He is juggling several legal cases of his own, and his lawyers do not have time to answer him every day. The AI transcribes audio, organizes his evidence and writes the case summaries he hands to them. He calls it the best tool he has ever had, and says stopping would mean going back to doing all of that alone.
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.
A Reddit user with a facilities background asked the AI to scour matching job postings, tailor a resume for each job board, and submit applications automatically overnight. Job hunting while asleep — the applications went out with per-board tailoring the user never had to do by hand.
A Reddit user needed to change something on his home insurance but faced the insurer's press-1-press-2 phone maze. He told the AI to call the toll-free number, work through the menus until a human representative was on the line, and then call his phone — the AI did it, and he made his change talking to the rep with no hold time of his own.
The AI’s tools produced printable booth artifacts for a nonprofit he advises; in about 30 minutes he had a professional PDF uploaded to FedEx Kinkos for printing.
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.
He follows the CNN lawsuit over White House press briefing access. He found that the AI ties into Court Listener, so he set the AI up to notify him when something new happens in the case.
This only partly worked. Worth knowing before you try it.
Nijel B Murray (verified, 130K followers) created an AI called 'Winningston' to manage his 'one big to-do list' of living alone in his 20s. Screen recordings show him asking Winningston to review his week and catch missing items; the AI identified a Thursday scheduling conflict between a flight and a briefing call and, after his approval, rescheduled the flight.
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 Business Insider Japan writer gave OpenAI Dots access to his email and calendar. When event and interview mail arrives, Dots pulls out the date and the job and puts it in his calendar. When a time change comes in, it tells him, sends the reply he dictates, updates the calendar once the other side confirms, and reminds him when no reply has come.