Cybersecurity and AI for Small Businesses: Expert Insights with Chuck Brooks

Season 3 /
/Episode 2

Cybersecurity and AI for Small Businesses: Expert Insights with Chuck Brooks

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.

Resources: Free guides/checklists: SafeHouseInitiative.org (no tracking, no fees)
Guest: Chuck Brooks
Host: Jeff Edwards

🎬 Production Team: Alan Gin – Executive Producer Jen Carpenter – Editor & Post Production Supervisor Keith Fukuhara – Production Manager & Technical Director Dorian Naveh – Marketing & Social Media Manager

#️⃣ Hashtags (place first 3 above the title): #CyberSecurity #SMB #AI #Phishing #MFA #ZeroTrust #CMMC #NIST #IoT #OTSecurity #RiskManagement #BusinessContinuity #IncidentResponse #SafeHousePodcast

When Cybersecurity Became a State Responsibility with James Saunders

Federal cybersecurity responsibility has shifted to the states. What happens next?

In this episode of The SafeHouse Podcast, Jeff Edwards welcomes James Saunders, Chief Information Security Officer for the State of Maryland, for a deep conversation on state-level cybersecurity, resilience, and leadership.

James walks through his path from early technical support roles to federal cybersecurity leadership and now to protecting Maryland’s digital ecosystem. He explains Maryland’s IT Master Plan, the state’s five-pillar cybersecurity strategy, and how partnerships, talent, and resilience come together in practice.

This episode offers a behind-the-scenes look at how cybersecurity decisions are made at scale, how states collaborate with one another, and why taking care of people matters as much as taking care of systems.

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Why Cyber Warranties Are Not Insurance — and Why That Matters

Kirsten Bay, CEO and co-founder of Cysurance, explains why warranties are becoming a critical layer in cyber risk management. Bay explains how AI-driven cyber certification can help organizations predict where risk is most likely to surface, prevent disruption before it becomes a claim, and protect both insureds and carriers by creating clear, defensible signals of cyber maturity.

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Cybersecurity Frameworks Made Practical: From Confusion to Clarity

Ryan Ettridge, CEO of CyberCert, tackles a problem many organizations struggle with – cybersecurity frameworks that look good on paper but feel overwhelming or unusable in practice.
Ryan explains how AI-driven cyber certification can help organizations predict where risk is most likely to surface, prevent disruption before it becomes a claim, and protect both insureds and carriers by creating clear, defensible signals of cyber maturity.
Chart a clear path from path from compliance to real-world readiness with fundamentals covered in this episode.

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From Bootcamps to Battlefields: Keith Gologorsky on Modern Cyber Training

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.

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