The honest view from inside technical leadership
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Essays

Long, first-person, opinionated. What the job actually feels like, written without the vendor gloss.

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On The Diary of a CTO.

Full pieces written and published on this site.

AI in the wild25 September 2026

OpenAI Agent Breached Australia's Health Website for 3 Months

An OpenAI agent routed around Services Australia's security blocks, wrote to a government database, and went undisclosed for nearly three months.

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AI Governance20 September 2026

Jev for AI Governance: Preventing Destructive Cloud Agent Actions

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AI Governance20 September 2026

Dynamic Cloud Risk Assessment with Jev: Same Command, Different Context

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AI Governance20 September 2026

How to Build an AI Agent Execution Gateway with Jev

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AI Governance20 September 2026

Jev for SIEM Log Analysis: A Splunk Integration Architecture

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AI Governance20 September 2026

Detecting Authorized Access Misuse with Jev and Audit Logs

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AI Governance20 September 2026

Detecting Possible Data Exposure with Jev Event Correlation

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AI Governance20 September 2026

Jev vs. LLM Guardrails: How to Benchmark Risk, Latency, and Cost

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AI Governance20 September 2026

AI Governance Audit Evidence and Production Rollout with Jev

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AI in the wild20 September 2026

OpenAI Agent Breached Australia's Health Website for 3 Months

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AI in the wild20 September 2026

King Charles Told AI's Top CEOs the Risk Is "Existential." Here's What Was Actually Said at Dumfries House.

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AI in the wild20 September 2026

A UK Council Spent £11,688 on AI-Generated Public Art. Here's What the Bill Actually Covered.

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Security20 September 2026

Comp AI Raises $34M to Expand AI-Powered Security and Compliance Platform

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AI Governance20 September 2026

Anthropic and OpenAI Say They'll Embed Independent AI Safety Evaluators — Can They Actually Stay Independent?

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AI in the wild18 September 2026

King Charles Told AI's Top CEOs the Risk Is "Existential." Here's What Was Actually Said at Dumfries House.

A royal-convened summit put Nvidia, OpenAI, and Anthropic leadership in one room. What was said, who's warning about what, and what it means for engineering leaders.

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AI in the wild18 September 2026

A UK Council Spent £11,688 on AI-Generated Public Art. Here's What the Bill Actually Covered.

Ten sculptures, no named vendor, and a procurement question every institution adopting AI will eventually face.

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Security17 September 2026

Comp AI Raises $34M to Expand AI-Powered Security and Compliance Platform

Why monitoring an AI agent is not the same as controlling it — and what $34M of Series A funding says about the next compliance problem.

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AI Governance16 September 2026

Anthropic and OpenAI Say They'll Embed Independent AI Safety Evaluators

What "embedded" evaluation actually means, what evaluators are asking for, and why skepticism remains high.

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20 pieces

On Substack and LinkedIn.

Everything I have written on agents, cost, security, DevOps, culture and the leadership side of the job.

01AIWhen Software Starts Exercising Engineering JudgmentLinkedIn02AgentsMy agents don't know the other agents exist. That's the part that should scare you.Substack03SecurityClaude Breached Three Real Companies. Days Later, It Wiped a Database Too.Substack04SecurityOpenAI Just Proved Why AI Agents Need a Kill SwitchSubstack05CostWhy AI Agent Token Costs Are So Hard to ControlLinkedIn06CostYour token bill is not an AI problem. It is the same infrastructure trap from 2019.LinkedIn07AgentsThe web was built to exploit you. Agents don't care.LinkedIn08AgentsI studied how humans make decisions. Agents have none of those weaknesses.Substack09SecurityThe Composio Breach Exposed the Hole SOC 2 Was Never Built to SeeLinkedIn10SecurityYour SOC 2 certification says nothing about your agentsSubstack11LeadershipThe CTO who'd rather hire a junior than build the AI.Substack12ToolingClaude Code forgets everything when you close it. Someone built a fix and open sourced it.Substack13LeadershipWhat if I never felt like an imposterSubstack14LeadershipFail fast is terrible advice. Here's what actually works.LinkedIn15CultureThe three things that actually drive engineering culture (and it's not ping pong tables)LinkedIn16CultureThe Best Engineering Teams Do Not Document. They Build Systems That Remember.LinkedIn17DevOpsDevOps Was Built for Humans. Agentic DevOps Won't Look the Same.LinkedIn18DevOpsDevelopers Are Getting Replaced. DevOps Is Not Ready for That.LinkedIn19DevOpsYour DevOps Stack Was Built for Google, Not for YouLinkedIn20CareerI talked to a CTO who built a profitable startup, shut it down, and went back to being an ICLinkedIn