How Venus Williams Is Serving Up Her Entrepreneurial Dreams

Tennis trained her to be a one-woman, hyper-focused, do-it-all-yourself machine. But as she's discovering, entrepreneurship requires more balance.
How Venus Williams Is Serving Up Her Entrepreneurial Dreams
Image credit: Pieter Henket
Magazine Contributor
15+ min read

This story appears in the December 2017 issue of Entrepreneur. Subscribe »

Venus Williams sits in a conference room, surrounded by branding executives and healthy snacks. And the room is starting to get a little chatty. People aren’t focusing on the task at hand. “Shall we continue?” Williams says softly. Most of what Williams says is spoken softly, with a quiet authority, and it’s effective. The assembled people snap back to attention like a rubber band.

A conference room may not be where tennis fans picture Venus Williams. But it’s a setting where she’s increasingly at home.

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It is mid-September, about two weeks after Williams lost in the semifinals of the U.S. Open to Sloane Stephens. What follows the loss has been a whirlwind, full of business meetings for her growing portfolio of outside concerns, which she fits in between training sessions and preparations for the fall Asian season of the women’s tennis tour. Today’s is about EleVen by Venus Williams, her athleisure company, which sells workout gear that Williams also always plays in. The company is thriving, growing 300 percent year over year, and has hired boutique ad agency NSG/SWAT to pull together a look book for its spring/summer 2018 collection. This is what retail buyers and marketing companies will soon see, and Williams and her team are here to review the latest draft.

Brian Riordan, NSG/SWAT’s president, calls up some images on a wall-mounted flatscreen while Williams leafs through some printouts. He narrates the changes they’ve made in response to EleVen’s earlier notes, making sure to highlight some necessary reshoots. Williams is pleased with these, particularly compared with the old set of photos. “Those girls looked so wholesome,” she says of the last draft. “They weren’t sweating, and their hair wasn’t messy.” Then she gathers her voluminous, and somewhat unruly, ponytail. “See?”

Williams talks a lot about authenticity, and here, she’s hammering home the point: Real women should look like they’re doing real work, and real work is nonstop. She also hit on this a few days earlier onstage at an event called WWD Digital Forum, where she mentioned that she goes straight from the gym to the office, apologizing to her team for her sweatiness when she arrives. The crowd laughed, assuming she was exaggerating for comic effect. But no. Venus Williams’ hair is “messy” because she really does come straight from her daily training session to the office, still in her gym clothes, which, of course, she designed.

Williams’ time is precious. Ilana Rosen, EleVen’s COO, jokingly calls Williams’ day job that “part-time tennis thing she does,” but that part-time tennis thing requires six hours of training a day and 11 months of traveling for tournaments across the world. And in addition to EleVen, Williams has founded V-Starr Interiors, an interior design company. These aren’t passive activities; she’s regularly at the office, directing style decisions and sometimes even working in the warehouse. She and her sister Serena are also part owners of the Miami Dolphins, the first African-American women to own a stake in an NFL team; and together, the sisters opened the Yetunde Price Resource Center, an outreach and social services center in Compton, Calif., where they grew up and where their sister -- and the center’s namesake -- was murdered in a drive-by shooting. 

There is, of course, the traditional way of looking at this lineup of interests: It is the work of a professional athlete contemplating retirement and building a foundation for the next phase of her career. Indeed, many people expected Williams to step back when she revealed in 2011 that she was battling Sjögren’s syndrome, a chronic, incurable immune system disorder that afflicts her with sore joints and muscles. Instead, she came back and won gold in the 2012 Olympics. Now, at 37, she just wrapped up an amazing season that saw her return to the top five in the rankings, reaching the finals of the Australian Open and Wimbledon along the way, and she refuses to talk about retirement. “I have no plans of stopping anytime soon,” she tells me. “It seems somehow that 2020 Tokyo is on the horizon. Isn’t that wild? I’m trying to stick around for that.”

And after following Williams on three business trips throughout Manhattan, I can see that this work isn’t just about an eventual retirement she won’t speak of. It’s about something every entrepreneur can understand: a relentless drive to build, to grow, to embrace opportunity and, most important, to oversee it all herself. 

“My mom was like, ‘You can’t do everything, you don’t need to do all that, tennis takes a lot of energy, you need to focus,’ so I would just not tell her what I was doing,” Williams says. But Mom is right. Williams is attempting not just an impossible task but a foolish one as well, and she’s beginning to come around to that notion. She is finding that to truly succeed, she must go against the instinct she has spent a lifetime honing.

In other words, Williams is learning to step back a little. To collaborate. To delegate. To trust in others’ competency. “It was good to be like that,” Williams says of her hard-driving approach to her life, her game and her businesses. “That’s who I am, and now I am evolving. Project 2.0: Venus Gets a Life.” 

Image Credit: Pieter Henket

Venus Williams is many things, but everything starts, rather famously, with being her father’s daughter. 

The legend of Richard Williams, one of the most remarkable tennis coaches in the sport’s history, is almost as storied as that of his daughter’s. The short version: Inspiration struck when, listening to coverage of the 1978 French Open, Richard heard sportscaster Bud Collins say, “Forty thousand dollars isn’t bad for four days’ work.” He soon hatched a plan -- which he eventually wrote down over 78 pages -- to raise two children to be tennis champions. These children hadn’t been born yet, and he didn’t really know how to play tennis. He learned through reading magazines and watching matches; but mostly, Williams writes in the book Come to Win, her father “taught himself his own theories.” (Richard himself has credited a tennis-savvy booze hound named Old Whiskey, whom he paid by the pint.) When he ultimately did have children, he passed the vision along to them. Venus declared at age 12 that she’d win Wimbledon five times. Then she went and did it. 

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Tennis requires technical mastery, of course, but as the old cliché goes, the game is as mental as it is physical. Players must be constantly thinking without getting in their own heads. Let’s say your opponent is Caroline Wozniacki, the former world number one. Wozniacki is a brick wall, so good at defending that she can run down almost any ball from the backcourt and return it to you. That then forces you to keep hitting until, out of frustration or exhaustion, you make an error. Wozniacki is betting on that. So if you’re playing her, how do you win? Do you try to overpower her? Do you play more conservatively? Do you run to the net to shorten the point? Once you’ve chosen your strategy, do you stick with it even when it doesn’t work, or abandon it and try something else? You might come up with answers ahead of time with your team, but on the court, the only decision-maker is you.

Williams’ solution is to be a relentless attacker, the opposite of Wozniacki (to whom she has lost only once). Her style is built around continuous offense, which requires split-second decision-making, commitment to choices and a kind of champion’s amnesia that allows her to remain undisturbed by failure -- and unrelaxed by success. 

In tennis, you develop a way of thinking through drilling -- refining until every move is perfect and repeatable, and until your mind can move at the speed of reflex. “The racket has to be like this or like this,” Williams explains, adjusting the angle of her hand by five degrees, often the difference between the ball going over or into the net. “It’s important, every little nuance, especially when you’re under pressure; you gotta know that your technique is there and just be confident and play.”

That mentality, that drilling, has shaped how Williams thinks about everything. Jenny Goldstock Wright, who, as CEO of Driving Force Group, helps spearhead the Williams sisters’ philanthropy, experienced that recently during a family illness. Earlier this year, doctors found that one of Wright’s sons had tumors in his eye sockets. (He’s fine now.) Williams learned about it and texted Wright to see how the family was doing. “She doesn’t say, ‘Oh, thank God he’s OK,’ which would have been a very nice response,” says Wright. “She says, ‘Can you tell me what exactly it’s called?’” Wright complied, and soon Williams was drilling down into the details of the illness. “She writes me back: ‘Has he gotten a full lymph scan? Could this be an issue of drainage, or is it an issue of something else?’ I answer back. It went on for two hours. That’s how she thinks -- in depth, thoughtfully, covering all the bases.”  

Williams has brought that sensibility into her business ventures as well. Her decisions are gut level. “I know when it’s right,” she says. “It’s all about making a decision and executing it. I never want to be part of a big corporate wheel. I definitely don’t want to spend too much time on something, because then it gets convoluted. Sometimes the right instinct is the first instinct, and then you just have to move on that.”

But of course, drilling is not always helpful. Recently, Williams started taking dance classes. “I was so technique-driven,” she says. “The teacher was like, ‘Do you want to learn a routine?’ and I was like, ‘No, I want to drill! I want to drill; why aren’t we drilling?’” And it’s not always helpful in business either. Business contains contradictions that sport does not. Instinct is valuable, but so is flexibility. Repetitive motions may lead to success, until they’re outdated and lead to failure.

Williams is adjusting to this balance. At one point, she explains EleVen’s design direction like this: “We used to focus on what’s trending, and then I realized it’s not as important as what my vision is.” And yet a little while later, in the meeting at NSG/SWAT, she disapproves of the prominence of a red shirt on one page -- and her vision slams into what’s trending. EleVen COO Rosen quickly notes that they sell a lot of red clothes. “You might not want to listen to me,” Williams says, lightheartedly. 

The red stays, her vision be damned.

Image Credit: Pieter Henket

In Come to Win, Williams explains about how her father and Oracene Price, her mother, would often tell their children to “think entrepreneurially.” In the van on the way to tournaments, the elder Williams would play his daughters tapes about how to make money buying foreclosed properties, so they could learn the mechanics of the real estate market. (Now that Serena has a baby, Venus can’t resist a throwback: “Serena wanted us to buy books for the baby shower, for the baby, and I got a foreclosure book!” she says, laughing. “I was like, ‘This is very appropriate.’ I also got Who Moved My Cheese? And I got some baby books, too. But it was like: The tradition must continue!”)

The real goal of those tapes, she writes, was to train Venus and Serena “early on to be independent thinkers. Of course, he was also training us to be financially independent.”

Independence is fundamental to how Venus Williams does everything. And it’s what ultimately led her to make the most consequential decision in EleVen’s history: to bring it back from the dead. The brand originally began in 2007 as a partnership with the clothing chain Steve & Barry’s. “Collaborating with a dedicated team of Steve & Barry’s designers, Williams has immersed herself in the creation of every piece,” the retailer announced at the time. But Steve & Barry’s declared bankruptcy a year later. EleVen would resurface occasionally over the next four years, partnering with brands like Ralph Lauren, but Williams was quietly honing a more purposeful brand. She’d learned a lesson many small businesses do: When you anchor yourself to a larger entity, you can’t control your own fate. 

“I wanted the brand to be what I wanted it to be,” she says. “I had a specific vision for things and how I wanted them to go. I wanted to control what the brand looked like and the messaging, and what it said. I wanted to control the distribution points. I wanted to control the future of EleVen and not just [have] one distributor or pay for a licensing deal.” In 2012 she relaunched the brand herself with a manufacturing partner. (The capital V in the name is obvious, but why 11? “Ten is just a number,” Rosen explains.)

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But Williams would soon find that a founder’s vision is not always synonymous with a focused brand. Passionate entrepreneurs tend to say yes to ideas they love, even when they should say, “Great idea, but not for us.” Williams won’t catalog the specific mistakes of those early days, but suffice it to say, the brand’s focus got lost. So in 2015, she turned to her now-COO Ilana Rosen, originally as a consultant. “When I first met her, we talked about what she really wanted this brand to be,” Rosen says. “What’s it about, what’s the mission, what’s the ultimate goal?” 

With goals established, Rosen could build a system to achieve them. “A lot of people had their hands in EleVen, all in different places,” Rosen says. “The first thing was to build an organizational structure that made sense, centralizing everything in South Florida. Publicity, merchandising, design, conception -- all of it. The only thing we don’t do is make [the clothes] and sell them, but [we] oversee that in Los Angeles.” Now operations are so centralized, EleVen shares an office with Williams’ other company, V-Starr Interiors, and it opens into EleVen’s warehouse. “If we’re low on inventory and it says we have only eight units of a style left, we literally can walk two feet into the warehouse and look at the physical box.”

This has positioned EleVen to take advantage of the booming athleisure market. “We’re looking to more than double this year, and then to ultimately catapult,” Rosen says. In addition to the company tripling revenue last year, she says, its ecommerce business alone has grown 700 percent since 2015. And yet, EleVen remains mindful of not repeating its past mistakes: Not all growth is healthy growth. If an opportunity arises, but it doesn’t fit, “we’re not going to force it and go against that strategy.” By way of example, she offers Zappos. The e-retailer wanted to carry EleVen’s clothes, but Williams and Rosen didn’t leap at the opportunity at first. “They have a huge compliance manual -- where the stickers have to be, what you have to do, where the label has to be on the box,” Rosen says of Zappos. “If you don’t get those things right, you’re one and done. They’re not coming back.” So they proceeded carefully, really determining whether the partnership would work, before finally saying yes.

The same caution applies to international expansion, which EleVen is doing slowly and steadily. “We use the phrase ‘world domination’ a lot, and we mean it,” Rosen says. EleVen currently sells in Europe, Nigeria, Australia and New Zealand. Now it’s working on China, where Williams plays frequently and has been presented with plenty of business opportunities -- but knew better than to rush in. Instead of moving into the market on its own, EleVen created an exclusive collection for China with retailer Lane Crawford. “We thought that made sense because when we launch with them, they’ll understand their customer and how we can relate to them,” Williams says. 

“Really with China, we’re dipping our toe,” Rosen says. That’s very different from drilling down. But these days at EleVen, they don’t see that as a bad thing.  

Image Credit: Pieter Henket

After the EleVen meeting with NSG/SWAT, Williams flew back home to Florida, where for 10 days she trained, went into the office and labored over homework. She’s now taking classes toward a degree in design -- although she refuses to reveal where, because she’s not currently getting straight A’s. “Lately, I’ve been trying to figure out how to get the best out of it without going crazy. That’s how your grades  drop,” she says. “I finally learned what school was about. It’s about getting the best out of it and using your time wisely. I maybe realized that too late. I always brought that tennis mentality to it, like, perfection, perfection, perfection.

And then, on the 10th day after the meeting, she’s back in Manhattan for more meetings. We reconnect at the offices of rug designer Obeetee. V-Starr is designing one of the 17 rugs for Obeetee’s launch of the Express Collection, a new line of color-customizable rugs to benefit the Design Industries Foundation Fighting AIDS. The two companies are also in talks to release a series of new rug designs by V-Starr. “We had a little design competition in the office and were able to come up with 23 rug designs, and they’re all amazing,” says Sonya Haffey, the design director who runs V-Starr’s day-to-day operations. “So we were looking at them all and thought, We should just make this a whole collection.” 

Today Williams is touring Obeetee’s Manhattan showroom, looking at the stacks of various rugs they offer, discussing timetables, manufacturing methods and price points. Sales manager Gretchen Auer runs us through the ways Obeetee’s rugs are made and turns one over to show us what a rug with 250 knots per inch looks like. Williams kneels down and touches it, asking about the materials and the details of the various dyeing processes. Two men follow us, bending down to pick up a rug and then peeling it back with a lunge to reveal the one underneath in a synchronized, delicate motion. “I should do that for cross-training,” Williams jokes, and then tells the men not to work too hard for her sake. 

In the past, Williams might have given in to her instincts and seen every rug in the place. But now she takes a languid, pleasurable walk. In the hour or so she’s here, she spends maybe 10 minutes talking about the collaboration. She’s relaxed, taking pleasure in another company’s craft, trusting that its dedication to perfection matches her own. She doesn’t have to drill at all times; she has a team that can do that for her. “I’m not a micromanager,” she says. “I don’t tell people what to do; I expect them to show me the way in their department.” 

It’s funny to hear this, in contrast to some of the other ways she talks about work. Onstage at the WWD Digital Forum a few weeks earlier, she’d talked about physically fulfilling EleVen orders herself. “They don’t really want me on the ladder,” she says. Her staff fears an accident and an injury. “But I do pack some boxes.” Imagine it -- ordering workout gear from a professional tennis player’s company, and the player herself puts it in the mail. Stepping back is clearly still a work in progress. “This year, my goal was to be more balanced, to be more bigger-picture and not be up all night grinding. Writing a treatment for marketing -- now I let other people do that. I find the inspiration and write a page or two, but I don’t write the whole thing. Letting go of pieces and focusing more on the big picture. That’s how I can be more effective.” 

Check out more what Williams has to say in this behind-the-scenes video for our December cover story.

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