Stop promoting at the wrong time. Get on your reader's timeline.

I subscribed to 404 Media this week because of one standout email they sent.

Of course, I’m an easy convert because I spend a fair bit of cash on independent news. BUT their strategy here points to something we should all be doing: keying promotions off our reader’s timeline, not our internal timeline.

In today’s issue, I break down why this strategy works so well and how you can run it yourself.

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Send a reader-specific promotion

Here’s the email 404 Media sent me.

Why I like it

• It’s personalized: It acknowledges that I have a relationship with their publication (albeit a soft one). They convey a sense they “know” me with language like “you’ve been a free reader for a pretty long time.” This is simple and generic language, but it makes me feel like they’re paying attention to individual readers. It also instills a sense of responsibility that I personally should support the work I’m consuming.

• It was sent at the right time: This was sent about 7-8 weeks after I joined their newsletter. Doing some research for another publication, I found similar timing was common for an upgrade. It’s enough time for me to get familiar with the work, make it a habit and start thinking I should be a subscriber (if that’s a thing I’m going to do).

• It includes a hidden discount: The discount is only available to me via this email. It’s not on their website or in their standard newsletter. This is actually surprisingly simple to implement—see more below!

There’s a bunch of other stuff I love about this email like how it came from one person (Joseph) rather than the entity, the fact that they outlined all the perks and the short clear subject line that isn’t about saving journalism again (“A chunky 25% off 404 Media”)—but those are aside from the strategy we’re talking about today.

How they did it

404 used Outpost to send this promotion. Outpost is a publishers co-op built on top of Ghost, specifically for driving reader-funded growth.

It’s not clear to me how much lift Outpost does here (compared to the 404 Media team), but rest assured, I’m going to find out!

How you can do it

1. Set up an automated email in your newsletter tool to send 6-8 weeks from subscribe (Instructions for Substack, Instructions for Beehiiv, Sadly seems not available in Ghost which may be why Outpost is necessary)

2. Tailor the 6-8 week timeline if you don’t send your newsletter weekly (make it longer) or use your own subscriber data to determine the most likely time for this upgrade.

3. Create a discount in Stripe or in your payment processor (it can be one code that you use for everyone)

4. Write your enticing subject line and email

5. Add a button in the email that takes them to the upgrade page (you can either pre-load the code or give them the code to type in)

6. Add two buttons if your email is long

7. Test and publish your automation!

If your tool doesn’t allow automations, you can also make this offer in your welcome email. It will likely be less effective because it’s a little too soon but I’m about to test it so I will report back!

Our takeaway

We can pay more attention to how readers engage with our subscriptions and tailor our promotions to them more accurately.

Readers who become paid subscribers are not convinced in an instant. They slowly become more ready to take that action. The better we meet that moment with the right message, the more subscribers we can gain.

Reader-specific marketing seems like a big opportunity space for publications and I’m looking forward to learning more about how Outpost and other tools are solving this.

An invitation

I’m a growth marketer and I love getting my own hands on the data. If you want to run a test together on the above idea, please reply to this email. I work on a sliding scale from very cheap (for teams) to free (for solo writers) if you let me publish the results here :)