The C-level guys were nice, but just insanely rich and so didn’t really have a grasp of how the rest of the world worked. One time the CFO’s wife broke her iPhone on a trip they were on, and he had me on the next plane to Los Angeles to bring her a new phone (they didn’t want to go to the Verizon store and deal with waiting and set up), so I configured her new phone (which was basically just logging in with her Apple ID…) and flew down to LA and drove the phone to their hotel, dropped it at the front desk, and flew back in time for dinner.
I had an MSP client that had a single IMAP email account for their entire company. I mean everyone, all the way from the mail guy to the CEO. Apparently it was a legacy thing from when they started the company and didn’t want to pay for multiple accounts. It was insanity. The entire office workflow consisted of them constantly yelling at each other on who was supposed to reply to the emails as they came in. And because it was so many people simultaneously accessing the mailbox and the client they were using (Eudora) it would crash all the time.