Jabeur to Evolve, Rublev and Svitolina to Kosmos: The behind-the-scenes shuffles making headlines before AO

With the news of Serena Williams’ impending retirement and her farewell set for the US Open in a few weeks, the biggest question we’re asking is what’s next for one of the world’s greatest athletes? Thanks to a lot of careful planning—and some incredibly keen foresight—the answer to that question holds an endless list of possibilities. As it turns out, Serena has been preparing for life after tennis since before she even lifted her first Grand Slam trophy.

Signs that Serena was going to become a major force in the tennis world were already starting to show even back in 1997, when the 16-year-old inked her first major endorsement deal with Puma.

Richard Williams, her father and longtime coach, was leading the negotiations for the Williamses. Even though she was ranked No. 99 in the world and had only won one pro tournament at the time, Richard made sure that the contract factored in performance bonuses for when Serena eventually became a Top 10 player.

Serena signed her first major endorsement deal with Puma in 1997.

Antonio Bertone, who was then the global director of brand management at Puma, recalled the nearly 12-hour meeting between Richard, teenage Serena and Arnon Milchan, who was then the head of Puma’s principal shareholder, Regency, in an interview with The Undefeated:

“Arnon recognized Serena and Venus’ ability to change the sport of tennis,” Bertone said.

“Puma wasn’t in tennis then. But Arnon went from 0 to 100… like, ‘We’re totally getting back into tennis with Serena.’”

Serena’s obvious game-changing talent, combined with Richard’s complete faith in his daughters’ abilities, set in motion what would become a global marketing juggernaut as both Serena and big sister Venus would go on to conquer the tennis world.

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Long before Serena (left) climbed up the rankings, Richard Williams made sure his daughter's Puma contract included performance bonuses for when she reached the Top 10.

Fast forward five years, and here’s what Serena’s endorsement portfolio looked like around 2002, according to ESPN and the Los Angeles Times:

Puma (shoes, apparel) - $2.5 million+
Avon (cosmetics) - $1 million+
Wrigley (chewing gum) - $1.1 million+
McDonald's (fast food) - $1 million+
Unilever Close-Up (toothpaste) - $500,000+

Those already impressive figures would only continue to grow, along with Serena’s trophy count—by 2002, she had already reached the WTA world No. 1 ranking, claimed an Olympic gold medal in doubles with Venus, and won five Grand Slam titles in singles. When her contract was up, Puma would eventually lose out in a bidding war to Nike, catapulting Serena into another marketing stratosphere.

Serena’s corporate partnerships are now a double digit who’s who list of blue-chip brands, including her biggest sponsor: Nike.

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By 2000, Richard was no longer having to negotiate on his daughter’s behalf: Serena was represented by agent Jill Smoller, following her from IMG to William Morris Agency and then back to WME-IMG when those two merged.

Now, Serena’s corporate partnerships are a double digit who’s who list of blue-chip brands. As of June 2022, here are some of the names she’s associated with, according to Forbes and Sports Business Journal:

AbbVie (biotech)
Anheuser-Busch InBev (beverage)
Aston Martin (automobile)
Audemars Piguet (luxury timepieces)
Beats by Dre (headphones)
Block Inc (financial services)
DIRECTV, Inc. (cable, television)
Ford Motors - Lincoln (automobile)
Gatorade - Pepsi (beverage)
Gucci (luxury fashion)
Hanes (clothing)
Nike (shoes, apparel)
Subway (fast food)
Tonal (fitness startup)
Wilson Sporting Goods (racquets, tennis equipment)

In 2016, Serena became the world's highest paid female athlete, earning almost $29 million in a single year. But even at the height of her powers, Serena has always operated with the understanding that an athlete’s lifespan is short and unpredictable.

In 2016, Serena became the world's highest paid female athlete, earning almost $29 million in a single year.

The former No. 1 has been just as keen of an investor and entrepreneur as she has been content to endorse a brand. And in true Serena style, she’s diversified her portfolio to follow her personal interests in areas including fashion, technology, venture capital and entrepreneurship.

In 2014, she launched Serena Ventures to invest in companies with diverse founders, and in 2018 she launched S by Serena as her exclusive clothing line. To date, Serena has invested in more than 60 startups through SV, which announced earlier this year that it had raised $111 million in an inaugural fund.

The 40-year-old also has a hand in shaping how companies operate, serving on the board of Survey Monkey’s parent company Momentive. Serena is also a minority owner in the NFL’s Miami Dolphins and NWSL club Angel City FC, and has a stake in UFC, too.

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Serena’s record $94.6 million in career prize money is more than double the WTA Tour’s second-highest earner: big sister Venus with $42.3 million.

With so many dollar signs surrounding her off the court, Serena’s own record $94.6 million in career prize money can almost feel like an afterthought. Throughout her Hall of Fame career, she has racked up more than double the WTA Tour’s second-highest earner, Venus’ $42.3 million.

Serena has spent decades dominating the game and grinding on the practice courts, fighting back from injuries and setbacks, mounting comeback after improbable comeback, climbing to the highest echelons in women’s tennis, in order to amass that record prize money figure.

Now, thanks to her (and her team’s) keen foresight and savvy investing, she’s putting it all to good use in retirement. Serena will walk away from the sport as the greatest of all time, and with an estimated $260 million net worth—putting her among America’s richest self-made women.