🔴 A newsletter I would email you if we were friends

Today’s guest is Caitlin Dewey, creator if Links I Would Gchat You If We Were Friends, a newsletter she started in 2014 while reporting on social media for The Washington Post. She wrote it for 2 years, then took a 4-year break before bringing it back in 2020; earlier this year, she went all-in to make it her main gig.

In this issue:

• 💵 Monetizing her newsletter a decade in

• 📰 Tension between journalists and creators

• 🪴Building a sustainable lifestyle business rather than a media empire

— Francis Zierer, Editor

P.S. We have a podcast! Listen to our full interview with Caitlin or watch it on YouTube.

This spring, Caitlin Dewey completed a rebrand of her newsletter, Links I Would Gchat You If We Were Friends, and for the first time, she launched a paid subscription option.

She’s been working as a journalist since graduating college in 2011 and started Links in the first month of 2014 while working at The Washington Post as a social media reporter. Shortly after starting her newsletter, Caitlin became the Post’s first digital culture critic; the beat gelled well with her work on the newsletter, which she published multiple times per week, sometimes daily.

Issues were easy to write (she never spent more than an hour on a given issue) and easy to read, rarely including more than 400 words; she’d write an intro note and include briefly-contextualized links to three articles or other pieces of internet.

Six months after launch, Links landed a recommendation in The New York Times, not the last mention it would earn from traditional media.

Links was a formalization of exactly what the title describes; a way for Caitlin to get more out of the research she was already doing for work, finding a home for stories and slices of internet that didn’t fit into her primary output. She’d already spent years curating an RSS feed that sat at the core of her work — today, though she’s sending the newsletter to over 23,000 readers, that RSS feed is still her crystal ball.

Sabbatical

On the eve of the 2016 election, not two years after the first issue graced inboxes, Links suddenly went dark. The last issue, sent on November 2nd, 2016, was a guide on how to safeguard your sanity in the last days of the election. “By all appearances, it looks like I stopped because of the 2016 election,” Caitlin says. “That is not the case. I actually got a new job.”

She was still at the Post but had switched beats to food policy. Two years later, she changed jobs again, moving from D.C. back to her hometown, Buffalo, to work for The Buffalo News, reporting major narrative and investigative projects on topics like housing and economic development.

Then, just a few weeks after the pandemic shut America down, Caitlin sent out the first issue of Links in nearly four years — “I suddenly find myself with a lot of links, a lot of aimless screen time, and a *very* unexpected, born-again appreciation for the peculiarities of internet culture.”

By last fall, having been writing the newsletter the second time around for longer than she had the first time around, and seeing other journalists leave traditional media for gainful independent newsletter projects, Caitlin quit Buffalo News to do the same.

Replacing a local news salary with newsletter subscriptions

The Links relaunch, which happened on May 1st, is most visible in three changes.

First is the brand and visual language, as seen in the above site header.

Second is an increase in publishing pace; whereas the original version of Links sent almost every day, the post-pandemic version was usually once per week; the post-rebrand version sends twice weekly in distinct formats.

Third is the addition of a paywall for the first time.

Until this May, Caitlin had not directly monetized Links; it was “a pro bono enterprise.” There is now a $7/month option ($70 for a yearly plan). Saturday editions of the newsletter are classic link roundups and Wednesday editions are original essays; free subscribers only see some of the Wednesday editions and don’t get access to the gift links guiding readers past paywalled article in the link roundups. Paid subscribers also get access to planned community-focused events and experiments.

Three months after the rebrand, Caitlin said she’d replaced “roughly 40%” of her salary at Buffalo News. That was two months ago; when we spoke, she told me the number had increased to “over half,” pacing ahead of the revenue goals she’d set.

So far, all her revenue is subscription-based, but she’s “tiptoeing into ads,” working on a trial basis with an ad salesman to see if the additional revenue stream might work for Links. She’s still taking on freelance work as a supplement.

“There is this perceived tension between ‘content creators’ and journalists”

Caitlin never aspired to be an entrepreneur and has a distaste for that side of indie journalist life. She may have replaced over half of her local news salary, but the Buffalo is a union shop, and she gave up excellent health insurance by leaving.

She knows she’s supposed to be “posting TikTok summaries of my newsletter, and getting-ready videos where I also talk about digital culture,” in order to drive audience growth, but says, “You will never see me doing those things because they're not in my wheelhouse. I'm not good at them.”

Caitlin does not feel a tension between herself as a journalist and creators, though she sees this tension in others. She, of course, admires the work creators do — it’s work she’s spent a great deal of time immersed in covering internet culture — but sees it as separate from what she does and not in competition.

There’s no need to build an empire

Caitlin’s goal in leaving traditional journalism to go independent is nothing more than to live a happy, healthy, and sustainable lifestyle on her own terms. She doesn’t want to have employees; she wants to produce work she’s proud of and make a middle-class income doing so.

The current academic semester is Caitlin’s first teaching; her third source of income at the moment, after Links and freelancing. She’s an adjunct at Syracuse University, teaching a twice-weekly class on magazine writing that she took as a senior at the same university 13 years ago. Nothing about what she’s teaching has changed since she took the classes except for some of the examples she’s teaching, which now include stories from writers like Anne Helen Peterson and Jia Tolentino.

Links takes up about two-and-a-half workdays per week researching and writing Links, plus a half day on admin work like writing thank-you notes to paid subscribers. She still freelances out of necessity but doesn’t say she would stop were her income from Links to suddenly balloon beyond the heights of any previous salary; again, she likes the work. Weeks that she newsletters, teaches, and freelances, she says, “I don’t sleep a lot.”

Though she works on Links alone, Caitlin does feel a sense of community with some of her fellow newsletter writers. It’s a massive group, much larger than when she started Links a decade ago. The writers she is in community with trade advice and help; she can’t recall that any of them have ever turned each other down.

Most of her growth to 23,000 subscribers has come via this community and her readers. And “readers” is indeed the word — when I asked Caitlin to describe her “relationship with her audience,” she said, “Even saying ‘audience,’ I don’t really want to refer to them in that way.”

Read and subscribe to Links I Would Gchat You If We Were Friends.

For the full story, listen to our podcast or watch it on YouTube.

🎙️ As ever, it was impossible to fit every topic we discussed into the newsletter. In the podcast this week:

• 📆 Creators, journalists, creator-journalists; ethics and audience growth

• 🔗 The art of building an excellent links aggregation newsletter

• 💻️ Differences in writing about the internet today vs. a decade ago

Listen on your preferred podcast platform or watch on YouTube.

Do more than just replying to your readers’ emails

Every creator or indie journalist business is a relationships business. Those relationships may be parasocial, but attending to them builds trust and accountability both ways.

The simplest way for newsletterists to do this is to email all new readers. This is standard practice; we do it at Creator Spotlight and respond to all good-faith responses in kind.

Caitlin takes it a step further. In preparation for her rebrand, of course, she surveyed her existing readers (the list then numbered nearly 15,000 emails) and did follow-up video calls with three dozen respondents.

To encourage paid subscription signups, Caitlin decided to mail a Links sticker to the first 100 people to sign up, along with a handwritten thank-you note. She enjoyed doing it, and the stickers weren’t expensive; she decided to keep it going for every paid subscriber (you opt in after signing up).

She even made an Instagram account to follow readers back and create a sort of two-way parasocial relationship. None of this is strategic — this is just who Caitlin is.

Listen to the latest episode of Tasteland, the podcast hosted by Creator Spotlight editor Francis and Dirt Media CEO Daisy Alioto.

This week we’re joined by Bibi Prival, a fragrance development director with 20 years of industry experience. We talked about …

• Building a career in fragrance

• Teaching kids how to smell

• How TikTok is changing fragrance culture

• Scent memories

• What fragrance evaluators actually do

• How fragrance marketing has changed in the past twenty years