When Cyber Security collides with AI

Keith Gologorsky, Head of Public Sector at Hack the Box, shares his personal journey from computer science graduate to government analyst, recounting pivotal moments in military operations, threat analysis, and international collaboration. The discussion explores the limitations of traditional certifications, the importance of hands-on training, and the need for regularly updated, gamified learning experiences. Keith also addresses the cybersecurity skills gap, the evolving role of AI, and offers actionable advice for organizations of all sizes: prioritize cross-training and real-world practice to build resilient teams.

Sarah Flukes, CTO at Admeritia, explains cyber decision diagrams that capture how OT/ICS environments actually operate. This podcast covers origins in water utilities, why function modeling beats asset lists, cognitive effectiveness, and how these diagrams power risk assessments, incident response, and security-by-design.

Cyber & AI authority Chuck Brooks joins Jeff Edwards to give SMBs a no-nonsense playbook. Learn how agentic AI turbocharges phishing, why unmanaged IoT/OT opens doors, and the exact first steps—MFA, segmentation, backups, IR plan—that raise your resilience fast. We also cover using NIST and CMMC as practical roadmaps and when to rely on an MSP.

Erik Cernak of the Hanover Insurance Group, breaks down the myths, the market, and the must-dos of why only 4% of SMBs carry standalone cyber insurance.

Our Cyber Insurance Summer Series wraps with the biggest lessons learned, surprising insights, and actionable advice from our expert guests. This episode ties everything together for the SMB with concrete steps that can be taken today to protect your business.

Ted Brown provides an expert legal perspective on cyber claims, discussing how they are far more complex than traditional insurance claims due to a multitude of moving pieces. He highlights common coverage disputes, such as late reporting and application issues, and stresses that cyber insurance is meant to bring a business back to where it was, not to “make them better.” Ted advises that the single most important step for any business is to work with their insurer and legal counsel as soon as an incident occurs, as this can prevent massive headaches and ensure a smooth recovery.