How Millionaire Entrepreneur Jesse Itzler Balances Business, Family, and Adventure
Codie SanchezKey Moments
Jesse Itzler on balancing adventure, family, and business with a focus on living a life of purpose and unforgettable experiences.
Key Insights
Embrace discomfort and the fear of embarrassment to achieve personal and professional growth.
Prioritize scheduling personal adventures and experiences, not just work tasks.
Focus on building a life rich in stories and experiences, not just financial wealth.
Develop winning habits and routines to foster personal growth and fulfillment.
Authenticity and creating unique value are crucial for standing out in any venture.
Invest in yourself through learning, coaching, and experiences to continuously improve.
EMBRACING DISCOMFORT AND THE FEAR OF EMBARRASSMENT
Jesse Itzler emphasizes that overcoming the fear of embarrassment is a key to liberation, not just in business but in life. He shares personal anecdotes, like breakdancing in public at 15 or performing at the Super Bowl and forgetting lyrics, to illustrate how putting oneself in uncomfortable situations, even with the risk of failure, leads to growth and reward. This mindset encourages individuals to step outside their comfort zones, understanding that facing potential embarrassment is a necessary step towards achieving exceptional outcomes and personal development.
THE POWER OF INTENTIONAL LIVING AND ADVENTURE SCHEDULING
Itzler advocates for proactively scheduling personal life and adventures, similar to how one schedules business meetings. He uses a 'big ass calendar' to visualize 365 days, blocking off time for family trips, date nights, and personal challenges. This visual planning ensures that life doesn't become solely about work. By prioritizing experiences, individuals create a life filled with memorable moments and a sense of accomplishment, ensuring they look back with satisfaction on a life truly lived.
LIVING A LIFE DEFINED BY YEAR-DEFINING AND MINI ADVENTURES
A core philosophy for Itzler is the concept of 'misogi,' interpreted as undertaking one significant, year-defining event annually. These events, whether biking across America or participating in a challenging race, provide tangible achievements to reflect upon. Supplementing these are smaller, 'mini-adventures' taken every other month, which add variety and joy to life. This structured approach to adventure ensures a life rich in experiences, creating a compelling narrative of personal achievement and exploration.
THE FOUNDATION OF WINNING HABITS AND SELF-IMPROVEMENT
Itzler highlights the importance of cultivating winning habits, routines, and mindsets. He suggests adding new positive habits quarterly, such as meditation or increased water intake, as simple yet impactful ways to enhance well-being. Investing in oneself through continuous learning, seeking coaching (like memory or swim coaches), and even living in a monastery for spiritual growth are key. This commitment to self-improvement fuels personal development and ensures individuals are always striving to be better versions of themselves.
AUTHENTICITY AND CREATING VALUE IN BUSINESS AND LIFE
Itzler stresses that even the most brilliant marketing cannot salvage a mediocre product. Success stems from authenticity and delivering genuine value, whether in business or personal pursuits. He also notes that in today's crowded markets, standing out requires creating something entirely new or significantly improving an existing offering. This focus on inherent quality and unique contributions ensures that ventures and personal efforts resonate and endure.
THE VALUE OF STORIES AND EXPERIENCES OVER MATERIAL WEALTH
Ultimately, Itzler believes that a legacy is built not on material possessions but on the stories collected and shared. He shares an anecdote about finding a hidden safe with his grandfather's autobiography, emphasizing the enduring value of family history and personal narratives. He encourages people to invest their time and resources in experiences that create these stories, whether through family trips, adventures with friends, or pursuing personal passions. The greatest wealth, he implies, is a life well-lived and richly recounted.
NAVIGATING BUSINESS FAILURES AND THE RESPONSIBILITY OF CAPITAL
Itzler openly discusses business failures, like his 'Sheets' dissolvable energy strip venture, which taught him that product quality trumps celebrity endorsements. He emphasizes the significant emotional toll of losing other people's money, seeing it as a greater burden than losing one's own. This perspective underscores the profound responsibility that comes with managing investments and the ethical considerations involved in business dealings, even when pursuing ambitious ventures.
MENTORSHIP THROUGH OBSERVATION AND PROXIMITY
Early in his career, Itzler learned by observing successful individuals in environments like the Beverly Hills Hotel. He intentionally placed himself in proximity to influential people, learning business acumen and social skills through keen observation and initiating conversations. This approach highlights the power of learning by example and networking, demonstrating that valuable insights can be gained even without formal training, by actively engaging with and studying those who have achieved success.
THE EVOLUTION OF GOALS AND THE PURPOSE OF WEALTH
Itzler's business goals have evolved from tangible achievements like owning a swimming pool or growing fruit to more abstract desires for a life filled with adventure and meaningful experiences. He argues that wealth should enable these pursuits, allowing individuals to create memorable moments with loved ones. He encourages people to be crystal clear about what they truly want to do with their resources, emphasizing that many desired experiences are achievable with focused effort and intention, rather than waiting for improbable windfalls.
FOUNDATIONS OF SUCCESSFUL RELATIONSHIPS AND PARTNERSHIPS
In both business and marriage, Itzler values alignment on core values and mutual support. He differentiates between transactional communication and genuine connection, stressing the importance of listening and understanding a partner's needs. His own marriage thrives on acknowledging individual pursuits while building shared experiences around core beliefs. He advises couples to address potential conflicts proactively, reinforcing that a successful relationship requires continuous effort, compromise, and a shared vision.
RAISING CHILDREN WITH CONFIDENCE AND RESILIENCE
Itzler and his wife focus on praising effort over results to foster healthy development in their children. They encourage resilience by allowing children to experience disappointment and reframe challenges, emphasizing the power of positive self-talk. This approach aims to cultivate children who believe in their capabilities and are equipped to navigate life's obstacles with a confident mindset, understanding that words and attitudes play a crucial role in shaping their future achievements.
THE LONG-TERM VALUE OF EXPERIENCES AND RELATIONSHIPS
Reflecting on his life, Itzler emphasizes that tangible assets diminish over time, but the stories and connections created endure. He shares an anecdote of finding a secret safe left by his grandfather, underscoring the lasting impact of shared experiences and personal legacies. His commitment to investing in experiences, from family adventures to group trips, such as a sauna tour of Finland, illustrates his philosophy that a life rich in memories and relationships is the ultimate form of wealth.
Mentioned in This Episode
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●People Referenced
Creating an Adventurous and Fulfilling Life
Practical takeaways from this episode
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Common Questions
Jesse Itzler believes in creating a life so good that one looks back on it with the feeling of having lived it with adventure every year. This involves prioritizing personal experiences and adventures on your calendar, undertaking year-defining activities (Misogi), and incorporating mini-adventures consistently.
Mentioned in this video
Founder of Spanx and Sneaks, wife of Jesse Itzler. Mentioned for her business acumen and influence on Jesse's perspective.
Jesse Itzler's former intern who created Helix mattresses, sold for hundreds of millions.
A hip-hop magazine Jesse Itzler was featured on the cover of, which led to embarrassment due to the article's content.
Whiskey brand co-founded by Kenny Austin and Conor McGregor, sold for hundreds of millions.
Jesse Itzler wrote a song for them which they won the Super Bowl with, and he performed at the Super Bowl but forgot the lyrics.
Mentored by Jesse Itzler as an intern, later became the rapper 50 Cent. His contracts later specified flying only with Marquee Jet.
An adventure Itzler scheduled on his calendar, similar to his wife's husband's challenge.
A business buying marketplace designed to simplify the process of finding and acquiring businesses.
An oral dissolvable energy strip infused with caffeine that Jesse Itzler launched, which ultimately failed due to taste and lack of repeat customers.
A tequila brand co-founded by Kenny Austin, a former intern of Jesse Itzler.
An old Japanese ritual interpreted by Itzler as doing one big, year-defining activity each year.
A place Jesse Itzler used as his 'office' to observe and interact with successful people when he was starting out.
The former name of Jesse Itzler's company (likely referring to Zico or an earlier venture) used in a note to 50 Cent.
Tequila brand co-founded by Kenny Austin and The Rock, worth over a billion dollars.
A personal rule named after a friend who remembered a death anniversary and reached out, highlighting the importance of thoughtful connection.
Coconut water company founded by Jesse Itzler, sold for hundreds of millions.
Record label Jesse Itzler signed with after college.
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