Five Pretty Tough Questions

Hi everyone from New York Magazine and the Vox Media Podcast Network. This is on with Kara Swisher, and I'm Kara 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 Sharopova's new podcast independence over her decades long carrier and what keeps her going now. Maria's interviews are as tough as her back 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 bruh now. You're a podcast bruh. What's the first step as a podcaster? Uh well you have to ask lots of questions, which is like annoying, I know for you. It's annoying interviewing you because you ultimately lead the conversation. So that's gonna be a gift for you because it's gonna be easy. Is it? Because you're gonna be able to ask me a question and then I'm gonna 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 keeps her pushing forward? And does she think I should try a little experimenting once in a while? As always, her answers surprised me. This was a fun one. Because anytime Chelsea's around, I know I'm in for a funny, unfiltered, and incredibly thoughtful conversation. I'm Maria Sheripova, and this is Pretty Tough . Recommendations can be great. Maybe someone recommended this podcast, and here you are. But home projects are a little different. If the podcast isn't your thing, you might lose a few minutes from your day, but if you hire your cousin's neighbor to mount your TV, you might end up with a lop sided screen and wall damage. I know a guy isn't a good strategy for your home. That's why thumbtack works so well . It matches you with top-rated local pros with photos, reviews, and credenti als all in one convenient place. For your next home project, try thumbtack. Hire the right pro today . You're no longer young people. You're just people. And people are either productive or dead weight. 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 me at. Someone bring a gurney . It's the family and friends event at Shoppers Drug Mart. Get 20% off almost all regular priced merchandise. Two days only. Tuesday, May 26th and Wednesday, May 27th. Open your PC Optimum app to get your coupon . First of all, thank you for doing this. It means we like this is like a testament to your loyalty. So I appreciate it. You're welcome. Yeah. I like to start these segments with a quote. And you've had a lot to say. So it was 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 said it on Fallon. Yeah, I well that I wouldn't qualify that as like a a quote. You know what I mean? But you said it. Well I too tell the truth most of the time. I don't I don't lie a lot. I sometimes lie just to h n you know uh protect people But as a general rule, especially as a woman, I believe it is very important to be truthful w A with other women and B with everyone else. And when when was the last time the truth got you in trouble? Oh, all the time. The truth always gets me in trouble. I'm constantly running my mouth. I mean, I'm sure I'll say something in this interview that will get me into trouble. Or 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 gonna yes. Just be I just like to be candid. Yeah, no. I don't like to be guarded, 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. It's your personality. Yes, I think so. I think that's what I've learned in the fifty years that I've been with myself. I've learned that that might that is a big chunk of my personality is to just say what's on my mind. I mean it's really it's really admirable that you're fifty 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 fifty like it's over. And I would argue that fifty, now that I am fifty and I understand life more than I did when I was thirty 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. 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 twenties, thirties, or even my forties. In my forties, I was I went through like a real rough patch in my forties. 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 what's are you contributing, like what's your purpose, why are you here? Who are you here for? 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 the ugly therapy part of really getting like into the stuff that you don't want to really talk about when you're younger, uh, 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. 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 f to that, have a lot more to look forward to. Like I always looked at fifty like, oh, I'll be dead by fifty. It's like, well, no, no. Because of how much you drink? Well, partly. But also because of all the other shenanig ans I get up to. How how often are you microdosing and psychedelicing? I had a micro dose. I was 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 ten 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's not a good time to travel with drugs. So I'm just leaving them all over the world. I just I never thought we'd get to a point where we'd be talking about traveling with drugs. Yes. Well but here we are. That's why 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. Mm-hmm. I don't think that. What makes you think that? Well, you're Russian, so you like alcohol. That's just in your genes. That's in your DNA. I do. I like a drink. So that's enough for you. I don't think you're very like um I don't want to say control no controlling. Yeah, controlling. Yeah. I feel it. When I'm out of control I'm not in control . No. Right. I don't mind being out of control because I'm always a little even as as 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 podcasts 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 at first of all I have a very strong constitution. It takes me a lot of drinks to ha even like catch a buzz or to get drunk. Like I don't get drunk a lot. I mean you practiced. I I've I've practiced since I'm Malcolm Gladwell is like really proud of that. Yeah. Twenty eight thousand hours, ten thousand hours. Well that's per day. You're getting those two things confused. I am. So 10,000 hours, 10,000 hours of something makes you an expert. I'm an expert in drinking and drug use . Support for this show comes from Quince. The changing of the seasons also comes with a changing of your wardrobe. 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So why make it harder with a dozen different apps that don't talk to each other? Introducing Odoo. It's the only business software you'll ever need. It's an all-in-one fully integrated platform that makes your work easier. CRM, accounting, inventory, e-commerce, and more. And the best part, Odoo replaces multiple expensive platforms for a fraction of the cost. That's why over thousands of businesses have made the switch. So why not you? Try Odoo for free at Odoo.com. That's ODO .com. 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'm uh when I feel uh 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, Who oh. You know, like I get it. So you care. I yeah, yeah, yeah. I care. Like that throws me off where I'm like, oh. But then I don't I I also don't harp on it. I'm like, oh But in the moment you're sensitive to the I go I read that they've moved on before you wanted to move on. Yeah, yeah. I can read the situation and go, oh, that person doesn't like me. It 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 live. Uh you spent 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, no. I have a big one. Do you refuse? I'm not big on Florida. No offense to Floridians, it's not them, it's the government a situation. 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 to be able to do 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? Um maybe not to your extreme. No, no, right. I'm not a yes, I understand that. I think that A one 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. So I feel like that's beyond that's 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? Like it's just for a big fat party. Yeah. And that's like I I f findind the need or the d I deal with this a lot on my podcast where people call in for advice, right? Oh no, I listened to her. I was like, she's like she's a sex therapist, a relationship 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 gonna have to do that with his next kid. I mean 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. But uh Does he have a name? Cowboy is his name. Okay. That's all you're gonna 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 when? Just since since I've been around the block a couple of times and realized how I can just destroy people's lives, you know, by dating them that all of a sudden they're out there and in the public eye. It's not really fair. No. I just that would be my big advice is to stop thinking about like that 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 it to account the what comes after that. You know what I mean? It's like people want to be s 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 can have a very full life if you decide not to have a child without you know without all that stuff and being a single woman. Like no one shares those stories. Yes. Yeah. Right. I just I want to take a second to acknowledge your posture. It's really good. Is it? Yeah. Wow, thank you so much. So much better than mine. Really? Yeah. Well you're so tall, you're probably always over. 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 ident ity 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 and 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 what the hell my occupation is at the moment, I still write athlete. But now it's podcaster. Well whatever. Athlete slash pod caster. What would you write? That's a great I I think that every time I'm asked that and I just settle I've settled on comedian because it's like, what am I gonna write? Author, you know, like I I have thought about that, but I don't identify, yeah, I guess I str my 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 I 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 because people 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 for 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 I think maybe a few years back it was like purely entertainment, but now there's like a deeper when we get a chance to go and enjoy someone's performance and feel like it impacts our view, or like if when I was competing and someone's had a really crowd day and they watch me have a really crabb day on the court but I figure it out and I win. 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 in our I think over the course of our lives, our purpose changes quite often. I mean, you're we're talking about it right now with you, right? Like your purpose changes. Like you're living I think for for our the our youth a lot, we're living for ourselves like what can I do what do I want what can I get what 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 o,kay, let me share. It's hard to acknowledge that in your twenties, thirties. 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 some and then you're like, is this enough? Is this good enough? Is this enough of a cont ribution? And then you kind of re recognize the selfishness in which you've led your life, or for me anyway, that's how I felt. Like, oh, I'm 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 age. Like you flew first class Yeah. I mean you earned it. Yeah. I earn 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 You're a generous tipper. Thank you. Always. You've always you're also very generous. emotionally Like I remember Yeah, no. I 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 ten others that were really positive. So I think today we're doing okay. So have someone check in. So you're uh you give.. That's nice No, it's true. It's it's um when anyone speaks about you. And 'cause they always like people always see talent and, you know, famous figures in the own in in a very in a light that they want to pers 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 Hanler 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. Um 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 in a very different media era, 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 I mean you two even though you're younger than me like we've lived I 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. was W yourhat password? Um 0253. Uh mine was Love and Peace. Well, I mine still is O two Five Three, 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 just 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 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 have to. Do you feel like you constantly have to feed this algorithm, like just constantly providing content? Um 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 a I like these kinds of videos. These are the reasons you know, like let's do I do And are you strategic about it? Uh I mean I have a social media team and I like kind of like them handle things. I need a little bit of that. Yeah, probably. It's I mean, 'cause I don't wanna be So what you have an actual calendar of like when you're gonna 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 like you don't have to do? I do like a video, like a PSA. Like hey, you could be like you could have a life like that. 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, so they're not that great. You know, like silliness like that. Okay. So I have like things like that that I do but So you are thoughtful. So my point is like I I don't think twenty years ago you 're really like curating no a calendar and acknowledging who this content is for. No. Whereas now we we know. Yeah, but you I also have a lot of help. Like I'm not trying you know what I mean? I don't wanna uh make it sound like I I'm coming up with these I mean most people do. Yeah. I mean most people have like a social media person and or a strategist or whatever just to keep you, you know, relevant and as s as pathetic as that you know, can sound. I mean, just when I said it, I was like, ooh. Uh, but that's true. That's what it is. It's true . What 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? So I get it. But it definitely does 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's like the new influencer, right? Is that the new like I think it's the vanilla version of it. I think creator sounds a little bit more prof . Like so when you're like thinking of brand 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? Um yeah. As long as they pay you well? Whatever I do, I'm 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 gonna do this, I'm only gonna say say something something yes to that A I really like or B that I'm gonna have 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 how much money and it depends what it is. 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 for big paychecks. Yeah. Can I name them? I I mean 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? 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 the case. Well you can do that and then you can go like a little half million dollar check and Yeah. 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 gonna 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 said in your book that you're not a big planner, right? That you don't 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 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 get I get a hair in my ass and then I'm like, okay, I got something. Like I have like I've believed 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. Like how do you try Why not? Well you want to write about it. But it c 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 a like it was off the back of me breaking up with Joe Coy and I was like I was about to I was supposed to write 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 break you know. Wait, so they they 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 I'm pivoting. I said, Well, I'll give you the money back. Like I can't I'm not writing a book about being in love. I 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 it had a couple of chapters about my relationship 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 have 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 I recognize that every single fucking day of my life, believe me. But you're also a workaholic. Like 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 the my lifestyle and I like to afford a certain lifestyle. So there's definitely that element, you know? But I'm not sure. Is it a pressure of maintaining that lifestyle? I mean, I'm definitely have grown accustomed to my lifestyle. Yeah. 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. So I don't think, you know, so it's definitely there's gonna be a time where I get and be like, Okay, how much do I wanna continue working this hard? Yeah, you work hard. Yeah. Thank you. You write a lot. Like what is it like when you 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 I I 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 assigned 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 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 uh 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 those are the same 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 Bunport I did not want to be seen with George W. Bush. I didn'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 with the 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 would 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 the f and I the 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. So 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 two edibles. My sister said take three. So I took three. That subdues my personality. And um I was able to go over what was the question again? How do oh oh oh this is w I 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. Um 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 and just start writing? No. It just marinates 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 gonna put this in my stand-up. So you're testing the material before you put it in writing. Yeah, I test it in. And then by virtue of that, thank you. By virtue of doing that, then that usually leads to me putting it in my book . Like 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 it, 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. 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 be playing a washed up reality star whose daughter comes back. Um, she has 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 outside, you know, the ons et 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 writer. Did you write it? No. So how does that work? You you come together with a writer, you have an idea, she puts it on paper, and then you sell it? Yeah. Yeah. We we basically kind of like work together for a few months preparing the pitch, preparing the idea. Then you go out to all the the networks, the platforms, and you pitch the show, and then whoever bu buysys it it . The best bidder? Yeah. Do you want to pitch a show? Not yet. Oh, 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 one bad one? Uh yeah. I invented two hundred I I invented. I um invested two hundred and fifty thousand dollars into nude sticks, the makeup brand. And then they went bankrupt. How how soon after your investment? Uh 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 invest, and I was like, sure, yeah, no problem. I mean 250 is quite a big check for something that you're not familiar with. You learned your lesson. I think so. I think I learned my lesson about that. What's been one of your best investments? I just inve well, it hasn't been yet. I mean, but it is already because I invested in l uh love volleyball. Oh the team. I'm an investor in Love Volume. Oh yeah, you are. Oh great. Yeah. So that's 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 we'll do that. Hi, I'm Maria Sharapova, 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 . Why is this it's still like burning inside of me that I feel like I am missing something? I prayed so hard for my girl. I prayed like every night, prayed, prayed, prayed. And when I lost my babies, it was so hard. So that when I had them, I thought that was gonna be the thing. Like I am finally getting the thing that I prayed for, and it's going to fulfill me, and this is everything I want and more . And it was, but it was also somet hing missing . I'm Raven Ad sun, and this is Mother hood the Remix from Project Swagger. This series is about defining our own versions of Motherhood. I am bringing in a mama I adore and admire. My friend, fellow Peloton instructor Kirsten Ferguson listen now at Project Swagger Where exactly do US China relations stand the Chinese side came in feeling as if they had figured out how to work both with and against Trump. He was inclined to try to create moments of crisis, and then if they stood up to him. They were almost uniquely capable of making him back down. I'm Priet Barara, and this week Evan Osnos of The New Yorker joined me to discuss the Trump Xi Summit, which he reported on from Beijing. The episode is out now. Search and follow stay tuned with Preet wherever you get your podcasts . I only have a few questions left. Actually, these are five pretty tough questions. Oh, okay. Are you gonna ask me to spell something? Because I'm ready. No, I'm not gonna 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's just makes you feel strong and like the frame of mind 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 that. I like to I like to do that. I love yeah. I've actually really grown to love working out, which is a s 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 You're a better skier. You're you're a better, you're stronger. Shit. Um what's a common misconception about you? I mean who knows. You tell me. You tell me. I would 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 you're not afraid of reading other people's just that opinion about it? Probably that I'm difficult. Like I'm I'm not difficult. I'm pretty straightforward. Like I'm not dra ma. I don't have any drama. I mean I do, you know, there's drama in all of our lives, but I'm not uh I'm not difficult. I don't I'm not trying to like play games or be cagey, you know? No, you're definitely not. Um, what is your relationship to perfection? Um I'm not a perfectionist. I'm pretty like I'm pretty I I I still don't love the my relationship with my body. I still am very judgmental about my body.