You're thinking of putting aside 3 years of experience in Rails and Ruby in order to learn a new language + framework. On a project that you're taking friends

You're thinking of putting aside 3 years of experience in Rails and Ruby in order to learn a new language + framework. On a project that you're taking friends and family funding for. While it's easy to pick up a language or framework, you only pick up best practices by constant usage and community involvement. How are you going to assess the Python and Django competency of your hires if you're that new to a language? How will you make competent estimates for a technology unfamiliar to you? Both frameworks have been successfully used to rapidly prototype web apps. When you say "make the right technology decision", that is always defined by context. And in your context you have 3 years of experience in one, and 0 in the other. Unless the new technology is demonstrably far superior to the incumbent one, you'll probably be better served by going with what you know. Note that my answer would be the same if Rails and Django were reversed in your post.