#254 Prashanth: Why Developers Still Trust Stack Overflow in the Age of AI

May 14, 2025

Prashanth Chandrasekar, CEO of Stack Overflow, delves into how the platform is evolving in the age of generative AI. He discusses Stack Overflow's partnerships with major LLM providers to enhance AI accuracy while preserving community integrity. Prashanth highlights the unique role of Stack Overflow as a foundational knowledge base that aids AI technologies. The conversation also touches on the complexities developers face with AI-generated code and the continued reliance on human expertise to tackle challenges beyond AI's current capabilities.

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ANECDOTE

Stack Overflow's Expert Knowledge Origin

Stack Overflow began in 2008 as a platform to create an authoritative tech knowledge base curated by experts.
It now hosts over 60 million Q&A pairs, serving millions globally with trustworthy guidance.

INSIGHT

Stack Overflow Powers AI Accuracy

Stack Overflow licenses its high-quality data to LLM providers to improve AI accuracy by about 30%.
Their data also helps reduce hallucinations and requires attribution in AI-generated answers to boost trust.

ADVICE

Integrate AI to Aid Developers

Incorporate AI to enhance user productivity without competing with LLM providers.
Use AI to provide features like natural language Q&A summaries linked to canonical answers.

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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