What Made This Tennis Champion Become an Entrepreneur? Her Dad's Cassette Collection

Venus Williams isn't lacking for trophies. But she's now focusing on making her sportswear label a global brand. Venus the entrepreneur, like the tennis player, works hard, recovers from mistakes -- and remains a relentless competitor.

 

She climbs gracefully down the warehouse ladder, and then carefully places items in the shipping box. Like every diligent warehouse worker, she double-checks the packing list -- and then takes a moment to hand-write "Packed by Venus" on a small card. Nice touch.

What she didn't write was "Packed by Venus Williams, seven-time Grand Slam singles champion and three-time world No. 1." That might be a little unnerving to the amateur tennis player on the receiving end of Venus's warehouse serve. How does someone fit into that outfit? Williams doesn't have to fulfill orders any more than Michael Jordan, majority owner of the Charlotte Hornets, has to pass out towels on the bench. But like other successful entrepreneurs who love to work not just on their businesses but also in their businesses, she wants to understand her company from every level.

"I always dreamed of being an entrepreneur," she says. "That was one of my lifelong goals."

Wimbledon champion, check. U.S. Open champion, check. Olympic gold medalist, check, check, check, check. Business owner, check again.

Williams is the founder, CEO, and now sole proprietor of EleVen by Venus, a company that makes women's tennis togs; performance clothing for yoga, fitness, running, and dance; and casual gear known as athleisure wear. After struggling to reestablish her brand, not to mention her health, following a couple of setbacks, she's now in full control. Sales tripled last year, according to EleVen, and could quintuple this year as she expands distribution and takes the brand international. She's also the founder of V-Starr Interiors, a seven-employee design firm with clients ranging from luxury residential properties to tennis clubs to hotels. Sometimes the two cross over: The Midtown Athletic Club chain carries the EleVen line in its boutiques and has also hired V-Starr to design lounge and hotel suite renovations for its flagship facility in Chicago.

Venus by the numbers

$34.4 million

Career tennis earnings

71

WTA Tour titles won

17

World singles ranking as of December 2016

2

Companies started

Behind her are bankrupt retailers, a soured manufacturing partnership, and some rookie mistakes. Ahead of her is a venture she hopes will take her far beyond athletic and athleisure apparel to more of a lifestyle brand, one that's about performance and empowerment. "Eleven is better than a 10," she says, by way of explaining her brand message. "It's about reaching your best, pushing beyond the limits, and coming to win. Even if you don't get there, it's about that journey." That's not insignificant from a women who has lost multiple Grand Slam finals to her little sister Serena, among others. This is her connection to women who may not labor under the spotlight but compete nonetheless. "Once you tell that story," she says, "you can see the light bulbs going on."

Being a full-bore entrepreneur would be difficult enough for a retired athlete trying to make a life and career transition, but Williams is doing it while maintaining a full schedule on the WTA Tour. As of December, she was ranked 17th. And, at 36, she is a veritable antique in a sport in which players often peak in their early to mid-20s. It's multitasking on an entirely different level, although she doesn't necessarily see it that way. "When you're an athlete, you're 'done' early in life," she says, "so I decided to see that not as a limitation but an opportunity. I've always been focused on having goals beyond tennis."

Lots of athletes and music and entertainment figures have used their celebrity as a bridge to business. Baseball great Ty Cobb was an early investor in Coca-Cola. In 1941, jazz musician Les Paul created one of the first solid-body electric guitars, and bandleader Fred Waring backed the development of the blender that would bear his name. Golf legend Arnold Palmer proved an ace businessman, auto racer Roger Penske was even better at selling cars than driving them, and boxer George Foreman wasn't too punch-drunk to offload his grill gadget for $137 million. More recently, actress Jessica Alba launched the Honest brand of household products, and actor Ashton Kutcher invested in everything else, or so it would seem. Athletes and entertainers such as Bode Miller, Pharrell Williams, and Sofía Vergara are in various stages of entrepreneurship. And nearly every hip-hop artist is also an aspiring entrepreneur, trying to become the next Jay Z. Yet the scorecard on celebrities and jocks as business people isn't all that pretty. They've been victims of bad advice, if not outright fraud. They've also been susceptible to the delusion that name recognition alone will lead to success. Thousands of celebrity-themed restaurants have died that way, from Joe Louis's to Mickey Mantle's.

“All my Olympic dresses are patterned after Wonder Woman,” says Williams, seen here playing at Rio 2016. “When I go out there, that’s how I want to feel. I want to feel like I can do anything.” Empowerment is one of her brand themes.

CREDIT: Julian Finney/Getty

For Williams, EleVen isn't a short-term play designed with a payday and an exit in mind, a perspective that influences decisions about individual designs and overall collections. "If you want to grow, you have to hit a lot of home runs," she says, "but you have to know your strengths. In fashion, you have core pieces everyone wants every season; no matter how many years you carry them in your line, people look for them. Yet we also change our collection every season, and that's important too. But our path to success is knowing who we are and always staying true to that."

She wears EleVen designs, and she often debuts them; they are then available at retail. Her collections are intended to look great and send a positive message: For example, her Olympic dresses were inspired by the comic book character Wonder Woman. "When I go out there, that's how I want to feel," she says. "I want to feel like I can do anything, like I can make anything happen."

"On the tennis court, it's just me. I'm very hard on myself, because I have to get the whole job done. In business, I'm not as hard on myself or the team. In tennis, I believe in one winner. That's the great thing about business. There isn't just one winner. There's room for everyone to win. I love that."

As a tennis star, Williams has long been acquainted with the business world through endorsements and racket contracts. Yet how many pro tennis players, at the peak of their career and earning power (she's won more than $34 million in prize money), take the time to earn a college degree to plan for the future? She has a degree in business administration from Indiana University East and is now working on her master's in interior architecture. "In our home, we weren't allowed to be just athletes," she says. "We had to be students." The curriculum included business. "Our dad taught us to be entrepreneurs. We would drive to a tournament somewhere, and he would put in a cassette about buying foreclosure properties," she explains. "Serena was 8 and I was 9 years old, and we had to listen to how to make money on foreclosures. Obviously, we didn't understand much of it. That didn't really matter, because our dad was trying to establish that mindset of multitasking, of being an entrepreneur, of charting your own path."

It was a path that was charted even before she was born. Her father, Richard Williams, an entrepreneur in his own right, was watching the 1978 French Open and was astounded to hear that one of the players had just cleared $30,000 for a week's work. The Williams family lived in Compton, California, a gritty Los Angeles satellite far removed from the suburban (read: white) world of tennis. But Compton had public tennis courts. Richard thought, "Why not my kids?" He created a 78-page plan for how his daughters would become champions. Richard and his wife, Oracene Price -- then a nurse -- started teaching Venus, Serena, and three of their half-sisters how to play. (The couple later split; Oracene remains a focal point of the family.) The lessons started before Venus and Serena, the two youngest, were 5. A million hours of practice later, Venus and Serena emerged as the family prodigies, turning pro in their teens, and then turning women's tennis on its head. A sinewy 6 foot 1, Venus had a wingspan, speed, and power unheard of at the time. She and Serena unleashed a new generation of players: women who could blast away from anywhere on the court. Their reward? Criticism, tinged with racism, for being too strong and too muscled, which they handled with grace and relentless honesty. And championships. Play hard, work hard, and enjoy both. "At EleVen, we have a clear point of view," says Williams. "Our focus is on being your best, bringing your best, living a healthy lifestyle, and enjoying the clothes you wear. Who we are is distinct. That makes us stand out. We don't want to be anyone else. We want to be EleVen."

Translated to the retail level, a sports brand such as EleVen needs a core athletic-apparel franchise augmented by fashion wear. For EleVen, that entails four deliveries per season in activewear and a fashion drop -- new duds -- every six weeks. The latest is a line called Epitome. Williams not only designed it; she's also the lab rat. "She doesn't come in and point to five things and we make that," says Ilana Rosen, the COO. "If you are going to discuss it with an account, the biggest takeaway is that it's an authentic brand. She's done it. If she's not going to wear it, we're not going to make it."

At a fashion show in Dubai, models wear outfits from EleVen’s Prism collection.

CREDIT: Courtesy EleVen by Venus

Not only is Williams going to wear her own outfits, she's also going to gain free advertising by playing in them. And if necessary, she'll make a sales call.

Two days after her fourth-round exit at the 2016 U.S. Open, Williams was back in business mode, meeting with potential retail partners. "If she knows somebody and can bang on the door, she has no problem doing that," says Rosen. EleVen is on a mission to expand its distribution, and being a tennis star can certainly get you a meeting with buyers. Advantage Venus. "They know your name, and they respect what you've done in athletics," says Williams. "But they don't automatically think you can transfer that focus to a business."

Williams is no stranger to battling back. Her 4-6, 7-6, 9-7 defeat of Lindsay Davenport in the 2005 Wimbledon final is a classic -- and that's essentially where she was with EleVen in 2015. She'd established the brand about 10 years before, nurturing it as her tennis game soared. In the late '90s, she'd had an endorsement deal with Reebok and her own signature line and reupped in 2000 for $40 million -- then the richest endorsement deal for a woman athlete. But Reebok lost the sneaker wars to Nike and was eventually sold to Adidas. Williams launched EleVen as an exclusive line for the then-hot Steve & Barry's chain. (Sarah Jessica Parker and other celebs also got their own lines.) The company over­expanded and got smashed by the Great Recession. It went bankrupt in 2008. Williams made a deal with a company in Los Angeles to do manufacturing for EleVen while she handled design. But without adequate distribution, among other issues, it was a losing game.

At the same time, her tennis game began to suffer. She learned in 2011 that she has Sjögren's syndrome, an auto­immune disorder that produces joint and muscle pain. The resulting flu-like symptoms left her chronically tired and often made it hard for her to breathe.

Williams had hit a wall, as so many entrepreneurs do. She'd worked hard to get established, and to get distribution and sales, and then, not only does the economy crash, but her body goes haywire as well, interfering with her livelihood. True to the jock cliché, Williams wasn't about to quit. She went to work with doctors and changed her diet to recover physically.

For help in recharging her business, she called on some high-powered friends. Sallie Krawcheck, former CEO of Smith Barney and now the head of Ellevest, a fintech startup aimed at women, became an unofficial adviser after a mutual friend got them together. "She's a serious businessperson and has an inquisitive business mind," says Krawcheck. "I've given her advice when she's asked for it, mostly along connections that I could make for her, experts to become part of her team or advisers."

And Williams has supported her friend as well. She's an investor in Ellevest, which is focused on the gender gap that women face not only in pay but also in investing, and how resolving those gaps demands different investing philosophies and strategies for women.

That gender pay gap issue is one that falls right into Williams's court. After rising to the Top 10 on the WTA Tour, she emerged as a leader, an outspoken advocate for women. She was ultimately an unstoppable force in closing the prize-money disparities that existed between men and women in Grand Slam tournaments. She even faced down the toffs at the All England Lawn Tennis & Croquet Club (where the Wimbledon tournament is held) the day before she played the 2005 final. She was 25. Her willingness to lead was perhaps a precursor to her role as a business owner. Their shared experience of gender issues made Williams a natural investment partner for Krawcheck and Ellevest. She took a piece of the startup's second financing round. Last spring, Krawcheck organized an informal meeting in San Francisco so Williams could meet with "awesome" women entrepreneurs and VCs.

In 2015, Williams earned a business degree from Indiana University East without taking a break from tennis. Still on tour, she's now getting a master's in interior architecture.

CREDIT: Art Seitz/Newscom

By 2015, she began to reboot EleVen, realizing that the brand wasn't in a position to grow. She decided to buy out her manufacturing partner and assumed sole ownership. The need for a top-shelf operating manager led her to Rosen, a former partner at the retail strategy and management consulting firm Parker Avery Group who has worked at major retailers and boutique investment outfits. Rosen spent a couple of months as a consultant to Williams to help her develop a three-year strategic road map for EleVen. The experience convinced Rosen to go all in. "After spending a short period of time working side by side with Vee, and seeing her vision and goals coming to fruition, my passion and love for the brand grew," she says.

In an industry where brand cachet comes and goes -- think of Ellesse, Tensor, or Fila -- Williams's challenge is to create a brand that won't lose its power when her backhand inevitably does. She's more than aware of the issue: "A lot of celebrities put their name on something like a clothing line and suddenly they come out with 500 SKUs, and no one understands how that could happen, because there was no culture, no message -- they just suddenly appeared."

Running an apparel company and being a tennis star don't seem to have much in common. Tennis is the selfish pursuit of perfection. Your team (agent, coach, hitting partner, physio, cook, etc.) is dedicated to your winning. In business, the owner has to put the team in position to win. "On the tennis court, it's just me," says Williams. "I'm very hard on myself, because I have to get the whole job done. In tennis, I believe in one winner. That's a great thing about business. There isn't just one winner. There's room for everyone to win if they deserve it. I love that."

And unlike on the court, in business a do-over is possible if something doesn't go according to plan. After months of work, Williams decided to completely scrap her first collection. "When you're first starting," she says, "and you're trying to understand what your voice is and what you want to say, sometimes it can be easy to be unoriginal and easy to think about what everyone else is doing. I wasn't pushing myself enough."

Likewise, she had to make a tough call on dumping her manufacturing partner. It's a classic make-or-buy decision, especially for young companies, and she had got it wrong. "We should have been more hands-on and kept production in-house," she admits. "Perhaps I'm not a production expert, but since then I've learned a ton."

"They know your name, and they respect what you've done in athletics. But they don't automatically think you can transfer that focus to a business."

The company still does most of its manufacturing in L.A., in part for marketing reasons and also because it allows for faster manufacturing. "Made in the U.S. is important to us," says Rosen.

EleVen is headquartered near Williams's home in Palm Beach Gardens, Florida. Here she has centralized the once-disparate parts of her business. When she's in Palm Beach Gardens, she trains daily, hitting the tennis court and then the gym for strength and cardio.

V-Starr created these interiors for mixed-use projects the Manor at Lauderdale by the Sea (top) and Town at Pembroke Pines, both in Florida.

CREDIT: Courtesy V-Starr Interiors

That job behind her, she heads to the office. Despite having Sjögren's, her action-figure energy level is the first thing that outsiders tend to notice. Williams says she can't go to the local multiplex because "the thought of going to the movies drives me crazy, because that would mean I would have to sit still."

Working for a boss like that could be crazy-making, but Williams says she knows to give employees space to do their jobs. "I like to make people happy," she says. "But I can never let that get in the way of telling the truth and having tough conversations when you have to. I like to make it a positive. I've never been a screamer. I'm like the reggae girl: 'Hey, mon. Got to do a little better, mon.' "

Williams's energy will get distributed around the world on the tennis tour. It starts in January in Melbourne with the Australian Open; moves on to the European clay circuit in February, ending with the French Open in May and June; on to the grass and Wimbledon in July; back to North America in late July and through the U.S. Open in August and September; and then on to Asia. Williams checks in at least twice a day with the home office, using whatever technology is available.

At EleVen, the joke is that tennis "is that thing Venus does," says Rosen. And she plans on doing it until the 2020 Olympics, when she'll be 40. That would be a phenomenal achievement. So would making EleVen the lifestyle brand she's envisioned. The company plans to add a line of bags and might expand into footwear and eyewear. "I love to see things grow," says Williams. "I love ideas. I love putting things together. I would also like to be seen as a flexible leader, someone who can adapt and change and grow and help the people around her succeed too."

You can't put that in the trophy case next to the Olympic medals and the silverware from Wimby or the U.S. Open. But it would ultimately define her as a champion entrepreneur. Which would be no small achievement.

--Additional reporting by Marli Guzzeta.