After thinking about this for a bit, you were somewhat correct, at least in the sense that the hotel owner would get shafted. I will have to make some assumptions to explain. In our system, there would be taxes on every transaction. Let's assume the tax is 10% for ease of things. Let's also believe that hookers pay taxes and provide legit transactions. The hotel owner would pay $45.45 to the butcher and $4.55 to taxes. The butcher would pay $41.32 to the pig farmer and $4.13 in taxes. The pig farmer would pay $37.56 to the feed owner and $3.76 in taxes. The feed owner would pay $34.14 to the hooker and $3.42 in taxes. And finally, The hooker would pay $31.04 to the hotel owner and $3.10 to taxes. All of them would still be in debt. In reverse order: The hooker would still owe $18.96 to the Hotel owner The feed store owner would still owe $15.86 to the Hooker The pig farmer would still owe $12.44 to the feed store owner. The butcher would still owe $8.68 to the pig farmer And finally, the Hotel owner would still owe $4.55 to the butcher + $18.96 to the traveler. The hotel owner lost $23.51 on the deal.