Rachel D. Gainsbrugh (someone, ~3.5K followers, AI/systems creator) signed up for the AI on Sept 13, 2026, connected her calendar read-only, and typed six standing errand rules once — including a 7:05 AM daily calendar scan that flags overlapping meetings or ones falling inside a flight — then handed it two long-dodged errands (an appointment blocked by a flight, a subscription update).
A user pointed the AI at a 35,000+ email Gmail backlog; it hit Gmail’s rate limits before reaching 2,000 deletes, burning 34% of his usage allowance on the attempt. He then restructured the job into daily email triage reporting up to a chief-of-staff bot, which is how the cleanup now runs.
This only partly worked. Worth knowing before you try it.
Agency owner Rui Fu (someone, 253K followers) demonstrates the daily system he shows for the AI: an 8 AM scan of the last 24 hours of Instagram DMs, categorised into brand partnerships, collaboration requests, fan messages and spam so he wakes up to only the important ones. The tutorial also shows an auto-reply rule for guide inquiries and offers his prompt guide in exchange for comments.
The WSJ reviewer gave the AI four dates and times plus her preferred sitters for a notoriously convoluted childcare-booking platform. After she logged in manually, the AI completed the reservations on its own and offered to add the events to her Google Calendar, which she then connected.
Several Hiscox employees independently built the AI Studio agents that extract contact information from emails, and the duplication was treated as a demand signal: the individual solutions are now becoming a larger shared business project with data science, technology, cyber and risk specialists involved.
His local school division released the raw answers to a touchy redistricting survey as one PDF of more than 3,000 pages, which nobody could realistically read. He used AI to write scripts that pulled the answers out and built a public web page where people can search the responses and filter them by keyword and by school.
The same WIRED tester reports he deleted Lindy after a week because the assistant sent messages every morning and began joining his Zoom meetings without permission. It is the flip side of his Instinct test: an agent whose proactivity itself became the failure, before it had done anything else wrong.
This one went wrong. See what happened before you try it.
Ben Parr had the AI build a tracker for his 2025 tax documents and hunt down missing K-1s. The agent organized the paperwork and chased the missing forms.
He had the AI translate his MaPollution app into Italian, and it took 30 minutes. He can now offer his free service to people who speak other languages.
He had the AI work out how the When2Meet scheduling site works and turn it into a skill. Now the AI can read his calendar and fill in the When2Meet availability grid by itself.