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Leading Through Change: Reese Witherspoon on Business Innovation & Leadership

Leading Through Change: Reese Witherspoon on Business Innovation & Leadership

Producer, actor, and Hello Sunshine founder, Reese Witherspoon, got down to business on the last day of INBOUND23. In a candid conversation, she discussed changing the narrative when it comes to female storytellers in Hollywood, while also sharing some lighthearted moments (like dropping a famous line from her "Legally Blond" days) and divulging in what her beige flag is (touching bugs and other creepy crawlers, in case you were wondering). 

Read on for more takeaways from her revealing conversation on building businesses and what her myriad work experiences have taught her. 

[Photo credit: Mike Dawkins/Mike D Shot Me for HubSpot]


What first started as a self-funded dream, Hello Sunshine, quickly grew into a powerhouse media company centered on women and their stories. How did it all begin? After decades of working in Hollywood, Witherspoon couldn’t help but notice a recurring theme. “What I kept seeing over and over again is there’s really a lack of women and female leadership,” she said of the industry’s representation. So, she decided to change that

The company's roots began as Reese’s Book Club and quickly grew into film and television — purchasing the rights to books and transforming them into movies and shows. Other projects include unscripted series documenting everything from female F1 drivers to business owners along with the social media vertical of the company which works with brands to create social media content. 

Although she didn’t have the business acumen from the get-go, she relied on skills that had made her successful in her career: showing up and working hard. “Recognizing what I did have, really sort of off-set what I didn’t have,” she added. “I was never afraid of working hard. And I would always work harder than anyone.”

The takeaway? Sometimes you need to jump headfirst into a project that you believe in. If your experience doesn’t reflect what you’re trying to accomplish, lean into other skills that can be leveraged to your advantage and benefit. And at the end of the day, remember: no one else believes in your dream as much as you do. 

You see a white space and you go, no one else is going to do it. No one else believes in my dream as much as I believe in my dream, so every day I would wake up and I would do something to further my dream forward.

Actually, yes, running a retail business is indeed hard, Witherspoon confirmed while using one of her popular movie lines to describe Draper James, a clothing company she founded a decade ago. She noted the stark contrasts between this company and Hello Sunshine — Draper James is focused on the physical making of goods, and has business considerations that include product, shipping, brick and mortar locations, and the complexity of rent and overhead costs. 

She recently announced the sale of her fashion brand, a move that caused some outlets to speculate if she had made it into the billionaire’s circle — something she quickly (and graciously) shot down. “You can create more scale, and honestly you just need a lot more capital per scale,” she said of the reasoning behind the sale. Now, the brand can focus on larger wholesale opportunities and growth with strategic investment. 

Whether you’re a business owner or an individual looking to maximize your bottom line, it’s always important to embrace change and adapt. Your business model or how you do business may shift over time, but the key is to take it all in stride and make sure you continue to iterate. 


Rejection: it’s something everyone faces at one point or another in their career. Witherspoon's hot take? Other people's opinions of her are none of her business. 

She offered more insight into her POV, underscoring the point that every person you come across will develop an opinion of you, but it shouldn't influence your mood or how you go about your day.  

The sooner you release that feeling of other people’s opinions crushing you or holding you down, you’re free.

Stay true to your work and your convictions. Everything else is just noise. 


Throughout her experience building and growing her businesses, Witherspoon has chosen to champion others, especially women, in the work that she has done. “I think there’s power in partnership,” she commented. “There’s literally no one here that has all of the skill sets you need to succeed." She nodded to her own partnerships with incredible writers and actresses that have helped to elevate the work at Hello Sunshine as examples of that.

A big tenet of our company is: 1 + 1 = 5.

“If they have some proficiency that you don’t have, take 20 minutes to learn what they’re doing. Because it’s invaluable,” Witherspoon added of the learning opportunities that can come from new partnerships with people who bring different skill sets to the table. 

No matter what growth looks like for your business, it will always be critical to add on talent, partners, or team members to fill any gaps, provide balance, and help push goals forward.


Contrary to what the audience may believe, the real power in Hollywood doesn’t lay with producers, directors, or studios… according to Witherspoon, that power belongs to the consumer.

How? Consumers can help influence the spending practices of studios simply by doing things like pre-ordering books from authors or adding shows to a playlist — all of those small behaviors signal interest and intent to companies and can be a powerful tool. 

Conscious spending and conscious consuming of media — that is the wave of the future and that’s what’s moving markets.

Thinking about how and where you spend time when it comes to media, can help shape the future of what media will look like. Want to see more work from female authors and directors? Let the companies in charge know by consuming more of that type of content. 


Aside from dropping business gems, Witherspoon shared plenty of applicable life advice as well. No matter for work or in your personal life she drilled down on the importance of showing up, putting in the hard work, treating people well, and helping others along the way. 

She left the audience with a final thought: “A life that’s in service of helping others is truly the best life you could live,” she addressed the crowd with. “Every single person in this room has the ability to change another person’s life, and I think you’re going to go out and do it.”

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