Mike Tyson’s road to a second chance

The polarizing highs and lows of one of the most thrilling, controversial and celebrated boxers of all time

Posted by: Team Tony

A special note to our audience: This episode contains language and subject matter that may not be appropriate for some listeners.

A lot of famous people are known by just ONE THING: a winning shot in a championship game, saying the wrong word or phrase in a public speech or even a cameo in a Hollywood movie. You’re about to hear Tony interview someone who has had multiple defining moments that people remember him by.

Mike Tyson is a household name – you might know him as an American former professional boxer or maybe by his cameo in the movie “The Hangover.” But he’s far more complex than any of these things alone.

Tony has known Mike Tyson for a long time. In fact, Tony first interviewed him over 20 years ago. They had a powerful conversation shortly after Mike’s highly publicized incident with Evander Holyfield, during a dark time in his life. Today, he’s been given a second chance. His journey has been long and winding, but he finally found the courage to face his demons. As he so powerfully puts it: “There’s no limit to what I’m capable of doing. Imagine if I would have given up … I would have never realized this beautiful life.”

A rough childhood

You’ll hear Mike open up about his childhood, which was marked with violence from the start. He grew up in Brownsville, a crime-infested neighborhood in Brooklyn, where bone-crushing street fights made self-defense a necessary evil. He was introduced to cocaine, marijuana and alcohol at nine years old. He got in so much trouble, the cops knew him by name. Finally, he was sent to juvenile detention for two years in upstate New York. It ended up being a turning point: He met former professional fighter Bobby Stewart and began boxing.

Professional success

After being discovered by Bobby, Mike began training with the legendary Cus D’Amato, who also trained Hall of Famers Floyd Patterson and José Torres. Cus became not only Mike’s coach, but a father figure, mentor and role model who had a massive influence on every aspect of his life. Cus died when he was 19 – and he used his grief as fuel, becoming the youngest heavyweight champion in the world a year later. From there, Mike quickly emerged as “Iron Mike Tyson” – the self-proclaimed “baddest man on the planet” and the undisputed heavyweight champion of the world.

Wrestling the demons

People think that when you succeed, the world is your oyster. But for many people that is not the case – including Mike as well as many other celebrity athletes. Even with all the money in the world, he was miserable. He was plagued by negative self-talk. He trusted no one. His rage and madness in the ring that won him so many matches eventually caught up with him. Outside, in the real world, there were severe consequences. He was convicted of a felony, went to prison, lost his fortune and spent years battling addiction to alcohol and drugs. His journey led him to a life-changing realization: “I had to learn to trust myself, love myself, respect myself.”

A new mindset

The man you’re about to hear in this episode is completely different than the one he used to be. He’s sensitive, remorseful of his past and grateful for his second chance. He’s vulnerable. You’ll even hear him get emotional as he talks about his relationship with Cus D’Amato. He practices gratitude. He keeps a positive perspective and has compassion for others. He gives back. And he truly believes in himself and loves himself. He’s finally learned, “We’re a lot stronger than we believe we are.”

Today, Mike’s life has a new meaning. It’s a life fueled by love – not hate. He’s in pursuit of wellness, for both mind and body – and is focused on creating balance, mindfulness and a strong spirit. He’s a true example of perseverance, despite all that stands to dissuade and dissolve it.

Episode notes

[03:29] The conversation between Mike and Tony 20 years ago
[04:10] Why Mike Tyson impresses Tony so much
[05:00] Mike describes his tough childhood
[05:40] Mike getting bullied, and winning his first fight
[06:25] Mike’s first fights were in his neighborhood
[06:47] Getting introduced to drugs at 9 years old
[07:14] Mike gets shipped off to a reformatory
[07:36] Mike meets former professional fighter Bobby Stewart
[08:01] Mike learns how to box from Bobby Stewart
[08:30] Mike meets Cus D’Amato
[09:21] The Larry Holmes and Muhammed Ali fight
[10:12] Mike gets emotional thinking about Cus D’Amato
[10:40] The influence Cus D’Amato had on Mike
[11:00] Mike’s experience of being hypnotized by Cus D’Amato
[11:45] Mike fights Larry Holmes
[12:15] When Mike starts to believe in himself
[12:36] The impact of Cus D’Amato’s death
[12:55] Dealing with the demons of wanting to hurt people
[13:34] The reason why Mike lost the Holyfield fight
[14:04] Mike’s experience of the racial divide in prison
[15:14] When you don’t have love, you want power
[16:08] Mike’s dedication to his family
[16:51] The effect of Mike’s low self esteem on his behavior
[17:55] How Mike dealt with his pain and learned to trust again
[18:35] The price Mike paid for fame
[19:30] How Mike has redefined the relationships with his loved ones
[21:35] Mike’s relationship with pigeons
[22:23] The story of how Mike got a tiger
[23:43] Why Mike believes Cus D’Amato was put in his life
[24:38] What Mike gave to Cus D’Amato
[25:43] The desire to keep fighting after the fight
[26:56] How willingness to sacrifice gives you the edge
[27:39] The power of doing what your opponent won’t
[28:46] Where Mike’s drive really came from
[29:06] Mike gets out of prison and realizes he wasn’t God
[30:24] Mike makes major changes after the death of his daughter
[30:52] Mike’s life-changing experience with The Toad
[31:21] Tony resolves his fear of death with The Toad
[32:49] Mike faces his demons under The Toad and emerges as a new man
[34:19] Mike’s experience of life after doing The Toad
[34:45] How doing the movie “The Hangover” changed Mike’s life
[35:55] The story of Mike starting his Broadway show
[37:31] How the show went from a drama to a comedy
[38:16] Mike’s upcoming Netflix documentary
[38:44] The incredible accomplishments of Mike’s six children
[39:22] Mike’s new journey with his cannabis ranch
[40:49] The impact that cannabis has on health
[41:05] A day in the life of Mike Tyson, today
[41:30] How surrendering leads you to a beautiful life
[41:53] How Mike treats his relationships today
[42:27] The compassion and love that Mike has for people today
[43:07] Mike’s advice to people going through dark times

Mike Tyson overcame great odds to be where he is today – not only his success as a boxer, but his success in transforming his entire mindset. He learned how to let go of the limiting beliefs that were holding him back. He discovered the power of changing his story and giving new meaning to his experiences, giving him the second chance to experience a beautiful life.