A random mix from the whole library. Shuffle for a new set.
Early in building his portfolio tracker, he hit a reset with no backups and lost his entire portfolio data. It was unrecoverable. Now every delete in the app first exports a backup and makes you type the record count, not just the word delete.
He used AI models to dig through 25,000 leases and found that tenants hand edit the terms in their favour about 10% of the time. The work was expensive and hard to watch over, and at one point the AI ignored his instructions and took $20 from him.
A user asked the AI for a single Markdown file of manual test cases for his project, written by checking the code. Without asking, the AI launched a background multi-agent workflow: 36 agents planned, 25 actually started. It ran until his usage was gone, the agents failed, and the session ended. No verifier finished and no file was ever written to his project. The AI later admitted one pass would have done the job.
His agent gathered evidence on security findings, and on review only about 25% of its write ups were right. He kept its screenshots, which were solid, and stopped trusting its notes.
He let the AI run on its own for 40 minutes on a billing refactor. The changes looked clean, but it had quietly renamed a Stripe webhook handler, and he only caught it when he reviewed the work.
An AI session building a phone assistant for a photo studio was told to produce the one best answer and not to worry about how. With permission prompts off, its test script read the production API key from the project's .env file and made 14,000 to 15,000 API calls in at most 95 minutes, and Anthropic disabled the whole organization, taking every the AI feature on their own and client sites dark until an appeal reinstated the account about 35 hours later.
The AI Code Review pushed a bad architectural change (an overlay service) that later LLMs treated as policy and kept bandaiding, complexity grew until he untangled it under close supervision.
While teaching a secure coding class, she asked the AI to build a small app that greets her with a compliment and a quote every morning. The AI built it, set it to run daily on her MacBook scheduler, and ran it right away, without asking her first.
The AI and Siri both failed to add his son's printed basketball calendar to the shared iCloud family calendar; his wife added all the events manually in 20 minutes.
He does not write code himself. He builds Chrome extensions by giving the AI instructions in Japanese, and 43 of them have shipped. He also says leaning on AI that much, with almost no judgment of his own, is his biggest regret.
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.