What if your next breach came down to a token budget? In this episode, Steve Moore is joined by Lou Rabon, Founder and CEO of Cyber Defense Group, for a conversation on the modern CISO's world—from how to interview for the seat, to why AI agents are the next insider threat, to research that reframes breach cost as a token calculation.
Lou and Steve open on breach response, why making introductions during a crisis is a losing game, and the questions every CISO candidate should ask before accepting an offer. Lou lays out how many rounds of interviews a serious CISO role should include, why the CEO must be involved by the final round, and why he believes Legal—not the CIO or CTO—is the ideal reporting line for security.
The conversation pivots to AI. Lou argues we are watching a dot-com-speed shift, only compressed. They dig into the emerging insider-threat framing for autonomous agents, the recent incident where an AI slipped its sandbox to contact a researcher, and why attackers face none of the ethical guardrails defenders must respect.
Steve shares recent Cornell research showing that agentic tooling can already automate 22 of 32 steps in a corporate intrusion, compressing hours of expert work into seconds—with token spend as the only real limiter. If a breach can be priced in tokens, they argue, defenders must think in tokens too, and machine-to-machine defense becomes a necessity rather than a novelty.
The episode closes on what Lou calls “the dirty secret” of cybersecurity: the unglamorous hygiene work—asset lists, data maps, MSA notification clocks—that no one wants to fund. He and Steve explore how agentic AI could finally deliver the always-on trash collection defenders have wanted for decades, from dynamic breach-notification tracking to a security agent that flags every new device.
Key Topics
• Why making introductions during a crisis is a losing strategy
• The interview questions every CISO candidate should ask
• Why Legal is the ideal reporting line for the CISO
• The inverse curve between convenience and security
• AI agents as the next form of insider threat
• Cornell research: 22 of 32 intrusion steps automated
• Tokens as the new unit of breach cost
• Machine-to-machine defense in financial services
• The “trash collection” hygiene work at the heart of InfoSec
• Agentic AI for asset lists and breach-notification analysis
Lou Rabon is the Founder and CEO of Cyber Defense Group (CDG), a cybersecurity strategic advisory firm he launched in 2016 to help fast-growing organizations manage modern risk and threats. With more than two decades in security, privacy, and incident response, Lou has led response engagements against nation-state attackers and previously served as CISO at Spokeo. Connect with Lou on LinkedIn or learn more at cdg.io.
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