In the deceived businessman thought experiment, we are asked to imagine the lives of two businessmen, equal in net pleasant experiences, but unequal in the amount of deception. Both lives are experienced as equally happy from the inside, but one is deceived about many important things, while the other isn’t. When comparing these two lives, people usually report that the non-deceived life is preferable to the deceived life. Philosophers working on wellbeing have used this result to discredit experiential accounts of wellbeing, especially prudential hedonism. I argue that two structural problems with the thought experiment preclude it from being a reliable source of evidence for drawing conclusions about wellbeing, including discrediting prudential hedonism. If I’m right that these structural problems mean the deceived businessman thought experiment should not be used when arguing about wellbeing, then several other influential thought experiments with the same structural problem might also be under threat.