There’s always frustration with how Square does X, or doesn’t do Y.
I know that because I’m one of the people saying it.
I’ve always encouraged others to be more active in solving their own problems, and to hold companies accountable when needed. That includes Square.
So to hold myself accountable, I started building an app that connects to Square.
That decision snowballed fast.
What started as “this should be simple” turned into thinking about selling it… which turned into user permissions, data isolation, billing models, compliance, and a whole world I had never dealt with before.
I built a few tools for my own store and, with AI, it was easier to get started than ever before.
But holy cow… it is still incredibly complex.
And that’s for one person, one store.
Square is operating at a global scale, supporting millions of sellers, across different countries, tax systems, compliance requirements, hardware, software, and industries.
My small app, which already does a lot for me, has a tech debt list a mile long.
About 80 active items across:
- core business functionality
- multi-tenant architecture
- compliance requirements
- infrastructure and security
- testing gaps
- and future integrations
And that’s before scale.
It’s easy to criticize from the outside. I do it too.
But building, maintaining, and scaling something like Square is a completely different reality.
So this is just a quick reminder to myself and others:
The teams behind this platform are dealing with an incredible amount of complexity every single day.
They deserve a lot more credit than they get.
