When i was a server at a high end steak house i had a regular that would come in at least once a month and asked for me every time. He tipped me $1000 no matter what his bill was. He was one of our most important guests. When he would call for his reservation, management would call me at home and tell me. That guest would be my only table for the night so i could focus all my attention on him...



Tipping out
I would tip out my sommelier $150 bcuz he helped sell more wines and helped with re-pours.

Then i tipped out the bartenders $20-30 (which NO other servers ever did) if the table had any cocktails.

I would then tip out my server assistants (backwaiters) $40 each (they were usually 17 y.o kids so that was a lot for them)

Whenever my regular came in i always spread the wealth. Also, it helped keep the hate at bay. People can be extremely jealous of your good fortune.
Even after tipping out the others, which wasn't even required, i always walked with mad cash...

The guy was the coolest millionaire i ever met. So down to earth and humble.