A random mix from the whole library. Shuffle for a new set.
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 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.
Harry McCracken's Dot, Chip, cross-checked his calendar against his email and spotted that a speaking engagement he had entered on one date had been rescheduled by the organizers to a different day, which the confirmation email showed. He says he would otherwise have shown up to an empty room.
Shervin Shaikh asked the AI in chat to find any NYC parking tickets under his name and pay them; after he supplied his licence plate, the AI found a $115 'No Standing' ticket in Brooklyn, now $145 with penalties. The first CityPay attempt failed on a billing-address mismatch, but the retry succeeded: $147.90 paid via Stripe Link, confirmed on screen.
Three family members, three nationalities, one move to Brazil. After a month of human lawyers producing zero progress and dangerously incorrect advice, they were fired and the agent took over - assembling an evidentiary portfolio of dozens of documents that has made bureaucrats happy everywhere it has dealt with them, down to a social-club application demanding apostilled birth certificates.
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.
An economist set up an email bot to bring him any message tagged #handcarry right away. The bot misspelled the tag as #hancarry in its own memory file, made a new folder, and filed a week of urgent emails deep in it where he never saw them.
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.
Gannon Meyer (210K followers) named his AI 'Oscar' (dachshund avatar) to survive 'one of the most chaotic but manageable periods of his life.' The demo shows Oscar drafting and sending an email to a photographer about wedding timing at Perona Farms, removing sales calls from his September calendar, and tracking meals and weight-loss progress toward a wedding goal — while remembering personal context like his recent pickleball ankle injury.
He is treasurer for a nonprofit food co-op. He gave the AI the co-op's financial statements, some notes on what he wanted to explain, and the logos, and 20 minutes later he had a ten slide deck and separate printouts for the annual meeting.
Every idea is a real post from someone who tried it, summarized in our words, with a link to the original. App names are swapped for plain words.