There's a reason hackers tend not to be good at 'high school math' - it's incredibly dull. 90% of what most of us did in class consists of essentially running code, the stuff hackers expect the machine to do for us (so we can concentrate on the real problem.)
I think solving mathematical education for the general population is incredibly hard, I wish Paul Lockhart (http://www.maa.org/devlin/LockhartsLament.pdf, http://news.ycombinator.com/item?id=256176) all the best in his efforts. But I think solving mathematical education for hackers ought to be a little easier. We are eminently comfortable with symbolic languages (consistent, testable ones - I'm not sure if many mathematical notations can make the same claim), and we love problem solving. You'd have thought we'd have a hard time not becoming good at math.
Does anyone have any suggestions? How about a textbook where the methods and proofs are expressed in code, for a start?