Go back

Under Cover Upper East Sider (w/ Jill Kargman)

47m 39s

Under Cover Upper East Sider (w/ Jill Kargman)

Jill Cargman, a New York-based cultural observer and financial advocate, shares her life story rooted in the Upper East Side, where she grew up without wealth but surrounded by conspicuous consumption. She critiques the over-the-top social rituals of elite parenting—such as lavish group lunches and extravagant group gifts—calling them draining and emotionally costly. Despite her high-profile life, Cargman emphasizes financial independence, personal values, and emotional well-being over materialism. She details her journey from early career instability to financial stability through self-awareness and tools like the Monarch app, which helps track spending and build financial clarity. Cargman also reflects on beauty and cosmetic procedures, noting their normalization and personal significance, while advocating for financial autonomy and refusing to ask for money from partners. A central theme is her philosophical embrace of mortality, which she believes leads to greater joy and clarity in daily life. She concludes by promoting financial education, mindfulness, and the idea that true wealth lies in freedom and authenticity—not in possessions or status. Her story serves as a powerful counter-narrative to consumerist culture, urging listeners to prioritize personal values, financial health, and meaningful connections over external validation.

Transcription

9753 Words, 50147 Characters

English
Hello, Dan Jones here. If you're listening to this, then I'm sorry to tell you that I'm dead. This tree seems like a very odd choice of death. I'm just being real here. Where there's a will, there's a wake, is a comedy podcast hosted by Mel Gedroich. So if you've ever wished I was dead, this is the show for you. We remember Dan as a talkative man, a man of words, and now that long last, maybe we can all get a word in edgewise. Watch and listen to my episode with Mel, wherever you get to your podcasts. Hi, it's Bloma Faith, my podcast Mad Shadow and Bad is back for season 4. I'm sitting down with some amazing people, including the Tisha right. When I'm really fearful of something, I just run towards it. Judy Love. I'm Sullivan. Out of choice. Yeah, that could get you any day. Race Campbell, here we have Anita, who's a dog psychic. How eddy. He stopped barking when I'm. She said you're too noisy. I'm plenty more, mad, sad, and bad, with me, Peloma Faith. Listen now, wherever you get your podcasts. I mean, I always say Ivy had said, "Why are you the only mom at school without red bottoms on your shoes?" What shoes? Look too. 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 site of market drama, money scandals, and of course, financial pop culture. 'Cause that's what we're all interested in, right? And today, we have my friend, Jill Cargman in the house. She is a New York Times best-selling author. She's an actress. She's a New York icon. She's a filmmaker. She's an upper-east cider. And most of all, she's here in this dude. So, Jill, welcome to the Financial Tea. Thank you, Haley. It's so exciting. And I love Brookles, and I love Dumbledore. I know you're in Dumbledore. It's crazy. The F-Train shoots me out right in my neighborhood. I love it. I know. It's so easy. Pop on that. 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? Like, obviously, Uber. Yeah, Uber's the biggest for sure. Like, if I need to lean out finances, I'm cut and Uber. Yeah, I, I mean, I feel like there's certain transportation splurges, like, maybe, airfare, etc. 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 XRM-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 went 400 and went K memories. Yeah, exactly. Yeah. The memes before I, like, worms me obsessed. So besides, like, cutting Uber, like, what else do you do as a New Yorker? Because it's expensive. It's a place to live. And you're, like, so expensive. 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 drink. 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 at their 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. I know. And I just don't understand the economics. Like, how all these people, are they all trust some of people? I don't, I'm just confused. But anyway, I love going out to eat. 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 because I feel like if you can't, like, if we're going to split it, then why are we having dinner? Like, it's too, unless someone's really not drinking and not eating. Like, if I'm with a friend and a person, I know, but you're still young. I feel like at my age, you do, you don't split it. We always say you go Dutch, you ain't much. Like, we'll pick up the check and they'll get it next time. I don't, I don't like, I just want to like take care of it and we leave. Like, I like to slip my credit card and not have a thing. Like, when I'm going to pee like three quarters through the meal, I'll slip my credit card so we can just one more down. We get up in a battery. I love it. And there's no weirdness. And then the next time they just do it. Okay, love that. And then do you ever have the point where like, you're paying for that, but then they're not paying back for you? And you thought 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, yeah, I just, I'm always paid for them. That's right. Yeah. It's, you know what? They deserve to go out and enjoy things too. And I get so much joy from our friendship. And, you know, I entertain a lot at home for that reason because I don't want people to feel weird about like contributing or something. And I don't hire fancy caters. I just like order in from Tony's to Napoli. 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 I don't, 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. And be around who you want to be around. 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. Which totally 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 should each cost? This is so kind to you. But my worst purchase was around the corner. I just had chili chicken. Ooh. And I mean, chicken chili. Where? It was bad. I don't want to say external like being mean, but I didn't like it. Okay. And then, um, so I threw it out. That was a total waste. Yeah. I think it was eight dollars. Okay. I feel more guilty about wasting the food than the money. Yeah. Like I'd rather just. Yeah. Yeah. It's a weird thing. Yeah. What was the other part of the component of the question? And the fast purchase of the week. Hmm. Oh. I got, um, this brown. The 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 Connor stories mole for Halloween. Oh, my God. You could. You already have the costume. Wow. Connor stories mole. That's a spider. Yeah. I like detail. 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? How much was the dress? Um, I feel like it was like cheap to 80s. Yeah. I mean, cheap for cashmere. Yeah. For cashmere. It was one of those like Blooming'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 and a baby suit. So for those who don't know, at the Bloomingdale's in New York City. And this is the one. I'm 15 nights straight. Not so. Yeah. This is inside the ball. Like we're with. You're listening to two board and bread. New Yorkers. Yes. 40 carats is basically the cafeteria for those on that breathe side. It's within Bloomingdale's. You have to walk through the bedding department. Yeah. Wedding registry. Go up a little flight of stairs. 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. It's the best yogurt in New York. Fuck all these Instagram yogurteries. Yeah. And Mimi's and all this shit. No. 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 by some apple juice. Apple juice. We like did a whole thing and everyone. Oh, and there was a whole thing in the 80s and 70s about like caffeine is bad. And we would go crisp and clean and no caffeine. And we did like a little dance like the rocket. 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. Yeah. So I wasn't a good saver like you. I should have read your book. Yeah, you should have read my book earlier. But you know what? You want to make more? Yeah. So we both grew up on Upper East Side and you had a dad who was like a Titan of industry. He was a 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. Um, before that, he was at Doyle Day and Burnback, which is like the real madman. Oh, wow. I type agency. And he, you know, 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 sion or anything. Um, I took the public bus to spend. There were people at limousines like I was, I would say at a very grounded down to earth childhood. If we rented a 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 cuts at all. Yeah. Um, 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 in 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 when I, as the years went by and people turned 16 for sweet 16 gifts and got Chanel bags, my parents said that's pathetic. You are not getting one until you're at least in your 20s. And these kids are going to have nothing to look forward to. Yeah. Growing up on the bridge 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 burkin or I don't even know what my god, they're like six, six great, like the bot mitzvah gifts now are like van cleaf those van cleaf watcher foil 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 going to 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 get to the Hamptons? Why don't we, you know, so and so has a private jet. I was like, great, good for them. Well, what's so interesting about your career is that you've basically become this like cultural anthropologist or like undercover detective on the brewery 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 clans and the van cleaf bot mitzvagéfs, 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. I mean, like just obnoxious expenditures that are horrifying. I feel like a lot of entertaining has gone really over the top. Yeah. I understand. If you're like a self-made billionaire, whatever you want to throw a party, I get, I don't judge that. By the way, happy to go to it. Yeah. 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. But yeah, I've seen Birkin collections that are 100 Birkins. I mean, I, I'm not a Birkin girl. I'd rather carry all my shit in my pockets. But I just feel like things feel a little over the top and one, 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 drop 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. And it's also interesting that 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, 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 preside at least for me, I feel like money. It's like in Sex in the City, New York's the fourth care, the fifth character. I feel like money was the fifth character a little bit where you sort, 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. 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, the forification of the young world, you know, they all really were in 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. I moved in with my parents. Then I had moved in with a boy, friend, 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 while my first year. So I couldn't afford my own apartment. And 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. I was writing for magazines. And I just juggled all 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 tuition. You have like them when you have kids. So yes, I had the stability of the two income households 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. I reached 20. That'll change everything. Then it became because I didn't have a nanny or a housekeeper or baby nurse for the first. Then I needed help. Yeah. So I just felt like every dollar I made went flying out. I 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 in your financial life. Yes, because I feel like you can actually hold on to money for yourself. Yes, spending it towards the family. That's it. 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. And this is why I love the personal finance app monar. My financial picture is now the clearest it has ever been thanks to monarchs tracking in tools. 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 monarchs. 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 financial t 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. But what I also think is interesting is like you, you might already 25, but you got me to 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 them 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. My mom was very domestic, incredible chef and did all that. 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. 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. Yeah. 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 like doing shit. Now I can go because I don't, I'm an empty nest. But you know, 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 till 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. He wasn't in the beginning. He's an entrepreneur. So he, when I met him, he had 12 employees at one point, it went down to four. Yeah. 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, so expensive. 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 also are expected to donate to get them into the school. No, no, just like once you're a parent, but just to look like some people can't afford the tuition and you want to have scholarships and you need to like pay the gap. How 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. And like roughly how much do you think it costs per year to like with the gap with the tuition, with the, 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 like full time help. And I was just those years were so financially draining. Yeah. And we travel a lot. And all, I mean, it was like 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. No, it's the craziest city in the world. Like 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 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. - Maximus. - 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 keeping that you need to tell her? - Oh, and the cast, I would do the cast 'cause I buy us 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 later than I think people would. - Much. - Much later, which is amazing. Like there's, does it wise our time limit on things? And so why, I would actually argue also that it's healthier psychologically because you don't give shit at 39. You're already fully formed. 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 older, whatever these young actresses are, I just think they'll be really hard. - You could like handle it at your age. - Yeah, whereas I don't care. - So 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. It'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 in episode and then every, like the stars all got like 25,000 'cause they just had more experience. So it was, 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 agent's still, while we're learning today, and the finance feels really bad. - No, but this is my point. - Okay, well 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. - Oh my gosh. - They do all my stuff. - I'm worried. We need to make sure they're not like, they're not like stealing my stuff, like Billy Joel's brother-in-law or something. - Yeah, but it even happened to Rihanna. - Well I am lucky 'cause Harry goes over contracts and stuff and speaks legalese and stuff like that, but no one's host me. - We hope not. - I promise. - But we're sad that you have no numbers, but it's because you don't go the numbers. - 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 'cause I wanna 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 is the native that I can explain to you is like, first of all, I think native New Yorkers have a special aura and a super power where we have thicker crocodile skin and shit won't really get to us. It 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, I'm focused on my little Cargmen 5, 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 Suzy's Mommy's birthday party? No, and so these moms would have a sit down lunch for 14 people, like all the time. So in so's birthday lunch, paperless posts flying all over the fucking place, like meet at this plate, meet at La Goulouse 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 ship-facing, writing my article or whatever. And then you're like all splitting in and then mowing everybody to $200, but you're funding their rosé. Yeah, and then there's also the group gift component where they're like vanmomi $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. 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 and that's a huge money flying out of your wallet thing 'cause you have the, you know, $150 pre-fix plus tax, plus everything, it winds up being like $200. Yeah. And then the group gift, you're like giving one-sixteenth of an Air Mess tote or whatever the fuck. And I just, I'm not even having quality time 'cause 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. 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 that preside. Like you had it. I wasn't, 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. It's so depressing. And I was like, just listening to this 'cause 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 Suzy 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 was, I didn't really chime in to either side. I was just listening 'cause 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. Yeah, but 'cause you had like freedom 'cause you were writing. Well, writing. So I remember when they're napping or when they're at 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 because I felt like he had a whole adult day and he would come home and be like, how was your day? He 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've kicked, smeared it all over me. Like, I'm exhausted. I just bade them. Yeah. And I was jealous of him because I felt like, 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. Oh my God. I was like, here, you know? And he really supported me when at 39. It was kind of felt like, okay, it's my turn. It's your turn? Yeah. How old were your kids at that point? They were like 11, 11, 8, and 5. 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 them 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. Observe the North American dad, 50s, great polo collection. He enters his vehicle information on Carvana and offers appears in minutes. Remarkable. He squints, reads it again, smiles and says, dang. That's a good offer. The highest form of approval, no haggling, no hassle. No one called him boss. He's still on the couch astonishing. Sell your car today on Carvana.com. Pick up these may apply. Hello, it's Elizabeth Day from How to Fail Here. My next guest is a Wall Street veteran, a former White House communications director, and co-host of the hip-hop cast, the rest is politics, US. It's the mooch, Anthony Scaramucci. Let me take you through my day on the 31st of July, okay? I am fired from the White House. I have missed the birth of my son. My wife has filed for divorce on me. I am torched and excoriated by the late night comedians. Is that real enough for you? Listen to How to Fail, whatever you get your podcasts. 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/go/t. That's squ-ar-e.com/go/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. Right now you can get up to $200 off square hardware at square.com/go/t. Run your business smarter with square. Get started today. 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. Maybe 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 was, I thought like I would look at my bed like see you at night. I guess I'm just I was so bone weary. Yeah. That I couldn't even fathom a moment of feeling fast and quick and bad-ass 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. Yeah. A salad got her group back. You know, something that I do think about though that you've done so well. It's like you're someone who I look at. It's like very glamorous and beautiful and like so funny. I feel so not glamorous. Oh really? I'm like Jill Cargman. 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 that's so nice. I feel like I'm a love 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. Yes. And so what would you say? I mean, not that you know any numbers, but like how much shooting that you spend on beauty per year and what's worth it? The facials are so expensive. At Georgia 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 for times a year. Yeah. I have a fast metabolism. So it really, no, it gets it's good for maybe food. Yeah. 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. Oh 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 who did that? I did it at J.J. eyelashes. Did it kill? Kill. I took a pain pill. And then now I do this procedure. So that's all this down here is yeah tattooed. So you always tattooed. I wake up. I wake up like this. And then I do this new procedure. I have my love the soft wave. I love it. How much is it? It's $4,600 per sash. Per sash. They'll really take us to the cleaner and you have to do like six sessions. You're supposed to do three. Three, but like six. But I I'm going, I'm overdue. But it's 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 your neck is seven years older than your face. Like 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. So so you're doing the soft wave. Yeah, my neck is still lower than my face. But like I don't really care. It's like not upfront. I feel bad about my neck. I'll probably do like a neck lift one day. Yeah. Like I 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 these were a fortune. How much was that? You have to ask Harry because he handled all the insurance numbers. She comes up. I know it's so bad. I'm trying so bad. Harry explained to me that the insurance because of course I picked like this expensive park avenue cosmetics surgeon to do it. The insurance companies are pure evil. And they do this like fair and customary reimbursement. But they're reimbursing you for like a West Virginia person in a strip mall, not a park avenue or clinicians. So whatever we got back was a fraction of what we paid, you know, yeah, you had to sucks. Yeah, you got the you got the first class seat, but they were paying for economy. Yep. You're to pay the whole difference. Uh-huh. So we don't really have an idea of the numbers of what it takes to be Joel Cargman. We know that she looks good. And she be swiping. Oh, let me tell you really big splurge. That's okay. Harry goes on October first. Wait, I mean, I'm sorry. August 1st. We call it October. That's when Home Depot releases their skeletons and all their like Halloween decorations. And we like broke the internet. Like there was a shortage nationwide of the 12 foot skeletons. And it's because Harry Cargman 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 news and one on the chimney. And we became like TikTok famous. 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 that breathe side. I know. And there's like a responsibility. It's almost like it's like a community. Yeah. If you're gonna have a townhouse, you have to decorate that side. I mean, I think so. Yeah. And people come up to us and say, thank you for doing it. Because my kid, I'll use it to bribe my toddler. Like we won't go by the funhouse 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 two or three thousand. And we have all the shit in our basement. Okay. Like we don't do a whole new scape every year. Yeah. We use the same stuff, but we do it differently. Yeah. My son who is now in college, but he used to be the one like designing it with them and saying what he wanted. Like he was he's the imaginative one. And when do you have to put it up? October like ninth. I think we're doing it. Oh my gosh. Okay. This is like a 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 and he used to just be us. And now one by one, we have new nice neighbors on my one side. Let's try to get in this town. Yeah. We don't have it on the other side. Yeah. 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 they're these like maps that will say where to go. And it's always. Oh my gosh. It's so charming and cute. It makes it feel like a little suburb. That's so funny. Yeah. There I went. I went viral on TikTok once, doing a tour of the upper east side. Oh, no way. Yeah. Because I was like, there's rich. And then there's decorating your townhouse for Halloween rich, getting somebody to decorate your townhouse for Halloween rich. That was level. Yeah. No, you do 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 scheme. 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. 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 I just heard the. Someone just told me getting a facelift is like getting a pedicure now. 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 thing. And they look totally normal now. I 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 or I recovered so fast. 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. Yeah. I'm not married. But like I always have my own money just because I don't like asking anyone for anything. So 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 and 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 put sweat equity. That's so good. Okay. I don't know. I don't know how it works. I'm just like. Yeah. So like with your friends though, because it sounds like you don't really know about numbers or like talk about never. I never talk about money with my friends. It's actually fascinating. I'm getting my vibe from you. Never. Like my best friend, we'll say like what is that those they live in a triplex apartment? I'm fit down. What is that? What is 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. Yeah. I feel like I was raised. We just didn't talk about it. Maybe that was like a 70s thing. No, that was I mean, that's how I was raised too. I think my but I have like a problem because I it was so ingrained with me that when I was a freelancer and I would file a 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 to do the opposite of me? I said as soon as you follow the story might I have a daughter as a writer. As soon as you follow the story, you 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. 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. That's it. And I always feel gross about it. Yeah, there's nothing to feel gross about, though. Do you think that it was like how you grew up? Like 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. Yeah, women could barely have any financial independence 1974. We were able to get our first try. I was born. Yeah, I was born when women could get credit cards. Yeah, but our heart was smashed all the time. Our windows for the radio. You know, like it was not a great time in New York. So I think people really kept it low profile of anything. But I just I just remember saying we don't talk about money. 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 yes to express yourself. I mean, we're 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. I love her and you're doing it. I'm so lucky. You're both my brothers wives. They're like my favorite people. I love your mother's current wife. She's the greatest. I love her so well. We're friends on Instagram. I love her. 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 that. 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? No, we all had dinner with Ali and Drew last weekend for my niece's birthday. Oh amazing. Yeah. 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 40k. Of course. We're 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 like entered rehab and it was like her entire story. And Drew's just so nice looking at her with her big eyes and like gave her a hug. But this now happens every time. So I'll just now every time I'm 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 me and walk away. So it'll just be like 12 minutes going by. So I look at Olive and we have our our face palm moment. And then Olive will go in and be like mom I have to go because I don't want to be like the Sean Penn one being like excuse her. Yeah. Yeah. So no pictures. But she doesn't want to do it too because 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 hit is the third party. I mean I don't want to. I've done it. Yeah, you've got when she had nobody to do it. Yeah, I'll do it. But yeah, 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 Berkins. I really do. Yeah. I'm anti-Berkin as well. Can you like why do we hate them? So it's not like the shape or that they're boring. And 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, head air mess, to get the privilege to be let in to buy a $60,000 thing. It's an MLM with a multi-level marketing screen. Yes. Like where it's like you have to like buy the product and sell it to people like I need to beg for the privilege of buying a fucking back. Just like I don't wait in line for Goryard or anything or it's New York. It's New York. There's another bag of yogurt place around the corner. I don't like to do any of that. That's Native New Yorker ship. When you that's like the most tourist thing I've ever seen. And I 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 out 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. And she's my age. We went to college together. Which didn't have to go to central synagogue. 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 filter 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 like 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 you have to that's like the the glasses that you have to watch life through. That everything could end. Yeah, it does. But that also is hard financially because that causes people to be so yellow. Yeah. So you have to plan a little plan like you are when you have kids you want to save for them. Yeah. And give them that last day. Yeah. Get them the grad. Get them the drawings. There's a lot of that'll be my next book all about how to pass money on to your ears because it's hard. It's hard to use that gift tax. Yep. Yep. Set them up. Okay, love it. Death for death. Death for breakfast. Death for breakfast. Maybe that's your next movie. Yeah. Oh, wait, do you have anything you want to plug? Well, actually my next movie is sprinkle glitter on my grave. Okay, 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. You want to save your $3.99, like a good financial person. Joel'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 encourage everyone to go down the canada because you've stuck us to our perspective. It is. It's a Joel carbon canada. And we all need to be a part of that. 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.

Podcast Summary

Key Points:

  1. Jill Cargman shares her experiences growing up on the Upper East Side, emphasizing a grounded, non-wealthy childhood despite her affluent environment.
  2. She critiques the culture of conspicuous consumption, especially among upper-class moms, highlighting extravagant parties, group gift-giving, and over-the-top spending as exhausting and socially draining.
  3. Cargman reveals her personal financial journey, including early career struggles, raising three children in New York, and the emotional and financial toll of parenting while maintaining a creative career.
  4. She openly discusses costly cosmetic procedures and beauty routines, noting their normalization in society and the emotional significance behind them, while emphasizing financial independence and autonomy.
  5. A recurring theme is the contrast between New York's financial culture and personal values—where wealth is flaunted, but authenticity and emotional well-being are prioritized.
  6. Cargman reflects on the psychological benefit of confronting mortality, arguing that awareness of death brings clarity and focus on what truly matters in life.
  7. She promotes financial literacy tools like Monarch, citing them as essential for managing money without mental strain.
  8. Her story underscores the importance of financial autonomy, emotional freedom, and rejecting societal pressures to conform to wealth-driven norms.

Summary:

Jill Cargman, a New York-based cultural observer and financial advocate, shares her life story rooted in the Upper East Side, where she grew up without wealth but surrounded by conspicuous consumption. She critiques the over-the-top social rituals of elite parenting—such as lavish group lunches and extravagant group gifts—calling them draining and emotionally costly. Despite her high-profile life, Cargman emphasizes financial independence, personal values, and emotional well-being over materialism.

She details her journey from early career instability to financial stability through self-awareness and tools like the Monarch app, which helps track spending and build financial clarity. Cargman also reflects on beauty and cosmetic procedures, noting their normalization and personal significance, while advocating for financial autonomy and refusing to ask for money from partners. A central theme is her philosophical embrace of mortality, which she believes leads to greater joy and clarity in daily life.

She concludes by promoting financial education, mindfulness, and the idea that true wealth lies in freedom and authenticity—not in possessions or status. Her story serves as a powerful counter-narrative to consumerist culture, urging listeners to prioritize personal values, financial health, and meaningful connections over external validation.

FAQs

People often overspend on Uber rides, luxury restaurants with high prices and limited seating, and expensive travel. Some even spend thousands on items like Birkin bags or send private jets to fix a single broken shoe, highlighting a culture of conspicuous consumption.

Many prioritize experiences over material possessions, avoid unnecessary spending, and focus on shared costs like splitting restaurant bills. Simple habits such as cooking at home, choosing affordable dining, and cutting back on transportation help manage expenses effectively.

Yes, many upper East Side moms host lavish lunches and group events with high costs, sometimes reaching $200 per person. These events often involve group gifts like Chanel bags and can be extremely time-consuming, leading to significant financial outlays and stress for participants.

Cosmetic procedures are increasingly seen as routine maintenance, like a pedicure. The speaker notes that many people now view them as normal and necessary, rather than major life decisions, and believes they help people feel refreshed and confident without being overly dramatic.

The speaker realized the importance of financial education early in life and now uses personal finance tools like Monarch to track spending, set goals, and visualize money flow, which has helped them take control of their finances and reduce stress.

The speaker initially felt guilty or embarrassed asking for payment, comparing it to being a 'prostitute.' However, they now see it as a normal part of business, and believe women should follow up like men do—without apology or discomfort.

Chat with AI

Loading...

Pro features

Go deeper with this episode

Unlock creator-grade tools that turn any transcript into show notes and subtitle files.