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 developers don't expend cognitive energy on manual vulnerability checks. Much like sports team management taking care of logistics so athletes can focus on competing, leadership should automate background security tasks to free developers to concentrate on solving core customer problems.

NEWS

US Senate Passes Bipartisan Bill to Strengthen Healthcare Cybersecurity

Temporal buys AI security startup Oso weeks after raising $550M

RSA Launches RSA Agent ID, an agentic identity security platform for highly regulated industries

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• Christina Richmond – christina@richmondadvisorygroup.com
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• Podcast Recording Platform – Cleanfeed.com
• Cyber Sidekicks Show Host – Podbean.com
• Edited & mastered in GarageBand

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 prioritize fundamental attack surface reduction and lean toward specialized or open-source models for cleaner vulnerability triage.

NEWS

Akamai publishes its latest State of The Internet (SOTI) report, titled “Speed, Scale and Non-Human Identity: The Agentic Threat Landscape”

CISCO Talos Discovers Closed Quorum: the first reported autonomous AI C2 implant

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Want to leave some feedback and suggestions but would prefer not to write an email? You can leave us a voicemail (90 seconds max). We will share any that are not too spicy in the following episode.

SpeakPipe link - https://www.speakpipe.com/Cyber_Sidekicks

Or, send us an email:

• Christina Richmond – christina@richmondadvisorygroup.com
• Rory Duncan – rory@richmondadvisorygroup.com

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Technology we use

• Podcast Recording Platform – Cleanfeed.com
• Cyber Sidekicks Show Host – Podbean.com
• Edited & mastered in GarageBand

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, organizations should adopt an integrated "resilience loop" that expands existing information security and data privacy frameworks. The hosts and Chris conclude that because complex digital systems make unexpected failures statistically inevitable, security leaders must use disciplined risk registers to prioritize resources and actively test incident response before a breach occurs.

NEWS

IBM Acquires Logiq Consulting

Fime acquires French cybersecurity specialist Red Alert Labs

Japan Dismantles First North Korean Laptop Farm as US and Allies Detail Wider Scheme

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Want to leave some feedback and suggestions but would prefer not to write an email? You can leave us a voicemail (90 seconds max). We will share any that are not too spicy in the following episode.

SpeakPipe link - https://www.speakpipe.com/Cyber_Sidekicks

Or, send us an email:

• Christina Richmond – christina@richmondadvisorygroup.com
• Rory Duncan – rory@richmondadvisorygroup.com

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Technology we use

• Podcast Recording Platform – Cleanfeed.com
• Cyber Sidekicks Show Host – Podbean.com
• Edited & mastered in GarageBand

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 at unprecedented levels. He explains how Russian guidance is elevating second-tier actors, driving destructive attacks against critical infrastructure like energy and water utilities, while these states actively shield cybercrime cartels as national assets.

NEWS

Anthropic promises zero data retention – but customers must check it worked

Nvidia’s Huang says cybersecurity will be next major AI use case

EU Cyber Resilience Act (CRA): Reporting obligations now in effect

NEXT WEEK'S GUEST

Next week's guest is Chris Newton-Smith, CEO of ISMS Online.

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Want to leave some feedback and suggestions but would prefer not to write an email? You can leave us a voicemail (90 seconds max). We will share any that are not too spicy in the following episode.

SpeakPipe link - https://www.speakpipe.com/Cyber_Sidekicks

Or, send us an email:

• Christina Richmond – christina@richmondadvisorygroup.com
• Rory Duncan – rory@richmondadvisorygroup.com

Subscribe to our Newsletter - "Signal, not noise" Our monthly newsletter is free to subscribers! Sign-up now at Richmond Advisory Group.

Technology we use

• Podcast Recording Platform – Cleanfeed.com
• Cyber Sidekicks Show Host – Podbean.com
• Edited & mastered in GarageBand

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 the essential "third pillar" alongside prevention and detection to disrupt the fundamental physics of cyber attacks. His recommendation: to prevent systemic operational shutdowns, organizations must abandon blanket policies across all assets and instead prioritize protecting their most critical business processes to effectively reduce overall operational risk.

NEWS

Criminals publish data of 8.7m people after UK airports hack

153 million Driver License images exposed via IDScan.net leak

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Want to leave some feedback and suggestions but would prefer not to write an email? You can leave us a voicemail (90 seconds max). We will share any that are not too spicy in the following episode.

SpeakPipe link - https://www.speakpipe.com/Cyber_Sidekicks

Or, send us an email:

• Christina Richmond – christina@richmondadvisorygroup.com
• Rory Duncan – rory@richmondadvisorygroup.com

Subscribe to our Newsletter - "Signal, not noise" Our monthly newsletter is free to subscribers! Sign-up now at Richmond Advisory Group.

Technology we use

• Podcast Recording Platform – Cleanfeed.com
• Cyber Sidekicks Show Host – Podbean.com
• Edited & mastered in GarageBand

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-weight models i.e. they save money on token costs, but the deploying company must assume 100% of the liability for both inputs and outputs, unlike when using a frontier model (like Microsoft or OpenAI), the company at least has a contractual defense and some recourse...

Kayne's website, inc. details of his forthcoming book: kaynemcgladrey.com

NEWS

McKesson Confirms Data Breach as Attacker Deadline Looms

Palo Alto Networks FY26 Q4, Earnings Results & Highlights

NetSPI and Synack to Merge

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Want to leave some feedback and suggestions but would prefer not to write an email? You can leave us a voicemail (90 seconds max). We will share any that are not too spicy in the following episode.

SpeakPipe link - https://www.speakpipe.com/Cyber_Sidekicks

Or, send us an email:

• Christina Richmond – christina@richmondadvisorygroup.com
• Rory Duncan – rory@richmondadvisorygroup.com

Subscribe to our Newsletter - "Signal, not noise" Our monthly newsletter is free to subscribers! Sign-up now at Richmond Advisory Group.

Technology we use

• Podcast Recording Platform – Cleanfeed.com
• Cyber Sidekicks Show Host – Podbean.com
• Edited & mastered in GarageBand

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 separated from recovery, because the identity platform is the lifeblood of the modern digital ecosystem. ITDRR perhaps??

NEWS

Financial damage from cyber-attacks grows despite falling claims volumes

Iran-Linked Hackers Shut Down UK Power Plant for Four Days

Leave us a message!

Want to leave some feedback and suggestions but would prefer not to write an email? You can leave us a voicemail (90 seconds max). We will share any that are not too spicy in the following episode.

SpeakPipe link - https://www.speakpipe.com/Cyber_Sidekicks

Or, send us an email:

• Christina Richmond – christina@richmondadvisorygroup.com
• Rory Duncan – rory@richmondadvisorygroup.com

Subscribe to our Newsletter - "Signal, not noise" Our monthly newsletter is free to subscribers! Sign-up now at Richmond Advisory Group.

Technology we use

• Podcast Recording Platform – Cleanfeed.com
• Cyber Sidekicks Show Host – Podbean.com
• Edited & mastered in GarageBand

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 Security Company Virtue AI

Genesis PE Acquires SK Shieldus Security Unit

Bank of America Acquires UK-based MDSec

NEWS

Tech layoffs in 2026 – cybersecurity vendors & service providers

Layoffs.fyi

Leave us a message!

Want to leave some feedback and suggestions but would prefer not to write an email? You can leave us a voicemail (90 seconds max). We will share any that are not too spicy in the following episode.

SpeakPipe link - https://www.speakpipe.com/Cyber_Sidekicks

Or, send us an email:

• Christina Richmond – christina@richmondadvisorygroup.com
• Rory Duncan – rory@richmondadvisorygroup.com

Subscribe to our Newsletter - "Signal, not noise" Our monthly newsletter is free to subscribers! Sign-up now at Richmond Advisory Group.

Technology we use

• Podcast Recording Platform – Cleanfeed.com
• Cyber Sidekicks Show Host – Podbean.com
• Edited & mastered in GarageBand