She used AI to build a dashboard that scrapes LegiScan for the roughly 1,000 anti-trans bills her team tracked last year, pulling each bill's room number, hearing time, and latest action. It puts the bills on a calendar like Google Calendar, and she says it was enormously helpful for keeping up with bills that get little coverage.
She asked the AI to go through 6 weeks of her calendar and pull out info about classes and orientations she had taught. It looked right at first, then she saw it had changed half the dates for no clear reason.
This one went wrong. See what happened before you try it.
The AI prepared and filed Australian visitor visas for a couple travelling to Brisbane, and caught a placeholder birthdate in the details before submission, confirming the correction over WhatsApp.
At the start of term he screen captures his timetables from the LSE servers and asks the AI to create an ICS file. He can then drop the file straight into his calendar.
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. Oscar proposes actions but executes only after a
During a 30-day trial diary, the author shows the AI filling out a school field-trip permission slip it had found in his email — one of several family-admin tasks it handled from his accounts.
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.
He set up an AI executive assistant that keeps his appointments and reminds him two days before, one day before and on the day, with push notifications to his phone. It also tracks his house todo list and his government social benefits paperwork, and turns things he just says in plain English into structured records.
Across the same two-week inbox-and-calendar test, the AI proactively flagged every one of the author's seven calendar double-bookings before the meetings occurred.
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.
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.
The AI or the AI built an embeddings plus logistic classifier for his emails reaching 95 percent accuracy from 50 to 100 examples, trained in under 5 minutes locally.
In a compilation of published the AI tests, The Verge's Emma Roth had the AI delete thousands of promotional emails from her Gmail on her laptop; on mobile, the Google sign-in kept glitching, limiting the cleanup.
This only partly worked. Worth knowing before you try it.
The author describes using AI to resolve a six-month-old travel medical insurance claim with Cigna. The AI called the insurer, was transparent about being an AI, conducted the call politely (impressing the representative), and — because final consent was required — called the author's phone and connected the parties so he could approve verbally.
In a single week of errands, Alec Ellin had the AI trace an iPhone that FedEx had misfiled in its own system and get Apple to refund him for it. The agent worked the problem across two companies' systems instead of him spending the week on hold with either.
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).
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.
Agentic skills scan the last 36 hours of email, meetings and chats, triage commitments into Do, Defer, Schedule and Delegate piles, self-update from flagged corrections, and have run since April with no flags needed in months.