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

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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

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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/

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