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.
Playback speed
×
Share post
Share post at current time
Share from 0:00
0:00
/
0:00
Transcript
Why Today's AI Boom Is No Dot-Com Bubble
Episode 2779: Bill Gross on Napster Moments and Spotify Business Models
Jan 21, 2026
Keen On America
Nobody asks sharper or more impertinent questions than Andrew Keen. In KEEN ON, Andrew cross-examines the world’s smartest people on politics, economics, history, the environment, and tech. If you want to make sense of our complex world, check out the daily questions and the answers on KEEN ON.
Named as one of the "100 most connected men" by GQ magazine, Andrew Keen is amongst the world's best-known technology and politics broadcasters and commentators. In addition to presenting KEEN ON, he is the host of the long-running show How To Fix Democracy and the author of four critically acclaimed books about the future, including the international bestselling CULT OF THE AMATEUR.
Keen On is free to listen to and will remain so. If you want to stay up-to-date on new episodes and support the show please subscribe to Andrew Keen’s Substack. Paid subscribers will soon be able to access exclusive content from our new series Keen On America.
Nobody asks sharper or more impertinent questions than Andrew Keen. In KEEN ON, Andrew cross-examines the world’s smartest people on politics, economics, history, the environment, and tech. If you want to make sense of our complex world, check out the daily questions and the answers on KEEN ON.
Named as one of the "100 most connected men" by GQ magazine, Andrew Keen is amongst the world's best-known technology and politics broadcasters and commentators. In addition to presenting KEEN ON, he is the host of the long-running show How To Fix Democracy and the author of four critically acclaimed books about the future, including the international bestselling CULT OF THE AMATEUR.
Keen On is free to listen to and will remain so. If you want to stay up-to-date on new episodes and support the show please subscribe to Andrew Keen’s Substack. Paid subscribers will soon be able to access exclusive content from our new series Keen On America. Listen on
Substack App
Apple Podcasts
Spotify
YouTube Music
YouTube
Overcast
Pocket Casts
RSS Feed
Recent Episodes













