In this episode of Chasing Entropy, I sit down with cybersecurity trailblazer Wendy Nather for an honest, insightful, and occasionally hilarious conversation that spans career origin stories, hammer metaphors, and how empathy is the secret weapon of modern security leadership.

From Swiss Banks to Strategy

Wendy Nather’s journey into cybersecurity is anything but conventional. From wrangling Unix systems at a Swiss bank to being unexpectedly appointed head of EMEA security, her career has been a series of “say yes and figure it out later” moments. Her creation of the security strategist role at Duo (where she helped bring Dave onboard) laid the groundwork for today’s Advisory CISO model—distinct from field CISOs and rooted in trust-building and strategic influence.

Understanding the Security Poverty Line

Wendy unpacks her now-famous concept of the “security poverty line,” a lens for understanding how underfunded, understaffed organizations struggle to meet industry best practices. It's a call to move beyond judgment and toward practical empathy—especially when small businesses with outdated gear and little budget become backdoor vulnerabilities in the broader digital ecosystem.

The Human Side of Cybersecurity

The conversation dives deep into the need for empathy, especially at the CISO level. Wendy argues that real leadership in security isn’t about technical perfection—it’s about understanding people, building influence, and leading with compassion. For those just entering the field, she reminds listeners that many roles in cybersecurity today didn’t even exist a decade ago, and that we’re all still “making this up as we go.”

Agentic AI, Zero Trust, and a Spoon

The pair also reflect on the rise of agentic AI and its implications for zero trust architectures. Wendy challenges the assumption that AI introduces completely new risks, suggesting instead that it’s a matter of awareness, contract transparency, and figuring things out as a community. She also revisits her “spoon” analogy from past keynotes: good security design should be as intuitive as using a spoon—hard to mess up, universally usable.

Final Thoughts

Wendy closes with advice for veterans and newcomers alike: surround yourself with peers you trust, keep learning, and don’t buy into gatekeeping myths that overvalue technical credentials. What really matters is adaptability, collaboration, and understanding the bigger picture.

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In this episode of Chasing Entropy, host Dave Lewis, Global Advisory CISO at 1Password, sits down with Adrian Sanabria—Principal Researcher at the Defenders Initiative and founder of Destroyed by Breach—for a wide-ranging and candid conversation about the challenges, myths, and future of cybersecurity.

From Help Desk to Hacking the Narrative

Adrian shares his unconventional journey into the cybersecurity world, tracing it back to retail tech support and internet help desk gigs where he developed resilience, empathy, and a knack for communication. He talks about how early experiences handling confused customers over phone lines laid the groundwork for a career in community engagement, public speaking, and eventually running B-Sides Knoxville.

Debunking Security Myths

Adrian doesn’t pull punches. From phishing simulations and forced password resets to the overhyped impact of breaches, he challenges many “best practices” that persist in cybersecurity. He notes that while the industry once operated on instinct and guesswork, we now have decades of actionable data—but still struggle to act on it meaningfully.

Agentic AI, Shadow IT, and the Next Frontier

The conversation turns to emerging threats and opportunities, particularly around Agentic AI and open-source vulnerabilities. Adrian warns that while companies rush to adopt automation and AI tools, they’re often ignoring foundational problems—like identity management and shadow IT—that have plagued organizations for decades.

Policy, Priorities, and the Security Industry’s Missed Opportunity

Both Dave and Adrian agree: governments are stepping in with cybersecurity policies because the security industry has failed to manage its own narrative. Marketing budgets, FUD, and vendor agendas have diluted the voice of practitioners. The episode urges listeners to advocate for more grounded, evidence-based conversations in the field.

What’s Next and What Matters Most

As AI hype barrels forward, Adrian sees it as both a distraction and an opportunity. “It’s useful tech,” he says, “but we’re not using it wisely.” Instead of slow, GPU-hungry processes, he calls for smarter automation and attention to patterns that really matter.

He also reflects on his own growth: learning to play to strengths, managing ADHD, and finding fulfilling work that delivers real feedback.

Final Advice for Aspiring Cybersecurity folks

Adrian closes with advice that’s equal parts practical and personal, encouraging newcomers to the field to be self-aware, adaptable, and unafraid to seek help—be it professional diagnosis or community mentorship.

Listen & Subscribe

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In this episode of Chasing Entropy, host Dave Lewis welcomes longtime friend and cybersecurity thought leader Matt Johansen. What unfolds is a deeply insightful, often personal discussion that spans the evolution of an entire career—from a student in a literal church pew to a key voice shaping cybersecurity narratives today.

From Dorm Room to Industry Leader

Matt shares the serendipitous moment that ignited his cybersecurity career: a last-semester class taught by a university CISO, a DVD of James Arlen’s “Black Hat to Black Suit,” and the early encouragement to engage on Twitter and LinkedIn. That first year of digital networking proved foundational—every boss Matt's had, he met during that stretch.

Big Banks and Shadow IT

Matt contrasts his experience building security programs at a scrappy fintech startup with the tightly controlled environment at Goldman Sachs post-acquisition. He discusses how rigid controls can reduce risk but stifle innovation, and unpacks how shadow IT thrives even in the most controlled environments. The lesson? Security postures must match organizational realities.

Mental Health, Burnout & the Myth of the Security Superhero

One of the episode's most powerful threads is Matt’s advocacy for mental health awareness in cybersecurity. He critiques "superhero culture," where the same individuals are always relied on in crises. Instead, he calls for real structural changes—proper rotations, mandatory time off, and leadership accountability. As he puts it, you can’t yoga your way out of burnout.

Identity is the New Malware

Matt and Dave explore how the attack surface has shifted. With SaaS proliferation and stolen credentials replacing malware as the primary attack vector, identity management has become paramount. Highlighting attacks like the TeleMessage breach and the phishing incident involving Troy Hunt, they emphasize that security must make “clicking links” safe—not shame users for doing it.

Vulnerable U & Making Security Accessible

Matt now runs Vulnerable U—a cybersecurity media company delivering digestible infosec news via newsletters, YouTube, TikTok, and Instagram. He reflects on how his early work curating news for Liquid Matrix evolved into a full-time passion for communicating security in a human, relatable way.

Advice for Aspiring Professionals

Matt’s number one tip for newcomers? Create content. Even if you’re still learning, share your process. Blog your breakthroughs, record your thought process, and contribute to the dialogue. That transparency and authenticity open doors.

Mentioned in the Episode:

• Vulnerable U: vulnu.com
• TeleMessage Security Breach
• The "Black Hat to Black Suit" talk by James Arlen

“Clicking links should be safe. What do we have to do to make clicking links safe?” — Matt Johansen

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