
A narrative podcast uses humor to explore reasons why so many people have personal debt.
Loading summary
Jamie Allison Feldman
Foreign.
Alison Stewart
This is all of it on wnyc. I'm Alison Stewart. Brooklyn based writer Jamie Allison Feldman told the world she was in debt. Big debt, almost 18,000 in credit card debt. And she did it on TikTok. Let's take a listen.
Caller - John from Monmouth County
Or we will.
Alison Stewart
Hear it maybe soon. That's you.
Rachel Webster
I have a lot of debt.
Jamie Allison Feldman
It's partially because I was irresponsible with my money and partially because I was never taught how to manage my money. Partially because I like stuff and stuff costs. Money.
Alison Stewart
Stuff costs. I love that I like stuff. Now she and her best friend launched a podcast and it's all about debt and our cultural beliefs about people who have it. It's called Debt Heads. Together, the two of them tackle topics like credit card industries, predatory tactics, finance influencers, consumerism, attorney leave, severance, the multitude of ways America are getting by in today's economy. The producer and host of Deadheads podcast, Jamie Allison Feldman, and Rachel Webster are here with me now. As you can see, it's just like you guys.
Jamie Allison Feldman
Yeah, exactly the same. Exactly the same studio setup, same windowless closet that we're in with, you know, towels over our heads. Same exact thing.
Alison Stewart
Listeners, we want to hear from you. Do you have personal debt? What kind is it? Mortgage, student loans, credit cards, medical debt? How are you dealing with your finances? What kind of decisions have you made because of debt? How has it affected your mental health and your relationships, maybe your social life? Give us a call. 2124-3396-9221-2433. WNYC. It is a judgment free zone. I'm going to say to everybody who calls in, first of all, Jamie, you log onto TikTok and you tell the world you are in deep debt. What led up to that moment?
Jamie Allison Feldman
Oh, gosh, so many things. You know, I think I am a theater kid ultimately at heart. And so anytime I've ever done anything, it really requires, like, some sort of audience to keep me accountable. And once I discovered, once I was able to acknowledge that I was in debt, I decided that the only way I was gonna actually stick to a plan is if I was held accountable in some way. And TikTok seemed like sort of anonymous, which seems naive in hindsight, but I was on Instagram mostly. I wasn't on TikTok, so I felt like here's a place where I could make a personal diary of sorts.
Host/Interviewer
She's your bestie.
Alison Stewart
Rachel, what did you think when you heard this? Because you didn't really know.
Rachel Webster
Well, I think it's just like Any friend that, you know, unless they're in crisis, you just assume that they're okay. But when she admitted to me at this point that she was, like, severely. Had been severely in Dove for years at that point, and she just had this look of, like, a deer in headlights. And I was like, this is very serious. We need to take this really seriously. This is like an emotional mental health situation in addition to, like, a practical thing. So we actually dropped everything we were doing that day and went straight to my office, and we sat and we just like I said, get out all your bank accounts. We're gonna put numbers into this budgeting app and we're gonna look at the numbers. And that, I think, was just really critical, the holding her hand so that we could, like, look at it together because it's so overwhelming when you.
Jamie Allison Feldman
To face it alone.
Rachel Webster
Yeah. You don't wanna even look. You don't even wanna open your banking statement when you're in debt.
Host/Interviewer
Did you consider that being a good friend by getting an app out and.
Alison Stewart
Putting all your stuff in it?
Jamie Allison Feldman
Yeah. Well, first I was mad at her. She was like, you need to look at everything. You've spent money, six months. I was like, get out of here. And then quickly, as soon as I started to confront it and look at it, I was like, she's right. I had to cancel plans. She made me cancel. Get on the phone and cancel a dinner I had that night. She watched me do it. And, you know, ultimately, I felt so lucky because I had been living in, you know, in shame and isolation, and I was afraid that she was gonna judge me or, you know, feel like I tricked her into being my friend all these years when really I'm this bad person with this big secret. And the reality was just so different from that. And it was. It really, you know, I was so grateful.
Host/Interviewer
Did you have to change the way you dealt with Jamie? Did you say, like, oh, let's go out for coffee? Oh, let's not go out for coffee?
Rachel Webster
I think I was already that type of person. Relatively frugal. I find fun in things that don't cost a lot of money. That's just sort of the way I live my life. That does not mean I'm not in debt for other reasons. But we, you know, I just said, this is how we already live our lives. Like, we have so much fun making fun everywhere we go, everywhere we walk, we have fun. You know, we. We go to the library, we go to the park, we make dinner at home, we make cocktails at home.
Jamie Allison Feldman
We see fountains. We go to the park and see fountains.
Rachel Webster
Like most of New York apparently. Yeah. So I think that we just. It was easy to kind of pivot her into my scene, which she was already mostly part of.
Host/Interviewer
But one of the things that was interesting in the podcast is the shame that came along with it and some like kind of nasty comments. That's why I said this is a shame free zone in this conversation. Let's take a listen to a little bit of episode one.
Jamie Allison Feldman
Joining TikTok felt like the wild west where no one knew anything about me or anything I'd ever done before. What is this place? I don't see anybody. I know just one tumbleweed. And the sounds of crop top teens dancing in the glow of their ring lights behind the saloon door. This would be the perfect place to start a video journal chronicling my journey out of debt. Who in their right mind would watch a 30 something year old drone on about credit cards? So I hit publish and sent my very first message into the void. But wait, it's not a void. It's a 21st century social media platform with over a billion users. And even though I'd come across plenty of trolls in my time on the Internet, once I started talking about money, they suddenly had a lot more to say.
Rachel Webster
Should we read some of these?
Jamie Allison Feldman
Ah, we get someone else to read them.
Rachel Webster
Here to read the best of the worst comments from Jamie's TikTok is our third grade friend, Dottie Mae Merchaum.
Dottie Mae Merchaum
Yikes. I'm glad you're in debt. You deserve it. You're delusional. You're tricking yourself and being rude to others. Girl, those nails look so bad. How do you live this way? Geez, what a child.
Host/Interviewer
And first of all, having a little kid tell you that is hilarious.
Jamie Allison Feldman
Really turned the script around. Also shout out to Rachel's sound design because that's all on display in that clip.
Rachel Webster
Yeah.
Host/Interviewer
What had surprised you about the negative comments?
Jamie Allison Feldman
Nothing, honestly. I mean I think it's really easy for us to focus on the negative comments which I have been doing. I've worked in journalism for a long time being public facing and it's easy to forget about all the nice things and the people feeling seen and just focus on the negative. But it wasn't surprising to me. I think, you know, we already know that we live in this sort of shame based system and people have really strong reactions. They're like triggered by hearing that someone is living their life while in debt. So it wasn't surprising. I mean it wasn't easy, but I don't necessarily think it was that surprising.
Alison Stewart
Yeah, we got a text here that says I have 7,000 in credit card debt and 4,000 in tax debt. It's terrifying and anxiety inducing. As a 29 year old who just got her life together to think about this as I am barely getting by as is my therapist is helpful for managing that anxiety. But my God, how do I fix this? I choose to pay down my debt and eat from food pantries currently. That's a really hard place to be. I don't want to say. What advice would you give her? But where could she start? What do you think?
Rachel Webster
I think it's really important to recognize that this is the majority of people right now. This is not. You are not failing. This is systemic. So please drop the shame. That's the most important thing. And really start to talk to people in your life because that's the first step. You need to admit what's going on so that you can let go of, you know, the secrecy and, you know, live your life and start to address it. We do not have concrete advice beyond that because, you know, it's exactly what we're exploring in our podcast.
Jamie Allison Feldman
Most people don't make enough to get by and, you know, there are services, there are things that I looked into. You know, I transferred my debt to a 0% card for a number of months. I know that there are services offered by the public library where you can speak to a financial counselor. But again, we're more just like, we need to be talking about these systems and how we got here in order to even imagine what a different future could look like for all of us.
Alison Stewart
And it's really great the way you talk about it on the podcast because it's a little bit funny. Like you said, the sound design is awesome. How did you decide, decide how you.
Host/Interviewer
Were going to tell these stories?
Rachel Webster
Well, everything that we've ever consumed when it came to finance or the economy was either boring, depressing, or boring and depressing. And we were like, that is not a good place to engage. Right? Like, the only way to make any change in the systems that aren't working is to actually be able to face them. And so we thought, you know, like Mary Poppins says, like, a spoonful of sugar might help. But also, like, I think it's really important that we are just lighter in general when we're addressing the difficulties that surround us. And if we can have a little bit of levity, a little bit of self deprecation, then it doesn't feel like the big monster that most people feel like it is.
Jamie Allison Feldman
And also, I think, you know, we're not trying to reach the people who are already consuming finance content. Right. We're trying to reach people who, like us, are not necessarily always thinking about these systems critically. And the way that we do everything in our lives I think is like, with a hint of sarcasm. And so we were like, that feels like the best way to reach a wide number of people.
Host/Interviewer
A narrative podcast investigates the reasons why so many people are dealing with debt and how to talk about it. It's called Debt Heads. The creators and hosts of the show, Jamie Allison Feldman and Rachel Webster, are here with me to discuss the show and to take your calls. Let's talk to John from Monmouth County. Hey, John, thanks for making the time to call all of it.
Caller - John from Monmouth County
Hey, I have a question about the big debt, which is a mortgage. For a variety of reasons. I'm paying a mortgage till I'm 79 years old, a 30 year fixed mortgage. And I'm putting extra money towards it, thinking, you know, I want to pay it off early. But I've recently been second guessing that and thinking might do better things with that money, that extra money I'm throwing towards the mortgage and maybe, you know, invest it and do better. I don't know if you're guests had any thoughts on that.
Jamie Allison Feldman
We're really happy for you that you have extra money to invest in your mortgage. Anyway, I've heard that's the advice that I've been given too.
Rachel Webster
I my husband's understanding is that if you have a really low rate at this point, you should just keep that low rate forever and pay the least amount and invest it other ways. But please do not come to us for financial advice because we are not experts.
Host/Interviewer
Yeah, it was interesting when you talked about the experts that you would find in a field. They were the ones inducing the shame on people. You were talking about Dave Ramsey.
Alison Stewart
It's your fault.
Host/Interviewer
You should save more. I'm going to be generational about this. What do you think people don't understand about your generation and debt? Because I think it is very, very different.
Rachel Webster
Yeah, it absolutely. As we just released, our latest episode is all about the generational shift. And there's a series of cultural and political things that change right at the beginning of the millennial generation, late 70s and early 80s, that changed the landscape for young people trying to grow up. And we're still following the dream of the boomers, which is, you know, buy a house, have some kids, go to college, two And a half kids.
Jamie Allison Feldman
Exactly.
Rachel Webster
Exactly right. And yet there has been so many things that have changed how that can be possible for so many people, especially people who come from, you know, lower income families.
Host/Interviewer
How do you think women were taught about finance? And how were you taught about finance, Jamie?
Jamie Allison Feldman
I was taught to buy things on sale. That was my education. That was my financial education mostly. You know, I think what we've learned is that, like, nobody is taught about finance, but, like, women earn less than men. Women are the caregivers. They're, you know, advertised to, to be the spenders in the family. And so when you take that and you add on top of it that none of us have a financial education, it becomes, like, really precarious. And that's, I think, part of why, you know, being women and also speaking to women, that was part of our, our goal in making this, this project.
Alison Stewart
Did you say something?
Rachel Webster
Oh, no, I just, I. Yeah, I think that also if people are talking about finance, they're not usually talking about it from this perspective, which is like, let's look at the systemics, you know, and there's in the space who were like, you know, empowered, you know, girl bust energy, and that's just not us. So we kind of wanted to, like, reach out to the women who were like, we don't feel empowered and go, okay, let's talk about that.
Jamie Allison Feldman
And because there is more than enough of that advice already out there.
Rachel Webster
Yeah.
Alison Stewart
What was a personal story of debt that you heard that kind of stays with you.
Jamie Allison Feldman
Maybe, Nikki?
Rachel Webster
Yeah. Honestly, I think it's just the trends that we've seen in our conversations with people. Like, so many people come up to us, admit it. Oh, wow, I can't believe you're talking about that. I'm in debt and I don't talk about that. So that is just, you know, super prevalent. And then when you kind of dig deeper, so many women did not really think about college as something that they would have to be paying off for the rest of their lives. And one of the women that we did speak to was talking about the balances that she, you know, things she'd taken out to try to get a degree different. And she was looking at all of the various accounts and she told us the numbers that she started with and where she. And it was like double what she even had borrowed. And that's just wrong.
Jamie Allison Feldman
Yeah. At 17, when you're making this decision and, you know, you're told that this is what you need to do to have a good life, and meanwhile, then it's not really true. Once you get out of it at this point, and then you're, you know, you have all this debt to pay off, it's like, weighing on you forever.
Alison Stewart
So this text says I was guilty of lifestyle creep, making more money to finally live on my own, but was still spending. Like, I lived with roommates. I depleted my savings, and it took a couple of years to finally admit my problem was because I live in New York City and love dinners. I did the research for the balance transfer card. FYI, you can't do it with the same financial institution. Learned that the hard way. It took me a very long time to pay down, and I was very transparent with my friends and found out that so many of my friends were living with the same situation. Did you find that out?
Jamie Allison Feldman
I feel like I wrote that text message. Yeah. It became really clear right away. I mean, I say that I was afraid my mom was going to find out. Her friends were gonna find out, my friends were gonna find out. And I had my mom's friends reaching out to me. I had my friends reaching out to me. They were so understanding. They wanted to go for walks, they wanted to have picnics. I mean, I do have an already frugal best friend, but even anyone who I'd, you know, had more of a standard, typical New York City relationship with, let's catch up and get drinks and dinner. They were like, let's get a box of wine and go to the park or sit on your couch. And ends up being, like, actually more a better way to connect than in, like, a noisy, expensive restaurant.
Rachel Webster
That just points to the culture. I mean, we're all living in these places, and in order to be part of the group, you.
Jamie Allison Feldman
You're told you have to do these things.
Rachel Webster
You do them.
Host/Interviewer
How is working on Deadheads changed the.
Alison Stewart
Way you think about your own finances?
Jamie Allison Feldman
Well.
Rachel Webster
We are going into debt, making a podcast about debt, because you kind of have to do that to make. To make anything these days. But no, I mean, I think that we're just in the same boat. We were.
Jamie Allison Feldman
Yeah. The biggest takeaway, I think, is that we're told that personal finance is personal, and we're realizing that it isn't. Finance is not as personal as I thought it was in the beginning.
Rachel Webster
Yeah. You really can't compartmentalize your financial reality with the rest of the culture and the government policies that you're living within. So we really want to explore that, and that's what we're doing for the rest of the podcast.
Host/Interviewer
Let's talk to Lorenzo from Manhattan.
Alison Stewart
Hi, Lorenzo, thanks for calling, all of it.
Caller - Lorenzo from Manhattan
Hi, thanks for taking my call. I'm a former theater kid myself, actually. Ironically, I became a financial advisor a number of years ago, which makes me a bit of a therapist, which I didn't realize I would become a bit of a therapist being a financial advisor, but it turns out that I am. And I really want to thank your guests for bringing this to light, because often people take years to tell me that they have credit card debt. And my reaction is always, oh, well, that's no big deal. That's the thing we can solve. I wish I had known. And it has become clear to me that there is a lot of societal shame in having this kind of credit card debt. And as a financial advisor, I just want to say there's no reason to. There's all kinds of reasons why you acquire that kind of high interest debt, and there's all kinds of ways to solve it. And I. So I know it's easy for me to say, hey, just don't be ashamed. Just go tell a financial advisor if you work with one, or go to your local bank and say, hey, I have high credit card debt. What can I do? But there's no reason to be ashamed of it. And I just want to thank your guests so much for bringing this to light because I'm just aware of how often people are scared to come forward with this.
Host/Interviewer
Thanks, Lorenzo.
Alison Stewart
We appreciate that.
Host/Interviewer
Let's try to get another call in here. Christina from Jersey City.
Alison Stewart
Christina, you're on the air.
Caller - Christina from Jersey City
Hi. Thanks so much for taking my call. I was just calling in to say that one of the things I was taught about money when I was younger was that it's impolite to speak about it. And I just think that that comes from people that have a lot of money, because I also have six figures of debt, mostly student loans. And it's because I was underpaid most of my life because I had no idea how much people were making. So I was living by myself in New York City as a teacher, you know, making, you know, between 30 and $50,000, and it was scraping by and, like, made, like, made you feel like I was irresponsible or somehow it was my fault. I felt extremely judged and there was so much shame attached to it. So, like, I just. Again, I. So, like most of the callers calling in, I just really appreciate your guests bringing this to light. And, yeah, we need to talk more about money. We need to encourage our kids to talk about money. We need to talk to our kids about money and what's a living wage and make them advocate for themselves.
Host/Interviewer
Thank you so much for calling in. This is really interesting. It's really touching. A nerve.
Jamie Allison Feldman
I think so. I love it.
Host/Interviewer
Okay, first of all, before we wrap up, are you Deadheads or are you just Deadheads?
Jamie Allison Feldman
A little bit of both.
Rachel Webster
Yeah. Jamie's a big Grateful Dead fan. Okay. Yeah. But we also love a pun, and I think that there's a lot of crossover with the Grateful Dead fans who are twirling their way through a cloud of smoke and sort of how we as people who are just trying to live in our economy are kind of just assuming this is the way it is and following it like it's a natural law.
Host/Interviewer
So my guests have been Jamie, Allison Feldman and Rachel Webster. They are the hosts of Debt Heads podcast. It's really, really good. Thanks for coming in.
Jamie Allison Feldman
Thank you so much.
Rachel Webster
There's more.
Host/Interviewer
All of it on the.
Nordstrom Rack Advertiser
Ready to rack to school and save Big get to your Nordstrom Rack store today for thousands of deals from just $20.
Dottie Mae Merchaum
Cause I want to look fresh. How did I not know Rack has Adidas? I got a new backpack.
Nordstrom Rack Advertiser
Score. Everyone's favorite denim sneakers, boots and activewear from Nike, Levi's, Steve Madden, madewell and Free people. Great brands, great prices. Everyone's got a reason to rack Shop Nordstrom Rack and make it the best school year ever.
WNYC Announcer
Since WNYC's first broadcast in 1924, we've been dedicated to creating the kind of content we know the world needs. Since then, New York Public Radio's rigorous journalism has gone on to win a Peabody award and a DuPont Columbia Award, among others. In addition to this award winning reporting, your sponsorship also supports inspiring storytelling and extraordinary music that is free and accessible to all. To get in touch and find out more, visit sponsorship.wnyc.org.
Podcast: All Of It (WNYC)
Host: Alison Stewart
Guests: Jamie Allison Feldman & Rachel Webster (Hosts of "Debt Heads" podcast)
Date: September 5, 2025
This episode of All Of It delves into the realities—and the pervasive shame—of living with debt in America. Alison Stewart speaks with Jamie Allison Feldman and Rachel Webster, the creators of the satirical and narrative podcast Debt Heads. The discussion centers on personal debt stories, cultural attitudes, generational shifts in financial challenges, and the stigmas imposed by both society and financial "experts." A key theme is the power of honesty, humor, and community in talking about a taboo subject—debt.
“I think I am a theater kid ultimately at heart. And so anytime I've ever done anything, it really requires, like, some sort of audience to keep me accountable.” – Jamie Allison Feldman (02:08)
“We sat and we just like I said, get out all your bank accounts. We're gonna put numbers into this budgeting app and we're gonna look at the numbers.” – Rachel Webster (02:46)
“Yikes. I'm glad you're in debt. You deserve it… How do you live this way? Geez, what a child.” — Dottie Mae Merchaum, portraying internet trolls (06:29)
John from Monmouth County – Questions mortgage strategies; hosts reaffirm they’re not financial experts but share common advice (11:12).
Lorenzo from Manhattan – Financial advisor and former theater kid highlights the years it often takes for clients to reveal their debt, and the importance of eliminating shame (17:10):
“As a financial advisor, I just want to say there's no reason to [be ashamed].”
Christina from Jersey City – Explains how silence about salaries led to lifelong under-earning and student debt, reinforcing need to normalize money conversations for future generations:
“It’s impolite to speak about it… I have six figures of debt mostly student loans… I felt extremely judged and there was so much shame attached to it.” (18:24)
“But we also love a pun...there’s a lot of crossover with the Grateful Dead fans who are twirling their way through a cloud of smoke and...how we as people who are just trying to live in our economy are kind of just assuming this is the way it is...” – Rachel Webster (19:37)
On Shame:
“Please drop the shame. That’s the most important thing. And really start to talk to people in your life because that’s the first step.” — Rachel Webster (08:07)
On Advice:
“But please do not come to us for financial advice because we are not experts.” — Rachel Webster (11:18)
On Generational Divide:
“We’re still following the dream of the boomers...and yet there has been so many things that have changed how that can be possible for so many people.” — Rachel Webster (11:55)
On Community:
“I had my mom’s friends reaching out to me. I had my friends reaching out to me. They were so understanding. They wanted to go for walks, they wanted to have picnics…It ends up being, like, actually more a better way to connect than in, like, a noisy, expensive restaurant.” — Jamie Allison Feldman (15:30)
On Personal Finance:
“We’re told that personal finance is personal, and we’re realizing that it isn’t. Finance is not as personal as I thought it was in the beginning.” — Jamie Allison Feldman (16:40)
For more on debt, shame, and fighting back with humor, check out the Debt Heads podcast by Jamie Allison Feldman and Rachel Webster.