Caitlin Dewey is already making more than half her former full time salary from $7/month reader subscriptions.

That’s pretty damn impressive.

Especially since she only launched her paid subscription 5 months ago!

Caitlin’s been writing Links I Would Gchat You If We Were Friends for a decade (on and off) but, like many of us, she didn’t take it that seriously as a business…until now.

Honestly, this is fast speed-to-monetization already but might as well go for the gold! Let’s see if we can get Caitlin back to her full salary faster (plus a raise!)

In service of this goal—doubling Caitlin’s reader revenue—I wrote a reasonable promo plan for the busy journalist who produces a newsletter, freelances during election season, and teaches at a university.

And I thought, why not just share it with you too? Check it out below!

P.S. I wrote this promo plan for fun. Caitlin didn’t ask me to though our conversation inspired this issue. If it saves you time, you can Buy Me a Coffee ☕️ 

Steal this subscription promo plan

I’m exclusively focusing on marketing Caitlin’s paid subscription (not on growing the list).

Caitlin’s on Substack so I created this plan with that platform in mind.

Automated vs manual promotions

One of the main gaps of Substack is no email sequences. You pretty much need email sequences to sell stuff effectively and this is why I think Substackers have lower free to paid conversion than other publications.

But we’re still going to automate as much as we can.

This is not passive income and you won’t just set and forget these (you’ll check on how they perform and optimize them) but a mediocre promo email that actually goes out is better than no email at all.

Note: some of the tools I recommend below use my affiliate link and I may get a commission if you buy something but I only recommend tools I think are valuable for you and there’s no cost for you to use these links.

⚙️ Automated promotions

Website

• Add a “Why Go Paid” page: Set up a custom page, call it something like “Why Go Paid” and sell the hell out of why readers should support you or why they might want to get behind the paywall. 🔗Example from Matt Kiser

• Make a Wall of Love: Use Senja to create a dynamic page of your testimonials. Link it to your navigation on Substack. Import all social shout outs and paid reader testimonials into Senja so they automatically display on the Wall of Love. Enable the floating call to action block to send people to your upgrade page and you can also use your Wall of Love as a promo page. 🔗Example from My Wall of Love

• Consider auto-paywalling older posts: Substack has this built in and while it’s great to have some free posts for people to see, you might want older posts to be fully paid.

Email

• Add a 30 day free trial offer in the welcome email: Create a special offer that gets them on the paid tier right away. 🔗How to add a free trial

• Set up a welcome email for paid subscribers: Use Zapier to do this (Trigger off your Gmail notification from Substack). In that welcome email, get them to tell you why they upgraded. Ideally, you have them take it to social media directly and tag you but a reply is fine too. You’ll use it as a testimonial and you’ll learn what made readers upgrade.

  • Bonus points: Senja also handles this testimonial → social share for you. It’s a setting called “Word of Mouth” on the testimonial form.

Social

• Set up autoplug on all platforms: Use Hypefury to hook up all social platforms you use (X, LinkedIn, Instagram, Threads) and use their autoplug feature. Load in 10 evergreen plugs, 5 promoting your free newsletter and 5 promoting your paid subscription. These will auto-reply after your posts get traction.

• Load in evergreen promos for all platforms: In addition to auto-comment, Hypefury will also auto-post for you. Write at least 5 promo posts for your paid subscription and Hypefury will keep them going out. Some of your readers won’t be newsletter fans (they might read on web or on social), get ‘em into a sub!

🖖 Manual promotions

Website

• Show us your sub goals on the About or Go Paid page: Tell your subscribers where you’re at and where you’re going. List milestones here by paid subscriber count and share what is unlocked at each milestone. Update this monthly or quarterly when you do a big promotion. 🔗Example from Aftermath

Email

• Plan 4 seasonal promo campaigns: If 4 times a year is too many, start with twice a year. A seasonal promo campaign includes:

  • An angle: a sale, a theme, a bonus, a reason or a milestone

  • At least 3 dedicated emails: these will ONLY promote the paid offer

  • At least 5 additional mentions: around the “upgrade to paid” block

  • 🔗 Example from RANGE

• Create a call to action menu and rotate them in the weekly emails: Set up a spreadsheet of your calls to action and rotate position and message every week. If you have time, track which ones work best, but also know that they are working together to build a case for the upgrade.

  • Include in this rotation the “Why Go Paid” and “Wall of Love” pages in addition to the “Upgrade to Paid.”

Social

• Promote your milestones on social: As you hit milestones or even if you’re just excited about a busy day of upgrades, share it on social media. You can screenshot your growth chart from Substack OR use a reader testimonial to show off the traction. 🔗Example from my Buy Me a Coffee 

• Plug your subscription on any post that gets traction: As a backup to the automation, whenever you have posts that take off, plug your paid subscription with a super relevant message. 🔗Example from Nick Pinto at Hell Gate

If you take nothing else away from this email…

Remember that you actually have to sell your paid subscriptions. “Upgrade to paid” is not sufficient. Fresh takes are needed!

Your readers want you to convince them to part with their money. Do that well and do it often and you’ve got growing recurring revenue.