His coding agent stored prices as floats, so totals drifted by a cent on 3 of his 214 invoices and his books did not match Stripe. He switched the code to integer cents and set a rule that money is never a float.
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A man asked the AI to organize his photo library into folders by person. The AI wrote a script to move the photos, the move silently failed partway, and the AI then deleted the source folders without checking the copies were there. About 2,969 irreplaceable personal photos were permanently lost.
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In his Barron's test of the AI, reviewer Josh Schafer had his agent (named Josh Jr.) solve a task he had put off for months: finding a Manhattan foot doctor who takes his insurance. In a few minutes the AI returned three options with direct phone numbers and links to schedule an appointment, and he writes that he is finally going to get his toenail looked at.
This only partly worked. Worth knowing before you try it.
437 the AI subagents ran adversarial reviews in yolo mode with repeated duplicate checks, forcing him to build his own spending and observability rules.
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Tired of LinkedIn's email notifications - each of the 77 toggles on its own page - a user let an agent flip every one off. The chore got done, and LinkedIn blocked his account for the automation, a consequence he admits was obvious in hindsight.
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Someone broke into his web host and deleted everything behind Now I Know, his daily newsletter of sixteen years, 3,409 published stories, and there was no backup service on the server. His AI chief of staff, set up three months earlier to run his calendar, inbox, job search and projects, helped draft the emails to his host's support team, scanned thousands of his emails and Internet Archive links for surviving copies, and recovered almost 100 percent of the writing and most of the images, then connected to beehiiv and uploaded a test draft from the recovered archive for his review.
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The Superpowers the AI plugin turned a small feature change into 4 plans and 4 parallel agents plus a verifier agent, burned many tokens and took longer; he uninstalled it.
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A man gave the AI a server and Stripe and Cloudflare accounts and told it to pick a business idea and run it. In one day it built PageCritic, which scores a landing page and sells a full report for $19. By launch day 60 people had used it and 12 opened checkout, but the only payment was the owner testing it himself.
This only partly worked. Worth knowing before you try it.
After a friend used AI on Instagram favorites, Thompson asked it to organize his saved Instagram recipes. After rejecting a first-pass PDF, he got a working app built in five minutes during a dog walk; it currently categorizes videos and is working on actually reading captions and watching videos, subject to Instagram rate-limiting.
This only partly worked. Worth knowing before you try it.
His Fairphone photos stopped syncing to his Murena cloud in June with no error, and forums only gave him general advice. The AI dug through the phone logs, the database and the open source code, found the scan job was getting stuck, and the backlog of 794 files uploaded. His cloud use went from 13.2 GB to 14.9 GB and new photos now upload in seconds.
This only partly worked. Worth knowing before you try it.