Today, I’m talking with Prashanth Chandrasekar, who is the CEO of Stack Overflow. I last had Prashanth on the show in 2022, one month before ChatGPT launched. While the generative AI boom had tons of impact on all sorts of companies, it immediately upended everything about Stack Overflow in an existential way.
Stack Overflow, if you’re not familiar with it, is the question and answer forum for developers writing code. Before the AI explosion, it was a thriving community where developers asked for and received help with complicated programming problems. But if there’s one thing AI is good at, it’s helping developers write code — and not just write code, but develop entire working apps. On top of that, Stack Overflow’s forums themselves became flooded with AI-generated answers, bringing down the quality of the community as a whole.
You’ll hear Prashanth explain that it was clear more or less from the jump how big a deal ChatGPT was going to be, and his response was pure Decoder bait. He called a company emergency, reallocated about 10 percent of the staff to figure out solutions to the ChatGPT problem, and made some pretty huge decisions about structure and organization to navigate that change.
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Three years later, Prashanth says Stack Overflow is now very comfortable primarily as an enterprise SaaS business, which provides AI-based solutions that are tailored to different companies’ internal systems. Stack Overflow also operates a big data licensing business, selling data from its community back to all those AI companies, large and small.
That’s a pretty big pivot from being seen as the place where everyone can go to get help with their code. So I had to ask him: does Stack Overflow even attract new users anymore, in 2025, when ChatGPT can do it all for you? Prashanth said yes, of course. You’ll hear him explain that while AI can handle simple problems, for thorny, complex ones, you really want to talk to a real person. That’s where Stack Overflow still brings people together.
You’ll hear us come back to a single stat in particular: Prashanth says more than 80 percent of Stack Overflow users want to use AI or are already using AI for code-related topics, but only 29 percent of that population actually trusts AI to do useful work.
That’s a huge split, and it’s one I see all over in AI right now. AI is everywhere, in everything, and yet huge numbers of people say they hate it. We see it, in the Decoder inbox, in the comments on The Verge, and on our videos on YouTube. Everyone says they hate it — and yet numbers don’t lie about how many millions of people are using it and apparently deriving some benefit.
It’s a big contradiction and hard to unpack. But Prashanth was pretty willing to get into it with me. I think you’ll find his answers and his insight very interesting.
Okay: Prashanth Chandrasekar, CEO of Stack Overflow. Here we go.
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