Serena Williams, Reese Witherspoon Share Lessons Learned as Women Entrepreneurs

Tennis and acting made them famous, yet Serena Williams and Reese Witherspoon have also built businesses that advocate diversity and inclusion—and at times faced adversity in the process. Learn more from their conversation on purpose-driven entrepreneurialism.

Mary Hayes Weier November 16, 2020
Image placeholder

Serena Williams and Reese Witherspoon are widely recognized for their amazing talents— Williams as a tennis champion with 23 Grand Slam singles titles, and Witherspoon as an Academy Award-winning actress. Yet both women have been pouring their energy into businesses that are helping to create a more inclusive world.

Witherspoon founded Hello Sunshine, a media company that focuses on female-centered stories told through film, television, podcasts, and books. Williams leads Serena Ventures, which invests in companies that embrace diverse leadership. And, each has channeled her passion for fashion into businesses: William’s Serena and S by Serena, and Witherspoon’s Draper James.

During our global digital event, Conversations for a Changing World, Williams and Witherspoon sat down for an interview with award-winning journalist Soledad O’Brien—an entrepreneur herself as the founder of Starfish Media Group. Here are four takeaways on purpose-driven entrepreneurialism from their conversation.

Prove Them Wrong

Don’t let others’ doubts about your abilities hamper your motivation to start a new venture. In fact, Williams has flipped that negativity on its head and turned it into personal motivation.

Williams points to her decision to start a fashion line. She studied art and fashion and felt prepared for the endeavor, even when some suggested she stick to the tennis court. “Tell me no, and I'll show you that I can do it. That is something that really inspires me,” she said.

Those experiences also inspired her to start Serena Ventures. Shocked by the statistics around how little venture capital funding goes to women- and minority-owned businesses, she saw an opportunity to connect more of them with investors. Her message to investors who haven’t considered the value of diversity: “Look at people of color, look at women who also have wonderful ideas and can have an opportunity to create something really awesome and really cool.”

Stick to Your Principles

Witherspoon said she started a media company due to her frustration with the lack of representation of women in the film industry. Yet it was also important to her to avoid taking funding from those who didn’t align with her priority of making female-centered films, which is why initially she self-funded the business.

“I broke the number one rule when you're starting a company in Hollywood, which is, don't put your own money into it,” she said. Her point of view: “I'm going to put my money where my mouth is, and I believe enough in myself. I always say, I am my own lottery ticket.”

“Taking the light that was always shining on me and shining it on someone else—that feels like my purpose.”

Reese Witherspoon Academy-Award Winning Actress, Producer, and Entrepreneur

Yet mentors are also important when starting out in business, she said. “I didn't know what ‘seed funding’ and ‘Series A’ and ‘Series B’ was all about until people really took the time to walk me through it. It’s a vernacular you pick up pretty quickly, but it's also vernacular that can shut out women, people of color, and people who don't have the same opportunities.”

Roll Up Your Sleeves—And Get to Work

If you want to see your business succeed, no job should be too small. Williams said that with her fashion business, “I am a do-all. I will literally be on the floor, cutting patterns in the middle of the night.”

She added that she’s also styled models during photo shoots, helping with hair and makeup. When it comes to her fashion business, “Nothing's too good for me. I do everything that you can imagine . . . I try to be extremely humble.”

Share the Limelight

Witherspoon has worked on film production teams of several hundred people since she was 14, experiences that started her on a journey of understanding the importance of teamwork. “I always say 10% of my job is acting, and 90% of my job is getting along with other people,” she said. 

“Tell me no, and I'll show you that I can do it. That is something that really inspires me.” 

Serena Williams Tennis Champion, Entrepreneur, and Philanthropist

Witherspoon said she’s grateful for her own success and wants to help women succeed in all areas of the industry, including as directors, writers, and show runners. And, she’s encouraged by the reception of “Reese’s Book Club.” Every month, she picks a book she loves with a woman at the center of the story and shares it with the book club’s 1.8 million followers on Instagram.

“Just in the past year, I've had two authors reach out to me and say, ‘This has financially changed my life,’ and, that has changed my life,” said Witherspoon. “Taking the light that was always shining on me and shining it on someone else—that feels like my purpose.”

More Reading