AI Wins: real things real people did with AI
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A couple used AI to help get a $22,604 surprise ER bill waived
Jackie Davalos got a collections notice for an ER visit she never billed for. Her partner used Claude to help dispute it; the hospital later waived the whole amount.
AI used: Claude (Anthropic; plan not stated in the coverage) · Dispute work mid-2025; New York Times April 2026
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A couple used AI to help get a $22,604 surprise ER bill waived
Jackie Davalos got a collections notice for an ER visit she never billed for. Her partner used Claude to help dispute it; the hospital later waived the whole amount.
AI used: Claude (Anthropic; plan not stated in the coverage) · Dispute work mid-2025; New York Times April 2026
A tech writer built his own stand-ins for $400 a year of app subscriptions, using a $20 AI plan
How-To Geek's Dibakar Ghosh used Claude to build home-made swaps for a grammar checker, a dictation app and a time tracker. Real savings, with a few catches.
AI used: Claude (US$20/month plan), plus free open-source tools and a local AI model · October 2026
One developer, one AI model, and free look-alikes of Photoshop, Premiere and Excel
A veteran engineer used Claude to build free, open-source stand-ins for Adobe and Microsoft Office apps. Real and downloadable, but early alpha.
AI used: Claude Opus 5.5 (Anthropic) · October 2026
A 23-year-old amateur used AI to help crack a 60-year-old math problem
An amateur gave an unsolved Erdős problem to GPT-5.4 Pro. Terence Tao and Jared Duker Lichtman checked the proof and say the key idea is new.
AI used: ChatGPT Pro (GPT-5.4 Pro) · April 2026
A family says a $20 AI plan helped cut a $195,000 hospital bill to about $33,000
A grieving family used Claude to decode billing codes, flag duplicate charges and write dispute letters. Self-reported, so read it that way.
AI used: Claude (US$20/month plan); ChatGPT to double-check a letter · October 2025
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