I purchased a small liquor store in a "neighborhood" last year and transferred their service from the previous owner. I filled out a stack of paperwork including an auto draft form to have them debit their monthly bill from my business account.
After 6 months the rep showed up and told me that it was his fault that my account was never debited but that I would have to have them reconnect and start a new contract. When the tech showed up he informed me that the equipment was never connected properly and that had I attempted to use it to call for help it wouldn't have worked. I was shuffled around customer service reps for 6 hours all of whom I was polite but firm with in that I wanted a reduced bill from the 1,000 dollars that they were trying to charge me for services that they didn't provide. After a lot of bs about how they agreed and would do something to reduce my bill they never called me back.
When I got the same bill the next month I called them again and they told me that I was current and that their billing system was messed up.
The following month they sent my business to collections for the full amount with the option of paying two thirds the amount to settle the debt. The most infuriating thing is that I had offered to pay the company a reduced amount originally but I guess they would rather screw over their customers than work with them.
Monetary Loss: $1000.