Episode: Matthew Prince (Co-founder & CEO of Cloudflare)
Pub date: 2025-09-24
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In this episode of The Slow Hunch, I spoke with Matthew Prince, the co-founder and CEO of Cloudflare. Since 2010, Matthew and his team have built Cloudflare into one of the most important companies on the internet: powering and protecting vast portions of global traffic.
Our conversation explores the through-line from Matthew’s initial hunch about fixing the flaws of the early internet, to Cloudflare’s present role as a foundational infrastructure provider.
We talk about the early experiments and risks that have shaped Cloudflare’s culture, and how those small bets compounded into a truly iconic company today. Matthew shares stories from the company’s pre-IPO days, the decision to make encryption free, and how Cloudflare’s infrastructure ended up running two of the internet’s thirteen root servers. Toward the end, we dive deep into the transition from a search-driven internet to an answer-driven one, and what that means for publishers, creators, and the future business model of the web.
It was especially fun to record this one with Matthew, who I’ve known since USV’s investment in Cloudflare’s Series C back in 2013.
Hope you enjoy!
Chapters
- 00:00:00 Curiosity vs. focus; small bets culture00:02:44 Pre-IPO mock earnings calls & learning to take hard questions00:04:48 Matthew’s slow hunch00:05:54 The Unspam origin story: legal mindset meets early internet problems00:11:16 Passing trademark legislation in Utah00:13:39 Meeting Lee (via Arthur Keller)00:18:00 Lee moves to Utah; building from a basement00:20:02 From Unspam to Cloudflare00:20:25 Enter Michelle00:28:19 Realizing how critical Clouflare’s role was (the 2017 outage)00:29:07 Conducting experiments at scale: how small bets can become big lines of business00:31:44 Making encryption free00:33:26 From brittle deploys to Workers00:36:00 Cost curve obsession & why lowest cost to serve always wins00:38:00 Running 2 of the 13 internet root servers00:41:31 Pakistan Telecom story: local demand opens networks00:43:32 Principled decisions > spreadsheets00:44:40 Shift from search engines to answer engines00:48:00 Longing for a quirkier web00:52:56 Incentivizing creators to fill LLM knowledge gaps00:56:05 Designing an open, fair market (price by scale/MAU, not tokens)01:01:15 Scarcity switch flips; next-gen models hit a plateau01:04:00 Google’s role: should AI overviews fund creators?01:06:35 GPUs & researchers commoditize; content becomes the moat01:09:00 Reddit vs. NYT: the value of original/local/quirky content01:10:49 Toward a golden age of content (less rage, more knowledge)01:13:17 Counterintuitive optimism for human-made content
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