His claim was too small for a lawyer and the insurer had frozen it at $4,430, so he worked it himself with AI holding every letter in order. The agent surfaced six dated contradictions in the adjuster's own letters, including a legal basis for denial that changed three times, and reviewed each of his drafts as opposing counsel before anything was sent. After his letter quoting their own paper back at them, the offers climbed: $6,500, then $8,000, then $8,750, and the insurer accepted his split of the last gap the same morning, at $10,250.
Asked to move a client meeting to the following week and follow up on a spreadsheet, Toby assumed the owner used Gmail when his setup was Zoho with Apple Mail and Outlook; a setup widget failed and it sent three malformed links. Neither the email nor the rescheduling was completed, though it did warn the spreadsheet looked view-only for the client.
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Without being asked, Harry McCracken's Dot began flagging incoming messages it judged urgent or important in an inbox flooded with PR pitches. It also resurfaced an email from a freelance author that he had overlooked for weeks and nudged him to respond.
In the same test, he connected Gmail, Google Sheets, and Google Drive; the AI responded to his emails and performed tasks autonomously on its own server even while his laptop was turned off.
The road to a takeoff spot they fly from was not on OpenStreetMap, though satellite images showed the track. They built a tool called osmctl, and the AI drove it and mapped the road.
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.
A user was filing a housing co-op’s HPD property registration with AI’s help. Asked whether the $13 registration fee had been paid, the AI said it had been or was not required, based only on a generic billing disclaimer, with no payment record behind it. Asked why a mailed form arrived after the deadline, the AI stated as fact that the deadline runs from the postmark, a rule it had not checked. Both claims were corrected only after he challenged them. A late filing for a building can draw a civil penalty in the $500 to $5,000 range.
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Peter Yang ran a learn how I write skill in an AI app Duet. It read 33 of his sent emails, 89 Slack messages, 47 DMs and 11 docs, then saved a writing guide as a skill that Duet now uses to draft his email replies in his own style for him to check before sending.
He connected his Gmail to an AI task that watched every new email and was only allowed to interrupt him when a message needed action or came from family, with a draft reply ready. All afternoon it alerted him three times, for a bank message, a family email he answered from its draft, and a ticket itinerary change he needed to act on.