Representation and Equity: Inspiration from Reese Witherspoon

This episode features a woman whose talent has no limitations: award-winning actress, entrepreneur, producer, women’s advocate, and New York Times bestselling author Reese Witherspoon!

Over the years, we’ve had the chance to see her shine on screen, as a producer behind the curtain, as an entrepreneur, and today in conversation with award-winning journalist Lisa Ling.

We will explore what Reese is doing to elevate women’s stories, change the narrative for women and help chart a new path forward. Part actionable tips and part inspiration, you will walk away empowered to navigate your career, take risks and find your purpose.

This conversation was originally recorded at the December 2022 Massachusetts Conference for Women.

This episode of Women Amplified is proudly sponsored by Cisco.

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Reese Witherspoon & Lisa Ling Episode Transcript

Ling:

Well, I just want to launch into things because we all know that you are a hugely successful actress and producer and entrepreneur, and those things don’t always go hand-in-hand. Not all incredibly successful Hollywood actresses are also successful entrepreneurs. So I want to just ask you what you think the Reese Witherspoon secret sauce is? What are some of the essential qualities that you think have contributed to your success?

Reese Witherspoon:

Well, first of all, thank you for saying that. If I think really about my early beginnings and where my motivation comes from, I definitely think, I grew up in a military family, so there was very much a sensibility, a sense of duty, of giving back. You know, about being on time and being professional and being responsible to people. So that was a really good early foundation for me. And also, my mother was a nurse for 40 years and an educator at a university. And her dedication to her job, her love and passion for her job, really ignited in me this work ethic that I think has stayed with me through the years.

Lisa Ling:

So you would say work ethic has probably been the driver behind all of it?

Reese Witherspoon:

For sure. And I think also a passion for what I do. Even from when I was a really little girl, five years old, my grandmother taught me to read. She was a schoolteacher. And she would read to me and put me in her lap and read all the different voices of each character in a book. And I fell so deeply into this love of literature that has been a lifelong passion for me that I’ve kind of figured out how to use that passion for literature to make change in the Hollywood and media landscape by just talking about books championing female authors, and also turning some of those books into movies and television shows.

Lisa Ling:

Well, I do love your book club. I just picked up Celeste Ng’s new book per your recommendation, so.

Reese Witherspoon:

It’s so good.

Lisa Ling:

I’m very excited about that. But I want to stay on this topic of success and entrepreneurship just for another moment because a studio head once told you that without any embarrassment, “We have a movie with a woman at the center of it, but we’re not going to make two this year.” And what you did in response to that is pretty legendary. You made Wild and Gone Girl, two hugely successful films that put women’s stories at the center. So how would you say you’ve turned being underestimated into an advantage?

Reese Witherspoon:

At first, I was really upset and I told everybody who would listen that I’d not met just her, but actually seven different studio heads who all basically told me the same thing, that they weren’t developing anything for women at the center of the story and that they were happy to buy anything I brought to them, but that I would need to do my own development. So I decided to self-fund my first iteration of my company, and the first two books I bought were Wildand Gone Girl. Because they really spoke to a different kind of woman that I hadn’t seen on film.

First of all, Wild is a beautiful memoir written by Cheryl Strayed about a woman after the death of her mother, walks a thousand miles on the PCT. And for me, that was about this incredible connection women have with nature that we don’t normally see on film. And we see so many man versus wild movies, but I had to rack my brain to think of one movie where a woman is in the wilderness by herself. And so it was really important for me to make that film. It was also really a big deal that I put my own money into it and I put my own time and effort and energy, and it really ended up changing my entire career. That year we did Gone Girl and Wild and we ended up getting three Oscar nominations, and then the next year we were making Big Little Lies. And the ball started rolling from there.

Lisa Ling:

Did that scare you though when you were told we’re only going to make one film with a woman at the center? Did that intimidate you at all?

Reese Witherspoon:

No, it made me mad. I got really mad. And I think naturally, I’m a problem solver. I’m not a big complainer. So I found myself complaining about the problem in Hollywood and the lack of roles and the lack of development. And I thought, “Instead of complaining about this, I’ve got to do something about this.” And as any entrepreneur out there knows, there’s sweat equity, but there’s also real equity. And so I decided to put, the cardinal rule in Hollywood is, “Do not put your own money into movies.” And I broke it. And I thought, “If the studios aren’t going to develop complicated, interesting female characters, I will spend my own money doing it.” Because it’s that important to me.

Lisa Ling:

And speaking of life as an entrepreneur, I just wonder what lessons you’ve learned that you can help any women succeed in any field. I mean, the theme of this event is reset, renew, reconnect. And so I wonder how becoming an entrepreneur reset your career or renewed your ambitions?

Reese Witherspoon:

Yeah. Well, I want to say something that I think is really important. I didn’t go to business school. I just was a hardworking woman inside of an industry for 20 years. But I didn’t sit in boardrooms. I was never an executive. I didn’t know how to raise capital. Those are all things that I had to learn with the help of other people who were very generous.

But one thing that I really learned that was super important was instead of feeling intimidated by people using acronyms that I didn’t understand, like ROI or EBITDA, I said to them, I would say, “I’m so sorry. I’m going to stop you. What do you mean by that?” It’s refreshing to not know something and also admit that you don’t know something. And people are so happy that you’re curious about things. So I’m always ready to take a call too from a budding entrepreneur or someone who’s a young professional, because I always say to them, “If you don’t understand what’s going on, stop and ask very thoughtful questions. Your curiosity will guide you to greater relationships and better success.”

Lisa Ling:

Reese, that’s such important advice. I mean, I think we as women are very often so afraid of being perceived as not knowing or being perceived as a failure in any way. And we wear that idea of being a superwoman or a supermom sort of as a badge on our sleeve. But if you don’t know something, you have to learn somehow, and I don’t think that people ever become offended or think any less of you if you just simply ask.

Reese Witherspoon:

I was very lucky to be surrounded by incredible executives and people who are very patient with me. And I think there’s a lot of women who don’t have access to business school and don’t have those same relationships where they’re naturally networking with people who are using the same vernacular. And it’s a vernacular. You can learn it. Any industry that you’re entering, you can learn it. You just have to pay attention, Google a bunch of things all the time, and stay on top of it. You can also say to people, “Hey, what newsletter do you read every morning about our industry?” I also encourage young people know everything about your business, know how you market things, know how they make money, how do you lose money? What are the biggest points of vulnerability? How can you be of the greatest benefit to your organization, whether you are the founder or you’re just working inside of it.

Lisa Ling:

I want to ask you about another one of your businesses. In 2015, you started the Draper James clothing line, which you named after your grandparents. So tell us about their influence on you.

Reese Witherspoon:

Well, I always think I was so lucky to have grandparents who raised me because my parents were very busy working professionals, and I had grandparents who could pick me up after school and took time to do my homework with me and my brother and have dinner with them. And it wasn’t just about the work that we did together, but it was about the values that they instilled in me to care about their neighbors. My grandfather was a big, Big Brothers Big Sisters organization. He was always doing work with scholarships and helping out underserved communities. So that was a big inspiration to me. And my grandmother was just a voracious reader and always endlessly curious about the world. So I would say those are the biggest influences of my life. Just they taught me how to treat people with kindness.

Lisa Ling:

Wow. I mean, so much of your career really seems like it’s been kind of an homage to them.

Reese Witherspoon:

For sure. And I think a lot about the women that came before me, about my grandmother who, she graduated with a degree, a master’s degree in education, and she was very limited in her opportunities to work. And I think about the women who haven’t had the kind of opportunities that I’ve had, and it really means a lot to me that I do the most with these opportunities I have as an American woman, as an entrepreneur, as a woman inside of an industry to really change the industries we are in to help the next generation. I think about it a lot.

Lisa Ling:

That’s powerful. Well, a year after founding Draper James, you co-founded Hello Sunshine, which is an immensely successful media company, which is focused on changing how women are seen in the media. Basically you set out to help women take charge of their own stories. Why was that so imperative for you to want to do, empower women in this way?

Reese Witherspoon:

Well, I saw from years, I’d probably been in the movie business 20 years at that point, and I saw this real lack of female authorship. Not a lot of female directors, not a lot of screenwriters, and no pipeline being created to bring them into the mainstream of our business. So I thought if I am going to take a chance, and I went and raised capital to start this business, I really wanted to make sure that we were addressing where audiences were.

It was also a time when streaming was emerging and social media was proliferating like crazy. So I was seeing all these incredible creators self-publishing, but Hollywood sort of not noticing. So I thought if I can address where, having a real diverse media company, not just film and television, but social media, podcasts, trying to reach women where they are instead of expecting them to come to me, I think that’s what really gave us an advantage because we were reading books. I mean, I was reading so many books, Lisa, I was like books and books and scripts and scripts just to start that idea that women should be the authors of their own stories. There’s no reason why we can’t be putting them behind the camera and in front of the camera. You get a better, wider experience of what it means to be a woman on this planet right this minute when you have women telling those stories.

Lisa Ling:

And it is incredible how the market has really opened up so much just given all of the different platforms on which people can tell their stories. I mean, there are just so many more outlets available.

Reese Witherspoon:

Totally. And I love looking at Instagram reels and trying to find talent and looking on TikTok. And it’s great to see that you can be the captain of your own ship and really drive your own career now. There’s all these tools available to you, and I really want to encourage more women to take what’s available to them and use it to their advantage.

Lisa Ling:

Well, as you say, the power of women’s stories is just so important, not just on the screen, but in our own individual lives. And what have you learned that women might find helpful as storytellers of their own lives, of their own narratives?

Reese Witherspoon:

It’s so interesting. I was just talking to a friend about this, about self-expression. So self-expression doesn’t necessarily mean that you have to write a book. You can write an article that you can publish on Substack, you can change your social media profile to be more in tune and in line with the integrity of who you are, whether that’s you’re a small business owner or you are an activist and you want to talk about things that are important to you and you’re passionate about.

I’m very good friends with Sara Blakely, who started Spanx, and I said, “Sara, how many times have you told the origin story of Spanx?” She goes, “Reese, I have told it 5,000 times, but every time it makes me so happy because I see that it reaches a new person.” So never stop telling the story of what you’re passionate about or why you’re doing something in your workplace because people are really listening, and particularly people who look up to you or are looking for their own motivation. Some people are just a little bit lost, and it’s good to hear why certain people pivot in their careers, maybe take on a second different aspect of their life. I always look for inspiration in other people’s actions.

Lisa Ling:

Well, and these days we are all looking and craving and really yearning for inspiration. So that idea of being able to again, get it out there and share it with others, it’s inevitable that it will be received well, I think. So getting back to Hello Sunshine, because that company has been so much of what you are about, it puts women at the center of every story. And so how does that mission inspire how you lead and how would you describe the culture of where you lead?

Reese Witherspoon:

Well, I think Hello Sunshine is, it was just born out of this passion for really kind of trying to change Hollywood. The way I found Hollywood was not a place I’d want my daughter to work, not a place I’d want anyone else’s daughter to work. So I knew I had to do something to create safer work environments, a place where women had the opportunity to ascend and be in leadership positions.

And I think for me, it was a real pivot from being an actress for hire and waiting for scripts to come to me and waiting for directors to call me to be more entrepreneurial and going, “Okay, I’m going to invest my own money. I’m going to option some of these books, and then I’m going to have to bust my tail to get them made.” And I’ll call everybody. I mean, I will call anybody. And I will also, I always say, “I’m my own lottery ticket.” I will always bet on me because I will show up, I will do the work, I’ll do the extra work and, yeah, I’ll do whatever it takes to get the job done because I’m that passionate about it. My purpose lines up with my work. So I think that was a really big moment for me when I turned about 34 that I wanted to have purpose in my work.

Lisa Ling:

Yeah, that’s beautiful. This conference or all of these conferences for women, they’re really about community rooted in women supporting other women. So tell us about your own community of women and how you support each other.

Reese Witherspoon:

Oh my gosh, I have an amazing, first of all, I have the best friends in the whole world who have been my friends forever, who’ve always encouraged me. And I’m so lucky that I can have a soft place to land when I don’t have great days. I have the ability to let out my frustrations. Because it is, it’s hard running companies and being a mom and being a wife, and it’s a lot. So it’s important to have those kind of relationships.

And also, I have a handful of female entrepreneurs who I’m friends with. Candace Nelson is a friend of mine who has a book coming out about being an entrepreneur. She started Sprinkles Cupcakes and she was on Sugar Rush on Netflix. She and I talk a lot about what it takes to be an entrepreneur and that you can’t do it alone. You have to have other people around you with different skill sets that actually pick up where you leave off or fill in the blank spaces because it’s simply not possible to be a one man band and run a successful business.

So it’s really helpful to have either women around me who I can go, “What’s going on with your business right now? Okay, are we going into a recession? How’s that affecting you? What did the pandemic do for you culturally? What are your work from home rules?” Things like that. As people are instating new policies, really trying to pick other people’s brains about how they’re handling things.

Lisa Ling:

Do you think that women leaders bring something different to the table?

Reese Witherspoon:

Oh, certainly. I mean, I think by nature, women and men lead differently. We share leadership at our company, so there’s not a feeling of one person has to be in charge and speak over everybody, it’s sort of a very equal leadership across each one of our key executives that sits over every vertical really has an opportunity to speak in every staff meeting. We also make sure that SVPs and VPs get to speak. Sometimes creative executives get to speak, and we get to hang out with the interns too because we have a really robust intern program. Because we really want to show people that even if they come for a while, that this is these skills they can be carried into the world and that women are incredibly diverse leaders. I just think by nature we bring something different to the table.

Lisa Ling:

Definitely. Well, last year you sold Hello Sunshine for 900 million dollars while joining the board and continuing to run the company, and that really cemented your place as one of Hollywood’s most successful entrepreneurs. So how have your thoughts on the idea of success changed over the years and what does that term or that notion of success mean to you?

Reese Witherspoon:

That’s such a good question. I ask a lot of my partners and anyone I start work with, I say, “What is the measure of success? Before we begin, what would be the best result of this?” And for me, I think it’s a mix. So we definitely want to be financially successful. We want every project to do really well, but each project has its own measure. So I would say there are certain projects that we do because the story is so important, we want to get it out there, but it isn’t necessarily like we’re expecting a huge economic return. So we try to level set for each project that we have and try to obviously have a fiduciary responsibility to our investors, but also the importance of who we are as a company, as a brand, how we show up as a brand to consumers, that they trust us, that we are making decisions that are aligned with our integrity is really important to me.

Lisa Ling:

Well, along those lines, would you consider yourself a big risk-taker? And how do you calculate risk?

Reese Witherspoon:

I would say I am a risk-taker, a very thoughtful, pragmatic risk-taker. So I am willing to take chances, and I have certainly had my failures. I’ve certainly thought, “Oh my gosh, this movie’s such a great idea. I can’t wait to do it.” And it did not end up well. So I learned from each one of those. I don’t call them failures either. They’re not really failures. It was just a, I don’t know, an attempt at something that just didn’t work out. But I always learned something from it. And I always try and after I lick my wounds and go, “Okay, well everybody hated that movie,” or, “That TV show didn’t work.” Go, okay, “Why? Why did people not show up for that?” And so I try to get analytical about it and I try to do sort of a forensic study of each thing, and then we go back and we regroup with the whole team and say, “Why do you think this didn’t work? Oh, okay. All right. I see that.” And so we are always trying to learn more to do better.

Lisa Ling:

Reese, a couple of minutes ago you said that injecting or infusing joy into your businesses and into your work is really important, especially during these times. What do you think people are receiving from that effort on your part to want to bring joy? How do you think that that initiative is impacting people in our culture during these confusing, unpredictable times?

Reese Witherspoon:

Yeah. Well, first of all, I feel so fortunate that I get to go out in the world and talk about positivity and movies that are not about people murdering each other. It might have a plot, but it’s like, I don’t know, we don’t swim in the dark lane, I will say, which is nice.

But I think one thing that’s been a big initiative for us this coming year is actually romance. Because I read this article that in ignited this idea for me probably two or three years ago that said, most of what we learn about interpersonal relationships and romance is from movies and television shows. And the lack of seeing that has actually deeply impacted how young people express their thoughts and feelings with each other romantically. And older people too, because it’s a lot of modeling that we don’t see in our real lives. How do you ask a girl out? How do you break up with someone? So we really pivoted into romance this year. So we have two romantic movies coming out and one extremely romantic television show and another show that’s all about love and loss. And I’m really excited to see how audiences respond to that. Because I think it’s important that you’re putting work in the world that inspires people to have more conversation, I think.

Lisa Ling:

I love that. Reese, you’re so right. We are seeing romance and affection, tenderness, love modeled so far less frequently, so much more infrequently, because so many of us are communicating on devices and seeking validation by people we don’t even know by way of social media. And so where are we seeing those beautiful, healthy relationships that give you goosebumps? It seems like it’s increasingly fewer and fewer.

Reese Witherspoon:

And look, I think there’s a lot of, as I speak to younger people now, they’re tired of the phone taking up all their attention and wanting to have more community. I mean, it’s an intrinsic part of being a human is you just want to connect over something. One of our authors, Eve Rodsky, wrote a amazing book called Unicorn Space about finding something to do with your life that isn’t about being a parent or working that is uniquely you. Whether it’s hiking, photography, art classes, going to a dance class once a month. It’s so important to cultivate what makes you unique. Because I think sitting there and looking at device, trust me, I’m so addicted to my device. I am not one to preach to anybody about it. But I do think there’s something to be said about curating your own life and not having an algorithm tell you what your taste is or what you want to do with your day, but actually getting out in the world and into a community where you have to show up and be responsible, but also have some joy and fun. It’s a great concept.

Lisa Ling:

Okay. I’m going to put you on the spot talking about romance. Are we going to see you in the romantic lead in some of these projects? And I know you have a beautiful relationship with your husband, but are there any actors out there that you kind of would love to be in a romantic comedy or film with?

Reese Witherspoon:

Oh my gosh. Well, I’m so excited because I do have a movie coming on February with Ashton Kutcher and it’s coming on Netflix and it’s called Your Place or Mine, and it’s written by this amazing female writer director who did Devil Wears Prada and Crazy Ex-Girlfriend, and she’s so funny. Her name is Aline Brosh McKenna, and the movie is just beyond charming, and it was a delight to work with Ashton, and I’d never worked with him before. So it was really fun. And it’s coming out February 10th on Netflix.

Lisa Ling:

Well, Reese, beyond being a phenomenally talented actress, your drive and your passion are just so palpable. So we congratulate you on all your success. Thank you for sharing your wisdom with all of us..

Reese Witherspoon:

Thank you so much. It’s so nice to talk to you, and thank you for your very thoughtful questions.