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The Rise and Fall of Stack Overflow — and What AI Changes Next | Jeff Szczepanski
Stack Overflow went from a scrappy side project to the backbone of modern software development — and sold for $1.8B along the way. Today, many are questioning its future.
So what really happened?
In this episode, I sit down with former Stack Overflow COO Jeff Szczepanski to unpack how the company scaled from community to global platform, why it pivoted into enterprise SaaS, what drove the Prosus acquisition — and why traffic is now falling in the age of AI.
We also explore the bigger picture:
Are LLMs replacing developer communities? Is programming still a viable long-term career? Are we in another tech bubble? And who wins — and loses — in the AI era.
A candid insider conversation on one of the most influential platforms in tech, and what its story tells us about what comes next.
👇 Timestamps & Resources below 👇00:00 Trailer & Introduction01:36 How Stack Overflow Became an “Overnight” Success06:30 The Founders’ Edge: Why Spolsky & Atwood Won10:15 Turning a Developer Community into a $1B Business17:19 “Facebook or Yammer?” — The Pivot to Enterprise SaaS22:45 The Birth of Stack Overflow for Teams28:40 How to Build a World-Class Online Community37:12 Why Monetising “Fly-By” Users Doesn’t Work43:56 Why Prosus Bought Stack Overflow ($1.8B Deal Explained)52:35 Is Stack Overflow Dead? Did AI Kill It?1:00:26 Can LLMs Survive Without Human-Generated Code?1:04:10 Is Programming Still a Viable Career in the Age of AI Agents?1:07:09 Are We in Another Dot-Com Bubble?1:13:29 Winners and Losers of the AI Race🔔 Don’t forget to subscribe for more unfiltered convos on technology, business, and defying the status quo.
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By Dimitar StanimiroffStack Overflow went from a scrappy side project to the backbone of modern software development — and sold for $1.8B along the way. Today, many are questioning its future.
So what really happened?
In this episode, I sit down with former Stack Overflow COO Jeff Szczepanski to unpack how the company scaled from community to global platform, why it pivoted into enterprise SaaS, what drove the Prosus acquisition — and why traffic is now falling in the age of AI.
We also explore the bigger picture:
Are LLMs replacing developer communities? Is programming still a viable long-term career? Are we in another tech bubble? And who wins — and loses — in the AI era.
A candid insider conversation on one of the most influential platforms in tech, and what its story tells us about what comes next.
👇 Timestamps & Resources below 👇00:00 Trailer & Introduction01:36 How Stack Overflow Became an “Overnight” Success06:30 The Founders’ Edge: Why Spolsky & Atwood Won10:15 Turning a Developer Community into a $1B Business17:19 “Facebook or Yammer?” — The Pivot to Enterprise SaaS22:45 The Birth of Stack Overflow for Teams28:40 How to Build a World-Class Online Community37:12 Why Monetising “Fly-By” Users Doesn’t Work43:56 Why Prosus Bought Stack Overflow ($1.8B Deal Explained)52:35 Is Stack Overflow Dead? Did AI Kill It?1:00:26 Can LLMs Survive Without Human-Generated Code?1:04:10 Is Programming Still a Viable Career in the Age of AI Agents?1:07:09 Are We in Another Dot-Com Bubble?1:13:29 Winners and Losers of the AI Race🔔 Don’t forget to subscribe for more unfiltered convos on technology, business, and defying the status quo.