Reese Witherspoon attributes her business success to vulnerability

• Reese Witherspoon said she initially struggled to run her media company, Hello Sunshine.
• Her business partnership with Hello Sunshine CEO Sarah Harden helped turn things around.
• Witherspoon recalled asking Harden “the dumbest questions,” but said her vulnerability helped the deal.

Reese Witherspoon has opened up about the struggles she faced when starting her media company, Hello Sunshine.

Speaking at Hello Sunshine’s Shine Away conference in Los Angeles on Saturday, the actor, who founded the media company in 2016 with Strand Equity founder Seth Rodsky, said it was initially “scary” not knowing if he would get his investment back.

“Every day I would wake up thinking, ‘God, I’m not going to get my money back.’ But I’d rather bet on myself and lose that money trying so hard, I woke up every day and said, ‘I’m my own lottery ticket,'” Witherspoon, now 48, said via The Hollywood Reporter.

At the time, he already had the Emmy Award-winning HBO series “Big Little Lies” under his belt, as well as “Gone Girl” and “Wild,” two box-office hits.

Still, she said she only had four employees and “couldn’t keep the lights on.”

“I remember the accountant calling me saying, ‘You didn’t make enough money making those three things to keep four employees,'” she said. “I said, ‘I’m doing something wrong,'” she recalled.

That’s when the “Legally Blonde” star had an “aha moment.”

“I said I need help. I don’t have a business plan,” she said.

Witherspoon enlisted the help of Sarah Harden, the current CEO of Hello Sunshine. After taking up the role in 2017, Harden helped the company hire executives and create infrastructure, Witherspoon said.

Harden told Business Insider in 2018 that the media company’s goal is to bring different perspectives, stories and narratives to life.

“There are too few stories where you have women driving the action. There’s room for great storytelling (and) finding the right combination of IP, talent and partners,” she said.

When they first started working together, Witherspoon recalled asking Harden “the dumbest questions you could ask for a year,” she said.

“I’m sure he said, ‘Oh my God.’ She was going home and I was like, “My business partner is an idiot.” How she didn’t know, but she was so patient with me and let me be vulnerable,” Witherspoon said via People.

Ultimately, “vulnerability is what led to our success,” she said.

When it comes to business partnerships, it’s about striving to make things work, even when challenges arise.

In 2021, Jonathan Alpert, psychotherapist and performance coach, told BI that business partners should understand the communication styles of their business partners and know how they like to resolve conflicts.

“What works for you is good for you and what works for me is good for me,” Alpert said. “But we have to try to meet in the middle and try to understand each other’s style. If I expect you to communicate like I do, I’m probably setting myself up for failure or disappointment.”

Being able to complement each other’s skills is also key.

In 2018, Barbara Corcoran said he enjoys business partnerships between people with different skill sets, reflecting on when he first met Esther Kaplan.

“I was able to recognize that she was my opposite,” Corcoran said. “She was great at file systems, personnel systems, computers, finance, legal. Everything I liked. And I was great at marketing, recruiting, brainstorming, PR, business crap. And she hated it. So we were perfect partners.”

Kaplan became the longtime chairman of the luxury real estate company Corcoran Group, which Corcoran sold. in 2001 for 66 million dollars

In 2021, Witherspoon’s Hello Sunshine was sold to Candle Media, a media firm backed by private equity group Blackstone Group, for $500 million.

A representative for Witherspoon did not immediately respond to a request for comment from BI sent outside regular business hours.