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How Reese Witherspoon went from actress to successful entrepreneur

Her multifaceted career makes for an inspirational story.

Reese Witherspoon is undeniably best known for as an A-list actor; she’s had one hell of a career, starring in cult classic films (like Legally Blonde, Cruel Intentions and Election) as well as hit television shows (like Morning Wars and Big Little Lies).

Reese even won the prestigious ‘Best Performance by an Actress in a Leading Role’ Academy Award for playing June Carter in the biopic Walk the Line.

However, Reese has delved into multiple realms outside of acting; the biggest accomplishment of which is arguably co-founding the media company Hello Sunshine with Seth Rodsky.

Reese’s motivation to start Hello Sunshine stemmed from her frustration with the limited opportunities for women in Hollywood, both in front of and behind the camera.

She believed that there was a significant gap in the entertainment industry when it came to showcasing complex and diverse female characters and narratives.

Reese Withersppon

This ignited one of the main driving factors behind Hello Sunshine; Reese desired to challenge the status quo and create more meaningful, multidimensional roles for women in film and television.

To achieve this, Hello Sunshine has always and still does solely focus on producing and developing content that amplifies female voices, championing female-driven narratives, and celebrating the diversity of women’s experiences.

And while Hello Sunshine is a wildly successful company today – it’s been responsible for multiple award-winning projects, like Where The Crawdads Sing, The Last Thing He Told Me and Daisy Jones and the Six, just to name a few – it wasn’t smooth sailing in the beginning.

Speaking at the 2023 INBOUND conference in Boston, Reese explained that when she was first getting the company off the ground she had to invest her own money into the business; despite being advised not to.

“I was told not to put my own money in it several times by many, many advisors. I saw people who were taking money from studios, and I saw how watered down the product was. I saw that they were sitting on material that never got made,” Reese said.

Reese Witherspoon

“And I thought if you were to function and do something differently, you have to think about it differently. And you have to capitalise it differently. So probably about a year and we had two of these three Oscar nominations, we had a television show that got done. And I couldn’t keep the lights on,” she continued before adding her ex-husband Jim Toth helped her to better sort out Hello Sunshine’s finances.

“I approached my husband at the time and a business partner and retooled the business plan. And so we went ahead to raise capital, which was a whole lot of asking people for money. It was terrifying… [But] every day I would wake up and I would do something to further my dream.”

Hello Sunshine isn’t the only company Reese is behind though. In 2015, she launched the clothing line Draper James.

Named in honour of her grandparents, Dorothea Draper and Wiliam James Witherspoon, Draper James offers clothing, accessories and home decor that “recapture and celebrate” all that Reese loves about and remembers about her grandparents and the South (Resse was born and grew up in Louisiana).

Aside from co-founding Hello Sunshine and founding Draper James, Reese has also dabbled in producing.

Reese Witherspoon career

Reese has been a producer for nine projects (including Gone Girl, Wild and Your Place or Mine) and the executive producer on 19 projects (including Legally Blonde 2: Red, White & Blonde, Tiny Beautiful Things and Little Fires Everywhere).

Sure, most actors foray into producing but it’s no easy feat. Producers are responsible for securing the rights to scripts, coming up with story ideas and hiring writers. Executive producers do all of this and more; they manage legal, financial and promotional aspects, and are ultimately, the face of the production.

But that’s not all; Reese is the author of two children’s picture books: Busy Betty and Busy Betty and the Circus Surprise.

Plus, speaking of books, Reese also founded – in partnership with Hello Sunshine – a bookclub. You can read all about Reese’s Book Club here.

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