Archive - The Hipster CISO’s Substack

The First Test in Carnegie Mellon's Data & AI Executive Program

...And Why 73% of AI Initiatives Fail Before Models Ever Run

Feb 12 • Thomas Jones

January 2026

How Today’s Cybersecurity Measurements Cannot Support Decisions

continuing a case for measurable cybersecurity

Jan 27 • Thomas Jones

From Security to Data and AI Governance

on accountability, measurement, and enterprise decision support

Jan 16 • Thomas Jones

Why Cybersecurity Measurement Fails Governance Decisions

a case for measurable cybersecurity

Jan 8 • Thomas Jones

December 2025

Judgement Over Noise

Notes from a practicing CISO on risk, restraint, and what actually works

Dec 22, 2025 • Thomas Jones

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