#173: Cybersecurity Meets Comedy: How Humor Builds Trust

SHOW NOTES:

In this episode, Matt Zaun sits down with Rob Black, Founder & CEO of Fractional CISO, to demystify cybersecurity for growing companies—without the fear-mongering. Rob explains how his team operates as a virtual CISO (security leader) to strengthen programs, enable enterprise sales, and translate “security-speak” into clear business outcomes.

Rob shares why security shouldn’t be priority #1 (sales and delivery come first), how to size up the risk when incidents are low-probability but high-impact, and why humor can drive far more adoption than dry policy memos.

In this episode, they cover:

✅ Prioritization reality: why cybersecurity should be priority 4–5—not 100

✅ Humor that converts: skits, wigs, and why fun content outperforms stoic lectures

✅ LinkedIn as referral fuel: staying top-of-mind vs. hard selling (and why neighbors all know what Rob does)

…and much more.

BIOS:

Rob Black is the founder of Fractional CISO, where he and his team serve as virtual CISOs for companies. A veteran security leader with an MBA from Kellogg, Rob blends operator pragmatism with clear business storytelling, often using humor to drive adoption of best practices.

Matt Zaun is an award-winning speaker and strategic storytelling expert who helps leaders inspire action and drive results through the power of story. He’s the author of The StoryBank, a practical playbook for using narrative to build culture, boost sales, strengthen marketing, and become a dynamic public speaker.