Gregory Carpenter: Beyond the Network | Threat Modeling, AI, and Real-World Pen Testing

In this episode, Phillip Wylie sits down with Dr. Gregory Carpenter to explore his journey from early childhood curiosity to a distinguished career in cybersecurity, military operations, and advanced threat modeling.

Greg shares how his early interest in security evolved from physical lockpicking and unconventional problem solving into work involving digital security, NSA operations, and space-related missions.

The conversation dives into what effective threat modeling really looks like and why too many security assessments fail to account for real-world conditions. Greg explains the importance of looking beyond traditional network boundaries to include physical access, RF exposure, social engineering, environmental conditions, and human behavior. He also discusses the limits of narrowly scoped pen tests and why deeper, more realistic engagement is critical for understanding how attackers actually operate.

Phillip and Greg also examine the growing role of AI and automation in offensive security. Greg shares his perspective on how AI can improve security assessments, where automation adds value, and why creativity and adaptability still matter just as much as tools. They also cover dynamic defenses, deception, critical infrastructure risk, and how organizations can use intelligence sources such as MITRE, DOD, FBI, and DHS to strengthen their defensive strategies.

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Connect with Gregory Carpenter:

LinkedIn: https://www.linkedin.com/in/gcarpenter-cso-kbi/

Gregory's book: https://www.amazon.com/Reverse-Deception-Organized-Counter-Exploitation-McGraw-Hill/dp/B00E6T3VRA/

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Connect with your host, Phillip Wylie:

LinkedIn: https://linkedin.com/in/phillipwylie

X: https://x.com/PhillipWylie

Instagram: https://www.instagram.com/phillipwylie