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In this episode of Eye on AI, host Craig Smith speaks with Prashanth Chandrasekar, CEO of Stack Overflow, about how one of the internet’s most trusted platforms for developers is adapting to the era of generative AI. With over 60 million human-curated Q&A pairs, Stack Overflow is now at the center of AI development — not as a competitor to large language models like ChatGPT, but as a foundational knowledge base that powers them.
Prashanth breaks down how Stack Overflow is partnering with OpenAI, Google, and other LLM providers to license its data and improve AI accuracy, while also protecting the integrity of its community. He explains the rise of OverflowAI, how Stack Overflow for Teams is fueling enterprise-grade co-pilots, and why developers still rely on expert human input when AI hits its “complexity cliff.” The conversation covers everything from hallucination problems and trust issues in AI-generated code to the monetization of developer data and the evolving interface of the web.
If you want to understand the future of developer tools, AI coding assistants, and how human knowledge will coexist with autonomous agents, this episode is a must-listen.
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(00:00) Intro
(02:31) Prashanth’s Journey from Developer to CEO
(05:18) Why Stack Overflow is Different from GitHub
(08:51) The Power of Community and Human-Curated Knowledge
(12:53) Stack Overflow’s Data Strategy for AI Training
(17:26) Why Stack Overflow Isn’t Competing with OpenAI
(20:36) How Stack Overflow Powers Enterprise AI Agents
(26:13) OverflowAI, Gemini, and the Future of Dev Workflows
(30:09) Inside Stack Overflow for Teams
(33:29) Safeguarding Quality: The Fight Against AI Slop
(38:32) Licensing, Attribution, and Protecting the Knowledge Base
(43:19) Business Strategy in the Age of Generative AI