How to engineer serendipity with an email newsletter

And why they’re easy to start, hard to maintain

Three years ago I was on vacation, casually reading articles about AI, leadership and vulnerability. I was still at BlackRock, but the poolside daiquiris (not to mention the abundance of free time) led me to read a lot and broadly. I sent an email to 36 friends with the subject “A few interesting reads from my recent vacation,” briefly blurbed each article and signed off with the ominous “I probably won’t have the time to send out another one of these.”

173 weeks later, the newsletter has become this magical vehicle to expand my curiosity, develop my storytelling abilities, and AB test different digital business models. I’m in awe of the opportunities that something as simple as email can unlock for the entrepreneurially-minded, irrespective of age, technical level, and funding (or lack thereof) — a key part of my Unbundled Career thesis.

I often get asked to lay out the considerations in starting an email newsletter. So here are three things to consider about format, timing, tools and design. I’ll cover two services I know from firsthand experience (TinyLetter and Mailchimp) and four I know tangentially (Revue, SendGrid, Substack and ConvertKit).

1. Optimize for consistency (at the beginning)

If you don’t send an email, no one will read it. I know that sounds obvious, but the most important element of a newsletter (or any creative project) is consistency. By sending something weekly (and ideally at the same time) your readers become conditioned (and even anticipate) your newsletter. So at the beginning, remove as much friction as possible. Don’t worry about design, logos, and fancy analytics — these are just an avoidance trap for getting started. A good rule of thumb is that 90% of your time should be on content creation, 10% formatting. Without this, you’ll flame out.

Have a reader focus

Kyle Westaway, creator of the Weekend Briefing thinks it all starts with having a focus on the reader. He looks for the intersection of two questions: “What is necessary for my audience to thrive?” and “What unique perspective can I offer?” He’s sent out 224 consecutive emails and adds “even though it’s just curation, it still takes me 5–7 hours / week.”

In this early phase it’s important to have a loose structure around your Newsletter. Will you link blog (i.e. write small blurbs on others’ articles)? Write an essay? Share things you’ve created elsewhere (i.e. photos or videos)? Promote something else you’re working on (an online course)? Regardless, don’t get over ambitious. A good litmus test “if it’s beautiful outside or I’m sick, will I still want to send this?” Remember, it’s easier to add something than to remove it.

In this early phase, I’m a huge believer in TinyLetter (a Mailchimp subsidiary). You can also use Mailchimp for free, but may find yourself overwhelmed with customization options. Matt Clifford, co-founder and CEO of Entrepreneur First writes the weekly newsletter Matt’s Thoughts in Between in Revue because its simplicity ensured that he didn’t “have to think about beyond logging in once a week.” And though it might lack the feature set of a Mailchimp the ability to “sit down, type, and manage a straightforward sign up list” is all he needs.

2. Find your flow, then consider the next step

Ok. You’re past the hump where most people give up. People dig what you’re creating and you enjoy doing it. What’s next?

I’ve got < 5k subscribers and no plans to grow

Don’t fix what ain’t broken. Stay on whichever platform you’re on. But if you’re looking to grow or add new visual elements, TinyLetter won’t cut it. Here are a few directions to consider:

Is design important?

“Solid design communicates trustworthiness,” Westaway told me. Despite not having focused on the design in the early days (to his chagrin), the Weekend Briefing readers love it’s clean design. Design always matters, but there’s the trade-off of time and money. Templates can go a long way and offer a high degree of customization. Remember that you can add simple visuals via emojis, Instagram images, screen shots, and Giphys. Then there’s simple graphics tools like Canva. If you want to take it a step further, you could hire a Newsletter designer for pretty cheap.

Do I need to customize my lists?

For the longest time I thought that newsletter subscribers were one gigantic list that receives everything you send them. This couldn’t be further from the truth — an email list is a dynamic pool of addresses, each with very granular attributes ranging from open rate data, location, behavior (i.e. links clicked) and other collected data.

There’s one approach to newsletters that is inspired by advanced digital marketing tools and thrives on tailoring your newsletter based on what you know about your audience. Mailchimp enables this through segmentation and there are marketing oriented platforms (ConvertKit, ActiveCampaign) that offer less design flexibility in favor of a plethora of segmentation options. Be forewarned though that this becomes a rabbithole of analytics that can easily distract you from the broader vision of getting your ideas onto paper.

Do I need to integrate into other web apps

Here’s when your side hustle may turn into your main hustle. An engaged community of readers is often a sign that you may have something of value to offer. It could be books, courses, events, merch — in the days where you can literally slap one line of code to take payments — the possibilities are endless. But your newsletter platform will likely need an upgrade. Not only to handle the volume of email and subscriber data, but to provide true integration into Shopify/Woocommerce (ecommerce), Teachable (courses), Wordpress (blogging), Memberful (subscription options) and much much more.

Do I want a paid option?

I think we’re still in the early days for individuals launching paid newsletters, but the success of Ben Thompson’s Stratechery may be a sign that there is demand (I’m skeptical — Ben is a unicorn IMHO). That being said, Substack and Revue both have turnkey options to create a paid product.

3. Help me decide

• Getting started: TinyLetter (text only), Revue (simple tools for visuals) or Mailchimp’s free tier
• Subscriber analytics and tiering: Mailchimp or ConvertKit
• Customization and integration: Mailchimp or SendGrid (a cheaper, but harder to use Mailchimp)

Creating a beautiful newsletter has never been easier. As Bill Gates says, everyone has at least one valuable thing to add to this world: perspective. So what are you are you going to do with yours?

Hi, I'm Khe Hy and this is from RadReads, my weekly newsletter. Join 15,000 entrepreneurs, creators, and investors by subscribing here. We cover productivity, learning, and self-exploration and all our stories are at Rad.Family.