I view the Red Pill talk as I do the birds and the bees, drugs and alcohol, finance, etc. I've got a very mature 16 year old that will most likely fly the coop once he graduates from HS in two years.

How do I best prepare him now with the skills to not be taken advantage of out in the big wide world?

If its relevant, he and I are very close. Even though he's challenging me a bit more these days (normal adolescent shit), he listens to me. I don't want him wasting 20 years of his adult life driving the wrong direction, due to the faulty roadmap I was handed at his age.