Entrepreneur is from one of the hosts wives attempting to recall the name of the enterprise and incorrectly identifying it as the entrepreneur.

I have listened to most of the greatest gen and honestly I have no idea where half the stuff comes from but I do remember that one being in one of their opening chats and then becoming a fixture in the show.

I also sorta agree that you either get a joke tattoo or a memorial tattoo and not both, but to each their own.