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Looking for some feedback on a strategy I’ve been implementing for a while now. So anytime we have a sell off like this I use it as a chance to harvest tax losses and lower my cost basis. So recently when this tanked, I sold my highest cost shares (\~170) for a loss. And I bought slightly ITM calls for over 30 days out. I try to time the bottom but otherwise I’ll roll the calls to a lower price. Which tend to rack up losses but it’s minor. I figure a few hundred dollars to lower my cost 5,10,15 dollars is worth it. So I now have $115 calls with a total cost of 135. And before anyone says it, with regards to wash sales, you can avoid it if 1}you buy the calls before you sell the stock and 2}if you are OTM, ATM or \*slightly\* ITM but too deep will trigger a wash sale.
Ultimately I do this with stocks that I have a long outlook on for these reasons: 1}Rack up losses in the short term so that when I do take profits, I have enough to write them off against (I’ve been able to double my portfolio yet write off my entire contribution/investment as losses - obviously my gains are unrealized). 2}hold off taking profits as long as possible, borrow against it and let my kids inherit it at market price. Im investing for the long term, I mean I know not every stock I own is going to become the next Apple and turn into a steady compounder but at the very least, I can hold off realizing gains until they are long term with a more favorable tax rate.
Any thoughts?