I started along the same path 12 years ago, so I can share my experience. * I started with PHP. My suggestion today is to start with Django (Rails is fine too,

I started along the same path 12 years ago, so I can share my experience. * I started with PHP. My suggestion today is to start with Django (Rails is fine too, but Django has less magic and so things are lot more explicit) * Bootstrapping out of nowhere is difficult. He will have a lot to learn from the knowledge perspective. So, looking out for opportunities, negotiating payment etc. can be draining. This is where you can help so that he focuses on learning his craft first. * It will be tempting to work for free. Advice him against that. He can work for a low fee, but getting paid puts the work in the right context. * Stay away from portals like Elance and ODesk. * Working as an intern at a company would really help him with the other meta aspects like planning, team collaboration etc. which are all important to pursue his long-term goals.