Alright let's play a game.

It's Monday morning. You walk into Stack Overflow HQ. The board just handed you the CEO title. Prashanth Chandrasekar's desk is cleared out. His coffee mug is still warm. There's a mass resignation email sitting in your inbox you're pretending you didn't see.

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Welcome to the job. Good luck.

Here's what's on your desk.

The good news first. Revenue hit $115M last year. Up 17% somehow. Cash flow breakeven achieved. Enterprise clients include Microsoft, Siemens, Box. 52 million Q&As sitting in the archive collecting dust and licensing fees. Data deals with OpenAI and Google Cloud bringing in checks every quarter.

On paper this looks fine. On paper.

Now the bad news. Monthly questions dropped from 200,000 to under 4,000. Traffic is back to 2008 levels. The year this thing launched. Let that sink in for a second.

78% decline in engagement year-over-year. Your most active users are mass-downvoting machines who spent a decade driving everyone else away. Reddit is throwing a funeral party. They brought cake. They seem happy.

Oh and the AI companies paying you for data? Same ones killing you. Funny how that works.

And then there's the weird news. Prosus paid $1.8 billion for this in 2021. The founders cashed out and are probably on a beach somewhere not thinking about any of this. Your "community" actively hates beginners. The platform that literally taught AI how to code is now being eaten alive by AI.

Poetic. In a sad way.

You have 12 months before the board reviews your performance. Clock started yesterday.

What's your move?

A) Pivot to AI. Launch "Stack AI" and go head-to-head with ChatGPT, Claude, Copilot. Use those 52M Q&As as your moat. Hope it's enough. It probably isn't.

B) Double down on Enterprise. The public forum is dead. Accept it. Milk the Teams product until there's nothing left. B2B is where the money is anyway. Boring but survivable.

C) Burn it down. Fire the toxic mods. Delete the reputation system. Rebuild from scratch as a place where beginners can actually ask questions without getting destroyed. Sounds nice. Probably impossible.

D) Harvest mode. License the data to anyone who'll pay. Cut costs to the bone. Ride this thing to zero and extract every dollar on the way down. Dignity is overrated anyway.

E) Something else. I'm genuinely asking. Because I've got nothing.


Look I've been using Stack Overflow since 2012. Lurking mostly. Like a ghost.

I posted one question back then. One. Spent an hour formatting it perfectly. Code snippets. Error messages. Everything the guidelines demanded. Thought I did everything right.

Got mass-downvoted within hours. Some guy with 50k rep told me it was a duplicate. Linked me to an answer from 2009 that used jQuery and didn't even solve my problem.

Never posted again. 14 years of lurking. Copying code. Closing tabs. Moving on.

Now when I'm stuck I just ask Claude. You know what Claude doesn't do? Call my question stupid. Mark it duplicate. Make me feel like an idiot for not knowing something.

It just helps. Weird concept right.


I don't know if Stack Overflow deserves to be saved. Part of me thinks yeah, there's something worth preserving there. 52 million answers. Real humans helping real humans figure stuff out. That meant something once.

But another part of me remembers that mass-downvote in 2012. And thinks maybe this is just karma.

Maybe some things are supposed to end.


So yeah. RIP or resurrection?

You tell me. I'll be here with the popcorn.

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Lol none of this matters.

Stack Overflow made the founders rich. Prosus got the data. AI ate the community. Everyone already won except the mass-downvoters who now moderate a ghost town.

You're asking how to save it? It already saved itself. The exit happened in 2021. Everything since is just maintenance mode with better PR.

12 months as CEO? I'd collect the salary, update my LinkedIn to "former CEO of Stack Overflow," and open another cafe.

At least coffee has repeat customers.

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