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Personal Investments • Should We Realize Gains at Once or Slowly?

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Serious answer: At your wealth and income levels I think you should have a Donor-Advised Fund as a conduit for your charitable giving which you surely must already do. Give shares held long-term that have appreciated to your DAF. Don't sell them and don't give them ALL away in a single year. Instead give them as you wish when you want to donate to the charities of the choice. The DAF makes it easier: You get the tax deduction while avoiding realizing capital gains and send cash from your DAF to the charity.

https://www.bogleheads.org/wiki/Donor_advised_fund

In essence since those shares were already dead money for years, there is no reason to ever sell them: just donate them whenever you want to make a charitable contribution.

Statistics: Posted by livesoft — Tue Feb 13, 2024 1:24 pm — Replies 4 — Views 295



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