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How Do I Deal With My Rich Friends?

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On this week’s episode of The Cut, co-host Jazmín Aguilera tries to find a solution for how you can broach the often-uncomfortable subject of money in your different friendships, especially when you don’t make the same amount as a friend. Talking to TikToker Tom Cruz, who went viral for showing the world a spreadsheet of his friends’ incomes, she learns about radical transparency when it comes to managing friends and money. Then, Otegha Uwagba, the author of We Need To Talk About Money, teaches Jazmín how to deal with friends who are much wealthier than you.

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To hear more about navigating money conversations with friends, listen below, and subscribe for free on Apple Podcasts or wherever you listen. You can also read the full transcript below.

JAZMIN AGUILERA: Having friends means going out, doing activities together — in short spending money. And since all my friends are from different backgrounds and make different salaries and have different values when it comes to saving and spending money, I still don’t know what the proper etiquette is when the bill comes. I haven’t yet mastered this dance. So instead, I just insist on paying most of the time. And that’s unsustainable. Obviously, because I can’t pay for everyone all the time. And then I start to fall down this rabbit hole of who deserves to be treated? And who should I split a check with?

And to make matters worse, since I moved to New York City, a lot of the social tension around this very problem has been turbocharged. Because this city is home to some super-rich people. The kinds of people who will never ever have to worry about making a living for the rest of their lives. And some of them are my friends. And I hope this doesn’t make me a bad person because I don’t wanna pay for them! I don’t even wanna split the bill with them. Like … If my apartment can fit inside their apartment 4 times over — well, then, maybe they can offer to pay once in a while! Am I wrong about this?

Do the same, mysterious unwritten rules apply to them? How does this dance change when the wealth disparity between us is so great? It’s all very confusing. Made nearly incomprehensible because we just don’t talk about this kind of thing. I mean, not really. So, I want to talk about it. And so this week The Cut is collaborating with NPR’s Life Kit to figure out the best way to approach the sticky situations that come up around money and friendships.

TOM ON TIKTOK: So a few years ago, my friends and I started making a spreadsheet, breaking down our incomes and availability for travel. And it looks like this. This is incredibly helpful um if you have your friends broken down here from Sean, my top-earning friend who makes over $5 million, to who we call Broke Bob who makes $125,000.

JAZMIN: So Tom Cuz posted this TikTok showing off the spreadsheet and understandably, it went viral. It got a lot of backlash, as you can imagine. When the bottom earner in this spreadsheet makes 125k dollars a year and is labeled “Broke Bobby” … well, you know that’s the term that’s gonna trend on Twitter.

TOM CRUZ: I get it. I get why people are pissed off that we call him Broke Bobby, because the way that they relate it is like, “If he’s making three times as me, then I’m destitute,” and people make funny jokes about that. That’s not the point.

JAZMIN: So what is the point then, Tom? Because it seems to me like an invitation for a Twitter dragging if I have ever seen one. And of course, Tom was flooded with DMs calling him out for ranking his friends, for centering money in his relationships, for even sharing this financial spreadsheet. And listen, I had the same reaction when I saw these posts. But social media is a prism of lies so I just had to know…are finance bros really like this? Because if so, yikes. But there’s just got to be more to this. So I gave Tom the benefit of the doubt and a chance to explain himself … and this cursed spreadsheet.

TOM: It started originally when we couldn’t agree on what we were going to do in Vegas.

JAZMIN: Tom and his friends graduated college in 2010, and they wanted to stay in touch and plan some bro trips together. Being all business or finance or tech majors, (because of course, they are), they wanted to organize all this info into one place.

TOM: I would have expected them to actually create a whole SAS software platform to track this for us. But we just settled on a Google spreadsheet.

JAZMIN: So Tom and his friends started what he called “a humble” spreadsheet, where the top earner made only $150,000 a year. You know, just a few post-college buddies, trying to go to Vegas by sketching out how much time people could take off (normal), how much people might want to drop on a weekend trip (normal), and their salaries and projected income (not normal). But, bruh, this was all in service to the party gods!

TOM: This is what happens when you have anything more than six people — and I’ve been to enough bachelor parties to see how much of a cluster this becomes — if you go and it’s not planned, then it’s just dudes hanging in a hotel room, drinking, waiting for something to happen. I hate that. I hate walking around in groups of just guys with nowhere to go. It’s weird. There’s no itinerary.

You can’t do anything in Vegas without a reservation now. That’s all stuff that has to be pre-planned. That’s where it started. And then it just became more of a dick-measuring contest, if you will.

JAZMIN: [Laughs.] So it’s fair to say that your friends were totally on board with this.

TOM: No one really cared. It’s just money. I think that’s kind of the biggest thing, was people worrying about the transparency of how much you make. I don’t know why that was ever taboo.

JAZMIN: So it sounds like you’re taking the uncomfortable elephant in the room and just shining a big old spotlight on it, like extreme transparency. Is this how you deal witH all of your friendships, like an extension of business? It’s not business, but you know what I mean?

TOM: It is. With my friends, if we’re making plans or if we’re going to go into business together, I’m always very upfront about it. I’ll let them know like, “if you’re not going to be pulling your weight in your role, then we’re going to have to have something in here where I can buy you out, or you can buy me out. If we’re not happy.” I’ve always been very transparent upfront because it just never works. In business or personal matters, if you’re not transparent or honest with what you want, then resentment builds and then you lose a friend. And at that point, it’s obviously not worth it. When you’re this transparent, they have no out. They can’t say, “Oh, I didn’t know that. Or I didn’t know that’s how you felt about it.” Like, “We’re going to Vegas. We’re going to spend a hundred thousand dollars this weekend. Do you want to come, yes or no?” The answer is “okay,” or “not okay.” There’s no getting there and being like, “I can’t do that. I can’t go to the club,” or whatever. We try to avoid that.

JAZMIN: For the spreadsheet itself, I can see the upsides in that. It makes it easier to communicate and efficiently plan something, and it has this weird added benefit for you and your bros to have this dick-measuring contest, and it’s in good fun. Are there any downsides for you guys?

TOM: We haven’t seen any downsides. As far as I know, no one’s had any hurt feelings about it. We never exclude anyone. It’s not like there’s a clique, like the top five and the bottom five. I would actually argue that I hang out with some of my lower-income friends more than I do my higher-income friends, because coincidentally, or more ironically, they have more time off. Most of the time I’m hanging out with or going on vacation with, some of the friends that are in that $150,000 to $250,000 income range.

JAZMIN: I’m sorry. I can’t help but laugh right now because it’s so funny to hear you talk about, “my lower-income friends,” in the $150,000 to $250,000 range.

TOM: I mean, it’s all relative. When you look at it in a vacuum, it very much looks like a douchey, classist, tone-deaf, read the room, Tom, kind of thing — but this is normal. Very few of them, I think, had a silver spoon in their mouth when they were born. It’s not like these are trust-fund babies. Most of these people were self-made, and that’s a big reason that we have a lot of stuff in common and we hang out with each other.

JAZMIN: Yeah. By the way, I’m not laughing at you. I’m just …

TOM: I know. I mean, I’ve gotten that.


TOM: I understand the ridiculousness of it. The average median income in the U.S. is $50,000.

JAZMIN: It’s actually a little bit higher than that. But definitely not $125,000 a year. So, what about THOSE kinds of people? Average people – the ones who make $60,000, $70,000 a year. Is Tom not friends with any of them? Is “Broke Bobby” the cutoff point for him? So, there’s actually another list. It’s called “The Welfare List” — to be clear, none of these people are on welfare.

TOM: That was the bottom income earners and that was started by another friend of mine.

JAZMIN: Doesn’t this self-select your friends? Doesn’t that mean when you go on vacation, like doing these bonding trips, if you want to have an absolute super dope baller time, you can’t do that with the welfare list? You’re automatically building stronger relationships with people in your own “class,” right?

TOM: No, that’s not true. I’ve gone to, for example, Lake Tahoe with some other friends, and we’ve rented boats and been on the lake and had the time of our lives. You don’t have to spend a bunch of money to grow strong bonds. That’s why I’m friends with both groups of people.

JAZMIN: Does this level of transparency encourage friendships across like the salary bands? Do you find people from the bottom being like, “Oh, I want to be friends with these people up here more”?

TOM: I would say it’s more encouraging. I have friends that would have never talked to some of my higher earning friends but now they have because they’ve hung out in the same circle. They’ve met through there and there’s definitely built-in networking into a list like this. I’d say that’s been a positive.

JAZMIN: At the core, this is solving a communication problem.

TOM: It’s a communication problem. It’s a planning problem. It’s a transparency problem. It resolves a lot of that.

JAZMIN: And it never ever at any point made you feel weird.

TOM: Yeah. And that’s really the only criteria. People like that don’t care about talking about money. And if they do, then they’re not on this list.

JAZMIN: Tom Cruz has this idea that being radically transparent about money with your friends is the way to go. For him, the spreadsheet helps his friend group manage expectations around big-ticket hangouts and prevents money hiccups and misunderstandings. And it also kind of gamifies friendship. And it seems like it’s worked for him and his finance bros.

But is this the kind of thing that’s easy to do when you’re not rich with time and money? When you have crushing student loan debt, sick relatives that need expensive, round-the-clock care, or if money was always an issue in the relationships around you growing up. Or any other of the million reasons why we could feel awkward being transparent about our finances with our friends. They’re the people who are supposed to understand us inside and out — yet letting them know the inside of our wallets is a whole other level of intimacy. So what do we do if we find ourselves uncomfortable talking about money with our friends?

I have a friend who’s rich rich. Like, heiress-level rich. And I’m not — like at all. And that brings a whole new set of awkward money questions into our relationship. Mainly, I get the feeling that my friend is insecure that people only want to be friends with her because of her money. And I wish that she could just know all of the glitz and glamor that her wealth might bring don’t hold a candle to the simple act of Just Being Friends. But I have no idea how to even start that conversation with her.

OTEGHA UWAGBA: It’s weird because regardless of which side of the wealth divide you’re on, we find it difficult to talk about it.

JAZMIN: This is Otegha Uwagba, and I talked to her to help me figure out why it’s so weird for all of us to broach money conversations with friends. And she gives me some concrete advice on how to jump the yawning wealth gap that’s preventing me and my rich friend from getting real about our friendship.

I’ll give you a little bit of background on me first, to give you an idea of what I’m going through right now. I came from a pretty working-class, middle-class social circle back home in California, and then I moved to New York City. I found out that a couple of my friends were incredibly rich. Ranging from money that I would love to have to money I can’t even imagine having. It came as a surprise to me. It was this big elephant in the room. I don’t really know how to talk about it with them.

OTEGHA: It’s interesting because I have had a similar experience, in that I grew up without a lot of money, and I’d say kind of borderline working-class/lower-middle-class, but I ended up getting a scholarship to a really fancy private school. Then I went to Oxford, which is a really elite university. So actually for most of my life, most of my friends have been from a wildly different socioeconomic group than me. I definitely relate to discovering that your friends just have these endless piles of money. But I think because that’s something that I kind of had in my teenage years, it didn’t really come as a surprise to me. What did come as a surprise to me, when I reached adulthood, is how many of them had family money that would enable them to buy properties, which in London is very hard to do, as I’m sure in New York or any kind of major city. It’s only recently that we’ve started having those conversations. I think part of it has been down to me writing this book and them knowing that this is what I’m working on and that money is my subject.

JAZMIN: In that case, what conversations about money should we be having with our friends and what kinds of boundaries should we set with them at the outset? Have you worked out any kind of strategies?

OTEGHA: The main conversations I have with my friends are in a social context. Like, “do you want to go to this restaurant? Do you want to go on holiday?” Just last week a friend said, “Hey, a couple of us were thinking of going to Mexico for the New Year.” And I just said, “I’ve had a really expensive year. I also had a really nice holiday over the summer. I don’t think I can afford this one. I’m going to sit it out.” She was totally understanding, but for me, one of the key conversations is being honest and communicating what you can or can’t afford. And being honest about your limitations, both with your friends and with yourself. I think self-delusion is one of the most expensive habits, trying to keep up with your friends or compete with friends who have more money than you do.

JAZMIN: Yeah. Have you ever come into a conversation where you want to approach the topic, you want to just air things out, especially with somebody who is wealthier than you, and they don’t want to?

OTEGHA: I have. A scenario that I wrote about in my book is when I was 27 or 28. At this point, I was like, I’m never going to be able to get on the housing ladder, but I had a friend who had bought a place when we were 24 and I knew that she’d had help from her parents with the deposit. I knew what she’d been earning at the time that she had bought this place because we’d been doing the same job. We’d worked together, so I knew her salary because it was the same as mine. I was crunching the numbers and I was like, I don’t understand how she got a mortgage to afford this place, even with help in the deposit. I just don’t get it. I went over to her place once and I just kind of said, “Hey, I’m trying to get my head around this mortgage thing. How did you get a mortgage? Could you explain that to me?” And she suddenly got very awkward and then it transpired that she didn’t have a mortgage and that her parents had bought her the place outright and she had spent the past five years omitting to mention that. I think the word is lying to me and various friends about it, for her own reasons.

At that moment, I had to explain to her why it wasn’t helpful. I was like, “it’s completely skewed my perceptions of what is and isn’t possible with housing” because I’ve gone into that conversation thinking that she was going to tell me about this loophole and the loophole was just family money and I was like, “Oh. Okay.” But I also had a conversation with her about why she had told people this. I guess she didn’t want people to think that she was rich and then potentially take advantage of her and of her generosity or expect things.

JAZMIN: Yeah, I’ve definitely been in almost the exact same scenario where a friend of mine who was much wealthier than me —I had no idea she was much wealthier than me— she invited me to her place and that’s how I found out. Because there was just no way that somebody could afford a house like that in the middle of Manhattan. If you’re born rich, you can’t help that, just as much as I can’t help how I was born. But letting go of that resentment feels like I’m just adapting my situation to rich people and my discomfort rather than prioritizing my own feelings. So I want to do both. I want to show the rich people like, “I understand you’re also human. Just be human with me. Just be authentically you and just don’t be rude about it. And I will do the same,” but I can’t seem to make that connection as well as I’d like to.

OTEGHA: In my experience, that resentment tends to arise when people are either dishonest or oblivious about their good fortune. I’ve had a friend who did really well professionally and started this business. It’s made her a lot of money. But because she’s kind of gone from just being an average person to a not-so-average person in terms of wealth, she really understands what it’s like so I don’t feel that kind of resentment towards her or feel put out by it because she hasn’t lost touch. She’s very well aware — like she’s painfully aware — of her good fortune, versus someone who has just kind of always lived like that or isn’t aware, or thinks that’s just what life is like for everyone. Maybe you’re being a bit harsh on yourself because I think you’re also responding to other people’s not great handling of their own situation.

JAZMIN: Yeah, I love this. You’re validating me so much right now. The last thing that I would love for you to validate is that I’m afraid to bring up money to my wealthier friends because I’m afraid that they’re going to think that is the reason I’m friends with them. I can tell that it is a number one fear. One of my friends, for example, is deathly afraid that people are only friends with her because they assume that she’s going to hook it up constantly. I end up spending more money than I want to just to make things simple when we hang out because I don’t want to have that tension hanging in there like, am I hanging out with you because I want to hang out with you? How do I stop that whole tension and without making it awkward? How do I lay that foundation that “I’m not friends with you because you can get me into these parties or you have this amount of wealth?”

OTEGHA: You kind of have to suck up that it is going to be awkward when you have the initial conversation that I’m going to advise you have. An honest conversation and a neutral setting, it’s not the next time you guys go out and when you’re at a really expensive restaurant or bar or whatever, but maybe if you’re going for a walk or she’s over at yours and just suggesting alternatives and things that you can do that are maybe a little bit more in your budget and just be really honest. Say, “we are not in the same financial position and I don’t want our friendship to be based around what we can do with each other that involves spending money.”

It’s one of the weird silver linings of the pandemic. I realized how much I could sustain certain friendships without spending money because we couldn’t go out. We couldn’t go anywhere. And so there were a lot of phone calls and a lot of walks in the park. When restrictions eased, there were a lot of dinners at people’s houses. It made me realize how we got into this cycle of thinking the only way we could socialize with each other was to go somewhere expensive, service charge, and get an Uber home. That was all periphery to our friends.

JAZMIN: Yeah, absolutely. I’m going to step back and do a big general overlook here. What do you think we are getting wrong about money and friends?

OTEGHA: I think one of the most toxic emotions around money can be shame. I think that can be the thing that just emotionally stops people from making progress in how they feel about money. I think I’m always really keen to say that just talking about money isn’t necessarily going to change your material reality. I think that is kind of like a school of thought that is also being popularized. I don’t agree with it, but thinking about it on a personal, psychological, emotional level, I think one of the best ways to alleviate shame is having conversations with people in your life or conversations with therapists. I think we’re really conditioned not to talk about money and not to admit to some of our more base instincts and some of our more negative emotions, whether it is jealousy or bitterness or resentment and all these things. It keeps us trapped and it keeps us locked and it stops you from really establishing a healthy relationship with money. That’s the main reason, not to name-drop my book, but that is the main reason that I think that we need to talk about money because it absolutely can be transformative for how you feel about money.

If you want more specific, situational advice on money and friends, you can listen to an extended version of Otegha’s and Jazmin’s conversation on NPR’s Lifekit. Their version of this episode is coming out on December 9th, or Thursday of this week. There, you can hear some more actionable advice on money and your friends – everything from lifestyle inflation to accepting lavish gifts to splitting the bill.

How Do I Deal With My Rich Friends?