What PayPal Learned About AI Before AI Existed

The pitch arrives in my inbox almost every week, always some variation of the same thesis: "We're replacing our compliance team with an AI agent. The model is accurate. We think we're ready."

Every time I read it, I feel the same quiet unease. Not because AI isn't powerful — it genuinely is. But because I've watched this instinct play out before. The technology was different. The consequences were not.

Let me tell you about the summer of 2000.

PayPal Was Bleeding to Death — And Nobody Could Stop It

By June of 2000, PayPal was losing approximately $12 million every month to fraud.

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