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Software and Tech stories from an Insider - iDiallo.com

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Failing after Success
Ibrahim Diallo · 2026-08-10 · via Software and Tech stories from an Insider - iDiallo.com

What are you supposed to do after you've created the most successful product? Not just successful, but the most useful. In an ideal world, you would sail into the sunset and enjoy your riches. In this real world, you have to come up with another, even more successful product, or you're a failure. That's why it feels like Stack Overflow has failed.

I remember being in the middle of debugging my code when I copied an error and pasted it into Google. Right there in the search results, below the clearly marked sponsored link, was a link to Stack Overflow, where a user had previously faced the exact issue I was facing. I clicked on it and got "Error 503 Service Unavailable."

Two seconds later, I was on Reddit, checking if SO was down for everyone else. Then Hacker News. The memes started flowing shortly after. Developers were touching grass for the first time in years. Productivity was down 100%. If there were any way to measure the success of a company, that would be it.

Stack Overflow went from receiving hundreds of thousands of programming questions a day to less than a thousand today.

Stack Overflow never positioned itself as just another Q&A forum. It wasn't ExpertsExchange. The whole point was that it would be a place to find answers first, then ask questions if you couldn't find what you needed.

To me, it means mission accomplished. We've documented all the ways software could fail, and it became a helpful resource for everyone. That's a successful product, and the founders sailed into the sunset. Jeff is out there making the world a better place.

But in our business-driven world, what's the next successful product? They failed to come up with one. Yet, given their founding principles, I think Stack Overflow should have been the perfect candidate to build an AI coding assistant.

Why Cursor, Delve, or even Copilot, when you have all the world's programming Q&A at your disposal? And a permissive license on top of that. Imagine an IDE where you could contribute back to the pool. You face a challenge, you use the LLM to help resolve the problem, and you contribute your final solution back to the collective community memory.

I don't know about you, but I was a big fan of the badges you get on SO. I even bragged about them on my resume. Joel promised me an "I Met Spolsky" badge, but I think he may have forgotten about it. One of the reasons people contributed to SO was for recognition, the thank-yous, and its competitive nature. Imagine an LLM that helps users and gives credit to those who contributed to the solution.

Ibrahim and Joel Spolsky

Stack Overflow isn't dead as a business, so I don't think it's too late for them to develop a new product. Currently they have an AI assist button, tucked in a sidebar, an AI benchmark tool, and an MCP server for some reason. I imagine these aren't their most prominent features. You have to deliberately look for them.

Stack Overflow is the perfect company to create a developer-centric IDE that can leverage all that Q&A data to improve developers' workflows.

...this almost sounds like a pitch.