At some point, people realize that they are underestimating their projections and that leads them to re-calibrate expectations with stakeholders. In this case, there is no re-calibration, which leads "non-believers" to think he is a serial liar. The answer is likely in-between, he knows he underestimates it and he is aware that if he doesn't do so, there wont be enough pressure on the employees and the money would likely dry up fast.