Here's a tip that pretty much every philanthropist out there knows, but would probably be helpful to the HN crowd. If you donate appreciated stock, you get a "d

Here's a tip that pretty much every philanthropist out there knows, but would probably be helpful to the HN crowd. If you donate appreciated stock, you get a "double" tax break, since you don't pay capital gains tax and you also can deduct the donation amount. For example, you have $1000 of tesla shares that you bought for $100 a few years ago. You want to donate some money to charity now. If you sold those shares and put them in your bank account and then donate cash, you'd owe capital gains tax (15 or 20% depending on tax bracket) on the $900 gain. So if you donated all of your Amazon stock that way, you would give a donation of $1000 - (900 x 0.15) = $865 and you can take an $865 tax deduction if you itemize. Alternatively, you can donate $1000 of appreciated tesla shares directly to a charity. Now, you don't owe capital gains, AND you can take a $1000 tax deduction. Double win. Rich people who give to charity are well aware of this loophole. For them, it pretty much never makes sense to donate cash if they have appreciated assets they can give instead (at the very least you might as well donate the stock and then buy it back later at a higher cost basis, although I think there might be rules about buying the exact stock again within 30 days). And in my experience, most charities are happy to take stock for this reason... because their major donors only want to give stock, so they already have the infrastructure in place for accepting it.*