I think it doesn't have to be all or nothing, it could also be possible to have a balanced approach to this problem. If your options start to be worth quite a bit more than your buy in price (eg: 2x), you can exercise some percentage of them but keep the rest. People more vested in investing would probably say that the ideal strategy would involve picking some thresholds ahead of time. Either way, there's always some amount of luck in this. The amount of things you don't know is a lot larger than what you do know. You may also not be in the right financial position to invest when a great opportunity shows up.