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As expected, Reese took to the stage at the first Vanity Fair Founders Fair conference today, during which she spoke about being a woman in business and her recent producing work. The Founders Fair gathers female entrepreneurs from different industries to talk about why they started their companies, how they built their businesses, and the lessons they’ve learned. Reese was joined by one of her investors, Forerunner Ventures founder Kirsten Green, and the twosome were interviewed by Vanity Fair West Coast editor Krista Smith. Reese’s cute little white dress is (presumably) from Draper James. We have the first photos in our Gallery, and scroll on down this post for a short article from the event. We’ll likely have more from this event for you in the coming days …

Vanity Fair’s Founders Fair Conference x13

Reese Witherspoon Explains what Hollywood and Venture Capital Have in Common

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.” “Before it was like, ‘She’s trying. That’s cute.’” 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.

(Vanity Fair)

What Reese Witherspoon learned from having to ask venture capitalists for money

Reese Witherspoon is best known for being an Oscar-winning actress and Hollywood producer. But the Nashville native is also the founder of a Southern clothing and lifestyle brand, Draper James, which she named after her adored grandparents.

And just like any other entrepreneur getting a start-up off the ground, Witherspoon had to seek out and pitch venture capitalists for funding.

“Going around and asking for VC for money is like an audition,” said Witherspoon, speaking on a panel with Kirsten Green, a VC and Draper James investor, at the Vanity Fair Founders Day conference in New York City.

When Witherspoon’s Draper James CEO asked how she thought a VC pitch went, she replied, “‘I think I got the part! I think they want me!'” recalled Witherspoon, smiling. “And then, I was shocked when they didn’t.”

Her name and track record in Hollywood didn’t automatically open investors’ wallets.

“I had to go into lots of different meetings with lots of different venture capitalists and I [had] to pitch the company,” said Witherspoon on the TODAY show. “That was a scary time because they don’t care who you are. It’s whether your business is viable and it’s robust.”

“That was kind of the performance of my life,” she said.

Even as she was talking to many VCs, Witherspoon set her sights on Green, the founder of Forerunner Ventures, known for investing in e-commerce behemoths Dollar Shave Club and Retail leaders including Birchbox, Bonobos, Glossier, Hotel Tonight and Warby Parker are all part of the Forerunner Venture portfolio.

“I really sought out Kirsten. I heard about Kirsten, people were talking about Kirsten,” said Witherspoon at Founders Fair. “It was like I was dating her. I was, like, trying to land the guy.”

In 2015, Forerunner Ventures led a $10 million investment in Draper James, according to investment database Crunchbase. (Private-equity firm JH Partners and investment company Stone Canyon Industries also participated in the round.)

The relationship seems to be thriving.

On the panel, Witherspoon remembered calling Green with a question: “Hey, what is EBITDA? You sent me this whole long email about EBITA, and I don’t know what that is.” (EBITDA stands for “earnings before interest, tax, depreciation and amortization” and is an indication of a company’s performance.) Green answered kindly and without judgement, said Witherspoon.

The respect is mutual. “Reese is so extraordinary in so many ways,” said Green. “You’re also an ordinary founder,” she said, turning towards Witherspoon at Founders Fair. “She loves her business. She’s trying really hard to make it work.”

While Witherspoon had a lot to learn about being a successful entrepreneur, some of her experience as an actor and producer in Hollywood translated. “By the time I was 14 years old starring in movies, bearing the weight of a production — that’s a $30 million movie or a $50 million movie — that’s a lot of pressure,” she said.

“But I have learned over the years, I will not stop until I make my investors their money back, because that is my responsibility.”

Witherspoon credited her success to her intuition. “I know a movie is a great idea or a company is a great idea when I can’t stop thinking about it. And I think, ‘Oh my god, I have to tell that story! Oh my god, I have to sell that dress!'” said Witherspoon.

“If they have infinite possibility and I am excited about them, it’s going to be a win-win.”

According to Green, the key to building a solid business is taking things step-by-step. “It’s finding that balance between being true to a goal, but not being dogmatic about that being the only way it works out,” she said. “Because the reality is that if you do take things in a step-by-step approach, you will evolve as a person, what is in front of you will evolve, the market evolves and it is important to take advantage of that. …

“It’s about taking your big idea and getting very tactical about it.”


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