Security Boulevard Podcast

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...

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...

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...

In Episode 7 of the Security Boulevard Podcast, Tom Hollingsworth of Tech Field Day, Fernando Montenegro of The Futurum Group, and networking and security expert Ed Weadon break down what it really takes to advance a cybersecurity career today.

They discuss the demands of CISSP certification, the frustration of tracking continuing-education credits, and why lifelong learning is now essential for security pros, including the skills ...

In Ep. 6 of the Security Boulevard Podcast, Tom Hollingsworth, Mitch Ashley, and Alan Shimel discuss how ransomware tactics are shifting. Attackers are using AI-driven phishing to breach organizations while ransom payments decline as defenses improve. Malicious packages continue to exploit software vulnerabilities, and government hacking tools add new layers of risk. The panel highlights why cybersecurity strategies must keep evolv...

Will Agentic AI replace security teams? In this episode of the Security Boulevard Podcast, hosts Mitch Ashley, Tom Hollingsworth, and Fernando Montenegro explore how AI is reshaping cybersecurity — from large language models (LLMs) to autonomous agentic AI systems. Discover how professionals are integrating AI into modern security operations, why caution still dominates the industry, and what’s next for securing AI itself. Featurin...

In Episode. 4 of the Security Boulevard Podcast, Mitch Ashley, Tom Hollingsworth, and Fernando Montenegro dig into the rising threat of nation state cyber attacks and the growing sophistication of global cyber warfare.

They discuss:

• The evolution from small-scale hacks to state-backed intelligence operations
• Major breaches like F5 and what they reveal about attacker motives • How nation states fund and protect cyber groups
• The...