Security Boulevard Podcast

What does a cybersecurity score of 76 really mean?

In this episode of Security Boulevard, Tom Hollingsworth, Fernando Montenegro, and Jay Cuthrell tackle one of the most persistent challenges in cybersecurity: reducing complex risk to a single number on a dashboard.

They unpack why so many security scores lack context, give a false sense of precision, and often mislead the very executives they’re meant to inform. The discussion div...

NVIDIA is no longer just selling chips—it is becoming a central force in the future of AI infrastructure and security.

On this episode of the Security Boulevard podcast, Tom Hollingsworth, Alan Shimel, and Mitch Ashley break down NVIDIA’s growing security ecosystem and what it means for the enterprise.

The conversation explores NVIDIA’s partnerships with major players including CrowdStrike, HPE, and Cisco, and why the company’s rol...

When a cyberattack moves from "pay us" to "destroy everything," the rules of digital warfare have officially changed.

In this episode of Security Boulevard, Tom Hollingsworth, Fernando Montenegro, and Jack Poller break down the devastating "wipe" attack on healthcare giant Stryker.

Unlike typical ransomware focused on financial gain, this attack saw laptops, phones, and entire systems systematically erased, signaling a chilling shi...

Is the era of "wild west" AI development finally coming to an end, or are we just building taller fences?

In this episode of the Security Boulevard Podcast, Tom Hollingsworth, Mitch Ashley, and Fernando Montenegro dive into why AI regulation has shifted from a "nice-to-have" ethical debate to an urgent cybersecurity mandate.

As the industry prepares to descend on San Francisco, the trio breaks down the high-stakes collision between...

If we can't see what AI is actually doing, how can we ever hope to secure it?

In this episode of the Security Boulevard Podcast, hosts Tom Hollingsworth, Mitch Ashley, and Fernando Montenegro break down the complex intersection of Artificial Intelligence and modern cybersecurity.

As AI continues to reshape software development, the team explores why observability has become the critical foundation for establishing accountability an...

AI agents are accelerating discovery, automation, and operational change—but enterprise security teams are still operating on human-speed processes.

In this episode of Security Boulevard, Mitch Ashley joins Tom Hollingsworth and Fernando Montenegro to examine what happens when AI-driven systems begin operating at machine speed while traditional security workflows remain constrained by governance, patch cycles, and change management...

AI is no longer just assisting security teams — it’s actively finding vulnerabilities humans missed.

In this episode of Security Boulevard, Tom Hollingsworth, Alan Shimel, and Fernando Montenegro examine the real-world implications of AI-driven vulnerability discovery after Anthropic allowed Claude to conduct large-scale scanning across open-source projects.

The result? More than 600 vulnerabilities identified — including a long-st...

Cybersecurity failures increasingly originate inside the software supply chain.

In this episode, Tom Hollingsworth, Event Lead at Tech Field Day and Networking Industry Analyst, joins Mitch Ashley, Vice President and Practice Lead, Software Lifecycle Engineering at Techstrong Research, along with Steve Puluka, Network & Security Engineer and Network Architect, Tech Field Day Delegate.

They examine supply chain compromises, in...

In this episode of the Security Boulevard Podcast, Tom Hollingsworth, Mitch Ashley, and Zoe Rose, CSIRT SecOps Dev Manager at Canon EMEA, examine the growing challenges around data ownership, digital sovereignty, and privacy in modern cybersecurity.   The discussion breaks down the complexity of data privacy laws, particularly the differences between the United States and Europe, and what those regulatory gaps mean for organizatio...

Cybersecurity plays a critical role in disaster recovery planning, especially as threats and environments continue to change.

In this episode of the Security Boulevard Podcast, Mitch Ashley, Fernando Montenegro, and Tom Hollingsworth discuss why realistic threat models and regular testing are essential to uncovering hidden weaknesses. The conversation draws lessons from past weather-related disasters and cybersecurity near misses,...

The appointment of Jen Easterly as CEO of the RSA Conference marks a pivotal moment for the cybersecurity industry.

In this episode of the Security Boulevard Podcast, Tom Hollingsworth, Alan Shimel, and Fernando Montenegro discuss what this leadership change signals for the broader security community.

The conversation examines the evolving role of CISA, the growing influence of venture capital on cybersecurity startups, and why p...

In this episode of the Security Boulevard Podcast, Mitch Ashley, Fernando Montenegro, and Tom Hollingsworth cover several of the most active conversations in cybersecurity and software development today.

The panel examines Palo Alto Networks’ SHIELD framework, the rise of vibe coding, and the security risks that emerge when non-programmers begin building software without embedded security practices.

The discussion also looks at h...

Email the podcast: securityblvdpodcast@futurumgroup.com    In this episode of the Security Boulevard Podcast, Tom Hollingsworth, Fernando Montenegro, and Mitch Ashley break down modern offensive security strategies and why organizations must prepare for real adversaries, not theoretical ones.   The discussion focuses on red teaming, rules of engagement, and how understanding adversarial intent changes defensive posture. The panel ...

Cybersecurity roles are changing as AI becomes part of everyday business operations. In this episode of the Security Boulevard Podcast, Tom Hollingsworth, Fernando Montenegro, and Alan Shimel discuss how security teams must adapt to new technologies while staying aligned with business priorities.

The conversation covers the challenges of scaling security alongside AI agents, the growing need to train and mentor junior professional...

In this episode of the Security Boulevard Podcast, Tom Hollingsworth, Alan Shimel, and Mitch Ashley examine how agentic AI is changing the cybersecurity landscape.

The discussion focuses on the growing security risks introduced by autonomous AI agents, why stronger protections are required, and how observability is becoming critical for managing AI workloads at scale. The panel also looks at the responsibility shared by vendors, d...

Cloud security keeps shifting under everyone’s feet, and organizations are scrambling to keep up. In Ep. 11 of the Security Boulevard Podcast, Tom Hollingsworth, Fernando Montenegro, and Mitch Ashley dig into what modern teams actually face: expanding attack surfaces, tangled interdependencies, regulatory pressure, and the constant need for better collaboration.

The discussion highlights why vendors must do more to educate customer...

In Episode 10 of the Security Boulevard Podcast, Tom Hollingsworth, Fernando Montenegro, and Mitch Ashley break down the real impact of major service outages — including recent failures at Cloudflare — and what they reveal about modern cybersecurity challenges.

The discussion covers why resilience matters, how economic pressures shape security decisions, and the growing complexity of today’s interconnected infrastructure. The panel...

AI is reshaping cybersecurity faster than most organizations can adapt. In Ep. 9 of the Security Boulevard Podcast, Emanuela Zaccone and Eric Carter of Sysdig join Tech Field Day's Tom Hollingsworth and The Futurum Group's Fernando Montenegro to examine how AI is transforming cyber risk, decision-making, and business resilience.

They discuss the rapid evolution of attackers, the need to secure AI-driven processes, and why trust is ...

AI is reshaping cybersecurity on both sides of the fight. In Ep. 8 of the Security Boulevard Podcast, Tom Hollingsworth, Jack Poller, and Ed Weadon examine how AI strengthens defense while also creating new attack vectors.

They break down recent failures, long-term gaps in AI security, and the growing responsibility on AI developers to build safer systems. As attackers weaponize AI, defenders must adopt stronger controls, better co...