The Newsletter Market Is Crowded, But Most of Your Competition Is Easy to Beat.

Image: a crowded market with an arched roof in Istanbul, Turkey.
Photo by Danilo Ugaddan

On April 1, I’m teaching a class on The Business of Newsletters That Pay.


Too many writers have no idea why they’re writing a newsletter or a Substack. They’re doing it because everyone else is doing it, or they feel it’s necessary—as in, this is the thing you do now to market, promote, or brand yourself. And a funny thing happens when people feel compelled to undertake tasks they’re not interested in: they find ways to express how the activity is a waste of time.

But for writers who approach a newsletter with intention, it’s one of the most powerful—and genuinely scalable—channels available today. Nate Silver, when he commented on hitting the New York Times bestseller list, put it bluntly: “Someone should probably write a trend story about what my partner and I have started to call the ‘Substack Effect’ for book authors. If you’re someone who’s working on a book, I’d strongly encourage you to start an email newsletter—just trust me on this one.”

He’s not wrong. But most people aren’t Nate Silver and we’ve now ended up with so many newsletters, people ask me what’s the point of starting one. It’s a good question to ask, because you do in fact need a point other than “everyone says to do it.”

The newsletter has to be about something

This remains a conundrum for the unknown writer, and a satisfying answer isn’t likely to come from me. It’s a bit like asking, “What should my book be about?”

If you’re a famous writer with an established audience, your newsletter can be for fans who want to know what you’re working on, where you’re appearing, and what you’re thinking. That can be a valuable newsletter.

But for the average author (especially an unpublished one), no one cares about the minutiae of your writing life—or your random musings—except maybe friends and family. Unfortunately, a great deal of Substacks are just that and eminently forgettable.

So what does work? Obsessing in public. What questions do you lie awake at night pondering? What issues underlie your work that you want to explore? What can’t you stop picking apart? That is what a successful newsletter will be about—not marketing yourself, but obsessing (in a good way).

Most newsletter efforts won’t become valuable until you’ve been producing work for some time and gradually built up a list of people who are invested in what you do. We’re talking months, probably years. But that’s also what makes a real list—one people have chosen to be on, over time—genuinely valuable and not easily replicable by someone else.

Your newsletter can’t be for everyone

This is where most newsletter writers, and frankly most writers in general, go wrong. They try to be for everyone and end up being for no one. The same problem plagues nonfiction book ideas, so if you’re a nonfiction author, you might already know what I’m going to say.

Think about the newsletters and writers you admire who have built real audiences. I’m willing to bet that each of them has a clear position: a specific obsession or perspective that expresses itself consistently. That position transcends format—it can take the shape of newsletters, books, videos, podcasts, events. Once you have a position you believe in, you have the foundation of a real business. You’ll know how to write your About page, which communities to show up in, and what content to create.

Examples I admire

  • Isaac Saul at Tangle: unbiased political coverage, left and right views side by side, that attracts a specific and loyal audience
  • Becky Tuch at Lit Mag News: because of her consistency and thoroughness, I consider her the go-to person for literary magazine news and community
  • Dr. Stacy Wentworth at Cancer Culture: while I’m not a cancer patient, I find her focus on the behind-the-scenes of cancer treatment fascinating (she has a forthcoming book, so a good example in the Nate Silver mold)

The rule here is don’t be mushy. A wide-open “I write about everything” stance deters readers, because potential subscribers look for themselves in your description. They’re more likely to stick with someone who understands their challenges or shares their obsessions.

Should you charge readers for your newsletter?

I’ve already written at length about the inherent problem of Substack wanting writers to charge for their newsletter when the strongest reason for any writer to have a newsletter is to reach readers directly. People aren’t going to pay for you to essentially market to them, but they will pay for consistent value or valuable access—or they might pay if you frame it as patronage (a topic for another day).

If you do charge, one of the bigger strategic decisions for a newsletter is the structure of what’s free versus what’s paid. The old-school approach—a hard paywall where a bit of content is always free and most of it is always paid—can work, but it’s not very imaginative, and it comes with a significant downside: paywalled content doesn’t get shared. No one wants to share an article behind a paywall; no one clicks on links they know they can’t read.

So here are some models worth considering instead:

  • Email delivery is free, but web-based access is not. You send to subscribers for free via email, but the archive is only searchable and browsable by paying subscribers. This can be surprisingly compelling—especially as your body of work accumulates over years.
  • Paywall your content after a set amount of time. When it first publishes, make your content free, taking advantage of online sharing and discussion. Then after a set period of time, move it behind a paywall.
  • Limit community interaction to paying subscribers. Comments, a Discord, or direct access to you might be reserved for those who pay.
  • Free subscribers see ads or sponsor placements. This assumes you can attract advertisers—which requires knowing your audience well enough to describe them to potential advertisers.

One model to be cautious of: paid subscribers get more of the same content. Most people don’t want merely more content—they probably already lack the time to read what you send. But they might want something different, like access or community that free subscribers don’t receive.

Advertising and sponsorships: an underexplored option

Writers consistently overlook advertising as an income source probably because book publishing has never depended on it. But it shouldn’t be overlooked. Advertising dollars have been shifting away from traditional channels toward creators who reach a desirable, specific audience.

The key phrase is desirable, specific audience. There isn’t some magical number of people you have to reach before you can accept advertising or sponsorship money. What matters more is engagement and who they are—their demographics, interests, and purchasing behavior. The easiest way to test the waters is to simply let your subscribers know that you’re accepting classified ads or sponsor placements, and see what response you get. Your first advertisers are likely to be subscribers first.

The bottom line

If you want to earn money from your newsletter, don’t start with the technology or the publishing frequency. Start with the question: What’s my focus, and who is it for? The rest follows from that.


If you’d like to earn money from your newsletter, no matter where it lives, join me for The Business of Newsletters That Pay on April 1.

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Joshua Doležal

A few footnotes from a Substack veteran. I’ve experimented with nearly all of the paywall options over the past four years, and none of them work for me, even though I’m still stubbornly trying. Readers pay for access when the topic is incendiary (a grievance that mobilizes one tribe while trolling another tribe) or when there’s a clear ROI (growth hacks, investment advice). Or they’ll pay just because they want to support you, personally. The latter seems to be the case for my following. When I started on Substack, the hype was sky-high, and we all thought we’d be earning a primary income if we kept grinding away. But the algorithm and in-house promotion methods keep changing, often to amplify the biggest fish, so I’ve come to accept that Substack is more of a lead magnet for me. The $2-3K I make from subscribers every year is a nice bonus, better than the zilch that most lit mags pay but unlikely to ever be a primary gig. I’ve also scaled to the point where my distribution exceeds that of even top-drawer literary journals. Very few journals exceed 1,000 subscribers. But you can eclipse that with your subscribers and followers on Substack. I keep hoping they’ll develop an in-house ebook tool and store, but until then reach is the reward.

Joshua Doležal

This is a good question. Short answer: it’s evolving.

I launched “The Recovering Academic” in 2022 during a major life transition. I’d just left a tenured faculty position for a family move and had planned to pivot to independent writing after publishing in lit mags for years. But lit mags were changing, and the pathways to traditional publishing were closing (in nonfiction at least), even for folks like me with a long publication list, so I came to Substack out of desperation.

Years 1-2 were really about leaving higher ed. I wrote several longform pieces for “The Chronicle” on that topic and riffed on it twice a week in my Substack series. But that was a narrow audience, and kind of an angsty one. I didn’t want to be writing about leaving something forever.

Year 3 shifted to memoir craft and a fatherhood WIP as proof of concept. That was an attempt to center my book coaching and editing. But there’s a lot of that on Substack.

Year 4 is now squarely focused on the medical humanities (my original research emphasis).

Most of my paying subscribers have stuck with me because they’re interested in me. But I’m accepting that most of the things that fascinate me endlessly, that I won’t tire of writing about, are not ideal for making money. The real value is modeling the craft that I teach and attracting clients who admire my taste.

D.L. Lee

“I’m accepting that most of the things that fascinate me endlessly, that I won’t tire of writing about, are not ideal for making money.” So true.

D.L. Lee

Thanks Jane, there’s good food for thought here, and one big question that will help me decide whether advertising and sponsorship is a strategy worth the effort: Do I have a desirable, specific audience? I started my Substack in Jan 2023 with the goal of building audience for my unknown authorial brand. I began by publishing my debut novel in weekly chapters which built a subscriber base of around 200+ in the first year. Once the last chapter was published, I pivoted to my newsletter (From the Source) which synthesizes timely evidence-based, peer-reviewed (where possible) scholarly articles that align with the themes in my novel, and support my value proposition: the wellbeing of women and girls. Although I bring in a small annual income (I have an active buy link in my newsletter), my ultimate (and longterm) goal is book sales. As of today, I have 413 subscribers and 7,812 followers, my growth curve is incremental and steady as I also benefit from recommendations and share my posts on LinkedIn, Instagram and Threads. While readers of my post now average 260-300 views per article, few people like or comment on them; some share their thoughts with me direct in email (!?). When I started my newsletter, my target audience was women. Interestingly, I have acquired a lot of male followers and subscribers (I see this trend on LinkedIn as well). I’d love to be able to recover my costs and get out of the red, but beating the competition feels like it will demand a time commitment that will take me away from the writing of my second novel. Or will it? 

D.L. Lee

That’s a sobering and pointed article… interestingly, Salman Rushdie’s arrival on Substack was what piqued my interest in the platform. It may be that this is a good time to devote all my time to my next book while rethinking my strategy. Of one thing I feel certain: given how long literary projects take, there’s every chance that by the time I come up for air, Substack will have raised an IPO and disappeared into Meta. Thanks Jane, as always!

Erron Adams

I mostly came to Substack to get beta readers for my novels as I release them this year. I haven’t asked for expressions of interest in the beta reading thus far, so I’m not sure if it’s a strategy that will work. For me personally time will tell but I’d be interested in your thoughts regarding a strategy like this, Jane.

Ellen Hudson

Jane, I read D.L. Lee’s comment and your reply. May I ask an opinion? I am admittedly frustrated with my attempts to break into the industry. (As stated in a comment above)I am working on a newsletter. I asked two successful authors who’ve given me a lot of advice and support regarding serializing one of my manuscripts on the newsletter. I got two opinions: “it can’t hurt” and “ABSOLUTELY do not do that!”
Any thoughts from you?

Ellen Hudson

I have seen “Wattpad” but didn’t know what it is, as I have mentioned, I have been self-learning writing and publishing.
Perhaps this is incorrect, but I had read that when querying, agents will do an internet search to discover more about the author. Without social media accounts (I have none) I read the very basic is a webpage. I thought by serializing one of my manuscripts, an agent might read some of it and not think I am a loser and waste of their time! Your reply has convinced me this is not the best use of my precious prose.
Thank you for your kind advice. If I’m never successful in becoming published, at least I’ve been fortunate to engage with so many in the business and have been astounded how helpful everyone is! In these trying times, it is wonderful to feel goodness in others.

Ellen Hudson

Thank you.

Brutus Macdonald

Great title!

Richard Murray

My newsletter starts with my social critique, then some crafting technology, then current work I have created from the last edition to the current. Should I split those up?

Richard Murray

What do you want to become known for over years?
In each news letter most of what I highlight are literatures or illustrations, which I want to be known most. So I need to restructure my newsletter and place the literature + illustrations on top?

Richard Murray

ah thank you:)

Sarah Lavender Smith

Thanks for this smart article! I’m grateful I started my weekly Substack 4.5 years go, and it has grown to ~4700 subscribers. It’s very niche; it’s called Mountain Running & Living (sarahrunning.substack.com) with the tagline “personal essays with practical advice about trail running, mountain life & midlife grit.” I mostly write about the sport of mountain running with themes central to my memoir in progress (such as evolving and adventuring in midlife). I’m writing to share how I solved the question of whether to charge for content. Most of my posts are free, as are most of my subscribers. But paid subscribers get (1) an occasional bonus post (usually two/month) and (2) an invitation to a monthly Zoom meetup, which has built a thriving community. My paid subscribers number only ~130, but that’s not nothing, and I love the monthly Zoom with those who attend! One tip: Don’t send out paid posts to free subscribers with a “teaser” of content followed by a paywall. This is annoying for the recipient and leads to many unsubscribes, as I discovered when I did that. I only send paid bonus posts to paid subscribers.

Amy

I want to write a spoof called ‘please don’t make me read your substack!”

Ellen Hudson

This was very interesting to me, as I am in the process of creating a website. I haven’t seen any specific advice, with the exception regarding whether or not to be “political” if the focus on your newsletter isn’t politics.
Personally, I like the idea of pay-if-you-want-to-post-a-comment. I know someone who does this and claims it limits the trolls.

Thank you, Jane. I am grateful people have pointed me in your direction as I am learning so much here.

Laura Zinn Fromm

This was a great piece, Jane, and true in every way. Thanks for writing. I too have found that subscribers pay for subscriptions because they want to support me, and that trying to separate the content for “paid subscribers” versus content for “free subscribers” doesn’t pay off. I admire people like Nate Silver, Heather Cox Richardson and Becky Tuch for (presumably) making real money off their Substacks, but that also (I suspect) requires a staff and is a full-time commitment. I view Substack as a way to reach fellow readers and writers, and hopefully future students and clients. It’s an easy-to-use, effective and rewarding marketing tool.

Stacy Wentworth

Thank you for the s/o, Jane. And thank you for reading!

TERESA DOVALPAGE

Another super interesting post! As a reader, I mostly use Substack to follow a few favorites for free. I prefer spending my free time on a good physical books rather than reading anything online. As a writer, I’m not sure how I’d balance a newsletter alongside a full-time job and my own fiction…it really does all boil down to time. Thanks for the free posts, Jane. I always appreciate your perspective.