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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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30 under 30

Applications Open for FORBES AFRICA 30 Under 30 class of 2020

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FORBES AFRICA is on the hunt for Africans under the age of 30, who are building brands, creating jobs and transforming the continent, to join our Under 30 community for 2020.


JOHANNESBURG, 07 January 2020: Attention entrepreneurs, creatives, sport stars and technology geeks — the 2020 FORBES AFRICA Under 30 nominations are now officially open.

The FORBES AFRICA 30 Under 30 list is the most-anticipated list of game-changers on the continent and this year, we are on the hunt for 30 of Africa’s brightest achievers under the age of 30 spanning these categories: Business, Technology, Creatives and Sport.

Each year, FORBES AFRICA looks for resilient self-starters, innovators, entrepreneurs and disruptors who have the acumen to stay the course in their chosen field, come what may.

Past honorees include Sho Madjozi, Bruce Diale, Karabo Poppy, Kwesta, Nomzamo Mbatha, Burna Boy, Nthabiseng Mosia, Busi Mkhumbuzi Pooe, Henrich Akomolafe, Davido, Yemi Alade, Vere Shaba, Nasty C and WizKid.

What’s different this year is that we have whittled down the list to just 30 finalists, making the competition stiff and the vetting process even more rigorous. 

Says FORBES AFRICA’s Managing Editor, Renuka Methil: “The start of a new decade means the unraveling of fresh talent on the African continent. I can’t wait to see the potential billionaires who will land up on our desks. Our coveted sixth annual Under 30 list will herald some of the decade’s biggest names in business and life.”

If you think you have what it takes to be on this year’s list or know an entrepreneur, creative, technology entrepreneur or sports star under 30 with a proven track-record on the continent – introduce them to FORBES AFRICA by applying or submitting your nomination.

NOMINATIONS AND APPLICATIONS CRITERIA:

Business and Technology categories

  1. Must be an entrepreneur/founder aged 29 or younger on 31 March 2020
  2. Should have a legitimate REGISTERED business on the continent
  3. Business/businesses should be two years or older
  4. Nominees must have risked own money and have a social impact
  5. Must be profit generating
  6. Must employ people in Africa
  7. All applications must be in English
  8. Should be available and prepared to participate in the Under 30 Meet-Up

Sports category

  1. Must be a sports person aged 29 or younger on 31 March 2020
  2. Must be representing an African team
  3. Should have a proven track record of no less than two years
  4. Should be making significant earnings
  5. Should have some endorsement deals
  6. Entrepreneurship and social impact is a plus
  7. All applications must be in English
  8. Should be available and prepared to participate in the Under 30 Meet-Up

Creatives category

  1. Must be a creative aged 29 or younger on 31 March 2020
  2. Must be from or based in Africa
  3. Should be making significant earnings
  4. Should have a proven creative record of no less than two years
  5. Must have social influence
  6. Entrepreneurship and social impact is a plus
  7. All applications must be in English
  8. Should be available and prepared to participate in the Under 30 Meet-Up

Your entry should include:

  • Country
  • Full Names
  • Company name/Team you are applying with
  • A short motivation on why you should be on the list
  • A short profile on self and company
  • Links to published material / news clippings about nominee
  • All social media handles
  • Contact information
  • High-res images of yourself

Applications and nominations must be sent via email to FORBES AFRICA journalist and curator of the list, Karen Mwendera, on [email protected]

Nominations close on 3 February 2020.

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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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