Good God. Whenever I read these, I always get chills down my spine. Part of me wants to do the same, get better at it (I know tiny parts of many things including what is discussed here but not even remotely close to the author), the other one just wonders how does one get so good as to perform all this by themselves. Reverse engineering is beautiful :)
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.
Http://crackmes.de
They have lots of challenges, with difficulty levels going from 1-10, and each challenge has an annotated solution explaining how to crack the program.
Exactly how I feel! It looks awesome, and quite understandable when explained step by step. But I feel that I wouldn't be able to get past the first few steps if I encountered these problems by myself.