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

In this episode of The Slow Hunch, I spoke with Dan Romero and Varun Srinivasan, the co-founders of Farcaster. Farcaster is a social app and protocol that is open, programmable, and crypto-native. 

Before starting Farcaster, both Dan and Varun spent a few years at Coinbase. That experience deeply shaped their perspective on crypto infrastructure, user behavior, and what it takes to build a “sufficiently decentralized” experience at scale.

In this conversation we trace their slow hunch: the idea that social networks needed to be rebuilt from the ground up, as decentralized protocols with credible neutrality, shared state, and a design space open to builders. 

We talked about what they got wrong early on (too much focus on architecture, not enough on user acquisition), how crypto enables new interaction primitives like tipping and token-based identity, and why open programmability (not just ideology) is Farcaster’s biggest edge.

Hope you enjoy!

Chapters: 

• 00:00:00 Cold open
• 00:02:20 What makes Farcaster different
• 00:06:45 Early crypto days at Coinbase
• 00:10:30 Discovering a shared vision for decentralized protocols
• 00:16:07 Why the infrastructure is ready now
• 00:20:55 The social landscape in 2020: Twitter, Mastodon, Bluesky
• 00:23:00 Elon acquires Twitter, FTX, and the narrative shift in decentralized social
• 00:24:53 Designing for "sufficient decentralization"
• 00:29:26 Why the obsession over pure decentralization is a distraction
• 00:32:05 The Farcaster launch story - how they got their first users
• 00:34:30 Why social protocols take time to grow
• 00:36:28 Inventing new content primitives instead of choosing political sides
• 00:41:00 What crypto rails enable: Wallets, tipping, and programmable social UX
• 00:42:38 Reframing money as social interaction
• 00:43:56 Why crypto feels contrarian
• 00:45:59 Crypto as the last frontier of indie building
• 00:47:01 AI vs crypto as platforms for small creators
• 00:49:40 Hiding vs embracing crypto in UX
• 00:50:55 Dan and Varun’s evolving view on abstracting away the chain
• 00:54:00 The adjacent possible: mini-apps, embedded wallets, AI video
• 00:59:00 Using AI to surface context + trending content
• 01:00:54 What big platforms won’t do: programmable money
• 01:03:57 Crowdsourced Q&A – early Farcaster days
• 01:06:53 Why mobile UX is everything
• 01:07:00 The surprising difficulty of building other clients
• 01:08:43 Varun on shifting from text to video
• 01:13:00 Why they cut encrypted messaging
• 01:15:00 Closing thoughts

In this episode of The Slow Hunch, I spoke with Ben Leventhal, the founder and CEO of Blackbird. Ben has spent the past two decades reimagining the restaurant industry, having previously co-founded Eater and Resy. 

The throughline that connects his efforts is a strong belief that restaurants are universally loved but fundamentally broken businesses—and that there must be a better way to run what is a trillion dollar industry in the United States alone. 

We talked about what’s gone wrong with the restaurant business model, why most restaurants struggle to turn a profit despite enormous consumer love, and how each of Ben’s ventures has tried to close that gap—first with content (Eater), then with mobile (Resy), and now with crypto (Blackbird). 

Through Blackbird, Ben is using crypto rails to build a restaurant-native platform currency: one that rewards regulars, strengthens margins, and builds more intimate ties between diners and the places they love.

We recorded this conversation in my apartment in New York, just around the corner from a restaurant I paid for using Fly, Blackbird’s currency. Few founders have followed a hunch as consistently and creatively as Ben. 

Hope you enjoy!

Chapters:

• 00:00:00 Cold open: why restaurants are broken
• 00:01:10 Introducing Ben Leventhal
• 00:02:00 Ben’s slow hunch: the status quo is always wrong
• 00:05:00 Falling in love with restaurants as a kid
• 00:08:00 She Loves New York: the proto-Eater newsletter
• 00:10:30 Early blogging and New York’s indie media scene
• 00:14:00 Starting Eater with Lockhart Steele
• 00:16:00 Eater as “sports coverage” for restaurants
• 00:18:00 Why restaurateurs initially hated Eater
• 00:20:30 Scooping the New York Times
• 00:22:00 The adjacent possible and building with new tools
• 00:24:30 Leaving Eater and exploring new projects
• 00:25:50 The Resy origin story
• 00:27:30 Resy’s mobile-first wedge: outdoor seating and Notify
• 00:31:00 Selling Resy to Amex
• 00:33:00 Why Resy was restaurant-first (and OpenTable wasn’t)
• 00:38:00 The COVID reset: restaurants become brands
• 00:45:00 The idea for Blackbird takes shape
• 00:52:00 Introducing Fly: a platform currency for restaurants
• 00:56:00 How Fly helps restaurants recapture value
• 01:00:00 Restaurant regulars as shareholders
• 01:03:00 Designing Blackbird to feel like a consumer app
• 01:04:00 What’s next: AI and the future of restaurant marketing

In this episode of The Slow Hunch, I spoke with Juan Benet, the founder and CEO of Protocol Labs. Juan is best known for creating IPFS and Filecoin—two foundational technologies in the decentralized web. Through Protocol Labs, Juan wants to use decentralized protocols to unlock new ways of organizing capital, governance, and research. 

This conversation was recorded more than a decade after we first met, when USV seed funded Protocol Labs. Juan is one of the deepest thinkers I know, so naturally this conversation has a wide aperture. We touched on internet history, crypto network design, public goods funding, and the future of intelligence itself.

Hope you enjoy!

Chapters:

• 00:00 Cold open
• 00:07:39 Discovering the power of P2P tech
• 00:11:10 Decentralization versus central planning
• 00:17:44 Juan’s slow hunch
• 00:21:16 Protocol Labs as a way to plug the R&D funding gap
• 00:24:03 The genesis of IPFS and Filecoin
• 00:30:45 Layering protocols for success
• 00:33:18 New frontiers in governance
• 00:41:09 The role of public utilities
• 00:47:39 Juan’s thoughts on the future of work
• 00:52:41 Blockchains as a governance layer for AI agents
• 01:01:32 Evolving into a new species

In this episode of The Slow Hunch, I’ve pulled together some of the best moments from Season 1.

Across these conversations, what stood out was how many ‘inevitable’ ideas were, at one point, anything but.

Venture veterans Fred Wilson and Brad Burnham reflected on decades of investing, Bluesky CEO Jay Graber spoke about her vision for decentralized social, and author and NotebookLM co-creator Steven Johnson unpacked the future of networked thought.

We got a clearer view into how their slow hunches took shape — and where they’re headed next.

Hope you enjoy!

Chapters: 

• 00:00:00 Cold open 
• 00:02:53 Fraser Kelton (GP at Spark Capital, former Head of Product at OpenAI)
• 00:09:06 Dani Grant (CEO of Jam.dev)
• 00:20:02 Amir Haleem (Founder of Helium, CEO of Nova Labs)
• 00:25:10 Fred Wilson & Brad Burnham (Union Square Ventures)
• 00:30:40 Jake Heller (Co-founder & CEO of Casetext)
• 00:40:00 Steven Johnson (Author, Editorial at NotebookLM and Google Labs)
• 00:49:35 Muneeb Ali (Co-founder of Stacks, CEO at Trust Machines)
• 00:53:33 Jay Graber (CEO of Bluesky)
• 01:03:26 Zoe Weinberg (Founder, ex/ante)
• 01:09:25 Aaron Wright (Co-founder & CEO of Tribute Labs)

In this episode of the Slow Hunch, I spoke with Aaron Wright, the co-founder and CEO of Tribute Labs. 

Aaron has been exploring how to harness the collective knowledge, energy, and capital of online communities for 20 years, from his early work at Wikipedia to his current focus on decentralized autonomous organizations (DAOs) and AI agents.

Aaron believes major technological shifts lead to equally significant changes in organizational structures. He sees DAOs as the next evolution after the joint stock company that transformed capitalism centuries ago. According to him, thin layers of technology will enable coordination and collaboration at unprecedented scales - from hundreds to potentially millions of people.

In our conversation, we explored how blockchains are enabling new forms of collaboration and how embedding AI on top of these coordination layers might fundamentally change how we organize ourselves and our capital.

I've been following Aaron's work for years, and we've had the pleasure of investing in Tribute Labs at USV. Hope you enjoy!

Chapters:

• 00:00:00 Cold open
• 00:02:07 Aaron’s slow hunch
• 00:10:58 The evolution of DAOs
• 00:15:31 Aaron’s early experiences at wikipedia and ethereum
• 00:37:21 His work with OpenLaw
• 00:42:46 The rise of investment DAOs
• 00:53:03 AI and the adjacent possible
• 01:08:30 The future of AI and ownership

In this episode of the Slow Hunch, I spoke with Jay Graber, CEO of Bluesky. 

Originally conceived as an initiative within Twitter under Jack Dorsey, Bluesky was designed to transform Twitter from a closed platform to an open protocol-based network. Jay initially joined as an external researcher before being selected to lead the project, ultimately negotiating for Bluesky's independence before Elon Musk’s acquisition. 

Jay believes thoughtful systems design can reshape our online experiences. With Bluesky, she wants to prioritise user choice, portability, and the ability to vote with their feet if the platform makes changes they don't like.

This was a conversation about social media’s “adjacent possible”  - a potential shift from closed, monolithic platforms toward open, extensible systems that encourage experimentation and innovation at all levels.

Hope you enjoy!

Chapters:

• 00:00 Cold open
• 04:00 Jay’s background: from systems theory to digital rights activism 
• 08:35 Trade-offs in systems design
• 16:19 The AT Protocol (atproto)
• 17:19 Bluesky’s origin story
• 25:26 How Bluesky differs from earlier decentralized social attempts 
• 28:01 Giving users the ability to pick feeds and moderation 
• 30:16 Early days of Bluesky
• 32:50 Public launch
• 37:24 Social media’s adjacent possible 
• 46:13 Closing thoughts

In this special episode of the Slow Hunch, I sat down with Fred Wilson and Brad Burnham, founding partners of USV. 

Since founding USV in 2003, Fred and Brad have backed companies like Twitter, Etsy, Cloudflare, and Coinbase while developing an investment thesis focused on enabling new forms of value creation through open access to networks, capital, and knowledge. 

Fred and Brad bring decades of investment experience, having seen multiple tech cycles from the early internet to mobile, cloud, crypto, and now AI. What makes their partnership unique is how they've maintained their intellectual curiosity and drive to understand emerging technologies and business models, after 20+ years of working together. 

I've been lucky enough to have a front-row seat to their approach, and it was really special to have this conversation over multiple mugs of tea in my living room in New York City. 

In many ways, USV has been their collective slow hunch - an exploration of how emerging tech intersects with the world and how to be part of it.

Hope you enjoy this conversation! 

Chapters: 

• 00:00:00 Cold open
• 00:10:40 How USV was formed
• 00:17:16 Fred and Brad on their investment philosophy
• 00:24:01 Overcoming early challenges
• 00:27:43 The emergence of web2
• 00:30:59 The initial promise of social media
• 00:34:04 Investing in Twitter
• 00:39:11 The early days of Bitcoin
• 00:45:55 The risk of market consolidation in AI 
• 00:49:39 Fred and Brad reflect on their mistakes
• 00:57:18 The Impact of AI
• 01:07:23 The future of technology
• 01:09:50 What keeps them going after 30+ years