Reese Witherspoon says her 'aha moment' in business came after realizing she needed help

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

Reese Witherspoon opened up about the struggles she faced while 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's founder, Seth Rodsky, said it was initially "scary" not knowing if she would recover her investment.

"Every day, I woke up thinking, 'Oh my god, I'm not gonna get my money back.' But I would rather bet on myself and lose that money trying hard. I woke up every single day, and I was like, 'I am my own lottery ticket,'" said Witherspoon, now 48, via The Hollywood Reporter.

At the time, she already had the Emmy-award-winning HBO series "Big Little Lies" under her belt, as well as "Gone Girl" and "Wild," two films that received box-office success.

Still, she said she had only four employees and "couldn't keep the lights on."

"I remember the accountant calling me going, 'You didn't make enough money producing those three things to keep four employees,'" she said. "I was like, 'I'm doing something wrong,'" she recalled.

That's when the "Legally Blonde" star had an "aha moment."

"I was like, I need to have help. I don't have a business plan," she said.

Witherspoon sought help from Sarah Harden, the current CEO of Hello Sunshine. After taking on 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've had women driving action. There's room for excellent storytelling [and] finding the combination of IP, talent, and the right partners," she said.

What makes a business partnership work

When they first started working together, Witherspoon recalled asking Harden the "dumbest questions you can possibly ask for a year," she said.

"I'm sure she was like, 'Oh my God.' She'd go home, and I'd be like, 'My business partner's an idiot.' Like how did she not 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 the effort to make things work, even when challenges arise.

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

"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 just like me, 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 she loves business partnerships between people with different skill sets, reflecting on when she first met Esther Kaplan.

"I was able to recognize she was my opposite," Corcoran said. "She was great at file systems, personnel systems, computers, finance, legal. Everything that I sucked at. And I was great at marketing, recruiting, brainstorming, PR, the bullcrap area of business. And she hated it. So, we were perfect partners."

Kaplan went on to become a longtime president of luxury real estate company Corcoran Group, — which Corcoran sold in 2001 for $66 million

In 2021, Witherspoon's Hello Sunshine was sold to Candle Media, a media firm backed by the 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.