Risk and Reels: A Cybersecurity Podcast

Latest Episodes:

Silent Risk - How Do We Figure Out What We Don't Know? Mar 12, 2025

Show notes

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 exist until it’s too late. He explores real-world examples of major supply chain vulnerabilities and the challenges of visibility in today’s digital ecosystem. Wheatman also discusses how organizations can improve risk assessment and response strategies to mitigate the cascading effects of hidden threats.

Telling YOUR Story Within Your Organization Feb 26, 2025

Show notes

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 challenges through fantasy and science fiction movies, allowing us to think through the more "uncomfortable" topics in a comfortable space. Have you heard of a "pirate unicorn?" Doubtful. Listen to episode 80 to find out.

The Concerning Impact of Cybersecurity on National Security Feb 19, 2025

Show notes

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 explores the accurate portrayal of cybersecurity in movies, the challenges of supply chain security, and the importance of deep hardware interrogation to ensure the integrity of technology.

Dr. Bray emphasizes the need for proactive measures in cybersecurity and the significance of understanding the perception of reality in the context of social engineering and national security. They also dig into the evolving landscape of cybersecurity, focusing on the challenges posed by compromised hardware, the rise of scams and ransomware and the dynamics between government and non-state actors. The conversation also touches on the implications of generative AI in cybersecurity and emphasize the need for proactive measures and innovative solutions to address these threats.

Meet an Attorney Who Keeps CISOs Out of Legal Hot Water Feb 12, 2025

Show notes

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 Certified Data Privacy Solutions Engineer (CDPSE) and the firm's chief cybersecurity legal officer. They discuss sci-fi movies and the intersection of cybersecurity and law — focusing on the evolving role of Chief Information Security Officers (CISOs) and the legal implications they face. They also explore the increasing legal exposure for CISOs, the complexities of downstream liability and the importance of defensibility in cybersecurity practices.

Addressing Cybersecurity’s Education and Engagement Challenges Feb 05, 2025

Show notes

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 cybersecurity awareness, the challenges in measuring its effectiveness and the need for engaging educational content.

Fresh Perspectives from a Future Cybersecurity Leader Jan 29, 2025

Show notes

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 talks to Nick Crabb, a senior at Florida Gulf Coast University majoring in computer information systems, focusing on cybersecurity. They discuss their favorite college movies, Nick's educational journey, the challenges of entering the field and AI's impact on future job prospects.

What the Trump Administration Could Mean for Cybersecurity Jan 22, 2025

Show notes

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 Cybersecurity. She has a background in cybersecurity within the U.S. government and spent five years at AWS. Jeffrey and Merritt discuss their favorite fictitious world leaders, how the Trump administration may impact cybersecurity and the importance of public/private partnerships.

Everything is an Endpoint — and Other Zero Trust Insight Jan 15, 2025

Show notes

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 sector organizations and agencies. They discuss movies about the convergence of two worlds, the importance of understanding zero trust as a proactive cybersecurity methodology, the implications of ethical AI on data privacy and the need for organizations to be aware of their data storage and access permissions.

We Really Need to Shake S*** Up in Cybersecurity Research and Insight Jan 08, 2025

Show notes

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 the main character rocks the status quo, the unique challenges of marketing in the cybersecurity space, the shortcomings of traditional analyst models and the importance of direct customer engagement. The conversation also touches on the necessity of collaboration within the cybersecurity community and the common pitfalls smaller vendors face when trying to penetrate the enterprise market.

Yes, CISOs Should Be Ethical — But Maybe We Stop Lying To Them Dec 18, 2024

Show notes

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 his security research and disclosures such as Slowloris, Clickjacking, Fierce DNS enumeration tool and others.

RSnake produces a wide range of security content including The RSnake Report newsletter, a podcast called The RSnake Show and a book entitled AI’s Best Friend. Jeffrey and Robert discuss movies where a main character struggles with an ethical dilemma, the temptations for CISOs to act unethically and how companies should support CISOs to minimize the prevalence of those temptations.