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Comment by toast0

The state goes out of their way to encourage it.

Let's say you just won the startup lottery and you've got a significant amount of now tradable stock. Some of which was early exercised and the cost basis is effectively zero. Some of which was RSUs or non-qualified options and you owe ordinary income. And that you're way over into the top tax brackets.

If your zero cost basis stock is Qualified Small Business Stock (QSBS), there's a very nice discount on federal capital gains, so you might not need to do the rest of the stuff.

Otherwise, if you donate your apprechiated zero basis stock, you get to save federal capital gains of 20% + 3.8% net investment income. Plus it offsets against your ordinary income that's 37%. So that's a 60.8% discount on being charitable for the feds. If you live in California, capital gains are regular income, so you're saving 13.3% because the capital gains go away and offsetting 13.3% on your ordinary income, so your total discount is 87.4%. In other words, your difference in cash after taxes for selling $1M of zero basis stock or donating $1M of zero basis stock is $126k.

When the government is telling you it only costs $126k to give a charity $1M, it's pretty compelling. The math used to be different, when you'd get credit for state taxes on the federal return, but that was many years ago now.

parent toast0 1 year ago

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