In this special episode of The Virtual CISO Moment, Greg Schaffer shares five cybersecurity predictions for 2026 grounded in real-world patterns — not hype. From the tightening of SOC 2 audits and the rise of “vibe coding” risks, to a coming shakeout in the vCISO market, influencer-driven security shaming, and the growing dangers of contractor misclassification, this episode explores the second-order consequences many organizations are already overlooking.

If you’re a business leader, CISO, or vCISO, this episode will challenge assumptions and help you see where governance failures quietly become security failures.

In this episode of The Virtual CISO Moment, Greg Schaffer sits down with Logan Edmonds, Chief AI Officer at ScaleSight and founder of TTS Cyber, for a lively and insightful discussion on the intersection of AI, cybersecurity, and small to mid-sized business operations. Logan shares his unique journey from studying theology to becoming an AI-driven cybersecurity leader, highlighting how early IT experiences shaped his pragmatic approach to solving business problems.

Greg and Logan dive deep into how SMBs misunderstand both security and AI, including the dangers of chasing trends, the misconception that compliance equals security, and why AI can’t magically fix broken business processes. Logan emphasizes a business-first mindset: start with understanding operations, outcomes, and risks—not with the technology.

The conversation also covers:

• Why focusing on operational efficiency is the real driver behind meaningful AI adoption

• How to talk about risk without falling into fear, uncertainty, and doubt

• The importance of trust and partnership in security consulting

• Realistic AI use cases, guardrails, hallucination risks, and the myth of effortless automation

• Balancing stress in cybersecurity through healthy personal hobbies

• Logan’s forward-looking plans in CMMC, AI strategy, and helping organizations scale responsibly

Engaging, humorous, and packed with practical insight, this episode is a must-listen for leaders navigating AI adoption, cybersecurity maturity, or the unique challenges of SMB environments.

In this episode, host Greg Schaffer interviews Thomas Sweet, an award-winning CIO/CTO and 2023 Tech Titan Emerging CTO, who shares his unconventional journey from civil engineering to enterprise IT and cybersecurity leadership. Tom reflects on his early days at NEC, Microsoft, GM Financial, and more, offering key lessons learned while leading global teams and driving digital transformation.

The conversation covers:
🔹 How Tom transitioned from civil engineering into IT
🔹 The problem-solving mindset engineering instilled in him
🔹 His approach to building strong, low-attrition teams through genuine leadership
🔹 Why AI is already reshaping IT—and why resisting it may hinder career growth
🔹 How he uses AI to accelerate secure coding, automation, and testing
🔹 The emerging landscape of AI-specific attacks
🔹 The importance of decompression and how Tom balances life outside technology

A thoughtful, engaging look at technology leadership, organizational culture, and the rapidly changing role of AI in the enterprise.

This Thanksgiving-week episode welcomes back Chuck Anderson, IT consultant at Reliant Managed Services, for a deep dive into some of the biggest shifts in cybersecurity and technology over the past year and a half. Chuck and Greg explore the rapid rise of AI (good and bad), the looming disruption of quantum computing—especially its impact on encryption and certificates—and the operational realities organizations face as they prepare for a post-quantum world.

They also dig into change management, why empathy matters more than ever in cybersecurity, and how tech pros can better communicate and lead through major transformation. A forward-looking, practical, and enjoyable conversation for anyone navigating today’s evolving cyber landscape.

In this episode of The Virtual CISO Moment, host Greg Schaffer speaks with Dave McKenzie, co-founder and director of Damn Good Security and a seasoned cybersecurity leader based in Scotland.

Dave shares his fascinating journey from aspiring pilot to IT support technician, to leading security operations for major organizations, and ultimately launching his own company. His path, driven by curiosity, adaptability, and a dislike of handwriting, reveals how technical expertise and communication skills blend to form a truly effective security professional.

This wide-ranging conversation is packed with humor, practical insights, and wisdom for anyone in the cybersecurity field.

In this episode of The Virtual CISO Moment, Greg Schaffer welcomes back cybersecurity expert and best-selling author Peter H. Gregory — who’s written over 50 books and helped shape many of today’s top security and certification programs.

They dive deep into:

💡 AI Governance — how to use AI safely, ethically, and legally (and why “shadow AI” may be your biggest unseen risk)

📚 Publishing Your Technical Book — Peter’s step-by-step insights from idea to printed page

⚙️ Data Governance & Privacy — why strong data management is essential before implementing AI

Peter also shares details on his upcoming AI Governance Professional (AIGP) study guide and offers timeless advice for aspiring cybersecurity authors.

🎧 Tune in for expert perspectives, practical insights, and a few laughs along the way.

#Cybersecurity #AIGovernance #vCISO #DataPrivacy #InfoSec #PeterHGregory #GregSchaffer #VirtualCISOMoment

Patrick Rost, owner and advisor at InfoSecurity Blueprint, joins Greg Schaffer to discuss his journey from a technology enthusiast to an information security entrepreneur. Patrick shares insights on helping small and midsized businesses take their first steps toward better security—emphasizing that information security is about managing business risk, not just technology.

He explains his “wash one dish” approach to simplifying security, why “InfoSecurity” matters more than “Cybersecurity,” and how fractional advisory services can empower organizations without overwhelming them.

The discussion also explores AI governance for small businesses, risk-based thinking, and how to make security engaging—even fun—for executives.

Walter Haydock, founder of StackAware, joins Greg Schaffer to discuss how AI-powered companies can manage cybersecurity, privacy, and compliance risks using the ISO 42001 AI governance framework.

Learn why AI literacy matters, what organizations can learn from Amazon’s AI missteps, and how to make smarter risk decisions in the age of generative AI.