10 Lessons From Mike Tyson’s Legends Only League Debut

Last week, a very empty Staples Center in downtown Los Angeles housed a much anticipated match between 51-year-old four division world champion Roy Jones Jr. and 54-year-old boxing legend Mike Tyson. The match, which ended in a draw, served as opening night for Tyson’s recently launched Legends Only League, through which he is partnering with social media streaming app Triller and sports betting company DraftKings to host a series of boxing matches. The debut event also featured veteran boxers and up-and-comers, such as Juiseppe Cusumano, Greg Corbin, Edward Vazquez, Irvin Gonzalez, Jamaine Ortiz, Sulaiman Segawa, Badou Jack and Blake McKernan, as well as YouTube sensation Jake Paul and former NBA Champion Nate Robinson.

Undercard sports betting on DraftKings was available in Colorado, Indiana, Iowa and Tennessee, as well as in Illinois, New Hampshire and New Jersey, where bettors could wager on the main card. The biggest gamble of the night was made by Tyson, who hasn’t boxed in 15 years and used the draw of his celebrity to launch Legends Only League. Here are 10 lessons that business leaders can take away from the night.

1. Be Prepared For Anything

Tyson’s Legends Only League and its partner, Triller, went into the event prepared for anything. California’s rising coronavirus cases led to new restrictions that prevented fans from attending in person. The event also lost one of its performers, Lil Wayne, just two hours before the opening match. The co-organizers were still able to pull off the event while respecting the 300-person limit for staffers and performers. And its reach wasn’t compromised: The event garnered more than five million pay-per-view pre-orders, a testament to the time and precision that went into planning before a punch was even thrown. 

2. You’re Only As Big As Your Last Win

Even casual boxing fans knew to take Jake Paul for the win. Paul had been training as a boxer for months and had a record of 1 – 0, while Nate Robinson, the first three-time NBA Slam Dunk Champion, had less experience and a boxing record of 0 – 0. The bout wasn’t a title match, yet both had their reputations on the line. A loss would destroy the hype they had built around their recent career changes. In the end, Paul was victorious, but his work is far from done—a future loss could just as easily call into question his pivot to boxing. 

3. Actions Speak Louder Than Words

From the moment the fight was announced, it was clear that Paul was more prepared than Robinson. Paul had been following a rigorous two-a-day training schedule, while his opponent prepared with hype talk. Robinson began the fight on the offensive, rushing head first at Paul, throwing a flurry of punches with hopes of landing a lucky one. But each time, Paul would return, successfully connecting counter punches of his own. The fight was over before it began. Entering into a situation prepared, with confidence and tenacity, gives you a better shot at a good outcome.

4. Proof Of Concept Comes In Many Forms

With this boxing showcase being the first event for Tyson’s League Of Legends, there was a lot at stake. Millions of fans were watching via pay-per-view, as were hundreds of potential sponsors, identifying product placement opportunities and unique offerings. Sponsors such as Red Bull were vying to get involved on Twitter, while rappers and athletes including Odell Beckham Jr. jokingly made challenges. Tyson wanted to show that professional boxing doesn’t have to live in its current, archaic form and that there are many paths to the coveted pay-per-view slot. Saturday night he solidified League Of Legends as being one of those paths. 

5. Give Yourself Space For Growth

One of the major takeaways was the special guest from Saturday night’s festivities: the new-and-improved, business-minded Tyson that appeared before us. Tyson was calm, poised and very focused on ensuring a successful night. He spoke of his personal growth  in the 15 years since his last professional fight. “Everybody knows I can knock people out,” Tyson said. “I knock somebody out and it’s quick and it’s over, but I think that going the distance and showing endurance is key. I learned in my earlier years that you’re not going to be able to knock everybody out. At 54 years old, I’ve been training for duration. I’m more interested in that because I’m still learning and over time I’ve learned that I knew nothing when I was champ.”

After the successful launch of his podcast, Hox Boxin with Mike Tyson, and his cannabis brand, Tyson Ranch, he believes he can be an asset, rather than a liability, to younger fighters. Tyson adds: “I like who I am now. I never liked who I was before.” 

6. Under Promise, Over Deliver

Former two-division title holder Badou Jack took a different approach to his cruiserweight fight with the previously undefeated Blake McKernan. He wasn’t overly braggadocious and he didn’t speak much outside of sanctioned media events, focusing on the task at hand: Improving his record of 12-3-3 to 13-3-3. His silence leading up to the fight, and the few verbal jabs he threw in its aftermath, serve as an important message: Focus on delivering.

7. Expect The Pivot And Embrace It

When the Covid-19 pandemic began, one of the hardest-hit industries was entertainment. Artists that rely on touring for a living saw their schedules dry up and began to rely on organizations like the Recording Academy’s Music Cares for support, while others had to pivot to other businesses. Rising coronavirus cases in California have led to more stringent restrictions on gatherings and live events, which is why Tyson’s League of Legends enlisted the help of Triller. The social media network put on a fully produced and socially distanced mini concert with performances by French Montana, Swae Lee, Snoop Dogg, Wiz Khalifa, YG and Saint Jhn that kept fans engaged throughout the night and attracted a younger audience.

8. Find A Market Need

While the majority of professional boxers are people of color and are embraced for their role in the sport, the culture of those boxers is not. The other issue, as with most sports, is that once pro athletes pass what their respective leagues or organizations consider their prime, they are discarded. 

Tyson got the idea for the Legends Only League while watching former NFL player Jerry Rice serve as a sports competitor in a football combine. He didn’t think he was getting the respect he deserved and wanted to create a space for veterans like Rice who have made history in their younger years and may not be able to compete at the highest levels anymore but are still in shape to compete. “So what if he’s a few seconds off his broken world record?” asks Tyson. “So what’s that mean? We can’t watch Jerry anymore because he’s a few seconds slower than he used to be? What if he and a few of his friends who also kept in shape want to compete at that level?” 

Tyson discovered an untapped market for these retired athletes. A few leagues targeting retired basketball players have emerged over the last few years, including Ice Cube’s Big 3 and Elie Maroun’s Crew League, which saw Glenn “Big Baby” Davis competing on a team with Swae Lee. But Tyson is thinking outside of just boxing to “tennis, race car driving . . . anywhere we can celebrate our greats!” And his goal is to make it as authentic as possible. He adds: “You saw tonight? No boxing promoters were involved. When you see Legends Only, you know this is us playing by our rules.” 

9. Embrace Culture

Days before this event, it was revealed that the pay-per-views had broken the record for preorder sales. This can largely be attributed to the fact that this was Mike Tyson’s first fight in 15 years, but even he gave credit to influencers like Paul for bringing additional social media visibility. Traditional boxing organizations have yet to really embrace hip hop or social media. Boxing, as with most U.S., sports, started off with mostly white professional competitors and over time became dominated by Black professional competitors, yet the restrictions imposed by the traditional boxing clubs do not promote inclusion. 

The censorship that the majority of boxing leagues impose has been jarring for many fans who belong to younger generations. That’s why Twitter declared the true winner of the evening to be Snoop Dogg. His performance of classic hits was great, but his uncensored and unfiltered mix of comedy and commentary was a huge hit. 

10. Understand It’s Bigger Than You

The main draw for the event was Tyson and Jones Jr., but it was trending worldwide for many other reasons. From Saint Jhn’s surprise performance to Lil Wayne’s cancellation to Snoop’s commentary to Robinson’s knockout to Jake Paul’s subsequent challenge to Conor McGregor, this event was about more than the headlining fight. Tyson was still the brightest star of the night, but he was happy to champion the other participants, because the attention they received was attention League Of Legends received, and that was the whole point of the evening.