I have a very concentrated stock position from 17 years at two tech companies. 65% of NW is in two stocks with very low cost basis. (I know this is a problem) I was thinking through various options to diversify out of this and was hoping someone with experience in leveraging an exchange fund could tell me a bit more about how they thought about that decision, and if they were happy with the results. I was mulling over options and thought about the following which I would also like some advice on.
(1) sell 50% now (or over 1-2 years) take the LT capital gains tax hit while I'm in the highest tax bracket, rebalance in vti
(2) wait until I retire in 5-7 years and sell 50% in a lower tax bracket, rebalance in vti
(3) put 25% in an exchange fund sell 25% rebalancing in vti
I am 100% in stocks across brokerage, Roth, and 401k which is another area of risk, but anytime I've put funds in bonds I've lost money so I keep it in stock.
Submitted April 29, 2023 at 01:35AM by throwawayorchard https://ift.tt/m7OuKPt
