By risking their money on an investment with no promise of return?
I think you’ve hit the heart of the issue. The restaurant didn’t screw up, except by not having perfect anti-theft measures in place. But the buck has to stop somewhere, and in private commercial establishments, it stops with the owner.
People saying Bob failed to pay his bill have not convinced me at all, and in fact I’m wondering if I’m crazy or you guys are. Paying your restaurant bill by leaving cash on the table is the normal, accepted way to do it. The “check is lost in the mail” analogy does clear up the thinking on that a little, but I don’t think it applies. It’s more like paying your bill by going up and handing cash to the landlord, and the landlord comes back later and says “I misplaced it, can you pay again?” Having waiters collect money from table tops at their leisure is how restaurants get paid.
It’s on the restaurant owner/manager to ensure there is enough staff to watch every table to prevent this sort of theft, or else eat the losses on whatever gets stolen due to busy or distracted staff. The could have scheduled another worker for tonight, but I guarantee they saved more money by leaving him off the schedule than they lost by this theft. But the point is this isn’t the customer’s or employee’s calculation to make. That risk/reward calculation falls squarely in the owner’s lap.
Bob fulfilled his responsibility completely. The waitress has no responsibility at all, and shouldn’t even be part of this hypothetical. Thank goodness we have decent a restaurant owner here in the thread to assure me not every server is held responsible for dine and dash bills or I’d lose the rest of my rapidly shrinking faith in humanity.
This highlights the difference, in my mind, between wage earners and entrepreneurs. One takes risk, the other doesn’t. Waiters should get paid their wage regardless of their job performance. If they perform poorly they can lose tips or be fired, but the one benefit to earning a wage is that if you show up, you know you’ll get paid and how much. Taking a wage or salary job is the opposite of an investment. If the company does amazingly, my boss might share some of those profits, but they’re his to share or not as he sees fit, assuming my employment contract doesn’t say anything about profit sharing. But if the company does poorly, they can’t make up for their losses out of my paycheck. The most they can do is ask me to work for less money or fewer hours, or lay me off.
That’s the trade off. As an employee, I know I’m going to make $X/month until I quit or the company fails, but as an owner, I know my income will vary with the success of the company. There might be losses, but the idea is that the potential rewards are much higher. But so are the downsides, which for many entrepreneurs might mean losing their complete life savings, retirement and home. But they could also become billionaires, which no mere employee will ever do.
Anyway, let’s change the hypothetical a bit: Assume Bob pays, the waiter pockets the $20, and tells the owner that Bob dashed. Is Bob responsible now? Why or why not? He still didn’t wait until after he saw the cash go into the register. The thief is just now the same person as the waiter. In neither case did anyone see the theft. In both cases the owner believes it’s a dine and dash. Is Bob still on the hook?
Ultimately, realistically, the owner is on the hook whether Bob paid or actually did skip payment. They have zero evidence Bob lied or failed to pay, and any legal proceeding will cost several orders of magnitude more than the loss itself. The owner is eating the loss either way.