The Death of the Middle-Class Musician

I understand that you don’t like the European taxation regime, where the bulk of the tax burden is carried by the middle class, but I find it strange that then you give Bezos as a negative example. It is strange, because in US, unlike in Europe, it is the wealthy who pay most of the taxes. Our middle class pays very little tax, unlike middle class in Europe.

That should be true, but it doesn't end up working that way because people become corporations right? The actual tax burden is footed by the people making just enough to call rich, but not breaking into the territory where it's worth hiring an army of tax lawyers to reduce it to zero. This is bad.

No, that’s just not how it works. People cannot become corporations. You cannot hire an army of tax lawyers to avoid owing any tax. There are no major “loopholes” either that would help you avoid paying tax on actual income you make. You are just repeating some vague bullshit people say on the internet, but it’s just not true.

Denying it won’t make these loopholes go away.

The US’s CGT base cost uplift on death is insane, and only does not get repealed because it enables the super rich to never pay tax via the ‘buy borrow die’ strategy.

The US’s carried interest rules for hedge funds and private equity partners are insane and only exist because the affected individuals bribe lawmakers and presidents.

There are many insane things about the US tax system, but it is ultimately funded by the rich and only a little by the middle class.

Personally I think LTCG should be taxed as income and not at a flat 20%, but because that might actually work nobody proposes it and our lefties want a "wealth tax" instead.

The "buy borrow die" strategy is a meme. It just doesn't work the way you think it works. People just repeat stuff they heard on the internet with no real understanding. It is useful to avoid paying the capital gains tax in the very short term, but is useless for periods over 4-5 years, because it loses you more money than you'd spend on taxes.

To be specific: let's say that you own $1.1B worth of stock, $1B of which is unrealized long term capital gains. If you sold it all today, you'd owe $200M. Let's say that you're 40, you spend $5M a year, and you die at 80. So, you need $200M to finance your lifestyle, and then the remainder is a part of your estate. If you just sold $240M today, you'd pay $40M in tax, and had $200M after tax cash in your checking account to spend over the next 40 years. If you instead borrow $5M a year against your stock at very attractive terms like interest rate of 5%, and no payments until your death, you'll owe $200M on interest over these 40 years. Just paying the tax would have saved you $160M! It's even worse if you get more realistic terms, because 5% rate on a personal loan is too good to be true, and you'll need to borrow even more to make the regular payments.

What about the remainder of your estate? Depending on whether you just sell as you go, or borrow to finance your spending, your estate is left with something between $500M and $800M. Guess what, now they owe estate tax, which is 40% of this sum (minus $30M exemption). Oops!

You can avoid the estate tax, though, but the kicker is that all of the ways of doing that do not allow you to step up the basis upon death: they just allow you to avoid the gift tax, but they do little to escape the capital gains income tax. No free lunch here either.