Jul 24, 2026

How Two French Engineers In New York Built The Company That Monitors The Entire Cloud

Datadog CEO Olivier Pomel shares his journey, emphasizing the company's evolution from a DevOps insight to a public tech giant. He discusses the resilience required to overcome early rejections, his hands-on leadership style focused on raw customer feedback, and how Datadog is rapidly adapting to the AI revolution by prioritizing automation and faster iteration in product development and internal processes. Pomel also offers candid advice on co-founder relationships and the critical importance of moving quickly in both hiring and firing.

Jul 10, 2026

The AI-Native Startup Playbook (Ep. 1008 with Jon Krohn)

Anthropic's Founder's Playbook redefines startup building in the AI era, emphasizing that AI has removed traditional bottlenecks, making execution cheap and judgment the scarce resource. The playbook outlines four stages—Idea, MVP, Launch, and Scale—providing practical guidance on sharpening problem statements, using AI as a devil's advocate, combating agentic technical debt, achieving true product-market fit, and building defensible moats against incumbents. The overarching message: prioritize strategic sense-making over effortless building.

Jun 26, 2026

How Warp Went From YC to a $60M Series B

Warp founder & CEO Ayush Sharma discusses building an AI-native employee management platform in a competitive market, detailing how "unsexy" payroll problems became a powerful wedge and why AI fundamentally shifts enterprise software development. He explains what "AI-native" means for product architecture and company structure, the advantage it gives technical founders, and Warp's vision for "systems of intelligence" to empower customers with AI agents for complex HR workflows.

Jun 19, 2026

The Age Of The 40-Year-Old Solo Founder Is Here

Bryant Chou, co-founder of Webflow, introduces his new AI-powered platform, Ploy. This episode delves into how Ploy transcends traditional website builders by integrating analytics, CRM, and SEO to autonomously optimize marketing. Chou discusses Ploy's 'anti-slop' approach, leveraging curated data and expertise to produce high-quality web designs, and reflects on building a startup in the AI era compared to Webflow's early days. He also explores the competitive moat of purpose-built AI, the concept of 'agents as customers,' and how experienced founders can leverage AI to 'clone themselves' and achieve unprecedented speed and scale.

Jun 17, 2026

How To Pick A Startup Idea

Jon Xu, a YC General Partner, argues against the "perfect idea" trap and juggling multiple startup concepts. He advocates for founders to commit deeply to a single idea, immersing themselves in customer problems to the point of understanding their business intimately. This approach, especially vital in the AI era, involves building at the frontier of technology, verticalizing to own outcomes, and aiming for the most ambitious version of a solution, ultimately yielding invaluable insights and potential for pivot, even if the initial idea doesn't succeed.

Apr 24, 2026

How To Build A Company With AI From The Ground Up

Y Combinator Partner Diana Hu explains how to build an AI-native company where AI is the core operating system, not just a tool. She covers how to make a company queryable, the impact on team structures, and why startups have a massive edge in this new paradigm.