FWIW, Netflix gives you 10 years. Despite the fact that I left a few weeks ago, I still have about six years left to exercise them.
If he exercises now, he only gets the raw value (current price - strike).
If he waits to exercise, he get the time-value of money and implied leverage (he doesn't have to cough up the strike until he exercises), and the optionality part (if Netflix goes below the strike, he can decline to exercise).
He also can hedge by short-selling (and lock in a sure profit no matter what), but you'd need a big-value account at a brokerage to hedge on favorable terms.
But then again, if he exercises in one year and does not sell that year, he gets the tax bill in the exercise year, potentially with no way to cover it.
It's a lot more complicated than it should be.
It's interesting, because I thought about this. When I worked for the company I wasn't allowed to hedge, because you can't buy shorts in the company you work for.
Now that I'm out I can, but the problem is, the company gave me such good options there is no way I can buy an opposite option for the hedge. For example, there is no retail short for more than two years, but my options still have between 6 and 9 years left.
Also, don't write covered calls, that gives up too much upside. Instead, sell outright.
I probably won't look for something new for a while.
Financially, the move hasn't made a lot of sense. We moved to a cheaper country and we've not been short of rent/food/baby clothes etc, but I have drawn down quite a lot on my capital.
Nonetheless, I am 100% positive I made the right decision. I expect to look back in years to come and be grateful of being able to spend so much time with my newborn.
Everyone has been very supportive of the idea!