In this episode, Damian, Troy, and Fern dive into the 'Wild West' of 2026: Shadow AI.

From autonomous agents paying unapproved invoices to the rinse and repeat of the 2010 cloud revolution, the team debates whether AI agents are productivity miracles or a liability nightmare for the modern CISO.

Timestamps:

⁠00:00 - The $50k Shadow Agent Invoice

01:02 - Fern’s Nightmare Scenario: The AI Agent in Production

02:15 - 2010 vs. 2026: Why Shadow AI is the new Shadow IT

04:14 - Damian’s Technical Deep Dive: The Permission Explosion & Admin Entitlements

⁠11:08 - The State of the Union: CISO Mandates and the "Chief AI Officer"

26:10 - Troy’s CISO Perspective: Managing Identity Governance & Global Risk

40:13 - The Great Debate: Micro-segmentation for AI Agents

46:49 - Final Verdict: Can You Govern What You Can't See?

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Fern: https://www.linkedin.com/in/fernrojasaz/

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Everything here is our personal hot takes — not our employers, not the vendors we roast, not legal advice. Just three idiots with mics trying to keep you from getting pwned.