I have a relative who runs a small business. He says that 95% of his clients pay on-time or at least something close to on-time. There's 5% who don't. As a younger man, he said he took a few of these customers to court for claims in the 10-20k range. He wanted the money but it was also the principle of it. After a few such cases, he realized that he was spending time and money in order to recover relatively small amounts. Most importantly, this was taking away from his time running the business. He found it was way more profitable to just let these cases go and focus on what he's good at.

Now, if you are chasing people down pretty regularly, maybe you have a department dedicated to handling these cases and it makes sense. But if it's a once in a while occurrence, a few thousand dollars probably isn't worth the time and effort for an otherwise successful business owner.

Yes, but like others have said, I never thought it was worth it. I like to focus on moving forward.

I have a friend who worked for a large law firm and he told me that even they wrote off some unpaid bills or negotiated discounts. I was shocked to find that even when the lawyers could deal with the legal work themselves, they chose to pass.

That changed my thinking on the topic.

A few thousand dollars wouldn't be worth the time.

have you ever tried to do that? I paid $19,000 once to sue a company for $8500…

The reason was more to force their hand, but you don’t just “sue a large company” they will play games like ediscovery, and crazy-weird jurisdiction stuff