"Cat & Cloud" already have the trademark, and they are always using it in conjunction with the word "cloud." Meanwhile, Caterpillar Inc,
the maker of heavy machinery making over 54 billion dollars in revenue last year, is still suing this coffee shop in in an attempt to reverse their trademark around the word "Cat". Why?

As it's indicated by the podcast hosts, Caterpillar is doing this to a number of small businesses because they have a trademark for the work "Cat" as an abbreviation to the word "Caterpillar."

Theoretically you cannot, but if you are a multi-billion dollar company that is trying to own every variation of your name, then apparently cat is a fair game, and bleeding your local business dry is none of your business.

Cat & Cloud have spend tens of thousands, and it's only been one year and the matter hasn't even gone to trial.

Once you get the original notice of the lawsuit, you get to file a response. From then, the originator can come back with a "discovery" process, requesting documents about your business and its financials, asking questions that may help them in suing you. In this case, once Cat & Cloud filed the response, they also asked for the same information from Caterpillar Inc. There's no end to how much information each one can request, meaning whoever has more money can keep draining the other side's time and finances. The process is stacked against the little guy.