I just moved to Microsoft and got a large 350k stock grant, at a near all time price high ~300/share. It beats over 4 years. Is there any option play I can use to protect my self against stock drops to lock in the 350k?

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Are there any anti-hedging provisions in the grant agreement?

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I do not believe so

Most companies that give grants have contract terms that forbid options trading or hedging in the stock.

Gotta keep you motivated and all.

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What level at MSFT gives you 350k grant? And is it annual?

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Curious, do they give you 350k worth of stock based on the value of the stock the day it’s granted or the day you join?

It vests**

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You can buy Jan 2024 puts

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Ha

No you best bet is to do nothing here.

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Uhh are they hiring?

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You can sell covered call 10% out quarterly. If it only drops slightly, the premium will offset it.

Altetnatively, you can also write ITM call, you'll get the difference between strike and market right away in cash but you'll lose out on all future gains.

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You can write Year-long calls at a lower strike.
So if it were to drop below that you'd secure the price.
But if it were to go higher, your "break even" would be Price + (Stock - Strike) and if it drops below the Strike, you'd keep your shares

At a high level: if you buy ATM puts for your desired expiry date (however long you’re planning on holding MSFT), your investment should be protected until that date.

Not the most productive hedging strategy though if you’re planning on holding for long term (premium increases for longer DTE)

Of course the premium for long ATM puts is mucho expensivo, so again, both strategies work. It’s just a matter of optimizing returns based on OPs sentiment

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