most people earn 5x to 10x more in their 40s and 50s
“In your twenties and thirties, for most people, you're gonna make five to 10 times more money in your forties and fifties than you will in your twenties and thirties, because you'll have more contacts, you'll be better at whatever it is you do, you'll be much …”
Itzler: Zico Coconut Water sold to Coca-Cola for nearly $100M
“We were thinking like maybe close to a hundred million when we sold it.”
Itzler: Marquis Jet generated approximately $5B in aggregate sales
“Marquee was, I mean, Marquee, we did like five billion in sales.”
Itzler: Marquis Jet launched with only $4M from friends and family
“Like, I think we raised four million dollars from friends and family, which to start a jet company, I mean, it doesn't make any sense.”
Itzler: Marquis Jet customers spent an average of $250,000 annually
“I remember sitting with my partner, like, our average sale was, we were, people were spending about 250,000 dollars a year. They didn't have to, but like, on average, a year with us on jet time.”
Itzler: 50 Cent interned with him for a year and a half
“So Curtis came in, and he worked with me for like a year and a half, and then he became 50 cent.”
Itzler: 50 Cent mandated Marquis Jet exclusivity in all his contracts
“And then the next day he wrote into all of his contracts he would only fly with Marquee Jet.”
Sanchez: Cannabis venture fund achieved a 3x return from 2016 to 2019
“From like, 2016 to 20, or 2016 to 2019 we killed it we just made so much money we like three x'd the fund gave it all the investors back their money”
Itzler: I have started 20 companies that failed over my career
“I've also had 20 companies that didn't work.”
Sanchez: Only 0.4% of US business owners reach eight-figure revenue
“Only three percent of Americans own a business, that of the three percent that own a business, only 10% will ever hit a million dollars, that of the, those that hit ten million, that's .4%. So .4% of the three percent ever get to eight figures.”
Itzler: Dwayne Johnson's Teremana Tequila is valued north of $1 billion
“He created and partnered with The Rock on The Rock's tequila. It's worth over, north of a billion dollars.”
Itzler: Helix Sleep sold for hundreds of millions of dollars
“Adam Tishman, who is my intern, created Helix, this mattresses. Sold for hundreds of millions of dollars.”
Sanchez: Refusing to date across political parties is a major mistake
“Yeah, you know, I read a study the other day that increasingly young people, specifically women, which is interesting, but young people today don't want to marry or date somebody of the opposite political party, which I think is such a mistake because my paren…”
Itzler: Keynote speakers must tell proprietary stories only they can tell
“The most important thing is to tell stories in a speech that only you can tell. So if I say, You know, hey, you have to get comfortable being uncomfortable. A million people can say that. But if I say, you know, I rode my bike across the United States of Ameri…”