Ruby/Rails is predominant in the startup world now. Regardless of the language you're probably going to want to build something for show and tell as soon as you

Ruby/Rails is predominant in the startup world now. Regardless of the language you're probably going to want to build something for show and tell as soon as you can. You can host on Heroku and of course having viewable code on GitHub is important, too (how about a simple finance-related library culled from your experience?). There was discussion earlier this year about the Great Chicago Ruby Developer Shortage, so that may be an option (and of course SF if you're really willing to move). Sometimes I think startups undervalue experience while over-emphasizing open source contributions; however the flip side is they're more likely to give someone with less experience a chance if they can see some code, especially in big cities with the most demand. Good luck!