Risk and Reels: A Cybersecurity Podcast

Hosted by Jeffrey Wheatman

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Jun 2025

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About the show

A podcast for movies. A podcast for cyber talk. A podcast for smart people to say smart things to smart listeners. Hosted by Jeffrey Wheatman, former Gartner Analyst.

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60 recent

June 4, 2025Episode 9143 min

Systemic Cyber Risk: A CISO’s Impossible Task

In this episode, Jeffrey Wheatman sits down with Paul Guckian , former BISO at Lloyd’s of London and author of Systemic Cyber Resilience: Why CISOs Can’t Fix Cybersecurity . They unpack why the traditional security model is broken, how systemic risk is the real enemy, and why putting the weight of an entire ecosystem on a single CISO sets everyone up for failure. From resilient thinking to lessons from fire safety and finance, Paul brings an academic lens—and a pragmatic mindset—to a critical conversation. Link to Paul’s book.

May 28, 2025Episode 9031 min

Phishing for Truth: Fixing the Flaws in Security Awareness

Jeffrey Wheatman sits down with Cary Johnson, founder of Phishbusters Audit and Consulting, to expose the failures of traditional phishing simulations. They discuss why standard metrics fall short, how self-assessment distorts results, and what it really takes to track — and influence — behavioral change in security awareness programs.

May 21, 2025Episode 8935 min

The Accidental CISO

In this episode of Risk & Reels , Jeffrey Wheatman sits down with RJ Friedman, CEO of Dayone Cyber, to talk frameworks, risk, and leadership. RJ shares how his start in sales shaped his approach as a CISO, why CIS 18 remains his go-to, and how mapping frameworks to business goals makes all the difference. It's a sharp, honest look at what makes cybersecurity leadership actually work.

May 7, 2025Episode 8832 min

A Story of Limited Resources

In this episode of Risk & Reels , Jeffrey Wheatman sits down with Craig Taylor, CEO of CyberHoot, to talk about how small businesses are navigating the evolving world of cybersecurity compliance—especially the demanding standards of CMMC. From Apollo 13-style ingenuity to the unintended consequences of regulation, Craig shares a 30-year perspective rooted in psychology, education, and operational realism. Tune in for a conversation that covers limited resources, positive reinforcement, and why now is the time to prepare.

April 23, 2025Episode 8734 min

From Homicide to Hackers: Fixing Cybersecurity’s Broken Model

In this episode, Jeffrey Wheatman sits down with Carter Schoenberg, Chief Security Officer at Soundway Consulting and author of Why Cybersecurity Fails in America . From his unexpected transition from homicide detective to cybersecurity leader, Carter shares hard-earned insights into the failures of our current cyber risk models—and how to fix them. They dive into cybercriminal collaboration, the stagnation of HR and hiring practices, and why security leaders need to learn to “speak CFO.”

April 16, 2025Episode 8636 min

This Isn't the Wolf of Wall Street: Recruitment, Rewired

Richie Lampani—self-proclaimed Chief Recruiter Dude—joins Jeffrey Wheatman to talk about the real state of hiring today. From music industry war stories to navigating post-pandemic expectations, Richie drops insights on transparency, mentorship, and why the “perfect candidate” is a myth. Candid, sharp, and unexpectedly hilarious.

April 9, 2025Episode 8541 min

I Robbed a Bank with a Solar Eclipse

Jayson Street, Chief Adversarial Officer at Secure Yeti, returns to Risk and Reels for a no-holds-barred conversation on hacking human nature, creating teachable moments, and why kindness matters in cybersecurity. From robbing banks during celestial events to sneaky USB exploits involving hearing aids, Jayson shares stories that are as outrageous as they are enlightening. Plus: the power of the pause, avoiding blame culture, and how code words like “rutabaga” can save your family from scams.

April 2, 2025Episode 8432 min

A Confluence of Errors and a Little Help From Friends

In this episode of Risk & Reels , host Jeffrey Wheatman sits down with Ed Gaudet, CEO and founder of Censinet, for an insightful conversation about entrepreneurship, product innovation, and the evolution of cybersecurity in healthcare. Ed shares the winding path that led him to founding Censinet, why listening to customers is a game-changer, and how authentic leadership and human connection have shaped his journey. The two also geek out over company origin stories in film—think Tucker , BlackBerry , and of course, Jobs . With lessons on vision, leverage, and not losing sight of the people you serve, this episode is a must-listen for builders, dreamers, and anyone navigating the fast-moving world of tech and risk.

March 26, 2025Episode 8333 min

Cyber Truths, Intelligence Myths, and Life after the NSA

In this episode of Risk and Reels , host Jeffrey Wheatman welcomes security veteran and former NSA executive Don Boian for a wide-ranging conversation on intelligence, cybersecurity, and life on both sides of the public-private divide. Don reflects on his 30-year NSA career, shares myths about intelligence agencies, and explains how AI is shifting the balance for defenders. He also dives into his work as an expert witness, his boardroom insights, and how introverts can thrive in public speaking and leadership roles. It’s a blend of wisdom, war stories, and actionable advice for anyone in or entering the cybersecurity world. Here's the list of the books Don mentions - Note: He does not endorse or profit from these books. Some have facts, fiction, and a little of both. * Dark Territory * Sandworm * Countdown to Zero Day * This is How They Tell Me the World Ends

March 19, 2025Episode 8229 min

Every Day is a Risk Decision

In this episode of Risk and Reels , host Jeffrey Wheatman sits down with seasoned cybersecurity leader Kimberly Trapani to discuss the evolving role of the CISO. With over 30 years in security, Kimberly shares insights from her career, emphasizing the importance of bridging the gap between business and technology. Drawing inspiration from Apollo 13 , likening a CISO’s role to mission control, she highlights navigating unexpected challenges with agility and confidence and shifting from a compliance-driven security program to a more integrated, business-resilient approach.