The point of it being a good decision was that it wasn’t a bet: they were locking in a known as opposed to it being unknown. I guess you can say choosing not to play is a bet of some kind but it is a different class of bet I think.

what constitutes a bad bet is largely in the eye of the beholder unless there are clear parameters to help define an EV. Also different investors will have different tolerances for risk. I have extremely high tolerance for risk and have been rewarded for that tolerance with outsized gains in the market over the years that have dwarfed all of my jobs combined in income except for my most recent stint at NVIDIA.

a financial advisor would always tell you to unload all shares at each vest since you are holding more shares in the form of future vestings.they would then tell you to diversify it into ETFs in a mean variance optimized portfolio tailored to your risk appetite using standard deviation of historical returns and correlation of underlying basket of goods. this is a solid approach that produces predictable safe returns.

I would rather let it ride since I have insider information at most companies I work for and have a better understanding of future returns on that stock that the average person on the street.

I say, take average advice, receive average returns.

:)