Dylan Tupper Rupert: Listening keeps the conversation going
A conversation with the podcaster
Welcome to Human Pursuits, the column that features need-to-know names and stories in media and other creative spaces. Today, podcaster Dylan Tupper Rupert on her new series, Music Person, willing things into existence, lessons learned from Yasi Salek, and more.
For an art form that inspires endless hours of online discussion, there is a surprising lack of podcasts covering music.
Sure, there are old chestnuts like All Songs Considered, Song Exploder, and Switched on Pop. But, barring a few exceptions ( from Bandsplain, Rob Harvilla from 60 Songs That Explain the '90s), most of the personalities associated with music analysis and recommendation in 2025 have a background in video. They specialize in eye-popping thumbnails and punchy clips. They have strips of LED lighting and a monthly subscription to Adobe Premiere.
Dylan Tupper Rupert hopes to avoid all that.
Her new interview podcast, Music Person, offers a human-centric look at Chunes and the people who create them. Like this newsletter, the conversations are often meandering and emotive, exploring much more than royalty splits and pre-amp settings. Dylan wants to understand the “why” and “how” driving modern creatives, and, having binged several episodes over the holiday weekend, I am fully along for the ride.
As a fan of her work dating back to Bandsplain, I was excited to see this new project hit my feed. Initial guests include Karly Hartzman of Wednesday, Indigo De Souza, and Molly Burch.
And so, we had much to discuss.
Our edited and condensed conversation touched on Dylan’s early days in Seattle’s DIY music scene, the pain and pleasure of planning your own festival, willing your dream job into existence, her preferred BBQ rubs, and more.
ES: So I absolutely love Music Person. To paraphrase a wise woman, it’s a goddamn, beautiful podcast, babe.
DTR: Laughs. Wow. That’s the highest praise you can get in the music podcasting sphere.
ES: Not to throw your own question back at you, but I’ve noticed you like to ask your guests, “Where are you at with everything right now?” So, where are you at with Music Person? How do you feel it’s going?
DTR: What a day to ask. I just returned from a trip to upstate New York. I was interviewing some people while I was there, and I was hanging on by a thread. If I hadn’t known I was coming home yesterday, I probably would’ve fallen apart. But I’m really excited about this show, and grateful for the legs it seems to have. All of these conversations between me and my friends and peers, and other music people, are starting to broadcast out, and I’m getting a lot of good feedback from that
In terms of the logistics of my day-to-day life, things are batshit crazy. I’m spread incredibly thin. I’m under-resourced and understaffed, but full of love. Laughs. Next month, I’m hosting two Dylanfests, which are these all-day summer shows I put on in collaboration with some restaurant friends. It’s a food-wine-music thing, and it’s so fucking fun, but I feel a little overwhelmed. My life looks like a million tiny little scraps and pieces and details of things, and then each scrap and detail has five different people who want to know something about it, and I’m the master of the collage. So it’s a little crazy, but good.
ES: One of those Dylanfests is in Washington State this year, right?
DTR: Yeah, that’s the flagship one, though it’s only like the second year I’ve done it.
ES: Did I see it was on the San Juan Islands?
DTR: Yes, it’s on Orcas Island, which is one of the most beautiful places you can go in the Northwest. I got acquainted with a chef up there named Jay Blackinton, who owns this restaurant, Houlme. We kind of grew up in the same Seattle DIY scene. We narrowly missed each other… He’s a truly special person. His buddy, who is an EMT or a firefighter or something, has a big property, and so we camp there and then do a show at the restaurant. It’s fucking perfect and dreamy. The only problem is that the ferries to get from the mainland to the islands are such a pain in the ass. Every year, I think, “Oh, God.” But then everyone’s there, I'm like, “Oh, it’s all okay!”
ES: I’ve listened to the first three episodes of your podcast. How did this project come about?
DTR: I was contacted by [Friend of the Newsletter] Ian Wheeler, who is the head of Talkhouse and a tastemaker in his own right. It was the end of 2024, and I had finished the latest season of my previous project, Lost Notes, which was about the female groupies of the Sunset script scene in the sixties and seventies, and a “feminist relensing” of that story. I co-created, hosted, and wrote that series, and it was something I always wanted to do. Ian reached out on the heels of that and said he loved the show, and that they’d heard me on other podcasts. He asked, “Do you want to do anything?” At first, I thought he meant music documentaries, which I love making, but are highly intensive. The budget for that sort of podcast is in disalignment with the current economic realities of the industry.
I told him I’ve always wanted to make a show like Music Person; something that could be the weekly Fresh Air of indie rock. There are a lot of great podcasts out there, and a lot of shitty podcasts out there, but I noticed there wasn’t one with a destination-music-profile-interview format. I thought, “That’s weird.” I had pitched this idea to other networks before, and no one was all that excited about it. When Ian hit me up, I told him, “This is what I want to do, if I’m being completely honest.” He was like, “Okay, cool.” No notes, just go.
ES: It really can be that easy, hey?
DTR: Laughs. I never experienced that before.
ES: How much of your life has been the result of you simply willing things into existence?
DTR: Good question… I feel like my life has had three phases so far. The first was when I was very young and in the Seattle music scene. Everything was in my backyard. All I had to do was go out and get what I wanted and figure it out; meet one person who would introduce me to another person, until suddenly I’m working at a venue, or making flyers for shows. Growing up like that was so lucky. A lot of the stuff I did was sort of provided for me in this fortunate way. But I also had a lot of energy and gumption to go connect those dots.
For many years, after I first moved to L.A., I felt it was time to try and professionalize and get a job; be in the media. I thought it would require me to put away my natural impulse to start projects and collaborate with other people. I couldn’t quite figure out how to link the drive that inspired me to do things on my own with what you need to do to survive. Not that I’ve figured that out.
This final iteration has emerged in the past few months. I turned 30 and I got laid off. I wasn’t working at Bandsplain anymore, and thought, “It’s now or never. Do all the things that you don't wanna die saying you didn’t try to do.” I'm a little bit in that mode.
So to answer your questions, it’s definitely part of my personality, but particularly in the last three years, I’ve been willing things into existence. I would love for one of those things to be income.
ES: Would you say that driving force comes from your time in Seattle’s DIY scene?
DTR: A lot of my mindset, but also my baggage, comes from DIY. It comes from growing up in a scene where youth were a big part of it. Places like The Vera Project, which is a nonprofit all-ages venue where I worked. I was just talking about this with my friend Jenn Pelly, who’s a music writer. We were just on that trip together in upstate New York, and I mentioned how I knew that job was totally unique at the time… By the time I was 13, I was taking tickets at shows and stocking the green room and eventually I was on committees that decided programming and dealt with fiscal sponsorship. I still have a ton of friends from that period, and a common thing we talk about is how we were included in sharing responsibility. It’s that sentiment of “It’s not DIY, it’s doing it with a bunch of other people.” That was super formative.
In the last three years, I’ve been willing things into existence. I would love for one of those things to be income.
But I also think I have professional ambition, too. I felt at odds with those two instincts at various points in my life. Now it feels like they’re syncing up in a way that I hope is sustainable.
ES: What is your ambition for Music Person? Are you trying to win a Webby? Buy a house? Laughs.
DTR: If we’re manifesting, I would love to buy a house. I have a list written down of things I want when I’m making real money again. I want to get one of those personal trainers who focus on mobility and prehab. Laughs.
But no, I want this to be my full-time gig. I think there’s a missing piece in the music journalism landscape that I'm hungry for as a consumer. This project is very much me, and my voice, but there’s a feeling right now that people are missing blogs and music magazines, and I’ve always been curious about solving that puzzle in podcast format… There are music podcasts out there, but the field feels small. I’m friends with everyone who’s making a good music podcast right now, you know? I want this to be a weekly destination for people to engage more deeply in music and discover new music, and think about creativity.
ES: I think we share a similar sensibility, in that we care about the people behind the output. Like, you’re not asking questions about beats per minute or musical scales.
DTR: I have a bit of a human interest lens on music journalism, if that makes sense. I’m most interested in questions like, “What sort of person is behind this? What sort of life does this art come from? And what does art generate for you?” I also think a lot about strategy in storytelling and interviewing.
They’re obvious, humiliating examples to bring up because they're so mainstream and famous, but I think a lot about Terry Gross from Fresh Air, and how that program is a stalwart institution, where the audience can spend an hour of slow-but-steady time with a person or an idea. And it’s the same with Anthony Bourdain. You’re getting a taste of a place and some context, but really, you’re getting to know the lives that people are leading by speaking with them and experiencing, just for a moment, how they live or how culture integrates into their lives. Those are the things that I orient my intentions around, and why I’m committed to this being an hour-long, three-act, old-school radio interview, because I find that format very comforting. I always have, but particularly in the era of short-form video. There are a lot of really fucking awesome video interviewers, but that’s not what I’m interested in doing.
ES: I wanted to ask about your approach to interviewing because you have a very relaxed nature about you, to the point where the conversation seems almost unplanned. How much preparation are you doing ahead of time?
DTR: I try to set specific intentions around preparation, and I get upset with myself if I don’t check all these boxes because, at this point, I’m my own boss. I can do whatever the fuck I want, no one gives me notes, and so if I’m rushing or cutting corners, I don’t have anyone to blame but myself.
If I’m in my happy place and interviewing someone whose record is coming out in the future, for instance, I want to walk my dog for an hour, listen to the advance of that record, and be away from the computer. Then I like to read old press that they’ve done and get a sense of what they’ve already discussed, and what to avoid, or synthesize in the episode’s intro.
I like to spend a day sort of immersing myself in what someone's already done. I usually have a set of more personal, esoteric questions that I’m curious about, and then concrete questions that I ask in different ways to different people… But sometimes I’ll phone a friend who knows the person, or ask their publicist for insights and topics they haven’t talked about yet.
And then, during the interview, I’ll have paper with questions written down in front of me. At this point in the show, I’m adamant about only doing in-person interviews. No Zoom calls. I put everything in a notebook, which I think allows me to be way more present during the conversation.
People are missing blogs and music magazines, and I’ve always been curious about solving that puzzle in podcast format
ES: What distinguishes a good conversation from a bad conversation in your mind?
DTR: Listening – on both ends of the conversation - is how you keep a good conversation or a good interview going. You prepare so that you have a good understanding of who someone is and what they’re about. That allows you to be a bit more freewheeling, but it also still requires listening. I can riff forever, but if I’m listening, I don't. Laughs.
ES: How did you come into the production side of things? Did you go to school for audio excellence or just stumble into this?
DTR: Not at all. I have an editor. I’ve never cut tape. I honestly refuse to at my job. I came through the back door when I was working for Yasi at Spotify. I was Senior Creative Producer. It was an era where people could have media titles with a tech salary. Like, it was a producer role, but it was creative production. My role was more like that of a magazine editor as opposed to something more technical, like a copy editor.
ES: Speaking of Bandsplain, what is a lesson you learned from Yasi that has stuck with you, or that you’re bringing into this experience?
DTR: This is so funny, because I’ve thought about this question before. We were speaking earlier about willing things into existence. Yasi is spectacular at that. She brought me into the development and the launch processes, and watching her navigate that big company in order to create what she wanted was totally permission-giving. It was a big lesson for me on how to lead my own project instead of waiting around for other people.
The most specific thing she showed me, and it was honestly amazing to see, was how to navigate conversations with superiors, and sort of dom them into giving her what she wants. There are so many cool things that we did that were the result of her having the savvy to convince people, or do it and ask for forgiveness later. I hate to say it in these terms, but I think she’s very entrepreneurial. She’s operating within a huge corporation and was able to get something really cool out of it.
ES: People will sometimes ask, “What’s the last album or song that made you cry?” but the first episode of Music Person made me surprisingly emotional. What’s the last podcast that made you cry?
DTR: Honestly, I don’t listen to a ton of podcasts.
ES: Must be nice.
DTR: There are 5 or 6 that I rotate… But one does come to mind. Rob Harvilla’s 60 Songs That Explain The 90s: The 2000s did an episode about Amy Winehouse that floored me. It was so good. It totally made me cry. I was making pancakes at 2 o’clock in the afternoon. I was having a really slow day, and it was like “Oh, fucking God.”
ES: You're from the Pacific Northwest, but you have roots in Kansas City. I wanted to ask you, what’s your BBQ rub recipe? Like, what are Dylan’s ribs tasting like?
DTR: I have three specific rubs that I make and keep on hand at all times. One is my standard Kansas City rub, which is adapted from the Gates Bar-B-Q recipe. It’s your classic brown sugar, smoked paprika, and a bunch of other shit.
My second rub is a Pastrami rub. I had a legendary “Pastrami party” in 2023 where I cured my own Pastrami for two weeks, and then smoked it. I was so excited that I accidentally invited too many people over. I had 8 pounds of brisket, but I invited 45 people, and didn’t have enough to feed them all. So I ran to the store, and I got a bunch of salmon fillets, and I smoked them with Pastrami, and I realized that rub is good on fucking everything. It was the best thing I’ve ever cooked in my life.
And then my third rub is this coffee chili rub that I adapted from a New York Times recipe. It’s absolutely insane on pork chops. Absolutely insane. Once I get this music thing out of my system, I'm going full-on barbecue YouTuber.
ES: The fact that you own a smoker is impressive.
DTR: Thank you. I got it on a massive sale, and it was a consolation prize after being evicted by an evil landlord.
is a podcaster. She lives in Los Angeles.