Capital gains taxes are only requisite if you sell, Bob.  

Taking debt-free fully-collateralized loans, gifting to charity, setting up inheritance trusts, investing gains in opportunity zones, selling less than very generous NIIT cutoffs, moving to Puerto Rico, etc. etc. are all possibilities in the exact same rulebook, but result in more money going to family and causes we may actually identify with versus willy-nilly donating it to our government's system of black hole spending.

None of this should be counter to Libertarian thinking, am I wrong?

I understand that the sheer mental load of tax planning may be, well, taxing... But the system also provides an army of professionals to help with that, in the way of accountants, lawyers, and financial advisors. And they cost a helluva lot less than 23.8%. Some of them may even be friends and family. Libertarian even.

With qualified help and fore-thought, you, too, could have your cake and eat it. And maybe even sleep.

Nom nom.  Zzzz.

PS. Cheers to being a fellow POC raised with values by loving parents and working hard in life to overcome systemic racism. Although I happen to believe luck and appearance play more of a role than hard work in being "successful".