It is easier said. At the time of vesting probably you would know that the startup is doing well, it is gaining customers, and revenue figures look good. But yo

It is easier said. At the time of vesting probably you would know that the startup is doing well, it is gaining customers, and revenue figures look good. But you might not know if the startup is breaking-even, if so how profitable and even it is profitable, is the FMV high or low. If FMV seems tad higher, does your investment and tax incidence on it gives a better return than investment elsewhere (say index funds, stock markets, fixed deposits etc.). Add to it the uncertainty that some unforeseen risk/event could still cause the startup to falter.