We have the exact same objective. All I'm trying to do is accumulate as many shares as I can, while not taking on any crazy risks.
All of the long term option plays I make, I've calculated potential pay offs in # of shares, rather than in $ gained.
Therefore, I expect to sell my Jan'22 $500s around the time we hit $1,000 or $1,100 per share, and buy shares with the proceeds.
I think there's way more money to be made by holding onto them longer, but even if stock is $2,000 upon expiration, that'd only translate into less than 20% upside in terms of how many extra shares I'll be able to convert them into.
At $1,000 tomorrow or next week, those options will likely trade for ~$600 each, and can be converted into ~60 shares each. At $2,000 upon expiration, they would be worth $1,500 each (2.5x), but can only be converted into 75 shares, which is less than 20% upside.
So I plan to exchange those for shares around $1,000-$1,100, and then if there is another dip, recession, Q1 turns out to be a disaster, or something of that nature, I could leverage up a bit again through different options.
Thanks for this post and appreciate your detail. I fear I am not quite following your logic. Have you calculated the exact price the option would need to reach to be an exact conversion to the underlying 100 shares at $500? Long term gains may be a consideration in some taxing authorities but is another issue.
I think when you are saying "20% upside" that I get confused. 75 shares?
Are you saying that beyond a certain price the conversion limitation of 100 shares at the strike price being the limit of the number of shares that can be captured in some way influences your value decision of holding the option longer?