I have spent thousands of hours thinking about newsletters. I've written my personal newsletter for over eight years, growing it from a tiny little friends-and-family newsletter to a sprawling ten-thousand subscriber behemoth.
But more than that, that tiny little personal newsletter inspired me to start Buttondown, a platform dedicated to helping folks get their newsletters off the ground and into the world. In doing so, I've helped over ten thousand would-be writers start their newsletter, collect subscribers, build a community, and even make money. I've seen first-hand what works (and what doesn't); I'm coming armed not just with anecdotes but with cold, hard data.
I know, I know. "Thought leadership" has become a bit of an icky phrase these days, especially if you spend enough time on Twitter or LinkedIn to fall victim to one of those obnoxious page-long screeds.
But it's a real thing — establishing yourself as a foremost individual in a thing you genuinely care about is a powerful lever for your career.
We live in an age where our relationship with others — whether its friends and family, an audience of adoring fans, or prospects and potential customers — is mediated by a black-box. That black-box might be the infamous "Twitter algorithm"; maybe it's the TikTok For You feed; maybe it's Google's fey SEO heuristics.
Regardless of which black box you're thinking about, three things are true:
There's only one true escape from the black box: a list of email addresses. It's harder to gain an email address than, say, a TikTok subscription or a Twitter follower, but once you have it there's no capricious technocrat to sit in between you and your subscriber.
(Okay, you could be pedantic here and talk about how Gmail [aka Google] powers like 85% of the world's email subscriptions, and they implicitly can act like a monopolist over the inbox if so they choose. But that's picking nits.)
Okay, we got all the nice, happy, rah-rah stuff out of the way.
To throw some cold water on your fervor, I wanted to lay out some hard truths as well — you have probably read tons of thrilling success stories (including many in this very ebook!) about how newsletters changed folks' lives, but relatively little (digital) ink is spilled over how difficult and slow it can be to start a newsletter from the ground up, especially if you don't already have an existing audience.
Here's a good sign you've settled on a niche that works: can you easily describe your newsletter's value proposition in 140 characters?
Let's take some popular newsletters as examples:
All of these taglines have a few common threads:
Some things to avoid:
Now that you've chosen a topic you're passionate about, it's time to decide the second most important thing — how often you're publishing!
There are three main criteria that your publishing cadence should fulfill. Let's introduce them, and then talk about each more in depth.
Your ideal publishing cadence should be:
I'm gonna get the most important thing out of the way first: the most common — and the most dangerous — way newsletters fail is by burning themselves out.
Newsletters — just like any sort of content creation, like a podcast or a video series or anything! — are a serious commitment! They take time and energy and can feel often feel Sisyphean, especially in the early goings when it might feel like you're writing to an empty room.
On the other side of the spectrum — it might be infinitely easy to maintain a publishing cadence of "whenever I have time and/or feel like it", but your subscribers will not be having a great time.
Subscribers — and the finicky email algorithms that make sure they see your writing front and center — like consistency. Consistency may be the hobgoblin of little minds, but consistency — even at a very slow publishing cadence, like once a month or once a quarter — is the key to success:
The final variable — and the trickiest to reason about sometimes — is to make sure your publishing cadence matches what you're writing about.
If you're largely commenting on breaking news or industry buzz, temporality is everything!
Conversely, if you're trying to write long-form, atemporal pieces, publishing every week will cheapen the effect that an email has on your subscribers.
There is one cheat code to the publishing cadence discussion that gets overlooked fairly often, which is (roughly):
Writing one 500 word emails is about the same amount of effort as two 250 word emails.
This is not exactly true, of course — there are lots of fixed costs to writing an email, like lining up sponsors or coming up with subjects and so on — but it's mostly true, especially when you're planning out your time.
So if you find yourself really confident that, say, the right cadence for you is three-times-a-week but you're a little skittish about the commitment that entails... maybe experimenting with shorter-form or commentary/riff-driven emails as opposed to longer, extemporaneous missives is the way to go!
An "info product" is a bit of a cringe-y term for a one-off paid piece of content, like an ebook or a white-paper.
Personally, I think building info-products are one of the most underrated monetization options for an active newsletter audience:
There are loads of positive knock-on effects that come from cross-publishing your newsletter content to a blog:
It is fair to worry about a couple of cons:
TL;DR — I think cross-publishing is a no-brainer unless you have a very explicit reason not to.
Dedicated IPs are like [INSERT PUNCHLINE HERE] — if you don't know what it is, then you don't need to worry about it.