Jesse Itzler: From Making Jingles To A Creating a $5-Billion-Dollar Company | E95

Welcome to another episode of In Search of Excellence! My guest today is the amazing Jesse Itzler.Jesse is a serial entrepreneur who has built and sold five companies, including Marquis Jet and Zico Coconut Water. He is an Emmy Award winner, a former rapper and former manager of Run DMC, a globally recognized keynote speaker, and a part-owner of the Atlanta Hawks NBA basketball team.He's also a passionate endurance athlete who has run more than 35,000 miles over the last 25 years, including 50+ marathons. Jessie is also the author of two awesome best-selling books, Living with the Seals 31 Days: Training with the Toughest Man on the Planet and Living with the Monks: What Turning off My Phone Taught Me About Happiness, Gratitude, and Focus. Time stamps:01:54 The influence of Jesse’s parents- They showed up for everything- They let him explore- They didn’t over-schedule him- Didn’t teach him about hard work, he watched them doing it04:12 How much is his personality a part of his success?- He has problems with memorizing things- He is great at storytelling- His personality was essential for his success05:58 The entrepreneurial gene- Jesse’s grandfather was born in poverty in Russia- He immigrated to America and came with nothing- Jesse’s grandfather and father worked very hard- Jesse grew up middle-class07:42 Should kids go to college?- Jesse went to everything and was exposed to knowledge and people- His mom encouraged him to be curious and take every opportunity- He was aware of the time and urgency12:50 The start of Jesse’s career – getting a foot at the door- Jesse's record deal – go to every door until someone says yes- He got a deal from a record label called Delicious Vinyl- It’s essential to get a foot at the door and get into the system 16:47 The ridiculous offer and believing in yourself- Started the music business doing commercial jingles- He lived on his friend’s couches- Someone offered him $10,000 for 10% of his future earnings- Can you? vs. Will you?20:32 The advice to young entrepreneurs- Some businesses require capital- Selling out equity to employees, friends, and family- Under-promising and keeping things simple is a better strategy- Take advice, go through the pros and cons, and think through the worst-case scenario24:39 How to bounce back from a failure?- Sold his business for $1 million- Tried many different things and failed- Extremely enthusiastic about trying fun things and projects- Sold celery and carrot sticks and loved it even without the profit- In business, three strikes and you're not out 29:30 Is there a time to stop trying?- Jesse kept going despite failures- He never stopped- The tolerance of embarrassment- Never got embarrassed by his failures31:51 The value of relationships- Wanted to start a private jet company but didn’t have jets- Met with the president of the largest private jet company in the world – Net Jets- Got the deal and built a $5 billion companyResources Mentioned:Type in EXCELLENCE15 for 15% off The Big A## Calendar! About Randall Kaplan: Randall Kaplan is a serial entrepreneur, venture capitalist, executive coach, co-founder of Akamai Technologies, founder and CEO of JUMP Investors, and host of In Search of Excellence. Through his Extreme Preparation™ methodology, he helps founders, executives, business owners, and ambitious professionals improve strategy, communication, decision-making, and execution.Coaching and Staying Connected:1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn | X