Home Podcasts Cybersecurity News & Analysis by Cyber Sidekicks - Your Weekly Update’
Cybersecurity News & Analysis by Cyber Sidekicks - Your Weekly Update’

Cybersecurity News & Analysis by Cyber Sidekicks - Your Weekly Update’

Christina Richmond | Rory Duncan - Cybersecurity Experts | Richmond Advisory Group 89 Episodes Oct 13, 2026

Cybersecurity News & Analysis by Cyber Sidekicks is a weekly podcast covering the cybersecurity market, industry trends, and the practical challenges of protecting organizations. Hosted by cybersecurity experts Christina Richmond and Rory Duncan, it provides updates and analysis for security professionals. The show helps listeners understand evolving threats and defensive strategies. It is produced by Richmond Advisory Group.

Episodes

Cloudsmith on Software Supply Chains and "Don't Make Me Think" Security
Cloudsmith on Software Supply Chains and "Don't Make Me Think" Security Oct 13, 2026 2190 Hosts Christina Richmond and Rory Duncan are joined this week by Glenn Weinstein, CEO of Cloudsmith to discuss building high-performing company cultures, navigating software supply chain risks, and securing modern development workflows. To counter machine-speed AI threats, Glenn proposes that organizations must embed automated "don't make me think" security guardrails directly into workflows so de
Intruder on Continuous AI Pen Testing and the White-Box Advantage
Intruder on Continuous AI Pen Testing and the White-Box Advantage Oct 6, 2026 2413 This week, Andy Hornegold, Chief Security Technologist and Head of Product at Intruder joins hosts Christina Richmond and Rory Duncan to discuss offensive security, the economics of defensive AI, and how organizations can stay ahead of modern threat actors. The trio conclude that, to navigate rapid threat evolution and the rising costs and guardrails of commercial frontier models, defenders must p
The AI Resilience Loop: ISMS Online on Bridging the Governance Gap
The AI Resilience Loop: ISMS Online on Bridging the Governance Gap Sep 29, 2026 2174 Chris Newton-Smith, CEO of ISMS Online returns as a guest on this week's episode, discussing with Christina and Rory about how organizations can bridge the gap between perceived readiness and actual operational resilience given the challenges of both fair and foul uses of AI and AI Agents. Chris argues that to bridge the gap between perceived AI readiness and actual operational capability, organiz
The Telepathic Adversary: TrendAI outlines AI's C2 Threat
The Telepathic Adversary: TrendAI outlines AI's C2 Threat Sep 22, 2026 2428 In this week's episode, Christina & Rory talk with Tom Kellermann, VP of AI Security & Threat Intelligence at TrendAI about how rogue nation-states and AI-driven offensive tactics are disrupting traditional cybersecurity defenses. Tom outlines how four rogue nation-states—Russia, China, North Korea, and Iran—are collaborating and sharing command-and-control (C2) capabilities and exploits a
Why Containment Matters: Illumio On Attack Physics & Cyber Resilience
Why Containment Matters: Illumio On Attack Physics & Cyber Resilience Sep 15, 2026 2168 This week, host Rory Duncan speaks with guest Raghu Nandakumara, VP of Industry Strategy at Illumio, discussing why traditional security controls are failing against modern threats and why enterprises must prioritize containment and business-led resilience. Raghu emphasizes that while foundational security hygiene is frequently neglected for attractive new technologies, containment must serve as t
The Open-Weight Liability Trap: Who Pays When AI Fails?
The Open-Weight Liability Trap: Who Pays When AI Fails? Sep 8, 2026 2823 This week, Christina & Rory are joined by Fractional CISO, Risk & Governance expert,  - and soon to be author - Kayne McGladrey as he returns to the show to discuss the complex and rapidly evolving legal and financial realities of AI liability. Who takes the fall when AI systems make critical errors, violate copyrights, or leak data? The discussion delves into the pros and cons of open-wei
The Missing "R": Semperis On Identity, Resilience & Recovery
The Missing "R": Semperis On Identity, Resilience & Recovery Sep 1, 2026 2202 In this week's episode, Simon Hodgkinson - strategic advisor for Semperis - returns for his third appearance on the show to discuss why the cybersecurity industry needs to completely re-evaluate how it handles identity resilience. Is ITDR missing it's "R", because it fails to include "Recovery"? Christina, Rory & Simon discuss how a true response to an identity platform compromise cannot be se
Beyond the AI Hype: Billion-Dollar Infrastructure and the Reality of Cyber M&A
Beyond the AI Hype: Billion-Dollar Infrastructure and the Reality of Cyber M&A Aug 25, 2026 1775 Another Special Episode this week! Christina and Rory review the state of the cybersecurity M&A landscape in 2026, and discuss how AI is causing a significant shift in strategic positioning, driven by a mixture of time-to-market desire, infrastructure build-outs, and a continuing approach by major telecommunications companies to spin-out their security services divisions. Fortinet Acquires AI
The High-Fidelity Future of AI Impersonation, with ZeroFox
The High-Fidelity Future of AI Impersonation, with ZeroFox Aug 18, 2026 2131 In this week's episode, Christina are Rory are joined by Russ Bentley, EVP Product Management at ZeroFox to discuss the alarming ease with which AI can now be used to create ultra-realistic and convincing impersonations and the resulting challenges for executive protection. Some great points by Russ, including the need for a return to foundational social engineering awareness. Recommendations: foc
Why AI is not the (only) answer in Cybersecurity
Why AI is not the (only) answer in Cybersecurity Aug 11, 2026 2617 SPECIAL EPISODE: this week, Christina & Rory take the plunge and debate the merits of AI and AI Agents in cybersecurity strategy. What are the pros & cons? How can AI benefit those managing cyber defence vs. the cyber criminals, nation state actors and other attackers pushing on the offensive side? It's often been called an "arms race", so where will it end - if it can? What are the lesson
The Server in the Corner: Securing the Forgotten AI Attack Surface
The Server in the Corner: Securing the Forgotten AI Attack Surface Aug 4, 2026 1931 In this week's episode, Jim LaRoe, CEO of Symphion, discusses the critical security risks associated with printers and IoT devices, which he argues are the most overlooked endpoints in the modern AI-enabled threat landscape. LaRoe emphasizes that while printers are often treated as "dumb appliances," they have evolved into sophisticated servers that reside inside the organizational network. Printe
The Pentest Renaissance: Synack on Offensive Security & AI Agents
The Pentest Renaissance: Synack on Offensive Security & AI Agents Jul 28, 2026 2718 Paul Mote, VP Solutions Architect at Synack, chats with Christina & Rory about how artificial intelligence is forcing a radical shift in offensive security and vulnerability management, including why the increasing number of autonomous attacks requires much more robust autonomous defenses. The solution? Organizations must move toward continuous automated patching or blocking to avoid falling h

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