On with Kara Swisher - Pretty Tough with Maria Sharapova: Chelsea Handler

Episode Date: May 25, 2026

Happy Memorial Day from all of us at On with Kara Swisher! Today, we’re bringing you a special episode of "⁠Pretty Tough⁠," a new podcast from the Vox Media Podcast Network hosted by tennis star and entrepreneur Maria Sharapova. Each week, Maria sits down with high-achieving women across industries for candid, wide-ranging conversations about their pursuit of excellence without apology. In this episode, Maria speaks with comedian and best-selling author Chelsea Handler, who's built a career on saying exactly what she thinks, regardless of the consequences. Maria explores what drives Chelsea’s independence across every chapter of her life and how she continues to evolve through therapy, travel, and psychedelics. Pretty Tough is produced in partnership with VOX MEDIA. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Hi, everyone from New York Magazine and the Vox Media Podcast Network. This is on with Kara Swisher, and I'm Karras Swisher. Happy Memorial Day. We're off for the holiday, but we've still got something special for you today. We're bringing you an episode of Tennis Star Maria Sharpova's new podcast, pretty tough. It's another great Vox Media podcast that you should be listening to. In this episode, Maria sits down with one of my favorite people, comedian Chelsea Handler. They talk about how Chelsea has managed to maintain her independence over her decades-long career, what keeps her going now. Maria's interviews are as tough as her backhand, and you all know how fun Chelsea is to talk to, so stick around. You are the only person on your team that knows me, so you should be able to handle the situation, Maria. You have a podcast now, and you need to

start acting like it. I need to be a professional. Yeah, you're a podcast, brough, now. You're a podcast, bro. What's the first step as a podcaster? Well, you have to ask lots of questions, which is, like, annoying, I know, for you. It's really annoying. Because it's a totally different Well, it's annoying interviewing you because you ultimately lead the conversation. Well, but that's going to be a gift for you because it's going to be easier. Is it? Because you're going to be able to ask me a question and then I'm going to be able to expound on it for so long that you don't even have to ask that many questions. Should I just leave then?

Maybe. Okay. This is over. My next guest and I are polar opposites. Comedian Chelsea Handler has built a career on saying exactly what's on her mind, whether it gets her in trouble or not. From stand-up to best-selling books and hit shows, she's never really followed anyone else's rules. She came to watch me play at the Olympics in 2012, and we've been friends ever since. What I've always found so impressive about Chelsea is her independence.

She's created a life completely on her own terms. And she's constantly evolving, whether that's through therapy, travel, or yes, even psychedelics. So I had to ask her, after all the success, what can you? keeps her pushing forward. And does she think I should try a little experimenting once in a while? As always, her answers surprise me. This was a fun one. Because anytime Chelsea's around, I know I'm in for a funny, unfiltered,

an incredibly thoughtful conversation. I'm Maria Sharpova, and this is pretty tough. You're no longer young people. You're just people. And people are either productive or dead weight. It's my first day of work, and I need to make a big impression. Were you just checking me out? No.

It's too bad. I see at least 15 ladies I need to talk to before my beta blocker wears off. My co-workers don't take me seriously. It's not a human. It's just a piece of meat. Someone bring a gurney. Hey y'all, it's Kelly Clarkson with Wayfair. Ever order furniture online and wonder what if?

Like, what if it doesn't hold up? That sofa was four days old. You should have ordered from Wayfair. With Wayfair, there's no what-if. Just style you love and quality you can trust. Visit Wayfair.ca. Fair, every style, every home. First of all, thank you for doing this.

Absolutely. This is like a testament to your loyalty, so I appreciate it. You're welcome. I like to start these segments with a quote, and you've had a lot to say. So it was really challenging. Pulling a quote from you. But the one that I really favored was I have to tell the truth because I'm incapable of anything else. Is that accurate?

Is that a false? You set it on Fallon. Yeah, well, that I wouldn't qualify that as like a quote. You know what I mean? But you said it. Well, I too tell the truth most often. I don't lie a lot. I sometimes lie just to, you know, protect people's feelings.

But as a general rule, especially as a woman, I believe it is very important to be truthful, A, with other women, and B, with everyone else. When was the last time the truth got you in trouble? Oh, all the time. The truth always gets to me in trouble. Like today? I'm constantly running my mouth. I mean, I'm sure I'll say something in this. that will get me into trouble. Or, I mean, at some point today, I have a lot of interviews today.

So at some point, I will say something that will be like in the news, Chelsea Handler said this. Okay. And do you like that? No, no. I don't mean to do that. I just, it's my personality and I've learned to accept it. And the moment you feel it like you're, the truth is going to. Yes. Just be, I just like to be candid. Yeah, I know. I don't like to be guarded. Do you know what I mean? Like, you're more guarded because you've grown up, like having to protect yourself in a way. I've kind of like made a living out of just showing like being myself, rather, you know, like having my personality out there. So I forget sometimes that things are going to be taken out of context or sometimes they're not even taken out of context. I just shouldn't have said it. I shouldn't have been so forthcoming. I mean,

most people struggle with being honest, but you don't because it's just you, that's you. Yeah. It's your personality? Yes, I think so. I think that's what I've learned in the 50 years that I've been with myself. I've learned that that is a big chunk of my personality is to just say what's on my mind. I mean, it's really admirable that you're 50 years old and you are growing and getting better and you're aware of it. Like, what are you still searching for? Well, I mean, you say 50 like it's over. And I would argue that 50, now that I am 50 and I understand life more than I did when I was 30 or 40,

is that you get so much more wisdom and you get so much more experienced that you actually feel like you're beginning again. Like when I turned 50, I was like, oh, this is a reset. Like, I have my shit together now. I'm recalibrating. In a way that I didn't have my shit together in my 20s, or even my 40s.

And my 40s, I went through like a real rough patch in my 40s. And I think it's probably called a midlife crisis because that's what happens. When you turn that age, you start to really think about what are you contributing? Like, what's your purpose? Why are you here?

Who are you here? or four, are you making, like, people feel good? Are you making them feel bad? Like, what do you want to do with your life? So now that I'm 50 and I kind of went through all the ugly therapy part of really getting, like, into the stuff that you don't want to really talk about when you're younger, I feel like renewed and I feel very more, I feel much more optimistic and happy in a way that I haven't felt in my life. Like, I feel calm rather than crazy. Hmm. That worries me. So I feel like you have a lot to look forward to, and all women and men, but I'm a woman, so I'll speak to that, have a lot more to look forward to.

Like, I always looked at 50, like, oh, I'll be dead by 50. It's like, well, no, no. Because of how much you drink? Well, partly, but also because of all the other shenanigans I get up to, you know. How often are you microdosing and psychedelicing? I had a microdose. I just came from Aspen. I was there for three days. I had a little LSD while I was there. That was the last time. And then I gave, I had about 10 little pieces of paper hits that I brought with me. And then I gave those to my friend when I left and said, would you like the rest of these?

Because they lived in Aspen and I felt like probably now it's not a good time to travel with drugs. So I'm just leaving them all over the world. I never thought we get to a point where we be talking about traveling with drugs. Yes. But here we are. That's why you invited me on this podcast. I mean, knowing what you know about me, do you suggest I try psychedelics? I don't think that you are a drug person.

I don't think that. What makes you think that? Well, you're Russian, so you like alcohol. That's just in your genes. Yeah, I do. I like a drink. So that's enough for you. I don't think you're very like, I don't want to say controlling.

No, controlling. Yeah, controlling. Yeah. No, I feel it. When I'm not in control. You don't like it. No. Right.

I don't mind being out of control because I'm always a little, even as high as you can get me, I still know what's happening. I mean, I have a question in my notes because I was listening to a few of your podcast, and I was like, God, she seems so in control. What, like, is there anything that throws you off? Yes, but I think my experience, effort so I have a very strong constitution. It takes me a lot of drinks to even like catch a buzz or to get drunk. Like, I don't get drunk a lot. I mean, you practiced.

I've practiced since I was like, Malcolm Gladwell is like really proud of you. If you put in 28,000 hours or whatever it is. I thought, yeah. 28,000 hours? I thought it was just 10,000 steps. Well, that's per day. You're getting those two things confused. I am.

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Hi, I'm Maria Sharpova, host of the Pretty Tough podcast. Each episode, I sit down with high-achieving women to discuss the pursuit of excellence without apology. This week on the show, comedian and best-selling author Chelsea Handler gives her tips on independence and aging gracefully. I would argue that 50, now that I am 50 and I understand life more than I did when I was 30 or 40 is that you get so much more wisdom and you get so much more experience that you actually feel like you're beginning again. Check out pretty tough new episodes on Wednesdays. You can watch it on YouTube or listen in your favorite podcast app. You generally seem in control of everything, like the situation, a conversation, when you're on stage, when you're writing a book. Is there anything that throws you

off balance? I guess when I feel maybe shunned or invisible. that does throw me off balance. I think if someone, like, knows me and doesn't, isn't interested in talking to me, that, like, if I'm at a party and I'm like, oh, hey, and they're like not interested, I'm like, oh, you know, like, I get it. So you care. Yeah, yeah, yeah, I care. Like, that throws me off where I'm like, oh, but then I don't, I also don't harp on it.

I'm like, oh. But in the moment, you're sensitive to the fact that they've moved on before you want it to move on. Yeah, yeah. I can read the situation and go, oh, who's. that person doesn't like me. In your last book, you dive into the value of spending a lot of time alone. Are you still spending time alone or now that you have like a hot new boyfriend that's... Yeah, he's taking up a lot of my time.

Okay. Is that good or bad? It's good, but he lives in Florida, which I know you love. You spend a lot of time in Florida. I did not anymore. Yeah, but you did. And I'll never forget that. But now you're spending time in Florida? No, no, no, no.

I'm a bid to Florida. Oh, do you refuse? I'm not big on Florida. No offense to Floridians. not them. It's the government, a situation. Yeah, yeah, okay. Political situation. But he's okay. He lives in Florida, and hopefully he will not be living there for that much longer. Because that's not a place that I'm interested.

No, no, no. I will never live with a man. Not full time. Okay. No, I'm not interested in that. Even if you're deeply in love? Yeah, if we're deeply in love, you know, like I like long distance and I like space. So what I'm working, like I'm here in New York working for the next couple days, I want to be alone. I don't want somebody, you know, a plus one around. Yeah, I mean, you're very independent. Yeah. Yeah. So aside from making your own money, what are the ways that other women can be more independent?

Maybe not to your extreme? No, no, right. I'm not a, yes, I understand that. I think that, A, one way to, well, A, yeah, you should be trying to make your own money, definitely. But also, I think women's outlook towards men has shifted in, like, the last 10, years, at least from what I can tell, where there are many women that, like, are thinking about not being married. You're not married. No. And you have a baby. I feel like that's beyond, that's marriage plus. Yeah. Okay. Great. Exactly. So there's a lot of women that are thinking like

what you're thinking. And also marriage seems a lot, like a bit antiquated. And I agree with that. I feel like there's not really a reason to get married anymore, really. You know what I mean? It's just for a big fat party. Yeah. And that's like, I feel like, I feel like, I feel like, I I find the need or the – I deal with this a lot of my podcast where people call in for advice, right? Oh, no, I listened to it. I was like she's a sex therapist, a relationship. Yeah. She's just – she's become a therapist. Yeah, basically. Yeah. Yeah, I took all the things that I learned and gleaned from therapy and then just wanted to spit them right back out.

It's really entertaining. I know. Thank you. I like it. It seems like you're enjoying. It gets deep. It gets quite serious. Yeah. Sometimes. I didn't intend for that to happen. So I'm like – But, you know, if somebody really needs help, I want to help them. But I think my advice to women would be like to not be so desperate to find your quote unquote one or the one. I think that's a load of garbage that we've all been fed. And this is coming from someone who's very interested in the relationship that I'm in right now,

although I don't look at it attached to the outcome of the relationship. Like he's here today. He could be gone next week. Does he have kids? No. And I won't be having kids with anyone. Right. So if he does want kids, he's going to have to do that with his next girlfriend.

You've made that very clear for a long time. I mean, if he's any questions about that, he can just refer to my Instagram. Yeah, or one of your books. Does he have a name? Cowboy is his name. Okay, huh? That's all you're going to give me? Yeah, I mean, I'll tell you, but he doesn't need his name out there.

I'd like to maintain some sort of privacy for him. Since one? Just since, since I've been around the block a couple times and realize how I can just destroy people's lives, you know, by dating them, that all of a sudden they're out there. It's a fair point. In the public eye. It's not really fair. No. I just, that would be my big advice.

It's to stop thinking about like that your... But I think the urgency of meeting a man comes from wanting to have children. Sometimes, but sometimes it's just about like finding the one and not necessarily even taking into account what comes after that. You know what I mean? It's like people want to be in love so badly. Right. And I think that that's... They want the idea of being in love.

Yeah. And we've been sold this pile of goods that tells you like your value as a woman comes from being married. being a wife, being a mother, all of those things. So I would implore women to really just think about what it is you want individually and then go from there instead of thinking that that's what you're supposed to do because society tells you you're supposed to do it. You can have a full life. I mean, obviously, my life is specific and unique,

but you could have a very full life if you decide not to have a child without all that stuff and being a single woman. No one shares those stories. Yes, right. I just, I want to take a second to acknowledge your posture. It's really good. Is it? Yeah.

Wow, thank you. It's a much better than mine. Really? Yeah. Well, you're so tall. You're probably always marching over, right? Yeah, I don't want to see anyone. I have to, because my boobies are so big that I have to make sure that I'm not.

That they stick out. Yeah, that they stick out. So people know that I'm coming. But now that you have a man, you don't need to do that anymore. Thank you. Or you need to do it more. I don't know. Yeah.

Let's, can we talk about your career? Yeah. Do you still consider yourself a comedian, like, first and foremost? And I asked that as like from a point of view of like an identity is when I used to like being an athlete was a huge part of my identity and it only had a certain limit. But the qualities like the things that I learned in my experience through being an athlete is just continues to run through my life. Like even when I even when I fill out forms and they say what's your occupation, even though I don't know what the hell my occupation is at the moment, I still write athlete. But now it's podcaster. Well, whatever.

Athlete slash podcaster. What would you write? That's a great. I think that every time I'm asked that, and I just settled, I've settled on comedian because it's like, when am I going to write author? You know, like, I have thought about that, but I don't identify. Yeah, I guess I strongly identify with the term comedian. And you're proud of it?

Yeah. Yeah, I'm proud of it. I mean, I think of myself as more, like, I feel like a public figure. Do you know what I mean? Like, but that's how I feel. Like, I feel like it's not one thing or another. I just feel like I'm out there. What do you feel is your responsibility as a comedian?

To bring joy and laughter in medicine. More so now than ever. Yeah. I want people to be happy and to remember like kindness, the kindness of strangers to double down on like joyfulness and laughter. Like laughter is really so important and healing. And being able to be like a perpetrator of that, to be able to get on stage and make people forget about how crazy the world is for an hour.

makes me feel very purposeful. Yeah, and I think maybe a few years back, it was like purely entertainment, but now there's like a deeper... Yeah. When we get a chance to go and enjoy someone's performance and feel like it impacts our view or like when I was competing

and someone's had a really crab day and they watch me have a really crab day on the court, but I figure it out and I win. Yeah, yeah, yeah, yeah. Like, to have that impact, I feel like it's not just a moment. Like, it's a feeling. It is.

It's a feeling and it's like, you find, I guess, you know, for me, I think over the course of our lives, our purpose changes quite often. I mean, we're talking about it right now with you, right? Like, your purpose changes. Like, you're living, I think for our youth a lot, we're living for ourselves. Like, what can I do? What do I want? What can I get? What am I, you know, what are? And then I think as you kind of get older, you're like, what am I giving out? What am I? It's not just take, take, take. It's like, okay, let me share. It's hard to acknowledge that in your 20s, 30s. I think that develops over time.

Because you're trying to identify who you are. So then you find your identity and then you like burrow into that, right? And you want to feed it. And you want to be as successful as possible. Right. And then something happens. And then you get successful and you're like, well, what is it? Yeah, what is this?

And then you're like, is this enough? Is this good enough? Is this enough of a contribution? And then you kind of recognize the selfishness in which you've led your life. or for me anyway, that's how I felt. Like, oh, I'm pretty selfish. You know, like, what I just need another big house or, like, what do I need more money? Like, what, you know, and so that, then you start to kind of self-examine. What's your relationship to money? Like, how do you? I like it. Yeah. I mean, you've always liked it from a young eight. Like, you flew first class since you were.

Yeah. I mean, you earned it. Yeah. I earned my own money and I like to spend my own money and I like to share money. You do. I'm very generous. And I always- You're a generous tipper. Thank you. Always. You're also very generous emotionally. Like I remember, yeah, no, at the time, like, when I was really struggling in my career and I had a tough moment and I had the suspension, you called me every single day. And you checked in on me and you were like, this asshole wrote this bad piece about you. But then there was like 10 others that were really positive. So I think today we're doing okay to have someone check in. So you're, you give. That's nice. No, it's true. It's when anyone speaks about you. And because they always, like, people always see talent and, you know, famous figures in a very, in a light that they want to, like, they have an idea. And that's what they associate with that idea. And I'm sure when I say, oh, I'm interviewing Chelsea Handler, like something comes up, right? And whether it's positive or negative, like, they already have an opinion, whether it's about me, whether it's about you. But the first thing I say is how generous. you are. Oh, that's so nice. Thank you. No, it's true. You've come up in a very different media or very different to how it is now, like with social media. If you were building, if you were starting to build your career today, how would you do it differently? Oh my God, I wouldn't even know where

the fuck to begin. I wouldn't know how to do any of this because I've lived through like, and I mean, you two, even though you're younger than me, like we've lived, I've lived, I got my first phone. Like, The internet came out when I was like 19 years old. So I have my original email address. Like, I have an AOL account still. What was your password? 0253. Mine was love and peace.

Well, mine still is O253. So please don't get into my account. I've been hacked. I've lived through the technology age. Now we're dealing with AI. Yes. Like, I don't even know. It's too much of a whirlwind.

I guess I would just start recording videos of myself. You know, it's probably not dissimilar. In your underwear and bra. Yeah. And start telling jokes or telling funny stories in the way in which I am known for. now and I would just be outspoken and probably just do what everybody else was doing. I don't know that I would have some great, grand idea, or I might just be so overwhelmed by it that I wouldn't even try. Do you feel like you constantly have to feed this algorithm, like just constantly

providing content? It's pretty natural for me to provide content. So I don't feel like desperate in a sense. I just feel like, oh, that's easy. Let me make it. I like, I like, I like these kinds of videos. These are the reason, you know, like, let's do. Are you strategic about it? I mean, I have a social media team, and I like kind of let them handle things. I need a little bit of that. Yeah, probably.

I mean, because I don't want to be. So what, you have an actual calendar, like, when you're going to post something? They do. I mean, I don't have a calendar. But, I mean, but, like, you know, I'll be like, oh, I do this thing. Kids are not that great on my social media. So I'll film, like, five of those. And then they'll put them out, you know, over the course of six months.

What do you mean kids are not that great on your social? I do like a video, like a PSA, like, hey, you could be like, you could have a life like me, too. You could be a parent like me. I get up and I smoke a joint and I get to have a cocktail at noon and then I get to take a Xanax at three. Kids, they're not that great. You know, like, silliness like that. Okay. So I have like things like that that that I do.

So you are thoughtful. So my point is like, I don't think 20 years ago you're really like curating a calendar and acknowledging who this content is for. No. Whereas now we know. Yeah, but I also have a lot of help. Like I'm not trying, you know what I mean? I don't want to make it sound like I'm coming up with these. Well, I think most people do.

Yeah. I mean, most people have like a social media person or a strategist or whatever just to keep you, you know, relevant. And as pathetic as that, you know, can sound. I mean, just when I said it, I was like, oh. But that's true. That's what it is. It's true. What do you, when I say influencer, what do you think of?

Like what? I think of just like someone who's selling themselves. in a good way or bad way? I mean, it has a negative connotation, but it's the light, like, it's the reality of where we live, or the world we live in, I should say. I mean, I would be considered an influencer if I weren't a celebrity by now.

You know what I mean? Right, a bestselling author or... Or right, I would probably do that. But it definitely doesn't, it doesn't have a positive connotation. Like the word creator. Creator doesn't have, to me, as negative as a connotation.

as influencer does. I guess creator is like the new influencer, right? Is that the new like it's the vanilla version of it? I think creator sounds a little bit more profesh. So when you're like thinking of grand deals or investments where you have to, you know, you have these like lists of deliverables and you have to act like an influencer, are you up for that? Yeah. As long as they pay you well. Whatever I do, I have a good attitude about it. If I don't have a good attitude about it, then I don't do it. Like if I can't get behind it and be like, okay, I'm going to do this. I'm only going to say something, say yes to something that A, I really like or B, that I'm going to have a fun doing. So if it's just like for money and a paycheck, I usually don't do stuff like that.

You know, I don't. Like for a lot of money, you wouldn't? Well, it depends. It depends. It depends. Yeah. I'm not really like, you know. But it has to make sense.

It does have to make sense. I definitely have done things that don't make a lot of sense. Like what? And I've regretted them. I mean, I've done things. things for big paychecks. Yeah. Can I name them?

Like a brand or a private event? What? Any of the above. Like, for instance, like, as a comedian, you get asked to do a lot of corporate events, right? And they pay you a lot of money. Casinos pay you a lot of money. More money than you make at a theater. So you can say yes to those things and get a nice fat paycheck.

Or you could be like, that's miserable and I don't like the vibe there. Like, for me, a lot of casinos don't have the right vibe. Like, I perform at the Cosmo. in Vegas. You're at the casino all the time. Why does that not make sense? It seems like such a natural connection. I have a residency at the Cosmo in Vegas.

That makes sense. That's something my friends can come to. Well, you can do that and then you can go like get a half million dollar check. Yeah. Well, I make, you know, I like that. But like going to a casino in the middle of Minnesota where, you know, it's not the greatest environment and it's not fun for me or it's not going to be, you know, like an elevated situation, no, I don't want to do that. And I don't want to have to do that.

You've said in your book that you're not a big planner, right? That you don't approach your career looking like five years ahead. But like how do you, when you think of your career? I mean, there must be a strategy. Is there? No. No. I don't plan for things. It's basically... How do you plan for your next book? How do you plan for your next show? I... How does that start? It's just, it's just, I get a hair in my ass. and then I'm like, okay, I got something. Like, I have, like, I believe very strongly that there is, like, a time to harvest. And, like, there's a time to plant and then there's a time to harvest.

And sometimes you're just planting and or sometimes you're just waiting in the middle. You're not doing anything. You're just, like, if I can't force myself to come up with material if I'm not inspired. Usually it's sparked by me going on some crazy trip and I come back. Or being in a relationship and breaking up. Yeah. Right. That's inspiring.

Or not? Or not? And you want to write about it. But it could be inspiring to other people. Like that's what I mean to circle back to like, you know, one of my books was like, it was off the back of me breaking up with Joe Coy. And I was like, I was supposed to write a book about falling in love. And then we broke up. And I was like, I had this book deal. And I'm like, all right, forget it.

I'm not writing a book about, you know. Wait, so they paid you for this book deal. And then you started writing and then you broke up. Mm-hmm. And then I said, okay, here. We're pivoting. I said, I'll give you the money. back. Like I can't, I'm not writing a book about being in love. We just broke up. And they said,

why don't you write a book about breaking up? I said, I'm not writing a book about breaking up. That's not inspiring. So then I said, give me six months and let me see if I have something in me. And so I took six months and I thought, do I have something? And I started writing things. And then it turned into my last book, which had a couple of chapters about my relationship with Joe Koi, or the breakup, I should say. But it wasn't about a breakup. It was about how to pick yourself up after a breakup. And the book was about much more than that. So I think I always just, I can't do something fraudulently. Like, I have to feel it, and I have the luxury of being able to do that in my life where I don't have to take money.

So I know not everybody has that luxury. So I recognize that every single fucking day of my life, believe me. You're also a workaholic. You don't stop. I do work a lot, yes. You work a lot. I tour. So right now I'm here for three days, and then I have, like, three shows.

Then I go home, and then I work for five days. You know, like I have lots of shit going on. You're in it. So I like that. I don't know that I, I mean, I like my lifestyle and I like to afford a certain lifestyle. So there's definitely that element, you know, but I'm not for. Is it a pressure of maintaining that lifestyle? I mean, I definitely have grown accustomed to my lifestyle.

And I would like to keep things rolling. So you're keeping it up. Yeah. So I'm keeping it up, but I don't dislike working. I like working. Yeah. So I don't think, you know, so it's definitely, there's going to be a time where I get and be like, okay, how much do I want to continue working this hard? Yeah, you work hard.

Yeah, thank you. You write a lot. What is it like when you have a book deal and you know there's something that needs to be delivered? What is your process like? My stand-up and my writing, it's like they kind of go together and overlap a lot. So like if I'm telling a story on stage and it's really funny, and that's usually like the funniest parts of the story because it's stand-up. But if I really want to like get into that story and write about it in a book, I have to get into the details and set the scene and talk about all the characters. that are part of that story. And that is like a nice little avenue of exploration for me.

Like as a creative person, I like to do that because then you're like a sign, you have characters and it's like, oh, my brother and sister were there and let me give them lines. And then like, what did they say and who else was there? Like, for example, there was a story in my last book about going to the bush compound, Kenny Bunkport in Maine. We were renting a house there for a month. And I, and I'm friends with the Bush sisters. And they were like, oh, had heard I was in the area. and so they invited us over to Pickleball, play Pickleball. I know that's going to be your favorite things. That should have been your first time.

Well, I was not interested in going. Just on the record, I was not interested in going to Kenny Bunkport. I did not want to be seen with George W. Bush. I don't even want to meet George W. Bush. They guarantee, I said to them, sissies, I will, everyone at my house wanted to go over there. I had about 10 people, brothers, sisters, friends that were staying with me. They were like, do not take this opportunity away from us because of your political bullshit. And I'm like, listen, I, my back was out.

I was not in the mood. I hate pickleball. I had no reason to go over there. But yet, I did it for the group, right? So we get there. And I, Barbara Bush promised me. She said, Sissy, I said, I do not want to meet your father because I do not want to disrespect your father. And I don't know that I can trust my personality in this moment. I have outbursts. And she promised me that I would not meet her father. And within five minutes of landing at their house and pickleball game starting, guess whose father I met? Hers, George W. Bush. Did you control yourself? I did. I had lots of edibles that day because I knew I was going somewhere where I did not agree with them. And I did not want to do that. I didn't want to behave badly in someone else's house. That's terrible. You know what I mean?

So I had a lot of drugs. My brother said to take two edibles. My sister said take three. So I took three. That subdues my personality. And I was able to go over. What was the question again? Oh, oh, this is, I remember.

We're talking about writing. So, like, that story. is full of ridiculousness. Like my brother came over. My brother didn't even recognize him at first. So he was like, oh, my God, is that the president? We're like, yeah, you idiot. How do you not know who one of the presidents was, is?

And there were a lot of funny things about that story. Sophie was with us, our mutual friend. She was with us at that. So do you go home that evening and just start writing? No, it just marinerates in my brain, and we start telling the story. And then I start repeating the story. and then I start realizing how funny it is, and people are laughing at this part and that part.

And then I emphasize things, and I exaggerate little things here and there for the purpose of storytelling. And then I'm like, all right, I'm going to put this in my stand-up. So you're testing the material before you put it in writing? Yeah, I tested it. And then by virtue of that, thank you.

By virtue of doing that, then that usually leads to me putting it in my book. Or vice versa. Like, I'll put it in my book and be like, okay, this will be funny for stand-up, but I have to make it truncated and make it much shorter. So, but most of my books, like, I mean, you know, are inspired by things that have actually happened, you know, the stories are true.

They're not made up. You know, some of them are embellished or put together, like, as one story, even though they were two separate stories. Well, some of them should be embellished. Is there, is there something that you haven't achieved yet that you'd want to achieve? Well, I'm, I just, we just sold a show to Hulu, where I will be playing a washed-up reality star whose daughter comes back. She is a strange daughter,

and she comes back into her life. This woman does not want to be a mother. There's a lot of similarities between me and this woman. And it's based on the kind of culture of growing up in the time that I did with reality television, like the outset, you know,

the onset of reality television and all these kind of hot messes that come along with reality television. And so I would be acting and starring in the show. I will be acting and starring in the show. So I haven't done that yet. Did you pitch the show yourself? Yeah, I did with the right.

write it? No, a writer named Zoe wrote it. So how does that work? You come together with a writer, you have an idea, she puts it on paper, and then you sell it? Yeah, yeah. We basically kind of like work together for a few months, preparing the pitch, preparing the idea, then you go out to all the networks, the platforms, and you pitch the show, and then whoever buys it, buys it. The best bidder? Yeah. Do you want to pitch a show? Not yet. Okay, well, that seems like it might be next for you. Who knows? Yeah. You're good with investments, though.

I think so. I think so. You're also, no? You've made some bad ones? Yeah, I've made some bad investments. Can I hear of one bad one? Yeah, I invented 200, I invented. I invested $250,000 into nude sticks, the makeup brand, and then they went bankrupt.

How soon after your investment? About seven years. Oh, well, at least it was like a slow burn. Yeah, yeah. So that was misguided. and, you know, I wouldn't have done, I don't know why I did that. That wasn't really thought out. I just thought somebody asked me if I'd invests. And I was like, sure, yeah, no problem. I mean, 250 is quite a big check for something that you're not familiar with. So that's what you learned your lesson. I think so. I think I learned my lesson about that. What's been one of your best investments? I mean, but it is already because I invested in love volleyball, the team. Oh, I'm an investor in this. Oh, yeah, you are. Oh, great. Yeah. Okay. So that's a great investment. Can we go to a game together? Yeah, absolutely. I'm dying to go to a game. Okay. Let's go. Yeah, we'll do that. This week on Networth and Chill, we're joined by Danielle Robay, the journalist Forbes called

The Queen of Questions and the host behind Reese Witherspoon's Book Club podcast and her own show, Question Everything. We're exploring a skill that can transform your career, relationships, and bank account, knowing how to ask the right questions. Danielle breaks down the art of getting real answers in professional settings, from coffee chats to career pivots and shares the money conversations we should all be having but aren't. Get ready for hard-hitting advice on defining success beyond the dollar signs, asking better money questions with partners and friends, and the mindset shifts that separate people who stay stuck from people who keep growing. Listen wherever you get your podcasts or watch on YouTube.com slash your rich BFF.

I only have a few questions left. Actually, these are five pretty tough questions. Oh, okay. Are you going to ask me to spell something because I'm ready? No, I'm not going to ask you. No. What is something you've had to unlearn? to not insert myself into everyone's problems and try to help everybody. Some people don't want help. Right. And you're not Mother Teresa. And I'm not Mother Teresa.

Definitely. So stop it. And let people ask for help if they want it. Accurate. What's a routine that's helped shape your success? Working out every day when I wake up. It's funny. So many women have that same answer.

Because it just makes you feel strong and like gives you a clarity of mind. Like sweating in the morning is the best thing you. can do. And it sounds, you know, kind of like obvious, but it's just a great way to start your day. I like to accomplish anything else. At least you did something for yourself. I like to do that. I love, yeah. I've actually really grown to love working out, which is a sentence I never thought I would say. I know. I see your workouts. You're like. Yeah. Hardcore. Yeah. Yeah. I think you're like stronger than I am. I bet I am. I bet I could beat the shit out of you. You're a better skier. You're better. You're stronger. What's a common misconception about you?

I mean, who know? There are many. You tell me. You tell me. You would know more about misconceptions than I would know about myself. No, but what's one that you've heard? Because you like to, like, you're not afraid of reading other people's opinion about you. Probably that I'm difficult. Like, I'm not difficult.

I'm pretty straightforward. Like, I'm not drama. I don't have any drama. I mean, I do. You know, there's drama in all of our lives, but I'm not. I'm not difficult. I don't, I'm not trying to like play games or be KG, you know. No, you're definitely not. What is your relationship to perfection? I'm not a perfectionist. I'm pretty, like, I'm pretty, I still don't love my relationship

with my body. I still am very judgmental about my body. Even now? Yeah, I love my body. I love what, like, I like the way I look. I'm glad that I put so much effort into it. But I still am very aware of, oh, if I feel like I haven't worked out in a couple days or I feel bloated. Like, I just want that narrative to get out of my mind because I would never want any woman I know to feel that way. So I could get better on that. How are you going to get better? My body image. I don't know.

I just have to keep trying. And one day you get there. Okay. How's your body image? Not as good as it was when I was playing. Really? Yeah. Oh.

Well, because I was like strong. Right. But you don't feel strong? Not as strong as I did. No. Yeah. Not physically. I guess women have all had a kid.

Yeah, right. It's just like your body, no matter what you do, your body is never the same. Oh, yeah. I know you don't know. I don't know. No. No. Okay.

What makes you feel tough? Giving it to men straight, you know. I'd die. Yeah. Letting a man know, like, don't come any closer and don't fuck with me. It makes me feel pretty good. What makes you feel pretty? When I have no makeup on and I'm skiing, you know, then I feel cute.

Natural. Like I feel cute when I'm like not dolled up and stuff. Like when I get dolled up, I start to feel powerful. I put on high heels and I'm like, okay, you have to be in the control seat. You're the driver. Like I really like not being the driver. Like I was saying this to my friend the other day, like I will always lead in a situation that requires a leader, but I'd rather not be the leader. I'd rather somebody more capable.

But if there is no one more capable, then I'm totally. down to do it, but I'd rather not do it. But which happens most of the time. But I'd rather not lead. Because you can't help yourself. I know, I know, but I just feel like it's just more efficient sometimes, you know, to get myself in there and start steering the ship. I just feel like, let's go.

Come on. This is all I have for you. This was, okay, okay, we did all right. I think this was successful. Okay. This was very nice. Goodbye. Bye.

Bye. Thanks for listening to this special episode of Pretty Tough. happy Memorial Day. We'll be back with a new episode of On with Caras Wisher on Thursday.