Episode Details

Every conversation your people are having with an AI right now is a business record — discoverable in a lawsuit, usually not privileged, and in most companies quietly set to auto-delete until the moment that becomes illegal. A Delaware court this spring removed a CEO and reinstated his predecessor over a $250 million earnout, and the decisive evidence was the CEO's own ChatGPT logs — including ones he had deleted. OpenAI is fighting a sanctions motion for allegedly destroying billions of ChatGPT conversations after a court told it to preserve them. And a federal judge ruled that a defendant's chats with a consumer AI were not privileged, because the AI is not a lawyer.

Stephen Forte on what this teaches every CEO, the records-retention rules to set this quarter (with real numbers by industry), and the single best place to do genuinely confidential AI work: an open-weight model running on hardware you own, where there is no vendor log to subpoena.