Depressing churny moments

Thought I'd share two depressing moments from Cloakist life where I suddenly realised I was in for a whole load of churn.

For context, Cloakist is early-stage: currently at $650 MRR. I've written some more about how I got there here. You don't really need to know what Cloakist does to understand this post.

Depressing churny moment 1: users weren't using

I was at around $250 MRR and feeling pretty great that I'd got that far in a few months since launch. But then I took a closer look at my customers and realised that almost half were not properly using the product. Their sites weren't live any more, or they'd never got around to doing the set up I emailed them. That meant that they were surely bound to churn (and sure enough, eventually a lot of them did).

It was a pretty sickening realisation that my extremely hard-earned MRR was not there to stay. I'd been so focused on getting new customers in, it hadn't really occurred to me that someone would pay and not use the product. That feels counter-intuitive.

What I learned: MRR is only surface-level. You need to dig deeper to understand whether you're really solving a problem.

Depressing churny moment 2: users forgot they were subscribed

A few months later, I found myself crossing $650 MRR when I started getting requests from some customers for monthly receipts.

It hit me: Stripe wasn't emailing my customers every month to tell them about money leaving their bank account. I don't know how or why, but Stripe Checkout - which I use - doesn't seem to do this by default. INSANE!

I felt like morally speaking I couldn't not send people emails whenever they paid me money, so I found the option in Stripe to do this (it was bizarrely hard to find) and switched it on.

And as you've probably guessed...major churn, round 2. People who were using the product but clearly didn't really need it that much started realising, and started cancelling. I lost $50 MRR within a few days, and I'm expecting to lose more in the coming weeks.

Painful AF. But the right thing to do (Or is it? You tell me!).

What I learned: set yourself up better in the first place. Always send customers emails every time you charge them.

If I had to wrap all this up in one big message, it would be:


That would have stopped both of these moments from being unexpected, and therefore depressing.

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