In this talk Jon covers the pros and cons of Undergraduate Cyber Security Programs, including what they lack when it comes to Offensive Security. It will then touch on the ethics of teaching College Students hacking and then go on to lay out recommendations and guidelines that educators can utilize or incorporate into their CS programs. It ends with an explanation of why it is so important to start producing white-hats before they graduate and some suggestions/tips for current students pursuing higher education that want to enter the field of Offensive Security. This talk is an opportunity for students and professionals alike to peer into the mindset, skill set, and knowledge required to get hired and be successful as a Penetration Tester aka Whitehat Hacker.