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Emily's avatar

Thank you for this post Andre! It is super helpful.

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Rodrigo de Salvo Braz's avatar

Thank you for the post. One question that remains for me is that here you only consider the one sale and do a greedy optimization that does not consider future sales. It seems to me that selling short-term lots and paying more taxes is always going to be worse than selling long-term ones since the taxes there will be less. Even if the short-term lot may pay less tax now, you are still paying a higher rate, and the long-term lot will have to be sold *eventually* anyway, so it is not like you're avoiding *those* taxes. This of course assume selling all lots eventually and therefore ignores estate planning, for simplification purposes.

I would like to write a complete simulation of different strategies taking into account multiple sales across time. While I haven't had the chance to do that yet, I did have this interesting conversation with ChatGPT, for what it's worth: https://chatgpt.com/share/68adf4db-b964-8001-a8c7-436475bcf51b

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