AI-Curious with Jeff Wilser AI Broke the Web’s Social Contract, w/ Tony Stubblebine, CEO of Medium
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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