Going Out With Jake Cornell: A Cheeky Cigarette (w/ Chelsea Fagan)

This week, Jake goes out with Chelsea Fagan, writer and co-founder of The Financial Diet. The two discuss children at fancy restaurants, the lost art of putting in an effort, their favorite genre of fries, and paradigm-shifting Caesar salads. Tune in for more.

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Jake Cornell: That’s a gift.

Chelsea Fagan: I’m done talking about it, but wow.

J: You can talk about it as much as you want, honestly.

C: Hi Penny.

J: Thank you so much for doing this show.

C: Oh my God, thank you for having me. I feel like now I’m not quite pivoted enough towards you.

J: Ooh. Oh no, it’s totally fine, and then you can just pull the mic like right to you and then you’re good. Thanks.

C: Oh, okay. That’s easier.

J: Oh, that’s perfect. I’m so excited to have you on. Are we recording? Okay, gorgeous. I was so excited to have you on because you are someone who I’ve gone out with a good handful of times.

C: Yes. We have a mutual friend.

J: We have a very close mutual friend.

C: Ooh, sounds like we’re in a throuple when we say that.

J: Considering you work with her, I think that’s definitely not the case.

C: No. I hope not.

J: I would hope not. Obviously, you are one of the founders and creators of The Financial Diet.

C: Correct.

J: Personal finance is a huge part of your conversation and I think that’s a huge part of the conversation of going out, and restaurants, and bars, and nightlife that gets skipped, on this show at least. We’re constantly talking about the place to go, and I don’t want to exclusively talk about that. I do want to talk about the fun stuff, and where you like to go, and how you like to go out, because you also have incredible taste and you go to France a lot, and it looks so nice.

C: Thank you. I do.

J: I also think I as someone who identifies as being bad with money, and most of that bad with money goes to nightlife and stuff, I want to pick your brain about your relationship, because I know you like going out.

C: I do.

J: You do like a dining out. I think that that’s nice because I do think, and I know you combat this a lot in The Financial Diet because I am a consumer of it, growing up I feel we were just taught like, “Oh, going out isn’t something you should do unless you’re rich.”

C: Yes.

J: It was a very black-and-white conversation. There was no nuance. What was your relationship to going out when you were young?

C: My family didn’t have really any money growing up, so I feel like I can count the number of real restaurant memories that I have before the age of 10, 12 on one hand. It was always a very big thing, and we’re talking still about chain restaurants, nothing—

J: Applebee’s $0.99.

C: Yes, Outback. Nothing super fancy. It wasn’t just a question of not necessarily having the money for it, it was also this isn’t really a place for a child, with very rare exception. If we’re going to be spending the money and taking the time to go out, it’s going to be for mom and dad to have a moment together. Even all these years later having a very different socioeconomic status, going out quite a bit myself, I still feel very not great when I am in — I’ve been to multiple Michelin-starred restaurants where there’s children on iPads at the table. Obviously, a lot of that is living in New York City, but it’s one of the things that I really struggle with not feeling judgmental and resentful towards is, children who I think are— For the record, it’s not even that I think— I feel very grateful that I did not have those things growing up because for me, still to this day, every indulgent experience is mind-boggling. It’s so wonderful. Whereas for these kids, I feel like they’re burning out all of their pleasure receptors by the age of 12.

J: Damn. That’s such a good argument that I never even thought of because I am also very anti-children in fancy restaurants.

C: What are they doing there?

J: What are they doing there?

C: They don’t even want the food. They don’t want to eat this.

J: I know. I think the same about— This one’s a little bit of a different conversation, but I have had the fortune of recently flying first class a few times, and there’s a lot of children in first class because rich families fly together and I just— Obviously, I’m not expecting you to put your kids in a different part of the plane than you, that’s crazy, but I do similarly think like, “If you fly first by the age of 5, where do you go?”

C: Down. It’s funny, one of my good friends who also works in the personal finance industry, she’s very candid about it, she grew up very, very wealthy. She lived in different countries in Asia growing up and exclusively flew business or first class with her family growing up. Since becoming an adult and supporting herself, she flies coach. She’s all about like gaming miles and stuff, so when she can, she upgrades herself, but for the most part she flies coach. Her husband grew up working middle class, so for him just flying anywhere was awesome. She was like, “It was a rough downgrade when I was a young adult and I was like, ‘This is what it’s like?'”

J: You don’t have bathroom access. There is limited bathroom access.

C: Yes, and it’s very unpleasant, especially for longer flights. I think you’re really taking something away from a child when you’re giving them such a level of luxury. She’s talked about it before herself. She was like, “I feel like I was set up to have tastes and expectations that are not realistic for me to be able to achieve on my own, and if I didn’t grow up that way, I wouldn’t have ever missed them.”

J: Damn. That’s so real. That’s also just such a really convenient way for me to have a morally sound argument against why kids shouldn’t be in restaurants-

C: Now, here’s the thing.

J: -because I also just don’t want them there.

C: You have worked a lot of service industry jobs.

J: Yes.

C: As have I. I have worked very nice restaurants where I was serving children at the tables. This was slightly pre-all the kids having iPads in their hand, but even still it was gaming systems or whatever.

J: Game Boys, yes.

C: I was just like, “I know if you can afford this child’s meal at this restaurant, you could afford a babysitter.”

J: A hundred percent..

C: Not only is this child not— They are not enjoying this menu, they’re not enjoying this restaurant experience, they have to be quiet, they have to wear clothes they don’t want to wear, it’s also detracting from your experience of this restaurant. What are we doing here?

J: A hundred percent.

C: What are we doing here?

J: A good friend of mine who I won’t name just for sake of this, I don’t want to drum up this issue for her again, but she got married last year and she tweeted, “I’m not —” She wrote a joke about it. She basically just made a joke on Twitter, but it was serious. She had a kid-free wedding. Kids were not invited to her wedding. The amount of hate she received on the internet, she had to go private on Twitter, she had to delete the tweet, people were like— It heightened to the point where someone accused her of being a child murderer. It’s like, “I don’t want to go to a wedding with kids in it personally.” If I have the vote, I’m going to say no kids.

C: Right. I think it’s also like maybe you have part with kids and part without.

J: Ceremony, I don’t give a sh*t if the kids are.

C: Yes, have them, but I also feel like there’s— I understand that it shouldn’t be exclusionary and I do understand that organizing childcare can be very difficult for people, but I also feel like we’ve really gotten away from the idea with weddings that increasingly people are getting married later. They’re paying for their own weddings. They’re having the event that they want to have. I think it there should be a right to say, “Hey, I can’t attend the wedding in that case. I might have to pass and just send a gift or what have you.” If this person is paying for their own wedding and they’re throwing on average a what, like $20,000, $30,000 party depending on what part of the country you live in, you should be able to have the party that you want to have.

J: A hundred percent, and just on the note of exclusionary, when we’re talking about the restaurants, and disagree with me if you disagree, I’m very specifically talking about expensive high-end restaurants.

C: Oh, of course. At an Outback Steakhouse, bring your kids. I know what I’m signing up for. That’s my point. If you’re in a situation where you have kids and you can’t afford a babysitter, but you can afford to go out to dinner with them for whatever, I don’t know the breakdown of that but I want you to have your night out. If you can afford to go to Per Se, you can afford the babysitter and I don’t want to see your f*cking kid there. I’m specifically referring to— My husband and I went to a restaurant similar to Per Se for an anniversary in New York City and there was a table— He’s more into that stuff than I am. I like a certain caliber of restaurant, but there are very diminishing returns for me after a certain level.

J: A tasting menu like that is tough. I don’t have much success.

C: I go and get a burger after I’m like, “This is—” I also just don’t feel that I have quite a refined enough palate to really appreciate it. My husband, much more so he loves it. That’s more for him. We’re at this table, this is something we’ve been looking forward to for six months at least, across the aisle from us is a table with a man, a businessman-looking type who probably comes here for lunch regularly, and his probably 10-year-old son who’s in a jacket because it was jacket-dining-room required, eating the tasting menu but barely, flicking through an iPad, and first of all, I’m sorry, but if this is my restaurant, you don’t get to flick through an iPad at the table.

J: I don’t want blue light. I don’t want blue light in the room.

C: When I tell you, it really to some extent ruined my meal. I’m serious.

J: No, I’m laughing because it’s like, I get it.

C: This is something that I do think that there is— This is inevitable. There is massive wealth inequality. By definition, luxury products are going to be primarily consumed by a class of people for whom this isn’t special, for whom they can afford to do it all the time.

J: God, I do so much work to not think about that because it’s so depressing.

C: It is.

J: It’s so depressing.

C: Did you read that article recently about the woman who went to Capri and hated it?

J: Yes.

C: No, it was Positano, and hated it. Although half dozen. It was so well put because it was like through social media we’re all exposed to this specific jet set vacation image of Positano that is essentially based on— It is a luxury vacation destination that for most of human history was really only accessible to an extreme elite of society. Now, everyone can go, but you can’t get the really good version. You’re not staying in the Hotel Serenos or whatever the really nice one is there, you’re staying at some moderate hotel, or you’re staying offsite, or in an Airbnb or what have you. You’re going to these restaurants that are mid- to upper tier and barely being able to afford to eat the things on the menu and getting to be in proximity to people for whom this is just another stop. It’s a very strange thing where luxury, especially in hospitality and food and beverage, is more accessible to more people than ever, tourism as well, but because it can’t scale infinitely, everyone’s just getting a kind of crappy version of it while the people for whom a two-Michelin- starred restaurant is just another business lunch, they’ve probably already moved on to another place.

J: Absolutely. That’s why I usually talk about it in terms of restaurants in New York, but I think it’s probably true of vacation destination. You and Holly and you guys travel much more than I do. Just like, I think out of priority. I’m much more of like a stay in my city and go out a lot than do big trips at this point of my life. I think what I always say about restaurants is the place that you really love to go to that is special for the reasons you have personally is always going to be more special than the place that has become Positano or whatever that’s already popular. By the time you go to the restaurant that is the hottest place in town, it’s whatever was made it special is probably been blown out the water by its need to scale out, because of its popularity. I think that’s probably true of like— I’ve never been to Carbone and I’ll never go now because I know for a fact it’s too blown out. We should probably bleep that. I made a rule that I’m not going to disparage restaurants on the podcast.

C: Barcone.

J: They’ll know what I meant, but I would venture to guess maybe when it first opened it was actually something really phenomenal. Now they have to accommodate the fact that the dining room is booked out. You like, it has to accommodate something bigger than what it was, and it can’t be that special intimate thing that it used to be. Do you know what I mean?

C: With a thousand percent I, my biggest pet peeve in this and I— can I say an actual name?

J: Absolutely.

C: Someone once said to me that what I love in this life is a continental dining experience and I truly, nothing to me is better than when there’s a lobster Newberg on the menu when there’s like a tableside something like a tableside Caesar, like a Martini that comes in a little sidecar,-

J: The theater of it.

C: -the warm nuts with your drink, all of that stuff. There are a few restaurants and bars in the city that have that vibe that I really love. Obviously, for people who like that experience specifically, hard to do better than Bemelmans.

J: I literally knew you were about to say Bemelmans.

C: When I tell you, listen, I’m not a super-casual person in general in terms of presentation, but I really do feel that there are very few places left that you can go in New York City where people are generally holding themselves to a reasonably nice standard for going out. It has been and they’ve done puff pieces on this, but these old-school places have been inundated with Gen Z TikTok types. To me, seeing someone in a place like that with hand-painted wallpaper with these exceptionally crafted drinks and beautiful piano music, to have someone next to me who’s in a baseball cap and flip flops playing on their phone, it so diminishes everything. That is worth it about that because these drinks, it’s a $25 cocktail. It’s not something you’re going to go do every day. I do think— Yes.

J: That $25 you’re paying for that room and that experience.

C: Exactly.

J: It’s not the gin in the glass. It’s not the lemon. It’s partly that, but it’s the theater— I talked about this when Ashley Gavin was on the podcast, we talked about this so much. This idea of whenever you’re stepping into like a bar or a restaurant or a vacation experience, whatever it is, it’s theatrical. There’s a tone to it, there’s an energy. I do think it is like in your best interest of enjoying the thing and also out of respect for everyone else trying to enjoy the thing, you have to step up to the plate and show up to what that is. That doesn’t mean conform, that doesn’t mean wash away any identity or diversity, you have to do this, but what is— I always say, what is your version of nice, do you know what I mean?

C: Of putting in an effort.

J: Of putting in an effort, and I think we can all agree, and we now all know how I feel about flip flops in New York and it’s bad, but like—

C: It’s bad. This is why L.A. is not my people, because every place I’ve ever been to in Los Angeles, no matter how nice it is, the men there look like they just walked in from bed. There’s just very little— I understand that for a lot of people, I think that there’s this very strange- we’re in a very strange relationship with authenticity and you don’t want to seem to be trying too hard. I think a lot of times what gets lost is this idea that ultimately society is a contract. When we’re having— Like you said, when you’re entering the theater, when you’re entering a special moment, it doesn’t make it less authentically you to rise to the occasion of that moment, because at the end of the day, it’s not like you’re in your home. You’re choosing to go to a third location where you’re spending $100 for a few hours to get a couple of drinks or what have you. That, to me, I think the idea that it’s somehow an affront to ask us all to put in a little effort and be a little special or that it diminishes our authenticity, because you said, your version of special can be very different.

J: Yes. The places we’re talking about, the ability to go there in theory is indicative of an inability to have at least some time and effort to put into it. Do you know what I mean?

C: Of course.

J: That’s like what we’re talking about and I think what you were just saying about— What did you say? We have an interesting relationship with authenticity. I think sometimes what can get written off is like, oh, well, it’s like oppressive to have a high— I don’t want to say dress code, but standard of effort put in, I guess.

C: Yes or presentation.

J: Presentation. I think it’s like, we’re not talking about men have to wear this and women have to wear this or everyone has to wear this, but it’s like, can you just do something that elevates your personal self to feel like you really are showing out? You’re there. That’s part of what you’re going to do is like show out and like dress nice and like look great and like be part of this special room.

C: I totally agree. It’s funny, I was having this conversation recently with a friend where we both changed socioeconomic status in becoming adults. Like I said, we really grew up not wealthy at all. My parents are more middle class now, but when we were growing up, we were very working class, lower middle class, everything that goes along with it. I think as all kids do to some extent, but especially if you grow up not having a lot, a very clear idea in my head of what rich people were like and what rich person life was like. It did use to be that way to an extent. There did used to be, I think much more codified social norms around-

J: Absolutely.

C: -presentation and dress codes and all of those things.

J: Like “high society.”

C: Yes, exactly. I think we’ve now— I’ve felt disillusioned in the sense that I’m not a 1 percenter, but I definitely am in a very different socioeconomic bracket than I was growing up. I’ve realized that we’re now, especially when you think about like the rise of the tech bro and the athleisure and all of these things, we’ve now come to this very strange moment where wealthy people want- and there’s actually really interesting sociological data around this, go out of their way to camouflage the fact that they’re wealthy. That not putting an effort is actually more of a class marker. To be able to move in these spaces, to be able to go to an elite restaurant, let’s say, or walk into a social club in a T-shirt, that in and of itself is more powerful.

J: Is a sign of power.

C: I think it’s a little sad because almost like I was hoping there would be like feathers and sh*t, and like top hats.

J: Do you think in the way that fashion— I wonder if it’s cyclical, like do if it and I think it almost has to be because it is ultimately like a social trend in a fashion. I do think at some point if everyone looks like, the person who is showing up in a suit is going to start to stand out. I do wonder if in 10 years, we’re back.

C: Maybe.

J: I would personally, I don’t know, I feel conflicted about it because I think I would never want it to go back to as traditional as it was necessarily, because I personally hate wearing a suit, but I do—

C: They look so good?

J: No, but I love dressing up. The rules of like it has to be this and has to be tucked in.

C: That’s tough.

J: The thing is I don’t hate wearing a suit. I just dislike most suits that I’ve worn.

C: Yes. By the way, a man can wear a great jacket and a great pair of slacks and they’re not a suit.

J: Yes. I don’t know, I have a really fun, one of the most expensive things I’ve ever bought for myself was like this Alexander McQueen bomber jacket that’s silk and embroidered on the back. I want to be able to wear that in a space that like, it’s nice. It looks like a nice view thing. I want to be able to wear that in a place that maybe like 15 years ago would’ve been suit only, but well this is clearly me dressing up. Do you know what I mean?

C: I think that that’s, to me, I’m not like, for whatever it’s worth, I’m not a label person. I don’t really care about any of that stuff. I don’t care about designer stuff. This tiny dog is stretching—

J: For the listener. Penny Lane is sitting on the table between Chelsea and I, just looking perfect.

C: Just amazing. But I’m not into any of those things and for what it’s worth, my mother for example made a lot of our clothes growing up and a lot of hers. My mother was always very— Really instilled in us, you may not have a lot, but what you can have is manners, what you can have is putting in an effort. What you can have is personal style, all of these things. She made most of our clothes because it was much less expensive than going out and buying them.

For me, I think some of the most chic and attractive people I’ve ever seen are people who probably aren’t wearing anything super fancy. Maybe all this stuff is secondhand, or maybe they made it themselves. I think that what is really being out, what has fallen out of fashion is the idea of giving a sh*t. Of like putting an effort of almost looking like you’re trying too hard by trying it all.

J: I will say like, I don’t know, I’m thinking of all the different function I’ve gone to with you times, I’ve like been at a party with you or a wedding or whatever and you are consistently one of the best-dressed people at the event.

C: This is very sweet.

J: Consistently and never in a way, but to your point, I think what I love about it whenever I see you out is I know that it’s because you care about it not to impress anyone. Like it’s never, I’ve never been like look at Chelsea. She’s trying so hard. Do you know what I mean? I just think you, I’m like Chelsea just really does it. You always like nice, I don’t know. you always look, even today like you’re, like shut up and I was like she just always has a look on and it’s authentic and it’s, and you put in the effort and I think it’s really beautiful.

C: Well, thank you.

J: It makes so much sense to have the context of it. As someone, like you mentioned you changed socioeconomic statuses. You went from being someone who grew up not going to restaurants at all really to now living in New York, like going out, whatever. In terms of when you started— How do I want to word this question? What was your initial reaction when you started spending money on going out? Was it hard for you to do it? Was it like hard for you to bring yourself to go to a nice restaurant because you’re like, this is too expensive, it’s not worth it? Was it the opposite? Like what was your first—

C: No, no, no. The reason I started The Financial Diet is because I had gotten myself into terrible credit card debt and because I had— Generally, when people grow up not having a lot financially or not having enough, they typically go one of two ways. They either become extremely fearful of spending and very, very cheap with themselves, often to their own detriment. Or they become like, I can buy what I want. I can get this fake money on a credit card. I can go to the grocery store and no one’s telling me I have to take this out of the card like all of that and you spend, which is what I did so I got myself into terrible credit card debt.

J: You’re yelling at me.

C: I had a completely atrocious relationship with money. A lot of it was from spending from- I always phrased it as spending to try to be a different person. To be perceived in a certain way, to perceive myself in a certain way, to feel like I was moving. I also, for context, my adolescence I lived in a town called Annapolis, Md., which is very affluent.

J: I was going to say, rich town.

C: Well, I always say that like, so when I was very young, I was in a poor neighborhood suburb of Charlotte, N.C., where everyone was poor. When we were more middle class, when I was like a preteen, we moved to Annapolis, Md., where we were pretty middle class, but everyone around me was very wealthy. I felt way poorer then. I felt way poorer with the people who were around me.

J: I wouldn’t doubt that for a single second.

C: Among many jobs, I worked at the yacht club, which is like a country club for boats. Well, like literally you have to have a boat and it’s very expensive. I would like regularly be working bar mitzvahs where like Pit Bull was flown in to do a performance and sh*t like that. Or like weddings that cost $250,000. For me, just the being able to go into— The thing is that the thing that’s so dangerous about going out spending is that unlike— As I was saying earlier, like it’s still within reach of people who can’t afford it. Do you know what I’m saying?

J: Absolutely.

C: Like you can still probably cobble together enough to go out and get a couple of drinks or get dinner with your friends. Whereas like even a certain piece of clothing is probably out of reach.

J: Also, especially with like going out, a $500 night is built by like how many $25 purchases in rapid succession.

C: Or weekends.

J: Like crazy. Maybe a $500 night is a little more intense, but like a $500 weekend is 10 times being like “Oh, it’s $50.” Which is irresponsible, but it could happen. Do you know what I mean?

C: And it does.

J: And it does. Absolutely, and it’s also interesting, I wonder like the thing about the yacht club, it reminded me, I was trying to like articulate this to a friend of mine because I worked in similar places when I first got to New York, really expensive, really fancy parties, really fancy lunches. You’re trained to be like pouring this really expensive wine, pouring this really fancy food and you’re— The psychology of it is this wine is special because of X, Y, Z reasons and this codifies that this event has like meaning or importance because we’re doing this nice thing. Then you go back to throw your own birthday party and you’re like, well, my birthday party’s not as special if I just get Prosecco. Do you know what I mean? It’s a scam. You’re scamming yourself. Like obviously I love Champagne. I drink it rarely, but I love it. I would never buy 10 bottles of Champagne to make my birthday party more special at this point in my life fiscally. Do you know what I mean?

C: A hundred percent.

J: I think there was a period of time when I was younger when I was working where I was like, no, you have to get the nice thing, even though I wildly couldn’t afford it because I was like, otherwise this thing isn’t as meaningful because of the brainwashing that was happening by working in like yacht club-like spaces.

C: What’s really interesting about that is that if you do— I used to be an au pair for a very, very wealthy couple who I’m still very good friends with the mother, she wasn’t that much older than me, divorced from that asshole. He was one of those very prototypical, I don’t know if he was, like, truly nouveau riche, but just one of those that’s like he’s got to have this car because this is the car that means successfully.

J: Everyone’s got the G wagon. I got to get the G wagon.

C: If he’s going to the restaurant, he is going to order Champagne, not sparkling, whatever, blah, blah, blah, blah. One time my husband and I, because after I stopped working for them, we kept being friends and we would travel with them sometimes, and I could go on a f*cking two-hour tangent about that. One of the places we would go sometimes was their ski chalet in the Alps. When I tell you that this group of assholes that— There were so many aspects of it that were very Tom Ripley about like, what are we doing here? We’re like 20 years younger than all these people, like whatever, but they were all the definition of, and it’s not just any Champagne, it’s this Champagne. I know that Champagne is Goshen this whatever.

J: Or this year. All that bullsh*t.

C: We did a blind test with them, and of these five, six men who all have monstrous net worths and buy all this stuff all the time, not a single one was able to identify a single one of the sparklings that they were tasting. They don’t know what they’re buying.

J: No.

C: They literally have no clue what they’re buying and it doesn’t, but the thing is it doesn’t matter because like you said, it’s not about the quality anymore. It’s about what that product means about you.

J: I would say with that stuff personally, I think in a way it was almost never about the quality. I think it is about the quality for a very short period of time. Then the second it becomes like French Bordeaux being about quality, it was probably exclusively about quality hundreds of years ago. Once it becomes allocated to this thing that’s like hard to get and status it’s over about quality like no one cares about it. Do you know what I mean?

C: Yes.

J: I think that you could look at that as depressing, but I also think it’s really freeing because then you have to then just decide like what are the things I actually care about because there is quality in wine, you can train yourself to learn how to like appreciate the different palate and have that experience. Then the money is worth it if you decide that that’s where you want to go but don’t just do it because that’s not the path. You get to decide what is meaningful to you fiscally.

C: Well, and I will say between the yacht club and my extensive work as a nanny/au pair for very rich families— All of whom are divorced now, literally I don’t know what harbinger of doom I was, but it’s like a hundred percent batting average. Working in these really nice restaurants and all this stuff like I didn’t realize it at the time and I interned in D.C. at these like very fancy pants, cultural centers and stuff like that. I didn’t realize it at the time but my aspiration to live a certain lifestyle and especially not just financially, but in terms of culture, in terms of all these other things, led me to work for really, really rich people. Without ever explicitly trying to, I just was constantly surrounding myself by them as their employee, essentially as their hired help. I learned so much from those experiences that I’ve done videos about and written about my books. The one thing that I think it truly imparted on me beyond everything else was that, and the data backs this up for the most part, and there are exceptions. There are like the Ina Gartens out there, but for the most part, really wealthy people are not really enjoying their money. They’re not really even spending all that much time on activities where they even could be. They work way more hours than the average person and then they need to. They’re often much more influenced by markers of status than of quality. They’re inclined to spend on things that keep them on a very, very tight hamster wheel of lifestyle inflation. It was almost never, not never, but very, very rare that I was coming in contact with people who were very rich and living very fruitfully with that money. Really enjoying the sh*t out of their money, eating great food because it was what they loved, having the people they love the most around them interacting with their community. Very rarely was that the case. Again, the data really does back that up on a lot of different fronts. People talk about how money doesn’t buy happiness, which is a complete myth. It does to a certain extent, but what is true is that past a certain point of wealth, people do get unhappier. It’s not random. It’s because they’re very isolated socially from other classes. They’re pretty much only socializing with other people who reinforce that pressure. They’re working way more than they need to, and they’re not spending quality time with people they love.

J: Yes. It’s so real. It’s so wild. I was looking at a fashion brand. My friend works in the same building as a very luxury fashion house brand. I’ll just say it, it’s The Row. I was looking at their website and I was marveling. I think it’s f*cked up, but I was like, the genius of it. They saw the market of someone who needs to have a $3,000 sweater in the sense that they need the money, a $3,000 sweater existing makes the amount of money they have make a little more sense and derive a little bit more joy of like, “Oh, I get to go shopping for this sweat.” Do you know what I mean?

C: The most egregious in that specific niche is Brunello Cuccinelli.

J: I’ve never— I didn’t know.

C: I have a person in my life that I can’t be any more specific about who’s like the definition of the— What’s that phrase? An idiot and his money are not long for this world or whatever. Someone who’s the definition of who they’re targeting. When I say this is a place where it’s like $6,000 pants or whatever, but it looks like something you bought at Anne Taylor Loft. It very intentionally looks just like some random cardigan that a dentist would like, and I don’t mean that derogatorily, but I just mean there is absolutely nothing about it.

J: You’re paying emperor money for like a casual dad’s type.

C: It’s not even cool. It’s not even the row where you’re like one of those cool fashion girlies. It is truly just the most dreary suburban clothes. Sorry, I don’t want to say suburban negatively, but you have to look at these clothes because there’s something about it.

J: Pause the podcast. Google it.

C: Google Brunello Cuccinelli. You really look at that and you’re like, “Oh, you’re targeting mental illness at this point.” Do you know what I’m saying?

J: Yes. That’s the thing. It’s like the need to spend if you have like $30 million sitting in checking account and you’re buying, you buy every single thing on gap.com and it comes out to like a fraction of that. Do you know what I mean? You probably feel crazy, but if you rack up 40 grand buying stuff, you’re like, “Wow, how fortunate I have this money that I can afford to do this and buy these things that matter more.” You get to see you’re getting scammed

C: Like you said, it gives a reason for you to have it. There’s something to spend it on. I think there’s something to be said for the fact that like a lot of the designers that we think about when we think of designer and luxury clothing are not necessarily the clothing that the super wealthy are wearing. They are wearing things more like Brunello Cuccinelli or The Row, or maybe one of the super-elite lines from like Ralph Lauren and above all again, subtlety, discretion. You want to like, no one knows how rich I am, I’m just one of the normals, whatever. I think sometimes people can use that as a reason why it’s so silly to want an Hermes belt buckle or an iconic bag or what have you. I actually feel the opposite. I feel again, personally not a designer girly. I don’t really care for labels. I don’t like that stuff. If you’re going to buy something where for you it’s a symbol of achievement. It’s a symbol of whatever. At least it’s f*cking special. At least it’s something that you can identify as being outside of your normal rotation as opposed to going out of your way to spend insane sums of money to gaslight people into thinking you didn’t.

J: Yes, like buying $10,000 jeans that have holes in them. That’s deranged. It’s absolutely deranged. I don’t want to paint in too broad of strokes, but I’m sure when you tell people that you work in the personal— Was that the dog’s body that made that sound?

C: No.

J: Oh, it was this pipe. I truly was like, “Is Penny Lane okay?” Okay.

C: She’s so sweet.

J: She’s perfect. I think if you were to broad-paint a stereotypical broad picture of someone who runs a-

C: I’m sorry, she isn’t giving full-

J: She’s fooling just flashing the camera.

C: She is painting— You’re painting her like one of your French girls.

J: French girls, it’s giving Rose. That’s so funny.

C: God. Sorry. Continue.

J: No, it’s fine.

Katie Brown: She’s a very empowered woman.

C: She is. All right. This is for the only fans part of the—

J: This is Patreon. We are showing a Patreon for Penny Lane’s undercarriage. I think if someone were to make a very stereotypical unresearched guess of like, what do you think the life and aesthetic of a personal finance person looks like? They would probably picture someone who’s really type A and doesn’t dress— Do you know what I mean? It would probably be very dreary and I don’t know, like Angela from “The Office” or something like that.

C: Yes. There are a lot of those in my industry.

J: I’m sure.

C: Let me tell you.

J: I’ve never thought of you as someone like that.

C: Thank you, nor I.

J: You mentioned you used to have a very unhealthy relationship with money.

C: Correct.

J: You used to be maybe bad with money. What was the process of building a healthy relationship with money and a responsible relationship with money while still having a relationship with going out, dressing up, going out for cocktails, going to nice restaurants? I’m sure it was not easy or quick.

C: No. I think the most important mental shift that I made, especially as a woman because I definitely came of professional age in the peak “Girlboss” nonsense.

J: Absolutely, yes. I’m sorry, just for context, what age were you when this change was happening in your life? If you know what I’m asking? Late 20s. Okay. Cool.

C: After starting TFD was when I really went in earnest. I have to live a holistic life financially that supports the life that I want to live because I love to cook. I love to go out. I love home decor. I love all of these things and they’re all important to me and I didn’t want to give them up, but I also knew that I had to do so in such a way that I would, not be sabotaging myself financially, which has always been my problem. The thing about the “Girlboss” and even to some extent the second-wave feminism, there was so much bad about it, but one of the most insidious things, and even if we want to get into like the “Sex and the City” stuff is really teaching women that they could have it all in any capacity, or that it was aspirational to do so. I think the most important shift that I made was that you absolutely cannot have it all. No person can. Again, especially working for so many very upwardly mobile women who were trying to have it all, when I tell you, we’re talking about women who were probably taking in over $500,000 a year and living paycheck to paycheck.

J: Yes. When you say have it all, what do you mean?

C: To be able to— In the case of women’s empowerment, as fragile as that definition of it was, it usually meant something like a woman who is a mother, who is a career woman, who is very into physical fitness, who’s aspirational in terms of her personal presentation, who’s beautiful, who’s put together. The paradigms that you see on a show like “Sex and the City.” When I saw woman after woman up close who was attempting to be that. Who had an army of domestic workers, often including myself, and who were still failing at least one if not multiple of those different fronts at any given time, because we’re also talking about an ideal of aspiration that includes, for example, being quite thin, having limitless energy, having a very robust social life while also being a mom all the time, which is only so many hours in a day, girl, it’s not going to happen. The biggest choice that I made was I cannot have it all, I will not have it all, what do I want? For me, the biggest component of that was I’m not having children because I know that the things that are most important to me in life would be very, very reduced by having children through no fault of anyone’s. It doesn’t mean that you can’t have any of these things, but the extent to which I want, for example, freedom and options and the ability to travel when I want to, the ability to pursue creative and professional projects that interest me, the ability to make decisions on a more spontaneous level. Those things would take, by necessity, a huge hit. I’m not willing to do that. Financially, for example, the life that I live would also take a massive change if I were to have children. Similarly, there are other changes. For example, we bought a home that was below our means because I knew that I wanted to have a mortgage payment. I pay the mortgage every month, that even if I decided to— my husband didn’t work for a year because he didn’t have his Green Card and we were able to still afford our mortgage. Making choices like I don’t care that I’ll never have a washer dryer in my apartment or I only have one bathroom, or I’ll never own a car, for example, probably ever again in my life. I haven’t driven in 10 years. There are a lot of trade-offs that I make in my life because I know what’s important to me. Again, I’m still working with a flexible budget, but at the end of the day, I know that there are several other choices that I could make in my life that a lot of people in New York aspire to have a weekend home in which they will then necessitate often having a car and all of these other things. I think the most important thing to do if you struggle with prioritizing is to really try to draw a line in the sand of what are the things both tangible and intangible that are very important for me. You got to pick a couple and accept that the other ones are not going to be reasonable.

J: Yes. That’s I think a really healthy way of putting it. I think I’ve never thought about it like that, literal of terms, but I do think in a way that’s how I’ve approached my entire life in New York. It’s had to change a few— Do we hear that?

C: No.

J: Oh my God. Full sand in my throat. It’s had to change a few times, but I think that, and it’s hard. I think the challenge with that comes in, and I’m sure you experience this massively with the pressures that when is when your priorities don’t line up with others in terms of that. For me, a huge thing when I moved here was the only thing I care about is my career. I moved to New York to make my dreams come true. My lifestyle is I want every single bill to be as low as possible so that, because there is so much free labor that goes into being in entertainment, there is so much time that you’re not making money. I was like, “I need to have as low of monthly expenses as possible so that I don’t have to work as many hours at jobs that are not contributing to my career to make those ends meet.” Do you know what I mean?

C: Oh, absolutely.

J: I think that that was challenging at times when my friends who weren’t in entertainment were like, “We want to go here for the weekend.” It’s like, “I can’t, that’s not part of my reality.” I think that’s, but you got to f*cking do it, I guess

C: You have to choose and it’s also so important to remember, I know I’ve said it a few times, but it bears repeating. I have a combined income with my husband that’s higher than average, of course. You can have as much money as you want and still be in debt and still be living paycheck to paycheck and still be on.

J: If you’re digging a hole, yes.

C: If you’re digging a hole and if you are constantly living at the top of your means and trying to say yes to everything, which people do a lot more than we realize.

J: Yes. That is so interesting. Do you get, as someone who works in the personal finance space and is part of your job and career is suggesting what people do with their money, not telling them necessarily, but suggesting ways to, how do you phrase that? I guess I—

C: I was recently at a dinner with a friend of mine who is quite wealthy, quite successful, and did what I thought was not a super-smart thing when buying a home, obscuring all details, and I asked if it was okay if I shared a thought. He welcomed it and I said, “I would’ve done X differently. I think you can still do Y to kind of try and make up the difference a little bit.” Basically, to give some context, they put a lot down on a home, much more than necessary to have a low mortgage because I think there’s the- and they said as much that scarcity mindset of like needing that low mortgage but when those interest rates are rock bottom, especially compared to what you could stand to get in the market, there’s no reason to tie up all that cash when you can get a super duper cheap mortgage. You’re better off keeping a lot more of that cash on hand and for example, putting it in a well-diversified index fund-

J: To grow, yes.

C: -to grow. Those conversations I do have from time to time when it’s welcomed and in that case, I think there are also things that can be done. I think in general, one litmus test is I only say things if it’s something that could really help optimize with what someone’s already working with. I never ever want to be in the business of saying, “Oh, you shouldn’t do that. You can’t afford that.” Any of that stuff. That to me is a long road to nowhere and quite frankly, just really inappropriate.

J: I’m curious, do you get, because tying back to what I said earlier, you don’t have- your lifestyle doesn’t necessarily maybe look like someone who’s super frugal.

C: I’m not super frugal.

J: You’re not super frugal.

C: I’m very open about that.

J: Do people push back about you—

C: Absolutely not. No, I think the big misconception a lot of people have. The very first guest that we ever had on our podcast was a YouTuber at the time. She’s no longer a YouTuber named Ingrid Nilsen, who was very big on YouTube. Said in the first episode and set a precedent for people sharing numbers that I think she made something like $2,500,000 the year before on YouTube.

J: YouTube money is so crazy.

C: It is and it isn’t. We can go in that at another time.

J: No, it for the people. It’s crazy for it’s crazy.

C: For sure. She’s definitely someone who got on the right time and she shared the numbers very openly and the audience reaction was 1000% positive. We’ve also had guests on TFC who really try to obscure what they’re working with, but also who try to seem falsely relatable. That to me is- and that always gets a super-negative pushback. I did a video where I broke down everything I spent on my home, everything I spent on my kitchen renovation. I do those continually. For some people, they’re outlandish numbers. For some people, they’re within the realm. The point is, I think what people are very— I also have to say, it’s very important that I cover my bases with, I only make the fourth most at my company. I am very, very serious about paying people fairly, about benefits, maternity leave, health, all of these things.

J: As someone who is very, very close with one of Chelsea’s employees, she provides a very good quality of life.

C: Yes, and we have a four-day workweek.

J: I just want to say that you should be very proud of that.

C: Oh, thank you.

J: As someone who gets to watch a person who lives working for you. You should be very proud of that.

C: Thank You. I do take it very seriously, but I also look at it as what people really push back against, or at least what I push back against is a burning girly as someone who campaigns for the Working Families Party, all of that. Even in the most equitable societies, there are people who have more money. What we’re really pushing back against is, and what I personally push back against really strongly is other people I see in my industry and outside of it who are in my position as CEO or who work independently and hire people who don’t pay them fairly. I was recently at an event where I met someone who works for an extremely prominent YouTuber. Who was responsible for building this person’s business, essentially from zero, has no equity in the business, is paid pennies, can barely afford to live in a condo. Their boss, who is the figurehead, is driving around in f*cking Lamborghinis. That to me, it’s really that disparity and that unfairness and that selfishness and that spiraling towards further wealth inequality is what people really push back against. The fact that I have an upper-middle-class lifestyle in New York City, living in a two-bedroom apartment with my dog and my husband, people are fine with it.

J: Yes, because it’s not— God, that’s such an important part of the conversation. How do I word this? The people in my hometown in Vermont, you are wealthy by their standards. Do you know what I mean?

C: Yes.

J: I think that’s undeniable. The fact that’s the same word to describe Jeff Bezos is flawed because the level of wealth is not even in the same planet. That’s when the conversation is tax the rich, f*ck the wealthy, eat the rich. We’re talking about the rich, we’re talking about something very different than owning a two-bedroom apartment in Manhattan, which is still—

C: Which I bought at the height of Covid, by the way. It was very cheap, but continue.

J: No, but still that is you are fortunate— I guess the way to look at it is you are fortunate enough to be able to reasonably afford what should be baseline attainable to the average person in the American society and unfortunately is not. That does not mean you don’t deserve it. It means everyone else deserves to get it as well.

C: That is a very good point. I think the Jeff Bezos thing is really important. This is again, I always say we have the data for this, but we’re constantly researching this stuff for our videos. I have a lot of these numbers on top of my mind. It is a massive, massive social political economic problem in this country that people cannot visualize or understand the difference between a million and a billion. People think they’re similar, they have nothing to do with each other.

J: No. It’s actually crazy.

C: It’s actually crazy. I hope if nothing else, what’s happened with Elon Musk and Twitter will at least somewhat have the scales fall from people’s eyes that people shouldn’t be able to do this.

J: No, it’s crazy.

C: $44 billion, paying $1 billion a year in interest or whatever the numbers are. This is absurd. That has nothing to do with a person who lives in a decently nice house.

J: Absolutely. Slight pivot, but I’m just, do you and if this is too personal a question just deflect but—

C: Basically no such thing.

J: Do you and your husband have like a strict budget that breaks down and allocates what you’re spending each month on X, Y, Z?

C: No, we don’t anymore because we don’t really need to. We live below our means. I think a lot of people just have that—

J: That’s such a luxury to do that.

C: Pay yourself first.

J: It’s such a luxury to give yourself that, by living below your means you can then do things as well.

C: 1000%. This is something we talk about a lot on TFD if you want to save more money, build wealth, et cetera. There’s two ways, you spend less and earn more. For some people and I think everyone should strive to some extent spend less, most people would do well to look at their spending habits and say, “Are there things I can change? Are there things I’m wasting money on or I’m not getting a lot of value out of?” Because that’s the case no matter what you’re doing. Penny Lane. Oh, she’s kidding.

J: She’s just repositioning.

C: I’m one of those people and I think there are a lot of people out there who are very motivated by earning more. I try to have every year a few side streams of income inside and outside of my own business. Like most of my employees are, I’m on some variable compensation where I have commissions, bonuses, things like that for different projects. I also do sometimes things outside of my job, especially with the four-day workweek, because I’m personally quite motivated by the idea that for example, we’re doing some home renovations. I mostly pay for those. I know this is going to cost me $15,000, let’s say for a certain renovation. I am much more motivated at the idea of how can I make $15,000 incremental dollars this year.

J: Then to save $15,000

C: Then to save them.

J: Oh, 100%.

C: You still have to be saving, but if you are motivated by going out and earning more, I think that can also be a very powerful thing.

J: Absolutely. You mentioned earlier that your husband, Mark, who’s lovely. Is it okay that I said his name?

C: Yes, of course.

J: Okay. People are weird about that. They don’t like to name their partners or whatever.

C: He’s very offline. He works in tech, which I think is a common thing to work in tech and be offline. I mention his name all the time.

J: You mentioned he loves like the Per Se ask, tasting menu, gastronomy-type dining. What do you like, I guess.

C: My sweet spot in a restaurant, all my favorite places.

J: Yes. I guess I don’t actually know. we’ve never talked like spots. We’ve gone to great spots together.

C: Yes. My all-time favorite, no, I shouldn’t say all time. That’s too big a language. My favorite spot right now is a pretty new restaurant. I think it’s a Danny Meyer restaurant, which I know is probably triggering for you.

J: It’s okay.

C: It’s a female chef though. It’s Ci Siamo. It’s in this very strange complex on the West Side.

J: Yes, I’ve heard about it.

C: Right by Penn Station. Outside, you’re like, “What is this place? It looks like an office park.” It is, but-

J: Is Rosie the chef?

C: Hillary Sterling. Look at me knowing the name of the chef.

J: There’s nothing wrong with knowing the name of the chef.

C: If I like it. Especially with women in the industry, I like to follow them on Instagram and support them and stuff like that because it’s a tough world out there.

J: Ci Siamo, it’s Italian?

C: It’s Italian, but it’s definitely got a very decor-wise, vibe-wise, it’s a very “Mad Men” type of flair.

J: I’ve seen photos of this place, it looks absolutely stunning. I do want to go.

C: The food is exceptional. It has all those little touches when you get your check, there are these beautiful homemade almond cookies that come out with it. The cocktails are so special but it’s definitely not a Per Se level. It’s definitely in the very nice but not crazy level. Which is my sweet spot.

J: How much is it if you and Mark are having dinner there? How much is the check at the end of the night?

C: If we each do, let’s say a cocktail, a glass of wine or two, we split an appetizer. We each get an entree, we split a dessert, we’re probably out of there including tip, for $250 to $300.

J: Oh, okay.

C: Which is a lot.

J: If we’re saying the next-up level up is Per Se, that’s $1,000.

C: There’s probably one level in between the two of them, but yes.

J: No, there absolutely is. Just for perspective if people are listening and don’t know the difference in pricing.

C: Yes, but that’s my sweet spot. I love for me anything that is very experiential and has a very distinct— I love a theme. When I have dinner parties I like to have a theme. For anything that’s a red sauce Italian type place like Bamonte’s in Williamsburg where you dress up for it and there’s an experience. I love a steakhouse. I would say steakhouses are some of my favorite. My favorite one is actually in Philly. It’s Butcher and Singer.

J: I’m going to Philly next month.

C: It’s fabulous. Go there. I love everything about it. The food is so good, but there’s almost a sunken living room type of vibe with the dining room where there’s chairs up here or there’s tables down here. Then the real tables are the big beautiful semi-circle leather booths.

J: The brocade leather.

C: There’s wallpaper of dogs playing poker. It’s very “Mad Men.” All of that stuff, I just really love.

J: I adore that. Do you have any New York steakhouses you love?

C: I would say my favorite steakhouse in New York is probably 4 Charles Prime Rib.

J: I haven’t gone yet, but I’ve heard it’s wonderful.

C: It’s quite good.

J: Yes, I’ve heard it’s really good.

C: To me, you take me to a Keens, you take me to a Gallaghers, I’m having a grand old time.

J: I mean the same. I love that aesthetic because obviously Holly, David, and I are a crew and David’s vegetarian. The steakhouse doesn’t get in there with that restaurant crew that often.

C: Yes.

J: I need to wedge my way into one of them again soon.

C: You got it.

J: Have a wedge. I love a wedge.

C: A wedge salad is one of the all-time. We got to get dinner, man.

J: Have you had the wedge at Bernie’s ? I talk about Bernie’s every episode. Have you had the wedge at Bernie’s?

C: No, but Holly was really playing this place up to me.

J: Well, we just went there for— You can say, Holly. I said Holly’s name. We did my birthday dinner at Bernie’s a few weeks ago.

C: Oh, I know.

J: Yes.

C: I heard all about it.

J: It was so good.

C: Yes. I love that type of place.

J: The wedge is really stunning there.

C: I love a wedge. I love a Martini with blue cheese-stuffed olives.

J: Can I say that? I find that hard to find in New York.

C: Oh, I have a list.

J: Wait. Okay. Send it to me.

C: I also have a list— I’ve been doing a power ranking of my favorite French fries in New York City that I like. One day I’m going to like, I don’t know, just for fun, like publish an article.

J: That’ll be a huge resource to everyone.

C: Yes, I have a few specific— I keep a spreadsheet of different back-pocket places for if parents are in town or a birthday, this is a great private event but the fries is a big one that I keep—

J: Can you just name a couple that you love?

C: My two favorite French fries in the city, at least in Manhattan, both one of them closed, which was the NoMad Hotel. The bar at the NoMad Hotel.

J: You’re not the first one to tell me about those fries.

C: Those fries were f*cking incredible. That place is gone. The entire hotel is gone and then the other place was this place close to our office at Columbus Circle called Bluebird. The fries that are my favorite are like the really- they’re like a shoestring, but they’re like the buttered. They’re thin and super crispy, crunchy. I love the truffle fries. These were truffle with freshly grated parmesan.

J: We reading trouble. That’s when I saw you, I just realized.

C: They were mid.

J: Those weren’t great, but I was happy to have them.

C: I was happy to have them but those have both gone. There’s also a place I think your friend works there, Ruby’s.

J: Yes.

C: They have excellent fries.

J: Okay, good to know.

C: Yes, I’m a skinny fry girly.

J: For me, skinny is tough, and here’s why. Well, here’s the thing. If the skinny is so skinny that it breaks off in the ketchup.

C: Not bad.

J: That is infuriating to me. The worst fries I used to hate more than anything and I can disparage this place ’cause it got canceled. The fries at The Spotted Pig.

C: Disgusting. Those are like potato sticks.

J: I wanted to die when I ate them. I remember I have a vivid memory of eating— It’s also The Spotted Pig was a nice, well was— It felt like a place where you should have been looking nice. People were acting disgusting there but I thought I was being bad at The Spotted Pig by- you had to scoop all of these crumbs and eating the fries there—

C: It’s those potato sticks.

J: Hell yes. In the blue bag. Hell—

C: Horrible.

J: When someone tells me a shoestring or a skinny fry, I get nervous that’s where we’re going to end up.

C: No, we’re talking just slightly thinner than McDonald’s fries. And battered.

J: Okay.

C: There’s a real fluffy potato inside.

J: When you say battered, are they actually like thrown in a batter?

C: There’s a certain genre of fry that is literally battered. I don’t know what exactly the batter is, but oftentimes they’re- sometimes they’re literally battered. Sometimes they’re just like tossed-in cornstarch.

J: I was going to say there’s a thing where you put them in a cornstarch slurry.

C: They’re like coated kind of.

J: Yes. In the corn—

C: They have that coating, that crispy coating.

J: Yes. Well, they have the palate to catch that ’cause I bet 95 out of a hundred people would be like, “This is just potato.”

C: I love French fries. One of my— I have so many— I love to— My husband and I are both big bar eaters. We love to eat at the bar.

J: I really prefer eating at the bar.

C: We love to socialize. We’re both very — we love to meet people and have conversations.

J: Yes.

C: Chat with the bartender and all of that and people watch, we love that. We also love spontaneity in dining. I don’t love having a reservation as much. Sometimes, but I also just like to pull up.

J: We’re different there, but I get you.

C: Well, I like to be able to pull up and be like, “Oh, wouldn’t that be so— Would it be crazy if we went and had dinner there?”

J: Yes.

C: We can do that at the bar.

J: Here’s my thing, is that if there’s any we are getting di- if you and I are meeting at 6 and there’s something at 8, and we’re like, “We’ll just find a place to eat.” No, no, no, no. If there’s a time constraint and I’m hungry, we’re going to need a reservation but if we’re going somewhere without a reservation, knowing that we’re going to get drinks while we wait and make a night of it, I’m over the moon to do that. That’s my delineation.

C: I also love eating alone.

J: Yes.

C: That’s one of my favorite things is to take a great book and go eat alone and the fries thing started because I had a once-a-month ritual where I would go to a bar, usually the bar of a restaurant and I would get a drink and a big order of french fries just for myself and a book. That sensory. I once saw a very elegant older woman doing it, much older, and that woman was having the time of her f*cking life.

J: It was you from the future. You just saw a vision.

C: It was just like, “That b*tch knows what’s up.” Ever since and so now I’m on my fry journey.

J: I think that’s really gorgeous and I want to do that with tartare. That’s my version.

C: Tuna or beef?

J: I prefer beef, but I know that-

C: My husband loves beef tartare always-

J: I love beef tartare. I know that they like disproved it, but there was that, do you remember that there was that thing for a second where they thought your blood type was indicative of what foods you enjoyed?

C: That seems like it’s probably real, right?

J: I think it was more of a thing where they tried to make it into a fad diet, which was if you want to lose weight and you have type A, you should eat this, and then they were like, “Don’t listen to this,” but for a second it was type O positive, which is I am, which is the most common one. It was you really crave iron and blood and-

C: Might just be anemic, honey.

J: I was like, “Yes.” I don’t think I’m anemic. I’m built like a football player. I don’t think—

C: One of those anemic girlies.

J: I don’t think I have an iron deficiency, but I do just love— I try to mitigate it because it’s not healthy for you and I do have bad cholesterol, unfortunately, I found out recently, and also it’s bad for the environment to eat it a lot, but I do love beef.

C: Listen, my favorite compliment I ever heard someone give someone else was, I was listening to a podcast and the host referred to her guest as being a woman of great excess in the sense of she lives a generally quite balanced and reasonable life, but she loves a massage. She loves a good Martini. She loves a nice steak every once in a while. She loves like I do, sorry to say it, a cheeky cigarette every now and again.

J: Absolutely.

C: Just really enjoys those things. I think beef to me falls in that category. It’s certainly not something I eat every day.

J: Yes, but it’s indulging.

C: It’s not something we have at the house. I think it’s just one of those pleasures that if there’s something about it when it’s right and it’s why I love steakhouses so much because I don’t cook steak at home. I don’t really cook beef at home, so it’s just a special moment and I think if you’re able to— To me, anyway, if you’re able to keep these special things for these really curated moments and going back to the theta of it, it’s there’s, to me nothing more wonderful about being alive.

J: I know. I really feel that’s what I like. That’s also how meat used to be eaten. It was a celebration to have it.

C: Exactly.

J: I think that that is truly how it should be done and I do think that that is why steakhouses feel so special.

C: Also, there is just this is a such another on the level of my fry thing. Such a f*cking pet peeve. I love anchovies. I know it’s not everyone loves an anchovy, but to me, if you have a Caesar salad on a menu and it doesn’t have anchovies, it’s not a Caesar salad. You can maybe specify this is a vegetarian Caesar salad or whatever, but steakhouses are one of the few places, at least some of them where you’re getting a real-ass Caesar, sometimes tableside where they’re making it with the fresh egg yolk and the minced anchovy and stuff like that. I do feel like there’s a certain class of food that we’ve watered down. A good Caesar salad is paradigm-shifting, but 90% of the Caesar salads that you order at a restaurant are so sh*tty. They’re not even Caesar salads anymore.

J: It’s just like salty ranch.

C: It’s salty ranch and how have we diluted the pleasure of these things? I’d rather have one a year but have it be spectacular.

J: I think that feels really in line with how I know you to be. I know I would rather have—

C: It’s true.

J: You’d rather have— There’s a second dog has entered the building.

C: Oh my God.

 J: So I like to end our episodes by planning a night out together if we would like to have a night out together.

C: Don’t threaten me-

J: Let’s talk about this.

C: Yes.

J: I think we should go somewhere nice and fancy.

C: Obviously, yes.

J: Have you been to Aureole? Wait, that’s not what it’s called. F*ck, what’s it called? Can you Google? Google restaurant on Cortlandt Alley.

C: Down in the-

J: It’s in SoHo.

C: You’re not talking about Au Cheval.

J: Au Cheval.

C: Oh my God, that’s not super fancy, but it’s one of my favorite restaurants.

J: No, no. It’s not too fancy but when you said— Okay, no, but like, you-

C: Not me knowing what that was because I know it’s on Cortlandt Alley.

J: The only restaurant on Cortlandt Alley is Au Cheval. That makes sense I said Aureole. Aureole is an old Charlie Palmer restaurant. Au Cheval, when you were describing what you liked, I was like, “This sounds like Au Cheval.”

C: I love Au Cheval.

J: Because it does even though that is a place where some people do look like sh*t.

C: Let me tell you, there’s nothing I love more— Just, sorry, one note on that. Nothing I love more than a fancy lowbrow dish and their homemade bologna sandwich, they make a homemade bologna that’s fried.

J: Those burgers and the reason I was going to say, they have fries and one of the two best Vespers I’ve ever had in New York.

C: They sure do.

J: I thought that would be a nice place to start if we want to have a cocktail and a fry and then perhaps we just get a phone out. No, purely to be like, “Where should we go and find a nice restaurant nearby to explore or we get a steakhouse reservation.”

C: I like both of those. Where do you land on music with food?

J: That’s a really interesting question.

C: A trap door.

J: I went to one of my favorite Italian restaurants last night. I forgot that on Sunday nights they have live jazz and my stomach dropped because I don’t like when the music’s too loud that you can’t hear. These jazz players hit the perfect volume. It was live jazz but I could very comfortably have a conversation over it. There’s another restaurant that I don’t want to name that is somewhat in my neighborhood that some nights has live music where the event is the live music and the food has become secondary and then you can’t talk. That to me is a full nightmare and I would like to leave.

C: Got it.

J: Bars with DJs are my nightmare as well.

C: That’s not my—

J: I guess my thing is I am always going to want to be having a conversation. I’m not super interested in going to a restaurant where the thing is that you watch music and don’t talk.

C: I totally agree with you. What I’m saying though is that I think there’s a specific, if you’re going to go out downtown and start with a cocktail and a cheeky plate of fries. I do love the idea of going somewhere that has a little gentle piano, like an old-school Italian restaurant.

J: Absolutely.

C: Maybe the owner is getting up at 10 p.m. to do a little Dean Martin because to me it’s otherwise if we’re not going to go for something that’s a totally different but equally special vibe, then we just have dinner there. Do what I’m saying?

J: We might as well say Au Cheval unless we’re going to pivot to something very different.

C: Yes, really like white tablecloth Italian kind of a place.

J: I haven’t done that in so long that I would do that.

C: I love that. For the record, as you probably can tell, I’m a talker. I don’t like any place where we can’t talk but we live uptown. Across the park in Harlem are so many restaurants where there’s just a little lovely jazz happening and it just feels so special.

J: That sounds so nice. Wait, one question before we go because I am curious, what are your- because I lived uptown for three years, with Holly, but I was broke at the time. I feel like I didn’t— What’s your uptown spot? I’m just curious where’s the place to go up there right now?

C: For what?

J: Nice. I’m not saying big huge expensive date night but you and Mark want to have a nice dinner.

C: There’s a lot uptown that I really like. I would say if we want to get something that feels like a nice mix of typical, I believe locally owned but still a little special. I love B2 Seafood. It’s on, I want to say 120th and maybe FDB, between that and Manhattan or something. It’s really beautiful. It’s like loungey. They specialize in seafood, which we love. Great drinks. It’s also pretty close to this really exceptional cocktail bar, Sugar Monk, uptown. Which almost has a speakeasy, very lush boudoir lounge vibe. I love it. There’s also a new tapas place uptown that I really love.

J: Called?

C: Called Enoteca, I want to say. No, maybe. I’ll have to look into it, but I believe Enoteca.

J: Gorgeous. This has been one of my favorite episodes. This has been so, so great. Thank you so much for doing the show.

C: Thank you. I just really enjoyed this. I’m always talking about the most boring sh*t. I’m always having to go to— I don’t know, talk about like, “What are your best tips for using a credit card?” Which is important but this is fun.

J: I used all my- just to quick note of credit card points at the end of, I was in Scotland doing Edinburgh Fringe.

C: I heard—

J: I obviously was the most expensive thing I’ve ever done and I had two nights in London to myself before I came back because I was flying in and out of London and I could have stayed with friends for free but I was like, “I medically need a nice hotel.” I’ve never wanted to stay- because hotels are my favorite thing.

C: Oh, the same.

J: A really luxury hotel and I forgot I hadn’t because I had gotten hooked up with a flight by a friend who works for an airline. I forgot I had all my Amex points and I used them to get a hotel for two nights, and it was the greatest thing that’s ever happened to me in my life.

C: There’s nothing better, that robe, that mini bar, the cold Snickers.

J: Also, when I got there, I didn’t know this but the Amex partnership with this hotel and he goes, “By the way, for your two nights you have a hundred dollars of free room service.” I almost cried.

C: Wow.

J: Free room service was one of the— It’s going to be one of the highlights of 2022, for me, was that I had two nights for free.

C: Highlights of your life. Highlights of your life. Also, I would just to say, speaking of my work, maybe Holly told you but you’d be pleased to know that several of the girlies organically shared your TikTok about why sweaters are hot. It’s in the chat and everyone was like, “Jake is so funny. I can’t believe Holly knows him.”

J: Oh gosh. Bless.

C: You have many fans.

J: I’m a big fan of The Financial Diet.

C: Thank you. Thank you for having me. This has been such a pleasure.

J: Oh, this is great. Oh, yay.

Thank you so much for listening to “Going Out With Jake Cornell.” If you could please go and rate and review us on whatever you’re listening to this on, that would be really gorgeous for me in a huge way, so thank you.

And now, for some credits. “Going Out With Jake Cornell” is recorded in New York City and is produced by Keith Beavers and Katie Brown. The music you’re hearing is by Darbi Cicci. The cover art you’re probably looking at was photographed by M. Cooper and designed by Danielle Grinberg. And a special shout-out to VinePair co-founders Adam Teeter and Josh Malin for making all of this possible.

The article Going Out With Jake Cornell: A Cheeky Cigarette (w/ Chelsea Fagan) appeared first on VinePair.