The Slow Hunch

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.

Join Alex Komoroske, co-founder and CEO of Common Tools, who previously led projects at Google and Stripe, as he shares insights on the transformative power of emergence in technology. He discusses how individual user behaviors can lead to significant collective outcomes and the importance of data-driven decision-making. The conversation dives into the complexities of AI and its security risks, urging the need for awareness around data policies and the potential dangers of an AI monoculture. Alex's perspective on the evolution of collaborative platforms like Wikipedia is equally captivating!

In this discussion, MC Lader, President and COO of Uniswap Labs, and Marvin Ammori, Chief Legal Officer, dive into the intersection of technology and financial empowerment. They reflect on their experiences in building Uniswap and advocate for decentralized finance while addressing regulatory challenges. The duo draws parallels between the net neutrality movements and today’s crypto landscape, emphasizing the transformative potential of stablecoins and their vision for a future where open finance reshapes global economic access.

Dan Romero and Varun Srinivasan, co-founders of Farcaster, a decentralized social network protocol, share their journey from Coinbase to reshaping social media. They discuss the need for truly decentralized platforms, emphasizing user engagement over mere architecture. The duo explores innovative features like crypto-enabled interactions and the importance of open programmability. They also reflect on the evolution of decentralized networks, comparing them to giants like Twitter and the challenges of user adoption in a rapidly changing landscape.

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 broken00:01:10 Introducing Ben Leventhal00:02:00 Ben’s slow hunch: the status quo is always wrong00:05:00 Falling in love with restaurants as a kid00:08:00 She Loves New York: the proto-Eater newsletter00:10:30 Early blogging and New York’s indie media scene00:14:00 Starting Eater with Lockhart Steele00:16:00 Eater as “sports coverage” for restaurants00:18:00 Why restaurateurs initially hated Eater00:20:30 Scooping the New York Times00:22:00 The adjacent possible and building with new tools00:24:30 Leaving Eater and exploring new projects00:25:50 The Resy origin story00:27:30 Resy’s mobile-first wedge: outdoor seating and Notify00:31:00 Selling Resy to Amex00:33:00 Why Resy was restaurant-first (and OpenTable wasn’t)00:38:00 The COVID reset: restaurants become brands00:45:00 The idea for Blackbird takes shape00:52:00 Introducing Fly: a platform currency for restaurants00:56:00 How Fly helps restaurants recapture value01:00:00 Restaurant regulars as shareholders01:03:00 Designing Blackbird to feel like a consumer app01:04:00 What’s next: AI and the future of restaurant marketing

Juan Benet, the founder and CEO of Protocol Labs, is a trailblazer in decentralized web technology, creating IPFS and Filecoin. He shares insights on the evolution of decentralized systems and their potential to reshape governance and finance. Juan discusses the challenges of funding innovative research and the necessity of bridging gaps in technology development. He also explores the intersection of AI and crypto, pondering future governance models and the transformative role these technologies might play in society. Prepare to rethink the future!

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)

Aaron Wright, co-founder and CEO of Tribute Labs, is a pioneer in harnessing online communities and exploring DAOs for over two decades. In a captivating discussion, he outlines how major tech shifts redefine organizational structures and the rise of decentralized autonomous organizations as the evolution of capitalism. The conversation delves into the potential of blockchain and AI to transform collaboration and ownership models, enabling coordination among millions. Wright also shares insights from his journey, highlighting the merging of law with innovative technology.

Jay Graber, CEO of Bluesky, previously a digital rights activist, shares insights on decentralization and its transformative potential for social media. She discusses Bluesky's origin story, emphasizes user choice, and highlights the significance of protocols that empower users. Jay delves into the trade-offs in systems design and how Bluesky aims to create an open, extensible platform, offering flexibility and innovation when users don't like the changes. Their vision challenges traditional social media, advocating for community-driven and customizable experiences.

Fred Wilson and Brad Burnham, founding partners at Union Square Ventures, share their journey through tech investment since 2003. They discuss their unique investment thesis focused on open networks and the evolution of their approach amid different tech cycles. The duo reflects on missed opportunities, like rejecting Airbnb, and the early promise of Bitcoin. They also explore the implications of AI and the tension between decentralization and market consolidation, all while maintaining a commitment to intellectual curiosity.