Claire Vo, a parent and Lenny's Newsletter contributor, asked the AI for a one-page family morning newsletter PDF: the week's agenda, call-outs for each kid (it flagged overlapping jiu-jitsu and piano), kid-friendly news with 'Talk at the Table' prompts, and local San Francisco events. It's the strongest parent-life use case in the dataset — synthesis across calendar, kids' activities, and local events into one artifact.
A builder used AI to make a 'describe your situation' tool over Australia's official welfare pages: it takes a one-sentence description, works in 24 languages and shows which Services Australia payments might apply, each linked to its official page. Across 43 test questions it invented zero payments and refused correctly 100% of the time, with payment recall of 0.76.
Before a speaking engagement, Ulanoff couldn't recall where he was talking or where to park. He asked the AI to find the original note from his contact, misspelling the contact's name.
He asked the AI to screen his unread Instagram threads one morning. It came back with 50 unread, looked at the threads he named across his Primary, General and request folders, and told him what people had sent. The unread count was still 50 afterward, so nothing showed as read for him or for the senders.
A young man in sunglasses sitting in his car tested the AI by uploading his resume and target job roles, then instructed it to apply to jobs while he went to lunch. Screen recordings showed multiple browser tasks running and a notification confirming an application submitted to 'ioTech Solutions.' The AI asked for information once for the first application, then reused it — resulting in 50 applications submitted while he was idle.
Going through a complicated divorce in the UK, he used Cowork for the legal work instead of paying a solicitor for all of it, and says it saved him thousands in legal costs.
German creator Chris Marvin Atsu gave an AI agent access to his calendar and email; spotting a booked flight on the same day as a client mentorship call, the agent assumed a conflict and cancelled the appointment by email on its own — the first time it had sent anything he didn't authorise. He found the cancellation after the fact and now warns viewers about handing agents that much autonomy.
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Kicker emailed Newton's speaking agent, with his permission, to clarify a potential scheduling conflict in November. The task was one of several background jobs it ran during a single afternoon.
Daniel, who sells window shades and blinds, says he has 'a personal assistant for free' in an AI app (noting he doesn't benefit from downloads). Based on his prompt, AI messages him daily at 7 AM with a simple briefing compiled from emails, Google Calendar, Apple Calendar, and reminders; he held up a printed example showing timed tasks like submitting orders, texting contacts, and appointments.
After his motorcycle was stolen, his insurer offered nearly half the market value. He had Cowork build a 20 page report on the claim, and the insurer paid the full amount.
A man asked the AI to prepare a compliance letter to a US state agency to get his driver license reinstated, and to send it from a named email account. He had typed his license number one digit short in his note, the correct number was in a photo in the same folder, and the AI itself had flagged the mismatch. The letter still went out with the unverified number in the PDF and the email. The correction was then sent from a different account than the one he had named.
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X user someone (Charlie) gave the AI inbox access at the start of a deep personal-data experiment. In one of the standout moments, the agent surfaced an important message he had missed, drafted a response, co-edited it with him, and sent it — an agentic loop (find, draft, revise, send) rather than a one-shot draft.
He and the AI built a live website where anyone can look up what a politician has ever said in Parliament on a topic they pick. He calls it a moral manoeuvrability monitor.
She was using AI to archive legislative material when it flagged a serious vulnerability in a state legislature's website. She had to stop and report it.
One user’s the AI unsubscribed him from newsletters, found a recurring credit-card charge he had missed and cancelled it, and booked a B&B for his wedding anniversary. Three different errands, one agent, all completed.
In Diana's inbox-prioritization test, the AI produced a useful organized view but concluded she hadn't sent an email she had in fact sent — the thread structure and CCs confused it. If she'd trusted the first answer, she'd have sent a duplicate email.
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Gaby Hersham built a nightly automation in which the AI reads the roughly 20 school emails her family gets each week and adds the important dates to the family calendar, ending the manual trawl through newsletters and PDFs.
Tech journalist Lance Ulanoff connected his personal Gmail to his AI 'Charlie' and asked it to check for anything pressing he had missed. The AI reported nothing on fire but flagged three items worth a glance: a Google security alert from the connection itself, a cell-service account-change notice, and an embargoed PR pitch from 'Bill' — which he then opened, had the AI draft and send a reply to.