StealthP3D
Well-Known Member
Except he was already looking at selling shares to cover the bill.
If you just sell shares, you lose shares. 100% for sure.
If you instead sell a covered call you not only might not lose shares (but still get money), if you do lose them you get more money for them (both the premium, and the higher strike price, as compared to simply selling the shares outright.
In practice, it doesn't work like that. Because you have to sell enough covered calls to cover your tax bill with just the premiums in case the share price doesn't rise past the strike price. But if it does, then you have sold far more shares than you needed to, thus taking the problem you were trying to solve with this strategy (not wanting to sell any shares) and multiplied it many-fold. And the higher the strike you choose (in order to minimize the chances of the shares being called) they more shares you lose if they are called (because the premium is smaller and you need to sell more of them to pay your tax bill).
All you have done is traded the CHANCE to not have to sell any shares for the CHANCE that you might have to sell many times more shares than had you simply sold the amount necessary to cover your taxes.
There are no free lunches in this game.
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