Hunter Walk has a fun post about indie software he pays for. I'd like to broaden my definition to include indie content, too.
Here's my list. I'd love to see yours!
Ulysses: A simple, markdown-based text editor that allows you to organize written content into groups. I also have a paid copy of Scrivener, but I find it heavy-handed for shorter work. Ulysses provides a much more beautiful writing environment. And I have IA Writer. Maybe one day I should choose.
Alfred: Literally the first thing I install on any new Mac. Spotlight has grown to incorporate some of its features, but its shortcuts, clipboard management, and workflows are second to none.
Stratechery: There is no better tech industry analysis newsletter. It's not always relevant to the areas of the technology industry that are most interesting to me, but it's always incisive. I pay for the daily updates. Theoretically this gives me access to the forums, too, but I'm not sure I've ever logged in.
The Establishment: Confession: I know the founders and invested in the site as part of Matter Seven. But in doing due diligence for that investment, it became clear that it provides a badly-needed space for diverse writers whose lived experiences need to be heard. I'm proud to continue to support it, albeit now in a much smaller way.
Team Human: Via patronage rather than subscription, I'm proud to support Douglas Rushkoff's work. I was privileged to co-teach a class with him when Known launched in 2014, and we were subsequently namechecked in Throwing Rocks at the Google Bus; his body of work pushes at the important topics at the intersection between tech and society in ways I'm highly aligned with.
The Amazon Chronicles: A weekly newsletter specifically about Amazon. I'm boycotting the company this year because of its involvement in ICE deportations, and it's incredibly hard: it's ingrained into society in a way most corporations could only dream of. Tim Carmody is doing a good job of going deep on this one-company beat. For example: why Amazon and New York are better apart than together.
Hallie Bateman: My last patronage contribution, Hallie's art is exactly the kind of thing I love. Emotionally resonant, whimsical, relatable. (She drew my Twitter avatar.) If you haven't checked out the book she wrote with her mom, What To Do When I'm Gone, you should. But fair warning: I can't remember anything that's made me cry anywhere near as much.