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Will AI Steal My Data? A CMO’s Guide to AI Privacy in 2026

October 30, 2026October 30, 2026 by Jonathan Milne

Flat illustration of a chat window locked with a violet padlock beside a smaller open chat window losing papers: paid AI plans protect your data, free accounts leak it

Does ChatGPT train on your company’s data? It depends on the plan you pay for. How CMOs can use AI safely, win over compliance and get their teams moving.

The AI iceberg: leaders see the tip, teams carry the rest

October 30, 2026October 28, 2026 by Jonathan Milne

Two-panel cartoon of an iceberg cut away at the waterline. Left: on the small tip, a smiling leader in a deck chair types on a laptop; a close-up bubble shows the screen reading "Another quick tweak...", and a block of ice falls off the tip into the water. Inside the huge underwater part, four tired team members strain to hold up ice blocks labelled New angle, New guests and New venue. Right: the close-up bubble shows "Daily AI limit reached. Try again tomorrow." and the leader slumps over the laptop. Inside the now smaller underwater part, the team cheers, throwing broken pieces of ice into the air like confetti.

A leader hits a daily AI limit and the team below the water throws confetti. What quick AI pivots really cost the people underneath.

AI Was Supposed to Replace Us. Instead, AI Needs AI to Check It.

October 30, 2026October 19, 2026 by Jonathan Milne

A growth chart of handwritten notes from an AI, taped higher up a wall each month: Confirmed against the spec before sending, diff attached at the bottom, shrinking to Shipped it near the top, where the highest mark has no note at all, just a torn paper corner. Below it, a monitor shows a DEPLOY FAILED error reading missing required field.

A wall of handwritten notes from an AI gets shorter every month, until the last one is a torn corner, and someone still has to check its work.

The drinking bird got promoted

October 30, 2026September 23, 2026 by Jonathan Milne

Three-panel cartoon: a person works at a desk, then slumps clicking Approve, then the chair is empty and a drinking bird toy presses the key.

The job used to be deciding. Now it’s clicking Allow until a desk toy could do it. A cartoon about approval theatre, and what a real gate looks like.

Copying AI Skills Is a Trap: Why Building Your Own Keeps You Valuable

October 30, 2026July 15, 2026 by Jonathan Milne

Flat illustration of one custom violet puzzle piece standing out from a row of identical grey copies

I copied an AI skill and knew within ten seconds it sounded nothing like me. Then an AI-written one bombed a live demo. Building your own keeps you valuable.

Wiring Claude Code Into a Hostinger WordPress Site: the Honest Playbook

October 30, 2026July 15, 2026 by Jonathan Milne

Flat illustration of a terminal window linked by a key to a server, representing SSH access to a WordPress site

I burned an hour and a pile of AI credits on a 401 that lied to me. The fix wasn’t a smarter model. It was SSH. Here’s the real playbook, mistakes included.