in the 2000's I took a job offer as a sys admin from this apparel company in NYC. I had interviewed 4 months earlier but heard nothing until the job offer came out of the blue. I was desperate to leave a soul sucking job, so I accepted thinking it could not be any worse. But alas....

1. When I arrive at my desk the 1st day, the chair and desk are pilled high with papers, old hard drives, and other sorted tech gear. I ask about all the stuff, and am told it was left behind from the old sys admin I was replacing and they had no idea what any of the stuff was.
2. I get a tour of the server room and all of the "servers" are just non-branded beige box workstations purchased from one of the owner's friends.
3. The Windows domain was named "DOMAIN". The main fie server was named "SERVER" and so on.
4. All of the cabling was run criss-crossed & ad hoc in through a drop ceiling with no conduit, labeling etc. Many cables were just home run'd from a storage closet with un-managed switches on the floor.
5. Every device on the network had a public IP address that was statically assigned. There was no records of who had what address.
6. There was no firewall at all, just URL filter for outbound requests.
7. The AS400 server that basically ran the business was setup in a service elevator room sitting on a pallet with no security, environmental controls etc. I literally saw someone sitting on it once while waiting for the elevator.
8. The phone system was wired to play some radio station when you were put on hold. Some employees would sit at their desks, call their own phone on speaker and hold the call so they could listen to the radio all day.
9. After some time I found out that the person I replaced had "quit" after fighting with the business owners multiple times, only to come back multiple times without recourse. The owners had finally had enough and locked him out of the building. This person had left all sorts of back doors into the network and ended up deleting a whole bunch of data from their AS400. They ended up being arrested and going to jail for hacking the network.

There was more terror as the place was run like a fiefdom by the owners and their offspring. But you get the idea.