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.
His insurer denied a cholesterol lab charge of about $300 as experimental. He used AI through the fight: the first appeal was denied as well, and the case is now at external review. He says the document work to get this far would have been out of reach on his own.
$300one time
This only partly worked. Worth knowing before you try it.
Cat (green glasses, plaid shirt), preparing for an interview with limited time, introduced 'Brio' (pink abstract avatar) as her AI. Screen recordings of a messaging app show her asking Brio to block calendar time; Brio confirmed a 2:00-3:00pm block and offered to run through questions.
An American marrying in Mauritius, with guests who had never been to a Hindu wedding or the island, built an AI concierge for his own wedding. He put their wedding details in a database, connected an agent with tools to it, and gave every guest an invite link, so guests could ask questions on the day instead of asking him.
The developer set a scheduled job in plain words: every weekday at 8:30, send events from all calendars plus emails needing a reply, in five lines or fewer. The first run arrived at 8:44 with an apology for the delay, covered all 16 calendars, removed duplicate events and listed private events by time only.
Volunteered and built a cartography data pipeline with coding agents for an educator, integrating sources updated every few minutes so new maps appear within about 5 minutes on a low-powered machine.
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.
Calling sellers about his orders was one of Josh's biggest pain points — so the AI took it over: it called a seller to correct his shipping address, and called a seller to resend his missing orders.