The book Working In Public is a good resource for learning more about how open source developers fund their work through sponsors, consulting, etc.

The book Working in Public has a good section about funding models for open source.

Tons! Here are a few casual reads I enjoyed:

* Masters of Doom

* Where Wizards Stay Up Late

* Working in Public

Read the book Working In Public. A big chunk of that book is diving into the various economic models for OSS, covering pros and cons through real world examples.

Not specifically software design, but insofar related books that take the perspective of programmers with unique insights:

- Coders at Work (Seibel)

- Working in Public (Eghbal)

The first one is very entertaining. Read it a couple years ago and found it gives some valuable perspective. The second one is on my reading list, it was recommended around these boards.

Related to software design, there are many. The two that are on my recent list are:

- Software Design for Flexibility (Sussman, Hanson)

- A Philosophy of Software Design (Ousterhout)

I can't comment personally on their content yet, still have to work through those two, but I have zero doubts to learn something valuable. Certainly consider them.

I recently started reading Nadia Eghbal's book, "Working in Public: The Making and Maintenance of Open Source Software" [0]. One point she makes early on is that attracting lots of people to open source projects isn't all that hard; but managing lots of potentially low quality contributions is really hard. See "Hacktoberfest" for an example. [1]

If you pay $X for someone to "resolve" the issue, when they submit a patch that doesn't work, or doesn't follow the style guide, or doesn't fit the software architecture, or is otherwise unsatisfactory, how much time are you going to spend fixing/massaging/arguing? Will it be worth it to answer the jilted contributor who keeps sending "I want my $50!!!!" emails?

Nadia also has a quick 10-minute presentation on some ways you can use money to help open source, but without actually paying for bug fixes. [2]

[0] https://smile.amazon.com/dp/0578675862
[1] https://blog.domenic.me/hacktoberfest/
[2] https://www.youtube.com/watch?v=bjAinwgvQqc