Under Cover Upper East Sider (w/ Jill Kargman)

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1:58Haley: Want to try it out for yourself? Go to GlossGenius.com and use code financial for 50 % off your first two months of a premium plan. I mean, I always say Ivy had said, why are you the only mom at school without red bottoms on your shoes? She was like two. I didn't sell my TV show till I was 39. Getting a facelift is like getting a pedicure now. This is Financial Tea. What's up, zippers? Welcome back to Financial Tea. This is a podcast where I teach you how to build wealth with a side of market drama, money scandals, and of course, financial pop culture, because that's what we're all interested in, right?

2:38Haley: And today, we have my friend Jill Kargman in the house. She is a New York Times bestselling author. She's an actress. She's a New York icon. She's a filmmaker. Baker. She's an Upper East Sider. And most of all, she's here in the studio. So Joe, welcome to the Financial Tee. Thank you, Haley. It's so exciting. And I love Brooklyn's and I love Dumbo. I know you're in Dumbo. It's crazy. The F train shits me out right in my neighborhood. I love it. I know. So easy. Pop on that. Yeah. Okay. So you're a public transport kind of gal. Oh, I live on the subway. What do you think are the traps that people get in in New York City where they like overspend money?

3:15Haley: Like obviously Uber. Yeah. Uber's the for sure. Like if I need to lean out finances, I'm cutting Uber. Yep. I mean, I feel like there's certain transportation splurges, like maybe airfare and stuff like that. I love travel. That's my biggest splurge because I don't have a country house. So we travel all over the world and that's where my money goes. Yeah. And I like, you hemorrhage money, but you're making, I'm, even though I'm a full Gen X or I'm 52, I have that millennial thing of experiential like life choices. And that's my splurge, but rather than like acquiring shit. You're like, instead of before I went K, I want 401k memories.

3:53Haley: Yeah, exactly. The memes before I am like worms meat. Obsessed. So besides like cutting Uber, like what else do you do as a New Yorker? Because it's an expensive place to live and you're like so New York. It's really expensive. And we both grew up here. Yeah. I mean, I can't cut this out because it's such a big part of my life, but going to restaurants. I mean, we go to restaurants so much. I don't cook. We order in and that's actually like cheaper than groceries, weirdly sometimes, but we love restaurants. And I'm not even like a huge drinker. I have one glass of wine or something, but you know, sometimes you get these bills and you're like, how is everyone in here doing this?

4:29Because they're 25 years old. I could be their mom. So I know why we're here, but like the restaurants are packed. You can't get reservations. You have to like blow somebody to get into these Instagram tables. And I just don't understand the economics, like how all these people, are they all trust on people? Like I don't, I'm just confused. But anyway, I love going out to eat.

4:49Haley: I'm also so bad at restriction at restaurants where it's like, if I see three things on the appetizer, we get it. So I'm a nightmare to eat out with. And then it's like, I want to split the check. Cause I feel like if you can't, like if we're not going to split it, then why are we having dinner? Unless someone's really not drinking and not eating. If I'm with a pregnant person. I know, but you're still young. I feel like at my age - You don't split it? We always say, you go Dutch, you ain't much. We'll pick up the check and they'll get it next time. I just want to take care of it and we leave.

5:21I like to slip my credit card and not have a thing. When I'm going to pee three quarters through the meal, I'll slip my credit card so we can just, when we're done, we get up and evaporate.

5:30Haley: I love - And there's no weirdness. And then the next time they just do it. Okay. Love that. And then have you ever had the point where like you're paying for them, but then they're not paying back for you and you felt like it was uneven? Sometimes, but they're artists or they're people that I don't think can afford it. And I don't even think about it. I don't want them to even worry or do the whole like reach for the wallet weirdness. I just want to take care of it. I love that. I have friends like that who are comedians and it's like, I just always pay for them. That's right. Yeah. You know what?

5:58they deserve to go out and enjoy things too. And I get so much joy from our friendship. And I entertain a lot at home for that reason, because I don't want people to feel weird about contributing or something. And I don't hire fancy caterers. I just order in from Tony's DiNapoli, but I'm really into my tabletop and I get all my flowers from the bodega and I just make it pretty. And it feels like an experience and no one owes me. I think it's sort of a 70s thing of like you have to reciprocate. Like I don't care. I just want to live my life and enjoy my friends until I'm dead. Yeah. Be around who you want to be around.

6:33Haley: Yeah. And don't let like who's making more. I don't keep score on anything. Yeah. And that also allows you to have inter-financial friendships. Totally. Which actually people don't have. Right. But I do. Yeah. So we always start with a few rapid fire questions. Yes ma 'am. Okay. So what are your best and worst purchases of the week and how much did each cost? This is so cunty but my worst purchase was around the corner. I just had chili chicken. I mean, chicken chili. It was bad. I don't want to say because I don't want to be mean, but I didn't like it. So I threw it out. That was a total waste.

7:08I think it was$8. I feel more guilty about wasting the food than the money. Yeah. It's a weird thing. What was the other component of the question? And then what's your best purchase of the week? Oh, I got this brown. Brown is the new gray. Yeah, it is. I got a brown cashmere dress just because I get really cold. And I usually just wear black. But I'm going as Conor Story's mole for Halloween. Oh, my God. You could do.

7:35Haley: You already have the costume. Wow. Conor Story's mole. That's inspired. Yeah. I like details. Yeah. It's important to remember that heated rivalry was this year. Oh, it fully was this year. Yeah. And I'm obsessed with it. And my daughter, Ivy, and I benched it until five in the morning. How much was the dress? I feel like it was like cheap,$2.80, something like that. I mean, cheap for cashmere. Yeah, cheap for cashmere. It was one of those like Bloomy's brands. Yeah, of course. You know, 40 carats. Yeah, I'm a 40 carats addict. And when I was pregnant with each of the three kids, I thought they were just going to be like a yogurt sculpture in a baby suit.

8:12Haley: So for those who don't know, at the Bloomingdale's in New York City, and this is very - The one on 59th Street, not Soho. Yeah. On the seventh floor. On the seventh floor. Like you're listening to two born and bred New Yorkers. Yes. 40 Carats is basically the cafeteria for those on the Upper East Side. It's within Bloomingdale's. You have to walk through the bedding department. Yeah. Wedding registry. Uh-huh. Go up a little flight of stairs. Yes. And then you will wait in line for 47 minutes if you go at prime time, which I do not. Yeah, you can't. You got to be smart about it. The best yogurt in New York.

8:43Fuck all these Instagram yogurteries and memes and all this shit. It's all crap compared to 40 carats. Oh, and then my next rapid fire is how did you make your first dollar? Oh, I had a lemonade stand except it was apple juice because I don't like lemonade. I sold apple juice at seven years old on Park Avenue and we didn't have a parent with us. My friend Dana Wallach and I just like made a little stand and we made a jingle. want to come buy some apple juice, apple juice. We like did a whole thing and everyone bought it. Oh, and there was a whole thing in the eighties and seventies about like caffeine is bad.

9:19And we would go crisp and clean and no caffeine. And we did like a little dance, like the Rockettes. And people would be like, keep the change kid. And we made$24 and we like went and spent it at Penny Whistle, which was a toy store on Madison Avenue. Yeah. That is habit. So I wasn't a good

9:38Haley: book. Yeah, you should have read my book earlier, but you know what? You weren't born yet. So we both grew up on Upper East Side and you had a dad who was like a titan of industry. He was the president of Chanel. So I figured that we should start there because it's like obviously the question on everyone's lips is, did you get free Chanel? He joined Chanel when I was nine. Before that, he was at Doyle Day and Burnback, which is like the real Mad Men type agency. And he was successful. He was vice president of the agency, but we lived in a rental apartment. We weren't really – I didn't think of myself as, like, captain of industry scion or anything.

10:13I took the public bus to spends. There were people who had limousines. Like, I was – I would say I had a very grounded, down-to-earth childhood. If we rented it Blockbuster Video, they made us go in the rain to return it so we didn't get charged the late fee. You know, we weren't, like, spoiled cunts at all. Yeah. When my dad joined Chanel, I would say I definitely was thrown into this new world. We were going on his business trips and going to fashion shows and all that. I did not get free Chanel. My mother did. But they would never give any to me because they said, like, you're a kid. And as the years went by and people turned 16 for sweet 16 gifts and got Chanel bags, my parents said, that's pathetic.

10:53You are not getting one until you're at least in your 20s. And these kids are going to have nothing to look forward to.

11:00Haley: Yeah. Growing up on the Brie side, like there is so much early wealth with the kids where it's like - Not my kids. That's good. But it's like, don't you see that with other kids there where it's like, like a little Birkin or I don't even know what - Oh my God. They're like sixth grade, like the bat mitzvah gifts now are like Van Cleef, those Van Cleef quaterfoil things. And, you know, I remember saying to my kids, I mean, I always say Ivy had said, why are you the only mom at school without red bottoms on your shoes? what she was like two and I couldn't believe she noticed that I was sort of like proud of her powers of observation but I was also horrified that we were raising them in this milieu that had so much conspicuous consumption you know I wasn't out to be their best friend I was very strict about like that's just not where I'm gonna spend my money and I'm not doing what the other moms do I don't care what anyone's doing that was sort of my thing do I seem like I care what everyone else is doing and they just stopped but in the beginning there was a lot of like, why don't we go to the Hamptons?

12:01Why don't we, you know, so-and-so has a private jet. I was like, great, good for them.

12:06Haley: Well, what's so interesting about your career is that you've basically become this like cultural anthropologist or like undercover detective on the Upper East Side where you are so embedded in the world. You were born and bred there and live there now, but you've also built this career satirizing it. So besides the, you know, private play-ins and the Van Cleef bat mitzvah gifts, what are some of the craziest things that you've witnessed in your time? So many. I mean, I've heard crazy stories of people like having a broken Fendi shoe, an alligator shoe, and sending the private jet to Europe with just the shoe to get fixed.

12:48Oh my gosh. I mean, like just obnoxious expenditures that are horrifying. I feel like a lot of entertaining has gone really over the top. I understand if you're like a self-made billionaire or whatever, and you want to throw a party, I don't judge that. By the way, happy to go to it. It's just not, I don't know, a lot of the things, I guess this is because of social media, but whether it's weddings, like I have friends who are event planners and they're like, everything's for the gram now. And so to me, that a little bit takes the soul out of like the point of a party. Um, but yeah, I've seen Birkin collections that are a hundred Birkins.

13:26I mean, I, I'm not a Birkin girl. I'd rather carry all my shit in my pockets. Um, but I just feel like things feel a little over the top. And when, I mean, I'm older than you, but when I was growing up, it wasn't cool to be rich. Like it was the, the rich girls had their limos, dropped them off before they got to school, like three blocks away. It was just that embarrassment of riches. And now I feel like everything is all about flaunting and posting the oval telltale private jets. And that's just not, I don't know, it's not my values.

13:56Haley: And it's also interesting you talk about how things have changed. Totally. Those wealth and spending trends, like what are other ones that you can point to over the years that you've seen really develop? I mean, just like, you know, birthday parties across the world. I'm trying to think of just like those, again, it feels like that Instagrammy thing of like fireworks at your birthday. But it's also hard for I think like growing up on the breeze side, at least for me, I feel like money, it's like in Sex and the City, New York's the fourth character, the fifth character. Like I feel like money was the fifth character a little bit where you sort of, even if it's, you know, people have their limos, drop them off around the block, you still sort of knew what was moving and shaking.

14:38Haley: And it was clear that you're in this town where money talks loud. Definitely. And that really does affect how you sort of perceive things. And now it's interesting because there's such a like Sephora-ification of the young girls. Such a good word. You know what I mean? Yeah, they all really were so into it. You know, back to your money story. So were there moments where you really were worrying about money and what was sort of your progression? Because, I mean, you got married young. Did that sort of give you some stability? Yes. Yeah. So from 20, I graduated college at 20. Okay, smart. I moved to New York and moved in with my parents.

15:13Then I'd moved in with a boyfriend, moved back in with my parents. And I finally got my own apartment at 24. And then Harry moved in at 26 with me. But I would say those four years I was making – so my first job at Interview Magazine, I made$18 ,000 my first year. So I couldn't afford my own apartment. That's why I lived with my mom and dad. Then it sort of like went up through the years into like the 30s. And then I went to MTV and was making more money. And the internet was starting. Sounds so old. But it was like the dawn of the internet. And I was copywriting for Ralph Lauren and I got a lot more jobs as a freelancer.

15:51I was writing for magazines and I just juggled kind of all of that. But it really wasn't until I guess my 30s that I felt a little better. But then you have all the tuitions. You have like then when you have kids. So yes, I had the stability of the two income household for a while. And I didn't feel pressure when we had one kid. But three years later, we shout out the other two, like right back to back Irish twins. That'll change everything. Then it became, because I didn't have a nanny or a housekeeper or a baby nurse for the first. Then I needed help. Yeah. So I just felt like every dollar I made went flying out.

16:28I guess it's just like so much easier now that the kids are old. I feel like now. I guess I only feel like fully settled recently.

16:35Haley: In your financial life. Yes, because I feel like Harry. Because you can actually hold on to money for yourself versus spending it towards the family. That's it.

16:45Haley: This episode is brought to you by Google Chrome. You think you know a browser, but Gemini and Chrome, that's new. It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50-page restoration block, or finally break down that long article you've had open for weeks. Gemini and Chrome is here for it. Ready to make anything online make sense? There's no place like Chrome. Check responses set up required, compatibility and availability varies 18+. This episode is brought to you by Indeed. You're ready to level up your business, but the pressure to find the right person to make that happen is intense.

17:19Haley: Indeed Sponsored Jobs can help carry the load. It boosts your job post to help it reach quality talent fast. Cut through the chaos with Indeed Sponsored Jobs. Get a$75 sponsored job credit at indeed.com slash podcast. Terms and conditions apply. Hiring now? Then this is a job for Indeed Sponsored Jobs. As listeners know, I grew up with no financial literacy. My dad was in finance, but there was truly no education around money. And in my 20s, I really felt that gap and wanted to change it. And that is how Mrs. Dow Jones came to be. This is why I love the personal finance app Monarch. My financial picture is now the clearest it has ever been thanks to Monarch's tracking and tools.

18:02Haley: And it just takes the mental load of tracking finances off your plate while making sure you stay on track. Monarch is like having a financial planner in your pocket. It helps you set goals, map out big purchases, and provides easy-to-read diagrams to help you visualize where your money goes each month. I love using Monarch's AI assistant to ask questions about my finances or the AI weekly recap to get the TLDR on my spending. Write your own money story with Monarch. Use code financialt at monarch.com to get your first year of Monarch Core half off at just$50. That's 50 % off your first year at Monarch.com with code financial T.

18:41Haley: But what I also think is interesting is like you, you met her at 25, but you got married at 27. But before that, you were engaged twice. Yes. And talk about sort of those gut feelings around those relationships and how you sort of knew that they were wrong. Well, my parents, my dad died almost two years ago and they were married for, thank you. It's so hard. I miss him so much. They were married for 54 years. So I had a lot of kind of pressure. I really wanted to get it right. And I did kind of grow up in this bubble where my parents had really traditional roles in the marriage. My dad was the breadwinner.

19:15My mom was very domestic, incredible chef and did all that homemaker stuff. And that was not going to be me. And so I needed, I wanted like the equal partnership, but also wanted to stay married for 54 years. So it was, I don't know. I just was like a cold feet person. And I wasn't sure until I met Harry.

19:36Haley: Yeah. But maybe you also felt a little bit like you had to belong to them a bit more versus like having this freedom with Harry. I needed freedom. And Harry gives me that because like you, he has a life. He's busy. He has 650 employees. He's flying around the world doing shit. Now I can go because I'm an empty nester. But for years, I'd be like, okay, I'm going to hold down the fort. You go. But I didn't really, I didn't sell my TV show until I was 39. So I was really like home for 11 years with them. But what's interesting though is Harry is a, you know, titan of industry, has this big job. He is now.

20:12Haley: He wasn't in the beginning. He's an entrepreneur. So when I met him, he had 12 employees. At one point it went down to four and now he's almost 700. Okay. Wow. Okay. Because I was going to say, how is that possible that you have three kids in New York and you're stressed about money, but you have a big income coming in? It's expensive. Yeah. How much do you think it costs per year to raise all those kids? Well, the schools are like$60 ,000 or something, but then you're also expected to donate. To get them into the school. No, no. Just like once you're a parent. Yeah. Just to – look, like some people can't afford the tuition and you want them to have scholarships and you need to like pay the gap.

20:50How much would you donate? Well, the gap, it depends each school, but they sort of do the economics and say like there is a deficit per kid, you know, that's like$12 ,000. So we would try to cover the gap.

21:02Haley: And like roughly how much do you think it costs per year to have like with the gap, with the tuition, with the nannies and the after school activities and all of this? Not you. I'm bad at math. I don't know, but it was a lot because the nannies, like I had one nanny and I had a housekeeper when I had my third. I needed full-time help. I have no kids. It was just those years were so financially draining. And we travel a lot. I mean, a lot of it was our choice and not necessity, but I felt always stressed about money. It's weird. Even though you can live in New York and be successful, you can also feel poor.

21:42Haley: No, it's the craziest city in the world. I think it could make anyone feel broke. Okay, but New York, we need your black book just really quickly. This will be another rapid fire. Like I feel like you definitely have the best recommendations. I do. Can you give us the best? I'm going to give you, I'm going to say something and then you say the go-to place for that thing. Okay, if I can. Okay. Best facial? Georgia Louise. Best blowout? Julian Farrell. Best workout class? I don't work out class. Or like trainer? I don't train. Okay, best exercise? My mom's basement. Okay, love. Best place to have lunch with a girlfriend?

22:21Haley: Maxime's. Best place to have dinner with your friends? Ops Pizza. Best place to shop? Dear Rivington. Best place for Botox? Dr. Amy Wexler. Okay, Slay. And did you have anything that you're gatekeeping that you need to tell us? Oh, and the cast. I would do the cast because I buy so much there. Okay, love that. So, you know, you mentioned just now that you sold your first TV show at 39, which I think is really inspiring for people who are listening. Because, you know, you'd brand a writer for so long. Then you had all these kids. But you kept going. And your career broke, like, later than I think people would.

22:59Haley: Much. Yeah, much later, which is amazing. Like, why is there a time limit on things? And so what. I would actually argue also that it's healthier psychologically because you don't give a shit at 39. You're already fully formed. to you know I was married I had my kids I had my life I had my friends if you're on a red carpet getting like analyzed to death and cut into pieces and you're 23 years old or whatever these young actresses are I just think that'll be really hard that you could like handle it at your age yeah whereas like I didn't care so the the show that you sold how much did you sell it for well I was the writer and actress in it so I was a creator so it's not like you sell it the way you sell a movie and get one big paycheck.

23:44It's like, you'll get like 120 ,000 per, like for writing the episodes. Then you get, well, I got paid so much less because I hadn't acted. So I had no quotes. So I think I got like 15 ,000 an episode and then every, like the stars all got like 25 ,000 because they just had more experience. So it was, you, they, you work your way up to like quotes, you know what I mean? And then how much did they pay you for the IP? I don't know I feel like my agents Jill but we're learning today on the financial team It's really bad Girl you need to know your numbers When I met you I do not know my numbers And I have like a great lawyer and a great team So you trust blindly I trust blindly CAA Oh my gosh They do all my stuff I'm worried They're not like stealing my stuff Like Billy Joel's brother-in-law or something Yeah, but it even happened to Rihanna.

24:40Well, I am lucky because Harry goes over contracts and stuff and speaks legalese and does all that. But no one's hosed me.

24:47Haley: We hope not. I promise. But we're sad that you have no numbers, but it's because you don't know the numbers. No, I have no sense of – I can barely balance the checkbook. Like, I'm very disorganized. Okay, but let's now dive into the mom cult of the Upper East Side because this is a real thing. It actually scares me because I want to live up there, but I am scared to live up there because I'm scared of the moms. Don't be scared. Here's the weird thing as a native that I can explain to you is like, first of all, I think native New Yorkers have a special aura and a superpower where we have thicker crocodile skin and shit won't really get to us.

25:26It just on one level seems like a scene, but you have to stop and say, it's New York. There's a million scenes. And I just am focused on my little Kargman 5. if I don't give a shit about what everyone else is doing. However, because you want to be a present mom in the school, and especially if you have daughters, like my son didn't give a shit if I was friends with the moms, but my daughters would say, are you going to Susie's mommy's birthday party? And so these moms would have a sit down lunch for 14 people, like all the time. So-and-so's birthday lunch, paperless posts flying all over the fucking place, like meet at this plate, meet at Lagaloo for a table for 16 and they're having like a rosé lunch, which I can't do because I'm working and I can't be shit-faced writing my article or whatever.

26:12And then you're like all splitting it and Venmo-ing everybody$200, but you're funding their rosé. And then there's also the group gift component where they're like Venmo me$250 and then they present her with like a fucking Chanel bag at the table. And it just got so crazy, honestly, Haley, that I was like, I can't do these lunches anymore because I don't want to do them. It's just, it's a time suck. I don't really do lunch. Oh, I don't do lunch at all. I just like eat on my keyboard. Yeah, no me too. And so I didn't, it felt like something that I should do that I didn't want to do. And I just stopped, but I did it for many years.

26:48And that's a huge money flying out of your wallet thing. Cause you have the, you know,$150 prefix plus tax plus everything. It winds up being like $200. And then the group gift, you're like giving one 16th of an Hermes tote or whatever the fuck. And I just, I'm not even having quality time because it's so many women. I'd rather be, I'm always better one-on-one. I don't like group meals. And they also take like three hours. Too long. Too long.

27:16Haley: Yeah. That's so interesting. I also feel like it's, you're almost like paying a subscription cost to this group that you don't even want to be part of. And, you know, you were working while you were this mom, you know, on Upper East Side. I was and I wasn't. I didn't have a full-time job. So, like, there were the moms who were brain surgeons or Wall Street analysts or whatever it was. And I feel like I always somehow was cast as a double agent. I never went to anybody, but they would come to me and say, oh, thank God we're working moms. These stay-at-home moms are so pathetic. All they do is lunch and gossip and spend money.

27:49It's so depressing. And I was like, just listening to this, because I think a lot of the working moms did have a little guilt. And so they tried to make the other side look bad. Then those people will be like, oh, there's Susie Wall Street running off, missing everything. How sad to work and miss these precious years. Yeah. It's just so sad. Why even have kids? And I didn't really chime in to either side. I was just listening because that's what I do. But I felt like I see what both sides are saying. And I was kind of just in the middle. But I was always around. So I felt more like a stay-at-home mom.

28:24Haley: Yeah. Because you had like freedom because you were writing. Well, writing. So I would write when they're napping or when they're in school or at night when they're in bed with a glass of wine or whatever. But I primarily felt like a stay-at-home mom. And I had some of the trapped feelings of that, too, where Harry got to go to the office and I was jealous, sort of, because I felt like he had a whole adult day. And he would come home and be like, how was your day? You went to that birthday party. Was it fun? And I would say, fun? It was a two-year-old's birthday party. I had three kids. I have cake smeared all over me.

28:54Like, I'm exhausted. I just bathe them. Yeah. And I was, like, jealous of him. I remember one time I probably was on the godfather day of my period and I broke down sobbing and was like, I have dreams too. And I went to good schools too. I'm just like here, you know? And he really supported me when at 39, it was kind of felt like, okay, it's my turn.

29:16Haley: It's your turn. Yeah. How old were your kids at that point? They were like 11, eight and five. It was when my son went to kindergarten. No, He was six and a half. When he went to kindergarten, I started pitching the show, and I think it aired when he was in first grade, I think. That's the light at the end of the tunnel for any moms listening. Sixth grade? No, just when your baby's in first grade. Okay, yeah. Something to look forward to. Yeah. I love that. This episode is brought to you by Google Chrome. You think you know a browser, but Gemini and Chrome? That's new. It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50-page restoration block, or finally break down that long article you've had open for weeks.

29:59Haley: Gemini and Chrome is here for it. Ready to make anything online make sense? There's no place like Chrome. Check responses set up required compatibility and availability varies 18+. This episode is brought to you by Indeed. You're ready to level up your business, but the pressure to find the right person to make that happen is intense. Indeed-sponsored jobs can help carry the load. It boosts your job post to help it reach quality talent fast. Cut through the chaos with Indeed Sponsored Jobs. Get a$75 sponsored job credit at indeed.com slash podcast. Terms and conditions apply. Hiring now? Then this is a job for Indeed Sponsored Jobs.

30:38Haley: Okay, support for today's episode is coming from Square, the system that fixes one of the biggest headaches in running a business. Look, starting a business is exciting, but running it gets super complicated. Square can help you run your business without running yourself into the ground. And right now, listeners can get up to$200 off Square hardware when you sign up at square.com slash go slash t. That's s-q-u-a-r-e dot com slash go slash t. Visit Square to get started because the right tools make all the difference. So if you're starting a business or running one that deserves better tools, Square helps you sell, manage, and grow without slowing down.

31:22Haley: Right now, you can get up to$200 off Square hardware at square.com slash go slash t. That's s-q-u-a-r-e dot com slash g-o slash t. Run your business smarter with Square. Get started today. What would you tell moms who are looking to maintain their careers or maybe start a new career while raising children. I think you have to just convince yourself that it's never too late. And also if you're a stay-at-home mom and you're playing on the carpet and you're exhausted and you, you know, I had moments where I was like, I am so brain dead. I'm not saying all women feel this way, but I felt like I'm so tired and brain dead.

32:03Maybe my best creative years were behind me because I can't even function. All I wanted to do was go to sleep. Like there were days I woke up that I thought I would look at my bed like, see you at night, I guess. I was so bone weary that I couldn't even fathom a moment of feeling fast and quick and badass again. But it's not true. It's not true. Once they are launched and you put yourself in a milieu that is challenging and exciting or you're starting something, you get it back.

32:33Haley: Yeah. Stella gets her group back. Something that I do think about, though, that you've done so well is you're someone who I look and is like very glamorous and beautiful and like... So funny. I feel so not glamorous. Oh, really? I'm like Jill Kargman. I feel like you're like a name brand of like, okay, like if there's a woman who like has like wit and looks and fashion and like... Oh, that's so nice. You're like a New York institution. I feel like I'm a slob sometimes. I think it's because I don't wear pants. So everyone thinks I'm dressed up all the time, but I'm really not. But I also want to talk to you though about like beauty and cosmetic work because you look amazing and there's obviously a price tag to that.

33:06Haley: Yes. And so what would you say? I mean, not that you know any numbers, but like how much do you think that you spend on beauty per year? And what's worth it? The facials are so expensive, but so worth it. Yeah. There's like a menu. Yeah. So you can do like add-ons of all kinds of stuff. I also get Botox like pretty regularly because I have a fabulous – I would say four times a year. Yeah. I have a fast metabolism, so it really – no, it's good for maybe food, but it's not good for Botox. It makes it go away like really fast. So the money kind of will fly out the window that way. What else? Well, I do like lip tattoos.

33:46Oh, really? Well, now I'm wearing lipstick over it because you look so pretty, so I just like shove some on in the shitter. But I have tattooed eyeliner. Who did that? I did it at JJ Eyelashes. Did it kill? Kill. I took a pain pill. And then now I do this procedure called Softwave. Wait,

34:06Haley: so all this down here is tattooed? So you always tattooed. I wake up. I wake up like this. Whoa. And then I do this new procedure. I have my little scarf. Yeah, people love the Softwave. I love it. How much is it? It's$4 ,600. Per sesh. Per sesh. They're really taking us to the cleaner. And you have to do like six sessions. You're supposed to do three. Three, but like six. But I'm going. I'm overdue. But I just feel like your neck ages faster. I mean, Georgia and I are good friends, and she tells me the truth. And she'll say to you, like, she said, your neck is seven years older than your face.

34:40Like, we need to, like, step this up. And I'm so glad. Like, I have complete trust with her. Yeah. And I'm so glad because it's better.

34:47Haley: So you're doing the soft wave? Yeah. My neck is still older than my face, but, like, I don't really care. It's like norephron. I feel bad on my neck. I'll probably do like a neck lift one day. Like have you gone under the knife? Yeah. I did an eye job and I had a double mastectomy and then I redid those implants because they were recalled for causing cancer. I don't fucking know. That's been – my boobs have been like a whole odyssey. Yeah. Because I have a bad Jewish gene. So, yeah, I've had actually three surgeries on my boobs. And how much? I mean they probably – Those were a fortune. How much was that?

35:21You have to ask Harry because he handled all the insurance.

35:24Haley: She comes on financial team, you guys. I'm trying. I'm so bad. I'm trying to get the numbers. Gary explained to me that the insurance, because of course I picked this expensive Park Avenue cosmetic surgeon to do it. The insurance companies are pure evil and they do this fair and customary reimbursement. But they're reimbursing you for a West Virginia person in a strip mall, not a Park Avenue clinician. So whatever we got back was a fraction of what we paid. It sucks. Yeah, you got the first class seat, but they were paying for economy. Yep. You had to pay a little different. Uh-huh. So we don't really have an idea of the numbers of what it takes to be Jill Kargman, but we know that she looks good and she'd be swiping that card at George and Louise.

36:06Oh, let me tell you a really big splurge that's worth it. Harry goes on October 1st. I mean, I'm sorry, August 1st, we call it Og-tober. That's when Home Depot releases their skeletons and all their Halloween decorations, and we broke the internet. Like there was a shortage nationwide of the 12-foot skeletons and it's because Harry Korgman bought them for me. And our entire house, we staged, we like hired this team to make them all look like they were breaking into our house. So we had skeletons like smashing our window and climbing up and then one hanging from a noose and one on the chimney. And we became like TikTok famous.

36:40Haley: Oh, you had one of those people who like comes and does like the pumpkin setup, but then also can do the like crazy. We do the pumpkins. Like we do all that, but they do all the shit that involves like scaling the house. Do you have a townhouse? Yeah. Oh, because this is a whole, this is interesting. Yeah. Because there's a whole thing to this on the breeze side. I know. There's like a responsibility. It's almost like. It's like a community. If you're going to have a townhouse, you have to decorate that side of the townhouse. I mean, I think so. Yeah. And people come up to us and say, thank you for doing it.

37:07Because my kid, I'll use it to bribe my toddler. Like we won't go buy the fun house if you're not good. But we have animatronic like Jack and Sally from Nightmare Before Christmas. We have like scary monsters with cleavers. We have severed hands and feet like on the spikes of our gate. We go all out. It's basically like Staten Island people. How much does it cost to hire those people? A lot. Like I want to say like$2 ,000 or$3 ,000. But we have all the shit in our basement. Okay. Like we don't do a whole new scape every year. We use the same stuff, but we do it differently. But my son, who is now in college, but he used to be the one like designing it with them and saying what he wanted.

37:46Like he's the imaginative one. And when do you have to put it up? October like 9th, I think we're doing it.

37:52Haley: Oh my gosh. Okay, this is like literally a whole thing. No, it's a whole thing. And our whole block, what's so great about our block is everyone now has risen to the occasion. It used to just be us. And now one by one, we have new nice neighbors on my one side. Congrats. That's hard to get in this town. Yeah, we don't have it on the other side. But they just like have fun with it too. And they've become our friends. and then across the street. And we all just like love it. And now people, there are these like maps that will say where to go. And it's always - Oh my gosh. Our street, it's so charming and cute.

38:24It makes it feel like a little suburb.

38:26Haley: That's so funny. Yeah, I went viral on TikTok once doing a tour of the Upper East Side. Oh, no way. Because I was like, there's rich and then there's decorating your townhouse for Halloween rich, getting someone to decorate your townhouse for Halloween rich. Those level. Yeah, no, you do. You have someone outside. No, no, I know. But those people - Oh, I know. Like 25 ,000. Yeah. And they switch up all the decorations every year. Like, so they'll design a whole skate and then they bring in all the new shit and then throw it away. Whereas we have our same guys. We just maneuver it differently. I love that.

38:58Haley: Do you, when it comes to the Upper East Side, what do you think is normalized when it comes to taking care of like beauty and cosmetic surgery? Like people. I just heard the, someone just told me getting a facelift is like getting a pedicure now. Stop. which I thought was so funny. I was like, not really. But anyway, someone just said that. Yeah. I feel like a lot of people are talking about plastic surgery and injectables as maintenance rather than like something you decide to do. It's just not, doesn't seem like as big a deal. I've picked up so many friends from procedures that I don't really think of it as a big deal and they look totally normal now.

39:33I think in the olden days, people looked really pulled and scary. Like I would do it. I'm definitely like open to it, I would say, but more in like little things. Like my, my eyes, I recovered so fast.

39:46Haley: Do you think it's awkward when you are earning money though, but you're like an Upper East Side mom to ask, I guess, like your partner, your husband for the money to pay for the cosmetic surgery? Like I always, that's, I love having my own money. I'm not married, but like I always have my own money just because I don't like asking anyone for anything. So it's like if I was like getting, and I will go under the knife, but it's like, I don't want to have to ask anyone. I don't know the answer to that. I feel like every marriage is different, but some people might say, look, I had four pregnancies and I'm exhausted and I just want this refresh.

40:20And it will, you look, and you could say to your husband, like, you look so young and fabulous. And some of us have to work at it and women don't necessarily age as well and it would just make me feel refreshed and quote unquote sweat equity.

40:34Haley: That's so good. Okay. I don't know. I don't know how it works. I'm just like saying. So like with your friends though, because it sounds like you don't really know about numbers or like talk about numbers. I never. So talk about money with my friends. It's actually fascinating. I'm getting that vibe from you. Never. Like my best friend, we'll say like, what is that? They live in a triplex apartment on Fifth Avenue. What does something like that cost? And we might Google it or something because we're just curious. But that's really my only friend I talk about money with. And like with everyone else, it's just sort of like unspoken.

41:08Yeah. I feel like I was raised, we just didn't talk about it. Maybe that was like a 70s thing.

41:13Haley: No, that was, I mean, that's how I was raised too. I think. But I have like a problem because I, it was so ingrained with me that when I was a freelancer and I would file an invoice for$3 ,600 and I didn't hear back for a month, I felt like dirty and filthy writing them again, asking just for what was due. And it just made me feel like I was shaking a cup on the corner and I was some kind of like prostitute. I hated asking for what was due. And it's a problem because Harry would have no problem being like, hi, this invoice is overdue and you owe us this. With your daughters, how do you teach them how to not have that feeling?

41:49Haley: To do the opposite of me. I said, as soon as you file the story, I have a daughter who's a writer, As soon as you file the story, you file the invoice. This is it. Here's my thing. You need to follow up just like a guy would. Interesting. Yeah, that's such a normal thing, though, for women. We always just feel sort of grateful to have even been invited or to have been allowed to write the article. Right. You know, it's like a man could never have your voice or, you know what I mean? Like it's a perspective that's so uniquely you and female and all these things. And so we end up just, yeah, sort of apologizing for wanting more, even asking for what's ours.

42:23Haley: That's it. And I always feel gross about it to this day. Yeah, there's nothing to feel gross about though. Do you think that it was like how you grew up? Like in your family, it was not ever talked about. I think it was the 70s in general. I don't know. Like New York was bankrupt. People - Women could barely have any financial independence. 1974, we were able to get our first credit. That's the year I was born. Yeah, that's the year of born. I was born when women could get credit cards. Yeah. But our car was smashed all the time. Our windows for the radio. So, you know, like it was not a great time in New York.

42:54So I think people really kept it low profile or anything. But I just remember saying, we don't talk about money.

43:03Haley: So even now, like when you, like you're not fighting for your financial independence. You're really just working for your creative freedom and like to like have, to express yourself. I mean, in my marriage, we're very much like a team now. It's been so long. I've been with him more than I've been without him. Yeah. So it's more just like a pot. But yes, creatively, I will turn down stuff all the time. So it's like his money is your money and then your money is your money. Correct. Yeah. Got it. Okay. So I know that Drew Barrymore is your former sister-in-law. Yes. But also like you collaborate with her so far and you're too.

43:39Yeah, I'm so lucky. Both my brother's wives are like my favorite people.

43:43Haley: I love your brother's current wife, by the way. She's the greatest. She's really the cutest girl. I love her so well. We're friends on Instagram. I love her. Um, so, but what is it like being family members with Drew Barrymore? It's exactly what you would think. She's like really one of the only celebrities I met where there's no gap between what people see and what is kind of, she's just like exactly that Sprite person that you would think. I love it. She's really chill. She's not, you know, fancy. She just, she just is very herself. Do you have to see her separate from your, like if you're like are so close with her?

44:18Haley: We all had dinner with Allie and Drew last weekend for my niece's birthday. Oh, amazing. Yeah, it's great. So it's like so – It's very blended. I love that. Yeah. Do you have like a favorite Drew story? Because she's – I mean, she's also financially empowered. Very. Yeah. Favorite Drew story. Oh, my God. Okay. Well, this is – this is mean. But this one – people like stop her everywhere we go. She's so famous. And they'll start crying. Like this woman in Bloomingdale's, we went for 40 carats. Of course. We were walking on the kids' floor, and this woman started crying as if she was all four Beatles and was just like, oh, my God, I had divorced at the same time, and I also entered rehab.

45:00And it was like her entire story. And Drew's just so nice looking at her with her big eyes and gave her a hug. But this now happens every time, so I'll just now every time – we were with my niece shopping, and I'll look at Olive, and I'm like, get the hook, get the hook. because she's too nice to be like, well, it was great meeting you and walk away. So it'll, we'll just be like 12 minutes going by. So I look at Olive and we have our, our facepalm moment. And then Olive will go in and be like, mom, I have to go. Cause I don't want to be like the Sean Penn one being like, excuse her. So no pictures, but.

45:34Haley: And she doesn't want to do it too. Cause it's like too nice to say. And people are, will remember that. Like you want to have them remember the moment perfectly with you. So you need the third party to be like, you have a call right now. Yeah. Her kid is the third party. I mean, I don't want to, I've done it before when she had nobody to do it. I'll do it. But yeah. These people don't know when to walk away. She's so nice. I know. And she'll, they'll say, please, can I take a picture? And she'll be like, okay. You know, she's just down. Okay. Cutie. Okay. Also, I love that you hate Birkins. I really do.

46:06Haley: Yeah. I'm anti-Birkin as well. Can you, like, why do we hate them? So it's not like the shape or that they're boring. Yeah, they're pretty bags. I just think they're fine. But it's the process by which you have to gargle someone's balls at Hermes to get the privilege to be let in to buy a$60 ,000 thing. It's an MLM. What's that? Multi-level marketing scheme. Yes. Where it's like you have to buy the product and then sell it to people. I don't need to beg for the privilege of buying a fucking bag. Just like I don't wait in line for Goyard or anything. thing. Or frozen yogurt. It's New York. There's another bag of yogurt place around the corner.

46:45I don't beg to do any of that shit.

46:47Haley: That's native New Yorker shit. That's like the most tourist thing I've ever seen. And I'll just want to end with, is there like anything that you've always wanted to get asked besides all my questions about money that you haven't and that you've always wanted to answer? Well, one thing that I've been thinking about recently is death. And I feel like a lot of people have said to me, like, you are so morbid and why are you so obsessed with death? And you have all these skulls and you have all these things. And I really want to reiterate this study from, I think it was Stanford a bunch of years ago that actually my rabbi told us about.

47:23And she's my age. We went to college together. Which synagogue do you go to? Central synagogue. Angela Booktall. The most morbid people in the world are the happiest. and I really think it's because when you are aware of your mortality, you don't sweat the small stuff and you just filch the joy out of life every day and you're not freaking out about nonsense and what this person said in a comment or what that group of moms is doing or whatever. You just don't care. It's all about reframing it as like death is the prism through which you can enjoy your life. I love that. I know and people don't get that.

47:56Like I'm actually like the happiest person. I really am the happiest person I know. And my Instagram is very doom and gloom because I feel like you have to – that's like the glasses that you have to watch life through.

48:09Haley: That everything could end. Yeah, it does. But that also is hard financially because that causes people to be so YOLO. So you have to plan a little – plan like you are – But when you have kids, you want to save for them. Yeah, and give them that graph. You want to have a nest egg. Yeah, get them the graph. Get them the graph. Just learn what that was. There's a lot of, that'll be my next book all about how to pass money onto your heirs because it's hard. It's hard. You got to use that gift tax. Yep. Yep. Set them up. Okay. Love it. Death for breakfast. Death for breakfast. Maybe that's your next movie.

48:38Yeah. Oh, wait, do you have anything you want to plug? Well, actually my next movie is Sprinkle Glitter on My Grave. It's based on one of my books. Even better. Influenced. Well, it's out now on Apple and Amazon, but I think it's for rental, but it's going to be free on Peacock in December. It's so good. If you want to save your$3.99 like a good financial person.

48:57Haley: Jill's whole catalog of work is amazing. If you need like a really smart, interesting brain to just get inside. It's all Peacock. I'm on my mounts on Peacock. I encourage everyone to go down the Canon of because you have such a sharp perspective. It is. It's the Jill Carvin Canon. And we all need to be a part of it. Thank you. Thank you. And thank you, Sippers, for listening. Please rate, subscribe, review. We read every review. We're so grateful. It really helps the show. And see you next Thursday. And of course, stay rich.

49:50Haley: app. Get your bag! No purchase necessary. 50 U.S. and D.C. age 18+. See play at mcd.com for rules and play at mcd.com slash A-M-O-E for info on playing without purchase by mail by November 2nd. Chance card game ends November 8th. Game ends November 22nd, 2026. See rules for prize details. Monopoly is a registered trademark of Hasbro.