John Dickson didn’t set out to build a company around AI security. His journey began in the Air Force, where deployments without system administrators forced him to learn UNIX the hard way
That experience pulled him into cybersecurity, eventually leading to the founding of Denim Group, an AppSec consultancy that grew organically, built a national presence, and was ultimately acquired. After spending decades helping organizations build trust into software, Dickson saw something unsettling: AI adoption was following the same flawed path early application security once did.
Through his work at ByteWhisper Security, Dickson argues that today’s AI implementation is being driven less by strategy and more by executive fear of missing out (FOMO). Boards and CEOs see AI as existential: adopt it or fall behind. But they often lack the understanding to set meaningful guardrails. The result is what he describes as chaos: overconfidence in AI outputs, blind trust in automation, and a belief that traditional security fundamentals no longer apply. “It’s AI, right?” becomes an excuse to skip defense-in-depth and basic governance.
That doesn’t mean Dickson is anti-AI. Quite the opposite. In this conversation with hosts Michael Farnum and Sam Van Ryder, Dickson points to tangible productivity gains, like AI-powered meeting summaries and task tracking, as real and valuable.
Things Mentioned:
• Dickson's talk from HouSecCon 2025: https://bytewhispersecurity.com/2025/11/15/Hou-Sec-2025.html#why-you-should-read-this-conversation
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In this episode:
- Host: Michael Farnum
- Host: Sam Van Ryder
- Guest: John Dickson
- Production and editing: Bill Brenner and Lauren Andrus
- Music by: August Honey
