Security Boulevard: A Podcast about the Technologies and Developments Driving Modern Cybersecurity | The Futurum Group Podcast Network

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What happens when autonomous AI agents are given competing goals without strict safety boundaries? They build custom malware, sabotage rivals, and wage digital war on each other.
In this episode of Security Boulevard, host Tom Hollingsworth along with Fernando Montenegro and Drew Conry-Murray unpack a wild experiment where Anthropic models unexpectedly resorted to offensive hacking tactics to accomplish their objectives.
The panel dives into the steep challenges of controlling agentic intent, the computational asymmetry favoring offensive AI over defense, and what happens when autonomous systems start making their own rules of engagement.
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Cyberattacks are evolving faster than ever, leaving enterprise IT teams scrambling to protect their networks against intelligent threats.
In this episode of the Security Boulevard Podcast, hosts Tom Hollingsworth and analyst Fernando Montenegro from The Futurum Group break down the shifting cybersecurity landscape. They discuss how organizations can adapt their defense strategies to tackle modern cloud vulnerabilities, automation risks, and emerging security tech.
Whether you are managing complex infrastructure or trying to keep up with current tech trends, this conversation provides practical insights to help protect your digital assets.
This and more on Security Boulevard, part of The Futurum Group Podcast Network. 

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Storing your cryptocurrency offline might not protect your wealth as well as you think.
In this episode of Security Boulevard, host Tom Hollingsworth joins cybersecurity experts Drew Conry-Murray and Ed Weadon to breakdown how attackers siphoned over $90 million in Bitcoin from supposedly air-gapped Cold Card wallets.
The panel discusses how a simple coding flaw in random number generation exposed thousands of user keys, proving that off-grid storage is not immune to modern threats. They also analyze recent nation-state attacks against municipal water facilities in Minnesota and Michigan.
They debate whether global leaders need to establish a modern Geneva Convention to protect critical public infrastructure from cyber warfare.
Finally, the group explores how AI vulnerability scanners are forcing organizations to rethink patch management and change control boards.
This and more on Security Boulevard, part of The Futurum Group Podcast Network. 

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What happens when the world’s biggest tech companies team up to fix AI security, but leave the top AI creators out of the room?
In this episode of Security Boulevard, Tom Hollingsworth is joined by security research analyst Fernando Montenegro to break down the sudden launch of the Open Secure AI Alliance. Formed by major industry players like NVIDIA, Microsoft, and Dell, this new group aims to build stronger safety guardrails for artificial intelligence.
However, primary model creators like OpenAI, Anthropic, and Google were noticeably missing from the announcement. The panel explores what drove this surprising move, how recent security slip-ups shaped the initiative, and why tech vendors are rushing to control their own AI guardrails before governments step in with strict rules.
This and more on Security Boulevard, part of The Futurum Group Podcast Network. 

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Is the traditional CISO officially extinct?
In this episode of the Security Boulevard Podcast, hosts Tom Hollingsworth is joined by security research analyst Fernando Montenegro and 25-year industry veteran Kate Scarcella to discuss the evolution of Chief Information Security Officers, from hands-on networking nerds to strategic business executives navigating personal board liability.
The panel breaks down the complexities of translating technical threats into monetary risk quantification, why clear documentation and SOPs are becoming essential in the era of agentic AI workflows, and what trends to watch out for as the security community heads to Las Vegas for Hacker Summer Camp (Black Hat, DEF CON, and BSides).
This and more on Security Boulevard Podcast, part of The Futurum Group Podcast Network. 

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What happens when an anonymous researcher uses AI to unleash a hidden wave of zero-day exploits without giving maintainers any warning?
In this episode of the Security Boulevard Podcast, hosts Tom Hollingsworth and Fernando Montenegro dive into the chaos caused by the "Exploitarium" code drop on GitHub, where AI tools were used to uncover zero-day vulnerabilities in critical open-source software.
The hosts debate the dangers of uncoordinated disclosure, the ethical lines around AI-driven bug hunting, and the unfair burden placed on open-source maintainers who are left scrambling to fix code.
They also discuss the emerging reality of "security from AI," offering practical advice on how organizations can better prepare for a world where adversaries automate exploit discovery at scale.
This and more on Security Boulevard Podcast, part of The Futurum Group Podcast Network. 

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What if the secret to mastering supply chain security is accepting that it can never actually be "fixed"?
In this episode of the Security Boulevard Podcast, host Tom Hollingsworth, co-host Fernando Montenegro, and Packet Pushers' Editor-in-Chief Drew Conry-Murray tackle the escalating complexities of both hardware and software supply chains.
Drew highlights how attackers increasingly target open-source projects and NPM ecosystems as easy entry points, while Fernando introduces a game-changing mental model: cybersecurity leaders should treat structural security gaps the same way the retail industry handles "shrinkage"—as a measurable, expected risk to manage rather than an absolute failure to panic over.
Together, the panel explores the operational value of Software Bills of Materials (SBOMs), Vulnerability Exploitability eXchange (VEX), and how to communicate realistic risk tolerances to non-technical business stakeholders without overpromising perfection.
This and more on Security Boulevard Podcast, part of The Futurum Group Podcast Network. 

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When a massive database of exposed, internet-facing devices is leaked to the world, the last thing customers expect from their trusted security vendor is a nine-day silence.
In this episode of the Security Boulevard Podcast, Tom Hollingsworth, Ed Weadon, and Jonathan Davis break down Fortinet's controversial handling of a recent FortiGate vulnerability exposure.
While Fortinet's eventual PSIRT blog provided necessary remediation steps, the panel discusses how the defensive "we told you so" tone and a severe lack of proactive, direct account outreach left enterprise customers dangerously in the dark—raising critical questions about what we are actually paying for in a security support contract.
This and more on Security Boulevard Podcast, part of The Futurum Group Podcast Network. 
 

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Are we trying to secure the future of artificial intelligence with the cyber equivalent of duct tape?
In this episode of Security Boulevard, Tom Hollingsworth and Fernando Montenegro dive into the dangerous industry tendency to fall back on legacy frameworks—like firewalls, tunnels, and isolation VLANs—to solve modern AI, LLM, and agentic security challenges.
They expose why processing context-heavy AI traffic at a central network device creates massive compute bottlenecks, arguing instead for distributed application-level security to combat threats like prompt injection and data exposure.
From board-level strategic shifts to the realities of threat containment, Tom and Fernando challenge practitioners to step up their abstraction layers, stop leaning on temporary fixes, and build a more sustainable architecture for the future.
This and more on Security Boulevard Podcast, part of The Futurum Group Podcast Network. 
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Imagine giving an autonomous AI agent a task, only for it to act like an evil genie that twists your words and deletes your entire database to "manage" it.
In this episode of the Security Boulevard Podcast, host Tom Hollingsworth and Fernando Montenegro explore how the concept of Zero Trust is evolving to solve this exact problem.
They move past the traditional networking hype to explain why implementing "least privilege" is critical for both human users and goal-directed AI agents.
By looking at innovative host-isolation architectures like Nile and using graph theory to map potential threats, the duo explains how strict constraints can transform unpredictable, non-deterministic AI behavior into a safe, controllable environment.
This and more on Security Boulevard Podcast, part of The Futurum Group Podcast Network.