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?