In this episode of the Chasing Entropy Podcast, host Dave Lewis welcomes industry analyst and long-time cybersecurity veteran Fernando Montenegro for a far-ranging and refreshingly honest discussion about the evolution of security, the realities of AI, and the human stories that shape our digital defenses.

Fernando shares his origin story from math and fractals in Brazil to cryptography and bulletin boards, and ultimately to a career that has spanned consulting, sales engineering, and now research and analysis. Along the way, he highlights the importance of community spaces like TASK (Toronto Area Security Klatsch) and B-Sides as pivotal launchpads for industry newcomers.

The conversation dives deep into artificial intelligence and its nuanced role in cybersecurity:

• Security for AI: Helping organizations safely adopt AI tools.
• AI for Security: Using AI to enhance defense mechanisms.
• Security against AI: Preparing for AI-augmented attacks and fraud.

Fernando advocates for viewing AI through an economic and socio-technical lens rather than blindly trusting in its promise. As both he and Dave agree, AI isn't magic—it's math. It can augment work, but replacing human judgment, strategy, and contextual understanding is far from reality.

They also touch on the dangers of layoffs fueled by AI hype, calling out examples like Klarna’s public misstep, and drawing parallels to earlier cloud-related downsizing miscalculations. Both stress the importance of understanding what workers actually do before trying to replace them with automation.

As the episode wraps, Fernando delivers sage advice for those entering or pivoting into cybersecurity:

• Leverage your prior experience, whether from hospitality or marketing, it has value.
• Seek mentorship from peers 2–5 years ahead of you for tactical guidance.
• Don’t be discouraged by gatekeeping; curiosity and kindness go a long way in this relationship-driven field.

Whether you're a seasoned professional or just getting started, this episode is a candid reminder that cybersecurity is as much about people as it is about technology and that chasing entropy means embracing complexity, not avoiding it.