Few people experienced the Dot-Com bubble with more vertiginous intensity than Bill Gross, the Pasadena-based founder of Idealab and many many other internet startups over the last 30 years. So when I sat down with Gross at DLD, I couldn’t resist opening with the boom/bubble gambit. How, I asked him, does today’s AI hysteria compare with the Web 1.0 madness of the Nineties? While Gross - whose current ProRata.ai play is focused on protecting creativity in the age of generative AI - doesn’t believe that today’s boom is akin to the Dot-Com bubble, there are similarities. We are at what Gross calls a “Napster moment” in terms of making the big LLMs accountable for all the content they are illegally crawling (ie: stealing). And to get beyond this moment, he says, everyone from Google and OpenAI to Perplexity and Anthropic, needs to move to a “Spotify model” that fairly shares revenue with the human creators of knowledge.

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