My friend Eric once proposed something similar, except where two charitable individuals just create the security directly. Say Alice and Bob both want to donate $7500 to Givewell; instead of doing so directly, they could create a security which is “flip a coin, winner gets $15000”. They do so, Alice wins, waits a year and donates for $15000 of appreciated longterm gains and gets a tax deduction, while Bob deducts the $7500 loss.
This seems to me like it ought to work, but I’ve never actually tried this myself...
My friend Eric once proposed something similar, except where two charitable individuals just create the security directly. Say Alice and Bob both want to donate $7500 to Givewell; instead of doing so directly, they could create a security which is “flip a coin, winner gets $15000”. They do so, Alice wins, waits a year and donates for $15000 of appreciated longterm gains and gets a tax deduction, while Bob deducts the $7500 loss.
This seems to me like it ought to work, but I’ve never actually tried this myself...