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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Apple Podcasts: https://podcasts.apple.com/us/podcast/in-search-of-excellence/id1579184310
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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:

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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.

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/

Get More Excellence! In Search of Excellence Clips: https://www.youtube.com/@iseclips

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In this extraordinary episode of In Search of Excellence, I sit down with the legendary Mike Tyson — former heavyweight boxing champion of the world, cultural icon, entrepreneur, and philanthropist.
Mike opens up like never before about confidence, redemption, pain, preparation, and success. From his rise as the youngest heavyweight champion in history to his darkest battles with drugs, prison, and public controversy, Mike shares the raw truths that shaped his life.

We dive into his iconic fights, including Evander Holyfield and Buster Douglas, his struggles after boxing, and his transformation through family, philanthropy, and Tyson 2.0. He speaks candidly about the role of cannabis, psychedelics, and extreme preparation in finding peace and purpose.
Mike also reflects on fatherhood, his marriage, and what true success and happiness mean — offering advice that will inspire anyone facing setbacks, doubts, or big dreams.

Timestamps / Chapters
00:00 - Mike Tyson's Journey to Success
01:53 - The Role of Money and Success
06:59 - Prison Experience and Personal Growth
15:35 - Challenges and Redemption
15:49 - Friendship and Mentorship
22:47 - Life After Boxing
23:05 - Philanthropy and Giving Back
23:41 - Advice for Young People
33:35 - Reflections on Life and Death
38:48 - Final Thoughts and Future Plans

Highlights from this Episode:
Why confidence breeds success — and how Mike applied it inside and outside the ring

The mindset of extreme preparation and learning from Muhammad Ali
Behind the scenes of the infamous Holyfield “Bite Fight”
What Mike learned from losing to Buster Douglas
How prison became the “three most valuable years” of his life
The role of cannabis and psychedelics in his transformation
Powerful lessons on family, fatherhood, and love
The mission of the Mike Tyson Cares Foundation
What motivates Mike Tyson today
Whether you’re chasing greatness, rebuilding after failure, or seeking a deeper understanding of success, this conversation with Iron Mike is one you won’t forget.

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/

Get More Excellence! In Search of Excellence Clips: https://www.youtube.com/@iseclips

Coaching and Staying Connected:

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

In Search of Excellence Podcast - with Randall Kaplan

My guest today is Mike Tyson, a former heavyweight boxing champion of the world and one of the greatest boxers of all time! At the age of 20, he became the youngest boxer ever to win a heavyweight title. He was the first heavyweight boxer to simultaneously hold WBA, WBC, and IDF titles and a member of the international boxing Hall of Fame.

Mike has appeared in many movies and TV shows. He is the actor and creator of a one-man Broadway show Undisputed Truth, and the author of the best-selling book of the same name.

Mike is also a very successful entrepreneur and a founder of two cannabis companies, including Tyson 2.0. He is an incredible person and a dedicated philanthropist through his Mike Tyson’s Care foundation, and the support of other charities including The Make a Wish Foundation and The Special Olympics.

00:00 Mike’s childhood
His dad was a pimp, his mom an alcoholic and a sex industry worker
He was bullied in his childhood ("you can’t run from them, you must confront them")
Started robbing people to buy food for his pigeons
A traumatic event with the birds that changed him
Mike's first fight and from being bullied, to being the bully
Went pick-pocketing and stealing with his friends
Started with crime at 11, by the age of 13, he was arrested more than 37 times
The stealing mentality - nobody else matters
His mom encouraged him to steal (his goal was to be a professional criminal)

18:13 Juvenile facilities and Mike’s first steps in boxing
Watched the movie “The Greatest”, the story of Mohammed Ali
Transferred to Elwood Cottage
Mike was always handcuffed in a dangerous environment
Met Bobby Stewart who inspired him to finish school and started training him
At 13, Bobby wanted to take him to the next level - introduced him to Cus D'Amato

21:14 Mike’s first mentor - Cus D'Amato
Relationship with Cus D’Amato (Cus taught him to never give up)
Cus became a father figure for him
The time Mike first experienced love
Cus saw in him the future world champion
Working out for 6 hours a day while going to school
Wanted to get kicked out of school, but Cus didn’t allow that
There is no progress without struggle (study about rats)

29:32 The beginning of his fighting career
At 18, a fight with Hector Mercedes - beat him in one round
Wasn't afraid of losing, but being a bad loser
Mike's desire to be the world champion consumed him completely
Became the youngest boxing champion ever
His mother’s reaction - never got affirmed by her

34:47 From millions of dollars to bankruptcy
Started making millions of dollars (became highest paid athlete in the world)
Went bankrupt being reckless, didn’t know how to manage money as a street kid
Being rich and going broke multiple times
Fame and money won’t make you happy
Become your own alarm system
The pain is the same at the top and the bottom of the world

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

Follow Randall!
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1-on-1 Coaching: https://

Coaching and Staying Connected:

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Legendary surfer Laird Hamilton joins host Randall Kaplan on the In Search of Excellence podcast for a raw and unforgettable conversation about innovation, mindset, and personal transformation. Hamilton shares how he co-invented tow-in surfing, stand-up paddleboarding, and surf foiling, turning niche ideas into billion-dollar global sports.

From serving as Kevin Costner’s stunt double in Waterworld to surviving a near-death experience in the ocean, Laird opens up about the moments that shaped his fearless mentality. He dives deep into the philosophy of pain, extreme preparation, mentorship, and the pursuit of purpose. He also explores the challenges of public life, the importance of family, and how to thrive under pressure.

Whether you're an entrepreneur, athlete, or simply someone seeking inspiration, this episode offers powerful life lessons from one of the most innovative figures in extreme sports history.

🎧 Episode Highlights and Timestamps:

• 00:00 – Laird Hamilton’s Impact on Surfing and Paddleboarding
• 00:48 – Kevin Costner Stunt Double & Near-Death Experience
• 05:19 – Hawaii Five-0 Appearance & How Pain Can Be a Great Teacher
• 08:17 – The Role of Extreme Preparation in Achieving Success
• 17:51 – Co-Inventing Stand-Up Paddling with Tom Jones
• 25:07 – The Evolution of Surfing and Rise of Foiling
• 29:16 – Mentorship and Its Influence on Growth
• 40:52 – Family, Relationships, and Defining Personal Success
• 41:07 – Facing Controversy and Shaping Public Perception
• 50:49 – Marriage, Partnership, and Life in the Public Eye

👉 Listen now to hear Laird Hamilton’s incredible journey—and get inspired to break boundaries, defy expectations, and live with discipline and excellence.

🔔 Don’t forget to subscribe so you never miss an episode filled with wisdom, success stories, and powerful insights.

🎙️ 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

For more information about this episode, visit https://www.randallkaplan.com/

Follow Randall!

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

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Get More Excellence! In Search of Excellence Clips: https://www.youtube.com/@iseclips

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In this raw and riveting episode of In Search of Excellence, legendary surfer and ocean pioneer Laird Hamilton shares his incredible story — from his unconventional birth using a method like a reverse hair dryer, a wild childhood in Hawaii, and surviving abuse and racism, to revolutionizing surfing with inventions like tow-in surfing, foilboarding, and modern paddleboarding.

Laird opens up about his near-death experience on Waterworld, why he never competed professionally, how he rescued another surfer by swimming naked, and what makes paddleboarding and foiling $4 billion industry rooted in innovation, art, self-expression, and raw danger. He reflects on growing up with an abusive father, bullying, fear, extreme danger, the challenges of big-wave surfing, near-death experiences, education, family, mentorship, the relentless pursuit of greatness, and his view on being considered the greatest surfer of all time.

From modeling for renowned fashion photographer Bruce Weber and being on the cover of Italian Vogue, to surfing 50-foot monsters at Jaws and Nazaré, this episode delves into what it means to master chaos, seek purpose over praise, and remain humble while pushing human limits.

0:00 – Laird Hamilton's Revolutionary Contributions to Surfing
19:00 – Laird Hamilton's Unique Birth and Early Life
19:13 – Challenges and Lessons from Laird Hamilton's Childhood
19:31 – Laird Hamilton's Early Surfing Career and Modeling
21:48 – Laird Hamilton's Views on Education and Career
25:19 – The Evolution of Surfing and Laird Hamilton's Contributions
29:45 – The Popularity and Challenges of Surfing
38:10 – The Impact of Big Wave Surfing and Nazare
48:26 – The Science and Experience of Big Wave Surfing
50:36 – Laird Hamilton's Philosophy and Approach to Life

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

For more information about this episode, visit https://www.randallkaplan.com/

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/
1-on-1 Coaching: https://intro.co/randallkaplan

Get More Excellence!
In Search of Excellence Clips: https://www.youtube.com/@iseclips

Coaching and Staying Connected:

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In this powerful episode, Mike Meldman — real estate mogul, co-founder of Casamigos Tequila, and founder of Discovery Land Company — shares the remarkable story behind his journey from instinct-driven entrepreneur to one of the most influential figures in luxury real estate and lifestyle branding.

Mike dives deep into how Casamigos, a tequila brand originally created with George Clooney “just for fun,” skyrocketed from a personal project to a billion-dollar business — despite having no plans for mass distribution. From there, he walks us through the origin and explosive growth of Discovery Land Company, a visionary take on private communities built around service, family, and meaningful experiences — not just golf.

One of his standout projects, Kukio in Hawaii, started with an underwhelming plot of lava rock but became one of the most successful resort communities in the U.S., selling $50 million worth of real estate in just 90 days. Mike reveals how a courthouse bidding war with Mitsubishi, unconventional thinking, and meticulous attention to member experience helped make Kukio what it is today.

But his ambition didn’t stop there. Mike also discusses his 7.5% ownership stake in the Las Vegas Raiders, the importance of choosing the right people to surround yourself with, and how he's used strategic investments in companies like Vuori (valued today at $7 billion) to expand his brand’s reach far beyond real estate.

He speaks candidly about the challenges he's faced — including the emotional toll of two failed marriages — and reflects on what truly matters: family, discipline, integrity, and giving back. Through the Discovery Land Company Foundation, Mike supports children’s charities and community development around each of his projects, making sure that luxury living doesn't come at the cost of social impact.

This episode is more than a conversation — it’s a blueprint for anyone who wants to build something iconic from scratch, stay grounded while chasing massive success, and leave behind a legacy that matters.

Timestamps:
00:00 – Casamigos and Discovery Land Company
00:58 – Investment in Las Vegas Raiders
03:00 – Kukio Project in Hawaii
06:44 – Challenges and Successes at Kukio
09:58 – Gaza Ranch and Personal Reflections
12:30 – Preparation and Team Building
21:07 – Acquisition of Yellowstone Club
27:58 – Investments and Strategic Partnerships
35:42 – Philanthropy and Community Impact
40:12 – Personal Reflections and Future Goals

Coaching and Staying Connected:

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