Football

Well I don't know how his company does it, but typically the tips cannot be expensed and come out of your own pocket. His company are relatively small, so he's not had a huge windfall yet so this would impact him. What individuals do when they're under peer pressure is something that they might regret later. There's a place between being responsible to the person leaving the tip and still leaving a damn good tip. If the company paying for this was a lot larger, which would allow me to assume the boss guy had already extracted some big pay day from stock options, etc... then sure, wouldn't have intervened... but I'm on the other side of these things at times and have sometimes needed to drop my entire monthly income on a work related thing I cannot expense... I can reason that in the long-run it's worth it, but in the short-term it can hurt, so I don't assume that he can afford the tip, or that the company are covering the tip.