This is the continuation of our Grow interview series, designed to share the nuts and bolts of how writers have gone independent and grown their audiences on Substack. It has been lightly edited for length and clarity.

We invited Jessica DeFino, who writes beauty-critical publication The Unpublishable, to share her insights on going paid in order to free herself from pressure and deadlines and write a book, converting subscribers, and experimenting with the newsletter form.

What’s your Substack about in one sentence?

The Unpublishable is what the beauty industry won’t tell you, from a reporter on a mission to reform it.

What do you offer readers?

I’ll start with what I don’t offer readers: product suggestions or shopping roundups. The Unpublishable is the first and only beauty publication that won’t push products on you. Which brings me to what I do offer: a perspective on beauty and skin care that serves individuals rather than industry.

I have a pretty unique insight into the beauty industry from my background: launching the official Kardashian-Jenner apps in 2015, working as a staff writer at a beauty publication, then reporting as a freelancer for places like the New York Times and Vogue. I know firsthand how beauty standards are manufactured, how marketing spreads misinformation, how advertisers and affiliate sales affect what gets covered by the beauty media. My work seeks to dismantle those standards, correct that misinformation, and explore how beauty culture affects us all—physically, psychologically, and psycho-spiritually.

Because of all that dismantling, my writing can sometimes come off as contrarian or extreme. Aggressive, even. But the way I see it, it’s about love. It’s about freedom from the patriarchal, capitalist, and colonialist structures that support the beauty industry. Freedom from the boxes (both literal and metaphorical) that keep us small. Freedom from unattainable ideals, cultural conditioning, and manipulative marketing. Freedom from the thought that self-esteem is injectable, that Amazon can deliver empowerment, that external beauty has anything to do with your inherent worth. There is a wild, open, soul-deep type of beauty beyond the industry of beauty; a type of beauty that can’t be bought and sold. That’s what I hope to help people find.

Growth by numbers:

Started Substack: February 2021
Launched paid subscriptions: February 2021
Free subscribers: 21,730
Paid subscribers: 1,190

A look at Jessica’s subscriber dashboard.

Why did you decide to go paid?

I launched a free, donation-based newsletter in May 2020, which I sent out via my personal website. I converted to Substack in February 2021 specifically to go paid. This was right around the time I started working on my (still forthcoming) book, and the goal was to put the brakes on freelancing.

I did not want to deal with the chaos of freelance reporting—pitching, follow-ups, edits, invoicing, chasing people for payment—while trying to write a book. A paid newsletter felt like a good solution; it offered me a way to release content that was more casual, created on my own terms, with a lot of freedom and not a lot of pressure, and get paid for it too.

I know this sounds like a cheesy marketing line, but Substack’s interface truly did make it really easy to lead my pre-existing readership into a paid experience (so much more natural than soliciting donations with a PayPal link). A solid percentage of people from my previous mailing list and my Instagram audience became paying subscribers, which gave me the freedom I needed to focus on my book, keep my name out there, and generate some income.

What’s your content strategy?

Deadline-free: I value freedom and ease: for me, that is the whole point of having an independent newsletter. The content itself is about adding value for my readers, but the creation of that content is about adding value for me. Why would I self-impose a hard schedule and deadlines when I don’t have to? I truly just go with the flow and write when inspiration strikes.
I keep an open draft: I do, however, have one biweekly feature for paying subscribers called The Don’t Buy List, which features mini-critiques of beauty-industry current events from the previous two weeks. I always have a draft going, so whenever a new product launches or a bit of juicy beauty gossip surfaces, I open the draft and shoot off a few sentences. By the end of two weeks, I have my list. I usually just polish it up the day before.
Paid subscriber perks aren’t just content-based: There are three paid perks. After The Don’t Buy List, one of the perks is “content that doesn’t push products on people.” The other perk for paid subscribers is the ability to comment on my posts. Before Substack, I was very active on Instagram and commenters could be very mean. Keeping Substack comments open only to paying subscribers means that comments come from people who understand the context around my work enough that they’re willing to pay for it, so any discussion or debate will likely be of the healthy variety, or I’m at least making money off the mean people.

Why would I self-impose a hard schedule and deadlines when I don’t have to? I truly just go with the flow and write when inspiration strikes.

What’s the sharpest insight you can offer other writers about growing on Substack?

Make your best content free. For me at least, there’s a bigger mission behind my work, and that is to materially change beauty culture. I can’t do that—like logistically, I can’t reach the amount of people I need to reach in order to affect change—behind a paywall. In my experience, readers who appreciate and engage with your free content will share it, and some of them will eventually pay for it.
Capture now, convert later. I make sure my big ideas are free and accessible in order to reach the widest audience. It’s worked for me so far!
People want to support! This has been the biggest realization for me with The Unpublishable. The fact that over 1,000 people have decided to pay for this makes me feel so supported.

What advice have you received about growing your publication that didn’t prove to be helpful?

The most trite piece of advice for growing your audience is to publish on the same day every week, at the same time, to build anticipation and trust. From my experience, it isn’t necessary for an email newsletter. I’ve experimented a lot: sending emails every Tuesday or every Thursday, morning vs. afternoon, weekends vs. weekdays—and my open rate is high and steady no matter when I post.

I think the silently-agreed-upon “Tuesday morning newsletter” can backfire. I subscribe to so many newsletters, and so many of them send their posts on Tuesdays or Thursdays at 8 or 9 a.m. sharp. I end up reading fewer of these pieces, if only because a bunch of them pile up, whereas if I get something in the middle of a Wednesday or late afternoon on a Friday, it’s like … Oooh, a little treat. Let me take a break from working and read something.

What has been a meaningful moment for the growth of your publication? How did that happen?

The biggest moment of growth for my newsletter was this viral tweet. Unfortunately, you can’t plan that, but you can take advantage of it when it happens.

Read: Injury as a Beauty Ideal: But first, my viral Kardashian tweet

Jessica DeFino @jessicadefino_

I was an editor on the Kardashian apps in 2015 in LA, worked days nights & weekends, could only afford groceries from the 99 Cents Only Store, called out “sick” more than once bc I couldn’t put gas in my car to get to the office, & was reprimanded for freelancing on the side ❤️

Variety @Variety

“I have the best advice for women in business,” Kim Kardashian says. “Get your f--king ass up and work. It seems like nobody wants to work these days.” https://t.co/HuddEEXmoM https://t.co/KJCIlaVX3S

I turned the tweet into a thread that highlighted the work I do in my newsletter with a link to subscribe. I made sure the link to my Substack was in my bio on Twitter and Instagram. When the media reached out for comment, I asked them to credit me as “Jessica DeFino, writer of the beauty-critical newsletter The Unpublishable.” I made sure that anyone who saw my tweet, or my name, associated it with my newsletter. I ended up converting about 9,000 free subscribers (so far) from all that momentum.

Takeaways

Pin an “about this newsletter” post to the top of your landing page. I think this is the easiest way to grab new readers who find your Substack. It gives them an immediate feel for your content, your vibe, and your writing. Personally, I feature a “praise for” section right at the top of this post that highlights media quotes about my newsletter, but I think a “people are saying” section that features feedback from satisfied subscribers would work just as well. It’s all about showing social validation!

Don’t be afraid of quick-hit content! My writing tends to get a little heady and heavy, so I find it helpful to break things up with shorter, lighter pieces. I started a series called “1 Minute Musings”—literally just four or five sentences on a particular topic—which gets surprisingly high engagement via likes, comments, and shares. You and your readers deserve a brain break every once in a while.
Experiment with form. I’ve been trying to break out of the “2,000-word block of text” thing by testing new formats, which is exciting for me and, it seems, exciting for my readers. My top posts of all time include a poem made up of lines from the beauty PR pitches I received that week, a line-by-line “close reading” of a skin-care brand’s launch announcement, and a half-baked rant including (badly) hand-drawn diagrams of the existential beauty paradigm as I see it. Don’t waste the incredible opportunity writing a newsletter offers by creating the same kind of content you would publish anywhere else. Readers respond to things that are fresh and new and maybe even a little weird!

Who’s another Substack writer you’d recommend?

Amy Odell of Back Row. Her newsletter has an “unpublishable” vibe, except it’s focused on the fashion industry. It’s brilliant.

What questions do you have for Jessica that we didn’t ask? Leave them in the comments!

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To read more from this series on growing your publication, see our interviews with Mike Sowden, Elizabeth Held, Jonathan Nunn, Polina Pompliano, Michael Williams, Judd Legum, and Caroline Chambers.

On Substack

Grow: How Jessica DeFino converted…