Like many Rubyists, I've spent untold dollars on books and screencasts (we must be a very lucrative bunch on a per-user basis), and when it comes to Ruby, I've got money burning a hole in my pocket.
Now, the question is, will we Rubyists also contribute $$$ toward Ruby development? I think a great many of us would. Personally, I can donate $15 per month, and would be happy to do so. I would think that many profitable startups who are invested in Rails/Merb/Sinatra would be very interested as well. With enough of us, we could probably throw a lot more bright minds at the tough implementation problems Ruby faces.
I must admit I'm out of my depth when it comes to the brass tacks of starting foundations, but it seems to me that Ruby is ripe for one (python.org, anyone?). I'm feeling a bit frustrated that with all my love for Ruby, I can't even contribute my cash toward Ruby advocacy and development. And who doesn't want free cash? Am I alone in my thinking? Is there a website where this is already being done? If not, doesn't that signal a fundamental problem?
Let's put the market to work and kill this already!