The Hobbyist #1: Charlie Kaplan & Robert Caro
The New York-based songwriter and label boss explains his love of all-encompassing deep dives that border on the obsessive
photo by Emma Racine
Sometimes I bemoan the fact that I make my living by writing words. Please ignore that this is a silly thing to whine about as it is one of many, many reasons I’m extremely fortunate. Instead, we can focus on my chief complaint, which is that exerting myself “creatively” or looking at my computer all day makes me want to not look at my computer or exert myself “creatively” when the work day ends. Another thing: self-employed, freelancer, whatever you wanna call me; the day never really ends. I could always work on something, there is always an interview to transcribe or some far off blurb that’s like one of those dots in your eye you can only see when it’s not something of focus. So, because I write write write like a lil’ boy Faulkner from the comfort of my apartment, the last thing I wanna do when I am done writing is write stuff that I’m not getting paid to write about. Namely, novels!
I am writing a novel in the sense that I tell everyone I am writing a novel (*adjusts glasses* well, two, actually) and have 50 pages across five excerpts loosely revolving around the same concept. In other words: I’ve got a bunch of junk. I would write more, I tell myself, if only I didn’t have to write so much. The other part of me — much like my friends who hate NFL offenses that pass too much and insist on Running The Damn Ball (RTDB) — is constantly screaming at myself: “WRITE THE DAMN BOOK.” Just do it! Every time I work on it, no matter how much writing I had to do earlier in the day, I feel good! Weekends should be about novelistic pursuits, not paying for $8 Athletics at some sports bar. And yet, it’s another weekend, another $32 + tip on beer that doesn’t even get you drunk and doesn’t taste that good.
Here’s where Charlie Kaplan comes in. The dude does it all. The fact that I don’t have four books published with a fifth novel ready to be released is shameful enough. The fact that someone like Charlie exists and I’m complaining is all the worse. He runs his own record label, Glamour Gowns, which spotlights some of the best artists in NYC and beyond (Charlie gave me a guide to NYC’s most exciting artists. HMU if you want it). He’s a prolific and wildly talented solo artist. His album from last year, Eternal Repeater, is a recent favorite. He has a full-time job working for the music platform Audiomack. He plays in other bands around town, like the great Office Culture. He just had a child! We haven’t even gotten to the reason we’re here, which is that he has an excellent hobby, too. Who has time for hobbies with babies and labels and gigs and recording sessions and JOBS? Charlie Kaplan, that’s who.
His hobby? Expansive deep-dives into his favorite artists. Fine-tune it a bit and we get to his current passion: the work of Robert Caro. He takes long walks and listens to audiobooks from the historian. He started with the Lyndon Johnson series before getting into The Power Broker. Why? Read the damn interview!
I tried to do this same hobby but I absolutely hated it (I will try all hobbies featured on The Hobbyist). I couldn’t hear the narrator over the honking and hollering of the big Apple. I was constantly rewinding and I couldn’t retain anything I heard. I guess I will continue to just read my books like I’m living in 1957. What’s for dinner? Another casserole!
I really hope you enjoy this conversation and I really want you to listen to Charlie’s music. Those are the two things I most want to happen. Buy Eternal Repeater here. Come for all sorts of tips on how to get into the work of Robert Caro. Stay for some useful tidbits on being alive and making art. We also talked a lot about politics because this conversation happened the day after the election. A) Can you believe how long I have been procrastinating with this project? B) Blehhhhhhhhh America.
I knew you grew up outside of New York City. Did you have a fascination with the history of the City as a kid? When did this interest develop?
CK: Strangely enough, I read the Lyndon Johnson series before I read The Power Broker, which is a really weird way to do it, both in terms of the chronology of Caro’s bibliography, but the Lyndon books cover so, so much. I was a government major in college. That was my primary focus, and I've always been way more of a nonfiction guy than a fiction guy. I really love history and biography, and Caro was always one of these Mount Rushmore type authors. At some point, you're going to read this guy and it's going to be a total trip for you. My uncle sent it to me as a gift on Audible, and that moment began a journey which has now gone on for years of me working towards listening to every word of the complete Caro.
As someone who is a professional musician listening to audio books, how do you find the time to listen to them when you are probably wanting to listen to music as well?
CK: It wasn't until I started out on this journey that I realized that the wiring from my brain to my ears is just better than the wiring from my eyes to my brain. I just don't get fatigued at all listening to stuff in the way that I do when I read. I listen to a tremendous amount of music, and when I want to break from listening to music, I want to listen to an audiobook. It's very strange, but one refreshes the other. Once I'm done spending an hour or two listening to an audiobook, then I'm ready to listen to music again and cleanse that palate.
Throughout my workday when I have to be focusing on stuff, I'll be listening to music, which is strangely a thing that I can. I can track both of them in a way that I can’t while listening to an audiobook. For that, I try to walk outside as much as possible. Otherwise I'll go nuts. I walk two hours a day. That's two hours of Caro.
Do you have a job outside of music?
CK: I do. I work for Audiomack.
What do you do for them?
CK: I work on the product itself. Engineers build the product. Designers design the product. The people on the marketing team get the word about it out to the world, and I figure out what we're doing and figure out what the product is, guiding it from being an abstract idea all the way to being something that exists in the world and on your phone. I figure out what we need on the artist side and the listener side.
How did you get into that from a history major?
CK: Right out of school, I was a journalist. My very first job was as the general music intern at NPR Music. That led me to doing some freelance writing for a while, but I was always really interested in technology. This very strange thing happened, where I was meeting journalists and becoming friends with journalists. I met the younger brother of a friend of mine who said, ‘I'm working on this new project. It's like an app. It's kind of like Instagram, but with songs instead of photos and videos.’ I thought it sounded really cool and I offered to help out by introducing him to journalists to start posting stuff on the app. Six months later, they raised over a million dollars in venture funding and made me the first employee of the company. I came on and I was initially named Head of Growth, which sounds ridiculous, I know. That was something I had never done before. I didn't know anything about it. A little less than a year after that, they made me the CEO of the company. The co-founders had never named A CEO, and they kind couldn't agree. I stepped in a little bit more as a mediator or maybe a couple’s therapist. I did that until Audiomack hired me away to start the product team there. It was the school of hard knocks. Everything that I've done is the first time I've ever done it, and I'd had no training in it other than the way that I trained myself.
Do you work from home?
CK: I go to the office one day a week.
And when do you do your Caro walks?
CK: It's an hour in the morning before work and then the evening after work. I just get out there and I do an hour each. It just makes me feel better about everything.
I’m gonna do that as soon as we get off our call.
CK: You feel grateful when it’s over. The experience of doing these walks and listening to The Power Broker in particular was really a magical experience because Caro would be talking about, for example, building the Brooklyn Queens Expressway or the Fort Hamilton expressway through Sunset Park. I know Sunset Park really, really well. I spent a lot of time in Sunset Park, and I can envision all the blocks that he's talking about, as well as envision the communities that were destroyed by Robert Moses’ public works projects. It was this incredibly illuminating experience for me because it felt so specific to my own life. Even though these are events that happened 80, 90, 100 years ago, they still feel incredibly close and familiar and personal to me.
What’s your normal route these days?
CK: I used to live on the Upper East Side and so I would typically walk down 90th street to Engineers Gate, enter the reservoir there, walk around the reservoir, hook into the great lawn, walk around the great lawn, and then come back either up to 90th Street or down 85th Street and then walk back home. It’s about an hour, and it’s glorious. I’ve done it thousands of times, and it never gets old. It's amazing.
Caro is pretty intimidating. How should someone wanting to read but a bit nervous begin?
CK: I highly recommend you listen to the whole thing or read the whole thing, but the introduction of The Power Broker will astound you. The history of it is so striking because while the magnitude of work that Robert Moses did is almost difficult to believe, the music and rhythm of the writing — just the craft alone… It’s unbelievable how good of a writer Caro is. He’s not just a great researcher or a great storyteller. He has often said in interviews that he doesn’t believe that great writing can endure unless it has the music of fiction in it.
Does that translate in the audiobook?
CK: Fantastically. The readers of both the Johnson and Moses books have these real ASMR deep voices. You just never want to stop listening to it. It's like a brain massage. It's incredible.
Where has your interest in the history of New York — or history in general — spun out from Caro?
CK: It hasn’t spun very far outwards because now I’m in a place in my fixation where I watch C-SPAN interviews with Robert Caro every day at lunch. It’s like, something from 2002, and he’s telling all the same anecdotes for the 20th time on a really grainy stream. But this happens to me all the time where I will fall into this deep completist project about somebody, and it takes me forever to dig out. This thing happened to me with Alex G earlier in 2024 where I just went really completist with his gigantic catalog and emerged with playlists of what my favorite of his recordings are. Two years ago I did the same thing with Tom Petty. The year before that I did it with Joni Mitchell. I just can’t get out until something else happens. I don’t know. I hit the bottom or something. I have no idea.
Have you had any other writer rabbit holes like this? Or is Caro your first definitive one?
CK: In some ways, Caro is the first of this type, because it was also the revelation of how I would take the information in. The fact that this is how I’ve gotten into listening to audiobooks is exciting to me.T his is a modality I'm going to exist in for a really long time. When I was working on the album, I had written the lyric that became the title of the album, Eternal Repeater. I couldn’t quite identify why I liked it until I realized that it was this idea of eternal return, which is an ancient stoic concept. It’s described as the physical reality of the universe, that it acts in a perfect cycle and that everything that's happened in the past would happen again.
It’s also a focus of Nietzsche’s Thus Spoke Zarathustra. I decided I was going to take a break from Caro for a little bit and just listen to the audiobook of Zarathustra because it's not that long. I listened to it quickly and later on, thinking about what the album meant to me and where I was coming from, I realized I could apply a lot of the book to my own art and my own work. I absorbed the concepts better than I thought I would, considering it was an audiobook. It’s an entirely different type of tutelage in my life.
Would you recommend others read the Lyndon Johnson series from Caro before The Power Broker?
CK: I would, for a number of reasons. Caro was older when he wrote The Years of Lyndon Johnson. As a result, I do think that it's better writing. The writing in The Power Broker is fantastic, but I think he does have the tendency sometimes to be a little predictable in the way that the information is presented. Who am I to criticize Robert Caro? I shouldn't. But it begins very biographically, very chronologically. The first 20, 30 pages of the first Lyndon Johnson book are just about the weather patterns in West Texas. It’s the only way that you can ultimately understand why his father fails on the Johnson Ranch and why his family becomes so poor, and why Johnson later on in life becomes so obsessed with poverty that he eventually launches the war on poverty. It is a very 10,000 foot view of stuff in a way that is scintillating to observe.
I by no means am saying that you won't have the hair stand up on your arms if you read The Power Broker, because that'll happen to you over and over and over again. There's something about those Lyndon Johnson books that feels so original and organic to the way that story is told.
The full title of The Power Broker is Robert Moses and the Fall of New York, and then the full title of the Lyndon Johnson series is The Years of Lyndon Johnson. That kind of tells you the trip that you're going to go on with each work. Halfway through The Power Broker, it is the bleakest tragedy. It is so dark and stuff just gets worse and worse and worse. After Moses is ultimately deposed by Rockefeller after 44 years of his reign, New York City is so fundamentally changed in a way that can't get unchanged.
He poses this question in the introduction: “Would New York have been better off if Robert Moses was never born?” That kind of answers its own question. If you’re asking that question, then you got bad news coming. Whereas with Lyndon Johnson, Caro has a real different idea. While both are more studies in power than they are biography, the Johnson books end up at this strange, more alloyed place.
Caro asks: “How could this person who was capable of the most progressive social policies that any president ever achieved, period, be the same person who sent 58,000 American soldiers to die in Vietnam and was part of three million Vietnamese people dead in the Vietnam War?” How could that be the same person? There’s allegedly a fifth volume coming. There are moments in the Johnson series where even though you know this terrible thing is coming, you also know this amazing thing is coming. It’s complicated, but there's still a lot of hope and joy to be derived from it, even while you really are mourning the terrible things that happen. You don’t get that from The Power Broker. To put it more cleanly: Read the Johnson series first, but you can’t go wrong.