PODCAST · technology
The Virtual CISO Moment
by Greg Schaffer
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
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S8E25 - From Help Desk to Enterprise Security with Travis Stein
In this episode of The Virtual CISO Moment, Greg Schaffer welcomes Travis Stein, a security engineer whose journey from IT help desk to leading enterprise security programs offers valuable lessons for cybersecurity professionals at every stage of their careers. Travis shares how burnout led him…
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S8E24 - Andrew Kalat: What Cybersecurity Can Learn from Aviation
In this episode of The Virtual CISO Moment, Greg Schaffer welcomes cybersecurity veteran, consultant, author, podcaster, and private pilot Andrew Kalat for a wide-ranging discussion spanning more than three decades in information security. Andrew shares his journey from the early days of bulletin...
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S8E23 - Bruno Lecoq on AI, CMMC, and SMB Security
In this episode of The Virtual CISO Moment, Greg Schaffer welcomes Bruno Lecoq, Co-Founder, CEO, and CISO of BEMO, for a wide-ranging conversation on Microsoft's evolving security ecosystem, CMMC compliance, and the realities of securing small and midsized businesses. Drawing on nearly two…
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S8E22- Alan Clinard Discusses Building Security Programs That Actually Work
In S8E22, Greg Schaffer sits down with Alan Clinard, founder of Athena vCISO Services, to explore what it really means to be a trusted security advisor. Drawing from a career that spans the U.S. Army, operational risk consulting, banking, critical infrastructure, and virtual CISO services, Alan...
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S8E21 – Cy Sturdivant on Community Banking, Risk, and Cyber Leadership
Cy Sturdivant returns to the Virtual CISO Moment to share lessons from more than two decades in cybersecurity, financial services, and consulting. The conversation explores the importance of professional relationships, security program maturity, AI adoption in banking, and why organizations that...
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S8E20 – Becky MacDonald on Building Security Beyond Compliance
In this episode of The Virtual CISO Moment, Greg Schaffer sits down with cybersecurity leader and Cyber Risk Navigator founder Becky MacDonald to discuss the evolution of cybersecurity leadership, the realities of virtual CISO work, and why effective security programs must be built around…
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S8E19 - Cybersecurity, Community, and Leadership with Jonathan Weaver
In this episode of The Virtual CISO Moment, Greg Schaffer sits down with Jonathan Weaver to discuss the evolving role of governance, risk, and compliance in today’s cybersecurity landscape. Jonathan shares his journey from the University of Tennessee into cybersecurity consulting, the lessons he...
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S8E18 – Why Identity Is the Future of Cybersecurity with Jackie Shoback
In this episode, Jackie Shoback—Co-Founder of 1414 Ventures and seasoned C-suite leader—joins Greg to explore how cybersecurity has evolved from a back-office IT function into a core business strategy. Drawing on decades of experience across enterprise and financial services, Jackie breaks down…
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S8E17 - Mid TN ISACA Conference Chats
At the 2026 Middle Tennessee ISACA conference I had the chance to sit down for short chats with a few information security pros: India James, who spoke on the importance of security and digital trust at the conference; Ken Smith, Director of Sales Engineering Enterprise for the Great Lakes at...
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S8E16 - Real-World CMMC Insights with Rich Bates
Rich Bates shares a candid look at his 30+ year journey into cybersecurity, from early computing days to leading GRC programs and now building his own advisory practice focused on helping organizations tackle CMMC and compliance challenges. Along the way, he breaks down why these frameworks…
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S8E15 – The Modern vCISO Journey with Joseph Gunnells
What does it really take to evolve into a modern vCISO—and why does it matter more than ever? In this episode, Joseph Gunnells shares his journey from early technical roles to a strategic governance, risk, and compliance leader, revealing how real-world experience—not just certifications—shapes...
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S8E14 - The Reality of Starting a Cyber Business with Robert Duchesne
From firefighter aspirations to securing the defense industrial base—this episode of The Virtual CISO Moment dives into a career path that didn’t follow the plan… and turned out better because of it. Robert Duchesne shares how a pivot from the Air Force into cybersecurity led him to supporting...
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S8E13 - Smarter Security, Fewer Tools with Jason Makevich
In this episode of The Virtual CISO Moment, Jason Makevich shares his journey from MSP roots to building Greenlight Cyber and PORT1, along with his mission to simplify cybersecurity for SMBs. He unpacks the problem of “duct tape on duct tape” security—where too many tools create complexity…
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S8E12 - Winning the AI Job Market with Angelle Ferrer
Most cybersecurity professionals don’t have a talent problem—they have a visibility problem. In this episode of The Virtual CISO Moment, Greg Schaffer sits down with Angelle Ferrer to unpack why even highly qualified professionals are struggling to get noticed in today’s AI-driven job market.…
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S8E11 - Cyber Threat Intelligence Insights with Travis Whitesel
Cybersecurity isn’t just about technology—it’s about mindset, risk, and understanding where organizations are truly vulnerable. In this episode of The Virtual CISO Moment, host Greg Schaffer sits down with cyber threat intelligence professional Travis Whitesel to explore the evolving intersection...
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S8E10 - AI Governance and the Future of Security with Jack Rumbaugh
Cybersecurity leaders often struggle to translate technical risk into something the business actually understands. In this episode of The Virtual CISO Moment, Greg Schaffer sits down with Jack Rumbaugh, an experienced CISO and virtual CISO with a background spanning telecommunications…
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S8E9 - Jeremy Krienke on Risk, Resilience, and vCISO Work
Jeremy Krienke, founder and CEO of Sidewalk Security Advisors, shares his journey from early threat intelligence work alongside federal partners to leading security programs in banking and fintech—and ultimately launching his own advisory firm. In this episode, Jeremy and Greg explore what it...
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S8E8 - Ransomware Realities with Chris Kimpland
In this episode of The Virtual CISO Moment, Greg Schaffer sits down with Chris Kimpland, CEO of Velocity Incident Response, a service-disabled veteran-owned firm specializing in digital forensics and incident response A former U.S. Army combat engineer, Chris has led hundreds of ransomware...
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S8E7 - Governing the AI Explosion with Dr. Natalia Semenova
In this episode of The Virtual CISO Moment, Greg Schaffer sits down with cybersecurity architect Dr. Natalia Semenova for a deep dive into the evolving world of AI risk and security architecture With a Ph.D. in applied mathematics and experience spanning Google, Microsoft, Mercedes-Benz, and...
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S8E6 - Passing Audits Isn’t Security with Mariia Erokhina
What does real security maturity actually look like—beyond checklists and audits? In this episode of The Virtual CISO Moment, Greg Schaffer sits down with Mariia Erokhina, a global security leader who challenges the industry’s obsession with controls and compliance theater. Mariia shares why...
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S8E5 - Order to Chaos: Cyber Risk and AI Governance with Scott Foote
In this episode of The Virtual CISO Moment, Greg Schaffer talks with cybersecurity veteran Scott Foote about what hasn’t changed in cyber risk over the last 35 years—and why AI is amplifying those same mistakes at unprecedented speed. They discuss shadow AI, insecure defaults, “vibe coding,”...
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S8E4 - Offensive Security in the Age of AI with Mike Gropp
In this episode of The Virtual CISO Moment, Greg sits down with Mike Gropp to explore an unconventional journey into cybersecurity—from entrepreneurship and living in China to offensive security and red teaming. The conversation dives deep into the real-world risks of “vibe coding,” AI-driven...
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S8E3 - Cyber Risk, Business Reality, and Leadership with Tatiana Argueta
How do you explain security risk to executives who don’t speak “security”? What really changes when you move between regulated industries like healthcare and energy? And why are communication skills just as critical as technical ones in cybersecurity? In this episode, Greg Schaffer speaks with...
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S8E2 - When Ransomware Gets Real: Zach Lewis on Surviving a LockBit Attack
What happens when a routine IT problem turns into a full-blown ransomware crisis? In this episode of The Virtual CISO Moment, Greg Schaffer sits down with Zach Lewis, CIO, CISO, and author of Locked Up, to explore the reality of leading through a LockBit ransomware attack—without the benefit of...
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S8E1 - Offensive Security in the Age of AI with Corey LeBleu
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...
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S7E55 - Five Security Trends That Will Force Hard Conversations in 2026
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…
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S7E54 - Cutting Through the AI Hype: Practical Security with Logan Edmonds
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...
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S7E53 - A Conversation with Thomas Sweet
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...
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S7E52 - A Conversation with Chuck Anderson
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...
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S7E51 - A Conversation with Dave McKenzie
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...
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S7E50 - A Conversation with Peter Gregory
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…
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S7E49 - A Conversation with Patrick Rost
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…
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S7E48 - A Conversation with Walter Haydock
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…
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S7E47 - A Conversation with Students
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...
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S7E46 - A Conversation with Andrew Staton
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...
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S7E45 - A Conversation with Brad Mathis
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…
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S7E44 - A Conversation with Christopher Carter
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...
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S7E43 - A Conversation with Wesley Widner
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…
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S7E42 - A Conversation with Michael Scheidell
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…
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S7E41 - A Conversation with Dylan Owen
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…
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S7E40 - A Conversation with Keith Walker
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,...
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S7E39 - A Conversation with Samuel Hill
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...
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S7E38 - A Conversation with Jason Jauch
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…
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S7E35 - A Conversation with Harris Schwartz
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.…
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S7E34 - A Conversation with Butch Rutt
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...
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S7E37 - A Conversation with Nick Eicken
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...
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S7E36 - A Conversation with Stacy Mill
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…
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S7E33 - A Conversation with James Phan
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...
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S7E32 - A Conversation with Mick Grayson
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...
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S7E31 - A Conversation with Wil Klusovsky
In this episode of Security Conversations from The Virtual CISO Moment, we’re joined by Wil Ku, a seasoned cybersecurity leader with deep expertise in risk management, security strategy, and governance. With a background that spans both public and private sectors—including leadership roles at top...
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ABOUT THIS SHOW
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.
HOSTED BY
Greg Schaffer
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Frequently Asked Questions
How many episodes does The Virtual CISO Moment have?
The Virtual CISO Moment currently has 530 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is The Virtual CISO Moment about?
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...
How often does The Virtual CISO Moment release new episodes?
The Virtual CISO Moment releases new episodes frequently with a large back catalog of 530 episodes. Check the episode list for recent publication dates.
Where can I listen to The Virtual CISO Moment?
You can listen to The Virtual CISO Moment on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts The Virtual CISO Moment?
The Virtual CISO Moment is created and hosted by Greg Schaffer.
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