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To Learn the Secrets of Long-Term Success Just Study This 50-Year-Long Wrestling Career The astounding popularity of Ric Flair is a textbook study in how to build and maintain a brand.

By Tanner Simkins Edited by Dan Bova

Opinions expressed by Entrepreneur contributors are their own.

Aaron Davidson | Getty Images

Ric Flair is widely considered to be one of the best professional wrestlers of all time. Flair's iconic "WOOO!" mantra, opulent wardrobe and flashy personna laid the fundamentals on how to create a celebrity-wrestling character. In the 1980s's, Flair led the way on building big personalities and bigger storylines; now this is the core of pro wrestling's financial success.

The WWE has a $1.6 billion market value, over 750 million social media followers, other massive media numbers and has legendary personalities like Ric Flair to thank. The "Rolex-wearing, diamond-ring-wearing, kiss-stealing, wheeling-dealing, limousine-riding, jet-flying son of a gun" (as he frequently described himself during his career) is now close to 70-years old with no sign of slowing down. His career spans five decades, includes 16 World Heavyweight Championships and a Hall of Fame induction. He continues to entertain, leaving a lasting impact on pop culture.

Flair, largely by social media, has made a remarkable popularity resurgence in recent years. He is routinely inspiring NFL locker rooms. LeBron James had Nike design shoes after him. Snoop Dogg called Flair the "creator of swag" and he has been used by NCAA D1 athletic programs to recruit athlete prospects. Migos' Offset wears a $70,000 chain made in the image of Ric Flair. There are countless other examples of his extravagant style and personality being embraced by both the music industry and professional athletes. Every social media post, every mention, every interview, adds to his internet celebrity. He monetizes this through his booming retail business at

Whether being the namesake of chart-topping hip-hop songs, having NFL athletes wear his image and quotes on their gameday cleats, or his consistent presence on your social media timeline due to his viral and larger-than-life posts; Ric Flair has leveraged his 1980's over the top antics to not only remain iconic but to make money on the way. That is a skill any entrepreneur would be thrilled to add to their arsenal - here are some lessons for entrepreneurs and small business owners from Flair's pop culture renaissance:

Related: Leadership Lessons From Sports Legends

Keep your pivot foot strong.

Wrestling is all about who ends up with the most points, Flair is always keeping score and trying to win. Entrepreneurs often fail, but the best learn from failure and pivot in the right direction. Flair's career has taken many turns, ups and down, but he seems to land right on his feet each time. Following Flair's 1975 plane crash, he worked hard to recover from spine injuries and opted to abandon his rough, physical style for a more cerebral, submission-based type of wrestling. While most would quit after such an accident, Flair stayed resilient and recovered by taking on a new technique. Entrepreneurs should be willing to do the same when faced with career roadblocks.

Fast forward 40 years and his brand bigger than ever. "The greatest thing I've ever did, was all the things I thought up," Flair said in a statment. "The limousine riding, jet-flying, the kiss-stealing, wheeling dealing…all that. Who would have thought it would all come back?" We caught up with Cameron Fordham of Get Engaged Media, who leads Flair's digital team, to learn how the "Nature Boy' was indeed able to bring back his excess style to extend beyond wrestling. Fordham told me simply, "Flair is a natural entrepreneur that understands the value of the dollar...he is a genuine relatable guy that a lot of his peers tend to gravitate towards."

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Learn from the best.

Wrestlers, like entrepreneurs, should practice mirroring every move of an opponent while anticipating their future move. There is no better way to know your allies and competitors alike than to get close to them. According to Fordham, Flair's "strong personal network of celebrity and sports relationships" is what keeps the wrestling Hall of Famer's digital brand strong amidst changing competitive sets and marketplace conditions.

Ric Flair mirrored his heroes like Muhammad Ali and the original "Nature Boy', Buddy Rogers to create his character. He reflected the "flair" of Ali with the talent of Rogers. For decades he cemented his invented personality with sequin robes and countless other high flash items. He achieved the consumer's top-of-mind awareness needed to launch his very successful ecommerce business and attract nearly two million combined Twitter and Instagram following. He is a must-follow for any entrepreneur.

Related: What Entrepreneurs Can Learn From 6 Country Music Icons

Escape pitfalls

Flair has escaped many head and leg locks, survived a lightning strike (and that plane crash) and, most recently, a near-death health scare related to his heart, but perhaps his greatest escape comes in the form of monetizing over and over again. "My eyes are open to the contemporary world which has brought new ideas and opportunities [to me]," Flair said in our exclusive interview. He believes staying on his feet is just not enough. It is all about moving forward and gaining traction in this new digital space.

Late in 2017, Ric Flair was featured on ESPN's 30 for 30 series. Flair's episode ranked #1 among cable originals for the night. As an ironic comparison, Smackdown (which Flair used to be a part of) aired on the same night but failed to yield as high ratings as the ESPN special did. Snoop Dogg said in the 30 for 30, "[growing up] We wanted to be Ric Flair; we wanted to be flamboyant and the "kiss-stealin, wheelin-and-dealin,' we wanted to be all of that. He was a part of our culture and our life. That's why we love him and we cherish him."

Related: Why Wrestlers Make the Best Entrepreneurs

Stay youthful

Over the course of his career, Flair wrestled in five leagues (WWE, nWo, WWF, WCW, NWA) in order to stay in the game. But Fordham believes Flair's non-wrestling methods of staying hip has been the basis for his longevity. "He has such a vibrant presence that him staying popular is just natural," Fordham told me. "With or without social media, Ric Flair has been and will always be a legend and an icon. But social media takes Ric to astounding new heights in terms of popularity and engagement. Just like anything, social media and going viral allows for more eyes and more people all over the world to engage and follow the Nature Boy… Ric's own legacy creates the buzz and the attention."

Over the years Flair's platforms have changed from the wrestling ring, to the several books he has co-authored, to his celebrity relationships, then to digital media. Ric Flair's personality has continued to grow by being authentic. His original fans stay close and he attracts millennials as new fans from across the globe. It only helps that, according to Fordham, "Flair has really taken to the new age music and the digital stratosphere which fills him with fresh energy."

Like Flair, early stage companies and entrepreneurs can stay youthful by monitoring industry developments, reacting accordingly, and leveraging assets to keep awareness high regardless of platform.

With his popularity at an all time high, Ric Flair has found the fountain of success. By leaning on his larger than life persona to go viral on social media or by being embraced by culture tastemakers like rappers and athletes, "the Rolex wearing, diamond ring wearing, kiss stealing, wheeling dealing, limousine riding, jet flying, son of a gun" will continue to be as culturally relevant as he was over 40 years ago. And entrepreneurs should "WOOO!" along with him for the business lessons you can takeaway from his career.

Tanner Simkins

Founder and CEO of Complete SET Agency

Simkins is founder and CEO of Complete SET Agency, a full-service sports entertainment firm that works with multinational brands, athlete entertainers and accredited investors. Simkins holds degrees from the University of Miami and Columbia University. 

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