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<<Pixy replying to Jeffbuck about a major portion of assets in company stock (&options).>>

I agree with you 100%, Pixy, about the "sleep factor" of having so many eggs in one basket. But, depending on a lot of factors, at least SOME of the tax bullet could be dodged...

--in a 401(k), I beleive that the capital gains can be postponed in some cases when the company stock is moved out of the 401(k)

--if you are charitable, donating appreciated stock gives you the full deduction & you avoid the capital gains

--if some of this is left over for the estate, the heirs get the stepped-up basis of value at death.

Even with these possibilities, it is pretty scary to hope that the company's stock price would never crash in the 50 years until it is part of the estate. I would probably diversify as much as practical, or maybe a portion each year.
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