Ask HN: Next Step for CIO Turned Bootstrapper/RoR Dev?

Looking for a bit of career advice. I started back in '99 as a developer, and was fortunate to make my way to CIO of a small IT service company. I like people, understanding businesses and how technology can help, and I always kept my fingers dirty in tech, but never really hardcore development.

Four years ago I decided I wanted to build software products, so I left for an opportunity with the federal govt b/c I knew it would provide me with the flexibility and income needed to still support my family while working on the side to build products.

I've build a few SaaS apps on the side, picking up some RoR along the way, but after 4 years of working in the govt, I'm losing my mind and am looking to leave and work back in private industry/for a startup, but am unclear on what I might essentially be qualified to do. In other words, I've got a well-rounded 14-year career, good at what I know/do but only have 3 years of RoR experience.

So my questions are these: Is it worth reaching out to companies offering to volunteer my skills in an effort to learn/solidify my skillset, or am I better off spending the next few months working on the fundamentals and then trying to make the leap out? Aside from focusing on RoR, any thoughts on where someone with my type of background might fit in?

Thanks for your time and assistance.