The same Cowork setup checks his father's email for work orders and schedules his father's meetings automatically. He turned off data sharing with AI for this, so the mail is not saved anywhere else.
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 uploads his own data and points the AI to specific sources and documents, with examples he made before to show the format he wants. The AI then builds the tables and graphics for his Education Rights Project, public pages on education rights and funding in US states, with policy briefs, slide decks and interactive widgets.
A user ran a recurring agent loop that reads his Gmail in Chrome through desktop automation. He then joined a live Google Meet job interview in the same browser window. On its next tick the loop addressed the active tab instead of its own Gmail tab and navigated the interview tab to the inbox, kicking him out of the call. Its attempted undo navigated away a second time, and restoring the Meet link reloaded it a third time. Each reload wiped the live captions he was relying on, and the caption history is lost permanently.
This one went wrong. See what happened before you try it.
He could not think of a coding project, so he had the AI build a tool that checks the poll aggregators for new polls and puts them on one page. He now hears about new polls about five minutes sooner.
Casey Neistat, invited by Meta to test the AI, shows his inbox of 9,209 unread emails and his agent 'Hal' at work: it creates a daily folder containing only the emails that need a response and drafts replies in his voice for him to review and send. He concludes that after decades of email frustration the problem is solved.
Created a UK council planning applications scraper with AI, which also built a debugging front-end and MCP interface he checks regularly for run status and coverage gaps.
Jack created a recurring daily website-check goal by chat in about a minute, then deleted it by chat. The Goals tab itself was slow to load (once 25 seconds, once stuck on placeholders).
He runs his email agent on a 2018 computer he already owned. It watches his inbox, flags what matters, sums up threads, finds old emails by topic, takes voice notes and drafts replies, and a second program watches it and messages him within a second if it breaks.
This only partly worked. Worth knowing before you try it.