Issue #18 - July 1st, 2025
Written by Michael Gillespie
In this issue:
Perspective: If they don’t care about your product, they’ll never convert: Why optimization only gets you so far with prospects.
Insight: Your membership must be positioned in the life of the member, not in the mind of the operator.
Outlook: Notes on why you should stop trying to impress people and start trying to understand them.
QUOTE OF THE WEEK
“You can’t optimize someone into caring.”
Every week, I speak to operators with the same frustration:
“I’ve got a solid offering. A clean landing page. Real benefits. But I’m still seeing way less conversions that I know I should be.”
It’s a gut punch. Especially when you know the thing works.
But here’s the truth:
People don’t buy because of what you’ve built. They buy because of what they believe.
And belief doesn’t come from bullet points, clever promotions or even the best-looking landing page.
It comes from resonance.
It comes from striking at the heart of what a potential buyer might be missing in their life - and then showing up intentionally to fill that void.
Membership isn’t always a game of numbers, metrics or margins.
It’s a game of empathy.
So in a world where everything is for sale, here’s the question that’s on my mind when it comes to messaging a membership to a set of prospects:
How do you make them care?
Let’s dive in.
PERSPECTIVE
Even the Clearest Pitch Falls Flat Without a Heartbeat Behind it.
We’ve optimized everything.
The headlines, the onboarding flow, the CTA buttons, the trial offer. But still, conversion feels hard.
If that sounds familiar, you’re not alone. In fact, it’s a sign you’re doing the right things.
But here’s the reality when it comes to membership:
Clarity gets you seen, but conviction gets you chosen.
You can list all the features.
You can say “new content every week” and “exclusive interviews” and “behind-the-scenes access.”
But if none of it answers the deeper question, “Why does this matter to me, right now?”, then you’re just offering more noise in an already deafening room.
I’ve seen just about every kind of membership that exists. And there’s a common framing and perspective that makes prospects become members.
Consider this:
People don’t buy cooking memberships to access more recipes. They buy because they want to feel confident in the kitchen again.
People don’t buy fitness memberships to count reps. They buy because they want to make a serious change.
People don’t buy financial memberships to see more spreadsheets.They buy because they’re tired of feeling behind and ready to feel in control.
People don’t pay for podcasts because they want more episodes. They pay because they want to feel understood - and they trust you to say what they’ve been thinking.
You see, these people aren’t buying content at all.
They’re buying resonance.
They’re buying a more meaningful version of themselves because these memberships named the problems being faced and then painted a clear picture of what being on the other side of those problems looks like.
And when this is all done successfully, something powerful happens:
People begin to care about what you’re offering.
INSIGHT
Start Where They Actually Are.
There’s a shift that most operators never make:
They keep trying to get people to care about the product instead of helping them see how the product fits into their life.
After years of working with clients at Memberful and helping them sharpen their positioning, I’ve found the following four actions to be most effective at drawing an audience in:
1. Speak to the struggle, not the specs.
If your copy doesn’t name what’s heavy, frustrating, or missing in someone’s life right now - it won’t land. Don’t start with “here’s what you get.” Start with “here’s what we see in you.”
2. Sell the feeling, not the format.
They don’t crave content. They crave confidence. Relief. Belonging. Possibility. Your features are just the bridge, not the destination.
3. Position it like a missing piece, not an extra.
When you really understand your member, your product stops feeling like a nice-to-have and starts feeling like finally, someone built this for me.
4. Tell a truth no one else is telling.
Generic messaging dies on contact. But when you say something that makes someone feel seen? That’s where trust begins. Points of view matter - and there’s often lots of truth hiding within them.
Don’t become wrapped up in the trap of being “better” or “more polished.” Instead, put your energy into being real and relevant in the eyes of your potential members.
And most importantly, be honest enough to say the thing others aren’t willing to say.
OUTLOOK
It’s Not About Selling Better. It’s About Seeing Better.
If you want your people to care about what you’ve built, start by caring more about what they’re going through.
Because at the end of the day, the best memberships don’t feel like products.
They feel like permission. They feel like relief. They feel like finally, someone gets it.
And that can only happen when you stop trying to impress people and start trying to understand them.
This is what lies at the absolute core of your own success in membership. It’s fundamental to everything you’ll do. But it’s also the hardest.
What would change if your goal wasn’t to sell a product but to earn someone’s trust?
If you’re like most operators, there’s a lot that would change. Not because your mission is wrong, but because, as operators, we’re naturally concerned with moving our businesses forward - it’s what we’re wired to do.
But too often, it’s at the expense of failing to truly understand the people we expect to become our customers.
From where I stand, that’s something an operator simply cannot afford.
So, like always, I’ll leave you with this question today:
Are you building something worth buying or something worth believing in?
Think about it.
IN CLOSING
Tell me: How can I help you with your membership? Respond to this email and let me know (I always read every reply).
Share: I want Operator to be the most valuable thing that comes across your inbox each Tuesday. If I’m hitting that mark, share this newsletter with your staff, a team member or friend (just copy and share this URL).
See you next Tuesday.
-Michael