In a Vox feature on personal agents, entrepreneur Matt Van Horn said his wife sent Instinct a photo of a parking ticket with no instructions at all. The agent, which already had her credit card on file, simply paid it.
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.
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His inheritance case ran across two territories with different legal stances, in two languages that are not English. Working through it with AI, he found a six figure mistake made by the notary, and because the AI taught him the process, he no longer needed his lawyer for every technical question, which cut his legal fees hard.
The road to a takeoff spot they fly from was not on OpenStreetMap, though satellite images showed the track. They built a tool called osmctl, and the AI drove it and mapped the road.
The same setup reads his incoming email and texts, builds his weekly to do list, sends him a digest every morning with the list and any scheduling clashes he might miss, and adds events to the family calendar on its own. A spreadsheet of every house appliance and its service schedule feeds the list, and it drafts the messages to repair firms for him to send.
Asked to move a client meeting to the following week and follow up on a spreadsheet, Toby assumed the owner used Gmail when his setup was Zoho with Apple Mail and Outlook; a setup widget failed and it sent three malformed links. Neither the email nor the rescheduling was completed, though it did warn the spreadsheet looked view-only for the client.
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Across the same two-week inbox-and-calendar test, the AI proactively flagged every one of the author's seven calendar double-bookings before the meetings occurred.
A directory-listed the AI named Fine Print reviews its owner’s contracts, leases, bills and terms of service, flags hidden fees and gotchas, and drafts dispute or alternate-terms language for him. It is a standing reviewer for every document he is asked to sign.
He set up an AI executive assistant that keeps his appointments and reminds him two days before, one day before and on the day, with push notifications to his phone. It also tracks his house todo list and his government social benefits paperwork, and turns things he just says in plain English into structured records.