The discussion
The hosts are divided on the New York Times' outlook. Jason is the clear bull, pointing to two distinct strengths: the Times has already proven itself as the most successful digital news subscription business with 12 million paid subscribers, and its copyright lawsuit against OpenAI could eventually generate LLM licensing revenue that surpasses both advertising and subscriptions — potentially transforming its economic model entirely. Chamath, by contrast, is a low-conviction bear on non-financial grounds, speculating that within five years the Times will publish something so egregiously false or libelous that the resulting lawsuit could force it into a nonprofit structure and effectively end it as a going concern. The disagreement is less about the Times' current financial performance — which Jason regards as objectively strong — and more about tail-risk exposure to a reputational and legal catastrophe that Chamath sees as plausible.