He gave us a bit of a run-through presentation of his tactics for the latest shmoocon CTF. It seemed like it was a combination of time, skill, more time, patience... and skill? The world of reversing is so beyond my ken, but I love having people around who know how to do it.
When I asked how to get started, he suggested I just jump into a CTF and try.
[edit] I work at endgame (see my other comment), we're hiring, etc. etc.