Alright, let's fix this …
If retention is about results (not communication), and if customers need to recognize progress (not just experience it), then here's what you need to build …
A "first win" system.
It's simple. It's fast. And it changes everything.
Here's how it works:
Step 1: Define the first win
Ask yourself: What should customers notice in the first 14 days?
Not the final transformation. Not the big result. Just the early signal that tells them they're on the right track.
For a sleep supplement, it might be … "You'll fall asleep faster, even if you're not sleeping through the night yet."
For a skincare product, it might be … "Your skin will feel smoother to the touch, even if you don't see visible changes yet."
For a fitness program, it might be … "You'll feel less sore after workouts, even if you haven't lost weight yet."
The first win is the thing that happens before the big result … but proves the big result is coming.
Step 2: Tell them what to look for
Most customers don't know what progress looks like. So they miss it.
Your job is to tell them exactly what to pay attention to.
Create a simple "what to expect" guide. Something like …
Days 1-7: Here's what you should notice
Days 8-14: Here's what should be shifting
Days 15-30: Here's when the bigger changes start
This isn't hype. It's orientation.
You're helping them interpret their own experience so they don't evaluate too early or through the wrong lens.
Step 3: Make it impossible to miss
Don't bury this in a long onboarding email or a FAQ page.
Put it everywhere …
On the landing page
On the thank-you page
In the first post-purchase email
On a card in the box
In a follow-up email on Day 3 and Day 7
The goal is to make sure every customer knows what "on track" feels like.
Step 4: Check in at the right moments
On Day 7, send an email that says …
"By now, you should be noticing [early signal]. If you are, you're right on track. If not, here's what to adjust …"
This does two things …
It reassures customers who are seeing progress (so they don't second-guess it)
It helps customers who aren't seeing progress figure out what's wrong (so they don't just quit)
That's it.
Four steps. One clear outcome. One believable timeline. One early signal.
You're not adding more communication. You're adding clarity.
And clarity is what turns uncertain customers into confident ones.
Here's what happens when you do this …
Customers stop asking "Is this working?"
They stop evaluating too early.
They stop churning quietly.
And retention stops feeling like a constant battle.
Because now, customers can actually tell that life is better.
And when life is better, staying is the obvious choice.
So here's my question for you …
Can you describe, in one sentence, what your customers should notice in the first 14 days?
If you can't, your customers definitely can't.
And that's where retention is leaking.
Hit reply and tell me what your "first win" is. I'd love to hear it.
See you tomorrow,
Jeremiah
P.S. If you're sitting on a bunch of new customers from the holidays, you have about a limited time to get this right. After that, they'll either be on track to stay … or they'll quietly drift away. Don't let that happen.
100% Typo Guarantee … This message was hand-crafted by a human being … me. While I use AI heavily for my research and the work I do, I respect you too much to automate my email content creation.
There was no review queue, no editorial process, no post-facto revisions. I just wrote it and sent it … therefore, I can pretty much guarantee some sort of typo or grammatical error that would make all my past english teachers cringe.
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