Penetration testing (pentesting) is a fascinating part of information security.  Part hacking, part social-engineering, and part performance art.  What does a pentester's day look like when they are testing a company's security?  How do they start?  What do they do, step-by-step?  This podcast episode is an excellent peek into the life of a pentester that was hired to conduct a double-blind test.  

It is a captivating story and worth checking out.  Notice how the more roadblocks that are in place to frustrate an attacker the more they will need to take increasingly risky actions which will then increase their risk of detection.