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Explore the unique challenges and similarities between the hacking and special operations communities in this insightful conference talk. Delve into the complexities of mentoring and developing practitioners whose roles involve circumventing laws and security systems. Gain valuable insights from Nina Kollars, an analyst of military technology and infosec, and Paul Brister, a career special operations officer, as they discuss the contrasts and parallels in people, threat landscapes, and professional development challenges. Discover what these two communities can learn from each other, particularly in understanding the nuances of nurturing intelligent deviants. Examine the process of integrating a special operations officer into the infosec community and the resulting observations. Learn about horizontal knowledge transfer and adaptive behaviors in both fields, offering a unique perspective on mentorship and community development in unconventional professional environments.