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Re:Pinterest lets employees exercise options 7 years after l... by jedberg on Tuesday March 24, 2015 @12:47AM (#9254950)
> 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.

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.

Re:Pinterest lets employees exercise options 7 years after l... by fsk on Tuesday March 24, 2015 @05:19PM (#9259574)
Buy the longest term put and roll the position when it is near expiration. Don't fully hedge, just 1/2 to 1/6.

Also, don't write covered calls, that gives up too much upside. Instead, sell outright.