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

Reese Witherspoon says pitching to venture capitalists is a lot like an...

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."

Actor and producer Reese Witherspoon (L) and founder of Forerunner Ventures Kirsten Green.
Photo by Andrew Toth

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.

Going around and asking for VC money is like an audition.
Reese Witherspoon
Oscar-winning actor

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 Jet.com. 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.)

Photo by Anthony Harvey

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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