Jamie Feldman and Rachel Webster

Jamie Feldman is a writer & producer who accidentally became a TikToker after being laid off from her longtime job at Huffpost in 2021. Before talking to the internet about debt and money, she overshared about basically everything else – both in real life and online.  

Rachel Webster is a writer, documentary director, and multidisciplinary story editor known for her contributions to eclectic genre-busting film and video projects. She lives in Brooklyn with her husband and two kids, who Jamie helped raise.

They make Debt Heads, one of my favorite shows. Sign up for the newwwwsletter. Do it!!!

Describe Debt Heads in 10 words or less.
True crime investigation into the murder of our bank accounts.

You will like Debt Heads if you like…
having fun / sticking it to the man / $5 margaritas / dancing in the street / bottled and boxed wine / silliness / true crime without the murders / sarcasm / crying till you laugh / laughing til you cry / strong opinions, loosely held

How’d  you two get connected?
Rachel needed a babysitter. Jamie needed a job. We fell in love, the rest is history.

How are you two different and how are you the same?
RW: We probably share a brain. We have the exact same sense of humor and politics. We like to eat the same food and drink the same drinks. We think life is pointless without humor, community, equity, empathy, time spent in nature, and being surrounded by (too much) food and wine. We also love to write.

JF: Our differences have helped us grow as friends and creative partners. Rachel is definitely more of a self-starter than I am, and she has helped me take myself and my work more seriously. I on the other hand am more comfortable self-promoting and schmoozing, which has pushed Rachel out of her comfort zone. She would never have considered being public facing two years ago. I forced her into the spotlight. 

What inspired the sound and style of this show?
RW: I am a film editor so the style of Debt Heads is entirely influenced by my work in film. I have been working at the intersection of documentary, narrative, music video and comedy for 20 years. The show’s tone comes from that, and of course our actual friendship dynamic and combined sense of humor and rhythm.

Jamie…why were you (and so many other people) so comfortable sharing, like, everything about yourself online but were hesitant to talk about your own friend about money?
Let me consult my therapist! There is a disconnect between what I logically knew, which is that credit card debt is pervasive in the US, and what I felt, which is that I had failed at money. Money is one of those things we’re just supposed to know. Unfortunately in our culture, it also represents our feelings of safety and security. And I had deep wounds and fears around my sense of safety, and shame around my money ignorance. I was so disconnected from the origins of this shame and fear, that I could compartmentalize my dysfunctional relationship with money and continue to be delusionally confident in every other way. 

What was the eureka! moment where you were like, oh this is a podcast?
JF: We joke that Rachel has slowly radicalized me over the years, but the truth is that she has been thinking about our dysfunctional economy for much longer than I have. I didn’t mean to become a debt “influencer”, but once I started getting some attention for talking about it publicly,  a few people suggested that I think about making a personal finance podcast. At that point I’d been making videos and putting myself in front of the camera for a long time, but I knew I had no business offering personal finance advice – and I didn’t want to. 

RW: I’m really grateful to the people who suggested Jamie make a podcast, because it’s what got me to imagine how something like Debt Heads could work. It was definitely a eureka moment when I thought: Instead of talking about personal finance, we can make a podcast investigating why there is a thing called personal finance in the first place, because I don’t believe finance is personal. I could hear what it would sound like immediately and then we launched into a brainstorm. We have the original sketches of the idea on our studio wall from that very first day, and they are still very much our thesis. 

How is the show different than you thought it’d be when you started?
At first, we thought we’d pitch the idea to somebody who would take it and run. We made a trailer and a TWENTY SEVEN page deck. LOL. God bless anyone who even looked at that thing. 

But the tone and writing and thesis has been there from the beginning. The entire process has just been a lot longer with more stops and starts and surprises than we thought it would be. In hindsight, DUH!

What’s something you learned about yourself making it?
JF: This has been years in the making, but I have really learned to take myself and my work seriously. I spent many years not really believing that my work was worth committing to. I did not believe that staying home to write was enough of a reason to decline a social engagement (hence my debt) and I was surrounded by people who reinforced that feeling. I am much more committed to getting it right now and believing that I’m worth investing time and effort in.

RW: Putting myself out there was not as scary as I thought. The world needs us to be brave and share our ideas. I’ve always known that we are stronger together, but actually putting that idea into the world has made me feel stronger than I ever imagined. 

If I gave you $500 right now what would you do with it and how is the answer to that question different than it would have been if I asked you before you made the podcast?
We would probably use it to submit our show for a few of the pricey podcast award opportunities that we didn’t realize cost money 🙃

What’s a podcast you love that everyone knows about?
RW: The Butterfly Effect - Pure genius. Unforgettable. Jon Ronson writes stories about the economy without trying to write stories about the economy. That’s what makes them so effective. (He makes a cameo in Debt Heads!) 

JF: Heavyweight, Working It Out with Mike Birbiglia, This is Uncomfortable 

RW: There Goes the Neighborhood Season One. As a New Yorker, I think about details from that show all of the time. I also love Lena Dunham’s Women of the Hour and The C-Word.

If you had 100K to spend on the show, how would you spend it?
When we were pitching our pilot, everyone told us that our podcast was really good, but the subject was too boring and depressing, and the style was too expensive. But we’ve made this whole thing work with just the two of us working nights and weekends, and during long stretches of unemployment. Our $20k grant paid for materials and contractors. If we got $100k we’d consider paying ourselves for the first time, but … we’d probably just use it to make more ideas come to fruition.

Thanks, Jamie and Rachel!