Cloudflare’s CEO wants to save the web from AI’s oligarchs. Here’s why his plan isn’t crazy.

Cloudflares’s Matthew Prince spent 90 minutes with me a few weeks back explaining how he’s going to convince Google and the rest of the AI oligarchs to do something astonishing: Start paying publishers to crawl their websites. Google’s been doing that for free since it was founded. The AI chatbot revolution no longer makes that possible if the web is to survive. I think he has the leverage with pay-per-crawl to pull it off. About 20 percent of websites and 80 percent of AI companies use Clouflare for security and traffic management. That’s maybe not enough leverage to fix the problem on his own. But it’s certainly enough to cause a lot of trouble. Going to be fun to watch. That’s the latest from Crazy Stupid Tech. https://crazystupidtech.com/2025/08/30/cloudflares-ceo-wants-to-save-the-web-from-ais-oligarchs-heres-why-his-plan-isnt-crazy/