Tips and tricks from Buttondown's engineers, writers, and fans.

Guides and tips

When Hygraph neé GraphCMS emailed a 31% off Halloween discount to their subscribers, it was only reasonable to expect a modest uptick in sales. Shopify customers spent $9.3 billion on Black Friday 2023; surely, of the thousands subscribed to the GraphCMS newsletter, some would grab a discounted plan.

Cue the team’s shock when not only did no one use the discount code, but also over 200 people unsubscribed instantly from their emails. Even more concerning was their awareness that “devs are more likely to hit that spam button than you’d like to admit,” a fact born out in Hygraph’s data and numerous comments on Hacker News to that effect.

“This experience was my first, and hopefully biggest, mistake in email marketing to developers—treating them like any other user,” 

Some people want to know how they can save money on your product. Others want to know how your product can save them money, effort, and time. Knowing the difference between the two segments, letting users opt-in to the emails they want to receive, and sending the right emails to the right folks can be the difference between people excited to see your emails in their inbox, or sky-high unsubscribe and churn rates.

## The rules for LII (Least Inbox Interruption)

“Space in my email inbox is space in my brain, and that's precious to me,” wrote Hacker News user NoraCodes in 

a thread about unsolicited emails to developers

But it’s not that all emails are unwanted. Sometimes you want things to take up space in your brain. When X/Twitter 

restricted its GET following/followers endpoint

 to the Enterprise plan in June 2023 without letting anyone know in advance, developers were enraged. “Is this some kind of joke?,” asked one, rhetorically. “I’ve never seen anything like this before,” said another; “not sure what to tell clients.”

One suspects the 60+ developers who commented would have appreciated an email about the breaking change, ideally one sent far enough in advance to plan mitigation.

Those same developers, though, would likely be the first to unsubscribe from the platform’s default “Things you missed since you last logged into X” email. They might even be annoyed if X sent them a developer-focused email without their opting into it first, or emailed daily about API features even after opting into a list.

Least inbox interruption. That should be the goal. People are glad to be interrupted by an email when it warns them of or prevents a far larger interruption. They’re generally glad to receive messages that make them more productive, if they opted in. And they’re annoyed—or worse—when they are interrupted by irrelevant emails when it’s least convenient.

That leads to three rules for developer email (that, honestly, apply to everyone):

## 1. Don’t auto-add people to email lists when they sign up for an app

The temptation’s high to opt everyone into everything. To leave the “subscribe to our emails” box checked when people sign up for your app. Don’t do that.

Even onboarding messages should be kept to a minimum, focused on the customer rather than your company’s success. “Inbound communication seems very heavily geared towards benefiting the company ... as opposed to being actually necessary or useful from the point of a customer,” 

 on Hacker News. “These thoroughly annoy me.”

Don’t auto-subscribe every signup to your email list. Only send onboarding emails in extreme moderation. Otherwise, there’s a chance developers will think the same as the replier to that comment, fairly or not: “That's what the spam button is for.”

Some emails you’ll have to send: Account verification, payment notices, and other critical communications. You may need to message about things that will affect users, including downtimes or breaking changes. And you’ll want to tell users about things you’re excited about, including new versions and promotions.

Applying the principle of least inbox interruption and audit messages to ensure they’re truly necessary. Email verification, yes. Welcome email, possibly not. Then sort messages if they’re most likely useful to an average user or a developer, if your product encompasses multiple audiences. Developers will want downtime notices, while they’re perhaps less likely to appreciate discounts. If someone signs up from your API page—or ever enables it on their account—opt them into your critical notices list (in Buttondown, you could do that by 

). If they sign up from your standard pricing page and use more business-focused features, perhaps you’re safe sending feature and promotion details.

## 2. Let people opt into emails they want to receive

Then, for all other communications, let customers choose the emails they want to receive.

When you let people opt-in to certain segments, you’re also giving them the agency to opt-out of those segments without unsubscribing completely.

Take your blog, for instance. Some companies split out their developer and general interest content into separate blogs (or even, Microsoft MSDN-style, make blogs for each product and technology). Others keep content combined but separate it by tag.

Either way you organize content, use that as a way to split your newsletter into segments. Click a developer-focused Twilio blog post, and you’re invited to sign up for a “Developer Digest.” Business and general interest posts show a “Digital Dispatch” list subscription instead. They could subscribe to everything, or nothing, or something in-between. Their choice.

Give people a milder way to subscribe, even, so only those who truly want to be emailed sign up. Tailscale blog’s signup form says “Too much email?” underneath, with links to RSS and X in case you want to follow the blog but aren’t as keen about filling up your inbox.

The more focused the email list, the better. Uptime blogs, for example, are most commonly hosted on a 3rd party service, with a 

 URL and an email list specifically for downtime alerts. That’s critical for reliability, so the core service going down doesn’t take the status page with it. But it’s also a helpful blueprint for thinking about developer-focused emails.

Have different newsletter segments for API changes and product features, perhaps. Include them in your settings, with clear differentiation between each email. Linear, for instance, lets you opt into changelog and DPA agreements, while auto-adding you to privacy and legal updates they’re required to send. Tailscale goes further, with separate email fields for each type of email, so developers can get security and configuration emails in their inbox, while sending account change notifications to a PM and billing emails to accounting automatically. Put the power in the customer’s hand.

With opt-in subscriptions, they can choose which emails they want to receive, and how they read them. Perhaps they’d rather sign up for your service with their primary email address, while following your blog with a personal email they check when they have time. Maybe they want a unique subset of your emails, instead of everything. They’re more likely to stay subscribed, and less likely to resent your messages, if they’ve customized subscriptions down to exactly what they want.

Then, if they unsubscribe, let them go. Don’t make them jump through loops, or keep them unsubscribed to segments they’re unaware they’re in. You’re more likely to win them back over time through your product, and more likely to anger them into churning entirely if you email after they subscribe.

## 3. Only send emails the receiver will appreciate

You’ve carefully built out email segments specifically for developers, let them opt into exactly what they want to receive, and made it easy to unsubscribe.

It’s a recipe for an engaged newsletter audience, if you can keep it.

“If a company that I'm interested in sends me an email once per month, then I generally don't mind it. I might even appreciate it,” 

 in a discussion about emails. “Send it every two weeks, and you're training me to tune out. Send it weekly, and you've irritated me enough to have the motivation to unsubscribe.”

Everyone’s different, but Steve has a point. Even your fans only want to hear from you so often. Twilio promises a monthly email, no more. At Buttondown, we keep our email updates to the same timeframe. A more general-interest newsletter, or a paid subscription, might be something you want to read more often. SaaS and API updates, though, aren’t something you want to read every day. You could restrict your newsletter to once per month and inform subscribers of the schedule when they sign up. Or, you could use tags to 

segment your list by how often people want to hear from you

Format matters too. GraphCMS found their ideal format after experimenting: New features listed in a nearly plain HTML email, with “no case studies, no sales CTAs, no upsells, no discounts, no fluff.” That led to consistent “40%+ open rates and 15%+ click rates,” along with substantive replies, something their more formatted emails never had. A plain Gmail email-style template might be best (like Buttondown’s default).

So does focus. You could send that monthly update email to everyone. Or, you could have your product send an API call to add a tag to newsletter subscribers if they use a feature—then skip reminding those people, since they’re already actively using it. They’ll never know you’re looking out for the space in their brain, but they’ll quietly appreciate it by staying subscribed.

After the hard work of segmenting developers into separate lists, writing emails focused on their needs, and making them opt-in only, you’ll still need to check your emails. Buttondown runs through 

 every time before you send emails, checking for broken links, overly large images, missing attachments, and so on. You then need to 

 to ensure your messages strike the right balance of helpfulness without being overly salesy to prevent marketing creep in your emails.

One opt-in subscription and one email that delivers far more value than it requests at a time, and developers will start looking forward to seeing your name pop up in their inbox. They’ll know they can ramp up or down the emails they receive from you as they want, building trust in your company and emails alike.

Always remember: Very carefully subscribe people to your email lists. Very liberally unsubscribe them, too. That’s the formula for a happy—if smaller—email audience, developers and general public alike.

Developers want news from your product (sparingly).

The principle of LII

 to keep Buttondown running and sending your emails. Plus another 

 (and the 10% of our revenue we donate to them) to power our codebase—not to mention the hundreds of other open source projects behind the SaaS services powering Buttondown.

Buttondown sits on the shoulders of giants. So does every single software project—and nearly every human endeavor.

“We see more and farther than our predecessors, not because we have keener vision or greater height, but because we are lifted up and borne aloft on their gigantic stature,” one 

 is said to have quipped nearly a thousand years ago. It’s the snowballing effect of generational knowledge that took humanity from the first transistor to the Frontier supercomputer and its 1.102 exaFLOPS of computing power in 75 years. Someone figures out how to switch electronic signals, another how to etch that into silicon, and a million trial and errors later humanity has LLMs running in their pockets.

Sometimes it’s the hard-won lessons that guide our intuition into the next great discovery. We don’t have to reinvent the wheel; we can innovate on top of it. Sometimes it’s just in knowing that something’s achievable, the “adjacent possible,” 

as Farnam Street quotes scientist Stuart Kauffman

. No human in recorded history had run a 4 minute mile until Roger Bannister did in 1954—and today, that time is now run by virtually every state-level-best high school cross-country runner.

Once you’ve done something with that knowledge, with that framework and foundation undergirding your work, it’s worth giving those whose shoulders you’re standing on a shout out.

I couldn’t have built Buttondown without Ray Tomlinson sending the first email over ARPANET in 1971. And I couldn’t have built it as easily without Mailgun’s email delivery service. 

Every bit of software is a story of interdependence, all the way back to the first version of Linux. “Sadly, a kernel by itself gets you nowhere,” lamented Linus Torvalds after painstakingly writing his 0.0.1 Linux kernel in 1991, before recommending the GNU shell and compilers and detailing how the Intel 386 CPU made that first version possible. Fast forward several decades, and a modern Linux install will come with thousands of packages, built and maintained by an army of developers.

Open source, perhaps thanks to its academic roots, has a strong tradition of attribution. One forks a project, the new iteration takes on a life of its own, until someone repeats the process. Thus the KDP project’s HTML Widget got turned into a browser engine, KHTML, which Apple then forked into Webkit to power Safari, which Google then forked into Blink to power Chrome, which Microsoft then used to build Edge, and a bit of code committed in 1998 dictates the design choices of web developers in 2024.

At one level, it’s a cool historical footnote, like the knowledge that we’re made of the dust of the big bang. But at another level, it’s a reminder to share the love, and show the next generation of developers how they, too, could pull such things off.

New products, so often, start off as a tinkerer’s paradise. You can take an Army Jeep down to its bolts and put it back together again, learning what makes it tick along the way. Then, products gain sophistication and polish, then go mainstream, the innards hidden behind 

 stickers. Good luck taking apart a modern EV.

Same for PCs—modular, then streamlined into a thin aluminum wedge. Same for software—remember dropping into DOS mode, or hex editing files?

The web is one of tech’s remaining bastions of openness. Sure, it’s increasingly hard to know how sites work, with obfuscated code and web services running behind the scenes, but you can still Inspect Element and see what font was used for a site’s headings or infer if it’s powered by WordPress. You can get a bit further with Chrome extensions like WhatRuns, Wappalyzer, or BuiltWith which can tell you that a site is powered by Next.js, uses Cloudflare’s CDN, and Stripe for payments. Enough to get a budding web developer started, anyhow.

You’ll have to share your stack, manually, to give them any more clues.

There’s a fun tradition on the web of sharing how a site is built. Like the colophon in a book, with publisher and typesetting info, an About or What I Use page can shed light on how one built this particular site.

Rewind AI Co-Founder and former Twitter designer Paul Stamatiou maintains both a 

 page with everything from displays to his email client, and an 

 page detailing his Jekyll setup. Founder and author Derek Sivers maintains a more minimal 

 page, featuring his camera, keyboard, and car. And the 

 blog, perhaps most famously, includes well over a thousand interviews featuring hardware, software, and ideal setups from everyone from 

. It’s good fun, but also insightful to see the choices that go into each creator’s setup, the slight differences that make all the difference.

The project-level version of those pages are even more impactful. 

 features the tech behind everything from the New York Times to Facebook and Shopify, ideally helping you see which teams are using Typescript or AWS Lambda. And if there’s enough interest in stacks to make StackShare an acquisition target, there’s plenty of interest in you and your team sharing your stack.

So, start by listing your stack. It could be a blog post, or an addendum to your About page.

You could list the services you use, like 

 page listing every paid service we use—inspired by freelancer tracking app 

 page. That could give the next generation of founders both ideas on how to build, and an estimate for their expected burn rate.

Then, you could also build out your open source stack, like 

 page, listing the packages and projects that made your tool possible. And, if possible, you could use that as a chance to give back, as Buttondown does along with Sentry, Spotify, Vercel, and more in the 

 project. Or you could give back in kind, contributing upstream to their projects or building add-on packages that you, in turn, give back—something else we do, with our Tiptap extensions for 

, among other projects. And if your project 

 open source with direct contributions from others—or if you’ve pulled in beta testers to help make your project possible—credit them as well to share the love.

“Err on the side of giving props liberally,” says the 

WordPress Core contributor attribution guide

. That matters, for those who contribute code and those who made your contributions possible, alike. Apple does it. Meta, as well. Startups, though, tend to do it the best. You’re building the product, you’re making the stack calls, so your endorsement rings even stronger.

Then build on that. Write in your developer newsletter about your decision process, why you use the tools you do, and how you’ve solved problems and built your product with them. Mention in your 

 when you’ve added something new to your stack. Give the team a shout-out on your favorite social media when they come to the rescue. And keep your stack updated, as things change over time (perhaps saving the old choices for the record, so people can trace the roots of how your current stack took shape).

There’s the benefit of openness. Want developers to use your product—or consider joining your team? Make sure they think you’re building on a cool stack, and solving interesting problems instead of reinventing the wheel.

There’s also the benefit of trust. We were more likely to trust new PC OEMs when we knew they were built with components we trusted from Intel and Nvidia. The 

 leans into that, listing the cloud services and specific data sent to them. You might not trust Arc yet, but you might already trust Google Firebase, and the trust trickles down.

And, perhaps most beneficial, there’s the benefit of community. Publish what your product is built on, then share that page with the services and project maintainers you featured. Thank them. You might make a new connection, might get a bit of reciprocity if they feature your product, might just get warm fuzzies out of the interaction. It’s all worth it, in the end.

started a soliloquy Steve Jobs emailed himself

 in 2010. “I did not invent the transistor, the microprocessor, object oriented programming, or most of the technology I work with.”

“I love and admire my species, living and dead, and am totally dependent on them for my life and well being,” he concluded.

Jobs was many things, but not known for humility, nor for sharing the spotlight. Yet here, through a crack in the façade, shined a glimmer of respect for the ideas and inventions he’d spent his life perfecting.

Gratitude’s part of it, but so is curiosity. I love seeing behind the scenes of my favorite projects, and have a child’s curiosity at construction sites and factory tours. Does it matter that your project used SES to send emails, and how you solved some obscure problem that only a handful of us would even know existed? Will I care, and be more likely to read your writeup? Absolutely.

It just might be the thing that makes me remember your project, think of it the next time I need to add a tool to my stack or build in a new integration.

It’s my favorite developer marketing—because it’s marketing for the other tools, and who doesn’t like someone who’s always praising their friends?

The best developer marketing might be to show how they, too, could build what you did.

Compliment your complements

Six words are all it took to run Southwest Airlines, according to CEO Herb Kelleher. “We are THE low-fare airline. Once you understand that fact, you can make any decision about this company’s future as well as I can,” he said. 

“Imagine Tracy from Marketing comes into your office. She says her surveys indicate that passengers might enjoy a light entree on the Houston to Las Vegas flight…she thinks a chicken Caesar salad would be popular. What do you say?” Kelleher would wait for an answer before continuing “You say, “Tracy, will adding that salad make us THE low-fare airline? No. We’re not serving any damn chicken salad.” An MBA in a single sentence. 

Herb’s North Star for Southwest wasn’t the sexiest, or cleverest, or even the most original. Just like Polaris isn’t the brightest star in the night sky. No, the real function of a North Star is that its position remains mostly stable amidst a constantly shifting canvas of (sometimes brighter) stars. Consistency is gold.

For newsletter creators, having a fixed point on the horizon is a filtering function. If there’s a straight line from a topic you want to write about to your North Star, draft it. If it’s a detour, a meandering stroll, avoid it like a chicken salad on a cheap flight to Vegas. That’s easier said than done.

Writers are so close to the source material, steeped and stewed in the details, that it’s hard for them to take a step back and see the forest for the trees. They get distracted, diving into rabbit holes and pulling on threads that lead themselves and their readers away from the anchor point. As passages become less meaningful, the writer loses motivation to keep going and readers lose interest.

Made to Stick: Why Some Ideas Survive and Others Die

, brothers Dan and Cheap Heath highlight the story of 

, a city newspaper that slowly became more and more focused on state and national news. That was, as the reporters of the time thought, where the most interesting topics were. But the paper’s owner disagreed.

“All of us know that the main reason anyone reads a local newspaper is for local names and pictures. That’s the one thing we can do better than anybody else. And that’s the thing our readers can’t get anywhere else,” Hoover Adams wrote to his staff. 

On another occasion, he doubled down, “If an atomic bomb fell on Raleigh, it wouldn’t be news in our town unless some of the debris and ashes fell here.” There was zero ambiguity about what he wanted from his staff. Everyone knew how to make the “right” decision, and that was reflected in the paper’s circulation numbers.

The number of subscribers to Adams’s local paper was 112% that of the local population. As the Heath brothers point out, that means that people outside of his small town were buying the small-town paper and/or households were purchasing multiple issues. Either way, the paper’s singular focus and format attracted and retained subscribers.

The internet magnified the potential upside of forced prioritization tenfold. Writing about the growth of his email newsletter, 

 “The more precise and niche the words I input, the better the internet would match me with people I could forge meaningful relationships with. Writing for the general public, you need to be broad and a bit bland. I didn’t want a general public. I wanted a specific set of people, the people who could help me along as a human being obsessed with certain intellectual problems. I didn’t know who these people were. Hence my writing was a search query. It needed to be phrased in such a way that it found these people and, if necessary, filtered others.”

In this way, identifying your North Star and locking yourself into its path becomes a virtuous cycle. It keeps you on topic, which catches the attention of people interested in that topic, which validates work on said topic, and reinforces focus on it. It worked for Southwest, 

, and countless niche newsletters like Karlsson’s 

For a singular focus to be sustainable and marketable, it must be declared and circumscribed. It should take almost zero cognitive power to decide what falls inside or outside of the quest. The chicken salad would have raised Southwest’s costs. Reporting on a story from the next town over would have meant fewer local names in 

. Bland writing would bore Karlsson’s subscribers. 

It’s rare to get it right on the first try. You might write a handful of newsletters that you hold off on publishing, waiting until you can distill what unifies them into a succinct, precise statement. In 

, the authors recommend starting with a “Hollywood Pitch” formula, anchoring a new idea to pre-existing ones. 

 was “Jaws in space.” “My email newsletter is like X but [for/about] Y.”

Then, put it on the Newsletter page of your website, your social media profiles, the introduction of your book, anywhere that will set people’s expectations and get them excited. Or filter them out early. Buttondown user 

 that their work “focuses on uplifting fat, disabled, queer, and trans people.” That’s a North Star! Through that lens, there’s no way to be confused about which topics work and which don’t, what subscribers will like and what they won’t. All you have to do is keep marching in that direction.

The single most important thing for any email newsletter to succeed is a North Star. With one short sentence, it answers tricky questions about what to work on or prioritize today and far into the future. It tells subscribers who you are and what you’re about. It filters out bad ideas and busywork, detractors and distractions, so all that’s left is work that matters to you and those you want to collaborate with. 

Yours could be as simple as promoting your work. Not everything needs to be thought-provoking and novel. But it must be focused, purposeful, and 

. There is no (worthwhile) North Star that demands that you send an email just to maintain an exact cadence. Leave rote, robotic writing to AI. You’re searching for a different kind of reader.  

As Karlsson wrote, “It turns out that if you’ve written something that you find interesting, it is not unlikely that people you like will find it interesting too, and pass it on if you give them the chance.” 

And for people like you to find you, it’s best to stick to a fixed path.

A lodestar makes it easier for people to find you, follow you, and share your work.

What's your newsletter's North Star?

Jane Friedman tries to send an issue of her author newsletter every two weeks or so. And after 15 years of watching the numbers, she's found even that is sometimes infrequent enough for people who just signed up to forget who she is by the time her next issue lands in their inboxes. Her solution is what she calls an autoresponder.

Others might call it an “email automation,” “drip campaign,” or “welcome sequence,” but they’re all (horribly named, for one, but also) the same thing. In 

, it’s three emails sent to new subscribers over 10 days to “introduce people to some of the most key posts and information I make available for free.” 

, and you’ll see something similar. Her signup confirmation tells you to expect “a quick series of getting-to-know-me emails over the next week or so, starting tomorrow.” 

There are many different ways to design a series of emails that are automatically sent in response to specific events. You might 

 to new signups or celebrate when subscribers hit their one-year anniversaries. All that matters is that you create automated campaigns that further your relationships with readers and minimize marketing busywork.

Most newsletter platforms include an option to send a welcome email after someone signs up or confirms a subscription. But that’s a single email that goes out immediately. Like Friedman, you may want multiple welcome emails sent out over days or weeks to familiarize people with your writing.

Another reason to create a multi-message welcome sequence might be a “graduation series” similar to the one 

indie sci-fi author Matthew Buza describes

 as “a way to move a person from [my autoresponder] into my main list, but only people who have graduated through my autoresponder.” That way, subscribers only start receiving your regular newsletter after more important introduction emails. For Buza, “The sole goal of the autoresponder is to get the new reader to buy one of my books, leave a review, and opt into my Advanced Review Copy team.”

You could build that in Buttondown in a few minutes (or, if you aren’t on Buttondown’s $29/month tier, play with automations at 

). First, make sure to turn off any default welcome email. Then, open your automations builder and set the trigger to any time a subscriber confirms their subscription. Choose whether you want the action to take place immediately or after a delay, set the action to send an email, and write your first message.

Using the same trigger but with longer delay times, you might draft a graduation series with emails on days one, four, and nine after someone confirms their subscription. 

You'd need a way to differentiate subscribers who have and haven't gone through the graduation series. Tags are perfect for this. After the final welcome email on day nine, create an automation that's triggered by a signup confirmation, waits 10 days, and then applies a tag (e.g., Graduated) as the action. When you want to send newsletters that only go to people who've gone through the entire series, send only to subscribers with the Graduated tag.

That’s only the beginning (literally). You can create similar campaigns where templated emails “drip” out at predetermined intervals for anything that fits within the triggers and actions available to you.

Now, let’s say you have a few hundred subscribers who had signed up before you set up your welcome series. All you have are their email addresses and, if you’re lucky, their first names. Whomp whomp. The best way to start (ethically!) gathering more data on subscribers in this situation might be an automation triggered when readers click a link or 

Professional writers, for example, might poll readers about their favorite fiction genre or non-fiction topic. Assuming you have 

 turned on, you’d set up an automation triggered by a subscriber clicking a link or a survey in your newsletter and set the action to add tag (e.g., reads-urban-fantasy or likes-popscience).

Adding the details to subscriber profiles alone would be enough to inform more targeted launch emails and promotions. But you could take it even further by putting together sequences that fire off whenever a specific tag is added. Maybe you want to automatically send a list of your favorite books in a subgenre (possibly mentioning a fellow author as part of a 

) or link to all your articles and books relevant to a subscriber’s favorite non-fiction topic. 

Using automations to segment your list is a fantastic way to make newsletters more personal and valuable for individual readers without a ton of manual work on your part. What’s more, you can use the same basic flow to keep your newsletter’s performance stats above average and your monthly costs low.

Spammers have made newslettering much harder for the rest of us. They spend so much time finding ways to get around blockers and filters that email providers like Google are constantly upping the threshold for what they deem a good-faith sender. If you want to avoid your subscribers’ spam folders, your open and click rates need to be high, and your unsubscribes need to be low. 

One way to be proactive about that is with a re-engagement series. Once or twice a year, you’d filter your subscribers list to only show people who have been subscribed for at least three months but haven’t opened anything during that time. These are the people at risk of hurting your stats.

 a “List cull every six months. No good paying for subscribers on your list who don’t add value—but you need to give it a few months for them to demonstrate a clear pattern of not interacting with your content.”

With the sorted and filtered, you could create an Unengaged tag, and bulk add it to anyone who stopped engaging. 

At this point, you set a trigger for any time the unengaged tag is added, with an action to send an email. The first message would say something along the lines of “Hey, it looks like you haven’t been opening the newsletter recently, although that may be because you’re blocking trackers, which I totally respect. Since I don’t want to clog up people’s inboxes with emails they’re not opening, I periodically remove anyone from my list who is unengaged. So, if you want to keep receiving my emails, click this link or reply to this email, and I’ll keep you on the list and respect your tracking preferences going forward. Thanks!”

Next up, an automation that removes the unengaged tag from anyone who clicks the link or replies directly. And two more time-delayed reminders sent to anyone with the unengaged tag who didn’t click the link or reply, capped off with a final automation that ends in the 

 action for anyone who never engaged with the series. Bingo, bango, bongo, cleaner, higher-performing lists after a few minutes of bulk tagging.

marketing yourself is a marathon, not a sprint

. It should be challenging but not unbearable; uncomfortable but never all-encompassing. One of the best ways to manage that balance as more and more people begin following your work is with a newsletter that expands your reach without dehumanizing your brand. 

Autoresponders are as helpful for that as their moniker is off-putting, especially for professional writers and solopreneurs. They help you deliver timely, relevant welcome messages, personalized recommendations and offers, and polite-as-can-be breakup emails–all while you focus entirely on your novel, blog, journalism, or whatever wonderful thing you’re drafting.

Welcome, segment, and unsubscribe readers with email sequences personalized to subscriber actions

Where to start with newsletter automations

A newsletter subscriber is worth 10x more than a website visitor. You have no way to tell a website visitor anything after they've left your site. No way to show them your newest project or announce a special discount. Unless you use (shudder) retargeting ads. When someone gives you their email address, though, that’s a commitment to listen.

Years before Ryan Holiday published his first bestseller, he had a newsletter. It started with 50 friends before exploding to 250,000 subscribers a few years later. Writing about that journey, 

 “Building an email list is the single best way to communicate with your audience, period. Better than Facebook, better than Twitter, better than ads. Because you own it. …no one can get in the way.”

Some of the list’s growth was thanks to a single line at the bottom of emails encouraging people to forward to them their friends. But signups through Holiday’s website were always the best way to establish “a relationship of mutual trust and opt-ins.” And as long as you have something worth saying or selling, the same goes for your site.

Everyone with a website and an email newsletter needs a signup form for the latter on every page of the former. Full stop. On the homepage, the form should be above the fold, visible before visitors begin scrolling. This is true for anyone with a personal website, from software developers to self-published authors to 

“Hi! I’m Cassidy, and I like to make memes and dreams and software! I’m a startup advisor and investor, developer experience expert, open source-er, and meme-maker on the internet. I enjoy building mechanical keyboards, playing music, hanging out with my family and friends, and teaching in my free time. You should subscribe to my newsletter.”

The signup invitation is high on the page but, crucially, after she introduces herself.

, describing his expertise before asking for the signup:

*“Hello, I’m Elliot—a designer, author, and typography enthusiast. You might know my work with Google Fonts & Adobe Fonts, or the magazines 8 Faces & Lagom. Sign up to my newsletter.”

He doesn’t stop there. Elliot also has a newsletter signup form above the fold on 

 page of his website. His portfolio page. Blog. Contact and About me pages. The page dedicated to his podcast and his masterclass. Every one of them.

The goal isn’t so much to get people to sign up as soon as possible. Not many folks would sign up for 

 (I’m down if you are, Netflix). They first want to vet creators before giving them a coveted spot in their inbox. Instead, the idea of Ask Early, Ask Often is making sure that there’s always a signup form in sight, no matter what page they’re on, the moment they’re ready.

Make the forms on your homepage and elsewhere small and unobtrusive. A single email field if you can manage it, 

 including spots for first and last names. That should be low-profile enough to avoid annoying site visitors jumping around from page to page.

Ideally, each form would also have its own ID, allowing you to track where each signup came from. You might find that one page is responsible for the lion’s share of submissions and replicate whatever makes it better than the rest.

If website visitors are worried that your emails are all desperate pleas to buybuybuy or navel-gazing introspections, they’re not going to sign up via the minimalist forms on your homepage et al. They need assurances (and corgi photos).

Ryan Holiday always had a page on his site outlining the newsletter. But it wasn’t doing much heavy lifting until he gave it a facelift, adding “a clear explanation of what the list was, why people should sign up and what they’d get out of it. It [did] wonders for the number of new subscribers.” All it took was a few lines about the newsletter cadence, contents, and commitments to readers.

For instance, every email from Cassidy Williams includes an 

, which she explains on her newsletter details page. Below that she promises not to spam subscribers’ inboxes and links to an archive of previous newsletters. In less than 100 words, she gives website visitors everything they need to decide whether or not to join the list.

Below the context and details of what to expect, you might include a nod to the people who love your emails. On author and photographer 

 section does double duty as evidence of the newsletter’s popularity and descriptions of Mod’s style and tone. It’s often called “social proof” and can also come in the form of subscriber totals or average subscription length. Anything that establishes credibility and makes a signup feel less risky.

Then, a newsletter details page needs a signup form. Although not necessarily the same one you use elsewhere. Visitors who made it to this page are less likely to be put off by a form (what else did they think they’d find?). So you might add fields that ask subscribers to indicate their preferences and 

automatically add tags based on their answers

. That would help you segment your list, sure, but also reinforce the personalization and specificity of what’s on offer.

An author, for example, might ask subscribers if they want bi-weekly book updates or less frequent book launch emails. Or if they only want emails about a specific series, genre, or character. Seeing the thing they want listed as an option makes the form that much easier to fill out.

At the end of the day, every page of your website should carefully encourage visitors to sign up for your newsletter. For the people who are interested but unconvinced, you have a newsletter landing page with all of the details they might want.

Now matter how much urgency you inject into your website’s language, some people just aren’t ready to “Sign up now” or “Join today”. So give them an option with less commitment. Link to a video or PDF excerpt from a course or a book you’re selling, no email signup required, with a reminder about the newsletter tagged onto the end. Or invite visitors to sign up for a series of five automated weekly emails with a promise to stop there unless they opt for more. They aren’t committing to anything long term, and yet they haven’t walked away entirely. Something for everyone!

Like most self-promotion projects, “get more newsletter signups from website,” can seem pretty straightforward before unraveling into an open-ended, neverending mess. There are countless ways you could go about it. First, focus solely on making sure every page of your site has a signup form. Nothing fancy, just Name, Email, and a Subscribe button.

On the homepage and anywhere else that makes sense, toss in a 1-2 sentence pitch just above the form.

Next, create a dedicated newsletter page with 100-200 words worth of details about the newsletter, and a form that has a few get-to-know-you questions.

Finally, add some free ungated (i.e., not behind a form) resources (book excerpts, video explainers, infographic cheatsheets, etc.) and slap a link to your newsletter on the final pages.

All that, plus a few pictures of your dog, will almost certainly move the needle.

Image Credit: Header photo by Bri Tucker via

Provide more opportunities to sign up, more details for people who want them, and reminders for folks who aren't ready to sign up