Losing money while growing revenue isn't necessarily a bad thing. This can be caused by growth investing, and is often the right thing to do. Amazon is a famous example of this line of thinking.
Losing money while growing revenue isn't necessarily a bad thing.
If you strongly believe that you have a viable long term plan to switch to a profitable model when the time is right, sure. When AI comes along and wrecks your business before you manage to extract the profit then you can say (with hindsight) you made a mistake by waiting too long. I'm not saying this is the case for SO, but it might be. Time will tell.
Getting to profit quickly is a hedge against change. Nothing guarantees that your business will be around forever. If you don't take the money when its there you might lose the chance.
But what's there to even invest in for SO? Ad tech? Selling some LLM trained on their data? I can think of a whole bunch of silly ideas here, but none of them seem anywhere near comparable to Amazon investing in a vertically integrated supply chain for e-commerce and cloud computing.
Best of luck to them, I know they've been trying to push a "for teams" product for years but I've never heard of anyone who has even expressed interest in it. Atlassian will be a tough nut to crack. Job board seems like a much better idea, but I'm not the CEO or investors so what do I know?
The job board was also a finished product. They could have automated just about anything manual, and kept it going with a small team. For the brand promotion alone it was worth it to keep it going.