It's NEVER The Right Time To Start A Business, You Just Need To Do THIS! Feat. Jesse Itzler
Here are the top 10 key takeaways from Ed Mylett's conversation with serial entrepreneur Jesse Itzler about building businesses, optimizing life, and making the most of our limited time on earth.
1. Inexperience can be your greatest advantage
Jesse Itzler emphasizes that having no prior experience in an industry can actually be a blessing rather than a curse. When you don't know the established playbook, you're forced to innovate and think differently. This lack of preconceived notions allows entrepreneurs to approach problems with fresh perspectives and create solutions that industry veterans might never consider.
The common thread throughout Itzler's entrepreneurial journey was his complete lack of experience in every venture he pursued. Whether it was the rap game, private aviation, coconut water, or the NBA, he knew nothing about these industries when he started. This forced him to "rip up the playbook" and operate differently from established competitors, often leading to breakthrough innovations and unique market positioning.
2. Start before you're ready and figure it out along the way
The biggest mistake aspiring entrepreneurs make is waiting for the "right time" or until they feel completely prepared. Itzler argues that if you wait for perfect conditions, adequate experience, or complete preparation, you'll never start. The world moves too fast, and opportunities will pass you by while you're still planning.
Success comes from taking action despite uncertainty and trusting that you'll figure things out once you're in the door. Itzler consistently stepped into spaces where he was ill-prepared, knowing that he could learn and adapt quickly. This willingness to embrace uncertainty and discomfort becomes a competitive advantage because most people are too afraid to make these leaps.
The key is getting your foot in the door first, then developing competence through real-world experience. This approach allows you to move faster than competitors who spend months or years in preparation mode before taking any meaningful action.
3. People buy into people, not presentations
When Itzler pitched NetJets to create Marquis Jet, he didn't have a traditional business plan or PowerPoint presentation. Instead, he and his partner became the business plan themselves. They looked the executives in the eye and conveyed their passion, conviction, and unwavering commitment to making the venture succeed.
This personal approach proved more powerful than any document could have been. The NetJets executives were betting on Itzler and his partner as individuals, not on a set of projections or market analysis. Their genuine enthusiasm and promise to work 21-hour days to ensure success created trust and confidence that no formal presentation could match.
The lesson extends beyond entrepreneurship to any situation where you need buy-in from others. Authentic passion and personal commitment resonate far more deeply than polished presentations or technical expertise alone.
4. Create extraordinary customer experiences to drive referrals
The difference between successful businesses and mediocre ones often lies in the customer experience they provide. Itzler didn't just provide jet transportation; he created a complete service experience that went far beyond expectations. He would carry customers' bags, provide travel guides for destinations, and even bring flotation devices for their children.
This approach of "shock and awe" service turned customers into evangelists who enthusiastically referred others. Each satisfied customer became a source of multiple new clients because the experience was so memorable and exceptional. This viral growth through referrals eliminated the need for expensive marketing campaigns.
The principle applies to any business or profession. Whether you're a personal trainer, dry cleaner, or consultant, creating an experience that exceeds expectations transforms customers into advocates. Itzler suggests asking yourself: "Would I recommend myself?" If the answer is no, you need to identify and fix what's missing.
5. Time awareness creates urgency and focus
Both speakers share an intense awareness of mortality that drives their decision-making and prioritization. Itzler calculates that at age 50, he has only 27 summers left if he lives to the average age of 78. This mathematical reality creates urgency around making meaningful choices with his remaining time.
This perspective shifts how you evaluate opportunities and relationships. When Itzler visits his elderly parents, he realizes he doesn't have "five more years" with them—he has perhaps ten more visits. This scarcity makes each interaction precious and eliminates tolerance for wasted time or superficial activities.
The awareness extends to physical capabilities as well. Itzler notes that when climbing Mount Washington, there were no 70-year-olds at the summit. The window for certain experiences and adventures is limited, making it crucial to pursue meaningful goals while you're still capable rather than postponing them indefinitely.
6. Create systematic approaches to life optimization
Rather than leaving important areas of life to chance, Itzler has developed a three-bucket system for intentional living. His "electives" are annual goals and experiences he wants to pursue. His "sunshines" are daily habits that bring energy and fulfillment. The "ocean" represents all the mundane tasks that drain time from meaningful activities.
He schedules his year's major experiences and goals in advance, ensuring that important priorities don't get crowded out by urgent but less meaningful demands. He introduces one new positive habit each month, recognizing that twelve new winning habits in a year creates transformational change.
The system requires treating yourself like a CEO with an assistant—planning the next day's activities each evening rather than winging it. This level of intentionality ensures that time gets allocated to what matters most rather than being consumed by whatever feels urgent in the moment.
7. Proximity to excellence accelerates growth
Itzler's success accelerated dramatically when he gained access to high-performing individuals through Marquis Jet. Flying 4,000 successful entrepreneurs, CEOs, athletes, and entertainers gave him unprecedented access to their thinking patterns, daily routines, and life strategies. He treated every interaction as a learning opportunity.
He would systematically ask about their morning routines, eating habits, time management, and approaches to challenges. He then experimented with incorporating their successful practices into his own life, keeping what worked and discarding what didn't. This process of modeling excellence allowed him to rapidly develop his own high-performance system.
The principle extends beyond having money to access elite circles. In today's digital age, social media and podcasts provide virtual mentorship opportunities that previous generations never had. The key is being intentional about consuming content from people whose results you want to replicate, then actively implementing their strategies.
8. Success requires excellence across all life areas
True success isn't about maximizing performance in one area while neglecting others. Itzler emphasizes that being mega-wealthy but failing as a father, spouse, or community member isn't real success—that's just being wealthy. Authentic success means performing well in all the important "buckets" of life simultaneously.
This holistic approach requires intentional effort across multiple domains: family relationships, physical health, financial success, community contribution, and personal growth. When you excel in multiple areas, you create positive momentum that reinforces success across all domains.
The approach also provides resilience during difficult periods. When struggling in one area, you can still find fulfillment and build confidence through success in other areas. This prevents the downward spiral that occurs when people define themselves entirely through a single metric like income or career achievement.
9. Use future regret as a decision-making tool
Itzler employs a powerful two-word decision-making framework: "remember tomorrow." When facing difficult choices, he projects forward and considers how each option will make him feel the following day. This simple mental exercise consistently guides him toward decisions that align with his values and long-term goals.
The technique proved crucial during his monastery experience when he desperately wanted to quit after three days. By asking how leaving would make him feel tomorrow, he realized the regret would be worse than the temporary discomfort. This kept him committed to completing the full 15-day experience.
The framework works because it forces you to move beyond immediate emotions and impulses to consider longer-term consequences. Whether deciding to exercise, make difficult phone calls, or persist through challenges, this forward-looking perspective typically reveals the right choice.
10. Wanting it badly enough is the ultimate differentiator
The most important factor in achieving significant change or success is genuine desire rather than talent, connections, or resources. Itzler argues that most people think they want things, but they don't truly want them enough to persist through inevitable obstacles and setbacks.
When his sister successfully created a celebrity coffee table book despite having no publishing experience, she succeeded because she genuinely wanted it. When publishers rejected her, she kept calling. When celebrities' publicists hung up, she called back. Her authentic desire sustained her through all the rejections and learning curve.
This level of want cannot be manufactured or faked. It comes from deep alignment between your goals and your values. When you truly want something, you naturally find ways to overcome obstacles, learn necessary skills, and persist through temporary failures. Without this authentic desire, even the best strategies and resources won't create lasting success.