7 Mac apps shipped as a solo developer. No sponsored opinion.
I sold Mac apps on Gumroad for over a year.
It worked. Simple setup, clean JP/EN storefront split, flat 10% fee. For a solo dev
shipping their first paid app, the simplicity matters more than the fee. I recommended
it. I built my entire payment infrastructure around it.
Then it fell apart in the most frustrating way possible.
The first sign: a UI I couldn't even use
I hadn't logged in for about a month. When I did, there was an error message telling
me to contact support — with a link I couldn't click. The UI itself was broken.
I want to be upfront about this: yes, I hadn't checked in for a month. But the problem
wasn't that I'd neglected something that needed maintenance. The problem was that
Gumroad's own interface for reporting a problem was broken. I couldn't even follow
their instructions.
So I went around it and contacted support directly.
The support loop
Gumroad's support starts with an AI bot. Fine. I answered its questions. It asked the
same questions again. I answered again. Same questions.
The bot wasn't moving toward a resolution. It was just looping.
I asked to be escalated to a human.
They agreed.
That was the last response I ever received.
For over a month, nothing. No follow-up. No resolution. No acknowledgment that my
storefront had an active error.
Then I opened Gumroad one day and payment was just... gone
No warning email. No violation notice. No explanation of any kind.
I just logged in one day and both Stripe and PayPal were no longer functional. My
Gumroad account still existed — I could log in, see my products, see my sales history.
But payment processing was dead. Stripe banned, PayPal frozen, simultaneously.
In practice, it didn't matter that my account was technically alive. No payment
processor means no sales. For a solo dev with no backup platform, it was effectively
a shutdown.
I still don't know why. No reason was ever given. My support ticket was still open
and unanswered when it happened.
Emergency migration to LemonSqueezy
I had apps listed. Customers trying to buy. Zero way to process payment. I had no
choice but to move immediately.
The migration meant:
- Rewriting Cloudflare Worker license validation from scratch — the logic that verifies purchase keys on every app launch had to be rebuilt for LemonSqueezy's API. Several hours of work across multiple apps.
- Rebuilding DMGs for every app — each binary needed updating to point to the new validation endpoint. With 7+ apps, this alone took the better part of a day.
- Registering all products on LemonSqueezy and submitting W-8BEN tax paperwork.
Time I hadn't budgeted. Time I should have spent building.
LemonSqueezy works. The checkout is cleaner. Tax handling as merchant of record is
genuinely better. I should have diversified earlier.
What I actually learned
Two things, not one.
First: check your storefronts regularly. Platforms can break silently. A month of
not logging in was enough time for something to go wrong without me knowing. That's
on me, and it's a cheap lesson compared to what it could have been.
Second — and this is the bigger one — Gumroad didn't fail because it's a bad product.
It failed as a platform dependency. The lesson isn't "use LemonSqueezy instead." The
lesson is: never build your payment infrastructure around a single platform you don't
control.
Concretely:
- Have a backup payment processor ready before you need it
- If support goes silent for weeks, start migrating — don't wait for resolution
- Platform risk is real, boring, and easy to ignore until it isn't
The ticket is probably still open.
If you're a solo dev selling digital products — how are you handling platform risk?
Have you ever had a payment processor disappear on you?
