Today, I’m talking with Matthew Prince, who is CEO of Cloudflare. This episode is part of a two-part series on the future of business.
What happened
This is still a developing thread, so the useful part is knowing which source signals are hardening and which ones still need caution. In software, the upgrades worth caring about are the ones that make workflows cleaner, reduce mistakes, and remove the need for extra tools.
Where the sources line up
Matthew last joined us on the show about two and a half years ago, at what we thought then was a wild pivot point for the internet — and now it turns out things are even wilder because of AI, and Matthew and Cloudflare are right at the center of it. In software, the upgrades worth caring about are the ones that make workflows cleaner, reduce mistakes, and remove the need for extra tools. The people who feel the value first are often operators, editors, creators, and teams stitching multiple apps into one daily workflow.
Practical impact for readers
Cloudflare found in June that bots made up more than half of internet traffic. That number just keeps going up as more and more AI companies scrape more and more of the web, and now as more and more AI agents try and do things for people on the web. Cloudflare sits between websites and all those agents, and allows website owners some level of control: Owners can block all those AI tools, allow them, or, as you’ll hear, only allow those that might pay money for access.
Who should pay attention now
So Matthew and I talked about how to control all these bots, what kind of mess they’re making of the web, and what kinds of information might be valuable in the future as some of the payment schemes come into focus. You’ll hear me ask pretty directly if some of the outcomes he’s describing are actually good — Matthew is a thoughtful guy, and his answer is something I’m still thinking about well after we had this conversation.
What is still unclear
AI is also upending everything inside of Cloudflare. Earlier this year, the company laid off more than a thousand people — 20 percent of the company — and then Matthew wrote an op-ed about that decision that ran in the Wall Street Journal under the headline, “How I choose which Cloudflare employees to replace with AI. ” That’s pure Decoder bait in every single dimension: AI, big controversial decisions, and org charts, all in one.
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