How to get your first thousand subscribers

Introduction

Why you should listen to me

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.

Why you should start a newsletter

...Thought leadership...

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.

An audience you can own

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:

  1. The black box is invested in your success — after all, YouTube isn't a huge hit if there aren't any creators on it!)
  2. ...But it's invested in everyone's success more than it's invested in your success.
  3. The black box can take away your audience whenever it wants, if so it chooses.

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.)

Why you shouldn't start a newsletter

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.

  1. If you're already struggling to think of topics or produce content, a newsletter — another content outlet! — is going to make things harder, not easier.

Define your success criteria

Choose a topic

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:

  1. TLDR.tech: "TLDR is the free daily newsletter with links and TLDRs of the most interesting stories in startups 🚀, tech 📱, and programming 💻!"
  2. The Pragmatic Engineer: "Big Tech and high-growth startups, from the inside. Highly relevant for software engineers and managers, useful for those working in tech."
  3. Create and Sell: "Twice weekly, in-depth email marketing advice for creators."
  4. Pome: "Short modern poems for your inbox"
  5. The Unpublishable: "What the beauty industry won't tell you, from a reporter on a mission to reform it."

All of these taglines have a few common threads:

  1. What the broad topic is.
  2. What the angle on that broad topic is.
  3. Who the author is.
  4. Who the ideal reader is.

Some things to avoid:

  1. Unless you're already an established creator with a massive audience, avoid overly general newsletters. "Whatever is on my mind" might make for easy and cathartic writing — and there's nothing wrong with that! — but it makes it hard for subscribers to know that your newsletter is the right one for them, and it'll be difficult to create the sort of feedback loops and flywheels you need to reliably grow your subscriber base.
  2. On the other end of the spectrum, niching really far down is a great idea, but make sure you won't run out of content! You need to choose a topic that at minimum you feel comfortable talking about every month, so make sure your topic or angle isn't something with an expiration date or an obvious finish line. (If there is, maybe it's content better suited to something finite like a paid e-book.)
  3. This is perhaps stating the obvious, but: choose something you give a damn about. If your brain and market research says you should be writing about trends in basketball free agency but your heart says you want to write about gardening... your readers are going to be able to tell that your heart's not in the former, is all I'm saying.

Choose a publishing schedule

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:

  1. Maintainable over a very long period of time.
  2. Frequent enough that your audience stays informed and engaged with your work.
  3. Concurrent with your success criteria and subject matter.

Maintainability

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.

Frequency

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:

  1. It's easy for you to build the habit of writing and sending if you know you need to always have something ready to go by, say, Friday morning.
  2. It primes your subscriber base to expect your email in their inbox, which means they'll read and engage with it more.
  3. It provides an air of professionalism and stability that is important for almost any success criteria, whether its driving folks to be patrons of your writing or establishing your credibility as a consultant.

Concurrency

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.

The hidden variable: email length

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!

Choose a name and domain

Finding content

Choose your tools

Avoid analysis paralysis

Publish your first newsletter

Promote your newsletter

Friends and family

Social media

Paid acquisition

Lead magnets

Monetize (if you want)

Do you need to monetize?

Paid subscriptions

Sponsorships

Affiliate links

Info products

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:

  1. It's a great way to re-package your existing writing in a new format.

Resources

Frequently asked questions

Should I cross-publish to a blog or have my content "just" live in my newsletter?

There are loads of positive knock-on effects that come from cross-publishing your newsletter content to a blog:

  1. Search engines like Google and Bing will be able to index your content, which means you'll be able to reach a wider audience of organic traffic over time.
  2. You'll be able to share your content on social media, which means you'll be able to reach a wider audience of social traffic over time.
  3. Subscribers will more easily be able to share your content with their friends and colleagues (I know forwarding emails is technically still a thing, but internal statistics show that five people send a permalink to an email for every one person who actually hits "forward")
  4. It makes it much more easy for you to cross-reference and link to your own content, which means you'll be able to build a more cohesive body of work over time as opposed to a series of one-off emails.

It is fair to worry about a couple of cons:

  1. Your content is no longer "exclusive"! This is a very real concern, but I think it's a little overblown. The vast majority of your subscribers will not be reading your content on your blog, nor will they have it bookmarked.
  2. You'll have to manage two different publishing workflows — one for your online blog and one for your newsletter. While there might be a bit of up-front work required, tools like Zapier or Buttondown's built-in RSS integrations make this a breeze.

TL;DR — I think cross-publishing is a no-brainer unless you have a very explicit reason not to.

Lots of platforms are talking about a "dedicated IP". Do I need to worry about that?

Dedicated IPs are like [INSERT PUNCHLINE HERE] — if you don't know what it is, then you don't need to worry about it.

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