On being disciplined
Prelude
Jake Brennan is the creator, main writer and host of Disgraceland, a podcast that focuses on true crime in music, entertainment, and sports. Brennan also writes music for the show and is the author of the 2019 true-crime book Disgraceland: Musicians Getting Away with Murder and Behaving Very Badly. Prior to Disgraceland, he played in the Boston-based bands Cast Iron Hike, Jake Brennan & The Confidence Men, and Bodega Girls. He currently lives in Florida.
Conversation
On being disciplined
Podcaster and musician Jake Brennan discusses mastering the art of storytelling, listening to your audience, and continuing to make stuff.
As told to J. Bennett, 3288 words.
Tags: Podcasts, Music, Focus, Time management, Failure, Success, Process.
You’re a connoisseur of music and entertainment history. The true-crime stories you tell on Disgraceland are wildly entertaining, but with many of them, there’s a sense of gravitas as well. I just listened to the Bill Murray episode, which is fantastic, and generally lighthearted. Before that, I listened to the Anthony Bourdain episode, which, given his untimely end, has a much more serious tone. How important is it for you to find the right balance in conveying these stories?
It’s very important. I do it in almost every episode I write, and I write about 90 percent of the episodes. But I do have writers that I work with occasionally. The Bill Murray one I didn’t write, which is why it’s lighter. It’s harder to convey heavy tones, but I think for me, I’m always trying to personalize it in some way. I didn’t realize that was what I was doing.
A lot of people don’t like that aspect of the podcast. But to me—okay, I’m reading this book about Martin Scorsese right now, and I’m not comparing myself to Martin Scorsese, but I’m comparing the mediums where creators make things and they’re just entirely personal. Mean Streets, Goodfellas, they’re very personal movies to him. The Bourdain episode was very personal to me because right around that time, I lost two siblings to suicide—one in 2014 and one in 2018. You never really get beyond that grief. You’re always working it out in some way—not walking around crying or whatever, but it’s always there. That episode was me working that out a bit.
Absolutely.
We also did a Matthew Perry episode. In writing that episode and researching addicts—specifically opiate addicts—I learned so much about myself and how I fucked up my relationship with my brother, how I could have done it differently. It all made it into that episode in a weird way. Not in a preachy way, but for me, it’s there. It’s not by design; it’s just how I write. It comes out personal a lot. The subtext is personal, I guess is the point.
You consider yourself a storyteller, not a journalist. That’s a crucial distinction, but why is it important for you specifically?
I never aspired to be a journalist. The nuts and bolts of being an actual journalist don’t fit my lifestyle. To me, a journalist is somebody who goes out and digs up and extracts a story. But I also think 90 percent of what is described or categorized as journalism today is not journalism. It’s storytelling.
I was listening to this interview today about this guy who was covering that attack on Paul Pelosi, Nancy Pelosi’s husband. This guy’s a Gen-X journalist, a liberal guy. He shows up and he’s there to cover the story. There’re all these other journalists from CNN and places like that, but he’s independent. He’s like, “So, did you guys canvas the place? Did you guys go knock on doors?” They’re like, “No, why would we do that? We don’t want to offend the people who live here.” He’s like, “You’re fucking journalists. Get in there, ask questions and tell the story.” That’s what journalism is to me. Nowadays, what gets passed off as journalism is: Something happens, there’s an established story depending on what your political point of view is on the topic, and then a hundred people just write the same damn thing. That just fundamentally does not interest me at all.
I go out and research. I do a ton of research, but I do very little calling people and talking to them and asking them questions. Frankly, if I did that, I couldn’t operate at the volume I operate at. When I’m writing about John Lennon, who the fuck am I going to talk to who’s going to give me any new information anyways? You know what I mean? This stuff’s been out there for years.
And a lot of it is hagiography, not legitimate biography.
Right. I really love that we’re talking about this because we were just discussing this yesterday—me and my guy, Zeth, who writes for me and researches all kinds of rock stars and musicians. We’re old enough now that we’re well into the rock n’ roll mythmaking and industry of it all. All the big stars have sort of written their story or devised their story and gotten it out there.
The Beatles made that whole Anthology thing in the nineties, so that became the established Beatles story. Well, I have all this other information from books that came out before that, and it’s fucking crazy. I tell these stories, and I post them online and people are like, “That didn’t happen.” I’m like, “Okay, well, you’re saying it didn’t happen because you’re looking at the established narrative that the band wants you to believe.” I’m looking at a story in a book by their fucking publicist, Peter Brown, who was with them every single day and told this story because he was right there when it happened.” Yeah, it’s my choice to make that decision and to tell that story, but I just think that’s more interesting. It’s not journalism, though.
You maintain a vigorous schedule for producing Disgraceland episodes. You mentioned that you have a research assistant, but you’re also doing a lot of that research yourself. Plus, you’re writing, narrating, and sometimes making music for the segments. What kind of time management tips do you have?
It’s pretty psycho. It’s always been disciplined and heavily scheduled. I know everybody’s different, but as a guy who makes things and has to actually go through the act of either researching or writing, I will research for one week and then I will write for one week. That’s basically how I do my part of the episode, aside from voicing it, which takes me an hour and listening to the mix, which doesn’t take a lot of time. And I have to do that creative heavy lifting first thing in the morning. I get up really early to do it. In the last few months, I don’t know if it’s because I’m getting older or what, but it has been really hard to get up. I’m like, “What the fuck is going on? I’ve got to change something up.”
So, I’ve been doing this thing lately that is just, it’s fantastic. I get up at five, I don’t have coffee; I have a cup of tea. I know it’s more caffeine, but it’s different. I don’t know. I feel different. I’ll write or research for about two and a half hours, and then I’ll let myself fall asleep for 20 minutes—and then I get up like a bat out of fucking hell. I go in the backyard, and I sit in the sun for five minutes. Then I get into my day, doing the less difficult creative stuff. By then, it’s nine or 10 o’clock, and I’ve already done the hardest thing, which is what I need to do.
You made a key creative decision when you started the podcast: A scripted, solo narrator format. So many music and true-crime podcasts have multiple hosts, and I find them unlistenable because you’ve got people talking over each other, and people making comments or inside jokes that don’t have anything to do with the subject of the show. Tell me about why you made that decision and why it’s become important to Disgraceland.
It’s really the necessity is the mother of invention type of thing. If you want to interview people, you have to rely on scheduling. That’s a huge thing, and I didn’t want to do that. In the beginning, I actually thought I was going to do the show with a bunch of guys. We didn’t really know what it was going to be, and quickly, people weren’t as interested as I was. I was like, “Fuck it. I just have to do everything, I guess.” That’s what I did.
You launched Disgraceland in 2018. How long have you been able to make your living from it?
Immediately. When I launched in February of 2018, something like seven days later, it went to the top of the Apple Music charts. It was number four. It beat Obama and Oprah. I was immediately selling ads. I was in a deal with iHeartMedia within eight months, and I’ve been in multiple distribution deals with other media companies. It allowed me to build a production company called Double Elvis, where we produce other music-related content shows for other folks.
We had 17 full-time employees about a year ago. We’ve cut down to just below half of that now, given how the industry has contracted. 2025 is going to be different. It’s going to grow. Advertising’s going to rebound. I foresee us growing in the future, but it got a little out of hand there when suddenly I’m responsible for 17 full-time employees and their families and all kinds of shit. Not that I’m responsible for their families, but I was thinking when we were cutting people: “Shit, man, this guy’s got kids.”
But look, when I started Disgraceland, I had just lost my first real job. Before that, I’d been a musician my whole life. Then it was like, “Oh, I’m going to have a family. I have to find a real gig.” I did the podcast thinking, “I’ve been in studios, I know audio, I like podcasts. Maybe this will convince somebody to hire me for something else related to audio.” It just turned into a thing, which I’m so grateful for.
When your passion becomes your job, how do you prevent it from turning into work?
Well, I don’t know that I have avoided it. I mean, I definitely got distracted. I won’t go into details, but I’ve sold the rights to my podcast for television. I wrote a screenplay for literally the biggest actor in Hollywood. I spent two years on it, and it fucking didn’t work out. It’s like my eye was taken off the ball and it had become work. My ambition got the best of me in a weird way… maybe “ambition” is the wrong word. For someone who grows up working class and playing in bands that never really did what I wanted them to do, all of a sudden, I have all these fucking insane opportunities. I got flown to Milan to interview Elton John. I don’t even do interviews. You know what I mean?
It was just one of these things where I was like, “I’ve got to do everything” because that had never happened to me before. It was like Gandhi showing up at the all-you-can-eat buffet: “Oh my God, I get to just fucking go to town here.” Suffice to say, it didn’t all work out. But the one thing that has consistently worked out is the thing that I love the most, which is Disgraceland: Writing these stories and telling these stories and talking to my listeners about them every single day. If you’re going to discipline yourself to get up at five in the morning every day, okay, that’s work, but I fucking love it. I get up and I write about the Go-Go’s and Anthony Bourdain and Ice-T. If it feels like work, it’s my dream job.
The bands you were in—Cast Iron Hike, Jake Brennan & The Confidence Men, Bodega Girls—were all very different stylistically. To me, that shows a willingness to try new things. Do you think that’s part of why you attempted a podcast even though you had no experience?
Yeah, absolutely. I actually think that approach for a creative person—trying different things—there’s a difference between that and showing up and making shit every day. I actually think the Ramones model, the AC/DC model—those guys were just like, “This is what we fucking do, and we’re going to do it every single time because this is what the audience wants and demands of us.” I feel that now.
I’ve made some weird fucking podcasts in the last few years that no one’s ever heard of. They had a ton of marketing and promo behind them from major networks—I was already getting calls for television—and then, nothing. When I do the music and true-crime thing, it just works. Like I said, I listen to the audience and what they tell me. I do think there’s a certain creative aspirational thing to be like, “I’m going to make my jazz record now, or my reggae record.” But it’s so hard to get your audience to come with you, man.
You obviously landed on your feet, but before you started Disgraceland, how did you cope with the disappointment of being in multiple bands that didn’t work out the way you wanted?
Even though Disgraceland is a very successful endeavor—and like I said, my dream job—I’m still disappointed as a creative person all the fucking time. I hear shit that comes back that I made and I’m like, “What the fuck, dude? This does not sound like I wanted it to sound.” Or I’ll put an episode out and be like, “This is going to be great.” And then people hate it, or it doesn’t get the response you want. Or, like I said, there’s these other endeavors that didn’t manifest the way I wanted them to.
But I’m very critical of my musical career. Especially now, looking back at decisions I made, things I did, people I aligned myself with. Not that anything was anybody else’s fault but my own. The one thing I will keep in mind is that if that shit didn’t happen, none of this would’ve happened. It’s all cumulative. As long as you don’t stop doing and just keep making stuff, the motion will lead you somewhere and everything you’ve done in the past will matter. Driving around the South in a van with no air conditioning in 1997, smelling other dudes’ farts, listening to Hank Williams, and getting shit on by my bandmates for listening to country music and telling these wild stories—that’s what Disgraceland is.
You’ve been in creative collaborations within bands, and now you’re in a situation where you’re in charge. What’s the best balance for you in terms of other people’s input versus your own creative control?
The bands I was in were all very collaborative, and I wanted it that way. I now believe that was a mistake. I’m not saying a band needs to be a dictatorship, but there needs to be somebody who is clearly in charge. If I were to do that again, that’s how I would do it. Now, I’m not saying it would’ve made those bands succeed. It wouldn’t. In some cases, it would’ve made the bands far less successful than they were, and probably not as good musically in a lot of cases. And I would be more ruthless about it. I know that’s not a word that creative people like to hear, but the greatest ones are fucking ruthless. Bob Dylan is ruthless. Kurt Cobain was fucking ruthless. I don’t know anything about Jeff Tweedy, but I guarantee you that motherfucker is ruthless.
But then to throw water on that a little bit, I do have a collaborative relationship with my writers. I do take their input—and with everybody I work with: The guys who work on the music, the guys who work on the audio. And a lot of cases, I trust them so much, I won’t even review things. That’s how collaborative it gets. But at the end of the day, it’s like, I’m Kim Jong-fucking-un, man. I am the little dictator.
Is there a creative philosophy you could point to that ties all of your creative endeavors together?
Yeah. For the first two years of the podcast, I was deathly afraid of it failing. It was the first thing I’d ever done that succeeded, and I didn’t know what I was doing right. I had no fucking idea why people were liking it. I was like, “If I fuck up, I’m not going to know why I’m fucking up.”
I realized by accident somehow that I had been writing and telling my stories using a method that’s as old as Aristotle. Literally, he developed it: Aristotle’s Poetics, also known as the Hero’s Journey. I also found this David Mamet interview, and it was a really snarky, nasty, curse-filled rules-for-writers type thing. Every rule he mentioned, I had been doing without knowing that I was doing it. The I only reason I was doing it was because I had consumed so much storytelling in my life—books, movies, documentaries. I’m not a comic book fan, but I looked into the methods of the great comic book writers and other mediums, like the pulp writers from the ’30s and how they would actually write the beats to get people to physically turn the page. I used some of that stuff, too, but it was mostly the Mamet thing. Once I realized that, I decided to deploy Mamet’s rules for every single story I tell. It’s just great storytelling.
Jake Brennan recommends:
The Great Beauty – Whenever I’m not writing and I’m doing anything else in my workday, I have Criterion’s live-streaming channel on. I watched this movie last week called The Great Beauty by Paolo Sorrentino. It’s one of the most beautiful movies I’ve ever seen in my life. It won an Oscar in 2013 for Best Foreign Film, but I didn’t know that when I was watching. It’s the greatest depiction of the coolest old guy you’ll ever run into. The movie says a lot about what’s important in your life and how you guide yourself on whatever path and where you end up.”
American Cosmic – The last great book I read that didn’t have anything to do with research is called American Cosmic by D.W. Pasulka. She’s a religious studies professor, and this is a look at UFOlogy and anomalous aerial phenomenon and the whole alien thing through the lens of religion and media and how media influences our take on it—and specifically how Catholicism has been involved since the beginning. It is fucking mind-blowing.
“Grinder Man” – I was trying to think of an album to tell you about, but that would’ve been disingenuous. I don’t listen to albums anymore. We live in a singles world. “Grinder Man” is a weird song from a record that John Lee Hooker made with the Stax label. It’s about a baseball player, but it’s a double entendre: ‘Grinder Man plays everyday.’ And it is so fucking violent. I don’t mean the lyrics—I mean the sound. If they ever let me write a movie, I’m using this song in the most violent scene.
American Alchemy – This is mainly a YouTube podcast, and it’s kind of new. The host is Jesse Michels, and he’s like 30 or something. It’s heretical thinking, mainly. It challenges every institutional norm around history and science in a very intellectual and well-researched way. And he has incredible guests. I highly, highly recommend American Alchemy.
Creem – Creem magazine is back. I know it’s only quarterly, but it’s almost too much awesomeness. My son goes through it, and he can’t believe what it is. I tell him, ‘Yeah, dude—this is what it used to be like every month in the ’90s. You’d get Rolling Stone, and your mind was fucking blown on every page.’ And Creem has the greatest tagline, too: ‘America’s Only Rock N’ Roll Magazine.’ So badass.”
- Name
- Jake Brennan
- Vocation
- podcaster, musician