The way Mike Tyson reinvented himself is wild: From $400M to $23M in debt, and now he makes $20M off one fight with Jake Paul. Here’s the iron story of Tyson’s rise and fall.

Mike Tyson was born in 1966 in Brooklyn, New York. He grew up in a tough neighborhood surrounded by crime and poverty. By the age of 13, he had been arrested 38 times. Boxing became not only his escape, it was his whole life.

At 16, Tyson met trainer Cus D’Amato, who became a father figure and mentor. D’Amato taught him boxing, discipline, and self-belief. He famously said, “The most important part of boxing is psychology.” Under D’Amato, Tyson’s career took off.

By 20, Tyson became the youngest heavyweight champion in history. His ferocious style and unmatched power earned him the nickname “Iron Mike.” In the late ’80s, Tyson dominated boxing, earning $400M and becoming a cultural icon.

Tyson was truly the baddest man on the planet. • Abstained from sex for five years early to focus on boxing • Offered $10,000 to fight a gorilla at a zoo because the gorilla was bullying others. • Owned three Bengal tigers, spending $270,000 for their purchase and care.

But his success didn’t last. In 1990, Tyson suffered one of the biggest upsets in boxing history, losing to Buster Douglas. Legal troubles, reckless spending, and a prison sentence soon sent his life spiraling out of control.

By 2003, Tyson filed for bankruptcy. Despite earning $400M, he was $23M in debt due to lawsuits, mismanagement, and extravagant spending. He later admitted, “I was young, rich, and stupid.”

But Tyson didn’t stay down. In the 2010s, he reinvented himself as an entertainer and entrepreneur: • Launched “Mike Tyson Mysteries,” an animated TV show • Wrote Undisputed Truth, a bestselling memoir • Acted in movies like The Hangover.

One of Tyson’s biggest come back moves was entering the cannabis industry. In 2016, he launched Tyson 2.0, a cannabis company now worth $160M. His ranch reportedly earns over $1M a month and is expanding into global markets.

Tyson also built a podcast empire with Hotboxin’ with Mike Tyson. The show features celebrities, athletes, and entrepreneurs, and it became wildly popular. Tyson’s ability to connect with people is part of what makes him such a success.

On Nov 15, 2024, Mike Tyson returned to the ring to face Jake Paul at AT&T Stadium in Texas. It marked Netflix’s first live boxing event and broke viewership records. The bout generated over $17.8M in gate revenue, the highest-grossing boxing event in history outside of Vegas.

Jake Paul won the fight by unanimous decision. Tyson earned at least $20M from the bout. At 58, Tyson’s participation proved his star power is unmatched, even in defeat. This fight reminded the world why Mike Tyson is still one of boxing’s biggest draws.

I grew up watching Tyson dominate the ring. I remember the shocking moment he bit Holyfield’s ear. Tyson’s life shows that even the strongest can fall. It’s not just about K.O’s. It’s about the strength of getting back up when you get knocked down.

Mike Tyson’s life is a masterclass in reinvention. From $400M earned to $23M lost to a $160M cannabis empire, he’s proof that failure is not the end. As Tyson says, “It’s not over until you’re dead.” What’s your favorite Tyson moment?