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: 47:03
The Music Man was a 1957 Broadway show written by Meredith Willson, a musician from the small Iowa town of Mason City. The popular play (and later movie) featured a con man called Harold Hill who ripped off the naive peo…

Duration: 54:43
Few biographers can claim to know what it feels like to be Thomas Jefferson more than the Charlottesville-based historian Andrew Burstein. The author of many books about Jefferson, Burstein’s latest, Being Thomas Jeffers…

Duration: 39:13
There was a time in the mid 20th century, the literary historian Gayle Feldman reminds us, when the book business was cool. Back then, New York publishing resembled Silicon Valley tech and the Mark Zuckerberg of his day…

Duration: 47:31
Trump’s Gazan dream is to overlay the complex human history with his own narcissistic real-estate fantasy. But for Maia Carter Hallward, co-author of a new contemporary history of Gaza, this once vibrant Mediterranean en…

Duration: 45:53
The great John Maynard Keynes explained it a century ago. In his 1930 essay, "Economic Possibilities for our Grandchildren," Keynes predicted that the future would be defined by economic abundance rather than scarcity. B…

Duration: 31:58
WTF will happen in 2026? Over the last week, we’ve been running a series of interviews about the promise and peril of the new year. And in this new weekly magazine-style KEEN ON AMERICA show, we feature highlights of con…

Duration: 45:18
If Darwin’s evolutionary theories couldn’t kill America’s faith in God, then what could? That’s the message in Daniel K. William’s new book, The Search for a Rational Faith. Americans, Williams argues, have always sought…

Duration: 55:15
Happy New Year everyone! As the final show of 2025 and first for 2026, we turned the tables and had me interviewed by the formidable David Masciotra. As you will see, my reading of 2025 is more optimistic than many of my…

Logo
Select station
VOL