Why Today's AI Boom Is No Dot-Com Bubble


Author: Andrew Keen January 21, 2026 Duration: 29:26
Podcast episode
Why Today's AI Boom Is No Dot-Com Bubble

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.

Keen On America is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit keenon.substack.com/subscribe

More episodes

Duration: 31:50
EPISODE 1576: In this KEEN ON show, Andrew talks to Sonali Kolhatkar, author of RISING UP, about the power of narrative in pursuing racial justice in AmericaSonali Kolhatkar is the host and creator of Rising Up with Sona…

Duration: 29:22
EPISODE 1575: In this regular weekly show with THAT WAS THE WEEK newsletter author Keith Teare, Andrew and Keith discuss an astonishing week in tech when Apple reached a three trillion dollar valuation and AI ate the int…

Duration: 30:42
EPISODE 1573: In this KEEN ON show, Andrew talks to Peace Adzo Medie, author of NIGHTBLOOM, about how to get beyond the shame of sexual violence in AfricaPeace Adzo Medie is a scholar and writer. She is Senior Lecturer i…

Duration: 29:26
EPISODE 1572: In this KEEN ON show, Andrew talks to Patrick Dean, the author of NATURE'S MESSENGER, about Mark Catesby, America's First Great NaturalistPatrick Dean writes on the outdoors and the environment. He has work…

Duration: 29:41
EPISODE 1566: In this KEEN ON show, Andrew talks to Dan Schreiber, the author of THE THEORY OF EVERYTHING ELSE, about alien abductions, the importance of having celebrity hairdresser parents and the exorcism of Ringo Sta…

Logo
Select station
VOL