LA, if on the inbound in any case you are on a DIRECT join, i.e. there is no PROCEDURE required to get you established into the hold. Thus, the first time you pass over the beacon you are "entering the hold". If on a parallel or teardrop one would obviously delay the message and "entering the hold" is the only phrase I can recall ever being used.
Well truth is during IR training it was the same bleeding NDB we practiced with so only a couple of different situations ever came about. Since I've been flying slightly bigger metal commercially, I've only entered the hold 3 times in about 4 years! all occasions they were direct joins. My experience with holds is limited so I could be wrong.