Matthew Prince (Co-founder & CEO of Cloudflare)

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Sep 24, 2025

In this intriguing conversation, Matthew Prince, the co-founder and CEO of Cloudflare, shares insights from building one of the internet’s vital infrastructure companies. He recounts the pivotal moments that shaped Cloudflare's journey, including the decision to make encryption free and the company’s role in running DNS root servers. Matthew also discusses the shift from a search-driven to an answer-driven web, exploring its implications for publishers and creators. His vision suggests a hopeful future where unique content thrives in a changing digital landscape.

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ANECDOTE

How A Chance FTC Meeting Found Lee

Matthew met Lee Holloway after discovering Arthur Keller's work at an FTC event and recruiting him.
They negotiated patents, equity, and hired students, which later seeded Cloudflare's technical team.

ANECDOTE

Unspam Became Cloudflare Seed Capital

Unspam raised money and later licensed Project Honeypot data into Cloudflare in exchange for equity.
That small equity stake in Cloudflare later became highly valuable.

ADVICE

Use A Free Tier To Learn And Scale

Offer a compelling free tier to onboard many users and collect the data needed to improve products.
Use that scale to discover real problems and then build paid solutions around them.

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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 culture
00:02:44 Pre-IPO mock earnings calls & learning to take hard questions
00:04:48 Matthew’s slow hunch
00:05:54 The Unspam origin story: legal mindset meets early internet problems
00:11:16 Passing trademark legislation in Utah
00:13:39 Meeting Lee (via Arthur Keller)
00:18:00 Lee moves to Utah; building from a basement
00:20:02 From Unspam to Cloudflare
00:20:25 Enter Michelle
00:28:19 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 business
00:31:44 Making encryption free
00:33:26 From brittle deploys to Workers
00:36:00 Cost curve obsession & why lowest cost to serve always wins
00:38:00 Running 2 of the 13 internet root servers
00:41:31 Pakistan Telecom story: local demand opens networks
00:43:32 Principled decisions > spreadsheets
00:44:40 Shift from search engines to answer engines
00:48:00 Longing for a quirkier web
00:52:56 Incentivizing creators to fill LLM knowledge gaps
00:56:05 Designing an open, fair market (price by scale/MAU, not tokens)
01:01:15 Scarcity switch flips; next-gen models hit a plateau
01:04:00 Google’s role: should AI overviews fund creators?
01:06:35 GPUs & researchers commoditize; content becomes the moat
01:09:00 Reddit vs. NYT: the value of original/local/quirky content
01:10:49 Toward a golden age of content (less rage, more knowledge)
01:13:17 Counterintuitive optimism for human-made content