Dan Drago's 200th Episode of the 25 O'Clock Podcast Is a Lesson In Getting It Right
Dan Drago, photo courtesy of the artist
By Emily Herbein
Dan Drago’s 200th episode of the 25 O’Clock podcast features WXPN’s Helen Leicht, and there’s a high chance that one — if not a handful — of your friends and favorite musicians were guests on the show over the last year. Drago put out more episodes than ever thanks to the pandemic’s downtime and combatted burnout with a stronger work ethic (something that we talked about in my episode). His conversation with Helen dives through her decades-long career in music and radio, her experiences with some of the world’s biggest artists, and she offers some hard-hitting advice for those hoping to make an impact in a field that they love.
Dan and I talked last week about the heart behind the show, and why after seven years he still feels so attached to this project. It’s Philly’s longest-running music podcast for a reason, and I remember feeling hugely accomplished when I was contacted about appearing in an episode. Drago is likely the most connected guy in Philly music, and earning a slot among the ranks of so many of my own favorite artists felt like a major win. We go all the way back to the beginning and recount his first guest, the way his process has changed over the last year, why he chose Helen Leicht as his milestone guest, and where he hopes to go next.
You can stream 25 O’Clock on Apple Music as well as the official website, and keep up with their socials on Instagram, Twitter, and Facebook.
Emily: Why did you start the 25 O'Clock Podcast in the first place? And did you ever expect it to become this long-standing popular project in Philly?
Dan: I was in bands for years and years and years, and I moved to the city around 1993-94, and it was a very different place there at the time, but it was still cool and there were places to play. There was more here than where I came from, which was western New York in the Buffalo/Rochester area. And, you know, the things that you do in your band — you meet people, you play shows, you bang your head against the wall for multiple years — I did all the cliche "band guy" stuff. I worked crappy jobs so I could go on the road, but then in 2013 I was just done. I left the band that I was in, The Way Home, and I felt like the first time in my life — like for the first time since I was a teenager — I wasn't in a band anymore. And like, that's almost like getting divorced or something. You just look around like, "What do I do now?" Like, the whole x number of years were all hinged on this thing and I don't do that anymore. So I kicked around, I did some production to help people make records. I was part of a DIY live series at the Fletcher Memorial in Bellavista, which was a lot of fun. I met a lot of my earlier guests there because I was the showrunner. But in the back of my head this whole time, I thought to myself, "I could start a podcast, I guess." Podcasts were still an overcrowded marketplace in 2014. So I thought, "What if I just started talking to bands and people that I know and just keep it low-key." One thing led to another, and the next thing I knew, I was talking to more and more people and people were reaching out to me, which is cool because, in the beginning, I was finding anyone who was on the show. And then small labels or publicists started reaching out to me from bands. And that's how I knew I was probably on to something. In the beginning, I had no idea what people would think of this. I wasn't thinking about that in the beginning, either. I was just thinking, "Can I do this? Can I hit a production schedule? Is it worth people's time?"
Emily: How did you choose your first guest? Do you remember?
Dan: My first guest has absolutely nothing to do with Philadelphia music. And this is by no means a dig at him, but he was my trial run. He's this actor I'd known for many, many years named Dennis Hurley. He's in comedy and had done a whole bunch of interesting viral videos that had taken off, like with Funny or Die and things like that. And I'd known him for years just as a guy. A friend of ours was getting married and he was in town, so I was just like, "Why don't you come over and we'll just do this?" My second guest was Steve Harner of Bridgeset Sounds, the music store on South Street. That made a lot more sense. At first, I didn't know if it was going to be like a fully Philly music thing. I just knew that I have creative friends and I'll talk to anyone. Musicians, writers, filmmakers. Turned out in the end, I knew mostly musicians. I think you're the first person to ask me who my first guest was.
Emily: Every project needs a trial run. If you look back through Philly Live's archives, it's like my college campus bands and my friends and I remember kind of feeling out how it was going to go. Did you ever hit a point when you're looking for people to interview specifically within Philly and feel like you've talked to everyone and you don't know who to ask next?
Dan: You never run out in this town, you will never run out of guests if you keep your ears open and you continue to engage with the community. We've talked about this before — there's a whole apparatus around the scene that supports it who are just as interesting, or sometimes a little more interesting than musicians because — and not to knock a musician — but the story of musicians is kind of the same. They get up, they go write songs, they perform, and they want people to hear their records and they want people to see them. And that's what drives them. But you know what drives someone to open a music store? What drives someone to run the social media of the local radio station? When talking to someone like, in the case with my 200th episode with Helen Leicht, it's like, where did you come from? What was your trajectory? She's worked in radio for forty, forty-five years and radio has changed so much from the late 70s when she got involved to now and that's fascinating.
Emily: Finding people who make it their job to put someone else's passion project in front of you — why do they find that so fulfilling? I think that's so interesting. I started this other series on Philly Live, called The 30% which follows women in Philly music who are managers or photographers, anyone who's behind the scenes in some way and like, half the time they can't even play an instrument, but they're so passionate about other people's music. People who make it a goal to make other people's dreams happen are so selfless and interesting to me. So I love those conversations, too, and those people are everywhere. You just have to know how to find them.
Dan: There are always new people, and there are always people I don't know in different scenes who play in different styles that I might not know about, but I guarantee you I know someone who does. I rely very highly on the recommendations of other people in the music community. Those are the best recommendations I get, and I try and stay up on that. I mean, it's been hard for the last year for any of us to do any of that, but the fact that you and I were able to get anything done this year — in fact, you and I got more done this year than we have in the previous years — I think that's amazing. And the community was absolutely willing to work with us and try something unconventional like all these chats on Zoom.
Emily: How did you learn to reframe your process through quarantine? Because I think anyone can learn how to how to host a Zoom meeting. But I feel like with what you do, you're so great at facilitating conversations and doing the research on people. But how did you navigate figuring out this new way to work on this project and work through burnout and find a new sense of motivation?
Dan: I'll tell you my first thought when I was transitioning over to Zoom, which is my thought on starting most things. And that's, "Well, this isn't going to work."
Emily: I'm the same.
Dan: Exactly. And in the end, I'm fine. I thrash around and then in the end everything's fine. So when I first sat down to see what this would look like, I did have a few shows in the can from February and early March that I could play out for a little bit. When it became more clear that we're stuck like this indefinitely, I had to think long and hard about how to still have an engaging conversation while not being in person. In the beginning, it was actually easier because we weren't burned out from Zooming all the time and a lot of artists were just so incredibly happy to talk to each other. I did an interview with Katie Feeney from You Do You, and she was one of my first ones over Zoom. It started the tradition of what would happen, especially in those first few months, that after we'd finish the conversation, we would stay on for like another forty-five minutes and just chat.
Emily: How do you prep for your interviews? What what goes into your research with a guest, whether you reach out to them or they've approached you? How do you "do your homework" before the conversation"
Dan: I did all the same prep for Helen that I do for anybody. But what was different with her is that because she has all of this experience, I wanted to give her the questions in advance. But I start every single sheet with the same question, which is "Where are they from/early experiences with music?" It doesn't matter if they're a musician or not because everyone has early experiences with music, and that's what I want to know. That's the part that I want to get at because that will inform the rest of the conversation right there. I had Isabelle Fuhrman on, and when I asked her about growing up, she said, "Oh, all my family's musical. My mom and dad were in the rhythm section of a Grateful Dead tribute band." And I was just like, "Okay, we've got to talk about that," and then boom, you're off. And that's stuff I can't plan for. Even if people send me bios and press material ahead of time, even the best publicist and the best press release, you're not going to think of everything. And I want to get off that press sheet.
Emily: I kind of can vouch for both sides because as a journalist, I want to ask the questions that the publicist isn't thinking of and that people haven't seen before. But then as the publicist, I can vouch for the hours writing the perfect press release. So I'm like, "Of course I want you to use it." But then again, I'm like, "Please don't just use it. This isn't all the good stuff."
Dan: Some people just don't have a lot out about them. Some people don't have publicists, some people don't have websites with a bio or the bio is very, very brief and it's more like an artist statement. If that's the case, I'll sometimes ask peers questions about them. The first time I interviewed John Coleman, I didn't know much about him, other than that he was an uproariously great dude to hang out with, but I didn't know much about him other than he can kill the bass. He's in this band with my friend Ross, so I called Ross and I was just like, "Hey, I'm doing this interview in an hour. What should I ask him?" So Ross told me, "Ask him about the time he was a lunch lady." And I was just like, "What???" He goes, "Oh yeah." And so that got us into this whole topic of all these jobs that, you know, all these like day jobs that John had while he was living in Pittsburgh and playing in jam bands. He drove a bus for a Jewish day school, he worked as a "lunch lady man." And he got into a whole thing about how that's how he got kids to like music, because they'd talk in the cafeteria. He said he had "Funk Fridays" and he would just play, you know, big funky Jon Coleman music in the lunchroom. I never would have known to ask about that.
Emily: I think that's genius. I love when I get interviewed because it's infrequent, and people typically ask me music-based questions only, but if you ask my roommate what you should talk to me about, you would have a drastically different conversation. It would be hilarious.
Dan: We talked about cats when you and I talked.
Emily: That's a huge part of my personality. But it totally pays to do the research. I try to not read interviews or reviews of things if I'm going to do a higher-profile interview with someone as well, because I want to make sure that I'm also not a little bit biased from what the other person wrote,
Dan: And if the music available out there, I'll go as far back as I can to see the progress of an artist to see how they progressed from their first, early demo EP to a record that they did at the Headroom. I love talking about that process. That's happened to me as a songwriter and a musician as well; you're never going to measure up to the critic in your head. The same goes for my show — there are still parts of me that are still like, "Oh, but you left a weird breath in there. That one thing that I wish I'd edited out."
Emily: But it's also not something anyone else but you is going to notice. But leaning into the self-critical space — what do you think is something that you've learned about yourself while doing this podcast?
Dan: I've often thought of myself as someone who doesn't always see things through all the way. That would be a major criticism that I would have of myself that's been consistent throughout my life. I can be a little directionless and I can be a little daunted when I have to go downstairs and sit down and edit something from the beginning where I haven't touched it yet, it's just raw audio from Pro Tools. I still have a five-year-old "I don't want to do that" mentality and fight with myself about it. But once I get a kick in momentum, I'm good. And as I do the show, I've found that I've become a better interviewer and I think I've become a better listener. I think early on when I was in a band, I wasn't always the best listener. I was more about like, "This is what I want to say." And there is an amount of that in the show because there's a necessary back and forth. You get a lot more about the guest, but there's always things about me in there because we're talking and having a shared experience. But I think I became a better listener. I think that I've given more thought to things like representation of the different kinds of people that are not straight cis white males and how to make the conversation not strictly around that experience. I want to get as many people from our community on the show as I can. I have this opportunity to hear so many different stories and perspectives that I can't not take them.
Emily: Absolutely. What we do — it's giving a platform to someone else and that's such a gift to them. But like, you know, what you get out of is you've learned over the last couple of years to truly be an active listener and a respectful listener. That's seriously a hard task.
Dan: Exactly. And for the sake of content, I need these people as much as they need me. And the point of this for me is that I wanted to have something to offer, and I think that I do right now, and you can qualify that in whatever terms you want, like metrics and streams and clicks or whatever.
Emily: No, it's all relevant. And relative. What are what are some of your favorite kinds of conversations to have with people?
Dan: I like talking to people who came from a different place than me. That's the most fun. Most musicians I talked to who are Philadelphia musicians came from a 100-mile radius of the city. So it's always nice to talk to someone from Nebraska or wherever. We have to talk about that because you're not from Abington, or you're not from Jersey. There's nothing wrong with being from those places, but it makes sense that this would be where you end up.
Emily: And did you have a couple of people bouncing around for who you wanted on the 200th episode, or was it always going to be Helen?
Dan: It's funny because, as the 200th episode came up, I actually had the time and space in my brain to plan for it. I don't know what people think about this show, but you would be astounded at the lack of planning that goes into it sometimes. I mean, aside from emailing and setting up and scheduling big picture planning doesn't happen normally. But I had a shortlist of people that I wanted to reach out to, and I figured that whoever replied and said they could do it, that's who would do it. And if they all replied, I'd just have to bump them to 201 or 202. So once I zeroed in on Helen and we started to have the back and forth about whether she wanted to do it or not, I realized that she just made so much sense as the subject. She's been doing what I'm doing and what you're doing, what John Vettese is doing, for so long that she's an inspiration. I've been listening to her on the radio since I moved here, and she was like my guide into Philly. When I started doing the show in 2014 and thinking about what it was going to look like, I thought about people like her and David Dye and Terry Gross, and I thought those are pretty good influences to have. They're all very, very good at what they do. I dialed into the people who seem to really get the humanity of the story, and not in an exploitative way. So I just had this tunnel vision for Helen when we were trying to set up the interview. She took a little convincing because she often sits on the other side of the microphone. When I was listening back to the footage I thought, "This is probably one of the best interviews I've ever done in my life." It's definitely also on account of the amount of over-preparation I did for it, which is probably a lesson that I should prepare better for other interviews.
Emily: 200 episodes is a huge milestone, and you should absolutely be proud of the work that you’ve put into this. I don’t want to run a podcast. I have no interest, or time, and for as much as I love talking with people, it’s not as natural for me to facilitate these conversations the way it is for you.
Dan: To quote “Death of a Salesman,” attention should be paid. After doing this for seven years, I’d hope it’s good or I have some messed up priorities. I wanted to make this episode count because I’m not going to get another shot at a milestone for a while.
Emily: You have to be your biggest cheerleader before you can expect anyone else to be, and I think the audience and the following that you’ve garnered is receptive to the work that you’re doing both with and for them. I’m looking out for 200 more episodes. ;)