Reese Witherspooon: Self-Made Businesswoman

While some celebrities simply lend their names to their businesses, Reese Witherspoon sold her dream of a successful clothing line not only to customers but to investors as well.

The Big Little Lies actress and executive producer founded Draper James in 2015 as a way to pay homage to her southern heritage and her grandparents, who she says taught her about “gracious southern living.” The website had 160,000 visitors the first day, and certain items sold out in 24 hours, according to trade publication Women’s Wear Daily.

Witherspoon took the initiative of convincing venture capitalists to invest in her business. “Going around and asking [a] VC for money is like an audition,” Witherspoon said when speaking on a panel in 2017 at Vanity Fair’s Founders Fair conference, an event for entrepreneurial women. After selling in all 50 states and more than 15 countries, Draper James secured $10 million in financing.

Today Draper James has four brick-and-mortar stores—in Nashville, Tennessee; Dallas, Texas; Lexington, Kentucky; and Atlanta, Georgia. Witherspoon has also launched a media and production company, Hello Sunshine, that aims to create content for and by women.

In a discussion with female entrepreneurs sponsored by Crate & Barrel, Witherspoon shared how some of the skills she learned through acting­—such as teamwork, communication, and empathy­—have helped her become a better businesswoman. “I didn’t grow my career up in a corporate environment,” she said. “I was on movie sets, and I thought, ‘I don’t have any skills to run a business.’ But the truth is, I had all these skills.”

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