Chelsea Handler: Unfiltered, Independent, and Always Evolving

0:00It's late. Your team has a launch to plan while your customer inbox fills up. No worries. In one prompt, Klaviyo builds the whole campaign. The emails, the texts, WhatsApp, all in your voice. Never without your okay. Plus, Klaviyo spots the revenue you're leaving on the table and answers those customer questions so your team can get some rest. Go to klaviyo.com slash best friends. When it comes to AI, there is what we could do and what we should do. What will we decide? I'm Kimberly Nevela, host of the Pondering AI podcast from SAS. Every episode, I sit down with innovators, researchers, and technologists to consider the questions that come after the AI breakthroughs.

0:43Questions that don't have easy answers but need to be asked. If you're curious or concerned about AI, join me as we challenge assumptions and ponder the issues together. Find Pondering AI wherever you get your podcasts.

1:23Indeed.com slash podcast right now and support our show by saying you heard about Indeed on this podcast. Indeed.com slash podcast. Terms and conditions apply. Need to hire? This is a job for Indeed-sponsored jobs. 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 brah 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.

1:59Because it's a totally different skill set. 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.

2:23My 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?

3:05And 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 Sharapova, and this is Pretty Tough.

3:30First 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 said it on Fallon. Yeah. Well, 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.

4:09But 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 me in trouble. Like today? 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, 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.

4:42I 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. 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.

5:16I 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 experience that you actually feel like you're beginning again.

5:58Like, 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, 30s, or even my 40s. In my 40s, I went through 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? What's your purpose? Why are you here? Who are you here for? Are you making people feel good? Are you making them feel bad? 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 into the stuff that you don't want to really talk about when you're younger, I feel renewed and I feel much more optimistic and happy in a way that I haven't felt in my life.

6:47Like 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 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. Right. 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.

7:24And 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 is not a good time to travel with drugs. So I'm just leaving them all over the world. I never thought we'd get to a point where we'd 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.

7:56That's in your DNA. 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. 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 podcasts and I was like, God, she seems so in control. Is there anything that throws you off? Yes, but I think my experience, first of all, I have a very strong constitution.

8:33It 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've practiced. I've practiced since I was a kid. 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. So 10 ,000 hours, 10 ,000 hours of something makes you an expert. I'm an expert in drinking and drug use.

9:18brand always with your okay. Go to klaviyo.com slash best friends. When it comes to AI, there is what we could do and what we should do. What will we decide? I'm Kimberly Nevela, host of the Pondering AI podcast from SAS. Every episode, I sit down with innovators, researchers, and technologists to consider the questions that come after the AI breakthroughs. Questions that don't have easy answers, but need to be asked. If you're curious or concerned about AI, join me as we challenge assumptions and ponder the issues together. Find Pondering AI wherever you get your podcasts. How many third-party vendors does your company use?

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10:27You 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 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 what 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 also don't harp on it. I'm like, oh, okay. But in the moment, you're sensitive to the fact that they've moved on before you want it to move on.

11:12Yeah, yeah. I can read the situation and go, oh, 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 spent a lot of time in Florida. I did not anymore. Yeah, but you did. And I'll never forget that. Okay, that's passed. But now you're spending time in Florida? No, no, no, no, no. I would be in Florida. Oh, you refuse. I'm not big on Florida.

11:44No offense to Floridians. It's not them. It's the government 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 in. Because he's going to move into. 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 when I'm working, like I'm here in New York working for the next couple days, I want to be alone.

12:13I 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 one way to. Well, 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. There. And you have a baby.

12:52So you're. I feel like that's beyond that's that's marriage plus. Yeah. OK, 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 find 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 like she's a sex therapist, a relationship. She's just she's become a therapist.

13:25Yeah, 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, 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.

14:00Although 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. 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. Does he have a name? Cowboy is his name. Okay. 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.

14:30Since when? Just since. Since I've been around the block a couple 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. It's a fair point. 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. The urgency. 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.

15:02Right. 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.

15:39No one shares those stories. Yes. Yeah. Right. I just want to take a second to acknowledge your posture. It's really good. Is it? Yeah. Wow, thank you. So much better than mine. Really? Yeah. Well, you're so tall, you're probably always crouching over, right? Yeah, I don't want to see anyone. See, 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?

16:05Yeah. Do you still consider yourself a comedian, like, first and foremost? And I ask 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 just continues to run through my life. Like 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. Whatever. Athlete slash podcaster.

16:40What would you write? That's a great—I think that every time I'm asked that, and 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. You should be. 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?

17:13To bring joy and laughter and medicine because people need it. 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 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 if 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.

18:01Yeah. Yeah. Like to have that impact. Yeah. 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 it. I guess, you know, for me, I think and 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 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? 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.

18:35It'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 age.

19:26Like 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'm a generous tipper. Thank you. Always. You've 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.

19:59So 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, it's, um, when anyone speaks about you and cause they always like people always see talent and, you know, know famous figures and 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 era very different to how it is now, like with social media.

20:47If 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 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 0253. So please don't get into my account. I've been hacked.

21:19I'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?

21:56It'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 these kinds of videos. These are the reasons, you know, like, let's do. Are you strategic about it? I mean, I have a social media team and I like kind of for you them handle things. I need a little bit of that. Yeah, probably. It's I mean, because I don't want to be. So what you have an actual calendar of 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.

22:25Kids 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 a lot of kids. 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 I do. So you are thoughtful.

22:51So 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. 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. When I say influencer, what do you think of?

23:29I think of just like someone who's selling themselves. In a good way or a 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? A best-selling author or a best-few comedian. But it definitely 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? I think it's the vanilla version of it.