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

04:12 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 success

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?

20:32 The advice to young entrepreneurs- Some businesses require capital- Taking money comes with responsibility and pressure- 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 scenario

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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In Search of Excellence Podcast - with Randall Kaplan

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