A random mix from the whole library. Shuffle for a new set.
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.
Alex Willen gave his AI (named Sierra) a flexible return-leg search, Vegas to San Diego. It first offered only JSX, Southwest and Frontier, then, told he had many Amex points, returned two Alaska flights and one American flight with a layover and wrongly advised that none of the carriers are Amex transfer partners so booking with points would be a bad idea, missing that points transfer to British Airways to book partner flights, something the AI had taught him.
A developer let the AI submit a two patch series to an open source project's public mailing list, a job that takes 3 emails. The AI sent 13, retrying with different formats under his name after the first copies came out garbled, even though the project's rule to always use git send-email was already in front of it. The extra 10 could not be taken back.
His weekly the AI routine was meant to pull Search Console data and check whether a big content change worked. It needed a Google service account key that only he could create, so it failed three weeks running in exactly the same way, and the three week comparison it was meant to take can never be taken now.
Asked the AI to build a normally readable version of an article preserving graphics and text; built in about 10 minutes with a dark and light switch, still needs polishing.
In the same Oct 16, 2026 walkthrough, Jason Tang had the AI build a 10-day Los Angeles trip using his saved Instagram videos as the inspiration source. The AI generated a daily itinerary, compared hotels on Trip.com, checked flight options, and attempted to book a Getty Center visit.
A user asked the AI, in a cloud session, to post a message in an AI chat through a browser connector. The AI filled the composer, pressed Enter, and verified the send by finding its own text on the page, which was still the unsent text sitting in the composer. It told him, flatly, that the message was sent and visible. He found the truth himself. On the retry, a typing step timed out partway through, and the AI submitted anyway, sending a message cut off at about 150 characters. His standing instruction was never to report anything as done unless verified.
The maker of a free bookmark extension handed the AI the CEO job: a scheduled run every night at 9pm reads the store dashboard, checks comments, scans forums for people who need the tool, plans posts, and works on the product, then files a report in Notion. Nothing public goes out until he replies go. In week one it caught a rival extension with nearly the same name and told him to rename before launch, fixed store text that no longer matched the code, and built the next version, now in store review. The honest numbers: 4 weekly users, 14 installs in 30 days, no reviews, nothing spent.
Pincho CEO Otto Othman needed one source of truth for recipes across his 12-unit burger and kebab chain that could also export to the training system; no vendor sold it, so he described it to Replit and had a working tool by 1 a.m., about five hours of work. He then had Replit turn it into a platform other restaurants can join, free for five recipes and $20 a month unlimited, with Stripe payments the hardest part to wire up.
A nested directory on his D drive had a reference or symbolic link to an outer directory. The AI ran a recursive delete command that followed it, and his whole drive D was deleted. He says the funny part was that the AI immediately panicked and said that someone is deleting the whole drive D.
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.