Django and Rails are pretty much equivalent these days in just about every meaningful way. I've gone Django for no other reason than I much prefer Python over

Django and Rails are pretty much equivalent these days in just about every meaningful way. I've gone Django for no other reason than I much prefer Python over Ruby. This is not to say Ruby is a bad language, but I much prefer Python's "one way of doing things" ideology over Ruby's "many ways of doing the same thing". The fact that the "alias" keyword exists in Ruby annoys me to no end. I also get the benefit of using Python outside of web dev, such as with the awesome SciPy stack for statistical analysis. It's a personal preference at the end of the day though. You won't go wrong in either direction really. Finally, don't discount .NET. If you know it well, there's no reason you can't build your own solid startup with it at the foundation. It's been done before. (You're going to have fun trying to figure out what front-end JS libs/frameworks to learn next :)