Jesse Itzler: Building a Life of Adventure and Success

Jesse Itzler is an entrepreneur, author, and adventurer who has built multiple successful businesses and lives life with an infectious enthusiasm. In this wide-ranging conversation, Jesse shares his philosophy on creating memorable experiences, building thriving companies, and making the most of every day.

The Importance of Pushing Past Fear

Jesse believes that getting over the fear of embarrassment is one of the most liberating things you can do as an entrepreneur and in life generally. He recounts how at age 15, he convinced his sister to drive him and a friend from New York to Washington D.C. so they could breakdance on the street for money. Despite his nerves, they ended up drawing a crowd and making $80.

This early experience taught Jesse an important lesson: "If I could get over that fear and get rewarded, then whoa." He realized that pushing through the butterflies in your stomach can lead to amazing opportunities and experiences.

Of course, putting yourself out there doesn't always work out perfectly. Jesse admits he's been booed off stages and had plenty of embarrassing moments over the years. But he sees this as part of the process of living an exceptional life:

"If you want to have an exceptional life, you've got to put yourself in exceptional situations. And it doesn't always work out, you know, but you have to put yourself in those situations."

Scheduling Adventures and Defining Moments

One of Jesse's key strategies for living an extraordinary life is being intentional about scheduling adventures and memorable experiences. He uses a giant wall calendar to visually map out the year ahead, blocking off time for trips, events, and activities he wants to do.

Jesse follows three main rules for filling out his calendar each year:

1. Do one big "year-defining" thing - Something major that will stand out when you look back on the year. For Jesse, this has included things like biking across America.

2. Take a mini-adventure every other month - This could be a weekend trip, trying a new activity, or anything to break out of the routine.

3. Add a new positive habit each quarter - Things like meditation, drinking more water, etc. to continually improve.

By following this system over many years, Jesse says you can shape an incredible life filled with adventures and accomplishments. He notes that if you live to 85 and do this annually, you'll have "50 year-defining things and 300 mini-adventures - you're starting to shape an insane life."

Building Successful Businesses

Jesse has founded or co-founded multiple companies that have sold for hundreds of millions or billions of dollars, including Marquis Jet and Zico coconut water. When asked about the keys to building a successful business, he emphasizes a few key points:

• Enthusiasm is critical - You need enthusiasm not just for your product, but for the process of being an entrepreneur.

• Focus on the customer and product - The product has to be genuinely good and fill a need.

• Make it fun - "You want to make money, you want to have fun, and you want to have fun making money."

• Be different - Either create something brand new or make an existing product/service significantly better.

• Be authentic - Stand out by being true to yourself and your unique story/perspective.

Jesse also notes that building a big business often takes more time than people realize. While some get rich quick, for most people "you're going to make 5 to 10 times more money in your 40s and 50s than you will in your 20s and 30s" as you gain experience and connections.

Leadership and Empowering Others

Many of Jesse's former employees and interns have gone on to major success, founding companies worth hundreds of millions or billions. When asked about his leadership style, Jesse says:

"I think that you have to put confidence in people... I am good at giving people confidence and belief, and that's really important because you have to believe in the end of your story."

He tries to instill the conviction in people that they can achieve great things. Jesse also emphasizes the importance of learning from others, noting how he would constantly observe successful people and ask them questions about their habits and approaches.

Marriage and Family

Jesse has been married to entrepreneur Sara Blakely (founder of Spanx) for 15 years. He shares some insights on what has worked for them in their relationship:

• Align on core values, but let your partner be who they are
• Communicate beyond just transactional conversations
• Get in front of problems early rather than letting them fester
• Be solution-oriented when addressing issues
• Create fun traditions and experiences together as a family

With their kids, Jesse focuses on praising effort rather than just results. He also tries to reframe negative self-talk, like when his daughter says she "can't" do a math problem.

Ultimately, Jesse emphasizes that every marriage is different and you have to find what works for your specific relationship and family dynamic.

Living a Story-Worthy Life

A key theme throughout the conversation is Jesse's focus on collecting memorable experiences and stories. He invests heavily in adventures and trips, both with friends and family.

Jesse shares a poignant story about finding an autobiography his grandfather had written, hidden away in a safe. It made him reflect on the importance of the stories and lessons we pass down.

He encourages people to think about what stories will fill their own "book in the safe" - the legacy and memories they'll leave behind. Jesse's philosophy is to continually seek out new adventures and experiences:

"I am so deeply invested in spending my money on experiences... I'm going on a sauna tour of Finland with 10 friends in February. I rode my bike across America with 10 friends last year. I'm going on trips with my family... I got scuba certified with my son."

Even when he was young and broke, Jesse sought out free experiences and adventures rather than just sitting on the couch. He believes anyone can find ways to create memorable moments and stories, regardless of their financial situation.

Ultimately, Jesse's approach is about living life to the fullest and not settling for being the "80% version" of yourself. By continually pushing outside your comfort zone, trying new things, and creating memorable experiences, you can craft an extraordinary life story worth telling.

Key Takeaways

• Get over the fear of embarrassment - it's liberating and opens up opportunities
• Intentionally schedule adventures and memorable experiences
• Do one major "year-defining" thing annually
• Focus on enthusiasm, product quality, and differentiation in business
• Instill confidence and conviction in the people you lead
• Align on core values in relationships, but let your partner be themselves
• Invest in creating stories and experiences, not just accumulating things
• Live in a way that you'll be proud of when looking back at age 85
• Anyone can find ways to have adventures, regardless of finances
• Push yourself to be the 100% version of yourself, not the 80% version

Article created from: https://www.youtube.com/watch?v=byqZNfevXZM