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 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.
Greg Schaffer welcomes Butch Rutt, Campus Security Supervisor at Littleton Public Schools, for a powerful conversation on leadership, service, and school safety. Drawing from his background in the U.S. Army and over two decades in law enforcement, Butch shares how his experiences inform a people-first approach to security. From crisis response to building trust with students and staff, this episode highlights the balance between vi...
Nick Eicken is the founder of CyberAuthority and a seasoned Virtual Chief Information Security Officer (vCISO) with deep roots in both military and civilian cybersecurity leadership. A U.S. Army veteran who built top-secret communication networks as a signal officer, Nick transitioned to the private sector where he’s guided organizations across nonprofit, manufacturing, government, and consulting spaces. His firm, CyberAuthority, f...
From the Middle Tennessee ISACA Conference, Cool Springs, Tennessee, March 2025.
Stacy Mill is a seasoned cybersecurity and IT executive with a track record of leading complex technology initiatives in both the public and private sectors. She has served as CTO for the State of Kansas, VP of IT and CISO at Nashville Electric Service, and global CISO at major enterprises like Spirit AeroSystems and Yum Brands. Stacy is also an act...
In this episode, Greg Schaffer interviews James Pham, CEO and co-founder of Opsin, who shares his unique journey from chemistry medalist in high school to tech entrepreneur. James discusses how his academic and professional path took him from studying in Korea and working in Singapore to pursuing his entrepreneurial dream in the U.S., eventually earning a spot at MIT where he taught machine learning. He later joined Abnormal Securi...
In this episode of Security Conversations from The Virtual CISO Moment, Greg Schaffer sits down with Mick Grayson, a seasoned cybersecurity professional with a wealth of experience in both the public and private sectors. Together, they explore the evolving challenges of managing risk in an increasingly complex threat landscape, the importance of mentorship in cybersecurity leadership, and how small and midsized organizations can bu...
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