AI-Curious with Jeff Wilser
Every week, Jeff Wilser sits down with the people building, breaking, and reckoning with AI — from the CEO of Upwork to the pioneer who coined "AGI" to an AI social network where bots wrote manifestos and had existential crises. Wilser is the author of eight books, AI keynote speaker, and the kind of interviewer who'd rather find the story no one's telling than rehash the headline everyone's read. Named by Inc. Magazine as one of the best ways to get AI-savvy. Included in UC Berkeley's data science curriculum.
AI-Curious with Jeff Wilser
AI Broke the Web’s Social Contract, w/ Tony Stubblebine, CEO of Medium
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What happens when AI can “read the whole internet” but the internet stops volunteering its best work?
In this episode of AI-Curious, we talk with Tony Stubblebine, CEO of Medium, about what he calls AI’s “broken social contract” with the web, and why the next era may be less about a “dead internet” and more about a dead public internet. We unpack the incentives that made the open web thrive, how AI search summaries change the traffic bargain, and what a realistic path forward could look like for publishers, platforms, and writers.
Key topics we cover:
-Why generative AI broke the web’s old value exchange, and what “social contract” means in practical terms (00:03:24)
-Tony’s “three Cs” framework for a healthier AI ecosystem: consent, credit, compensation (00:05:13)
-The publisher response spectrum: blocking crawlers, fighting spam/slop, and what happens if collaboration fails (00:04:25)
-The shift from public publishing to private communities (Discords, group chats, newsletters) and what drives that retreat (00:07:06)
-How AI search summaries can cut the incentive to publish publicly by reducing click-through and traffic (00:08:21)
-Why AI systems still depend on human source material, and what happens when the best content moves behind “closed doors” (00:09:27)
-Cloudflare’s role in the escalating crawler arms race, including large-scale blocking and other countermeasures (00:16:48)
-A proposed solution: an internet-wide licensing standard instead of one-off deals, including the Really Simple Licensing (RSL) approach (00:18:07)
-What “paying creators” could look like in practice, including opt-in/opt-out controls and better transparency for writers (00:19:33)
-“Dead internet theory” vs. the more plausible outcome: a dead public internet, and why Tony is cautiously optimistic about a new equilibrium (00:23:06)
-The “second wave” of AI: moving from replacement to augmentation, and how Medium is thinking about AI tools that support flow state rather than write for you (00:26:03)
-Why AI detectors don’t solve the problem, and why Medium focuses on quality and reader value as the enforceable standard (00:34:04)
-Advice for writers: the difference between the creator economy and the “expert economy,” and what’s likely to be more sustainable (00:38:43)
-Tony’s prediction: “trust but verify” becomes the balance point, and the web finds an equilibrium because AI can’t function without public sources (00:43:27)
Guest
Tony Stubblebine is the CEO of Medium and a leading voice on the evolving relationship between generative AI and the open web.
Mentioned in this conversation
Medium’s framework: Consent, Credit, Compensation
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