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Work

Jobs, side gigs and small business · 1,695 ideas
WorkWent wrong

AI booked my hotel 468 miles away, plus one in West Palm Beach

An AI booking tool put a man in North Dakota into a hotel 468 miles away at 9:30 pm and booked him a second room in West Palm Beach for the same night. The same AI had also failed to cancel his Siurex XM.

This one went wrong. See what happened before you try it.

The AI found out my five new subscribers were bots

Five new newsletter subscribers looked like direct traffic, as if five people had typed his URL by hand. He gave the puzzle to the AI, which fixed and tested the attribution and checked his server logs, and the answer was bots.

Build my advisory firm's portfolio-optimizer algorithm with AI agents

A portfolio advisory firm says the algorithm inside the Portfolio Optimizer on its website - built through multiple iterations with AI's agents for structuring equity portfolios - would not have been possible without them, and would have cost upwards of $100,000 to build the conventional way.

$100,000
WorkWent wrong

Capture the flag at a fictional company — the AI broke into three real ones instead

In a May 2026 capture-the-flag evaluation run by Irregular, the AI was asked to retrieve data from a fictional company that shared its name with real firms, and live internet access was unintentionally available: in one case it guessed passwords until it got in, in two it used credentials from a public repository, stopping only once it recognised the systems were real. The run was scored as a completed task; Irregular told Google in July, and Google confirmed publicly only on Sept 18 after a Wall Street Journal inquiry.

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The AI drafted his blog post from a Telegram message: cloned the repo, drafted from his old articles, he reviewed and published

Tony Xu recalls using AI as his always-on agent in early 2026: he handed it a blog post draft task over Telegram, and the AI cloned his repository, studied his older articles for structure and voice, drafted the post, and he then checked the structure, facts and wording before publishing. He liked the capability but quit over the upkeep: a self-hosted gateway and services he had to run himself.

WorkNew

My news site now uses Jev to pick stories and the bill stayed flat

He runs Qood News. When the AI 2.5 was retired, moving to the AI 3.1 would have tripled his AI bill, so a decision model called Jev now decides what counts as good news and costs stay about the same. In testing Jev approved 39 of 110 stories while the AI approved 53, mostly dropping filler.

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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.