Oscar-winner Reese Witherspoon has revealed the secret to her enormous business success – with hard work being at the centre.

Witherspoon might be best known for her role in Legally Blonde, but she wears many professional hats, from Academy Award-winning actor to founder of production company Hello Sunshine and fashion and lifestyle brand Draper James.

Earlier this year, Forbes magazine declared her the world’s richest self-made female actor, with a staggering net worth of US$440 million ($673 million). This was largely due to the 2021 sale of Hello Sunshine, in a deal worth $900 million ($1.4 billion).

Last week, Witherspoon followed that up with the sale of a 70 per cent stake in Draper James to fund manager Consortium Brand Partners. The value and terms of that deal have not been revealed.

Witherspoon remains involved with Draper James and still holds an 18 per cent stake in Hello Sunshine.

But while speaking at customer platform HubSpot’s annual Inbound conference in Boston last week, Witherspoon shut down speculation that the Draper James deal put her in the billionaire category alongside the likes of Oprah Winfrey.

“They’re wrong,” she said.

“That’s enormously flattering, and if I ever touched the bottom of whatever Oprah’s magic golden boots do, I would be so lucky.”

On making space for women

Witherspoon, who started acting at 14 years old, said she began interning behind the scenes aged just 16, to learn as much as she could about film and TV.

But she was disappointed to find a conspicuous lack of female leadership, and grew frustrated with the lack of leading roles for women and how few accurately reflected the female experience.

“I went and did … a listening tour … with each head of every studio, and I said, ‘Just tell me what you’re developing with a female lead’,” she said.

Hello Sunshine’s productions have put women front and centre. Photo: HBO

“Literally none of them were developing anything, except for one studio [which] said, ‘Oh wait, we have a movie with a female lead this year, so we can’t have two’. This was in 2011, guys, this wasn’t like 1925.”

“I thought, ‘This isn’t good enough’ … so I said, ‘I’m going to put my money where my mouth is’ … and I self-funded a company – and that was the first iteration of Hello Sunshine.”

Witherspoon said she didn’t care about the outcome of the eventual sale of Hello Sunshine as long as it proved that storytelling for woman was “meaningful” and “lucrative”.

On highs and lows

Pacific Standard was the production company Witherspoon founded with Australian film and TV producer Bruna Papandrea, which eventually became a subsidiary of Hello Sunshine.

It found immediate popularity with the likes of Academy Award-nominated films Gone Girl and Wild.

But despite the critical and fan acclaim of the company’s projects, Witherspoon – who couldn’t specifically discuss past or future projects at the Boston conference due to the ongoing SAG-AFTRA strike – said it “couldn’t keep the lights on”.

“This was my ‘all is lost’ moment,” she said.

Against all advice, Witherspoon had put her own money into Pacific Standard. She worked with her then-husband Ryan Phillippe and a business partner to “retool” Pacific Standard in a way that made sure they were paid appropriately for their work.

Hello Sunshine launched in 2016 as a joint venture with American telco AT&T’s Otter Media.

On home values influencing business

But asking for money to fund the fledgling production company was no easy feat.

Witherspoon said it was “terrifying” to go from being a successful actor to becoming a business novice. To make sure she “didn’t seem stupid”, she would write down terms she didn’t understand “underneath the table” to look up later.

But she said one of the factors that helped clinch deals was being able to provide references who could vouch for her.

Witherspoon has moved from child actor to multimillionaire businesswoman. Photo: Robert Kamau/GC Images

The actor and businesswoman credited her parents, both of whom have medical and military career backgrounds, for instilling a good sense of work ethic that has served Witherspoon throughout her life and business ventures.

“You wake up early, you stay late, you never complain. You don’t care if it’s cold, you don’t care if it’s raining, you don’t care if it’s hot – no one wants to hear you complain,” she said.

“I had never been to business school … but I did know really critical life skills … which were, show up, do what you say you’re going to do, return emails [and] if you tell someone you’re going to read their script or their material, actually read it pretty promptly and respond thoughtfully.”

Witherspoon also said she was used to rejection, given her experience failing to land acting roles throughout her career. She said she prefers not turn friends into business partners, and is careful about the people who get closest to her.

“They always say the five people you spend the most time with in your personal life and your work life are going to dictate your mood and your success,” she said.

“It’s really important if that person is bringing you down, they’re not adding to your life, it’s time to get out.”

The New Daily attended Inbound courtesy of HubSpot.