My dilemma is one of take the money and run, or hang in there with Amazon. I really am interested in analysis and insight as to how to decide.
Just for sake of hypothetical discussion let's say $1 million portfolio, 85/15, everything except Amazon is index funds.
I just want to throw out the fact that there is a pretty interesting third option,
donate them to your very own charitable giving fund.Since we're speaking in hypotheticals here, hypothetically since you're on this forum and we're throwing around a $1MM portfolio you might have aspirations of Retiring Early in the not too distant future. Assuming that's true, and that you're still working and in a fairly high tax bracket, and that you expect you'd give $35k to charity over the course of your remaining life (including church or similar, if you like), then donating them is the
perfect thing to do with such highly-appreciated shares.
1) Since you're donating it to a non-profit (your fund) you don't have to pay a penny of Capital Gains tax.
2) This year you'd be able to deduct the fully appreciated $35k current value if you itemize your deductions (yes, a double-whammy tax benefit).
3) By taking the tax benefit now while you're working you can get much more value out of it than if you were to just donate to charities when you aren't (and presumably in a lower bracket).
4) You don't have to give it all away to charities this year, it can sit in your fund and even remain invested and grow until you decide who and when to give money to. The only caveat is that the money has to go to 501c3 non-profits and you can't ever get it back if you change your mind, since you've already given it away to a charity (your fund) and taken the tax benefits.
Edit: Never mind, it looks like this was already raised and answered. I should read more carefully.
