
Prashanth Chandrasekar
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Aug 14, 2026
Ep 107: Prashanth Chandrasekar: Community and the AI Pivot
8:43
14:06

Vasant DharHOST
So what's this other part of your business that you were tasked with developing? What was the thinking and what was the value proposition there?
8:53
So the enterprise business of Stack Overflow, it's all about, because of this problem of having shared knowledge that everybody benefits from, where you're not really asking the same questions over and over again, and you have this kind of shared institutional memory, is a really big need inside companies.
9:10
Companies have employees, they come in and out, they join companies, they leave companies, they get fired, all sorts of things happen.
9:17
But the knowledge that is being sort of produced or created on a daily basis through interactions and questions and answers are all effectively going into the wind, effectively.

Vasant DharHOST
Why do people contribute like this? What motivates people like John and other power users like that? Is it altruism? Is it ego? Is it a desire to help people like all of the above? What is it that motivates these people to spend so much of their time and effort contributing towards helping other people?
Prashanth Chandrasekar, Stack Overflow: What Comes After Coding?
7:08

Tom AllenHOST
What fundamentally has changed for Stack Overflow with the introduction of generative AI more widely and for enterprise scale?
7:16
And the biggest shift for us is that, you know, we've historically been known as this amazing public platform where 100 million people came to the site and shared knowledge with each other on all things technology.
7:28
When they were writing code, they had an issue, they posted it, somebody else answered it.
7:32
And all that knowledge accrued in a very accurate, trustworthy way for over 15 years.
7 MINS LATER
Live from re:Invent…it’s Stack Overflow!
R
15:20Ryan DonovanHOST
What do you think of the sort of like future of evals and the growing importance?
15:25
I think overall, I think having guardrails is to promote trust within companies, as we've talked, as I mentioned previously, on the scaling of these models inside enterprises, especially as we adopt them responsibly and so on.
15:39
And so I generally think it's the right moment in time to talk about that, because if you talk to, you know, we have a lot of enterprise customers.
15:46
And when we describe or when we discuss with them, you know, their issues and we ask them about their problems, a lot of it comes down to, hey, we're trying a whole bunch of AI agents and assistants and experiments and POVs, but they are constrained for various reasons, mostly people reasons and data reasons and infrastructure sort of data infrastructure sort of reasons, unable to really understand expand them in a very large way across the company.
16:16
Point number two is even if they have expanded it and they've given kind of open access to a lot of people to go use these things, even with maybe throwing, let's say, caution to the wind a little bit, they're not seeing the ROI yet.
16:28
And I think then, I think it's a little bit of a confounding topic because I think 2026 will probably be like the year of rationalization around, okay, why are we spending all this money as enterprises and what are we getting for it? And so there's that pressure in the system clearly.
7 MINS LATER
Stack Overflow CEO on Dev Tools in the AI Era
15:08
5:38
A couple of years ago, when the chat GPT moment happened in November of 2022, I think pretty much the entire world had to think about or rethink how they thought about their business models.
5:49
I think especially for media companies and content companies and, you know, knowledge communities, if you will, companies like us.
5:59
Now, we had to think through, you know, what are the implications? And over time, it became pretty clear, like, I think the general nature of the internet was changing because, you know, previously people would go, you know, to a Google search engine, ask a question, land on a content site.
9 MINS LATER
Sunil RajgopalHOST
So what is the long-term vision on that and how does it reshape your identity beyond a public Q&A site?
Junky data is like an out-of-tune guitar—it prevents AI harmony
13:09
Your point absolutely is spot on in that we see a lot of folks looking for the ability to sort of be really freed in their organization to go faster.
13:21
And I think when we talked to a lot of companies, recently I was in a room with all the key leaders at all the banks, effectively.
8 MINS LATER
B
21:58Ben PopperHOST
And so it's interesting to me, I think the emergence of these Gen I systems has almost to me clarified the purpose and the utility of Stack Overflow, which is how do you create a knowledge artifact using the wisdom of the crowd that everyone can trust and adapt and improve on over time? But Prashant, do you want to talk a little bit about Answers Are Not Knowledge and kind of our perspective on knowledge as a service?

