We talk with writers, editors & entrepreneurs about, really, anything. All conversations are 'manuscript-first', meaning they were typed as you see them. Small edits have been made for structure.

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Episode LIV: "I was young and full of a billion ideas but had no clue how to execute them"

Published 3/2/16
In this installment, I speak with Jason Diamond. Topics include starting Vol. 1, other Diamonds, filling word quotas, growing as a writer, trimming fat, ‘finding your voice’, his memoir & more.

Today I’m with Jason Diamond, a writer, an associate editor at Men’s Journal, the former literary editor at Flavorwire, ditto with Jewcy.com, and the founder of Vol. 1 Brooklyn. These publications vary widely, and I want to get into that, but let’s start easy: How and why’d you start Vol. 1 Brooklyn, and what have been the key kinks along the way?

I'd been living in New York for a few years and really didn't know how to get a foot in the door as a writer. I wanted to write about books, but I didn't have any publications or know any editors that would let me. So I basically did what I grew up seeing people I respected in the punk scene do and decided to start something myself. I figured if I wrote about books, authors, and other things I liked then that counted as a publication. I joke and say it was a ploy to get free books, and it isn't far off from that, but it was also a good way to practice writing on the fly. 

In terms of kinks: Money. I'm not the best when it comes to making money off of something I love. Tobias Carroll, my Vol. 1 partner, also comes from a similar background, putting out hardcore records, zines, etc. and I think we both just look at it like it's something important and it's something we love. Maybe one day we will get it together and figure out how to not spend out own money on it.

That's the rub across the board when it comes to books, but hey—who's going to let that stop them? Can you dip into your roles at Flavorwire, Jewcy and now Men's Journal?

Of course. I came on as the editor of Jewcy on a whim. It was sort of a weird operation because 1. It was Jewish pop culture site. Pretty niche. 2. It was under the umbrella of a non-profit Jewish record label. 3. It was just me and no budget. Super fun, but it was tough. 

Flavorwire was great. I'd been a managing editor at their other site, Flavorpill, but saw the opening and decided to go for it. It was intense because we had a daily quota to fill, but it taught me a lot. I also got to work with some of the most brilliant people I know. 

After that, I just needed a switch. I saw the Men's Journal opening and thought it might be interesting different. I mostly handle the food and books stuff and I get to work with a ton of writers I love, so it's always really fun to come to work and see a piece waiting for me by somebody like Jaya Saxena or Margaret Eby. 

Considering you worked for Jewcy, is it correct to assume that, like Mike Diamond, you’re also a jew?

I wish more people asked me if that's the Diamond I'm related to. I like to think the Beastie Boys had a huge impact on me as a person but also as a weird Jewish kid.

Am I correct to assume you're not related to the other Diamond, Jonny? (The Beastie Boys also had a huge impact me as a person and a weird Jewish kid.)

I am not. Jonny is an Irish Diamond. Yeah, I have this theory about the weirdo Jews like the Marx Brothers, Ramones, Beastie Boys, etc. The anti-establishment smart-ass types. They taught me a lot.

When you say that your work at Flavorwire taught you a lot, in what ways do you mean?

Well. The quota was definitely tough, especially because trying to find two pieces to write 500 words or more on when your focus is just books isn't as easy as I'd imagined. Well, I never imagined it to be easy. But still. 

I made the joke that I was in luck if Philip Roth said something or Zadie Smith had a story in The New Yorker because then I had something I could maybe turn into a post. But making lists, coming up with reaction pieces, essays, etc. was difficult on that constant basis. So it showed me how to get creative on how I wrote and discussed things, how I looked for stories, but also how to turn around good copy in a really short amount of time. 

I think there's a collision of aspiration with practicality that anyone who wants to be in the industry and write has to survive. Can I ask about how you saw yourself as a writer in that gestation period before Vol. 1, and then how that has changed to today?

It's funny because I've been thinking about this a lot over the last few months. I was young and full of a billion ideas but had no clue how to execute them. I thought you could just drink a ton of coffee and type. I was really raw and really in love with the idea of being a writer, maybe not so much trying to figure out how to go about it. I never was an intern anywhere, never got my MFA, never had any sort of formal training so to speak. I just sorta jumped in. And I'm glad I did, but I wrote so much garbage.

Today, I really like being edited. I've been lucky to work with some editors that really kicked my butt. That and knowing and reading so many other great writers and watching how they work has been my education.

The most important change I'd say is that I've learned that I'm always learning. I probably thought I knew everything ten years ago and I didn't know shit. 

In what tangible ways did the editors you got to work with change your writing? (For those at home, Jason's written for The Paris Review, The New York Times, New York and other fine institutions.)

So many things from pointing out the little spots I didn't think needed more work to just looking at their track changes and really thinking about why they did that. They also taught me to trim the fat. I used to think I HAVE TO FIT EVERYTHING INTO THIS PIECE, and that sounds silly to me now, but I think when you're young and things feel hopeless and you feel like you're not going anywhere it's understandable. I always look at everything like it's my last chance, like maybe nobody will want me to write for them again after I turn in this piece. It's this weird thing I have built into my brain that's still there. Only now I realize that it's better to leave a beautiful corpse and not some bloated thing with a lot of words and thoughts that might not be necessary.

Mm. I just read a great list (maybe it was even on Flavorwire, honestly), about top whatever quotes about editing. One of them was: if it sounds like writing, cut it. I think that sums it up, and it's also just a maturity thing, like you say. How much of your maturation as a writer do you think has come from your experience within writing, and how much just you maturing in the God-given biological way?

I love that. It's definitely an experience thing and probably a confidence thing as well. I think I started out not realizing I was maybe mimicking the style or tone of certain writers I respected because I was really not comfortable with my voice. I think as soon as I started to realize people were maybe interested in what I was writing about then I started opening up a little more. I don't have a ton of confidence in myself, so it was sort of like baby steps in a way. 

I hear it said (or written) that 'finding your voice' as a writer is an important part of the process—as if there are other parts, as if those three words don't fit everything between them. What is that process, actually? Is it writing you like you talk to yourself? Is it expressing yourself without affectation? Is it conveying ideas that exist in you so they exist in the reader in the most efficient way possible?

I used to wonder if I had to take peyote or some psychedelic and wander through the forest for a few days and only then would I find my voice. Writers do tend to talk about it like it's this mystical thing, but it is something you really do have to search for and you do that by making mistakes and learning. I think ultimately it's really any of those things that depends on the writer. For me, I think it's trying to find that balance between being open and personal with the reader, but also telling a story. I always want the reader to know that I'm seriously interested in what I write. I know that might sound silly, but I've read so many things in my life that can be so tight and smart, but I stop reading it and think, "Wow. That writer didn't give a shit about that subject."

Ha. And speaking of. You've got a book coming out, a memoir called Searching for John Hughes, which I assume is a replay of your life if you looked and talked exactly like him?

Ha. Sort of. Actually there's a good deal in the book about trying and failing to become a writer. Ultimately the book is about how we experience art as individuals, the meaning we attach to certain artists and their work, and how I did that and might still continue to do it with the work of John Hughes. I'm from the area where his best-known films were set and I grew up with that idea that my life was supposed to resemble one of his films. I eventually took that obsession to New York and figured that even though I had no clips and really no experience that I was destined to write his biography. I kinda didn't let go of that idea for a very long time. Like nearly six years. So when people ask what the book is about, I either tell that that or I just say that it's about failure. 

Either way I'm hooked. What's the structure of it?

It's funny because I thought it was just going to be all about me in New York and Chicago chasing after John Hughes, but my brilliant editor was like, "I want to read about your life." I initially thought that's silly, but then I realized my childhood and teenage years really explain why I'm so obsessed with his films. The hard part was thinking about my past and figuring out a constructive way to tell it and make it interesting and not THAT sad since there's a lot of bad stuff there. So I started thinking of some of the memoirs I'd recently read and loved like Rosie Schaap's DRINKING WITH MEN, Cheryl Strayed's WILD, and Joanna Rakoff's MY SALINGER YEAR, and thought about how they structured their stories and how Strayed and Rakoff are also novelists that transitioned to telling their personal stories. I thought about how those books work so well for a number of reasons, but mostly because they know how to tell a story, and so many memoirs are just like 1. I was born. 2. The fatty part you came for. 3. We're all better people. But really great memoirs work as great books with great stories all the way through. Obviously if you're a celebrity you can get away with just telling stories of parties and drugs and all that, but I couldn't get away with that. 

Well I can't wait to pick it up. We're out of time, Jason, and so I'll say thanks for coming on and for your words.

Thank you so much for your great questions. I really appreciate it.