Reese Witherspoon: Don’t Let Anyone Control You With Money | Aspire with Emma Grede

Reese Witherspoon: Don’t Let Anyone Control You With Money | Aspire with Emma Grede

I do not know a woman who doesn’t have a disaster financial story. Don’t ever let somebody control you with money. Reese Witherspoon may be known as America’s sweetheart, but behind the scenes, she’s rewriting what power looks like for women. And funny enough, she’s already come up in conversation. Have you talked to Reese Witherspoon yet? Talk to her about money. She isn’t afraid to lean in in a way that so many men are taught to and women are not. Tracy was right. For Reese, money isn’t just about wealth. It’s about independence. And if you’ve ever wanted to be in more control of your own life, this episode is for you. My question to you is whether or not you pivoted out of necessity or ambition. I didn’t believe it would happen, but I was like, I’ll die trying. She decided to pivot and start something totally new. I saw Whites Space, so I decided to do it myself. Reseil company, sold it for nearly a billion dollars, and she’s just getting started. I’m my own best lottery ticket. I know I will pay off. Is there any part of you that wishes that you’d kept full control of the company? I had this moment that changed everything. I’m really excited to speak to you today for so many reasons, but the first one is that you know we all watched you and your career and you are like America’s sweetheart, but you have done such a transition and such a pivot. And so for this particular audience, I’m excited to talk to you about I don’t know whether we want to call it your second chapter, third chapter, what it is, but Reese the businesswoman because you have been wildly successful. And I guess my first question to you is whether or not you pivoted out of necessity or ambition. I think both. I think I uh saw white space and I also was driven by a passion for storytelling and I also had a little girl that I really saw this sudden dir of storytelling for women with the complexity that really represented all women. and I just wasn’t seeing Hollywood step up and develop those stories. So, I decided to do it myself clearly and you really did do it. So, will you just talk a little bit for people that don’t know um about the genesis of Hello Sunshine like because you obviously had a production company before that and you decided that you would you know turn yourself into a media mogul. So, let’s talk a little bit about the difference between the two and what made you actually start where did what was that white space that you saw? Yeah, sure. I um I started my career in Hollywood when I was 14 years old. I did my very first movie. I was one of those lucky lightning strike moments where I went to audition in Nashville, Tennessee uh for a movie and I ended up getting the lead. So, it was just one of those rare opportunities, but I was also prepared, right? So, I’d done two years of acting classes and my career just took off from there. Um I made probably seven movies before I even went to college. Um, I ended up going to Stanford for a year, but I ended up dropping out and just mainly because I couldn’t afford the tuition. Wow. Um, I decided to just really throw my shoulder into acting and I started working a ton. So, for the first, I would say 20 years of my career, I was an actress, an actress for hire. I didn’t really produce. I didn’t write anything. I didn’t come up with original characters. Um, and then probably when I was about 34, well I will say when I was about when I when Legally Blind came out, I got a production deal from Universal Studios for three years. They paid for everything and I made zero movies. I was 24 years old. I didn’t understand. I also didn’t know what stories I wanted to tell. I had a great team. I just I wasn’t I didn’t have intention. And so then when I be I mean you were 24. I was 24. I I hadn’t lived enough of life to understand where the gaps were in the market. I didn’t understand my business that well. Um and so I really for the next 10 years I was a mom. I was a working actress. Um working at a really high level with every studio head in town. Had great relationships. Um, and we’re, you know, talking 70our weeks and long producing schedules and long marketing schedules. And I just I showed up and I was a good worker, you know, and um and I was known as a really good worker. And then when I was about 34, I had this moment that changed everything, which was reading this script. I read the script and it had a guy as a lead and it had two female leads and the women just supported the guy and it was all these crass jokes and I thought it was awful. And they said, so I called my agent. I said, “Well, I’m not I’m not doing this. This is going to set women back.” And she said, “Every actress in town wants these two parts.” And it was this huge moment for me where I was like, “This is what you have to offer.” First of all, not just the actresses, but the women in the world. these this is how you want to showcase women in the world. I was disgusted. I was angry. So I went on a campaign a listening tour listening tour and I you know called on my studio head friends and say hey can I sit down with you? I just want to hear what you’re developing for women at your studio and going to see every head of every studio all seven of them. Only one was developing a woman a female lead in a movie. Wow. And they said they said to me, “We have one movie that’s starring a woman this year. We can’t have two.” Okay. Yeah. Even though we’re and this is not we’re not going back like 50 years here. We’re talking 10 years ago. This was 2011, right? Yeah. 2011. And I was like, “Wow, this is just some this is not acceptable.” It was It was Yeah, it was mindbending. But it’s interesting to me that you took that as fuel to start something because I feel like there are so many people that either take what’s on the table or they sit with the rejection. Not everybody goes like, “Well, I can do something with this.” And I wonder what you would say to other ambitious women about starting a company. Okay. I think this was a a moment, too, because I did the wrong thing first. Mhm. First, I just complained and I keep kept illuminating the problem to everybody who would listen. All my really fierce, amazing friends, and I would say, “Well, you know, there’s this issue. They’re they’re not making enough content for us.” And it was all this stuff about DVD sales had dropped out of the market and, you know, the the cost for development had gone up and they were like, “Well, you know, I don’t know how to solve it. It’s a systematic problem. Um, leave it alone.” Yeah. Well, and I complained about it and then I I had this kind of aha moment where I was like, “Okay, I can either admire the problem. I’m giving it a lot of attention or I can come up with a solution to fix it.” And that was everything for me. So, for the next six months, all I did pen to paper said, “What can I do about it?” And also, I’m I’m the one complaining about this problem. I’m gonna if I think I’m gonna fix it, I’m gonna put my mouth my money where my mouth is and I’m gonna invest in myself because I’m my own best lottery ticket. I know I will pay off. You know, you’re like, I can make this work. And were you that certain about it from the beginning? Were you like, I’m going to build a billion dollar company cuz I know I can bet on myself. I knew I never thought I was going to be a billion dollar $900 million. I never never never. I was like, no. I just knew I was going to solve a problem. I knew I read more books than a lot of other people. I knew I read super fast. I had a market advantage. So, you were much more mission focused. You were like, “Here’s a white space. Here’s a huge problem. I’m going to solve the problem.” Not like, “I’m going to build wealth for myself. I’m going to start a media company.” No, that wasn’t my intention. My intention was create more stories for women, create more opportunities for different kinds of women to have the opportunity to tell their story. M. And then the other part, I haven’t really ever talked about this publicly, but it was me sort of wrestling with this fame dynamic. Oh, yeah. Where I was getting all this attention, but I didn’t want any of it. And I thought, how can I take that and use all of that energy that’s coming at me and point it towards another woman? Oh, yes. Who is working her ass off and deserves that attention. And it really worked, right? I mean, for for for your little idea to turn into not just this company, but a movement in the entertainment business, like there has been a seismic shift. I’m not saying everything has, you know, it’s solved and it’s all done, but there has been a seismic shift. And I think so much of that is owing to what you did and you being really loud and purposeful about what you were trying to build. Don’t you think? Well, it was definitely loud about Yeah, but you were because I feel like we all knew you were on a mission. Like anybody that read about Hello Sunshine, it wasn’t like Risa started a media company. It was like here’s this giant problem and here’s what she’s doing to solve it. And it was very clear that there was like this was a purposebuilt company. And even as you were like attracting staff and bringing people on, it was like ooh ooh everybody everything felt like it was like like chess. Like it was like this is what we’re doing. This is what we set out to do. Yeah. Well, it was very intentional. I think back to your point, I was really clear on the mission. Yeah. And the mission was also we were we were really fueled by this digital transformation right so suddenly everything went to social media platforms YouTube I was noticing marketing was shifting on my movies we’d have completely different marketing meetings and we’d sit in traditional marketing meetings they did not understand social media I mean it was just wildly clear and I thought this is a gap I can I can bridge so that wasn’t something that was scary to you like every you know because if you start in the business when you’re 14 there’s a tried and tested way that you’ve been successful you actually saw it as an opportunity as rather than a threat to to your business. Yes. I always look at technology in the future as not like oh god it’s going to make me obsolete. I look I say how can I harness it and teach other women how to harness it to create my business or push us all forward collect. So you’re not shaking in your boots at at AI now? No, I’m pausing because there’s some stuff recently that’s really it’s Yeah, you know, it’s giving us pause. It’s giving us pause. Yeah. And we don’t have any regulation and we we will we’ll get there. There’s not enough policy around certain things, but I’m not scared. Well, there’s certain things you can’t fight, right? I feel like it’s like how do we embrace it? How do we come together? How do we, you know, one and one has got to equal three at some point, but it’s not going to work to to shun what’s happening. Well, also when streaming started, it was really clear that the best content on streaming was long form television, a lot of shows, binging and a lot of I think traditional movie stars were reticent to go into a new format because we all came up hearing don’t do TV, don’t do TV. TV is the the second, you know, that’s our it’s like a step down. Yeah, it’s a step down. Once you go to TV, you’ll never come back to movies. And I I was like, you know what? No, I don’t agree. I think we’re all watch we’re all moving towards a new reality. I was also watching my teenage children not go to the movies anymore. That that’ll show you. You have to look at those patterns and what’s happening. I’m like, my kids don’t even know the t where the TV is. No. At home, they live on a device. They live on YouTube. Yeah. We have one TV in our house. We used to have one in every totally. and you wanted a big TV where I come from it was like we want a giant thing that takes up the whole room. Now it’s like no thank you which is kind of lovely for the house in a way kind of romantic better lines. It’s really really true. Um you have such a like this well this is how I see you but you have such a personality type that is synonymous with you. I said America’s sweetheart but you kind of look at you and you’re like this woman is so wonderful and so sweet and so sort of the earth. So when you made this transition, Yeah. do you think people took you seriously? Like do do you think people saw you coming? No. No. I think people knew I was a hard worker, but I don’t think and I will tell you it wasn’t successful right out of the gate. Talk about that. Please tell me tell me more. When I started the company, I was in this like um little almost rundown office building because I was self-funding and I had two employees. You really you selfunded from the beginning. So, it was actually you were truly taking a bet on yourself with your own money. Yep. And I decided I had this producing partner and we decided to option two books. Our first two books were Wild and Gone Girl. And so, one they were your first two books. Yes. Shut up. And I read it in galleys before it was pill. But they just both hit number one probably six months later. That’s crazy. And I thought, “Oh crap, I’m really good at this.” I would have been like, “Yep, that’s me.” But then I had to turn him into movies and that’s a whole other thing. It’s like, it’s great to have potential. It’s great to get that star, but what are you going to do with that? So, I knew I had to execute at a very, very high level. And so then we did, we executed a very high level and we got three Oscar nominations for three different women. It made combined $600 million in box office. And I could not keep the lights on in my company. Oh. Oh. Even post Big Little Lies. I was doing Big Little Lies and I was like, the numbers aren’t mathing out here. I can’t have So, we went up to four employees. I wanted to give them all health insurance. I wanted to make sure it was a great working experience for them. And I’m not talking I had fancy offices. I had three offices in Beverly Hills. I mean, that’s a nice area, but they weren’t nice by any means. And I it just wasn’t mapping out. And what was that? Because I I wanted to talk to you about the fact that you brought a CE a CEO into your company from the beginning, which again, a lot of people feel like they have to they started a company, they founded something, they need to be the CEO. But you didn’t do that. So tell talk to me a little bit about that timing. You’re you’re making all of these waves. You’re doing the important work. you’re actually meeting your mission and your purpose, but you’re not making any money. And that bothered you, obviously, cuz again, for some people, they’re like, “Well, as long as I get this piece over here, that doesn’t matter.” Yeah. No, I I No. No. I was like, “Wait.” So, so then I dug in again and I met with my friend who, you know, who ran a venture um fund and he and I started talking about it and he was like, “Well, what do you own of these shows?” I was like, “Nothing.” And he said, “Well, how do you get to ownership?” And I said, “Well, that’s the magic key, kid.” You know, actors historically don’t own any of their characters. I don’t own El Woods. I don’t own Tracy Flick. I I don’t own any of these characters. Um, and so he said, “Okay, well, let’s put put our heads down and feel like this is a really interesting time where studios, streaming studios, need you more than you need them.” And I said, “You’re right.” I He said, “I think we could drive some really crazy deals.” And so he and I got together and put together a business plan. And I was like, really? I’m going to ask them for these things that are breaking precedent. And he was like, “Yeah, you are. You’re you. And you bring now you have social media followers. You’re going to bring this marketing component, too. You have you’re not the average producer, so you’re not going to get the average producer deal.” Um, and could you absorb that? Could you take that in and go like, “Yeah, I’m going to run with that.” What he said? I mean, I didn’t believe it would happen. But I was like, I’ll I’ll die trying. Yeah, that’s actually, you know, why not? Why not ask? All they can say is no. Um, and then I won’t go work for them. I’ll take it. The other advantage I had was I would get a book and I kne I had a really good taste for what would be popular, not what would make you smarter or what. Where’d you get that from? reading so many books as a child, so many books as a young adult, so many books as a young woman and a mom that I was like, “That one’s gonna be really popular. I just know.” And also, so we had this, it was like this flywheel where I could pick a book, take attach a piece of talent, let’s just say like Little Fires Everywhere. I I said, “Call Carrie Washington and say, “I’ve always wanted to work with you. You and I are going to be producers. we’re going to star in it together and we’re going to work for ourselves and we’re going to drive this like really great producing deal. She’s like, “Yes, please.” Thank you. She’s like, “Let’s do it. Let’s do it.” Yeah. And so then we go to market, we call these seven studios and we say, “Which one of you wants it?” And it’s a bidding war. So we’d say, “Okay, and also you’re going to break precedent and have we’re going to have terms that you’ve never agreed to before.” And that’s what we did. And it just we did it again. And then we did it again. And we did it again. And we created enterprise value for this company because we’re building a library. I mean, you know, at the same time as building the social media and and the brand and um brand partnerships with different, you know, great blue chip brands. Is is that indicative of what business Ree is like? Like somebody that isn’t fearful and unashamedly goes after what she wants? Um, I’ll tell you. I know what I know what I know and I know what I don’t know. And I’m really I have zero ego about saying, “I’m going to stop you. I don’t know what you’re talking about. Can you explain it to me?” So important. So, I feel like a again, a lot of women don’t feel comfortable to do that. And I think it’s one of the things that we have to learn that it’s all right if you don’t know. And trying to fake it is not helpful to anyone. Fake it. You’re going to get yourself in deep mud. Yeah. Yeah. Yeah. Deep mud. And And so I would turn to my CEO, Sarah Harden, and I’d go, “Oh, I love Sarah Harden.” Is that Sarah Harden? Yeah. She’s a G. And she had sold all these digital businesses that had male founders. And this was the first time she’d been approached by a woman who was like, I want to do what you just did for seven different companies. Let’s do that. Yeah. And she was like, great. I love to read. I love storytelling. and she um but she kind of coached me for the first two years of our company. I didn’t know anything. I did not go to business school. But how smart of you to bring somebody in that did because I remember reading this amazing thing and I I don’t remember if it was Charlie Manga or um I think it was Charlie, but it was like well how how are you guys so good at finding the right people to run your companies? in his head, we look for someone who’s done exactly the same job somewhere else and been w wild wildly successful. I’m like, yeah, duh. It sounds so simple, but again, it’s like if you want to be successful, and I love this fact that you bought people in that you could learn from, right? She taught you what you didn’t know, and you were smart enough to know what you didn’t know. And so, it says a lot about you as a person that you can surround yourself with people like that, but you don’t feel threatened, right? And she didn’t feel threatened by me. And we we had a real nice match of skill set. I’m a real creative so I can sprinkle magic on things or I’m an enthusiast too like you. I could tell totally. You have to be. You’re going to sell ice to Eskimos, Emma. I like to think so. Rece I’m like seriously I don’t know what’s happening, what you’re selling me, but I’m buying it. I’m like let’s do it. What do we got? Let’s just do it. Yes, let’s do it. Let’s do it. Um but I’m that way. And Sarah’s like, “Okay, we can accomplish one of those five ideas, race, but we’re not gonna do all five this week.” Yeah. Okay. Because my brain just gets excited about the possibility, of course. And so, um, but you need somebody there to to to talk to you about business readiness. And a business can only do great things when it’s ready to do those great things, right? So you’ve got to be, you know, you can throw all the ideas you want out, but the acceptance rate is not always going to be there. And so it’s so important to have that person beside you and to know you need that person beside you so that they can say, “It’s time for this thing now. That’s great, but maybe park it for a second.” Yeah. Yeah. And I think that’s good. I needed her to keep the trains on the tracks and then also to get me to slow down, slow it down, do one thing well, then we’re going to add on another. Then she always say crawl, walk, run. Yeah. Yeah. Which was really helpful. It’s like a little traffic light system. Cuz I want to bolt. Yeah. Through everything, which I just love about you. I’ve always believed that the soul of a neighborhood isn’t in the buildings or the skyline. It’s in the people. The way your barista remembers your coffee order. The neighbor who waves every morning. The local bakery that knows your kid’s favorite muffin. That’s what makes a place feel like home. For me, our neighborhood is like this living scrapbook of memories. There’s the farmers market that we visit every Sunday morning, the park where my kids learn to ride their bikes, and the ice cream store where we visit after school to celebrate milestones, big or small. It’s not fancy, it’s familiar, it’s ours. And that’s the beauty of community, right? It’s built through those small acts of connection. A wave, a shared meal, a quick how’s your day that turns into a friendship. It’s this invisible thread that ties us all together. Even in business, I think that the same spirit shows up. The idea that success isn’t about standing alone, but about lifting each other up. That’s why I love what Airbnb represents. Hosting on Airbnb isn’t just about giving someone a bed for the night. 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Join the loyalty program for renters at joinbuilt.com/ma. That’s j o i nb i lt.com/ma. Make sure to use our link so they know that we sent you. So fast forward, you create this incredibly dynamic industry changing company and you end up selling the thing for nearly a billion dollars. So how do you know or how did you know when it was the right time to sell? Okay. Well, timing is everything as you know market shift valuations were really high in 21. It was a really crazy time. media companies had a frothiness about them and I thought this is a good time to bring on a partner. Um, and so we really went into that process. First of all, let me say I was so grateful for my team because I had this vision, but it didn’t work if I didn’t have worldclass executives around me. And I got these women to leave their cushy corporate jobs to do something entrepreneurial. And I said, “I’m gonna give you equity.” And they didn’t know what that meant. That could be a zero. Quite often is. I know. More often than not, but not for you. No. And it And so when we got to the process, another I’m I’m all about intention, right? And knowing what I wanted from that process. I wanted the best result for my employees, my my partners in this who had um had believed in my vision and walked with me. Yeah. towards the school. And then I also wanted women in the world to know that their stories mattered and they are valuable. Women’s stories are valuable. Mission accomplished. And that had never really been emphasized in my lifetime. I mean, it really was. It makes me want to cry. No. Yeah, I could cry because I feel like there’s one thing to set out to try to do something. It’s another thing to do it. It’s another thing to do it and bring everyone along with you. It’s another thing to do it, bring everyone along with you, make them a load of money at the same time. And so, I think kudos to you, Ree, because you’ve done something extraordinary with that company. And I’ve been, you know, in my research reading a lot about you the last the last week or so. Um, and I think it’s really interesting because obviously as you said, you sold at the top of the market. There’s been a lot of news about your partner and some comments that have been made there. And I think it’s kind of interesting because again, you did what was right for you and for your partners and those women that left those cushy jobs. I think about little me starting in this business and going, “Okay, well, the only opportunity really was to be an actress, but I probably would be am more suited to be a producer or a writer or a director.” Why so? I’m a I’m a team builder and I’m not an individual, you know? I’m more of a like let’s all get together and make this. And that wasn’t something that was possible then. Yeah. In 1990 when I started, nobody was talking about female directors. There were no female. There were like three female screenwriters that were successful. Um, when I started in the business, I think it was like 2% of films were directed by women. Yeah. I don’t think you can underestimate that because again there’s so much talk about it now. Um, but it was a very different time then and and and it’s again so much credit has to go to you. But I do think what I love and Shondaanda and Mindy and but but it’s important, you know, you s you you built this company and you sold the company and I just wonder what that feels like. Okay. It feels really good. It does. It felt like um I was able to do something outside the Hollywood system that had historically been closed door to a lot of different people. So if you tried to have ownership, it was a no. If you tried to be a woman in charge, it was a no. If you were a person of color, forget it. Um, so it just felt like it was breaking a lot of barriers. Yeah. And it was also saying there’s a new way to do things. You can also look at things from a different vantage point and use things that you have inherently that maybe like I think of fame as like this. It’s not my favorite part of my life, but I could use it towards my advantage. And you have to. Yeah. Yeah. It made it made so much sense. Is there any part of you that wishes that you’d kept full control of the company? No. No. I’m really happy with um my partnership there. I’m really happy. I’ve had a great It’s been four years now of still working there and still operating and um it’s just been I’ve learned even more after selling it. What do you think you’ve learned since selling the company? Well, definitely reporting structures and all of that stuff that I didn’t understand. And I’m the only person sitting in the board meeting going when they put up the P&L, I’m like, I’m just my brain takes a little nap. I’m going to just stare at the ceiling for a second. And I know that makes me sound like a ditz, but I just know where I’m not additive. And and I think one of the best things my friend Sarah Blakeley always says is like don’t don’t try to be something you’re not. She tried to move into Right. Yeah. Don’t Yeah. They’re not They didn’t hire me to be the CFO. I’m not there to crunch numbers. Absolutely not. And you don’t need to be all things. Like that’s what I learned I think so early in my business journey because I would walk into these board meetings and I’d feel like everything was on me. It’s like no, that’s why you have a CFO. That’s why you have a data person like I am not that and it’s so important to learn to lean into your strengths and I think that all of the great business leaders we know they happen to be really good at a handful of things and the rest you have to outsource it’s totally fine but didn’t you find as you built your companies you you start to absorb it like as osmosis you sit in enough meetings now I feel completely I could sit in your board meeting and know exactly what I’d ask and it it’s it’s taken me time. But now I feel like there’s this feeling of you can’t get in there, right? If you didn’t go to business school, you can’t start a business and you’re never going to be successful and you’re never going to sell it. And it’s just that’s it’s just not true. It’s just not true. Well, that’s partly one of the reasons Sarah Blakeley, Whitney Wolf Herd, and myself, we were all looking at each other one day and we were at one of these conferences. You you know, you were probably there, too. We’re all and we just sat there and we’re like, “Did you go to business school?” She’s like, “No.” Did you go to business school? No. Well, you know what it does? It gives you Listen, I think we all learn really differently. I am a like super dyslexic and I learn very specifically because of that. And so I think that there’s all different routes to take. And one of the main reasons I wanted to start this podcast is to show some of those ways and actually to show the exceptionality that comes from different people and different ways of thinking because it takes all sorts. And so I really just enjoy that. what you bring is going to be very different to what I bring and with there’s room for all of it. Yeah. And I think we need people who are out out of the box thinkers to insert themselves in different ways and and you know and if you look around your company and you don’t have an out of the box thinker, you’re kind of at a disadvantage. Oh, you sure are at a disadvantage. So, we had Tracy Ellis Ross on this show. What a love. I mean, she spoke so highly of you. She said that you give the best money advice. So I was apparently so I was like I’m going to ask her. I am called the treasurer in some groups. I’m like yes. How are we making revenue and how are we allocating it? So what’s the one thing that every woman needs to know about money? Do you think Oh my god. Where do I start? One thing. Well, go on. Give us it all. I’m Well, first of all, I learned about money from doing things wrong. Yes. I don’t know a woman, Emma. I do not know a woman who doesn’t have a disaster financial story in her past facts. Whether it’s her, her best friend, her sister, her mom, her grandma, her auntie. Mhm. She lost all her money or she got divorced and she got stuck with the bill or you know just whatever financial does debt so much debt and so I listen to every podcast on finances. I am so interested in financial wellness for women and just also a lot of what we learn is one course three days in high school. We’re lucky if you get three months. Yeah. And that was the end of my financial learning. And then I became this woman. I was making money and I was a young mom and I did not save correctly. I’m in fine. I’m fine. But what do you mean you’re fine? You’re not like you just like are you not rolling in it like now? Like just like I didn’t I did invest properly. I’m not not saying that it wasn’t I’m completely fine and and and I did well but I could have done amazing if I had learned a few things and a lot of them are mindset right about saving about the steadiness of the stock market and index funds and diversifying your portfolio and making sure that you’re looking at treasuries and you’re looking at bonds and yields and things that are pretty simple if somebody says them to you in A like if you’re a visual person, you see a visual chart. I’m a visual person. So, every time I talk to people about finances, it laid out. I need it laid out and I want cute colors. I’m just being honest. Notes. I want a pleasing palette and a pie chart. Thanks. Damn right. We know what your business managers are doing, making this very aesthetically pleasing presentation. Like, can somebody do the pie chart for Ree? But I love that you say that because it is all pretty simple, but again, we’re not always having those conversations and sharing the information. What’s the best piece of money advice you think you’ve been given? Don’t get into debt. Do everything you can to not get into debt and pay off those credit cards or don’t spend the money like it’s yours. It’s not yours, girlfriend. Yeah. And that was a really good piece of advice. Um, don’t ever let somebody control you with money. Somebody says, “I’ll take care of it and I’ll take care of you and I’ll take care of this.” That person could leave, that person can hurt you. You always keep your job. Your job is your life insurance. My mom used to always say that to me. Oh. And my mom went through some tough stuff in a marriage with finances. Really tough stuff. Yeah. And so did my grandma. Not in the marriage, but in like a family structure. And um I have this past of women not being taken care of financially. And so I think me too, right? And it as a little girl Yeah. scars you like literally it’s living inside me so so deeply and that’s why I have a passion for helping women um understand and also demystifying it, you know. Yeah. I feel like the demystifying piece is really really important. Do you are you the type of person that looks after everything yourself or have you kind of outsourced all of that to a team at this point? I have outsourcing but there’s frequent check-ins. Same. Weekly? I’m the same. I like to have a enough of it. You know, it’s like one hands on it all the time. Like I’m happy to let the experts be experting, but I need to like I need it there. Yes. Yeah. I need it there. And then I also need checks and balances. M I need to diversify things so that everything’s not in one investment or one savings account. Yeah. But that’s it. That comes again I think that comes from your upbringing. It’s like if nobody teaches you that you don’t know and you’re just like okay the money sits all here and it’s safe but it’s like it might be safe but it’s not growing. It’s not doing anything for you. Right. Right. And most people don’t live in a way that savings is even part of their life. Okay. So I’m I’m very realistic about that. Yes. You have to be with my mom and my grandma always saying to me, I don’t have any savings. You know, they did have my mom has retirement because she worked her whole life doing three and four jobs, including being in the military and being a nurse and working at a state university, but you have to think ahead and you have to think about saving as helping your future self. Oh, yes, absolutely. What you don’t spend today, you’re saving for your future self. You’re saving for 65year-old Emma who doesn’t want to have to worry about the gas bill. Yes. Yes. Yeah. I want to relax as an old lady. Yeah. Me, too. Eventually, at some point. No. I want to have a glass of wine and sit on a porch. A porch. I want to come on that porch. We’re just going to sit there and tell our stories. Talk about all the like, you know, we’re going to travel where we want to go. Oh, and our cute joyful. Oh my god. We’re going to have the best time. They could be looking after us. You know that feeling when you finally find the outfit? The one that makes you feel confident, radiant, and like you could walk into any holiday party, like it’s your own personal runway. That’s exactly what Macy’s free personal stylists are here for. Seriously, they can turn sometimes the stressful task of holiday dressing into something fun, festive, and totally personal. 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And so I want to talk to you a little bit about your mindset and also Reese and leadership because you’ve clearly had to be and you’ve become an excellent leader to get to where you you are. Do you have like is there a leadership or a business philosophy that you have? How do you think about how you come into a room, how you lead people, or is it even something that you think about? Um well I I wasn’t always a leader. I was a I was part of a group. I never in high school ran for student office. I never wanted to be the person who raised their hand to run anything. That’s crazy because I think of you so as like like head of the school student president. No, that was just a character I played in a movie once. Oh, damn. Is that where I got that from? I’m not Tracy. I’m not at all. Um, and so when my company came around, I bet I’d had a lot of group dynamics. Filmm is a collaborative um art. So we work with groups of 150 to 200 people per movie and we’re all working in concerts for the same idea. Um and so I knew when I started my company I wanted to have that same feeling but I knew I had to be the director and the director the most successful directors I’ve ever worked with have very clear vision. They also don’t micromanage people who are very good at their jobs. So you hire the best and let them do their thing, but keep reminding people core values. Core values. So it’s really important when you begin your company to do that core values exercise. Ours at Hills and Shine are optimism, humor, storytelling, um a do-it-yourself culture where nobody’s above any one thing or below any one thing. It’s not hierarchical. Um and so they’re defined and we can always go back and they’re on the wall. So, in case you forget, they’re right there. Um, and I I I think one thing I always say, and I said this to my little kids, um, it was it came from motherhood. And you know, when you’re like about to cross the street with your kids, and you’re like, “Okay, walk quickly directly to the door of the grocery store. We’re not wandering around. We’re not walking in circles. We’re not wandering off. Walk directly.” And so, I started saying to my kids when they were little, “Walk with purpose in the direction you’re going.” Wow. And so when I started the company, I extrapolated that out to walk with purpose, right? We’re walking towards a purpose of greater storytelling for women, greater recognition for female filmmakers and artists and authors. But also you start to notice people walk in the same direction with you. Oh yeah. especially when you have purpose and especially when you have that level of clarity because I think one of the biggest jobs that you have as a CEO is to constantly reinforce those values right it’s like you know as companies invariably do hopefully they get bigger more people come on board and you need to be that beacon that tells everybody where we’re going but I heard you well maybe I’ve read in an article that you say you have a bit of a problem with the word power and when I speak to you it’s so clear that you are incredibly powerful and incredibly directional. Do you still have that in you? Power is just a hard word for me to handle because I think for years in Hollywood, I watched p the abuse of power. Oh yeah. And power corrupting and also people assuming power when they hadn’t really done the work to have the power. And I watched a lot of women defer to powerful individuals that didn’t really know what they were doing or talking about. So it’s hard. Power feels like an empty word to me. I think are you more comfortable with leadership? Leadership is a better word, I think. Yeah. I I think we have a lot of great leadership at Hol Sunshine. Starting with you. Starting with me, but my Yeah. My I’m really like I hired a really because great leaders don’t stay around not a great leader. So you have to be basically I’m saying that you are well because you wouldn’t have had that many incredible people in that company if it wasn’t super solid at the top. Yeah. And I’m and I’m very I’m I recognize their efforts and I really try and I hope I do a good job of this of constantly telling them I appreciate them and I appreciate their efforts even if something doesn’t work the right way. I also appreciate when people take accountability for mistakes. I appreciate when people don’t triangulate at a company or talk about another person that we work together on problems, but Emma, I have learned an entire world of information in nine years that I’ve been doing this. Have you? Um, and I have failed. Have I failed? Yeah. Well, I would say, you know, when when I had the company and it I’d done I had three Oscar nominations and eight Emmys for Big Little Lies and I couldn’t do anything but break even. That was a fail. And I thought this there’s something wrong here. What did you do? Well, that’s when I called my friend and and he helped me come up with a business plan. And that’s when I hired Sarah Hard. But have we had fails? Sure. We’ve had some stuff inside the company that I feel like we tried things, didn’t work. Just didn’t what? Certain verticals were doing really well five years ago, not doing as well right now. That’s okay. I’d rather us try. But I’m really proud of the brand that we’ve built because I think it stands for something and consumers know what it means. Oh yes, I do. You say hello sunshine, people like I know what that is. Yeah. I mean, I wouldn’t say everybody, but I would say, you know what’s interesting? I went and um spoke at a business school last year and all the young women ran up to me and they were like, “Oh my god, I love your company. I love your company.” And all the guys were still sitting down. They were like, “What company?” Unless she was an actress. Ah, and you were like, and they were like, “You don’t know about our company?” But a lot of guys don’t know about Hello Sunshine. Well, so in fairness, it it wasn’t made for them. Yeah, it wasn’t. They have everything else. That’s true. But women consume more media than men. Women control more consumer spending. And I thought, we need to do better for women. They need to have better offerings and see themselves in movies and television shows. Um the the other unexpected outcome of the company that I really didn’t know would happen is the financial gain for the authors and that is a big touchstone for me because I’ve had I’ve gotten letters, text messages be like a picture of a key and I’ll say what is that honey? And she’ll say I was able to pay off my mortgage and buy this I own my own home now. Game over. No. One sent me an acceptance letter to a college said, “I paid for my son to go to college. We’re he’s the first kid in my my family to go to college. We’re going to need more tissues.” I mean, is there anything that could make you more proud and happy? I mean, surely not. No, no, no. Absolutely not. And these people are so deserving and just, you know, and the Hellstone Shen has sold over $800 million of books. $800 million of books. I don’t even know where to go. We don’t even make any money off the book sales. What? We don’t make any money off the books. We just Do you want a tissue? No. No, she’s good. Am I going to cry? I’m done crying. Wait a minute. What do you mean you don’t care? Wait a minute. What do you mean you don’t make any money off the books? The book sales? No. So, if we auction the book and turn it into a movie, obviously we do. But I always imagined that you that there’d be some kind of reciprocal backend royalty. No, we just market them and we pick I mean it’s a big deal the whole process picking 12 books a year and we market them and we our whole team is behind it and we have live events and we get people together and book clubs and my big vision was how do we take the book club out of your grandma’s living room? Oh yeah. You sure did it because there’s this great quote by this guy who just won the Pulitzer. His name is Pcel Everett and he said, “I think the most subversive thing you can do right now is belong to a book club because you’re socializing ideas.” Yeah, totally. Absolutely. I mean, listen, I’m a huge reader and it is probably, you know, it’s up there with my biggest pleasures in life to get read. I read so much. The problem with me is that I right now I’m reading on tyranny. So, let’s just But I I go back um I go back to things like over and over again, but I’m kind of eclectic in my book taste. And you know, I just feel like it’s so good for the world that you do that, that you give this like other option to all the media and all the noise that’s out there because there’s something that’s so good for us about when you can like dive into pros and get your head into something that you hold in your hands. I don’t like It’s good for your mental health. It’s good for everything. It’s good for your memory. It’s good to change your neurological system just right before bed. It’s good for your family. 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I want people to know that this didn’t happen when I was 21 or 22 right out of college. It took a long time to figure out how I was going to take all this knowledge about my business and all the relationships I’ve built and pivot into something that was more entrepreneurial that I had an opportunity to start a company at 25 and I I didn’t I didn’t know what I was doing. So sometimes the best things that happen in your life and when you get to boss up is when you’ve actually done the hard work of being every version of every person on set, you know, or in your business. You need to know your business inside and out. You need to know how it makes money, how it loses money, why you’re valuable, why you’re not valuable, how you can add value. Um, if your business is taking a dip, you better know why. What where is the future of your business? where’s it going? Um, so I read a ton and I try to keep up. Right now I’m just buried in AI going what’s happening and I’m talking to people and I’m meeting people who are tons of startups around AI. Um, but you’re going out of your way to immerse yourself so that you can understand. Yeah. And bring that into your business. Yeah. Bring it into my Well, bring it into my business and also help bridge the gap for people whether that’s for consumers or for my like-minded girlfriends who are have their own businesses. We’re all sitting here going, “Okay, what are best practices? Which companies are you using? How do we protect ourselves? Okay, well, how do we harness this for the greater good? How do we do this ethically without putting real artists out of work?” It feels like you’re still super ambitious. Are you? I’m h I don’t know how to not be ambitious. It’s a big part of my identity. How about you, son? Yeah, same. Could you stop? No. I feel like when we’re 65 and on that porch, we’ll be cooking something. You know, it’ll still be going. We’ll be like inventing the new supplements or something that people need. Yeah. Like solving all our almonds. No. And I feel like that’s part of, you know, it’s so much part of my identity at this point. And I look at you and I feel like once you’ve done something, you you know, you’ve you’ve proven to yourself that you can see a problem, you can solve a problem, you can make things so good for everybody around you, like why would you not look at other things? Why would you not continue to be expansive? Like it might be in a different way. It might not necessarily be another company, but you are someone who has really made a big difference. And I don’t understand why you would not want to do that again. Yeah. I also think sometimes there’s a bigger higher purpose to you being that person. You are who you are here. You are meant to be this person right now. You’re you’re meant to be this uh this woman that people look up to and really listen to and you’re fulfilling part of your life purpose. And I think if something else comes my way or I know about it or like I just wrote my first thriller. I never thought I’d write a book. I can’t believe this. They literally told me. I feel like it was just like swooped in there at the last minute. It’s called Gone Before Goodbye. Right. Before Goodbye. I Is this your first book? Yeah, it’s my first book. Exciting. And again, partnering with a master, Harlon Cobin, who is just a incredible thriller writer who’s wrote written 90 million like sold over 90 million books. What made you want to pivot again? Um, first of all, 90 million books. He’s sold so many books. Wow. And he’s really big in so many The book is being published in 22 different countries. That’s not They sent me all the covers. I was like, “What? What?” Um, but I’m really proud of it. Yeah. And it has a great woman at the center of it who is of course it does kind of re I think it’s reinventing the thriller genre and putting like why isn’t there a female James Bond or Jason Bourne? No. Can you think of one? I’m sure there is. But I thought international world and this woman who has this really distinct skill set and I thought I’ve always just come in to be in someone else’s vision. Yeah. Right. My whole creative life and I thought what if I build the whole world? What if you did? Yeah. What if I did? I mean unreal. You’re going to try. We’ll see. I mean how incredible. It really really is incredible what you’ve done and what you’ve built. And I feel like you will inspire an entire generation to think that they can actually do something really, really meaningful and have it make the difference in so many people’s lives. Because when I think about what you’ve done, that’s the most impressive part of it that actually it’s touched so many people and you’ve done it with grace and with intention and you’ve touched people. You’ve entertained us while you’re doing it. You sold it. You made the money. I mean, it’s just like so many great things. But the the best part about it is that people will watch you and go, I could do that. I hope so. I hope there’s so many more Hello Sunshines. I really want some little girl right now to be hearing this podcast and go, I can do that. If Reese can do that, I can do that. Oh, she will. A million% so happy. I love that you’re here. Thank you so much. This has been so nice. like heaven to speak to you because you’re the like least disappointing person on the planet. Wait, do you have disappointing people on your podcast? Well, you know, you run into them every now and again. I’m not going to lie. Oh, maybe not on Aspire with them. Agreed, but you know, not everybody is as cute and sweet as those interviewing people. You’re doing a great job because it’s also a different skill. Oh, it’s a totally different skill. Well, they hate me cuz I don’t do any of what’s on that card. They’re like, that’s not what you’re supposed to say. All right, let’s move on to rapid fire. What is the first thing you do when you wake up? Um, okay. Uh, feed the dog. A and then make coffee and then wake up my son for school. In that order? Yes. I love that. Last thing you do before you go to bed? Kiss my son good night and take a bath and then go to bed. And I read I read in the bath. You read in the bath or I listen to podcasts in the bath. What podcast are you listening to? Inspire with Emma Green. What are you currently aspiring to in your business life to help women bridge this technology gap? We’re in a really interesting time. I want to help women bridge the gap. I think that’s a great and very noble cause. Um, and what about in your personal life? Um, to have hobbies that I don’t turn into businesses. Okay, good luck. I want to know what kind of hobby are you going to have? Well, right now I make chocolates. Oh, that’s gorgeous. It’s really fun. Are we packaging these chocolates or Listen, did I just say now? Emma’s trying to turn. Okay. Sorry. I just took into a business. We put them in a glass shelf. Um with a ribbon or something. I mean, you’re in Nashville, but you got to It’s really fun. No. Amazing. Um what is a book that changed your life? Um so many books changed The Measure of Our Success by Marian Wright Edelman. It’s a beautiful book. And she’s she was this activist who marched with Martin Luther King and she started the children’s defendant. She’s probably the foremost advocate for children’s rights in America and she wrote this letter to her sons on their 18th birthday about how to be a good person. Check it out. It’s powerful. Immediately going to check that out. Yeah. What is something that you valued when you started out that you no longer value? um other people’s acceptance. I mean, it’s nice. It’s nice when people are rooting for you, but it’s okay if they’re not. And what is something that you value deeply now that you didn’t when you first started? Understanding other people’s intentions. You got to know about that. Thank you, my darling. This was excellent. You’re the best. Oh, that was fun. Thank you, Emma. Thanks for joining me on the Aspire podcast. For more strategies on how to build the life of your dreams, be sure to subscribe to our YouTube channel.

Reese Witherspoon may be known as America’s sweetheart — but, behind the scenes, she’s built a billion-dollar empire that changed Hollywood for women everywhere.

In this episode of Aspire, Emma Grede sits down with @ReeseWitherspoon to talk about the moment she stopped waiting for permission, the lessons she learned about money and ownership, and what it really takes to pivot in your career when everything looks successful from the outside — but you know you’re meant for more.

From her first acting gig at 14 to founding Hello Sunshine and selling it for nearly a billion dollars, Reese opens up about:
✨ How to recognize when it’s time to make a change
💡 Why independence — not wealth — is real power
💬 The biggest money mistakes women make (and how to avoid them)
🔥 What it means to truly bet on yourself

If you’ve ever felt stuck, undervalued, or ready for your next chapter, this conversation will remind you: you are your own best investment.

👇 What’s the best money advice you’ve ever received? Drop it in the comments — We want to hear your take.

#aspirewithemmagrede #podcast #podcastinterview #reesewitherspoon #hellosunshine #financialfreedom #financialliteracy #entrepreneur #entrepreneurship #business #businessadvice #sharktank #skims #femaleentrepreneur #womeninbusiness #bookclub #legallyblonde #gonegirl
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SUBSCRIBE
https://www.youtube.com/@EmmaGrede?sub_confirmation=1
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Buy Emma’s Book: START WITH YOURSELF is yours April 2026! Preorder today wherever you buy books or at https://www.emmagrede.com/

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ABOUT ASPIRE WITH EMMA GREDE
Build the life of your dreams and learn from the world’s most successful people.
Emma Grede, one of America’s richest self-made women, wants you to make the most of your life. On ‘Aspire with Emma Grede’, learn through thought-provoking conversations with some of the most successful and smartest minds on the planet, including goop founder Gwyneth Paltrow, investor, philanthropist and former chair of Starbucks, Mellody Hobson, podcast host Jay Shetty, billionaire entrepreneur and Shark Tank star Mark Cuban, and public luminaries like Meghan, Duchess of Sussex, Charlamagne Tha God, Jessica Alba, former First Lady Michelle Obama, and Netflix Co-CEO Ted Sarandos. Each episode will unpack their habits, philosophy, and strategies, covering career advice, well-being, psychology, and, of course, how to win in business. The show offers personal stories, data-driven advice, real-world strategies, and the experience you need to turn your dreams into reality.

LISTEN TO ASPIRE WITH EMMA GREDE
link.pscrb.fm/f0281/Aspire_YT

ABOUT EMMA GREDE
Emma Grede is a founding partner and chief product officer of SKIMS and CEO of Good American. She also made history as the first Black woman to serve as an investor on Shark Tank. Learn more at: https://www.emmagrede.com/

00:00:00 Introduction
00:01:01 What inspired Reese to start Hello Sunshine
00:05:58 Stop “admiring” the problem and start solving it
00:09:02 Building a company with intention
00:12:09 Turning Hello Sunshine from an idea to a success
00:17:37 The importance of knowing what you don’t know
00:21:03 Ad Break
00:26:08 Lessons from selling a billion-dollar company
00:33:32 The most important financial advice for women
00:39:14 Ad Break
00:44:15 How Reese thinks about leadership and power
00:50:48 How Reese’s Book Club is changing authors’ lives
00:54:05 Ad Break
00:58:32 Staying patient for success
01:00:28 Reese’s ambition and her new book
01:04:52 Rapid Fire Questions