Chelsea Handler on Men, Trump & Money (+ Excellent Parenting Advice)

Speaker 2 Hi, everyone, from New York Magazine and the Vox Media Podcast Network. This is on with Kara Swisher, and I'm Kara Swisher.

Speaker 2 My guest today is the comedian and seven-time best-selling author Chelsea Handler. She has a new Netflix special titled The Feeling that comes out March 25th.

Speaker 2 And she recently released a new book called I'll Have What She's Having.

Speaker 2 It was published on her 50th birthday, and fittingly, it's a collection of essays that chronicle her journey to becoming the woman she always wanted to be, or as she puts it, a beautiful hurricane.

Speaker 2 I found the book very funny and full of really interesting lessons.

Speaker 2 I love talking to Chelsea, not just because she's hilarious, but she's also politically engaged and a savvy entrepreneur who's been very successful in streaming, podcasting, publishing, and touring.

Speaker 2 I spoke to her last Sunday on the Box Media Podcast stage at South by Southwest, and we got into all of it: her new book, Politics, and the Business of Being Chelsea Handler.

Speaker 2 I also told her she needs to date Elon Musk in order to save us from this nightmare. She declined.
Unsurprisingly, it was a great conversation, so stick around.

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Speaker 5 Yay! Yay!

Speaker 3 We're here. Finally, the only person I really know.
I had a great time with Elizabeth Warren yesterday, but I'm super excited.

Speaker 8 I'm jealous that I wasn't here for that.

Speaker 3 Yeah, she was great. She was great.

Speaker 8 Love Elizabeth Warren.

Speaker 3 Yeah, she's fantastic. So, Chelsea, thanks for joining me in this conversation of Vox Media Podcast Stage at South by Southwest, presented by Smartsheet.

Speaker 3 Let's start with your book, which is number one on the New York Times bestseller list.

Speaker 1 Debut. Wow.

Speaker 3 Why do you think that is?

Speaker 8 Why do you, you know, there's a lot of right-wing books up there.

Speaker 3 There's a lot of stuff like that. Why, I know, but why do you think you got to number one?

Speaker 8 I don't know why I got to number one. I have a pretty good track record of getting to number one.
Yeah. So this is my sixth number one New York Times bestseller.

Speaker 8 And thank you so much. I'm very, every time I was just telling Kara backstage, it just never gets old to get that phone call that you're number one on the New York Times list.

Speaker 8 And I'm from a family of six children. I'm the only one who didn't go to college.
So I love calling my brothers and sisters and congratulating them on their wasted efforts.

Speaker 8 in college and that I was right all along. I was the youngest of six and I would tell them, you guys stick with me.
I will show you the way.

Speaker 8 I will take this family to the next level. And now they know that I was fucking right.

Speaker 3 That's right. That's right.

Speaker 8 Which you write about a lot in this book.

Speaker 3 But you started the book with a quote, to have and not to give is worse than to steal. Why is that the quote?

Speaker 8 Because I really appreciate generosity, my own generosity, the generosity that my mother instilled in me. And I think the world obviously could use a lot more of it now.

Speaker 8 And it's very important to share everything you have, including your stage, your time, whatever you have to give, give it.

Speaker 8 And give it, you know, and are you, and when you're done giving, are you sure that's all you have to give? Because I could bet you you can find more to give. And

Speaker 8 it's the world that we're living in.

Speaker 8 We need more of that. And I want generosity of spirit.
I want to demonstrate it. I want to display it.
And I want to spread it.

Speaker 3 Yeah. Excellent.
So you also dedicated the book to stewardesses. And there's a great scene in the book.

Speaker 8 That's a very antiquated term, Kara.

Speaker 1 They're called flight attendants, okay?

Speaker 8 Please get with the program. I know you're flying around privately, but

Speaker 8 try and remember us small people, please.

Speaker 3 Flight attendants.

Speaker 1 Flight attends. Mostly women, though.

Speaker 3 You did say.

Speaker 8 They're mostly women. And then the men that are flight attendants are also our sisters.
Okay, all right.

Speaker 1 So why did you dedicate it to them?

Speaker 8 I spend a lot of my time on flights. I'm sure many of us in this room do.

Speaker 3 But you just say you wanted to from the early time. You walked through first class and said, these are my first flights.

Speaker 8 Yeah, well, I wanted to spend my time in first class from a very young, early age.

Speaker 8 When I was on my first flight, I walked past the first class section i was like i sniffed around i was like this seems like my group and my mom was like this is not our group you will never be able to fly first class we can't afford that and i was like uh speak for yourself right so um anyway i do fly a lot and for work for whatever i spend a lot of my time on planes i wrote half this book on planes and flight attendants have been through hell people treat them terribly and they need our respect and they need our patience.

Speaker 8 They are stuck with us in the sky and we need to be nicer to them.

Speaker 8 And yeah, after COVID and all of those.

Speaker 3 A white lotus in the sky.

Speaker 8 I mean, yeah, white lotus in the sky, right? You're stuck in a tube of disgusting air. Let's be sweet and generous and gracious to them, please.

Speaker 3 And you offered to beat people up.

Speaker 8 I will always be on a plane and act as a flight attendant. Yes.

Speaker 1 Yes, yeah.

Speaker 8 If there is a problem or a nuisance or someone needs to be removed, I'm your girl.

Speaker 3 Yeah. One of the reviews was a pleasingly unformulaic book of hard-won advice that never rings false.

Speaker 1 Do you like that review?

Speaker 8 Oh, I never heard it.

Speaker 1 Yeah, sure.

Speaker 1 Yeah.

Speaker 3 I love it. Are you pleasingly unformulaic?

Speaker 8 I'm unformulaic, yeah. And if it's pleasing to you, that's your opinion.
Yeah, I'm glad to be pleasing somebody. I just need to please a few people, not everybody.
Who do you have to please?

Speaker 8 Just enough people to give me my career, you know, the fans. I want to please my fans, the people who've provided me with this life, but I'm not looking to please people.
I'm not a people pleaser.

Speaker 8 Yeah. I want people, I want to spread joy and sunshine, but I'm not trying to please you.

Speaker 3 Right. I can see that.

Speaker 3 So

Speaker 3 explain how your father changed you. You've built a very deep and caring relationship with three girls whose dad you used to date.
We just talked about it backstage.

Speaker 3 They called you father, and you write that one of the girls said to you, father is always with us, even when she's not.

Speaker 3 And you thought to yourself, this is the single best sentence I ever heard in my life. Yeah.
Explain this story. I found it,

Speaker 3 I have a lot of kids, as you know.

Speaker 8 A lot of kids.

Speaker 3 And I was very upset upset by the story of you moving in there. Not that you did, I felt good that you did, but these kids had been kind of left alone by their parents in a way.

Speaker 8 Yeah, their parents just kind of had kids and they were career people and they thought, well, these kids will be of the world.

Speaker 8 You know, not like they, they were kind of two people with huge careers that also had children, not people who had children who also had huge careers. Do you know what I mean? Yeah, I know.

Speaker 8 So the kids were kind of left by the wayside. And my ex-boyfriend and his relationship with his girls just hurt me.
Like it hurt my heart. And I'm from a family of three girls, three boys.

Speaker 8 And when I saw these girls, I recognized in them so many things I felt in my adolescent angst and my, like, you know, the neglect and the needing to be seen and the feeling of being ignored and how that, like, I related to that feeling so much that I just wrapped these girls up and became for them whatever I could be, which was like an interim parent.

Speaker 8 And they call me dad. Well, they call me father because they have a dad.
So they call I'm father and he's dad. He's very confused all the time.

Speaker 8 I was also very confused, but they are huge loves in my life. They still are.
And I shared that in the book because people think that I don't have children, so I hate children.

Speaker 3 But you do have comedy about hating children.

Speaker 8 Yeah, I mean, I want to be child-free. I'm very excited that I've remained that way and that I've remained single for as long as I have.
Like, I feel like now I'm free.

Speaker 8 I got out of that tunnel where those things could have happened. Like, I could have had a baby.
baby or gotten married and I didn't and now I feel like I'm 50 and I have the whole world ahead of me.

Speaker 8 Like I've never been more excited to get through a test, you know? But these girls are very important people in my lives and they are my children.

Speaker 8 I think of them, you know, I would do anything for them. So yes, it was important for me to share that because when I'm, whenever I'm writing books, I'm like, what have I

Speaker 8 candid about my life? I'm not

Speaker 8 precious about my personal life or anything. I never want to be that way.
And I'm not very private. So I'm like, what can I share that I haven't shared?

Speaker 8 And I was like, so that was, that's something that people don't really know about how many children are in my life and how many children I really do care for and have in my like your nieces and nephews?

Speaker 8 Well, my nieces and nephews are one thing.

Speaker 8 They're related to me, but so many people outside that are not related to me whose lives I'm able to make big contributions to because I am single and because I am child-free, I have the bandwidth to help even more people than I would probably help if I only had my own family.

Speaker 8 And that's something that, you know, people don't talk about. When you are child-free, it opens you up to really be helping the world in a bigger way.
You can make other contributions.

Speaker 8 you know your value comes from a multitude of things not just being a mother or a wife there are many other ways to contribute so I'm glad so many women are having honest conversations about procreating and that it's not for everybody because it's fucking not you know some people aren't good at that yeah so it's good

Speaker 8 to be good you I'm good at helping out right you know I'm good at being a big sister and helping push and making sure picking people up but I don't need to be a parent you know any dog of mine will tell you right it is you seem like an excellent dog owner.

Speaker 8 Well, I mean, I have an excellent system in place. I'm not the best dog owner.

Speaker 8 I'm not the one doing all of the things, you know, and it's even for a dog. So imagine how I would show up for a real person.

Speaker 3 You do wear them on your back.

Speaker 8 Yeah, I ski with them when I need to and my bikini for my birthdays every year. So they're good for that.

Speaker 1 But no, I love my ski. You did this year for that.

Speaker 8 Where did you do this? I did that on Soldier Mountain in Idaho this year with like 25 women. I was like, get me 25, 50-year-old women and let's all ski together.

Speaker 8 So we took a little LSD and we all skied.

Speaker 1 Yeah. Yeah.

Speaker 2 In bikinis.

Speaker 8 In bikinis, bathing suits. Yes.
Yes. It was very joyful.

Speaker 1 Was it? Yes. Yeah.
Absolutely. I noticed you didn't have to be a skiing.

Speaker 8 I mean, it's very exhilarating walking.

Speaker 1 I can ski. You can ski?

Speaker 3 Yeah, I'm not skiing in a bikini.

Speaker 8 Why not?

Speaker 3 It's not for me. It's not for them.

Speaker 8 We're doing it in Palisades Tahoe Friday. We're doing it for Gold Bond.
We're doing a ski event that was inspired by my birthday videos.

Speaker 8 We're going to break the Guinness Book of World Records in Palisades Tahoe Friday, March 14th. And anyone can sign up.
Men, women, snowboarders, skiers. We're doing it.
In bikinis? In bathing suits.

Speaker 8 Oh, good. That's good.

Speaker 1 Any bathing suit you want.

Speaker 3 Oh, interesting. Okay, now.

Speaker 3 So

Speaker 3 one of the things you said, the book is about female sisterhood togetherness.

Speaker 3 Let's stick together and be empowered by others.

Speaker 3 And you write, the admonishment and disdain that comes in response to women's relationship with herself is a great reflection of how slow and unchanging our society is. Talk about that a little bit.

Speaker 3 You say what you want. You talk about loving drugs and alcohol.
You ski topless. You never want to get married and have kids.
You're essentially J.D. Vance's nightmare.

Speaker 3 Talk a little bit about what you're talking about here, the greatest reflection how slow and unchanging society is.

Speaker 8 It's just like men are upset that women don't, I mean, those types of men, I understand there are, you know, my type of men that understand why we would make that decision, but those types of men that want to keep women at home and being mothers and, you know, not having career, like that's just so antiquated and it's so slow and it's so boring.

Speaker 8 We're so bored. You know, I think the political situation we're in is a direct reflection of the fact that men are so scared of women.
Like, why are you acting like this if they're not?

Speaker 8 Why would you overturn Roe v. Wade after the Me Too movement? You know, that was a direct correlation, in my opinion.

Speaker 8 I think that, and women aren't going anywhere. And men, the men that stand with us aren't going anywhere.
So this is a blip of really unfortunate history in our country.

Speaker 8 I can't believe we've had to go through, we're going to have to go through this for a second time and probably worse.

Speaker 8 But I don't have any hope lost about the success of women and the contribution. Women are more powerful and more independent than we've ever been.
And that isn't going to change.

Speaker 3 Do you, what do you think of, you know, my other podcast partner, Scott, talks about the crisis of young men and men right now. Do you think they're in a crisis or do you think about it at all?

Speaker 8 I do.

Speaker 8 I was on a plane yesterday with a really young, I think there's a new generation of young, this boy, he was on this plane, this 16-year-old boy, and he asked if he could put tiger balm on his knee if it would but the smell would bother any of us.

Speaker 8 And I was like, I want to have sex with you. Like,

Speaker 8 I know, I'm not having sex with a 16-year-old, but you know what I'm saying? When he was older, when he gets older, maybe I do want to have sex with him.

Speaker 8 But that was just a nice indication of how conscientious, and I'm noticing young men like that.

Speaker 8 When I'm talking to my friends' children, like they're very engaging and they're more confident and they're smarter than when we grew up.

Speaker 8 So, I feel like this new generation, they're very, they're, they're, you know, woke in the right way.

Speaker 8 They're not, it's not a cancerous woke where everyone's like, it's conscientious and they're compassionate. And they, and so I'm very hopeful about our young people.

Speaker 8 I think they're, they're a lot smarter than we're giving them credit for. Agreed.
Do you, what do you

Speaker 3 attribute attraction to Trump though with a lot of young voters?

Speaker 8 I don't understand the attraction to Trump with a lot of young voters. I don't know if that is the,

Speaker 8 I mean, I can't speak to that. I can only speak to

Speaker 8 the fact that we're going to see, you know, this, how this all shakes out. People aren't going to be pleased with this when the next midterms come around.

Speaker 8 No one, Trump is not out for anybody but rich people, as we all know.

Speaker 8 So it's like everyone who voted for him in the hopes of something else or some aspirational hope of a better life, a better economy, you know, they're wrong. That's not going to happen.

Speaker 8 The opposite's going to happen. You know, the people who don't have money are going to suffer even more.
And so,

Speaker 8 you know, I don't know how to answer why anyone votes for Donald Trump. I don't get it.

Speaker 3 So a lot of people did. Well, one of them was the idea of a better life, right? That the prices would be better, that there's more opportunity.

Speaker 3 And even though the economy was good, they didn't feel it.

Speaker 8 But also, any economist will tell you that you're finding an economy, an economy hits like four to eight years after the first president.

Speaker 8 You know, Biden was working off of Trump's economy, and Trump is working off of Biden's economy. But people are so fucking stupid, they don't even understand that.
I don't get it. It's so obvious.

Speaker 8 You don't implement things into the economy and it has an impact right away. To the stock market, it does, but not to the economy.

Speaker 8 You know, those are, I mean, some things, but a lot of things take a lot longer.

Speaker 3 Talk a little about money because the tax cuts will help people like yourself, right?

Speaker 8 No, I don't need the help. I'm happy to give my money to the people that need it.

Speaker 3 But when you talk in the book about

Speaker 3 your parents as a financial hurricane, and earning money is important to you, and

Speaker 3 you've done well all throughout your career in that way. When did you first realize the importance of understanding money for yourself? Because

Speaker 3 you discuss it in the book quite a bit.

Speaker 8 I mean, I don't know if I understand money, but it's nice to have. It helps, you know, it helps a lot.
It's nice to be able to help other people with it. It's nice to be able to live a life that

Speaker 8 affords me the possibilities to see the world. Of course, I want to have a nice life.
I like money.

Speaker 8 But seeing my parents struggle financially, we weren't weren't poor, but we weren't wealthy.

Speaker 8 And I, you know, there were like phone bills would be, phones would be turned off, things like that, made me feel very insecure.

Speaker 8 And I definitely felt from a very young age that I wanted financial independence. And I never wanted to rely on a man or a partner for that.
Now I wouldn't mind a little help, commingling some funds.

Speaker 8 You know, I'm like, I support a lot of people. So I'm like, can I get some, you know,

Speaker 8 can I get another, you know, I'd like a double family income, but you know, that's hard to do if I don't want to get married. So

Speaker 8 I take the responsibilities on, and then I have to hustle.

Speaker 3 I told her to take one from the team and date Elon Musk.

Speaker 1 Elon can bring him back.

Speaker 8 Yeah, I'm not that much of a teammate.

Speaker 8 I don't think I can do it. I mean, there's a lot I would do for this country, but having sex with Elon Musk is not one of them.
I can't.

Speaker 1 I can't. It's just an idea.

Speaker 8 I would do so many other things, though, you know, for the country.

Speaker 8 Such as? I mean, I can't think of anything. You're the interviewer.
You have to figure out what I'll say yes to and what I'll say no to, Kara.

Speaker 3 I think that's a good idea.

Speaker 8 But I mean, Elon Musk is just one, that is above my pay grade.

Speaker 3 Okay. He has a lot of money.

Speaker 8 I know, but that's not, I can't.

Speaker 1 Yeah. Yeah.
All right. Yeah.

Speaker 8 But you should try it.

Speaker 1 You do it.

Speaker 8 Why don't you do it, Kara? Does anyone here want to do it? No.

Speaker 1 No. Wow.
That's amazing. All right.

Speaker 3 So one of the things, though, in the book, you are very ambitious from an early age. I love the scenes of...
Very vicious? No, no, no, ambitious.

Speaker 1 Ambitious, yes. Yes.

Speaker 3 Somewhat vicious because you cut your sister or your brother off working for you.

Speaker 8 My sister, I fired her. I opened a lemonade stand.
My sister wanted to partner with me on it. And then I realized pretty quickly lemonade was not going to be a big profit margin.

Speaker 8 So I opened up a hard lemonade stand serving alcohol to the parents of the children and then children who were 10. They could also get a drink.
And then I made a lot of money.

Speaker 8 And then I had to cut, I had to lean out my staff. So I cut my sister.
And then

Speaker 8 I hired another 10-year-old named Nelson and he was my bar back. He made the drinks.
And in the first week we were 10 years old, we made $359 at our hard lemonade stand.

Speaker 8 And I gave Nelson his commission, which was $3.59.

Speaker 8 And Nelson thought he had hit the jackpot. He's like, oh my God.
I said, stick with me, brother. I will show you the way.

Speaker 8 I haven't seen Nelson

Speaker 8 since that lemonade stand,

Speaker 8 but I do now with my book, in conjunction with my book, I partnered with this brand Owl's Brew, and I made my own Chelsea Handler's vodka lemonade. We have three flavors and it's so delicious.

Speaker 8 So my dreams all came true. So you're still in the business.

Speaker 1 So I'm still in the lemonade business. Yes.

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Speaker 3 So, where does that entrepreneurial drive come from? Because you have been very entrepreneurial as a career compared to a lot of people, I think.

Speaker 8 Yes, I'm very, I have a lot of authorship over what I do. I don't really like answering to people.

Speaker 8 And I've managed to carve out a career where I don't have to answer to a lot of people.

Speaker 8 Even when I did really have to answer to people, when I worked at companies, I didn't. You know what I mean?

Speaker 3 Yeah. Oh, I know.
Yeah.

Speaker 8 So, and everyone is aware of that. So, no, I'm aware.

Speaker 1 I'm the same one. Oh, yeah.
Okay. Good.

Speaker 8 I thought you were saying everyone knew about me. I'm like, I guess they probably did.
But

Speaker 8 no, I'm good at being my own manager. I mean, I have my podcast.
I have my books. I tour my stand-up.
I have my residency in Vegas. I do everything the way I want to do it.

Speaker 8 I'm going on a European tour this year, like my first in years, you know, once the election was announced.

Speaker 8 I'm like, I guess I'll go to Europe and spend some time apologizing to our allies, our European allies who we love so much. Thank you for your support over all this time.

Speaker 8 So I'm going to go do some public service work over there. And

Speaker 8 yeah, I'm very

Speaker 8 in Canada. I have a house in Canada, yes.
That's a backup plan once we become the 51st state. I don't know what kind of plan that is, but

Speaker 8 yes, I'm very ambitious. I've always wanted to have a big, full life, and I feel like I am having.

Speaker 8 You have to decide when to not do things, when to stop doing them well if I'm just doing something for a paycheck and I don't feel any sort of creative stimulation I don't do it I learned that lesson a long time ago not to just take money because it's offered to you you have to be a little bit discerning about what kind of

Speaker 8 what you want to put out there and I I'm reliable in the sense that I'm always elevating myself and there's an evolution it's not just the same shtick over and over again it's a more evolved shtick and I'm growing up I'm 50 years old now.

Speaker 8 So I have different things to say. And my ambition is different.
I'm on solid ground. I've been around the block so many times.
I know myself. I know what I'm capable of.
I know what my strengths are.

Speaker 8 And I'm not shy. And I'm not apologizing about any of it anymore.
And I'm not trying to people please. I don't get caught up in other people's opinions.

Speaker 8 And yeah, you can say I've always been like that, but I really feel like that now. I'm impressed with me now.

Speaker 8 So that's all I need.

Speaker 3 That's true.

Speaker 3 So, but one of the things you talked about, you've been, as you've been successful, you felt like you weren't grounded and you were going to therapy in the book, but you lost confidence and you were second guessing yourself.

Speaker 3 You talk about this and you had a panic attack. Tell us a story of how you realized therapy had become part of the problem.

Speaker 8 Therapy didn't, it wasn't, it didn't become part of the problem. It just, it's so,

Speaker 8 when you go to therapy, it's so ironic because to get, I went to therapy to get my head out of my ass. I was, I felt too self-involved and self-absorbed.

Speaker 8 But then you go to therapy and you have to spend hours ad infinitum talking about yourself.

Speaker 8 So it's kind of hard to get away from yourself when you're, but you, that is the process to understand and gain some self-awareness and reflection and understand why you do the things you do.

Speaker 8 It's not the most pleasant process for anyone here who hasn't been to therapy. I'm assuming many of you have and you understand what I mean, that it's it's dirty.

Speaker 8 You know, you find out ugly truths about yourself and it's up to you to decide if you want to step it up and level it up and become the better version, you know, the 2.0 version of yourself.

Speaker 8 And I did want that. I wanted to learn and grow and be stronger and more compassionate and patient with idiots.
You know, like I want to be patient. When somebody's stupid, I want to be nice to them.

Speaker 8 I don't want to go, why are you so fucking stupid? You know what I mean? I wanted to learn that and I have learned it. Now I'm nice to stupid people.
Really?

Speaker 1 Yeah, I have patience.

Speaker 8 I understand that something may have happened to them. You know,

Speaker 3 I'm still stuck in.

Speaker 1 Yeah, it's hard. I know.

Speaker 8 I don't want to leave there.

Speaker 1 Yeah. Yeah.

Speaker 8 So, you know, ignorance and stupidity, two two different things sometimes.

Speaker 3 Yeah, that's true. So that's true.
But after the panic attack, you decided to spend more time alone. Yes.

Speaker 3 And you began rereading self-help books that you could find. And you write that most self-help books pretty much say the same things, but certain ideas resonate.
What stuck with you?

Speaker 8 The idea of putting out positivity and energy, like your energy field. You know, I always thought that was kind of annoying to hear about.
And then you realize that it's scientific.

Speaker 8 Actually, when you have positive thoughts, you're stronger, you're healthier, you're optimistic you have a different look on your face and you attract more positivity and there's a magnetism there and that is true and it's scientific and your energy is not imagined you know it's not in my anyone's imagination so learning about that in a scientific way was very helpful to me because it's the power of positive thinking it's the power of being optimistic in the dark and not going down a wormhole like you know the first trump presidency for instance i let it take me down and I let it steal my joy and I'm not going to do that again.

Speaker 8 You don't get my joy again.

Speaker 3 How do you prevent that? A lot of people, I get contacted by people all the time.

Speaker 3 What am I going to do now?

Speaker 8 I know. I know you do.
I was just sitting backstage asking you the same thing. What do we do now?

Speaker 8 But we'll figure out what we're going to do. It's just, it's one foot in front of the other.
Everything is happening so fast.

Speaker 8 I don't doubt that we're going to get organized and figure out what the hell to do.

Speaker 8 I'm right. I'm ready.
Let's go. I mean, don't did anyone vote for Elon Musk to be the president? I mean, can't we come together, Republicans and Democrats, and say we don't want that?

Speaker 8 Can't we agree on that at least?

Speaker 3 We can. We can absolutely.

Speaker 3 Do you feel political right now? Do you feel like you're in a like, because a lot of people want to just check out?

Speaker 8 Yeah, I relate to that a lot. I feel a little disassociated right now.
I mean, it's hard. You know, you're promoting something and everything is happening in the background.

Speaker 8 It's like two different elements of my life. Like, I want something, I'm promoting something that's very joyful and happy.
I have my stand-up special coming out, another joyful, happy thing.

Speaker 8 And with this as the backdrop, and it makes me realize like, you know, what my purpose is here is to bring a little bit light and levity and remind people to double down on your love to others and kindness and compassion to all of the groups that are being targeted because people are really scared.

Speaker 8 And I hate that. I don't want people to feel that way.

Speaker 8 So what I can do in this moment is to be strong and be a beacon of light to people that feel hopeless and let them know they're not alone and that we're together. We're going to be together.

Speaker 8 And we have more people than they do. I know that.
I know more people are good than they are, you know, terrible. I believe that.
And I don't believe all Republicans are terrible.

Speaker 8 I just think, you know, I do think Trump is terrible.

Speaker 3 So let's pay back to the parenting advice, which runs throughout the book, actually. You pay for your extended family's vacations.
It sounds like a lot of fun.

Speaker 3 You noticed the kids were being entitled. And so you wrote a letter where you reminded them of some basic etiquette, which I'm going to have you raise my kids.

Speaker 3 You wrote, do not consume copious amounts of alcohol that you did not pay for, leaving the adults with no alcohol on multiple occasions. This is not a way to get invited back.

Speaker 3 This is solid advice, I have to say.

Speaker 3 How did your siblings react to you?

Speaker 8 Well, it's their fault. Any child's behavior is their parents' fault.
So, that letter was to my siblings as well.

Speaker 8 It was a letter after a vacation where the kids just treated this house that I rented on Martha's Vineyard that was so beautiful and so well-appointed.

Speaker 8 And these people did not want to rent their home. And my brother, my nieces and nephews were just so spoiled and entitled.

Speaker 8 And then I realized I was part of the problem for providing them with these vacations every year, wanting to spoil them, wanting to like, you know, show them how special life can be and how, you know, great it is to be successful.

Speaker 8 And then I realized, oh, I'm part of the problem. So then I started taking the kids away without their parents.
Oh. And so I can tell them how it is.
And that's been going well, too.

Speaker 8 I mean, my siblings don't like it because they're not going on the trips anymore, but

Speaker 8 I blame it on their bad parenting. Right.

Speaker 1 Okay.

Speaker 8 so they're gonna write a book called hot parenting tips hot well let me have some that you know how to talk to kids maybe because you've actually taken parenting classes i took parenting classes i've never taken a parenting class i took online parenting classes for the my ex-boyfriend's daughters okay so i wanted to be i wanted to understand children better and and you know i thought you could you know threaten them and that would or you could bribe them i'd be like if you do this i'll give you this and it's not about that at all it's about being consistent and it's about meeting their moments and when they're angry and they're mad, you never match their anger and their madness.

Speaker 8 You just show up with love. Like, oh, you're in a terrible mood.
I still love you. I'm still sitting right here.
I'm not going anywhere. So you can be as mad as you want, but I love you.

Speaker 3 So, what are the top three mistakes you see parents make?

Speaker 8 Well, first of all, people don't see their own children clearly. They are so biased.
So you can't parent when it's your own child because you can't see how damaging it is.

Speaker 8 So good luck, I guess.

Speaker 8 No, but just, you know, treating children like human beings beings instead of like children or adults, like really meeting them where they are, being on their level.

Speaker 8 If they're on the ground, get on the ground, you know, and sit with them and be interested in what they're talking about. Everyone just wants to be seen.
Every person wants to be seen.

Speaker 8 That's really the truth of the matter. And when you feel seen, then you feel like yourself and you don't feel judged and you can express yourself.
And that's what we want.

Speaker 8 We want everyone to be, I want everyone to have like an injection of confidence and feeling seen. Like that really makes a difference in a kid's life.

Speaker 3 It does, absolutely.

Speaker 8 I had one teacher who just told me that I was going to be the shit.

Speaker 8 Her name was Mrs. Sheckman.
She died last year in Florida. And she made me believe in myself.
And I was the youngest of six kids. So there was a lot of neglect.

Speaker 8 And there was, I mean, it wasn't a terrible childhood by any means, but there was a lot of neglect. They didn't pick me up from school.
They'd forget about me all the time. Well, you were number six.

Speaker 8 I was number six. Yeah.
And so I don't know why my mom didn't know about birth control, but she did it.

Speaker 8 And

Speaker 8 my teacher really instilled in me like what I was going to amount to and that I was going to be something.

Speaker 8 And I will never forget those words of encouragement. So, when I look at any young child who's been neglected, I want to be that person for them.

Speaker 3 You should write a parenting book.

Speaker 8 I know, I just said that, Carol.

Speaker 1 I know, you're cool. You're pay attention.
I know, but really, you should.

Speaker 8 I'm sitting right across from you with a microphone.

Speaker 3 I'm not even listening, but you're not actually doing it right now.

Speaker 8 No, I don't have, I'm not writing a book right now. I'm promoting this book.
Give me a minute.

Speaker 1 I'm like, Jesus, my God,

Speaker 8 how much can I do? What do you think I am? You? That's true.

Speaker 3 You also write openly about your love life, and you talk in the book how your relationship with comedian Joe Coy changed the way you look at love, even though it didn't work out.

Speaker 3 And although you want to find romantic love, you thought to yourself, men are becoming unfuckable.

Speaker 3 Talk about that.

Speaker 8 I'm still having lots of sex with men, so they're not completely unfuckable.

Speaker 1 I'm not going to read about that.

Speaker 8 And no, it's not all men. I don't want to be, I'm not a man-hater.
I just, we understand what's happening in this world, and it's pretty obvious. And I'm, yes, I'm very, I, I like a variety of men.

Speaker 8 I like men in my life. I'm not a settle-down kind of girl.
I don't see that happening for myself. Never?

Speaker 8 I mean, I'll never say never.

Speaker 8 I mean, I, you know, whenever I'm in a relationship, I think, oh, this would be nice. And then eventually I'm done with that relationship.
So I'm just not that type of person. I'm not a

Speaker 8 gonna get married, spend my life with someone person. I like a little bit of, I like a lot of alone time.
And then I like to come together and, you know, and I just have different desires.

Speaker 8 I used to think that something was wrong with me and now I realize I'm totally normal, that a lot of people feel that way. And so I'm saying it because I want people to know you're not alone.

Speaker 8 If you feel that way, you don't have to find a soulmate. It's okay.

Speaker 3 But in a lot of ways, you're still the same person. Tell the Woody Allen story from this book.
It's the best. It's one of the best.

Speaker 8 Woody Allen, I went to a dinner. I was with Katie Couric.
Katie tells the story. She told the story differently, and I'll tell you how she tells it.

Speaker 8 But Katie and I went to this dinner, and there was all these random people in New York City, and I'm sitting at a cross, and there's two empty seats across from me, and I'm up against this wall in this restaurant.

Speaker 8 And in comes Suni Previn and Woody Allen, and I'm like, oh, no. Like, I can't do this.
There's no way that I will get through this.

Speaker 1 Were you aware of this?

Speaker 8 No, I didn't know they were coming. I saw them walking the restaurant, and then they're walking toward the table.
And I'm like, no, no, no. And I'm kicking Katie under the table.

Speaker 8 I'm like, oh, no, I'm going to have an outburst. Like, I'm going to.

Speaker 8 There's no way you can seat me across from woody allen and she's like can you wait and i'm like wait for what and she's like can you at least just wait to the end of the dinner and i was like i could try

Speaker 8 and i mean i did i was like that's a fun experiment to like hold myself you know to exercise some sort of patience and so i did i waited and i waited and i waited and i was asking him like i'm not fake at all and i was being so fraudulent i was asking him questions about all the movies he directed and then i mistakenly thought he directed annie yeah and i was asking him about that and he was answering the questions, which just doesn't make any sense.

Speaker 1 It was Annie Hall, not Annie.

Speaker 8 I didn't say Annie Hall. I was asking about Annie, and he was talking about Annie.
But of course, I mean, you know, of course he was because that's another little girl. Anyway, he

Speaker 8 at the end of the dinner, they passed around Blackberry Cobbler. The server came in and plated everyone's Blackberry Cobbler.
And I, and then I was like, you're going to get it now.

Speaker 8 And then Woody Allen took a bite of his Blackberry Cobbler, and I leaned in and said to him and Soon Yee, so how did you two meet?

Speaker 8 That's great. I slept like a baby that night.
I really did.

Speaker 8 I was like, and then Katie was retelling the story, Katie Kouric, and she was saying, she's like, I guess Chelsea forgot how they met because she asked them, how did they meet?

Speaker 8 I'm like, no, Katie, I didn't forget how they met. That was very pointed.

Speaker 8 Oh, Katie. Yeah, I know.
Katie and I go back and forth on this all the time. Like, I just forgot how they met.

Speaker 3 Yeah.

Speaker 3 And the reaction?

Speaker 8 He spit Blackberry Cobbler out of his mouth. He He was laughing.
And then I got up. And then she's kind of out of it, Sunyee.
I don't know what her story is, but she wasn't very present.

Speaker 8 Like she was just kind of all over the place. So I don't know if she heard me or not, but I was leaving anyway at that point.
I just had to say that before I did leave.

Speaker 8 And then Katie was like, time to go.

Speaker 3 So he laughed at your job.

Speaker 8 Yeah, he did laugh. He did laugh.
But, you know,

Speaker 8 I wasn't laughing with him. I was laughing at him.

Speaker 1 Okay.

Speaker 3 Yeah. I love that story.

Speaker 1 I wish I could do that. I'm going to do that.

Speaker 8 Now you've taken you do that to people all the time.

Speaker 1 All the time. I do.

Speaker 3 I do. But that one is.

Speaker 8 Yeah. Thank you.

Speaker 1 I was proud of that moment. I wish I had.

Speaker 3 Well, I've never had that.

Speaker 8 I had a moment like that with Piers Morgan once. I was proud of that too.
What did you do to him? He was interviewing me and I just said, you're such an asshole. You know, he was reading his phone.

Speaker 8 This has been around the internet, so I'm sure some of you have seen this.

Speaker 8 And he's like reading his phone while he's talking to me.

Speaker 8 And I'm like, you're a terrible interviewer. Why are you inviting me on your show so you can read your phone?

Speaker 1 He's like, what? What?

Speaker 8 What? And he's like, well, maybe you're not interesting enough. I'm like, That's that's a you problem.
You invited me here.

Speaker 8 You have to ask me questions to so that I can answer them instead of reading the fucking internet, you loser.

Speaker 8 So that was good. That went viral.
I like that moment as well. He deserves that because he really is an asshole.

Speaker 3 Yeah, I would agree with you on that one.

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Speaker 3 So let's talk about the business of being Chelsea Hennon. A few things.
This is a seventh consecutive New York Times best-selling book, your publishing phenomenon.

Speaker 3 You grew up reading Moby Dick and a bunch of other books as a child.

Speaker 8 My father forced me to read these big books when I was like eight and seven years old.

Speaker 1 They were so inappropriate.

Speaker 8 I read Anna Karenina by Tolstoy when I was eight. I had to give a book report in our kitchen.
And then I had to read Moby Dick.

Speaker 8 And then he made me read East of Eden by John Steinbeck when I was eight. I wanted to kill my father.

Speaker 8 I had nothing in common with any of my colleagues at school. I would go, they would be like Humpty Dumpty sat on a wall.
I'm like, which one, China or Berlin?

Speaker 8 I had nothing, no relatability to like six-year-olds.

Speaker 3 How do you think when you write, you know, sort of about art versus commerce when you're writing?

Speaker 8 I don't, I don't think of,

Speaker 8 I don't think that if you're not being authentically who you are, if you're me and you make a living at being yourself, you have to be very honest and very, I have to show all the good, the bad, the ugly.

Speaker 8 That's what the people that respect me and are looking to consume my stuff are looking for is honesty. And that is what I base everything off of.

Speaker 8 I'm going to give you the honest truth of what's happening in my life right now. I'm going to make you laugh.
I'm going to hopefully inspire you. And I'm probably going to make you cry too.

Speaker 8 And I'm gonna do all of those things and I'm gonna be very intentional about it. It's not yes, I'm making a living, but I'm not I'm not for sale.

Speaker 3 Is there anything you don't share?

Speaker 8 I mean, certain people want to be private. So, you know, some people, I don't tell their secrets.
You know, I had, it took me a long time to understand that my stories are not always just my stories.

Speaker 8 They're other people's stories, private people. And not everybody wants their story, you know, over the loudspeaker.

Speaker 8 So I've learned to shroud people's identities and to be respectful of people who don't want to be in the public eye.

Speaker 8 So, you know, my relationships with men, for instance, I don't want anyone to even have to deal with what I deal with. People can't deal with that.
They wouldn't last two days, you know?

Speaker 8 So I like to keep like my romantic interests. Like now, I've had a public relationship.
Like, I hope I don't do that again.

Speaker 3 Right. Have another one.

Speaker 3 Yeah.

Speaker 8 I hope I don't date another public person.

Speaker 3 Okay. All right.
Besides the book, as you said, you have a line of vodka, lemonades. You've got a stand-up special.

Speaker 8 Netflix. My new stand-up special comes out March 25th.
25th. It's called The Feeling.
It's called The Feeling. Yeah, The Feeling.

Speaker 3 You've got a podcast, dear Chelsea, this European tour. What are the real money makers here? Stack rank them and give me a sense of how each fits into your overall business strategy.

Speaker 1 Oh, well, Kara. Why not?

Speaker 8 Because I don't know, honestly. I don't know.
You don't actually know? No, I mean, I have to really think about how much money I make off of it. I make a good living.

Speaker 3 Right, I get that. But what does best for you? That's surprising.

Speaker 8 Touring, probably stand-up.

Speaker 3 Yeah.

Speaker 8 You make the most that you make cash and you go around, you know. I mean, not European, right? That's kind of just, you know.
But in America, you know, you do a hundred shows, you make a lot of money.

Speaker 3 And that's your best still remains. Has it changed over time? Is podcasting or anything?

Speaker 8 Podcasting, I make a lot of money doing that too. I mean, I've been doing my podcast for a long time, but touring is where the, you know, you make the most money.

Speaker 3 Are you surprised by how well comics are doing online?

Speaker 1 Yeah, I love it.

Speaker 8 I mean, look at how many female comics are coming up. I mean, I have so many amazing, fierce female comics.

Speaker 8 They're all here at the festival too, that are coming up, that open for me, that I see, that I have specials out. Like it is turning into a very level playing field.

Speaker 8 We are not there yet, but it is turning into a level playing field, a more level.

Speaker 3 Do you lean into online more? Like YouTube specials, things like that? Obviously, this is on Netflix, which is a streamer, but how do you think about that?

Speaker 8 For me personally,

Speaker 8 I just, you know, that's a Netflix. Netflix is the place to be right now for a standard.

Speaker 3 It used to be HBO.

Speaker 8 It used to be HBO. Yeah, then it was Netflix.
And now all these other people are trying to, but it's still Netflix. That's where people go to watch specials and it's in the most households.

Speaker 8 So if you want an international business, you want to be on a platform that has the most, you know, households, obviously. And I have a long relationship with Netflix.

Speaker 8 I've been working for them since they started.

Speaker 8 I did their first talk show. I did a bunch of documentaries for Netflix.
I did ayahuasca on Netflix.

Speaker 8 Yeah.

Speaker 8 I did one about, you know,

Speaker 8 white privilege. I've done a lot of really interesting things at Netflix.
And so we have a great working relationship. And I'm happy to do my stand-up specials there.

Speaker 8 And any other business I do, any other TV stuff I might have coming down the road, that's not, you know, I'm not exclusive to Netflix.

Speaker 8 Then I would go pitch it to other outlets, and you find the best partner.

Speaker 3 The stand-up special, you get some topics covered in the book, but it's tonally, it's edgier.

Speaker 3 How do you, do you think the audience that reads your books versus the one that watches you in stand-up, do you think you have... an overlap there with the audiences?

Speaker 8 I'm sure there's an overlap.

Speaker 8 I mean, you know, some of this, there's overlap in some of the material because when you're writing a book, you can really set the scene, you can set the characters, you can set the dialogue, you can get into real details about certain situations.

Speaker 8 And stand-up, your driving force is the punchline and the joke of the story and the funny. But they're both, you know, I'm a storyteller.
I'm telling my personal story.

Speaker 8 So there's definitely, you know, the Cuomo,

Speaker 8 my almost penetration. with Governor Cuomo.
Yeah, that was a good stand-up and in the book.

Speaker 3 Are you going to go back to that now that he's running for the family?

Speaker 8 Now that he's the mayor? That is running for mayor? No, no. I'm not interested in Andrew Cuomo anymore.
Okay. But I was for a hot minute when everyone else was during COVID.

Speaker 3 I like that you kept texting him even though there was no response.

Speaker 1 I did too.

Speaker 8 I liked that. I was doing that too.

Speaker 8 It was funny. My family's like, you have no shame.
I'm like, who gives a shit? You know what I mean? This is going to be a really funny story if that's what it is.

Speaker 3 You did one with President Bush saying, I'm good enough for a president, but not a governor.

Speaker 8 Once I was at President Bush's house at Kenny Bunkport, I took a selfie with him and sent it to Andrew Cuomo, and I said, good enough for a president, but not good enough for a governor.

Speaker 1 yeah

Speaker 8 what if he texted you right now Andrew Cuomo yeah oh I don't give a shit about Andrew Cuomo anymore I'm long I mean that's the thing about heartbreak you know you forget about him I mean out with the old in with the new I've had my heart broken many times since well you missed that bullet yeah I did I dodged that bullet as my sister says mom is up our mom our dead mother is upstairs in heaven making sure I don't get canceled I'm like really by cock blocking me on the ground right that's true that was a good one though yeah She's not wrong.

Speaker 8 My mom is protecting me.

Speaker 1 Yeah, that's true.

Speaker 8 I mean, if I had been with him, I might have gotten canceled too.

Speaker 1 Yeah.

Speaker 8 Yeah. But now he's back.

Speaker 1 So, yeah, there you have it. There you go.

Speaker 3 No one gets canceled, really.

Speaker 3 So streamers are famously guarded with their data, which gives it a lot of leverage.

Speaker 3 I recently interviewed Ben Stiller about severance, and he talked about how strange it was to essentially fly blind when you're negotiating with streamers who have no data on viewership.

Speaker 3 How do you think about it? Do you do that yourself or do you let your agents?

Speaker 8 I get data on my viewership.

Speaker 8 Yeah, they give it to you. I mean, I think

Speaker 8 they play games when you're negotiating to not give it to you. Or they underplay it, maybe, but I don't know.
It's kind of information that's accessible at this point.

Speaker 8 You can't really, there's nothing secret anymore.

Speaker 3 Let's end up talking about politics again last time.

Speaker 3 How do you tackle him? Comedians tackle him now.

Speaker 1 Trump? Yeah.

Speaker 8 I mean, Trump is just the same as he's always been. He's a buffoon.
You know, he's an orange orangutan. I mean,

Speaker 8 what is there more? There's nothing, there's no new information.

Speaker 8 It's the same old shit. You know, you have to tell him he's wonderful and great, and then he's nice to you.

Speaker 8 And watching world leaders, like watching him threaten the world and make enemies out of our allies is horrifying. That's not what we want.

Speaker 8 We don't want to be, we're not in bed with Russia. That's not what America stands for.
America has not accomplished what we were set out to do.

Speaker 8 This democracy and this dream of democracy, we still have not accomplished it. It's an idea of what could be.
We've never been it. It's the idea.

Speaker 8 So we are still going to go in that direction of that idea.

Speaker 8 You know, after these four years are over, I hope we're still in a position that we are still going after the ideal of Americanism and what that means, and that we find some common ground with Republicans because this doesn't work anymore.

Speaker 8 It's like this fighting and this hatefulness is not getting us anywhere. So we have to figure out what the next solution is.
or the next step for a solution is. And I don't have the answer to that.

Speaker 3 So when I last interviewed, you said we're having a social justice and racial justice movement. That's clearly over.
We seem to be in the middle of a different thing.

Speaker 3 Many comedians, especially white male comedians with podcasts, are full-on Trump supporters. Trump adjacent.
I'm talking Joe Rogan, Theo Vaughn, Tim Dill, and Andrew Schultz.

Speaker 8 I just did Theo Vaughn's podcast. And we did not discuss Donald Trump.
Right. It didn't come up once.
Wow, interesting.

Speaker 8 I was totally fine if it had come up, but he didn't bring it up because, obviously, why would he?

Speaker 3 Do you think some are scared? You hosted the Critics' Choice Awards. You basically implied Melania Trump was a sex worker.
I think that's the new word now.

Speaker 8 But Trump is a very good idea. It's a flight attendant.

Speaker 1 She's a flight attendant.

Speaker 3 But Trump was barely mentioned at the Oscars. Do you think Hollywood is going to meet the moment? Comics are going to meet the moment?

Speaker 8 Yeah, I don't think, I think we're kind of, I think Hollywood's kind of doing its own thing and moving forward in its own thing. And Hollywood has a big impact on social justice.

Speaker 8 And it has a big impact on what we see and the stories that are being told and representing all of the people that are being targeted by this administration.

Speaker 8 So I think Hollywood is kind of a nice antidote to this administration in many ways.

Speaker 3 But do you see pulling back or are you scared in any way to do that?

Speaker 8 I mean, I'm sure I'm a target, but

Speaker 8 am I pulling back? No, I really.

Speaker 3 Clearly not.

Speaker 3 No, I'm not going to pull back.

Speaker 8 I mean,

Speaker 8 I'd like to... I'd like to make sure when I'm making comments about these things that

Speaker 8 there's a point to it, not just sounding off and bitching and moaning, because that I realized during the last administration, how futile that is.

Speaker 8 And you're wasting your words, you know, and your energy.

Speaker 8 So it's important to be like, it's important to have a mission and understand when to speak up and what to say when you're speaking up and not to just be screaming the whole time.

Speaker 3 So last question. Semi-clad skiing is your birthday tradition.
Any working, now that you're 50, happy belated birthday. Thank you.

Speaker 3 Are you working on any new traditions?

Speaker 8 New traditions? Yeah.

Speaker 3 No. You like skiing naked?

Speaker 8 I ski in bathing suits a lot. I'm not naked anymore.
My nephews asked me to not do that again.

Speaker 8 And I said, it's very, I said, that you guys should take it as a compliment that your friends are talking about my body in that way. Like, I'm very relevant to your teenage friends.

Speaker 8 And they're like, we don't want to hear them talking about your boobs. And I'm like, okay, this is exactly why I didn't have children, so that nobody could tell me what to do.

Speaker 8 But now I have to, you know, they're my nephews. I don't want them to be embarrassed about me.
So I put my top on. I don't ski naked anymore.

Speaker 8 But I do ski in a bathing suit with a joint and a margarita every birthday.

Speaker 3 Yeah, and I think it's a great you're going to continue it into your singing.

Speaker 8 Singing the song of freedom for women, you know, everywhere. It's like, come on, I'll have what I'm having.

Speaker 3 What's the title of your book that you released on your 60th birthday?

Speaker 8 The wheels are off, but the train is still going.

Speaker 1 I don't know.

Speaker 3 All right. On that note, Shelsey hands.

Speaker 8 Thank you.

Speaker 8 That was fun, Carol.

Speaker 2 On with Kara Swisher is produced by Christian Castor Rousselle, Kateri Yoakum, Dave Shaw, Megan Burney, Megan Kunane, and Kaylin Lynch. Nishat Kerwa is Vox Media's executive producer of audio.

Speaker 2 Special thanks to Kate Gallagher. Our engineers are Rick Kwan and Fernando Aruda, and our theme music is by Trackademics.
If you're already following the show, you get a skiing invite from Chelsea.

Speaker 2 LSD, optional. If not, you're stuck on a lift with Piers Morgan.
Go wherever you listen to podcasts, search search for On with Kara Swisher, and hit follow.

Speaker 2 Thanks for listening to On with Kara Swisher from New York Magazine, the Vox Media Podcast Network, and us. We'll be back on Monday with more.

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