There are unique challenges to developing and mentoring communities of practitioners whose jobs are, by design, intended to skirt laws and bypass security systems. As such, there are bizarre similarities between the hacking and the special operations communities. Nina (an analyst of military technology and infosec) has been attempting to norm a very reluctant special operations officer (Paul) into the community. Paul, as a career officer in the special operations community has endured several ShmooCons and at least one BSides. Together we present the contrast and similarities of the people/threat landscape/and professional development challenges and what the two communities can learn from one another–namely a deeper understanding of what it is like to develop and mentor intelligent deviants.