Reese Witherspoon, who has been starring in movies since she was 12 years old and producing her own films since 2014, thinks people are finally ready to see her as a producer. That’s because her recent HBO mini-series, Big Little Lies—an undeniable water-cooler hit—was her third major success, after Wild and Gone Girl. And as she explained onstage at Vanity Fair’s Founders Fair in Brooklyn on Thursday, until you score a hat trick, no one is going to listen.
“I finally had my three hits,” she said. “Finally, I feel like the story had changed. I am a producer.” The odds of making it to that level, she said, are particularly stacked against women, who have to “prove themselves twice as hard,” and for whom it can take “twice as long.”
“A guy has one hit and they say he’s going to win an Oscar. A guy has one movie at Sundance and he gets Jurassic Park,” she explained. “A woman has a hit at Sundance and she has to make six more movies.”
In a lot of ways, the obstacles Witherspoon has observed in Hollywood extend to Silicon Valley, as she’s noticed while growing her lifestyle brand Draper James over the last four years. The pressures she faces have grown, too, as she relies on her instincts to know when something will resonate with audiences or with customers.
“I know a movie’s a great idea or a company’s a great idea when I can’t stop thinking about it,” she said. “When I think, Oh my God, I can’t wait to tell that story, or, I can’t wait to sell that dress. I have a good gut.”
That gut, particularly fine-tuned to her Southern sensibility, led Witherspoon to create the now ubiquitous tote bags with the phrase “Totes Y’all” sprawled across them, which she says have created a mini-frenzy. The company has gone through 2,500 units, and has had to reorder the bags six times. When a friend pointed out that her brand should try throwing something with Dolly Parton in the mix, they came up with the idea of selling “What Would Dolly Do” bags.
“I called Dolly. I’ve known Dolly forever,” Witherspoon said. After running the idea by her and offering to donate money to her charity in exchange for the use, she said Parton, whose office is near the Draper James store, did more than lend her name.
“She said, ‘Just go ahead and do it. I want you to be successful.’ And then she went down to the store and bought all the bags,” she said. “She really is an angel from heaven. A little Southern angel.”
Angels and gut feeling and all, Witherspoon still feels the anxieties any new entrepreneur does. “Bearing the weight of a $50 million movie is a lot of pressure, but I learned at a young age that I will not stop until I make my investors their money back.”
One of her investors, Kirsten Green of Forerunner Ventures, who sat next to Witherspoon onstage for the panel discussion, said that for all of Witherspoon’s star power and success, she faces many of the same hurdles entrepreneurs starting in a new area do.
“Reese is so extraordinary in so many ways, but she is an ordinary founder,” she said. “She loves her business, she’s trying really hard to make it work, and it’s hard work. No matter who you are, you’re working hard to make things happen.”
The conversation was part of Vanity Fair’s inaugural day-long summit, which brings together founders and risk-takers to share their stories and challenges of starting and running a business. The centerpiece of the event, at the 1 Hotel at the foot of the Brooklyn Bridge, is a series of one-on-one interviews with entrepreneurs and leaders like Witherspoon, Tory Burch, Kelly Ayotte, Sasheer Zamata, and Emily Weiss.
