I just released a new episode of The Slow Hunch with Matthew Prince, CEO and co-founder of Cloudflare. Since we invested in their Series C back in 2013, I've watched Matthew and his team build one of the most critical pieces of internet infrastructure—protecting and accelerating vast portions of global web traffic.

Our conversation traces Matthew's journey from his early "slow hunch" that the internet was fundamentally broken and needed fixing. We start with his law school days in 2000, when he was annoyed by email spam and registered the domain "unspam.com." That legal mindset—thinking about jurisdiction problems the internet created—would eventually collide with technical brilliance when he met his future co-founders Lee Holloway and Michelle Zatlyn.

The origin story alone is worth the listen: Matthew literally pitched his trademark protection idea at an FTC hearing, got confronted by a professor who had built the exact same technical solution, and ended up hiring one of that professor's students (Lee) who would become Cloudflare's technical co-founder.

But the real meat of our conversation is about what's happening right now. We're living through a fundamental shift in how the internet works: moving from search engines to "answer engines"—from getting a "treasure map" of links to getting direct answers. This changes everything about how the internet's business model works.

Matthew argues we're at a critical juncture. The current model where publishers depend on traffic (and the ad revenue that comes with it) is breaking down because AI systems provide answers without sending users to the original sources. We could end up with a handful of AI companies controlling their own fleets of journalists and researchers—essentially returning to a medieval patronage system. Or we could build something better.

The path Matthew envisions involves creating a fair marketplace where AI companies pay content creators based on their scale and usage, similar to how Spotify compensates musicians. Matthew shares the story of a music creator making 40 million euros annually by writing songs for unfulfilled Spotify queries—imagine that model applied to knowledge creation.

I just released a new episode of The Slow Hunch with Matthew Prince, CEO and co-founder of Cloudflare. Since we invested in their Series C back in 2013, I've watched Matthew and his team build one of the most critical pieces of internet infrastructure—protecting and accelerating vast portions of global web traffic.

Our conversation traces Matthew's journey from his early "slow hunch" that the internet was fundamentally broken and needed fixing. We start with his law school days in 2000, when he was annoyed by email spam and registered the domain "unspam.com." That legal mindset—thinking about jurisdiction problems the internet created—would eventually collide with technical brilliance when he met his future co-founders Lee Holloway and Michelle Zatlyn.

The origin story alone is worth the listen: Matthew literally pitched his trademark protection idea at an FTC hearing, got confronted by a professor who had built the exact same technical solution, and ended up hiring one of that professor's students (Lee) who would become Cloudflare's technical co-founder.

But the real meat of our conversation is about what's happening right now. We're living through a fundamental shift in how the internet works: moving from search engines to "answer engines"—from getting a "treasure map" of links to getting direct answers. This changes everything about how the internet's business model works.

Matthew argues we're at a critical juncture. The current model where publishers depend on traffic (and the ad revenue that comes with it) is breaking down because AI systems provide answers without sending users to the original sources. We could end up with a handful of AI companies controlling their own fleets of journalists and researchers—essentially returning to a medieval patronage system. Or we could build something better.

The path Matthew envisions involves creating a fair marketplace where AI companies pay content creators based on their scale and usage, similar to how Spotify compensates musicians. Matthew shares the story of a music creator making 40 million euros annually by writing songs for unfulfilled Spotify queries—imagine that model applied to knowledge creation.