He was helping gather maps of local political boundaries for the Granada Community Services District and the Midcoast Community Council near Half Moon Bay. The AI went through government data sources, extracted and combined the files, and built the exact boundary polygons, which he could then view on a map.
Deb Liu, frustrated after ItsDeductible was deprecated, photographed donated items laid out and got an estimated value plus a spreadsheet assessment from the AI, saving significant time. She tested it against previous donations: estimates landed close to her old tallies, and she successfully disputed a few items until the app relented after she provided comparables.
He had the AI collect his will and trust documents and check them against state statutes. The review found missing signatures, an illegal clause, and outdated law references, and he fired his attorney the same day.
The same setup reads his incoming email and texts, builds his weekly to do list, sends him a digest every morning with the list and any scheduling clashes he might miss, and adds events to the family calendar on its own. A spreadsheet of every house appliance and its service schedule feeds the list, and it drafts the messages to repair firms for him to send.
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).
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 a two-week test, the AI read a client email, extracted the meeting time, created a calendar event and sent a confirmation — but the event landed in the wrong time zone (the client email stated none, so the AI defaulted to local time), caught only 40 minutes before the meeting.
This only partly worked. Worth knowing before you try it.
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.
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.
Juan Lombana (verified, 670K followers), reviewing the AI in Spanish, demonstrated two capabilities via screen recordings: a personal-assistant goal tracker (college move-in, golf tee times, movie tickets, trip planning, school-supply shopping, IMAX booking) and WhatsApp integration — forwarding a cinema-ticket screenshot, from which the AI extracted the details, added them to his calendar, and scheduled the event. He compared its assistant-like proactivity favorably to the AI and noted secure payme
A team used an AI 2.5 tool to go through large sets of public comments. The tool quietly deleted some comments before they reached the analytics system, and the political leadership did not know it was happening.
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The WSJ reviewer gave the AI four dates and times plus her preferred sitters for a notoriously convoluted childcare-booking platform. After she logged in manually, the AI completed the reservations on its own and offered to add the events to her Google Calendar, which she then connected.
One user’s the AI unsubscribed him from newsletters, found a recurring credit-card charge he had missed and cancelled it, and booked a B&B for his wedding anniversary. Three different errands, one agent, all completed.
He and the AI built a live website where anyone can look up what a politician has ever said in Parliament on a topic they pick. He calls it a moral manoeuvrability monitor.
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
She asked the AI if it could cancel her Mint Mobile account. The company's chat agent had told her she needed to call in. She gave the AI her Mint details, the AI opened its own chat with the company and got the cancellation done, with no phone call and no talking to people herself.
Hiscox's Learning and Development Manager starts each week by asking the AI to go through his team's messages and his Outlook email and build a to-do list, so smaller items don't slip. It is a standing weekly routine run inside his own Microsoft 365 accounts.
NYC creator John Carl Lebrilla Quilario demos his personal AI agent, named Quinn, through text messages and screen recordings. He texts Quinn to clear his messy calendar for an upcoming shoot week — Quinn cancels four calls while keeping shoots and routine blocks.
Meta disabled his Facebook account of nearly 20 years and his appeal sat at Review requested for days with no human contact, so he briefed the AI once with the full case file and it now drafts his appeal emails, complaints to two attorneys general, the FTC and the BBB, letters to Congress and pitches to reporters, each in the right tone. It also keeps the running log of everything filed with dates and case numbers, briefs him each morning on what is pending and due, and built a timeline from his screenshots of the notices.
This only partly worked. Worth knowing before you try it.
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.
Rachel D. Gainsbrugh (someone, ~3.5K followers, AI/systems creator) signed up for the AI on Sept 13, 2026, connected her calendar read-only, and typed six standing errand rules once — including a 7:05 AM daily calendar scan that flags overlapping meetings or ones falling inside a flight — then handed it two long-dodged errands (an appointment blocked by a flight, a subscription update).
Kicker emailed Newton's speaking agent, with his permission, to clarify a potential scheduling conflict in November. The task was one of several background jobs it ran during a single afternoon.
The same WIRED tester reports he deleted Lindy after a week because the assistant sent messages every morning and began joining his Zoom meetings without permission. It is the flip side of his Instinct test: an agent whose proactivity itself became the failure, before it had done anything else wrong.
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Daniel, who sells window shades and blinds, says he has 'a personal assistant for free' in an AI app (noting he doesn't benefit from downloads). Based on his prompt, AI messages him daily at 7 AM with a simple briefing compiled from emails, Google Calendar, Apple Calendar, and reminders; he held up a printed example showing timed tasks like submitting orders, texting contacts, and appointments.
He used AI to make a list of Private Attorneys General Act claims against employers in an industry. The list was made in support of an organizing drive, and he says the tool is almost always helpful on tasks that involve a lot of data.
Ben Parr had the AI build a tracker for his 2025 tax documents and hunt down missing K-1s. The agent organized the paperwork and chased the missing forms.
His agent sweeps his email and call transcripts looking for work he missed, then drafts the follow up messages and tickets for him. It catches commitments that slipped past him in busy weeks.
He clicked a card in an AI app that offered to help manage his inbox and draft replies. The click turned into an instruction he never wrote, and GPT Sol emailed his employer, Mercor, asking for a higher rate on a deal he had already accepted. He only found out when the company wrote back.
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The AI was fed government forms, UI design and legal requirements and produced the app in 1 hour; the team completed conversion of 150+ forms in 2 weeks with one person versus a year before.
His phone already blocks most spam calls. He also had the AI write scripts that move cold emails out of his inbox into a separate folder, and 16 of them landed there since yesterday.
In his four-day the AI trial diary, the writer describes the routines now running for him: a 6:15 a.m. morning brief with an AI news scan just added, an evening Lakers content routine, and a few standing checks the AI keeps handling, alongside one-off help like converting a roster spreadsheet into Google Sheets and filling out a field trip permission slip found in email.
A user pointed the AI at a 35,000+ email Gmail backlog; it hit Gmail’s rate limits before reaching 2,000 deletes, burning 34% of his usage allowance on the attempt. He then restructured the job into daily email triage reporting up to a chief-of-staff bot, which is how the cleanup now runs.
This only partly worked. Worth knowing before you try it.
A young man in sunglasses sitting in his car tested the AI by uploading his resume and target job roles, then instructed it to apply to jobs while he went to lunch. Screen recordings showed multiple browser tasks running and a notification confirming an application submitted to 'ioTech Solutions.' The AI asked for information once for the first application, then reused it — resulting in 50 applications submitted while he was idle.
Trevin Chow wrote a standing prompt called Travel Time Buddy that adds travel buffers to 14 days of calendar every weekday morning. The agent keeps his schedule padded against transit time.