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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Gary Vaynerchuk, commonly known as Gary Vee, is an influential entrepreneur, speaker, and internet personality, best known for his expertise in digital marketing and social media. Starting his career in his family's wine business, Gary's innovative approach to e-commerce and content creation catapulted the business from a local enterprise to a national leader in wine retail. He later founded VaynerMedia, a leading digital agency that services Fortune 500 clients across the globe.

In this episode, Gary shares his unfiltered insights on the dynamics of building and scaling businesses, the evolution of consumer engagement, and the relentless pursuit of hustle. He opens up about his journey from a Belarusian immigrant to a global business mogul, reflecting on the impact of his heritage on his work ethic and entrepreneurial spirit. With his characteristic candor and deep passion for empowering others, Gary offers listeners not only a glimpse into the competitive world of digital marketing but also imparts profound lessons on perseverance, vision, and personal branding.

Timestamps:
00:00 - Gary Vee discusses the early influence of social media on his content creation, specifically Twitter.
03:02 - A discussion on strategic moves in poker and their parallels to business decisions.
06:02 - Gary shares his experience of working in his father's store during college and the lessons learned.
09:02 - The conversation covers the significant impact of actions in leadership and business.
12:02 - Gary talks about the inception of his agency and his disbelief at the scale of corporate engagement in the late 2000s.
15:05 - Reflections on personal moments, including a honeymoon in Hawaii and the settings that influenced his life.
18:05 - A hypothetical scenario is discussed where a major social platform is forced to sell, reflecting on the potential impacts.
21:06 - Discussion of missed opportunities and the financial implications of quick decisions in business.
24:07 - Gary Vee emphasizes the power of word-of-mouth in marketing and personal convictions.
27:09 - Analysis of the cost-effectiveness of Super Bowl advertising and its comparison to other marketing platforms.
30:10 - Advice for professionals feeling dissatisfied with their job, stressing the importance of commitment and effort.
33:10 - Gary discusses the importance of setting goals and the effectiveness of writing them down.
36:12 - A personal reflection on family dynamics and the distribution of affection among siblings.
39:15 - Gary shares his views on retirement, emphasizing his desire to never stop working.
42:18 - Thoughts on legacy and giving back, including advice Gary would offer to his younger self.

In Search of Excellence Podcast - with Randall Kaplan

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One-on One Coaching: I coach a select group of high achievers on how to elevate their careers, grow their businesses, and unlock their full potential.
Apply Here = https://www.randallkaplan.com/coaching

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Website: https://www.randallkaplan.com/

Coaching and Staying Connected:

1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn

Gary Vaynerchuk, commonly known as Gary Vee, is an influential entrepreneur, speaker, and internet personality, best known for his expertise in digital marketing and social media. Starting his career in his family's wine business, Gary's innovative approach to e-commerce and content creation catapulted the business from a local enterprise to a national leader in wine retail. He later founded VaynerMedia, a leading digital agency that services Fortune 500 clients across the globe.

In this episode, Gary shares his unfiltered insights on the dynamics of building and scaling businesses, the evolution of consumer engagement, and the relentless pursuit of hustle.

Timestamps:

02:41 - Introduction.
05:21 - Gary Vee narrates the immigration challenges faced by his family leaving the Soviet Union and adjusting to life in America.
08:02 - Gary Vee talks about his father's entrepreneurial journey from managing a store to owning it and the lessons learned from observing his work ethic.
10:41 - Randall Kaplan praises the inherent strength and resilience of influential women in challenging environments.
13:20 - Randall Kaplan shares an emotional personal story, underscoring the importance of strong family values.
16:04 - Gary Vee elaborates on the supportive dynamics within his extended family and the emotional bonds that shaped his upbringing.
18:41 - Gary Vee emphasizes the crucial life skill of dealing with adversity and finding comfort in uncomfortable situations.
21:20 - Gary Vee reminisces about his childhood summers, filled with familial connections and simple joys.
24:03 - Randall Kaplan reflects on his childhood outdoor activities, noting the less supervised yet richly interactive play of his youth.
26:40 - Randall Kaplan discusses overcoming personal challenges and the motivation behind his drive to succeed despite obstacles.
29:23 - Gary Vee debates the nature of entrepreneurial success, questioning if innate talent is a necessary component and sharing his personal experiences with early business ventures.
32:03 - Gary Vee discusses his youthful business initiatives, including running a lemonade stand and the creative ways he expanded it.
34:44 - Gary Vee recalls his childhood efforts to earn money through various small ventures, from selling flowers picked from neighbors’ gardens to singing carols.
37:22 - Gary Vee shares his philosophy on the value of hard work over formal education, reflecting on his personal and family experiences.
40:00 - Gary Vee looks back on a defining weekend in his youth that solidified his passion for business and innovation.

In Search of Excellence Podcast - with Randall Kaplan

Listen to this episode on the go!
Apple Podcasts: https://podcasts.apple.com/us/podcast/in-search-of-excellence/id1579184310
Spotify: https://open.spotify.com/show/23q0XICUDIchVrkXBR0i6L

One-on One Coaching: I coach a select group of high achievers on how to elevate their careers, grow their businesses, and unlock their full potential.
Apply Here = https://www.randallkaplan.com/coaching

Follow Randall!
Instagram: https://www.instagram.com/randallkaplan
TikTok: https://www.tiktok.com/@randall_kaplan
Twitter / X: https://x.com/RandallKaplan
LinkedIn: https://www.linkedin.com/in/randallkaplan/
Website: https://www.randallkaplan.com/

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