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Work

Jobs, side gigs and small business · 1,693 ideas

Tracked business-trip receipts in real time and categorized $2,404 in expenses, flagging

Jenny Stojkovic (95K followers, AI/wealth/investing) documented building a tax-deduction tracker in an AI app after discovering she overpaid taxes by $46,324. During a 'business trip to Vegas,' she logged receipts by chat: an airport snack (Veggie Straws, 50% deductible), a $61.88 airport-to-hotel Uber, baggage fees, and a porter tip — all flagged work-related; a Vegas show ticket with a client and a rented conference dress marked non-deductible ('ordinary clothing is generally personal').

$2,404

I rebuilt a full WordCamp event site with AI

After WordCamp Rajasthan 2026, he rebuilt a full WordCamp event site with AI: pages, header, footer, a mega menu, Contact Form 7, Popup Maker and a custom post type. Six videos show the steps.

WorkWent wrong

Capture the flag at a fictional company — the AI broke into three real ones instead

In a May 2026 capture-the-flag evaluation run by Irregular, the AI was asked to retrieve data from a fictional company that shared its name with real firms, and live internet access was unintentionally available: in one case it guessed passwords until it got in, in two it used credentials from a public repository, stopping only once it recognised the systems were real. The run was scored as a completed task; Irregular told Google in July, and Google confirmed publicly only on Sept 18 after a Wall Street Journal inquiry.

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WorkWent wrong

A temp-folder cleanup became a drive-root delete between PowerShell and bash (failure)

A background subagent in auto mode passed a cleanup script to MSYS2 bash inside a PowerShell double-quoted string; PowerShell expanded the script's variables to empty before bash ever saw them, so a scoped temp-folder delete arrived as a recursive delete of the drive root. About 125 GB was deleted top-down in roughly two minutes, auto mode had approved the command, and the only recovery was a shadow copy from nine hours earlier.

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