While Serena Williams plays her best games at the US Open, this is how she builds her investment off the field.

Only Serena Williams, a 23-time Grand Slam champion, can attract the combination of ambitious names that showed up at Arthur Ashe Stadium in Flushing Meadows to see her performance at the US Open on Monday night: Mike Tyson sitting next to Martina Navratilova. Bill Clinton. Dr. Pity.

The wonderful tennis player Billie Jean King paid tribute to Williams after the attack (in which Williams beat Danka Kovinic of Montenegro in two sets, 6-3, 6-3), recalling how she met Williams and her sister Venus in April 1988 at a tennis clinic for 1,200 children, when Serena was six and Venus seven, and how, even then, Serena’s service stood out. “I said, ‘Don’t replace anything. ‘”

In 2019, the year Williams became the first athlete to make Forbes’ annual list of America’s richest self-taught women, Forbes interviewed Williams about her plans as an investor and featured her in a magazine article. He had already bet on 34 startups, focusing on corporations created through women and minorities. In March of this year, his venture capital firm, Serena Ventures, said it had raised $111 million from investors, with a portfolio of 60 corporations, according to the New York Times, adding MasterClass and frozen food service Fitness DailyHarvest. Five months later, in a Vogue canopy article, Williams, 40, announced she would retire from tennis after betting on the US Open. That same month, Serena Ventures invested in intellectual fitness startup Wondermind, co-founded through singer and actress Selena Gomez, Mandy Teefey and newsletter entrepreneur Daniella Pierson. Williams appeared on the Forbes 2022 list of America’s richest self-taught women in June, estimated at $260 million.

At her tribute Monday night, Billie Jean King called on Williams’ efforts to use her fame and call to make a difference. “Thank you for your leadership and commitment to diversity, equity and inclusion, especially for women and women of color,” King said. he said, to the applause of the sold-out crowd. “Thank you for sharing it with all of us. We love you. God bless you. And guess what? They are just getting started.

Here is the June 3, 2019 Forbes article about Serena Williams, republished in its entirety.

In Serena Williams’ calendar, which is to calendars what Jackson Pollock’s paintings are to art, Saturday is referred to as a family circle moment. Saturday I am with her in Rome (she in New York last week and will be in Paris the next) has an additional meaning. Exactly 4 years ago, precisely in this eternal city, she met her husband, Alexis Ohanian, co-founder of the online community Reddit.

Both celebrate, in part, the kind of outing that any outstanding female athlete in the world takes for granted: a walk on a hotel lawn with their joint venture, Olympia, 22 months in tow. Sounds: The Rome Cavalieri goes so far as to call its 15-acre lawn a “private park,” filled with marble and bronze, lions and unicorns.

The real scenario fits an ancient figure in American sport, who has 23 Grand Slam titles and has broken down many barriers and stereotypes. What about unicorns? Between Reddit and its $500 million fund, Initialized Capital, Ohanian is doing its part. But it turns out that Williams also quietly played this game. She is now the first athlete to make Forbes’ annual list of america’s richest self-taught women, with an estimated fortune of $225 million, the vast majority coming from her brain and logo than from her upside down. And over the past five years, it has quietly invested cash in 34 startups. In April, Williams officially announced that Serena Ventures was open for business, to fund others and free up businesses themselves.

Athletes are richer than ever, thanks to the explosion of TV rights fees for live sporting events, which are trickling down to players. the first to put a new available source of income to painting: in the NBA alone, LeBron James, Stephen Curry and Kevin Durant have introduced media companies, and Durant, Andre Iguodala and Carmelo Anthony are active venture capitalists. But she’s one of the few to target investments in particular around a single north star: herself.

“I need to be a component of that,” she says, sitting in the hotel. I need to be in the infrastructure. I need to be the brand, just be the face. Given its long-standing delight in taste and design, this means an obesity in fashion lines, jewelry and attractive products. Yes, she will continue to compete in tennis – her resilient comeback last year after giving birth made her a cultural icon that transcends sport. And of course, he will gladly continue to raise cash smoothly thanks to Nike and JPMorgan Chase, his overall revenue stream of $29 million over the past 12 months is the highest of his career.

But like a floorstroke with torque, Williams bets he can eclipse unit numbers by tapping into his own cash with his call and fame.

Power play: Williams has invested in 34 startups over the past five years. The value of its portfolio has doubled to more than $10 million.

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The story of how sisters Serena and Venus Williams rose to the top of world tennis is the stuff of Hollywood legend: a black father with limited tennis experience teaches his two daughters at home and teaches them on the streets of Compton, California, to penetrate and then master a white set of lilies. “You’d see other people walking down the street with AK-47s and thinking, ‘It’s time to get into the house,'” he recalls in his early years. “When you hear gunshots, you diminish yourself. “

Her father’s insistence that his precocious daughters, the device of the personal tennis academy and the well-oiled youth tournament circuit, left a mark on the younger one, especially after she won her first Grand Slam name at age 17. My career on and off the court in terms of taking risks and how to be another and how to excel,” Williams says of his strategy. When everyone zigzags, she zagza.

At Serena Ventures, she focuses on corporations founded by women and minorities. Yes, there is a social goal to this decision. But as with his tennis education, he also discovers opportunities by avoiding the herd. Only 2. 3% of the total venture capital invested last year in the U. S. UU. se targeted female-led startups, and even added corporations with a male and female founder, by only 10%. The numbers are worse for black and Hispanic founders. Still, about 60 percent of Williams’ investments went to businesses run by women or other people of color. “What better way to pontificate this message?” Williams asks.

The only way to locate enough of those corporations right now is to nurture them early, which Williams has become addicted to after making an investment and wasting (possibly) $250,000 on a startup in the years leading up to Serena Ventures. “I’ve learned that you can’t spend too much, but I’ve also learned that I like to invest in seed capital,” he says. Of the 34 corporations it has supported through Serena Ventures, more than three-quarters are in the start-up phase.

“It’s fun to go in. I don’t play. I don’t jump out of buildings,” Williams says. “I’m the kind of user who doesn’t take risks, but I felt like the seed we were looking for. “to be – to be. “

Given the exponential riskiness involved in pre- and early-revenue companies, Williams has built a team of Silicon Valley mentors around her, much as Patrick Mouratoglou has guided Williams on the court and WME’s Jill Smoller has handled her endorsements—almost a quarter-billion worth—for nearly two decades. There’s Chris Lyons, from Andreessen Horowitz, who is an informal advisor and friend. “She is more passionate than 99% of the people in this space,” says Lyons. “She’s reaching out to me regularly asking what we think of companies.”

There’s Facebook chief operating officer Sheryl Sandberg, a longtime friend, with whom she serves on the board of SurveyMonkey. “I always ask her advice in a lot of different areas,” Williams says. (The tennis star is also on the board of the social shopping platform Poshmark.)

But one mentor stands above the rest—the one she married. “I’ve been really leaning on Alexis,” she says. Williams had never heard of Reddit when the pair met in 2015 and Ohanian knew little about tennis. But they bonded over ambition. “She is determined to be great at everything she does,” says Ohanian, who Forbes estimates is worth $70 million on his own.

His venture firm’s targets are traditionally more tech-focused—big scores include Instacart and Patreon. But in living through Ohanian’s deals, Williams has learned. Initialized and Serena Ventures have even co-invested on a few, including Gobble, which does weekly dinner-kit deliveries, and Wave, which offers no-fee transfers on money sent to Africa by phone. “I’d like to call us a more modern business family,” says Williams.

The rate of Williams’ investments has ramped up in lockstep with the onboarding of a portfolio manager. Alison Rapaport, 29, was fresh out of Harvard Business School with an M.B.A. after a five-year stint in JPMorgan’s asset-management group, when she got connected with Williams through Andreessen’s Lyons. Williams told Rapaport to come to the interview with three investment ideas, along with the numbers and rationale behind them. Rapaport did her homework on the investment ideas—and diligence on her potential new boss, who earlier in the week posted on Instagram how much she liked Taco Sunday. Rapaport arrived at Williams’ home outside San Francisco for a Sunday meeting at noon armed with investment ideas and two bags of takeout, make-your-own tacos, and she handled Ohanian’s rapid-fire follow-up emails with aplomb. “I knew this was our girl,” Williams says.

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erena Williams slides around the red clay of the Tennis Club Parioli in Rome a few days ahead of the Italian Open, practicing to an eclectic mix of musical genres whose only commonality is that they’re sung by powerful women, from Rihanna to Adele to Pink. As word spreads around the club that the world’s most famous tennis player is hitting balls in their midst, a crowd predictably gathers, the youngest among them squealing, “Serena!”, the oldest snapping and sharing pictures.

Williams is by far the most famous female athlete in the U.S.—and only Tom Brady and Tiger Woods finish a tick ahead among all athletes in terms of public awareness. And that fame carries almost no brand downside—her appeal rates above average across all demographics, from Millennials to blue collar to high income, says Henry Schafer, who tracks Q Scores, which measure the likeability of a celebrity.

After 20 years in the spotlight, Williams knows how to handle the star power. At the end of the two-hour session, she gracefully obliges several with autographs and selfies. But more important: She has figured out at Serena Ventures how to harness it.

The past decade has given rise to the celebrity VC investor, spurred by the success of people like the actor Ashton Kutcher and the musician Nas, who both have their own funds. The recent IPOs for Uber and Lyft included scores of musicians and Hollywood A-listers like Gwyneth Paltrow, Jay-Z and Olivia Munn, who got in early and cashed in big. Overall, Ohanian is skeptical of the trend. “The advice I generally give to founders is don’t take money from celebrities,” he says. “The only exception is when they are really going to add value. Because in most cases, they are not really familiar with this world and if you are doing it to feed your ego, it’s a bad idea.”

So Williams tries to put money in deals where her fame and brand and platform grow the pie. As one of the better product endorsers of this century, it’s something she’s honed in ways that most musicians and actors (who turn up their noses at most product deals) have not. She counts nearly 30 million followers across social media—her posts of herself wearing Nike’s swoosh generated more than $2 million in promotional value for the brand over the past 12 months, according to Hookit, which tracks celebrity influence on social media. “Serena is a once-in-a-generation voice, reaching a global audience that extends well beyond tennis,” says Hookit CEO Scott Tilton.

And that voice is amplified exponentially when dealing with an early-stage brand, rather than one like Nike. She shared a pair of videos in an Instagram story of her entourage eating Daily Harvest meals ahead of her hosting duties for the Met Gala. She collaborated with Neighborhood Goods, which brings a pop-up approach to retailing, for her clothing line. “Using her platform to talk about our mission was the biggest support we’ve had besides her capital,” says Georgina Gooley, cofounder of Billie, which makes razors priced to eliminate the “pink tax” that makes female-targeted products cost more than similar versions for men.

The dating and networking app Bumble added Williams as an endorser for 2019, including a Super Bowl ad. The pair also partnered in a pitch competition in which two winners with female founders were chosen for funding from Serena and Bumble. Three executives of companies in the Serena Ventures portfolio—Daily Harvest, the woman-centric co-working space The Wing, and Lola, a natural tampon brand—networked at the first-ever Bumble Fund Summit in April. “She is facilitating a place for people to connect with one another,” says Jordana Kier, Lola’s founder.

That kind of investor-as-rainmaker power translates into another benefit: deal flow. For more mature deals, traditional venture firms need to take large ownership stakes to hit return targets. Williams, though, is happy to ride along. “Firms know Serena is a hugely valuable strategic investor,” says Ohanian. “I think it is the best of all opportunities, and she can essentially cherry-pick from the top VC firms on deals that are interesting that come her way and at the same time she still has her own deal flow from folks who want her to invest.”

Change Agent: “A lot of people say what I do on the court is amazing, but I feel like that’s just the beginning,” says Williams. “I want to be remembered for things I do off the court; lives I’ve been able to impact and voices that have been heard through mine.”

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nother benefit of early-stage investing: Even with 34 checks written, she has still sunk only an estimated $6 million into these companies. As venture investing goes, given her net worth, it’s still low-risk stuff. And the returns so far seem promising; Serena Ventures says they currently value the portfolio at more than $10 million and double the initial investment. Nearly half of the companies have had follow-up rounds of venture investment since Williams invested, and Serena Ventures even seems poised to score its first exit after Unilever announced plans to buy supplement firm Olly Nutrition in April. Five of her investments are up at least fivefold. Top performers include Billie, Daily Harvest, MasterClass and The Wing.

But Serena Williams wouldn’t be one of the all-time great competitors without also needing to invest more in herself. While she’s known as a fashion icon, she has cashed in only via others’ platforms, whether through endorsements or partnerships. Now that’s changing. Smoller, her longtime endorsement agent, recalls a recent meeting at Nike. “I was talking, and Serena interrupted me and started asking all these questions about their distribution channels, KPIs and growth strategies,” he says. “I looked around and saw their faces. . . . She’s at a level where she wants to understand the process and methods, which I think a lot of people don’t expect.” In May last year, Serena Ventures launched a self-funded, direct-to-consumer clothing line, S by Serena. She kept waiting for someone to fund a company for her to design clothing, she says, but “I was thinking of this the wrong way. I had to invest in myself.”

The line includes dresses, jackets, tops, denim and more, mostly priced under $200. She’s excited about an S by Serena show for New York Fashion Week in September. The line got a boost in October when Williams’ close friend Meghan Markle was spotted wearing the collection’s “Boss” blazer, which quickly sold out on the website. Williams returned the favor when she hosted a baby shower for the Duchess of Sussex in February. Williams plans to launch an S by Serena jewelry line this year and one of beauty products in 2020.

With all this commerce, Williams says she’ll continue to abbreviate her on-the-court schedule, prioritizing the Grand Slam events that burnish her brand. While a dinosaur in the tennis world at 37, she still figures she has two or maybe even three years left. “I am in no rush to get out of this sport,” she says. But in Serena Ventures, she’s laid the foundation to keep playing the game her entire life. “I want to create a brand that has longevity, kind of like my career,” she says. “It’s not fancy, it’s not here, it’s not out, it’s not trendy, it’s a staple, like my tennis game.”

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