At SourceBoston 2009 fellow New Yorker Dan Guido did a talk entitled “So You Want to Train an Army of Ninjas”. Dan’s talk was on his experience organizing the CSAW competitions at NYU:Polytechnic. If you are unfamiliar with the annual awesomeness that the ISIS program at NYU:Poly puts together, you can read more about the whole event here. To quote someone on twitter “If all of school was like [the program at NYU:Poly] maybe I wouldn’t have dropped out.”
This is a good read. I still think teaching yourself these skills as opposed to 'learning' them is a vital step.
Matasano Security LLC - Chargen - Exercises for a burgeoning Army of Ninjas