Within the first couple of weeks at Smergers, I noticed something strange about business listings.

They had images.

That sounds harmless, except a buyer could take an image from a listing, put it into Google Lens, and sometimes figure out which business it belonged to. Once they knew the business, there was nothing stopping them from finding the seller directly.

Smergers was a marketplace built to help buyers and sellers find each other, and we had accidentally given them a way to leave it instead.

So we changed the listing workflow to reject images that could reveal the identity of the business.

What was interesting about this wasn’t the fix. The fix was easy.

The interesting part was that nothing was actually broken.

The software was doing exactly what we had designed it to do. The problem was that a perfectly reasonable feature, when combined with the incentives of the people using the product, produced a bad outcome for the business.

So there are bugs in the code, and there are bugs in the business model.

The second kind is usually harder to notice.