Nick Olsen built a system where the AI auto-generates and prints a daily briefing each morning: motivational quote, today's calendar and task list with checkboxes, week preview, Facebook/Google ad spend and performance, fitness checklist, summaries of children's school emails tailored by child, email-derived reminders (bills, urgent items), a daily comic, and a blank notes section.
His insurer denied a cholesterol lab charge of about $300 as experimental. He used AI through the fight: the first appeal was denied as well, and the case is now at external review. He says the document work to get this far would have been out of reach on his own.
$300one time
This only partly worked. Worth knowing before you try it.
Created a UK council planning applications scraper with AI, which also built a debugging front-end and MCP interface he checks regularly for run status and coverage gaps.
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.
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.
Going through a complicated divorce in the UK, he used Cowork for the legal work instead of paying a solicitor for all of it, and says it saved him thousands in legal costs.
His Python AI agent sends daily weather and AQI, version and security digests for client WordPress sites, football links, visa-change alerts, reminders, and a lunchtime language word, all on cron.
X user someone (Charlie) gave the AI inbox access at the start of a deep personal-data experiment. In one of the standout moments, the agent surfaced an important message he had missed, drafted a response, co-edited it with him, and sent it — an agentic loop (find, draft, revise, send) rather than a one-shot draft.
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.