Github, Basecamp, Twitch, Stripe, Square, AirBnB, Shopifly, Cookpad, and many more. All these are very successful site that are using Ruby ( Not necessarily Rails ) and most of them profitable.
If each or them could fund a 20-33% Salary of an additional Core Dev you instantly have 3 - 4 people working on it Full time.
So I have been thinking on this for sometime, It is because the Ruby community and the world as a whole does not want to donate? Or are we lacking someone to push this and ask for some help when needed?
I came to say the same thing.
Its such an obviously good idea. It seems all that is needed is a champion for this cause.
Of those I know both Dropbox and Google have employed Gudio Von Rossum, and various other Python core devs are also employed full time.
Overall it seems that Python is much more community driven than Ruby. Python is interesting in that it has several big camps, including web dev, systems programming/automation, scientific usage, machine learning, etc, and all of these communities are fairly self sufficient but also contribute back to the main language.