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Photo by Danilo UgaddanOn 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But for the average author (especially an unpublished one), no one cares about the minutiae of your writing life—or your random musings—except maybe friends and family.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 the 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 is how many people you reach 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 is this actually for, 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.
