Systemic Cyber Risk: A CISO’s Impossible Task

Episode 91 · June 4, 2025 · 43:14

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 unpac...

Phishing for Truth: Fixing the Flaws in Security Awareness

Episode 90 · May 28, 2025 · 31:53

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 metr...

The Accidental CISO

Episode 89 · May 21, 2025 · 35:38

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 h...

A Story of Limited Resources

Episode 88 · May 7, 2025 · 32:42

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...

From Homicide to Hackers: Fixing Cybersecurity’s Broken Model

Episode 87 · April 23, 2025 · 34:58

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 unexpecte...

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

Episode 86 · April 16, 2025 · 36:14

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 e...

I Robbed a Bank with a Solar Eclipse

Episode 85 · April 9, 2025 · 41:53

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 kin...

A Confluence of Errors and a Little Help From Friends

Episode 84 · April 2, 2025 · 32:00

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 innovatio...

Cyber Truths, Intelligence Myths, and Life after the NSA

Episode 83 · March 26, 2025 · 33:42

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, ...

Every Day is a Risk Decision

Episode 82 · March 19, 2025 · 29:39

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...

Silent Risk - How Do We Figure Out What We Don't Know?

Episode 81 · March 12, 2025 · 13:16

In this episode of Risk and Reels, Jeffrey Wheatman (interviewing himself!) dives into the concept of the 'silent breach'—cybersecurity exposures that organizations don’t realize exi...

Telling YOUR Story Within Your Organization

Episode 80 · February 26, 2025 · 27:14

In this episode (throwback to Black Hat 2024), Jeffrey talks to Munish Walther-Puri, Adjunct Fellow at NYU Center for Global Affairs. Jeffrey and Munish discuss exploring real-life c...

The Concerning Impact of Cybersecurity on National Security

Episode 79 · February 19, 2025 · 36:12

In this episode, Jeffrey talks to Dr. David Bray, PhD, who shares his extensive background in cybersecurity, national security and technology in the public sector. The conversation e...

Meet an Attorney Who Keeps CISOs Out of Legal Hot Water

Episode 78 · February 12, 2025 · 31:43

In this episode, Jeffrey talks to Steven Teppler, a partner at Mandelbaum Barrett and the lead of the firm's Privacy and Cybersecurity practice group. Steve is an ISACA-certified Cer...

Addressing Cybersecurity’s Education and Engagement Challenges

Episode 77 · February 5, 2025 · 26:21

In this episode, Jeffrey talks to Lisa Plaggemier, Executive Director of the National Cybersecurity Alliance. They discuss their favorite movie-based educators, the importance of cyb...

Fresh Perspectives from a Future Cybersecurity Leader

Episode 76 · January 29, 2025 · 25:10

Cybersecurity veterans see the industry through the lens of experience. But how do those visions align with the outlooks of up-and-coming cybersecurity pros? In this episode, Jeffrey...

What the Trump Administration Could Mean for Cybersecurity

Episode 75 · January 22, 2025 · 37:14

In this episode, Jeffrey talks to Merritt Baer, CISO and advisory board member for Reco. Merritt also advises private businesses like Expanso, Andesite, Enkrypt AI and Level 6 Cybers...

Everything is an Endpoint — and Other Zero Trust Insight

Episode 74 · January 15, 2025 · 26:17

In this episode, Jeffrey talks to Jessica Dapelo, a zero trust expert and founder of Jessica Dapelo Enterprises, a consulting firm specializing in cybersecurity guidance for public s...

We Really Need to Shake S*** Up in Cybersecurity Research and Insight

Episode 73 · January 8, 2025 · 31:39

In this episode, Jeffrey speaks with cybersecurity marketing extraordinaire Dani Woolf, co-founder of CyberSynapse and CEO/host of the Audience 1st podcast. They discuss movies where...

Yes, CISOs Should Be Ethical — But Maybe We Stop Lying To Them

Episode 71 · December 18, 2024 · 46:24

In this episode, Jeffrey talks to Robert “RSnake” Hansen, Managing Director at Grossman Ventures. He’s also a computer hacker, executive and entrepreneur. He’s most well-known for hi...

Turtles All the Way Down — Looking for Third-Party Risk in DORA

Episode 70 · December 11, 2024 · 32:46

In this episode, Jeffrey Wheatman talks to Sandra Saliba, TPP Governance Manager at APS Bank. Jeffrey and Sandra dig into the Digital Operational Resilience Act (DORA), the implicati...

Enough With the Cybersecurity Gatekeeping — Be a Genuine Mentor

Episode 69 · December 4, 2024 · 32:17

In this episode, Jeffrey talks with Dave Ruiz — aka “CyberDAve” — cybersecurity leader for the Public Works Commission in Fayetteville, North Carolina. Dave is an Army veteran with o...

Hey, Cybersecurity Pros: Complexity is the Enemy of Execution

Episode 68 · November 27, 2024 · 31:57

In this episode, Jeffrey talks to Edgar Jones, co-founder of Luminated in Thought — aka L.I.T. — an organization specializing in individual and group coaching for professionals. Edga...

Navigating Bias — Cybersecurity’s Crooked Mirror

Episode 67 · November 20, 2024 · 33:08

In this episode, Jeffrey talks to Dr. Dustin Sachs, Chief Technologist and Sr. Director of Programs at the CyberRisk Collaborative. They discuss movies in which a main character’s mi...

Helping CISOs Communicate Their Way To Positive Outcomes

Episode 66 · November 13, 2024 · 30:10

In this episode, Jeffrey talks to Rock Lambros, founder and CEO of RockCyber. Along with coaching CISOs and serving as a vCISO, Rock is also a published thought leader, co-authoring ...

The Art of Throwing the (Calculated) Cybersecurity Hail Mary

Episode 65 · November 6, 2024 · 33:14

In this episode, Jeffrey talks to Mel Reyes, CEO of Elite Technical Concierge. Mel’s background is deep, with expertise in helping organizations build successful security programs wi...

What the Military’s “Elegant and Brutal” Model Can Teach Us About Cybersecurity

Episode 64 · October 30, 2024 · 30:58

In this episode, Jeffrey talks to Cindy Seipert, an InfoSec GRC analyst at Health Catalyst. They discuss movies that challenge our identity, Cindy’s unique career path from the milit...

You’ve Got To Be Audacious To Succeed

Episode 63 · October 23, 2024 · 30:25

In this episode, Jeffrey talks with Keren de Via, Go-to-Market Director at Cyturus Technologies. Keren has a deep cybersecurity background and was the first female Combat Communicati...

What Better Time Than Now? (And Other Considerations for Aspiring Security Professionals)

Episode 62 · October 16, 2024 · 28:28

In this episode, Jeffrey talks to Tanara Burke-Lloyd, SOC Analyst at Littler, the largest global employment and labor law practice. They discuss “fish out of water” movies, her inspi...

Why “Always Be Collaborating” Should Overshadow “Always Be Closing” in Security Sales

Episode 61 · October 9, 2024 · 27:17

In this episode, Jeffrey talks to entrepreneur and four-time CISO Demetrios Lazarikos — aka Laz. Laz is the founder and IT security consultant of Blue Lava Consulting. They discuss w...