The Virtual CISO Moment
The Virtual CISO Moment dives into the stories of information security, information technology, and risk management pros; what drives them and what makes them successful while helping small and midsized business (SMB) security needs. No frills, no glamour, no transparent whiteboard text, no complex graphics, and no script - just honest discussion of SMB information security risk issues. Brought to you by vCISO Services, LLC, a leading provider of vCISO and information security risk management services. Visit https://vcisoservices.com to learn more. A Second Chance Publishing, LLC podcast.
Episodes
In the Season 8 premiere of The Virtual CISO Moment, host Greg Schaffer sits down with Corey LeBleu, Founder and CEO of Relix Security, to explore how offensive security and penetration testing are evolving in a world shaped by cloud platforms, AI, and “vibe coding.”
With more than two decades of hands-on experience in application and network penetration testing—including leadership roles at Verizon and boutique consultancies—Corey ...
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...
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 appr...
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 tra...
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 prepar...
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...
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 ...
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 secur...
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.
Recently The Virtual CISO Moment podcast host Greg Schaffer was asked to participate in a question and answer session with students at Minnesota State University who are using his book Information Security for Small and Midsized Businesses as part of their studies. In this special and extended episode, a recoding of that conversation, they talk about concerns of small and midsized businesses and the outlook for the information secu...
In this inspiring and deeply personal episode of The Virtual CISO Moment, Greg Schaffer sits down with cybersecurity professional Andrew Staton to discuss his journey from high school CyberPatriot competitions in Huntsville to federal cybersecurity consulting.
Topics Covered:
How local cyber education programs launched Andrew’s career
The evolving landscape of CMMC and compliance misconceptions
Why data scoping is key for affordabl...
In this episode of The Virtual CISO Moment, Greg Schaffer welcomes Brad Mathis, Senior Information Security Consultant at Keller Schroeder, for a wide-ranging discussion that spans four decades in technology and cybersecurity.
From his early days repairing computers and catching his first virus, to leading security teams and serving as a virtual CISO, Brad shares a wealth of real-world experience and insights.
Key highlights include:
...In this episode, Greg Schaffer welcomes Christopher Carter, Chairman and CEO of Approyo, for a dynamic conversation about SAP, cybersecurity, and leadership. Chris shares his journey from early days at Coca-Cola to building a successful SAP consulting business, discusses key risks in SAP environments, and explores how AI is shaping threat detection. From monitoring legacy systems to helping clients bounce back from breaches, Chris ...
On this episode of The Virtual CISO Moment, Wesley Widner shares his inspiring journey from law enforcement to cybersecurity, emphasizing the power of networking, authenticity, and a lifelong learning mindset.
Wes founded White Hat Wes Cybersecurity to help others break into the field by providing a free platform for sharing blogs, projects, and cyber resources—fostering community and mentorship.
He highlights the importance ...
In this episode of *The Virtual CISO Moment*, Greg **Schaffer** sits down with Michael Scheidell, CISO of Security Privateers and Managing Director of Team One Support. Michael shares his unconventional path from robotics to cybersecurity, lessons learned from building companies, and why real-world experience matters more than certifications. He also opens up about stress, service, and his passion for helping veterans transition in...
In this episode of The Virtual CISO Moment, Dylan Owen shares his journey from webmaster in the 1990s to leading cybersecurity teams at Raytheon and serving as CISO at Nightwing. He reflects on the challenges of transitioning into executive leadership, the realities of the vCISO role, and how SMBs can best approach detection and response. Dylan also offers insights on making security frictionless, plus how he manages stress with fi...
In this episode of The Virtual CISO Moment, Greg Schaffer talks with Keith Walker, System Administrator at Nephrology Associates of Northern Illinois and Indiana (NANI), about his unique path into IT, sparked by inheriting his late stepfather’s tech gear. Keith shares how building a home lab, securing a static IP, and hands-on tinkering shaped his career, and discusses the challenges of balancing operational efficiency with securit...
In this episode of *The Virtual CISO Moment*, Greg Schaffer sits down with Samuel Hill, Senior Director of Product Marketing at Mind, to explore how authentic, empathy-driven marketing can cut through cybersecurity’s buzzwords and truly connect with practitioners. Hill shares his journey from the ER to the startup world, the power of storytelling in building trust, and why the industry is shifting from compliance checkboxes to real...
In this episode, Greg talks with Jason Jauch, founder of C^2, about the challenges and rewards of delivering cybersecurity to healthcare practices. Jason shares his journey from hands-on IT to virtual CISO, why compliance doesn’t equal security, and how his one-stop-shop model helps clients manage risk without the noise. They also discuss upcoming HIPAA changes, niche security gaps in ophthalmology, and how Jason stays grounded thr...
Greg Schaffer sits down with Harris Schwartz, Founder of vSecurity Advisor and seasoned cybersecurity executive. With over 30 years in the field, Harris shares his journey from the dawn of the public internet to advising organizations on building risk-based, business-aligned security programs. Tune in for insights on leadership, mentorship, and creating a resilient cybersecurity culture.
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