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The Django Rest Framework library has taken this very approach [1] offering both corporate and individual monthly subscriptions which is then used to fund development. It appears to be quite successful in that it's allowed the lead developer to work on the project full time (at a salary of £50k [2]).

[1] https://fund.django-rest-framework.org/topics/funding/

[2] http://www.encode.io/reports/february-2017

This. A lot.

I work at a company with less than 500 people and for IT open source is evil.

I've seen people been told by IT to find another software that does the same thing but paid, and we have a law that mandates us to prefer FLOSS when possible...

You can in many cases.