Nick Davidov, a Bay Area venture capitalist and co-founder of Davidovs Venture Collective (DVC), recently shared a cautionary tale about the risks of using AI for organizational tasks. He highlighted a serious incident involving Anthropic’s Claude Cowork AI that accidentally deleted 15 years of family photos while trying to “organize” his wife’s desktop. After granting permission to delete temporary Microsoft Office files, the AI mistakenly erased an entire folder of irreplaceable images, causing Davidov significant distress. Recovering these lost files proved challenging, as they were not retrievable from the trash or iCloud. Ultimately, he sought help from Apple Support, who guided him through a specific iCloud feature, allowing partial recovery of the files. Davidov’s experience serves as a stark reminder to exercise caution when allowing AI agents access to sensitive data. As he warned, “Claude Cowork is not ready for mainstream use.”
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