Private foundations are really a massive scam on the public purse so whenever you hear about the Gates Foundation and the like, remember it's just a tax dodge, nothing more. The way the rules work, a private foundation has to spend 5% of its capital on its intended purpose. Thing is, that 5% can include "administration" costs like paying salaries and benefits for the family. They really need to raise this to 10%, min…
Can someone explain how that charity foundation thing is a loophole? Who/what is avoiding taxes?
You're going to pay capital gains taxes, or just income taxes, on those conversions to liquid capital.
If instead you donate those securities to a "Charity", then the earned interest is not taxed, and you receive a tax benefit for moving the property to the charity entity. If the charity is happy for you to travel all over the world, then you're done. Same benefit accrues, tax burden becomes negligible.
What's left to determine (from our electronic armchairs) is: Does the charity do good for the nation, for the world, to an extent that it's worth forgoing the tax income? I expect that the answer is "Yes" for several of the charities we consider household names. I expect that the answer is "No" for the overwhelming majority of charities, by count or by endowment. We could start by taxing Harvard. :)
[0] Not that anything is dependable year on year, but that's the rate that university endowments made in 2021.