The Producer Behind Some of Substack’s Most Beloved Newsletters

Erin Shetron talks life before Substack, overrated writing advice and how she approaches marketing and branding

photo credit: John Shetron

Earlier this year I had a moment where I threw my body across my laptop in editorial delight and shouted, “Why is alllll this writing sooooo goooood?” 

Awash in emotions from finding yet another amazing essay, my years in editorial production were making my spidey senses go off. 

There was a feeling, something rising off the page among some of my favorite Substack writers—a polish, an honesty, a surprising element to their writing. Most of all, when I read anything from

Alex Dobrenko`

or

Rae Katz

, everything was a complete experience. There was nothing dangling off a visual ledge. Nothing that made my head turn sideways or get distracted. And then one day Alex mentioned he worked with

Erin Shetron

.

My editorial sniffer’s still got it, I thought. They have an Erin.

I’ve wanted to bring Erin out from behind the “editorial veil” for a little while now so that all of you could benefit from the insights, wisdom and humor I’ve also been the lucky recipient of. And this interview is the result of that. 

If you’re an established writer who’s in a wayfinding season, I think you’ll find something refreshing in this interview. If you’re brand new to Substack, Erin has practical insights that I know will help you right where you are. And if you’re just plum cynical and overworked and tired of all the same junk the world is doling out, please keep reading—Erin has been in the trenches and offers a heartening story of finding her way to meaningful, good work.

What kind of work were you doing before and what prompted a pivot to Substack branding, coaching and editing? Specifically, what about your work made you want to leave it and find something different?

Before taking on Substack clients, I had been working as an in-house marketing director since 2016. I helped launch an edtech company and then a succulent subscription company with the same founders. I ran a team of marketers, designers, and social media managers, and I loved it. It was scrappy and exhausting and chaotic and problematic and thrilling, and my team was unbelievably fucking great. I mean truly supportive, creative, smart people. But then the founders and I stopped seeing eye to eye, and after a long stint of disappointing conversations and frustrations, I decided to leave. Most of my team ended up leaving, too. And honestly, something broke in me. 

COVID was at its height, I was in a taxing romantic relationship, and even though I had planned to take time off to try to recover from my burnout, I instead found myself more depressed than I’d ever been. I had left this amazing, six-figure job that turned so sour that everyone in my life was relieved when I gave notice. I had enough money in the bank to take some time off and figure out my next move. But I couldn’t get my shit together. 

Finally I took another marketing director position at a company I knew in my gut wasn’t going to be a good fit, but I felt I had to do something, and when I left that job nine months later I was right back where I was before. Except this time, panic was starting to set in. My money was running out and it seemed like every job description I found was for an underpaid, team-of-one, do-ALL-the-things-with-no-support type of role. I had some great interviews and offers but would get exhausted just thinking about the lack of support, collaboration, and creative freedom I'd have. Nothing was the right fit.

Wow, I didn’t know I was going to write this much, but I’ve never really tried to tell this story before. It feels important to explain the level of burnout and panic I was contending with. Because then my sister, who is my absolute everything, my guiding light, sent me a link to a goofy job description she found for a “marketing human.” It was basically like, “I write stuff on Substack, and sometimes people really like it, and I’d like someone cool to help me figure out how to get it in front of more people so maybe they might like it, too. Oh and please be organized because I am not.” The job description made me laugh, so I decided to read some of the newsletter. And then I was like, this guy fucking rules. That guy is Alex Dobrenko of

Both Are True

. 

Reading that job description and his essays reminded me of what I was so energized by when I was building a company from scratch and running its marketing: playful, creative, out-of-the-box storytelling that treats audiences with real tenderness and respect. So I sat in my tiny yellow kitchen that night and giddily wrote Alex an unhinged email about how I could use my ~10 years of digital marketing experience to help him grow his newsletter. 

We got on a call the next day, and the week after that we began our work together. Eight months later he’s gone from 2,000 to over 5,500 subscribers, received a Substack checkmark, and so much more. I am endlessly proud of him and our little trio, which includes editor Madeline Friend, who is such a badass. Helping Alex design his subscription offerings, content calendar, pitching story ideas, and tracking his performance metrics all made me love marketing again. Especially because I was doing it my own way, in a creative editorial environment, and with support. I felt alive again.

Screenshot courtesy of Erin of an early-on meeting with Alex. Yes, this is her winning “Employee of the Month.”

So what, exactly, do you do for the Substack writers who are your clients?

I'm part growth strategist, part marketer, and part editor/content collaborator. I help clients produce their best, most subscribe-worthy newsletters. This means I get to be really agile, which I find super rewarding—one day we might talk about their branding, and another we might come up with ways for reaching new audiences while nurturing existing ones. In the mix of all this, I’m also editing their first drafts and keeping an eye out for opportunities to improve paid subscriber conversion rates. And then there are all the options and functionalities specific to Substack, like referrals, Notes, chat, threads, welcome emails, welcome pages, boost settings, etc.

What were your first impressions of Substack, especially after having worked in/on different marketing platforms? 

My first impressions of the dashboard were not great. I was like, “Where is all the data? What is happening here?” I remember being nervous that I was going to be able to do my job given how limited the functionality was and how few performance metrics existed. I’m happy to say that Substack has come a long way since then, and it’s heartening because I think they are really focused on giving the dashboard more powerful marketing features. But I have a lot of ideas for improvements if anyone on their team wants to hear ’em ;)

What should writers take advantage of while Substack is still a fairly young platform? 

Networking. That word sucks, I know, but what I really mean is participate. Don’t just write your stuff and hit publish and hope someone somewhere finds it and likes it and shares it. Substack is so unique because it’s full of influential writers, readers, and executives all talking to each other. Get on Notes, join Office Hours, leave comments on people’s writing you admire, be your weird little self and have some fun. Every single one of my clients has made progress in their readership growth by putting in a little time each week to participate on the platform. What goes around comes around, and whatever good vibes get doled out in the Substack-sphere, I’ve seen them come back in the form of a restack, mention, collaboration, comment, subscriber, or even the coveted Substack Featured Publication badge. These connections count. Go forth and forge them!

What could prove tricky for writers on Substack who aren’t as familiar with online writing?

Something I see a lot is that folks forget that there’s a design element to online writing. If you’re a writer, that’s probably annoying to hear. You might be used to online or print publications that would format and add design for you. But on Substack, packaging your writing is almost as important as the writing itself. Your logo, email headers, welcome page image, and post formatting all matter.

A lot of your clients have pretty robust dialogue with their readers. Is that something you think is important for writers?

Yeah, I do. I think some of the most popular Substacks are proof enough that engaging with your readers is an essential growth strategy. Readers want to feel like part of a community, they want to be let in. They want belonging. This is one of the amazing features of Substack — there are so many ways to engage your audience in conversations that are so much more resonant than, say, the ones taking place on social media. You can build a real community.

I think building this dialogue is important on a personal level, too. Writers, like most artists, sometimes struggle with self-doubt, creative blocks, etc. and having a close connection with your readers can really help guide you through those tough times. My clients and I have polled readers and been really touched and motivated by the responses. Readers have so much useful and encouraging feedback to share, and engaging with them can really help get you back on your feet when you stumble.

How do you help your Substack clients navigate or package the free versus paid side of their writing? 

How to define and grow a free and paid offering on Substack is on a lot of people’s minds, and it’s something I work on every day. One thing I can say with confidence is that clearly packaging free versus paid content and then tailoring specific goals to grow each audience will yield more progress than saying, “I want to publish whatever I want, and I want to see growth across the board, in every area, as soon as possible.” We all want that, but it’s not specific enough to build a solid, testable strategy around. 

For example, a few months ago Rae and I decided to focus on paid subscriber growth with the goal of reaching 100 paid subscribers and getting her that orange checkmark. I created a cadence for publishing paid content, tested different ways of promoting each piece, and ran different deals to convert current free subscribers to paid. We reached our goal, and now we are shifting to a new goal of growing her free subscriber list to 2,500 by the end of September. To achieve that goal, I’ll sketch out strategies that focus more on brand awareness than conversion — things like identifying relevant Substackers for collaboration pitches, participation on Notes and Substack Office Hours, and engagement in the comment sections of newsletters with overlapping audiences.

There’s a lot of advice on Substack for writers. What’s one piece that you think is overrated?

Maybe, “write from the heart.” No. Write from your gut. Write from your fucking loins. I don’t know, just go deeper. The heart is fickle. The gut knows.

Instinctually, I cringed at the thought of “branding” myself as a writer because that carries a lot of pressure and has, historically, felt fake. Can you share a little bit about how you see branding differently?

Branding gets a bad rap, but it’s heart work, which writers already do by default. It’s asking yourself, “what is my work really about, what is its essence, what is its purpose, what does it evoke?” Branding is just taking the answers to those questions and making sure each decision you make about your work stays true to them.

For example, if you find that your work is whimsical and playful and its mission is to evoke a quality of lightness, joy, and hope, then everything from your newsletter’s aesthetics to copy style to tone should all reflect those characteristics. There are a ton of great examples of Substackers who do this well, but one of my favorites is

Caroline Chambers

, who writes What To Cook When You Don’t Feel Like Cooking. If you’re a writer who is intimidated by the word “branding,” just throw it out. It doesn’t matter what you call it, it is just about making sure your work is highly recognizable, consistent, and authentically presented. 

When you’re meeting with a potential new client, what are you looking for in terms of practical writing experience? And also in terms of their posture toward writing in general?

I tend to gravitate toward people who surprise me with how honest they are, no matter the topic. I work primarily with personal essayists now, but I’d love to work with folks who don’t necessarily see themselves as “writers” first — maybe they’re an archeologist, an activist, a stripper, a balloon animal artist. I want to work with people who are invested in stories.

I also think writing can be collaborative, not just some solitary strife of a lonely, unshaven guy hiding away in a lighthouse or cabin or man cave or whatever. So that’s important, too. I want to work with people who value input and are open to riffing with me.

What does it feel like when a client brings you a piece of writing that amazes you? What’s it like having a front-row seat to some of this really great writing? 

It’s so exciting it’s almost unbearable. Sometimes I find myself just grinning at my computer screen. Other times I finish a piece and I have tears streaming down my face and I usually say, to no one except maybe my dog, “What the fuck,” which means, “Oh my god, how did they do that, how did they write the thing I could never express?” And then I recover, put my marketing hat back on, and get to work trying not to say, “Publish it now, right now, go go go, everyone needs to see this now!”

Can you tell us a little bit about your process when a new piece comes in?

First, I make sure I’ve had something to eat, something to drink, and my body is in a decently relaxed state. It’s very difficult for me to take in new information when I’m hungry. Then I get to reading. I usually make some copy edits as I go, mostly because they irk me too much to leave alone, but the first read is really just about fully absorbing the piece, letting the writing make its mark on me. If the piece is long or dense, I reread it a few more times. Then I start reverse engineering it, which I think might be one of my “skills” that I never really knew was a skill. I don’t remember being taught to do it, it’s just something my brain does. I start deconstructing the piece into segments, looking for the studs that are holding it up. Then I name the studs. My clients know this about me, I love a subheading. 

Then I see how the studs are currently organized and start looking for things like arc, continuity, and clarity. I look out for phrases that don’t sit right with me and I try to ask a question about them. I make note of loose ends, elements that were introduced but never followed up on. I think, If I was a reader and this was the first piece I ever saw from this writer, would I get what’s happening here? Am I being let in on the joke, or do I feel like I’ve stumbled upon a private conversation and should see my way out? Are we jumping right in or do we need to back up a step and include an intro? Is there a part that I keep losing focus on — should we scrap it? 

I would say that’s another big part of my process, and another thing my sister taught me–asking thoughtful questions. My clients know this about me, but almost all of my notes start with “I wonder…?” or “What do you think about…?” Then I pass it back to my client, and they either answer those questions with their rewrites or we grapple with the questions together until we land in a place that feels good and true. And then we get to work positioning and promoting the piece, which is a whole other thing! 

If you could write down what your clients have taught you, whether about writing or life, what would that thing be?

My clients have taught me more than I could ever keep track of, let alone write down, but I’ll try to put words to a few of them.

One important thing I’ve learned (or maybe I’ve re-learned it for the millionth time) is that I don’t have to know everything. Sure, I have a good chunk of marketing experience and some decent writing/editing chops, but I used to toil away on a problem, alone and panicking, until smoke was coming out of my ears. But then one day Alex was like, “nah it’s just as good if you’re the person I figure it out with vs the person with all the answers.” And my other clients have that same mentality, for which I’m so grateful. I love when I can guide them, but I love figuring it out with them even more.

I’ve also learned to trust my instincts when it comes to pitching essay ideas. Whenever I’ve pitched a topic for a new essay and a client has run with it, some magic occurs and the piece performs really well. It’s such a cool experience, and my clients trusting me has really helped me regain trust in myself.

Lastly, though there are so many more, my clients have taught me how to be disciplined while holding our work lightly. All of them have experience with burnout, and while they care deeply about their work, they all go to bat to protect their energy and mine. We do not overwork ourselves. The vibe is: if the work feels good to make, it’ll be good. We are honest about where we’re at, emotionally, mentally, and physically. In this way, our partnerships are incredibly healing as they are rewarding.

***

New Ask-an-Editor this week! Practice trusting your writing instincts.

Join your host Amanda and other writers to share your craziest, weirdest, biggest, most “out there” essay idea. Tell us what you’re working on (or what’s rolling around in your head) and get supportive and real-life, applicable feedback from a developmental editor on how to bring that essay to life.

This is ideal for: Writers who get caught in the web of “second guessing” their essay ideas or struggle with trusting their creative instincts

It’ll be happening: This Thursday, Aug. 24. Come-and-go format, all day long.

How to join: If you’re a paid reader, you’ll have instant access to share your essay idea in this week’s Ask-an-Editor thread. Or you’re invited to sign up for a 7-day free trial. (Paywalled to keep this a safe, supportive atmosphere with other writers who are also working with their “first thoughts” creative energy!)