Bestcasts asks podcasters to discuss the three most memorable episodes of their podcast. Ties are allowed/encouraged. For more podcast coverage, see Podmass, The A.V. Club’s weekly roundup of the best ’casts out there.

The podcaster: Anna Sale has always been a storyteller. As a former political reporter, she interviewed voters on the 2012 campaign trail about policy issues that affected their everyday lives and heard stories about family, work, and stability. To her, it became the most interesting part of her job. So when a contest opened up at WNYC to pitch a new show, where she was working as a writer, she took the weekend to think about what her dream job would be. It involved spending more time with these stories focusing on what she describes as “real things we struggle with alone.”

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She wrote up the idea with a bold name that described these main issues: Death, Sex & Money, and pitched it. She won the contest, produced a pilot episode, and since then, she and her team have released new episodes every other Wednesday. The show has garnered a huge online community, and listeners from all over the world relate and respond to interviews with people she talks with, whether they’re famous or not. The A.V. Club talked with Sale about her favorite episodes of the show so far.

Death, Sex & Money: “In New Orleans: Big Freedia Bounces Back”

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The A.V. Club: While you were in New Orleans, you interviewed a lot of different people who were in the city when Hurricane Katrina hit. What struck you about spending time with Big Freedia and walking around in the neighborhood she lived in?

Anna Sale: I loved this one. I interviewed her on the block she lived in when Katrina hit and we started the interview in front of where the duplex had been and hadn’t been rebuilt yet, 10 years later. I got off the plane with my producer and editor and we drove down to the neighborhood. It was so hot and, of course, none of us were prepared. Big Freedia had a little towel in her back pocket to wipe her brow and I was just sweating and not used to the humidity. [Laughs.] It was an incredible image of standing in front of this empty lot with Big Freedia who has the outfit, the nails, the cool sneakers, totally done up, and talking to her about her life.

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When Big Freedia was growing up, her name was Freddie. Freddie came out very young in a predominantly African-American neighborhood, and the other gay kids she knew didn’t feel comfortable coming out. So hearing that story was like, what was going on that made Big Freedia felt comfortable owning her identity at a young age? Hearing about how she was shot by someone who approached her car and shot her through the car window, hearing about bounce music, and talking to her about her mom, who had an incredible role in her life.

The moment I most remember was a perfect radio moment, was after sweating and sweating, we move to a friendly neighbor’s porch, and I’m in the middle of asking when she came out to her mom, and she describes her mom sitting on her lap. I asked whether she meant she was sitting on her mom’s lap. She said, ”Not me, I’d have broke her!” And there was a crack from the porch swing, and Freedia was like, ”Oh god, I almost tore the swing down!” [Laughs.] It was so funny, it was as if the house was listening to our conversation. We did this intimate interview about her family, she gave us suggestions where to get the best food, and drove off. It was the perfect welcome to New Orleans.

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AVC: How did this series come about? Is it something you want to do more of?

AS: We were curious about what would happen if we did the Death, Sex & Money version of the story covering what everyone else was covering. The 10-year anniversary was coming up, so we worked with a great producer in New Orleans and asked if you were to pick characters from around town, who would you talk to? It was really key and she introduced me to Terri Coleman, who was in another of my favorite episodes. Many media moments felt like they had to have a thesis, like New Orleans is back, New Orleans is still struggling, here is a grand theory of Katrina.

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Focusing on personal stories, you don’t have to do that, which I think allows you to be more nuanced and honest. At the end, here are five really different people who tell their moment when Katrina hit, and it’s such a profound trauma that ten years later we can ask them to tell their stories and the same tears well up, the same sense of mourning of what happened to their city, and we hear all the different ways their lives spun out since. It gave the stories a sense of place. None of us are from New Orleans and that we were allowed in, that people entrusted us with their stories… it felt really special given the some of the feelings about media that remained 10 years after the storm.

Death, Sex & Money: “The Sex Worker Next Door”

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AVC: Emma responded to an episode called “Cheating Happens,”and you checked in with her as time went on, talking over the phone and email. At times she sounds hesitant, asking to retract some parts of her story and tell others. How did you handle the process of telling her story?

AS: I think it speaks to the relationship that I had with listeners that I didn’t fully anticipate but the thing I think is most precious about the show.

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We put out a show called “Cheating Happens” last spring, and within a week or so, I got this email from this woman who said, ”Here’s my point of view about infidelity as a sex worker and what I hear from my clients.” She was matter of fact that her clients are primarily married men who weren’t fulfilled in their marriages. She was straightforward, quite comfortable with her work, and explained why she did it. It provided her the flexibility and financial stability she needed in her life, and she was unapologetic about doing sex work.

I emailed back and asked her if she wanted to talk because I found it interesting to learn what is the process, what happens on the day I’m going to try this out? What does it feel like to learn how to be a sex worker and what are the consequences in your personal life? We set up an interview. Because she’s doing work that could get her in trouble legally, we agreed to not use her real name. I think we were both surprised when we recorded—as it went on, there were parts of her work that she was clearly uncomfortable with that weren’t easy and that were emotionally exhausting her. The next day, she wrote me an email and said, “I have all these feelings about the interview and I need to take a break.” Having that conversation prompted a major reevaluation of her work. I said, ”Don’t worry about the interview, do what you need to do.” We talked later on in the summer, and she agreed to do another interview after taking time off.

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What I liked about that episode was it captured her ambivalence about her work. In the end, she’s going to continue being a sex worker, she feels like it’s what she needs to do to earn money she needs but that doesn’t mean there aren’t downsides to it. It was a complicated look at what it is to be involved in sex work. It was emotional for her and it was also trying to balance making sure we’re capturing a compelling story while recognizing she’s in the middle of something.

AVC: Have you kept in touch with Emma since?

AS: We were definitely in touch afterward. This happens with some other episodes: We got emails from listeners who asked us to please pass this on to Emma, which is not her real name, and it started a conversation with Emma and our other listeners that I wasn’t in the middle of, which I think is cool. Sex work and whether it should be legalized or not was an ongoing conversation in response to the episode, and whether it was a fair portrayal of sex workers because we were showing someone who has mixed feelings about the work.

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AVC: A couple of times during your conversation with Emma, you ask about her savings and if she has a number where she would quit. That was something that really stood out, especially after she talks about how draining the work is—like, if this work drains you and you’re doing it for the money, and you have money saved, what place do you think you can be in to feel safe enough to stop? What were your feelings about that question?

AS: At least how I think about money, it can be a generalized sense of insecurity of “I don’t have enough” and it’s scary. We all make compromises not to feel that. She seemed very aware of the tradeoffs she was making to feel financially secure. What I thought was interesting was that question revealed is this isn’t just a certain amount of money I need in my savings account—I know I need to have retirement savings, I know I need to have a certain amount to support my family. This isn’t someone who is running down her checking account, she was trying to live a financially responsible life and getting paid for sex work was part of it.

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Death, Sex & Money: “Autism Isn’t What I Signed Up For”

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AVC: What was particularly memorable about this episode and what you remember from talking to Diane?

AS: That sticks out because it also started from hearing from a listener. We posted an article on our Facebook page about trying to decide whether or not to have kids. Diane commented and said something to the effect of, “I have two children with autism and if I had known how challenging it would be, I wouldn’t have had kids.” To see someone saying that publicly with their name attached was jarring. We asked her if she wanted to talk about her family and what it’s like to be the mom to her two boys.

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I really liked that episode because I feel like it was a mother speaking really honestly about how hard it is to take care of her family. Certainly her experiences are particularly challenging because her boys both have severe challenges, but it is so uncommon to hear women and mothers articulating the costs and tradeoffs of what it is to be a parent. To hear her say both I love my boys and they deserve a mother who loves them and take care of them and this isn’t the life I wanted for myself—it’s hard for listeners to hold those things together, but at the same time but it’s really real. A lot of us have feelings about things in our life that are complete contradictions but both true.

I liked that she talked about trying to find community in church and that she found going to church disempowering was something you don’t hear a lot. It was memorable doing the interview and also memorable hearing responses from listeners. We heard from people who are on the autism spectrum, who were extremely upset by the episode, [saying they felt] like caregivers to people on the autism spectrum too often speak for [them]. We heard from families with family members with disabilities who felt relief to hear someone articulate the real challenges and didn’t gloss over them. Our Facebook page was filled with people with strong opinions who were mostly talking with each other and not yelling at each other.

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AVC: There was so much listener feedback for this episode. How did your team handle that? Does it naturally occur where people end up talking to each other?

AS: Ha, I don’t know! It’s something we want to cultivate more of, and have a sense of community to the show that is not just mediated by me. It’s cool to see it when it happens. It’s also a testament how people respond when they hear someone talk openly and with vulnerability. I think it triggers our empathy and might be why there’s a humanness to the responses to our show. Not always, but for the most part. So, I didn’t expect the kind of conversation with audience to be as robust as it is. It’s something that’s been a total surprise and we’ve had very broad open questions about personal things that people will mail in from around the world and share with each other.

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