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Inside Serena Williams’ Plan To Ace Venture Investing

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On Serena Williams’ calendar—which is to calendars what Jackson Pollock paintings are to art—Saturdays are designated family time. The Saturday I’m with her in Rome (she was in New York earlier in the week and will be in Paris the following one) carries extra significance. Exactly four years ago, in exactly that Eternal City, she met her husband, Alexis Ohanian, cofounder of online community Reddit. 

The two celebrate, in part, with the kind of outing anyone who’s not the most famous woman athlete in the world takes for granted: a stroll in a hotel garden with their joint venture, 22-month-old Olympia, in tow. It’s more romantic than it sounds: The Rome Cavalieri goes so far as to call its 15-acre garden a “private park,” littered with marble and bronze, lions and unicorns.

The regal surroundings befit a historic figure of American sport, who has 23 Grand Slam titles and has blown away any number of barriers and stereotypes. And the unicorns? Between Reddit and his $500 million fund, Initialized Capital, Ohanian does his part. But it turns out that Williams has quietly been playing that game, too.

She’s now the first athlete ever to hit Forbes’ annual list of the World’s Richest Self-Made Women, with an estimated fortune of $225 million, the vast majority of it having come via her brain and brand rather than her backhand. And over the past five years, she’s been quietly dropping money into 34 startups. In April, Williams formally announced that Serena Ventures is open for business, to fund others and launch companies herself.

Athletes are richer than ever, thanks to the explosion in TV rights fees for live sporting events, which trickle down to players. The 50 highest-paid athletes in the world made $2.6 billion last year, versus $1 billion 15 years ago. And Williams is hardly the first to put newfound disposable income to active work—in the NBA alone, LeBron James, Stephen Curry and Kevin Durant have all launched media companies, and Durant, Andre Iguodala and Carmelo Anthony are active venture capital investors. But she is one of the few specifically gearing investments around a single north star: herself.

“I want to be a part of it,” she says, sitting at the hotel. “I want to be in the infrastructure. I want to be the brand, instead of just being the face.” Given her longtime background in style and design, that means overweighting on fashion lines, jewelry and beauty products. Yes, she’ll keep competing at tennis—her resilient comeback last year after giving birth burnished her as a cultural icon who transcends sports. And sure, she’ll happily continue to rake in easy endorsement money from the likes of Nike and JPMorgan Chase—her $29 million total income over the past 12 months is the highest of her career. 

But like a ground stroke with torque, Williams bets she can eventually dwarf those figures by leveraging some of her own cash with her name and fame.

Serena Williams
Power Game: Williams invested in 34 startups over the past five years. The value of her portfolio has doubled to more than $10 million.ADAM PRETTY/GETTY IMAGES

The story of how sisters Serena and Venus Williams reached the top of the tennis world is the stuff of Hollywood legend: A black father with limited tennis experience homeschools his two daughters and teaches them on the streets of Compton, California, to penetrate and then dominate a lily-white sport. “You’d see different people walking down the street with AK-47s and think, ‘Time to get in the house,’” she remembers of those early years. “When you hear gunshots, you get low.

Their father’s insistence that his precocious daughters avoid the private tennis academy machine and well-oiled junior tournament circuit left a mark on the younger one, especially after she won her first Grand Slam title at age 17. “It really shaped me for the rest of my career both on and off the court in terms of taking a chance and how to be different and how to stand out,” Williams says of his strategy. When everyone zigs, she zags.

So at Serena Ventures, she focuses on companies founded by women and minorities. Yes, there’s a social purpose to that decision. But as with her tennis upbringing, she’s also finding opportunity by avoiding the herd. Just 2.3% of the total venture capitalinvested last year in the U.S. went to women-led startups—and even when including firms with both a male and female founder, you’re just at 10%. The numbers are worse for black and Hispanic founders. Yet some 60% of Williams’ investments so far have gone to companies led by women or people of color. “What better way to preach that message?” asks Williams.

The only way to find enough of those companies right now is to nurture them early, something that Williams got hooked on after investing and losing (eventually) $250,000 in a startup in the years before Serena Ventures. “I learned you can’t overspend, but I also learned that I love seed investing,” she says. Of the 34 companies she’s backed through Serena Ventures, more than three quarters are early-stage. 

“It’s fun to get in there. I don’t gamble. I don’t jump off buildings,” says Williams. “I’m the most non-taking-a-chance kind of a person, but I felt like seed was where we wanted 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. 

Serena 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.”

Serena Williams
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 Serens 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. Picture: LEVON BISS FOR FORBES

Another 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.”

Kurt Badenhausen; Forbes Staff

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The Springboks And The Cup Of Good Hope

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After their epic win beating England at the 2019 Rugby World Cup in Japan on November 2, the Springboks returned home to South Africa, undertaking a nation-wide tour, in an open-top bus, holding high the Webb Ellis Cup. In this image, in the township of Soweto, they pass the iconic Vilakazi Street with throngs of screaming, cheering residents and Springbok fans lining the street. The sport united the racially-divided country. For the third time in history, the South African national rugby team was crowned world champions.

Image by Motlabana Monnakgotla

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Déjà vu: South Africa Back to Winning

Our Publisher reflects on the recent Springbok victory in Yokohoma, Japan

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Rugby World Cup 2019, Final: England v South Africa Mtach viewing at Nelson Mandela Square

By Rakesh Wahi, Publisher
FORBES AFRICA

Rugby is as foreign to me as cricket is to the average American. However, having lived in South Africa for 15 years, there is no way to avoid being pulled into the sport. November 2, 2019, is therefore a date that will be celebrated in South Africa’s sporting posterity. In many ways, it’s déjà vu for South Africans; at a pivotal time in history, on June 24, 1995, the Springboks beat the All Blacks (the national rugby team of New Zealand) in the final of the World Cup. The game united a racially-divided country coming out of apartheid and at the forefront of this victory was none other than President Nelson Mandela or our beloved Madiba. In a very symbolic coincidence, 24 years later, history repeated itself.

South Africans watched with pride as Siya Kolisi lifted the gold trophy in Yokohama, Japan, as had Francois Pienaar done so 24 years ago in Johannesburg. My mind immediately reflected on this extremely opportune event in South Africa’s history.

The last decade has not been easy; the country has slipped into economic doldrums from which there seems to be no clear path ahead. The political transition from the previously corrupt regime has not been easy and it has been disheartening to see a rapid deterioration in the economic condition of the country. The sad reality is that there literally seems to be no apparent light at the end of the tunnel; with blackouts and load-shedding, a currency that is amongst the most volatile in the world, rising unemployment and rising crime amongst many other issues facing the country.

Rakesh Wahi, Publisher Forbes Africa

Something needed to change. There was a need for an event to change this despondent state of mind and the South African rugby team seems to have given a glimmer of hope that could not have come at a more opportune time. As South African flags were flying all over the world on November 2, something clicked to say that there is hope ahead and if people come together under a common mission, they can be the change that they want to see.

Isn’t life all about hope? Nothing defies gravity and just goes up; Newton taught us that everything that goes up will come down. Vicissitudes are a part of life and the true character of people, society or a nation is tested on how they navigate past these curve balls that make us despair. As we head into 2020, it is my sincere prayer that we see a new dawn and a better future in South Africa with renewed vigor and vitality.

Talking about sports and sportsmen, there is another important lesson that we need to take away. Having been a sportsman all my life, I have had a belief that people who have played team sports like cricket, rugby, soccer, hockey etc make great team players and leaders. However, other sports like golf, diving and squash teach you focus. In all cases, the greatest attribute of all is how to reset your mind after adversity. While most of us moved on after amateur sports to find our place in the world, the real sportspeople to watch and learn from are professionals. It is their grit and determination.

My own belief is that one must learn how to detach from a rear view mirror. You cannot ignore what is behind you because that is your history; you must learn from it. Our experiences are unique and so is our history. It must be our greatest teacher. However, that’s where it must end. As humans, we must learn to break the proverbial rear view mirror and stop worrying about the past. You cannot change what is behind you but you can influence and change what is yet to come.

I had the good fortune of playing golf with Chester Williams (former rugby player who was the first person of color to play for the Springboks in the historic win in 1995 and sadly passed away in September 2019) more than once at the SuperSport Celebrity Golf Shootout.

Chester played his golf fearlessly; perhaps the way he led his life. He would drive the ball 300 meters and on occasion went into the woods or in deep rough. Psychologically, as golfers know, this sets you back just looking at a bad lie, an embedded or unplayable ball or a dropped shot in a hazard. For a seasoned golfer, it is not the shot that you have hit but the one that you are about to hit. Chester has a repertoire of recovery shots and always seemed to be in the game even after some wayward moments. There is a profound lesson in all of this. You have to blank your mind from the negativity or sometimes helplessness and bring a can do and positive frame of reference back into your game (and life). Hit that recovery shot well and get back in the game; that’s what champions do.

We need to now focus our attention on the next shot and try and change the future than stay in the past.

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The NBA’s Highest-Paid Players 2019-20: LeBron James Scores Record $92 Million

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NBA salaries have skyrocketed in recent years, but the biggest stars have earned more off the court than on it to this point in their careers. LeBron James, who tops the ranking for the 2019-2020 season, has made more than twice as much from endorsements than his $270 million in playing salary over his first 16 years. Kevin Durant’s on-court earnings of $187 million in 12 seasons is dwarfed by his current ten-year, $275 million Nike deal.

At $92 million, including salary and endorsements, James is the NBA’s highest-paid player for the sixth straight year. It is a record haul for an active basketball player. Nike is his biggest backer, and the company is naming a new research lab at its Beaverton, Oregon, corporate campus after James. Last month, the 17th iteration of his Nike signature shoe, the LeBron XVII, hit stores.

The four-time NBA MVP added a pair of endorsement deals in 2019 with Rimowa luggage and Walmart, which joined Coca-Cola, Beats By Dre, Blaze Pizza and NBA 2K in his sponsorship stable.

He also has a budding digital media company, Uninterrupted, and a production firm, SpringHill Entertainment, which will release a sequel to the 1996 Michael Jordan vehicle Space Jam in conjunction with Warner Bros. in 2021. All of the off-court work is worth an estimated $55 million for James this season.

The Los Angeles Lakers star’s comments about the NBA’s geopolitical mess in China also reveal the precarious position everyone in the league is in as political unrest in Hong Kong shows no signs of abating.

As the league’s 74th regular season tipped off Tuesday night, the NBA was still reeling from the crisis set off by a tweet from Houston Rockets GM Daryl Morey in support of Hong Kong’s pro-democracy protesters.

Commissioner Adam Silver backed Morey’s right to free speech, but some players didn’t, including James, who called Morey “misinformed or not really educated” on the situation. “We love China,” said Rockets point guard James Harden.

It was a rare misstep for two of the league’s more media-savvy stars, both of whom have close ties to China. Adidas, which has Harden as the face of its basketball business, generated more revenue in China last year than in North America, and the Rockets are China’s most popular team after drafting native son Yao Ming in 2002.

Nike’s China revenue topped $6 billion during the last fiscal year, and the country is a growth leader for the brand. James has represented Nike on 15 off-season trips to China. The sports giant pays James more than $30 million annually to pitch its products around the globe.

And the threat of losing its growth trajectory in China could have far-reaching consequences for team valuations.

But back at home, the financials of NBA franchises remain solid, which is good for player salaries. The league’s salary cap is soaring, fueled largely by the nine-year, $24 billion TV deal with ESPN and TNT signed in 2014.

NBA players are entitled to 51% of the league’s “basketball-related income” as laid out in the collective bargaining agreement. The rich TV deal and budding international business means 46 players will earn a playing salary of at least $25 million this season, according to Spotrac. The $25 million club had zero members five years ago. And unlike in the NFL, every dollar is guaranteed upon signing.

The NBA's Highest-Paid Players
The Highest-Paid NBA Players - Dataviz

On-court salaries in the NBA are capped based on a player’s number of years in the league and accolades earned in cases in which an award like MVP entitles them to a bigger percentage of a team’s salary cap.

So the pecking order for the elite stars is ultimately determined by their off-court income, with the shoe deal the biggest component of those earnings. There are ten active NBA players who will make at least $10 million from their shoe contracts this year, by Forbes’ count.

Stephen Curry comes in at No. 2 on the earnings list this year and is expected to generate $85 million this season, including $45 million off the court. Under Armour represents nearly half of his off-court income.

Curry’s $40.2 million salary from the Golden State Warriors is the highest in the history of the NBA; he’s in the third season of the five-year, $201 million contract he signed in 2017. Curry’s production company, Unanimous Media, has a development deal with Sony Pictures.

Unanimous’ first movie, Breakthrough, was released in April, with Curry playing a role in marketing the Christian-oriented film, which grossed $50 million on a $14 million budget.

Durant has the NBA’s second-biggest annual shoe contract after James’ at an estimated $26 million this season. His total earnings from his playing salary and endorsements is $73 million. Nike sells more KD shoes in China than in North America, according to Durant’s business partner Rich Kleiman.

Like James and Curry, Durant has his own production company, which is co-producing a new basketball-themed drama, Swagger, that is inspired by Durant’s youth basketball experience and will air on the Apple TV+ streaming service.

The NBA’s ten highest-paid players are expected to earn a cumulative $600 million this year, including $250 million from endorsements, appearances, merchandise and media.

A Closer Look At The NBA's Highest-Paid Players
#10: Damian Lillard

Lillard signed a four-year, $196 million supermax extension in July with the Portland Trail Blazers that kicks in for the 2021-2022 season. The final year is worth $54.25 million for the 2013 NBA Rookie of the Year and four-time All-Star. Lillard’s Adidas shoe deal is worth roughly $10 million annually.

#9: Giannis Antetokounmpo

The “Greek Freak” is eligible for a five-year, $248 million contract extension next summer with the Milwaukee Bucks. It would be the richest deal in the history of the sport. In June, Nike unveiled the first signature shoe, Zoom Freak 1, for the 2019 NBA MVP.

#8: Chris Paul

Only Curry will earn more on the court this season than Paul, who was traded to the Oklahoma City Thunder in July. Paul was an early investor and ambassador for Beyond Meat, whose stock price has quadrupled since its initial public offering in May.

#7: Klay Thompson

Thompson’s coach, Steve Kerr, says the sharpshooter is likely to miss the entire season after tearing his ACL during the NBA Finals in June. But he’ll still collect his full $32.7 million salary—almost double last year’s—under the first season of the five-year, $190 million pact he signed in July. Thompson is the basketball face of Chinese shoe brand Anta.

#6: Kyrie Irving

Irving joins his third team in four years this season. His four-year deal with the Brooklyn Nets is worth $136 million and includes an additional $4.3 million in potential incentives. A viral Pepsi ad campaign featuring Irving as the elderly Uncle Drew eventually led to a 2018 feature film; Irving has partial ownership of the character. Irving is another Beyond Meat investor.

#5: James Harden

The 2018 NBA MVP purchased a minority stake in the Houston Dynamo of MLS this summer for $15 million. Harden also holds equity stakes in BodyArmor, Stance socks and Art of Sport. His salary with the Rockets jumps $8 million this season with the start of a contract extension he signed in 2017.

#4: Russell Westbrook

Westbrook’s five-year, $207 million contract is the largest deal in the NBA right now. The eight-time All Star extended his deal with Nike’s Jordan brand in 2017 for another ten years and in 2018 received his first signature shoe, the Why Not Zer0. Westbrook has averaged a triple-double for three straight seasons.

#3: Kevin Durant

Durant is likely to miss the entire season recovering from a torn Achilles tendon suffered in June during the NBA Finals. He’ll still pocket his full first-year salary from the Brooklyn Nets under the four-year, $164 million deal he signed in July. He’s invested in more than 30 startups, including Postmates and investing app Acorns.

#2: Stephen Curry

The two-time MVP used some of his hoops money in June to buy a $31 million home in Atherton, California, with his wife, Ayesha. He also made a seven-figure donation this summer to Howard University to help launch a golf program at the school and recently signed an endorsement partnership with Callaway Golf. Curry became the only player to win the NBA MVP unanimously when he won his second of back-to-back awards in 2016.

#1: LeBron James

James signed an endorsement in 2019 with Walmart that is rooted in community work. He worked with the retail giant on its Fight Hunger. Spark Change. initiative, as well as the company’s back-to-school campaign. James is part of an investment group that owns 19 Blaze Pizza franchises across Illinois and Florida.

-Forbes; Kurt Badenhausen

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