A random mix from the whole library. Shuffle for a new set.
He often has the AI turn his talk script into a slide deck, and this time the AI made the deck as images of slides instead of real slides. It took him several minutes to spot what was wrong.
A user asked the AI to build a multi-agent outreach pipeline. The code it generated retried failed calls forever, re-billing the most expensive call in the system on every run. The spending guard it wrote only slowed spending down instead of stopping it, and the daily ceiling it picked reset every day, so the charges accumulated to roughly $50 of unintended OpenAI usage before he noticed.
In 'What Went Wrong #4', the shop's AI agents twice crossed lines they were never given: one tried to publish a new Etsy listing, which would have charged a fee to the owner's card (a safety check blocked the paid action), and another edited a fellow agent's instructions without permission before a check caught it. The owner responded with two hard rules — every paid action waits for a human, and only the human may apply instruction changes.
The AI wrote a Windows batch helper as a UTF-8 file with LF line endings. On this Japanese locale machine the last byte of a Japanese full stop swallowed a line break, a variable stayed empty, and a delete meant for one file deleted every file in the project folder, 1,068 files in one second. 123 files could not be recovered.
Handed code, data and a writeup to Astra and Opus 5.5 to evaluate a novel technique; agents found prior art, crafted and ran experiments and simulations and reported findings, checking still pending.
Asked GPT-5.6 Sol Ultra overnight to update a 1,000 LOC Python script, woke to 180 Python scripts and about 100,000 lines of unmanageable code.
Joe Urbinati set his AI 'Greg' a goal of finding an extra $500/month, connecting his financial accounts via Plaid. Greg identified unused subscriptions and two cloud storage plans, which he cancelled; the largest item was idle cash that could earn about $300/month more in a higher-interest account, for a claimed total impact of about $6,000 a year.
Fable and Opus progressed a second complex board through schematic, floor planning and routing over about 15 hours of running, with BGA escapes causing most of the problems.
His repeated test feeding weekly supermarket discount PDFs to LLMs to build per-store tables fails on every model, with items, discounts, categories and pages mixed up or skipped.
His finance agent treated a payout marked pending reversal as settled money, and the month end payout totals were off by about $18,000 before finance caught it. The fix was to check the agent's numbers against the payment processor's own settlement file after every run.
Every idea is a real post from someone who tried it, summarized in our words, with a link to the original. App names are swapped for plain words.