How to start your own good newsletter

Since I frequently talk about how newsletters are the most important part of my business (and generate almost all my revenue), I figured I’d explain the why and how a little more.

I’ve already covered why newsletters are better than social here, so let’s get into how we can approach newsletters in the best possible way.

There’s no one right way to do newsletters

There’s no one format that works best. What matters first is that it’s the best format for the subscribers you’ve got and want to attract, and second, that it’s the best format for you to keep doing it for a while and at a regular cadence.

My favourite three styles of newsletter are:

1. The longform. This newsletter is an example of the longform, mostly because I’ve never met a word-count I didn’t want to demolish, so this is the style mine obviously falls into. Cait Flanders writes a spectacular longform newsletter, as does Jessica Abel.
2. The curated roundup. Roundups are a nice way to provide value to an audience without having to write 1,000+ word articles each time. By sharing only the best links on a related subject, you save people time so they get the information they need without having to dig. Joceyln Glei writes my favourite and Dense Discovery is a close second.
3. The news. Similar to a curated roundup, the news style of newsletter is more focused on topical or breaking information, instead of just evergreen content. My favourites here are Charged and NextDraft. This style of newsletter requires a lot of work because you’ve got to digest current events quickly and then share the best content while it’s still timely.

For each of the three styles above, there’s one thing that’s consistent: you’ve got to write the emails. If you want to run a newsletter, you’ve got to write. This isn’t as hard as you think, nor do you have to consider yourself a “writer”. Everyone writes emails (except my dad), and everyone probably writes more words a day than they think. Sometimes we need to get over the stories we tell ourselves about what we can’t do and just do the work. Anyone can write. If I can write a newsletter each week, and my technical writing is awful (ask my copyeditor), then anyone can.

Minor pep talk out of the way, there are a few common elements to good newsletters. Good newsletters get opened, get read, and get shared. Maybe they don’t all have a million subscribers, but that’s a vanity metric anyway. I’d rather have a few thousand folks on my list who want to be there, open and read the things I send than a million who are just there because they signed up for some free shit years ago, forgot what it even was (or who I am) and created a filter to push my emails into their trash. The number of subscribers doesn’t matter. The number of subscribers who engage with what you send them does.

Good newsletters have a cadence

My list is called the Sunday Dispatches for a reason, and I’ve never, ever, ever missed a Sunday send out (except on pre-arranged breaks). People expect to see one email from me, once a week, with an article. That’s the social contract we’ve got with this list. If I do a good job at it, people look forward to getting that email.

If I never sold anything on my list, I couldn’t afford to keep my newsletter going. But, if I only sent emails on Sundays when I had something to sell or promote, there’d be no consistency and it’d be a one-sided relationship, only benefiting me.

By having a consistent schedule for sending a newsletter, I’m able to stay top of mind for folks, so they don’t forget why they’re subscribed or where the value is in allowing me to be in their inbox once a week.

Good newsletters are personal

Newsletters are interesting because they’re the only form of communication where 1:1 and 1:many exist in the same place. You can have an email from your mother right beside an email from Warby Parker. Newsletters that offer a little bit of personality or personal information remind subscribers that there’s a person on the other end, not just emails from corporate robots sent from a [email protected] address.

My own newsletter works because every reply goes to me, to my personal inbox (not a VA, not in to the ether). Being personal turns a one-way broadcast into an actual conversation. Conversations with people who are paying attention to you and your business are the most important thing in your business. It’s how I learn what products to create next, how to serve my audience better and stay valuable over the long term by sharing things most of them are interested in.

Good newsletters are private

Someone’s email address is sacred. Most people would rather give out their phone number. The only reason you’ve got their email address in the first place is because they specifically asked you to send them something. If you abuse that trust, you’re never going to make newsletters work.

Good newsletters are focused

Email is awesome because inboxes are for reading, quickly and easily. There are no distractions, no ads, and no popups in our inboxes. You don’t want to clutter up a newsletter with lots of images or graphics or branding. You want to cut the cruft because people are there to read and they’re mostly reading things in their inbox from tiny pocket computers with little screens.

When I used to do client work, people would always ask for a bigger logo, or a sidebar or the ability to have 1,534 colours, fonts, and styles. But every time I’ve A/B tested a simple newsletter design against a complex or overly-branded one, the simple design got more reads, more clicks, and more engagement.

How to start your own good newsletter

If you want to start your own newsletter, or tweak your existing one, I don’t have the answers. But I do have some solid questions to consider:

1. Who should be on your newsletter? What do they have in common with each other?
2. Where do those people who should be on your newsletter currently spend their time? Who do they currently read? Who has these people as part of their audience already?
3. Where and how will you recruit these folks? Where will they come from and why will they leave the places they’re already spending their time?
4. What need does this newsletter fulfill for these people? As in, why will they want to sign up and stick around once they learn about it?
5. How does the newsletter content fit into your greater content strategy? Will the content be exclusive? Will it show up on the blog at the time, or later? Will it be shared via social?
6. What format will the newsletter take? (Longform, roundup, news? Something brand new?)
7. What would be considered a success for this newsletter? Why?
8. How will you make time to plan, write, edit, schedule, and reply to these newsletters at a regular cadence? How many hours a week/month do you need to do this properly? What will need to be cut from your schedule, if it’s full?

Newsletters are my favourite thing because they give me a direct connection to the people who are paying attention, in a place that a huge corporation can’t own or change on a whim. Maybe newsletters are or will the be the most important part of your business too. Good luck.