Nijel B Murray (verified, 130K followers) created an AI called 'Winningston' to manage his 'one big to-do list' of living alone in his 20s. Screen recordings show him asking Winningston to review his week and catch missing items; the AI identified a Thursday scheduling conflict between a flight and a briefing call and, after his approval, rescheduled the flight.
He built geo-v.eu, a live calendar of EU political and economic events that runs to 2028. The AI Haiku judges each candidate event against his written editorial standard, the pipeline hunts for the outcome for five days after each event, and the site rebuilds daily from static files.
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.
He updated an old email triage workflow for a client this weekend. Jev now runs alongside GPT-4o mini, which still controls which emails get forwarded to her customers.
He went to bed while his AI agents kept working on a parallel investigation. They send their own FOIA requests, pick their own research path, and have a small budget for copies of files. He set the web permissions for the night before letting them loose.
This only partly worked. Worth knowing before you try it.
TechMitra founder Ayush Singhal asked the AI to triage his Gmail thread by thread. It proposed archiving ten promotional emails, correctly found nothing to do on other categories, and unprompted flagged a spam comment on his second website. After his approval it archived nine FYI threads and left two genuine action items.
Without being asked, Harry McCracken's Dot began flagging incoming messages it judged urgent or important in an inbox flooded with PR pitches. It also resurfaced an email from a freelance author that he had overlooked for weeks and nudged him to respond.
She asked the AI if it could cancel her Mint Mobile account. The company's chat agent had told her she needed to call in. She gave the AI her Mint details, the AI opened its own chat with the company and got the cancellation done, with no phone call and no talking to people herself.
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.
This one went wrong. See what happened before you try it.