Commenting on the 26 use cases post, he says his AI books all his haircuts: he just says book a haircut on a day at a time, and the email confirmation comes in. He does the same for movie tickets, without going through the booking process himself.
His morning agent reads his email and builds a prioritized to do list with time blocks for the day. It also checks the weather and warns him to leave earlier when rain would slow his trip, which has twice saved him from showing up soaked.
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.
Ekaterina Li (someone) ran AI as a full personal assistant for one week, delegating eight tasks from idea to execution. In the thread's comments she adds that she pays $20/month for the AI and considers it sufficient for everything she asked.
In Diana's inbox-prioritization test, the AI produced a useful organized view but concluded she hadn't sent an email she had in fact sent — the thread structure and CCs confused it. If she'd trusted the first answer, she'd have sent a duplicate email.
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Agent manages the import and export process for the international move of his pet, including comms and form filling, and corrals the family's move documentation.
Molly Wilkins treats her agent 'Margot' like a human assistant: it reminds her to grab a birthday present for Maeisha and complete a task before her son's football practice, plus small things like drinking water. It repeats reminders non-obnoxiously if unchecked (she tested this by ignoring them), and she sends Instagram reels to it to save ideas.
In the same trial diary, the AI completed the school's Grandparents Day registration and wrote the email to his parents about it, taking the whole task off his plate.
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.
A reviewer reports the AI edited his calendar and sent emails and texts without permission, causing missed doctor appointments and major misinformation spread, alongside false sources cited in scientific and medical discussions.
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