Love him or hate him, few wrestling promoters found as much business success as formerWWEChairmanVince McMahon. While the recent Netflix documentaryMr. McMahonpaintedVince as someone who piledrived his legacywith questionable antics outside the ring, the decisions he made as a businessman made him the most powerful man in pro wrestling and a titan of the entertainment business.

Once upon a time, CM Punk said in one ofthe company’s best promos,“Vince McMahon is going to make money despite himself. He’s a millionaire who should be a billionaire.“Those words read as prophetic now that Vince McMahon is a billionaire, and here are some of the most successful business decisions that helped him get to that point.

throwback photo of Vince McMahon Sr. and Mr. McMahon talking backstage

10Buying the WWE From His Father

His First Major Business Decision

Vince McMahon’s acclimation into the wrestling world came off the heels of an absentee father,Vince McMahon Sr., who was building the basis of his future empire while his son lived in a trailer park, not even knowing who his father was. When he finally met his son at age 12, Vince Sr. changed his life, giving him a glimpse of what success could be, but Vince Jr. aspired for more. So, he went out of his way to get more.

Vince had a vision that his father couldn’t see: turning pro wrestling from a weird “sport” into a purely entertainment business. After working for years in his father’s company in various roles, Vince proposed a deal in which he would pay the elder McMahon in tri-monthly payments. If Vince Jr. missed even one payment, the deal would be null, and his father would keep the money. Against a sea of doubters, the young Vince did the unthinkable. Once he got the company, he was free to enforce his vision, which made pro wrestling what it is today.

Vince McMahon and Andre the Giant in Mr McMahon

9Going National

Going Against the Territories System and the NWA

Before wrestling became what it is today, every wrestling promotion operated under a territory system overseen by the National Wrestling Alliance. WWE (then WWF) worked in the northeast, and like other promotions,was expected to only work within their territory. Upon buying WWE, Vince McMahon had global, mainstream aspirations that conflicted with the regional wrestling industry. He immediately chose to invade these territories and break these agreements by booking and promoting shows in other territories.

If that weren’t enough, many of these territory’s top stars would opt to leave their respective promotions and flee for new opportunities with the WWE. This put Vince under scrutiny and even provoked threats against his life from other promoters. However,had Vince not rocked the boat like he did, WWE would not have become the worldwide superpower that it is today.

Vince McMahon WWF on TBS

8Signing Hulk Hogan

WWE’s First Top Guy and Wrestling’s First True Star

As Vince recalls in the documentary, his first meeting with Hulk Hogan came in the 70s when the future Immortal One still wrestled under the name Sterling Golden. It was Vince Sr. who would give Sterling the name ofHulk Hoganupon signing him. While Vince Sr. saw star potential in Hogan, he did not see any potential in Hollywood crossovers, so when Hogan took the opportunity to appear inRocky IIIas Thunderlips, it cost Hogan his job.

Vince Jr. had a different vision. When he finally bought the company from his father, he was quick to re-hire Hogan, who had already planted the seeds of Hulkamania in Verne Gagne’s AWA territory. Vince had a vision to build the future of his company around that man. Vince was able to lure Hogan back with the promise of making him a megastar and not hindering his Hollywood aspirations. The rest is history.Hulk Hogan’s era as the face and champion of the companymade WWE a mainstream entertainment phenomenon.

Vince McMahon vs Hulk Hogan at WrestleMania 19

7Using Celebrities

The Rock n Wrestling Era Pushed the WWE to the Top

Vince McMahon’s ultimate goal with all of these decisions thus far was toturn professional wrestling into mainstream pop culture entertainment. Vince finally had the opportunity to do just that when Captain Lou Albano had a chance encounter with Cyndi Lauper on an airplane. Lauper was a wrestling fan and Vince wanted to take advantage of that fact with a mutual working relationship. Momentarily, Albano would make a cameo in Lauper’s chart-topping “Girls Just Wanna Have Fun” music video, and Lauper would make subsequent appearances on WWE TV.

This opened the door for WWE to work with MTV and other celebrities. Famously, Mr. T appeared in the main event of the first WrestleMania as Hulk Hogan’s tag team partner, but the list of celebrities who made a cameo in the WWE is long, and includes names such as Andy Warhol.Not only did WWE grow its audience from there, but it helped wrestling become more than just a niche product. In theMr.McMahondocumentary, Wendi Richter says that celebrities co-signing wrestling made it"okay for people to say ‘I watch wrestling.'”

The Goonies with Cyndi Lauper

6Creating WrestleMania

A Revolutionary Concept

Vince McMahon’s biggest gamble in his early years was creating the concept of WrestleMania. Not only was WrestleMania meant to be an expansion of wrestlers collaborating with celebrities on a bigger stage, but in Vince’s aspirations of creating must-see TV,WrestleMania was going to be an annual season finale of the product’s biggest storylines. For the first event, thousands of people were in attendance with millions watching in every major US city on closed-circuit television, and being broadcast in 24 foreign countries.

This was going to be the biggest platform that professional wrestling - not just WWE - was going to showcase itself on. It’s important to mention that Vince did not pull the idea out of a hat. Jim Crockett Promotions, the dominant member of the NWA, had already been promoting a big event broadcast on closed-circuit TV, Starrcade, since 1983. However, as with many other things, Vince simply decided to do it bigger and better.The success of WrestleMania solidified Vince McMahon as the winner of the territory warand consecrated his new brand of pro wrestling as an entertainment spectacle.

WrestleMania 40 WWE

5Creating the Mr. McMahon Character

Changing Wrestling in More Ways Than One

At the time of the Montreal Screwjob, Vince McMahon was still seen onscreen as just a commentator, interviewer, and announcer. Surely the insiders knew he was the Chairman of the Board, but in an era where kayfabe was still protected, this was never really publicly acknowledged. That would change in the aftermath ofthe infamous Montreal Screwjob. After the confusion caused by the finish and title change of Survivor Series’ Bret “The Hitman” Hart vs. Shawn Michaels, Vince decided to come on air for an interview and not deny anything, but rather embrace the accusations.

“Bret screwed Bret”: one short sentence cemented Vince to the public as the bad guy in this equation. Vince would capitalize on this perception by becoming a villain figure in ongoing stories on WWE TV, the archetypical evil, rich boss that he knew most members of his audience had to deal with in real life. While the authority figure angle would quickly become a common trope in pro wrestling, the Mr. McMahon character would prove a perfect foil toStone Cold Steve Austin,being instrumental in Austin’s ascent and ushering in the Attitude Era.

Vince McMahon Raw Is War

What Vince actually did was to give kayfabe a mercy shot. He understood that, by then, audiences were smart enough to know what pro wrestling was, and he had a daily reminder of how well embracing realism and tongue-in-cheek narratives was doing for the rival company, WCW, which had been beating WWE in the ratings for more than a year, at that time. From that moment, nothing was off limits, creating the most successful era (in terms of audience reception and mainstream popularity) in the company’s history.

4Going Public on the Stock Market

A Necessary Choice That Changed the History of Pro Wrestling

In October 1999,WWE became a publicly traded companyunder the name of Wrestling Federation Entertainment Inc. The decision was part of Vince’s plan to secure the resources he needed to fight against WCW and put an end to the Monday Night Wars. It was an outstanding success. The WWE raised substantial capital (the IPO generated 173 million USD) and this was then invested in acquiring talent, fueling creative, and deploying outstanding production values that made WWE a spectacular, must-see TV show.

Since then, the WWE has remained an attractive investment, and it certainly would not be the worldwide entertainment titan that it is today if it didn’t go public in 1999. More than two decades later, WWE was sold to the Endeavor Group for more than 9 billion, merging with the UFC to create a single holding called TKO. When Vince sold his shares in April 2024, on the heels of the Janet Grant lawsuit and his resignation from the company, he made a profit of close to 800 million.

WWF ceremony on Wall Street 1999

3Buying WCW

Gaining a Priceless Library for Basically Nothing

By the early 2000s, WCW was a far cry from being the same juggernaut that almost put WWE out of business in the 90s. Vince McMahon buying out WCW was practically a mercy killing, but it’s a smarter business move than it’s given credit for. It wasn’t so much Vince taking his competition out of the picture, as WCW was already doomed. This purchase was memorable becauseVince acquired the priceless library of the WCW for the ridiculous (for him) amount of 1,7 million USD, on top of the 2,5 million for trademarks and name property.

This meant that the WWE could take the likeness of the NWO, Sting, DDP, Goldberg, etc., and produce merchandise, T-shirts, DVDs, and make money off of that for years to come. This would also give the WWE the footage from the entire history of WCW, going back to the 1980s. It was such a ridiculously good deal that, if Vince had not moved quickly, he would have been beaten by some of the WCW wrestlers who, according to Chris Jericho, were scraping together the necessary money.

Randy Savage in WCW

2Turning the Product PG

A Controversial Decision that Paid Off

Even at the height of the Hulk Hogan and Rock n Wrestling Era, wrestling was never quite a family product. Kids always enjoyed it and it was a fun pastime to spend with the family, but the violent nature never made it purely for children. That violence (along with explicit graphic content) only intensified with the Attitude Era and the following Ruthless Aggression Era. By the time the 2010s rolled around, Vince realized that it was time for WWE togo in a more family-friendly direction.

1The Deal with Saudi Arabia

Controversial, But Made Money

Speaking of business decisions that are still criticized, signing a 10-year deal with the Ministry of Sport to perform annual events in Saudi Arabia is still a point of contention for Western audiences due to the criticism made against the Saudi government for its stance toward LGBTQ+ rights, women, and even for assassinating dissenters. Be that as it may be, it is a business decision thatmade WWE $100 million a year, reportedly a net of $50-55 million for each WWE event held in Saudi Arabia.

Casting WWE in international markets does more to grow WWE’s audiences on a worldwide level as part of a clear strategy that wants to capitalize on markets outside the Western world, including India and China, to make WWE a truly global product. In terms of the Saudi deal, it must be said thatWWEhas tried to work around the country’s policies toward women as an opportunity to break barriers, giving the country the first-ever women’s wrestling matches, and trying to encourage at least a modicum of change. While this was obviously notVince McMahon’s priority when he made the deal, it’s still a positive consequence of one of his best business decisions.

John Cena attempts an Attitude Adjustment on CM Punk at WWE Monday in the Bank 2011