This is our very first newsletter deep-dive and I thought there would be nothing better than sharing the entire process of how I built, tested, and launched a new email newsletter from the ground-up.
I’ll cover these topics, in general:
- Is a Newsletter Worth It in 2020?
- When Should I Start a Newsletter?
- What is My Optimal Newsletter Stack?
- A Content & Publishing Workflow for Newbies
- How to Test-Drive It and Launch
- Final Considerations and Thoughts
My hope and goal is simple: To demystify the process of creating a simple and effective email newsletter from scratch!
To infinity & community,
Is a Newsletter Worth the Effort?
If you’re even asking, then, this issue might not be for you! But, the short answer is a resounding and definitive “YES!” as they’ve proven to create a positive and high-ROI throughput for any business of any size, in both online and offline-centric companies.
Personally-speaking, this newsletter @ YEN.FM is one of a dozen email newsletters I’ve built and managed over the years and I currently have nearly
19,000 folks subscribed to a weekly newsletter that once started as a personal email to a small group of friends!
And this leads me to the most important piece of advice that I can give you as you embark on building a newsletter (and community of happy readers) that you can be super-proud of: Consistency is everything.
Once you start you must not stop until you’ve sufficiently exhausted your attempt and are clearly not seeing the results that you want. And a “reasonable” amount of time is, at the very least, 6-months, but I coach startup founders and business owners to give it, realistically, a full year.
The reason is because a newsletter is nothing more than a channel of communication between you and a willing reader. It is, essentially, a relationship and your singular mission is to deliver value in every issue that you publish.
In this way you’ll build the currency of
trust with them and you’ll “earn the right” to share with them your business, at the right time and in the right way. In fact, the best newsletters never sell anything directly.
With all of that being said, a newsletter is a powerful relationship and community-building tool that, when built and operated properly, can be an absolute boon to your brand and business.
When Should I Start a Newsletter?
Today. Immediately; without hesitation. Even and especially if you’re not entirely sure what you’re going to be writing about. The reason is both strategic and tactical:
- The vast majority of businesses do not use newsletters as a part of their core customer and community-building strategy. Statistically-speaking, the fact that you’re operating one at all makes you more competitive as a business and venture out of the gate. As a small business, brand, or creator, you have to use every piece of ammunition that you can to not just survive, but thrive.
- Building a newsletter is nothing more than
writingand most of us really suck at writing. I mean, terribly-so. More specifically, most of us are not used to writing consistently in thematic prose to a growing, curated audience. Practically-speaking, it’s going to take time to learn how to “write a gud and ahsome newsletter” and build a publishing cadence that works for you.
You see, this is about “reps in the gym,” so to speak. It’s about getting in as much practice as you possibly can and learning the fine art and science of newsletter writing which, as I’ve already said, is foreign to most of us.
Consequently, the sooner you start the better. And this post is here to help!
My Optimal Newsletter Stack
I am primarily using two tools with the following, high-level motivations:
- WordPress — For content ownership and landing page (
- Substack — For subscription management and content delivery (
The reasons I use these technologies in-tandem is because newsletter tools have come and gone (remember: I’ve been around for a while!) and being stranded on a dead platform is something you’ll never want to experience first-hand; trust me on that.
A self-hosted WordPress site / blog allows me to duplicate any of the content that I create for the newsletter into a system that I completely control — this reduces my risk of being de-platformed to effectively
zero percent. I will always retain control of the canonical issue. And, to be honest, it just makes smart business sense.
WordPress could be also used as a content delivery system but Substack has a better member management system and is going to be more trusted than a random (and young) domain name. This is important because you don’t want your email updates going into people’s
spam folders and using existing platform like Substack and MailChimp reduce this risk significantly.
Using both WordPress and Substack increases your baseline (marketing) surface area which is always good for business, especially if you’re an early-stage project that’s just trying to get off the ground. There are natural
SEO benefits too, especially if you’re using WordPress as it’s been generally-optimized with search engines in-mind. Adding an SEO plugin can boost this significantly (I share that in just a sec).
🛑 — SUPER HACK: Oh, I almost forgot! You can literally copy-paste what you write in your WordPress editor directly into Substack’s editor with very little need for fixes or adjustments, thus saving me a ton of time on formatting and publishing the content.
Note: If you’re not interested in using WordPress then you can use Substack by itself and do just fine and their export settings are available for future migration or transfer needs.
A few more WordPress-specific tidbits that can help you optimize your installation and setup might be the fact that I’m only usingtwo plugins: Jetpack and Yoast SEO — I walk through their onboarding workflows and turn-on the following settings for Jetpack:
I’m also using a free theme with a few slight, manual modifications. No need to pay out of pocket for a “premium” theme.
I’m self-hosting on WPEngine but there are many other cheap options. You could even use WordPress.com and pay a little more for their domain registration service.
I use IWantMyName.com for domain registration (
http://yen.fm) which I then change the DNS zone file to point a A Record / CNAME to WPEngine.
WordPress / Jetpack have a built-in submission form that you can see in action here. Use this to get feedback, collect emails, connect with readers, create submission forms and more. Entirely free, mind-blown.
You’ll want to make sure turn on “pretty permalinks” as well via settings. I choose
/%postname%/ for the best results.
And that’s about it! You can get through most of this in less than an hour if you have most of the biggest parts already available, like hosting and DNS.
In terms of Substack, here are my settings and top-line considerations:
Make sure you go through most of the settings and edit your title, sub-title / description, tags, as well as update the “About” and “Thank You” page. You will spend most of your time on those pages, without question:
You can, of course, use some of the default settings but that won’t make your newsletter standout. Please don’t forget your
Preamble setting (I customized an image which really makes the delivery standout):
Finally, make sure to turn on all of your notifications, especially the
email signup which will give you a chance to really make a killer first-impression:
With that, you should be setup to mirror most of what I’ve been able to put together in just a few hours!
Building a Publication Workflow That Won’t Burn You Out
Writing, as I’ve already mentioned, is hard. Writing a newsletter for a growing audience is even harder. That’s why we need to keep things super-simple in the beginning and learn-as-we-go!
Remember, “bad is where you start” whenever you try something new so the goal is to “get the jitters” out of the way as fast as we can and get our first, few publications in the proverbial can!
Meaning, we want to start publishing something right away.
Here’s what I suggest for newbie newsletter builders, in just 10-steps:
- Commit to one issue a week, that’s 4 a month.
- Choose a specific day.
- Choose a specific hour to publish the newsletter (i.e. a “deadline”).
- Schedule in time during the week to write the content, a specific day and hour and amount of time; I suggest an 40-60 minutes.
- Commit to a specific size / length, like 200-400 words per issue, not including the “header” or “footer” content blocks / areas.
- Choose one topic or theme, test-drive that topic for 4 weeks.
- After 4 weeks, decide to continue with that topic and/or theme or change it to another topic. This goes without saying, but, you should choose a topic that’s strongly-related to your business or brand or industry.
- Repeat this 6 times (yes, that for 6 months). You’ll have published 24 times in total and should have a very healthy amount of data via Substack and WordPress / Jetpack’s built-in analytics.
- Evaluate the data and decide to either continue or stop the experiment.
- If you don’t use WordPress, then the total cost of ownership is $0.00.
The key things to recognize here is that most-everything is quantifiable so you can discern the value over the select period of time. This also helps you work through “writer’s block” and other psychological impairments that will attack you the moment you sit down to write — trust me, I know!
I can’t stress this enough: Keep it simple. Keep it doable. Burning out on writing a newsletter is how most newsletters die (besides abandonment). You can always add more issues to your line-up later, after you feel comfortable with your cadence, workflow, and schedule.
From a reader’s perspective, this is about one thing:
trust. How do you build that? Two ways: Consistent content and content that is consistently valuable and useful. That’s really it. If you do that then you win. Literally, the so-called “formula” is that simple.
The goal of the 10-steps for newbies is to help build muscle-memory and the basic foundation of a consistent writing habit and schedule. Don’t over-engineer the “content strategy” or go too far on “optimization” — you’ll pick these things up as you grow as a publisher.
Now, if this isn’t your first “rodeo” then here’s what I’ve committed to for YEN.FM as a more sophisticated operation:
- 5 issues per week covering a very specific topical cadence which you can find on the About Page.
- Since I am writing every single business day I have calendared in dedicated writing time in the morning and early-afternoons. Monday and Friday take 1-3 hours as they are longer-form while Tuesday-Thursdays require less than 60 minutes (is the goal). Just think about this for a moment: I’m willing to commit up to 25% of my working week (10+ hours) to this experiment! But, that’s how much I believe in it’s effectiveness!
- I’ve committed to do this for 6 months and my goals are 100 subscribers by November 1, 300 subscribers by December 1, and 1,000+ by January 1, 2021. I will adjust these goals by mid-experiment.
- I’ve added the Substack widget into my landing page’s design for always-available sign-up:
All-in-all, the total cost of ownership is approximately $99 / year for domain registration plus ~$300 per year for WordPress hosting. Most publishers will not need this level of service or size and you can get much-cheaper hosting and domain services elsewhere.
How to Test-Drive and Launch Your Newsletter
One of the best ways to test-drive your newsletter is to literally test-drive your newsletter with affiliate subscribers. In other words, test-drive your newsletter with friends, family, and folks that you already know that can give you useful feedback on the first few issues.
The following is how I went about my “soft-launch” for YEN.FM.
First, I made the commitment to build a newsletter last week, September 24th. Here’s a screenshot of me telling my team of this possibility:
And by the end of the day, I had finished building out my newsletter stack — I tweeted my thoughts nearly 12-hours later:
I then spent the weekend emailing, DM’ing, and texting a few friends who I knew would support this new project and give me valuable, early-feedback. I emailed them that same day!
I made my ask simple and straight-forward and I got some quick replies:
My goal was to get 10-12 subscribers who would test-drive the content for the first week, 5 posts total. Here’s an example DM request:
And after the first issue (Monday’s update) I started getting feedback:
I continued to publish, get comfortable with the workflow and new schedule, reviewed feedback from caring friends and early-community members, and then iterated as-needed on both the technology and overall process.
I also made sure to respond to every comment on Substack:
Learning how to build community through a newsletter takes time and intentional care — never leave an opportunity to connect and engage as it presents itself!
Finally, I decided to publicly announce YEN.FM to the world on the first Friday, which is
today. I had originally planned to wait the weekend and launch on the upcoming Monday, but, I am too impatient to wait and want to start growing the newsletter and community immediately.
That’s just the creator and builder in me!
Now, it’s all about consistency, not giving up, iterating on the model, presentation, style, workflow, and tooling. I expect great things.
Final Thoughts and Other Slightly-Random Considerations
I’ve intentionally built this deep-dive as more of a tactical
how-to and less of a strategic
playbook that will cover most growth and community-building scenarios — I don’t have time, energy, or interest, especially since folks like Steph Smith have done a much better job (20+ pages!!) going through the finer details and considerations:
My hope is that this inspires you to newsletter greatness and that you’ll find that starting one isn’t as hard as you might think! Writing it consistently (and not giving up) is where the magic really happens.
A few tidbits that don’t fit anywhere specific:
- Featuring your subscribers and community members is a tried-and-true, go-to growth strategy.
- Substack opens up the possibility of monetization but I don’t have any strong feelings about that, especially in the beginning. I think it’s more important to learn the mechanics of writing on a schedule before learning how to monetize your audience. But, I know that you can monetize as-early as < 100 subscribers, so, there’s no bottom threshold.
- “Modal” windows and other fancy widgets get in the way and can bloat a website very quickly. Try to minimize your technical stack before you add to it. For WordPress, I only use two plugins so don’t go crazy.
- One of the most under-appreciated facts about writing is that it takes a while to find your “voice” — I don’t have any advice other than to not quit. if you quit, you’re guaranteed to not ever find it. If you don’t quit, you will find it. That’s all I can say about that.
- Use pictures.
- The style of your writing should be “comfortable” — if that looks and reads more “personal” (or personable) or if ends up feeling a bit more “polished” and “professional” then so be it, doesn’t matter. You need to write in a way and form that feels natural and fluid for you — your readers will thank you.
- Please do this, you’ll thank me later.
🛑 — Send me a link to your email newsletter! I’d love to read and subscribe!
As always, the greatest compliment you can give me is sharing our newsletter with others!