Free as in freedom, not beer. Ask for beer and give freedom in return.
I have this idea in the back of my head. Where I live in Japan, in the countryside they just put up these vegetable stalls. Nobody is there. There is a box and on it is say "100 yen" (about 1 dollar US). There are bags of fruit and vegetables. You take a bag and you put a 100 yen coin in the box. Not rocket science and nobody who isn't starving won't put the coin in (and if you are starving, take the damn fruit!)
You don't need leverage, you need it to be the norm that people pay for the software. That requires a cultural shift. Luckily, community cultures can be crafted (I think... maybe I'm wrong). People need to feel that if they pay for the software, you will make more (which they want). If they don't pay for the software, you will not make more (which they do not want). I think that's all it probably takes to earn money at this. I think... One day I'll test that theory.
This is the case for consumer software. I am not even trying to imagine how harsh it would be for an open source maintainer - who has absolutely no leverage given the source is already out there. What’s happening with docker, elasticsearch, Redis, MongoDB et al is not giving me hope either.
There's definitely a startup opportunity for this - making it super easy to receive payment as an OSS developer (either as a business or sole developer) and making it easy for businesses to pay.
If I saw a new issue on github and it came from a corporate "OSS gold account member" which potentially comes with $$$ attached I'd be much more inclined to implement it.
As it is my motivation drops off fairly quickly unless it's a serious bug or it's a relatively easy ask.
I think it would be much easier to get budget if the cost to get expedited OSS bugfixes were subscription based and accounts gets to deal with a professional billing department rather than "One Man and His Hat Inc. in Iowa".
GitHub is the de facto hub of open source/free software, and if it was as easy to donate to a repo as it is to star it, I imagine more people would do it.
(seriously, there is a difference between a day job programmer, and a lifestyle programmer)
- Ask for donations
- Ask commercial users to pay a fee (still voluntarily though)
- Offer yourself as a consultant on the software, you can help businesses with implementation or migration.
Of course, there is a thin line. Having people to pay for your software raises expectations. Also, paying customers could steer you into a direction you (or the FOSS community) don't like.
In my experience, almost all businesses are perfectly willing to pay for the software that make their business possible. Businesses understand that FOSS is free speech, not free beer.