Dr. Dolly: My question pertains to tax loss harvesting. I recently stumbled across a post you made back in 2017 about the asset allocation of your portfolio. It seems to me, at least conceptually, that there could be more opportunity for tax loss harvesting if a larger number of different positions are held. For example, if an investor owned 10 taxable positions instead of four, would it create more frequent tax loss harvesting events? Do you actually only hold four different stock funds in your taxable portfolio? If so, do you feel it limits your ability to tax loss harvest?
Today we get into the weeds of tax loss harvesting. With the current state of the market it looks like there are a lot of out there who have decided to tax loss harvest. Today we answer your questions about the wash sale rule as well as discuss if adding some complexity to your portfolio could create more opportunity to tax loss harvest. We also tackle some questions about taxes, the ROBS program and how to minimize your taxes as a 1099 employee.
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