The challenge: you have to explain TypeTheory to a typical batch of programmers and software engineers who are hearing TypeTheory for the first time. It has to fit on 2 sheets of paper with inch margins on all sides and using a 12-point Times or Times New Roman font (or assume the default Wiki font).
Explaining it in two pages is not at all difficult. Explaining it so that it'd both be theoretically correct and so they'd understand it, OTOH... not likely. It'd be at least as hard as explaining the mechanism AND application of Calculus to people who haven't yet taken Trigonometry, and even that may be quite generous... do these guys have Masters degrees? or are they out-of-highschool programmers?
Explaining it in loose terms, at the 5000 foot view, though, would be far easier, especially if there is a particular goal (e.g. understanding how types relate to a programming language they are going to be using). I'll consider getting on it when I find TimeToMakeItShort.