One thing I would like to point out, that you probably won't like to hear .. If your purpose is to learn how to "hack" to the point where you can make real web

One thing I would like to point out, that you probably won't like to hear .. If your purpose is to learn how to "hack" to the point where you can make real webapps, you should be aware of two things. 1. You will never become a good hacker if you are only doing it for the money or for the recognition. You have to be able to love the code for the sake of the code itself. You have to be able to see the beauty in the code. Otherwise you will never really understand it. It is the difference between being able to copy a poem out of a book and being able to write a new poem. 2. Assuming you are a true genius, the process will still take you many years. Working hard will not be enough. You will have to learn how to work smart to learn all the stuff you will need to know. If your purpose is to understand hacking to the point where you can better understand technical people so that you can work with them better .. that is a much more realistic and reachable goal. For that I would recommend you start with Ruby or Python and try to make a full-scale production webapp, and from that experience you will learn a lot that will explain how a technical person thinks.