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

In this episode of The Slow Hunch, I spoke with Alex Komoroske, the co-founder and CEO of Common Tools. Alex has spent his career thinking about how individual incentives can add up to significant collective outcomes.

Before starting Common Tools, he spent more than a decade at Google leading product management for the Chrome web platform, ambient computing, AR, and Search, and later served as Head of Corporate Strategy at Stripe.

We traced his slow (emergent) hunch from an early fascination with Wikipedia, through his years building internet-scale systems at Google, to his current work rethinking how AI is architected.

A big part of our conversation centered on emergence: why the most durable systems grow from the bottom up, and what that means for product design, org culture, and the future of technology - especially AI.

We also spoke about the hidden security risks in today’s AI ecosystem: why “chat” may not be the defining paradigm for complex work, how fusing data to apps risks locking us into an AI monoculture, and why policies should travel with data if we want healthier emergent effects.

It’s always fun catching up with Alex. Hope you enjoy!

Chapters:

• 00:00:00 Cold open: the inevitability of transformers
• 00:03:32 Why emergence is so powerful
• 00:08:49 Alex’s early influences
• 00:10:35 The emergent dynamics of Wikipedia
• 00:13:15 The role of “folksonomies”
• 00:17:33 Concave systems vs convex systems
• 00:20:41 Alex’s time at Google
• 00:24:27 How small signals scale
• 00:28:58 Evolutionary algorithms in AI
• 00:30:52 Understanding data bias and rethinking how AI is architected
• 00:41:02 The same-origin trap and the limits of app-centric software
• 00:47:42 The future of contextual apps
• 00:49:03 Aggregators and the tyranny of the marginal user
• 00:52:08 Why prompt injection is so dangerous
• 00:55:23 The inherent security risks of MCP and vibe coding
• 00:59:32 A new constitution for AI: policies attached to data
• 01:03:17 The promise of confidential compute
• 01:11:00 Why Alex is optimistic about AI's Future

In this episode of The Slow Hunch, I spoke with MC Lader and Marvin Ammori, who spent four years together helping build Uniswap into one of the most important companies in decentralized finance. MC was President and COO; Marvin served as Chief Legal Officer after a long career as one of the internet’s leading policy lawyers.

We traced their shared slow hunch that technology can shift power: first through the open internet, and later through open financial systems.

We also spoke about the parallels between the net neutrality battles of the 2000s and the present-day struggle over how crypto is regulated, the challenge of building in the face of policy headwinds, and why stablecoins, programmable markets, and open protocols are placed to be the next rails for global finance.

This was a fun conversation, recorded at a moment when the policy climate for crypto is starting to thaw.

Hope you enjoy!

Chapters:

• 00:00:00 Cold open - policy headwinds under Gary Gensler
• 00:05:50 Their shared slow hunch: technology as a force for redistributing power
• 00:14:47 Winning the net neutrality fight
• 00:18:36 First encounters with Bitcoin
• 00:21:14 Parallels between the open internet and DeF
• 00:22:58 Spotting early policy threats and forming the DeFi Education Fund
• 00:23:34 Marvin recruits MC to Uniswap Labs
• 00:29:27 Scaling Uniswap from a tiny team to a full-stack protocol
• 00:34:36 Navigating growth amid SEC opposition
• 00:39:11 Gary Gensler’s impact on US crypto entrepreneurship
• 00:40:45 Stablecoins as the “lily pad” for mainstream adoption
• 00:43:20 Shifting perceptions on Wall Street
• 00:46:12 What’s next: stablecoins, tokenized markets, and on-chain identity
• 00:47:00 Building open, permissionless financial infrastructure
• 00:51:52 Potential risks: fraud, systemic stability, surveillance
• 00:55:45 Stablecoins vs. the fragility of traditional banks
• 00:57:53 Privacy, regulation, and zero-knowledge proofs
• 01:00:00 From DeFi to AllFi: what moves on-chain first?
• 01:04:11 Building for consumers versus institutions
• 01:06:03 Making money feel more human
• 01:08:49 Access to capital as a pillar of opportunity