Chasing Entropy Podcast Episode 015: Herding Chaos with Jeffrey Wheatman

In this special "Summer Camp" edition of Chasing Entropy, Dave Lewis sits down with longtime friend and cyber risk veteran Jeffrey Wheatman. From their early DEF CON gooning days to leading board-level security conversations, Dave and Jeffrey explore how cybersecurity professionals navigate entropy—when systems unravel, and chaos creeps in.

Jeffrey, a former VP at Gartner and now a cyber risk strategist, brings 30 years of experience to the mic. They dive deep into the human and organizational aspects of risk management, effective communication with executive leadership, and how the security industry can stop "solutioning" with tech and instead focus on solving real problems.

Key Topics That We Covered:

• From Hardware Store to Cyber Risk Strategist: Jeffrey’s unconventional path into cybersecurity and early lessons learned about clarity, communication, and not working in retail.
• Tech for Tech’s Sake?: Why the obsession with new tools misses the point—and how reframing security in terms of solving business problems is the real game changer.
• Communicating with Boards: Strategies for helping CISOs resonate with executives, plus tips on improving board-level metrics and engagement.
• AI in Cybersecurity: Cautious optimism, practical concerns, and philosophical musings. Both Dave and Jeffrey agree: AI is no silver bullet. But with thoughtful integration and strong scenario planning, it can be a powerful partner—especially for edge cases and pattern recognition.
• Speaking to Your Audience: Whether you're in front of a board or a DEF CON hallway track, Jeffrey shares hard-won lessons about adjusting your message, avoiding condescension, and using metaphors that land.

Memorable Quotes

“Technology is created and put in place to solve problems. Full stop.” — Jeffrey Wheatman“Your execs care about three things: money in, money out, and who gets in trouble when stuff goes sideways.” — Jeffrey Wheatman“AI is overblown and underutilized—both are true.” — Dave Lewis

Where to Find Jeffrey

• LinkedIn: The only “Jeffrey Wheatman”
• Speaking soon at: SANS Security Awareness, ISACA GRC, Black Hat, and PDA PRISM Conference
• Fun fact: At DEF CON, you’ll know him as “Mnkey.”

Listen now, share widely, and join us again next week as we continue Chasing Entropy in a world full of chaos and credentials.

Don’t forget to like, subscribe, and spread the entropy.