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