Key Takeaways
- Jesse started as a rapper, pivoted to jingles & songs for sports teams
- Produced jingle for NY Knicks, gave him credibility to grow business
- Sold jingle company for $4M, lost most money due to lack of financial literacy
- Got idea for Marquis Jets after chartering private jet, saw demand
- Convinced NetJets to partner by bringing in potential customers
- Strong customer service and word-of-mouth fueled growth
- Now cares more about experiences & relationships than maximizing money
- Does annual goal-setting focused on adventures and connections
- Gets fulfillment from helping people
- Advises focusing on health/family over grinding business in 20s-40s
- Relationships and self-worth should be priorities over chasing achievements
Intro
Jesse Itzler is a billionaire founder and serial entrepreneur best known for his success in building Marquis Jets and ZICO coconut water. He’s also married to his equally successful wife Sarah Blakely, founder of shapewear brand Spanx.
(4:30) The Beginning of His Entrepreneurial Journey
Jesse talks about how he got started in business by pivoting from his original goal of becoming a rapper. After getting dropped from his record label, he began writing jingles and songs for sports teams.
He shares the story of producing a jingle for the NY Knicks and how even though it cost him more to produce than they paid, it gave him credibility. He realized that people buy into momentum and stories as much as the actual product. Getting the NY Knicks opened doors to work with other teams and turned into a business.
(8:59 - 9:36) His First Big Hit
Jesse sold his jingle/sports song company for $4 million upfront, with additional earnouts over time. After taxes and paying his partner, he cleared about $1.5 million. Having no context for wealth, he didn’t know how to manage the money and ended up losing most of it through overspending.
He admits he had no financial literacy growing up and no one taught him how to handle money. This experience taught him an important lesson about being careful when coming into wealth suddenly.
(14:46 - 21:00) Creating Marquis Jets
The idea for Marquis Jets came to Jesse after chartering a private jet and realizing there was an opportunity around fractional jet ownership. He convinced NetJets to partner by bringing in a focus group of potential customers to prove demand.
Jesse emphasizes that his success was not due to sales talent but establishing credibility, getting momentum, and selling the vision. He highlights the importance of customer service by going above and beyond for the first few customers, leading to key referrals.
(50:37 - 52:11) Lifestyle and Finances
When asked about his finances, Jesse says he’s no longer focused on maximizing money but rather on experiences, relationships and feeling good. He talks about his annual goal-setting process, trying to do one big “year-defining thing” and mini-adventures regularly.
He gets fulfillment from helping people through speaking, coaching programs and races even though they aren’t huge moneymakers. He realizes that nothing will provide better ROI than the feeling he gets from inspiring and connecting with people.
(1:13:55 - 1:18:29) Relationships and Fulfillment
Jesse stresses that authentic relationships, experiences and self-worth should be priorities - not grinding solely for business success. He advises not sacrificing your health and personal life throughout your 20s-40s just to make more money later.
The same fulfillment from selling a business can come from smaller wins like finishing a race or helping someone. His advice is to maximize joy from ordinary moments and relationships, rather than only seeking extraordinary achievements.
