Want to learn how I got my big break? DM me the word “LETTER” on Instagram for a guide on how to get any job you want: https://www.instagram.com/randallkaplan 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 it

05:58 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-class

07:42 Should kids go to college?

- College gave him some important skills
- He 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 urgency

12:50 The start of Jesse’s career – getting a foot at the door

- Jesse wanted to have a record deal
- His approach – 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?

24:39 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
- Failures didn’t bother him
- 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 failures

31:51 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 his daughter onstage with Christina Aguilera, a year prior
- He presented him his idea
- Brought his own focus group rather than pitching on a PowerPoint
- If you have one chance, you have to be prepared and stand out
- Got the deal and built a $5 billion company
 
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