Brought to you with support from Outpost for Ghost publishers
You can only fit so much persuasion in an “upgrade to paid” button.
The reason you put those buttons all over is so readers know they can pay you. But those buttons don’t do much convincing. So where does that happen?
It happens in dedicated appeals! Hey, you’ve been here a while, here’s why you should pay…
Who has the time to do that every week? Not me! Not you! That’s why we’re gonna set up a “Why Pay” automation.
Your early supporters come in hot cause they already know you. Your later adopters need more mindset shifting to go to paid. A Why Pay sequence taps into the different motivators those readers might have through dedicated messages sent back to back.
The best part is that it is AUTOMATED. A Why Pay sequence will back up your other efforts and help ensure that, even when you don’t feel like promoting, you’ve got a little robot running in the background encouraging readers to smash that upgrade.
I wrote you 7 recipes you can use for your Why Pay sequence. You can pick and choose from them and put it together any way you like!
Want to get this into practice right away? Join me for a Why Pay Sprint starting April 1! I’ll send you a prompt every week in April and you can respond to it via email. By the end of the month, you’ll have a Why Pay sequence. No calls. Just a little accountability. Sign up here (included in your Paid Sub Playbook membership!)
The Why Pay sequence is part of both the Foundation Map and the 3×3×3 Growth System. I consider the Why Pay sequence to be a key paid upgrade lever and strongly recommend you try it! It’s hard to screw up and it pays back your time quickly.
P.S. I’m hosting a mixer for my Legends subscribers on April 10 and I want to extend the invite to you, but just you (please don’t share it.) I’ll match you with people you should meet based on your preferences plus there’s live music. If you want to meet other creative entrepreneurs (designers, marketers, writers, coaches, sales, ops), join us!
In this play
💰️ Pick your “Why Pay” recipes
You’re going to send this a couple months after someone joins your newsletter. They’ve gotten to know you and your work a little bit and now it’s time to ask for the upgrade in a big way. I put more recommendations about timing at the bottom. Let’s look at the recipes first.
Choose any mix of the email recipes below. I recommend starting with a 3 email sequence (and that’s what we’re doing in the sprint!) but you can send as few as 1 email and as many as 7 emails.
I find the more emails I send, the more paid subscribers I get. And I know you’re worried about unsubscribes, but generally if people are unsubscribing, they weren’t going to upgrade to paid anyway. Your big fans will stick around through this if they’re not ready to pay.
🎯 Desired result: Get X number of free readers to become paying subscribers. You decide what X is!
⏱️ Estimated time to complete: 2-4 hours
💡You don’t need to send these in the order I have them here. It probably does not matter what order they go in. I see it more as a compounding effect where the different messages plus the short burst of them coming one after the other is what works. But tell me if you learn something different!
Email 1: Origin story
Nothing captures attention like a good origin story! Just because it’s on your About page doesn’t mean your audience has actually seen it. Reinforce where you came from with your readers as you call them to support where you’re headed.
Subject line examples:
- The story behind [PUBLICATION]
- It all started when [EVENT HAPPENED]
- If only [TOPIC/SITUATION] were different, we wouldn’t need to exist
Body prompts:
- Opening hook: The one story that sparked the publication, how the team met, why your last publication shutdown/how you got laid off from it, OR what got you thinking about this topic
- Share something personal: Could be about you, the team, the vulnerabilities of the industry you cover or the time we’re in, OR something a source or subject shared (that’s public)
- Follow on with the mission: Explain what the focus/purpose of your work is, remind readers of what they can expect from you, OR lay out a short, inspiring future state.
- Close with the ask: Upgrade to paid, become a member, contribute. (You can include this more than once if the email gets long.)
Escape Collective’s origin story is pretty epic and very convincing to get you chipping in!
Email 2: Where your money goes
When you’re taking in money, it helps for people to know how it gets spent. This recipe is especially interesting if you have unexpected costs that they might never consider, team members they rarely see or if you just want them to feel secure knowing their money is put to great use keeping your family housed and fed.
Subject line examples:
- Why we’re funded by readers
- What your subscription actually pays for
- Help us each buy pools for second homes
- Where your money goes
Body prompts:
- Opening hook: Make a joke about subscription fatigue, make a joke about how little journalists make, open with something you paid for thanks to your subscribers (ideally story-related, publication-related), OR start with a question like “Ever wonder where your money goes when you subscribe?”
- Share how you think about reader revenue: A line or two about how you choose your revenue goals OR why reader revenue is important.
- List a few things readers pay for: Your salary is a valid one, any other costs of your reporting or costs of hosting your publication, freelancers, marketing OR anything else that your readers have probably never thought about.
- Close with the ask: Upgrade to paid, become a member, contribute.
Email 3: Why paid subscribers upgraded
This is a testimonial recipe and I highly recommend choosing this one. Your audience will put things into words differently than you would and it can help others to see themselves in their fellow reader’s perspectives.
Subject line examples:
- Why bother paying us? Let’s ask our subscribers!
- This one story made [SUBSCRIBER NAME] want to subscribe
- Here’s why [PUBLICATION] readers started paying us
- [SUBSCRIBER NAME] says “[QUOTE EXCERPT]”
Body prompts:
- Opening hook: Share a quote from a reader, highlight one motivator/perk that gets subscribers excited, OR talk about what made you realize the perk is actually the stories and content you produce, not a t-shirt.
- Subscriber stories: Pull out one testimonial and talk about why that subscriber joined (you can do 2-3 back to back) OR organize this by 3 main motivators and put reader quotes under each one. You can also do this whole email around one reader if their story or quote is good.
- Keep the surprises coming: Remark on something subscribers have valued that surprised you (a story, a coverage area, an event, etc) OR a perk you don’t talk about much.
- Close with the ask: Upgrade to paid, become a member, contribute.
Email 4: What went into this one story
Your readers appreciate you but they don’t think much about how much work goes into what you do, not to mention costs aside from your labor. You can break down both with this recipe.
Subject line examples:
- Reporting on [TOPIC] isn’t free. Here’s what it costs.
- We’re learning how expensive saving journalism is
- What it cost to produce [STORY/HEADLINE]
Body prompts:
- Opening hook: Pull one unexpected cost to open with, bring us inside a story you covered, OR play off the “save journalism” trope/reality.
- Break down the costs: Use one story as an example OR give us a breakdown by month. Remember that your salary and labor costs are real costs and should be accounted for like anything else.
- Reinforce your financial goal: Remind readers about your operating model (nonprofit, solo, worker-owned, indie, etc) OR tell them your overall target (could be a revenue goal or a “pay ourselves full time” kind of goal.)
- Close with the ask: Upgrade to paid, become a member, contribute.
💡No other links! I warn you strongly against including any other links in this email. If you really must link a story, then do it, but try to avoid it. You’ll distract your reader from the one action you want them to take.
Email 5: Perks of going paid
This recipe just tells subscribers what they’re going to get if they upgrade. It’s hilarious how rarely people go check the page where perks are located so you’ve gotta make it super obvious with an email like this.
Subject line examples:
- What do paid subscribers get?
- All the perks of being a paid subscriber
- Did you know you could get [GREAT PERK]?
- That New Yorker tote bag got a revamp
Body prompts:
- Opening hook: The one perk people rave about, a photo of you fulfilling a perk + the story behind the photo, acknowledgement that subscribers don’t join for perks but that perks are nice, OR a hidden/lesser known perk.
- List the perks: Bullets work great here (see Max Read’s example below). If you have more than one tier, I recommend prioritizing one and giving a shout out to a second. Don’t cover three tiers in one email.
- Photos if you have them: If the perks are visual OR if you want to include a photo of you/the team, this is a great email for that.
- Close with the ask: Upgrade to paid, become a member, contribute.
Max Read’s subscriber perks list
Email 6: Where we’re headed next
Laying out your vision is a great way to get your readers excited about contributing and following along. You can share new topics you want to cover, new people you want to bring onto your team or just some hopeful optimism about what you and your audience can do together.
Subject line examples:
- The future as we see it at [PUBLICATION]
- Wouldn’t it be cool if [FUTURE SCENARIO]?
- What’s coming soon for [PUBLICATION]
Body prompts:
- Opening hook: Paint a picture of the future as you see it (for yourself, the world, your publication, your reader, etc), use a device like “picture this” or “imagine this,” start with a subject/story you’ve covered and what they’re trying to achieve OR make a joke about how you didn’t think you’d make it this far but you’re still going!
- Lead with the vision: Explain why you do this work, contrast what was missing before you/what it’s like with your work out there, OR give a clear impact measurement like if every reader knew how to recycle batteries.
- Break the vision into tangible pieces: Give them 2-3 tangible things that would change for them personally, for the world, a group, an industry in this future. On the personal side, you’ve got things like “you’ll spend less time doing X” or “you’ll make smarter purchases of Y.” For broader impact, it might be “Google can buy less surveillance tech unchecked” or “We’ll get these congresspeople out of office faster.”
- Close with the ask: Upgrade to paid, become a member, contribute.
Email 7: What happens if this goes away
No need to make this super threatening like The Intercept did but it’s a very real thing that your project needs funding and you can absolutely say that. You can take a personal tack here and talk about moments of doubt and despair or you can speak more to your industry and the times we’re in.
Subject line examples:
- Turns out [PUBLICATION] could shut down (Yes, I know this is super clickbaity)
- What if [PUBLICATION] went away?
- How many outlets have we lost this year alone…
- We didn’t think [PAST PUBLICATION] could evaporate, but then it did
Body prompts:
- Opening hook: A semi-threatening line about your work going away, a callback to publications that have shuttered (one you worked at or other famous ones), OR a question you pose about how they’d feel if this didn’t exist.
- Point out the stakes: Talk about how it’s very real that publications shut down and while you don’t want to do that, it’s always a possibility, remind readers to support the work they love and value with their money OR get real vulnerable with how touch and go it can be as an indie publisher. You can even give a real example like a medical expense that meant you needed to bring in a freelancer or lawsuit threat.
- Highlight why reader funding: Add a line or two about why reader revenue benefits them with your editorial independence (even if it’s not your full revenue, having their backing helps you stay more independent/turn down bad incentives.)
- Bring it to a hopeful place: End on a positive note that you want to continue and you believe you can, with their support.
- Close with the ask: Upgrade to paid, become a member, contribute.
A “this could go away” email from Luke at RANGE titled “Save RANGE” which did in fact save RANGE!
💡Hot Tip: Look back at all of your dedicated reader appeals or sale promotions to see if you can pull messaging that has ALREADY worked into this Why Pay sequence. Make sure messages are evergreen or could work for at least 6 months.
⚙️ Put your “Why Pay” sequence in place
When to send it: At the most likely time for upgrade. I estimate this to be somewhere between 2-6 months after they first join your list, based on data I’ve seen.
Ideally, you’d dig into your own data in your newsletter/membership tools. Download your newsletter list, your Stripe data, merge them on email and use a Google formula or an AI tool to find the averages.
But if that sounds too hard, set your sequence up for 2 months post subscribe and adjust it later if it doesn’t work.
How often: 1-3 days apart once the sequence starts running. Send closer together if you publish weekly or daily. Send farther apart if you publish monthly.
How long should these be: No less than 2 paragraphs and no more than 6 paragraphs, roughly. However long it takes to get your point across.
How to send it: Look for automated sequence capabilities in your email tool.
- Buttondown has automations you can customize based on a subscriber segment, tag and behavior.
- beehiiv allows sequences and you can add this to your welcome sequence or make a new sequence with a time delay after “sign up.”
- Ghost does not allow automated emails at all, you'll need Outpost.
- Substack does not allow for custom automations. You can either send this manually as a campaign a couple times a year or add a secondary tool built for email marketing like Kit or Mailerlite and then use Zapier to connect the lists. This is a clunky solution and I don’t necessarily recommend it.
💡Hot Tip: You can run this as a campaign and then turn it into an automation too!
Got questions? Want to share breakthroughs or blockers?
I’d love to hear it! You can either comment on this post or send me a question.
I also want to know if you find other angles for these evergreen upgrade promotions.
What's missing from this play?
Nothing, I got it! One thing, I'll share it! A lot, I'm lost!
