Hacker News Reader

Comment by 2pointsomone | Hacker News Reader

Wow I did not know she gave her $150m on the sale of Bebop to charity. That is very very impressive and must be celebrated more.

View on HN

Yes, but... At her tax bracket and future earning potential, the money is very likely to be worth more as a donation than as income. Total tax rate would be above 50%, but as a donation you get a $1-for-$1 deduction against future income. So the choice is something like 'keep 40 cents on the dollar today, or negate 60 cents on the dollar in taxes tomorrow.'

Also, the money isn't really all gone to a 3rd party, it's in a foundation-type entity similar to how Zuck does it.

That doesn't make any sense. The deduction is in the same amount of the income she just received (I assume her basis (since she was a founder) was very low or near zero). It will not be available for "future income".

The foundation-type entity is correct though, she will still be overseeing how it's spent.

You just write it off.

https://www.youtube.com/watch?v=XEL65gywwHQ

No, that's just it! You donate the appreciated security directly without exercising/selling them first, so there is no recognized income on the personal tax return. Plus you still get to take the deduction on the fair market value of the security.

See: http://www.fidelitycharitable.org/giving-strategies/tax-esta...

Ummm...the whole point is that she sold those shares to Google, donating large "paper profits" is a total other thing.

EDIT: Perhaps you're saying she donated her shares to the Donor Advised Fund first, and then the Fund sold the shares to Google? Possible I guess, but that's not what the SEC notice said.

https://www.sec.gov/Archives/edgar/data/1652044/000090342316...

"Diane Greene exchanged 7,244,150 shares of bebop stock for 200,729 shares of Alphabet Class C Capital Stock at $740.39 each in the Merger, plus cash for fractional shares. Ms. Greene intends to donate the shares exchanged to a donor advised fund."

Getting past my 'expertise' in this area, but she didn't personally sell her shares to Google. Her company was acquired by Google, and her shares in bebop were exchanged for shares of Alphabet. A merger/stock exchange is not a taxable event, she would keep her near-$0 basis in the now Alphabet Class C shares, and then donate the highly appreciated Alphabet shares to the Fund.

You have to structure the deals this way, otherwise you lose more than half of your company to the government. When marginal rates exceed 50% and you have dependable future earning potential, yes, giving away unrealized gains can be worth more than realizing them.

Yeah, but at that point, ABC shares are basically cash money--they may as well be Treasury Bonds given how liquid they are. She could easily sell half to cover the tax bill and keep the rest. So no, I don't see how "the the money is very likely to be worth more as a donation than as income."

Liquidity of the shares is not in question. If the tax rate is over 50%, you have two choices; sell the shares and keep < 50 cents on the dollar by realizing the gain, or you can donate the shares to your Charitable Fund, and carry the charitable deduction against future income. The next year when you earn $XX millions, half of that is now tax free because the charitable deduction carry-forward. Dollars which otherwise would have been taxed at > 50 cents on the dollar. Selling the shares is worth < 50 cents on the dollar, but the charitable deduction is worth > 50 cents on the dollar because of the future tax liability that it eliminates. That is why I say it is "worth more as a donation".

By donating $150m to the Fund, you not only get the self-directed Fund with $150m dollars in it (which is a fun time in and of itself) but you also get $150m in charitable deductions. Each dollar of that deduction eliminates > 50 cents on the dollar of tax liability. Donating to the Fund effectively lets you have your cake and eat it too, again, with the caveat that you expect to have enough future income to use it all up, while remaining in the highest tax bracket.

Charitable contribution deductions are limited to 20-50% of income (depending on type of charity you are donating to).

You can "carryover" deductions from charitable contributions that you are not able to use up in the current year for up to 5-15 years.

https://www.taxslayer.com/support/530/charitable-contributio...

Point taken (after the correction; I run a nonprofit so yes, you aren't entirely correct), but it is still forgoing a sizable income, and that is admirable.

Reply on news.ycombinator.com