I built a small utility as well, and I'm using a somewhat unique payment model.

It's free and open-source on GitHub. You can download the source code and build it yourself with Xcode.

https://github.com/pkamb/powerkey

I also provide a $5 built app available to purchase via Gumroad, code-signed with my Apple developer account and ready for immediate use without Xcode with no scary macOS warnings:

https://gumroad.com/l/powerkey

I found that this model works really well for small projects where you want some of the benefits of open source and don't want to deal with upgrades or nag screens.

It would be even better if GitHub built some "paid release" features into their product, in addition to their Patreon-style Sponsors feature.

This is one of the things I can't stand about MacOS. I feel like every little thing my OS should be doing for me I have to pay for. $5 to remap my power key? No thanks. I also can't believe there aren't window tiling shortcuts either.

It's not just having to pay that's the problem. I like the ability to reinstall my OS whenever I feel like. This adds another step to setting up my machine and is extra work to automate.

Companies will only pay if they're forced to pay and are aware that they have to pay in the first place. That means you better have a nagging screen and better make it very clear that commercial usage requires a paid license.

For desktop software, I'd suggest to detect if the system has a proxy configured, that's a good hint whether it's a corporate computer.

Is true? Can you just run unlicensed tools at your work?

Many people can, and especially in smaller companies (but not only) its not unusual to see unlicensed software. A really well-known example is TeamViewer, who've been balancing the line between "don't break legitimate free users" and "catch companies using it"

Paying is the easy part. Getting a company to approve and reimburse a purchase is usually the blocker. That's why for most companies small purchases aren't worth the hassel.

Very small purchases often go on credit cards and get auto-approved. $20 (recurring monthly even) is likely to be under the “even needs a receipt” threshold.

> with clear notices that you need to pay to use it at work, and a way to contact me for a business license

But that’s probably one of the least user-friendly purchasing funnels you can possibly have. I think there’s some more basic lessons to learn about sales conversions before getting to those other conclusions you reached.

Of course, I'm aware of that. That's why I mentioned the friction on both sides (including mine) was relevant.

Setting up a "better" funnel would have cost me much more time, spent on stuff I didn't really enjoy doing, with no guarantee that I'd ever make enough money to give me a reasonable reward for that additional work. (Which would be more than the work that went into the tool.)

Maybe it would have worked and hundreds or thousands of people would have given me $5 or $10. Maybe the resulting support load would have been worth it. But again, I'd have to somehow make the free version less useful to have a decent chance on that. In retrospect, I regret not making the tool free from the beginning.

Why is making payment so hard in this world age. Doesn’t stripe make online payments super easy nowadays?

Making payment is not hard if you want the money to come from a human. If you want the money to come from a company, your hurdle is the expense approval and reimbursement process. This is not technical (and serves to try to protect the company from fraud so isn’t going to go away).