Someone asked about pulling tons off from exchanges, and while I will give you might copy and paste answer I gave them on how to do that. This isn't what most rich people do. What most do is they

1. Get a loan out on their holdings. If the holdings are above a given $ value and the place they are dealing with is cool. The loan is a super super super low interest (like barely above 0%). Some they buy out things like rental properties and use the earnings from that to pay for the interest and taxes. (BTW for those of you wondering why your remote work is ending even when your bosses flat out admit more work gets done while people are remote, it cost the company less, and remote work is far far far more green and better than physically having to show up. Well this is why. It is more about rental properties and forcing you to be in an area that has a high chance of you shopping at the stores or living at the places that your boss owns the land. Look it up, this practice heavily happens. The loans are several million on the low side. So a lot more people use this than just the 1%.)
   1. Side note, if you sell then you are taxed. But if you get a loan out against your assets. There is no tax on that. Meaning if you were sitting on $10m of coins, and you took out a $8m loan that you use to go to the beach or whatever. You aren't taxed on that $8m. The rental properties most who do this with to pay the minimum, they do have to pay taxes on that. But what some do is they have a shell company hold the asset (whatever that is being rented. If it can't do it's job and they can't sell the asset. The asset becomes toxic. They can then bankrupt the company, or they can officially abandon the company and asset. This now becomes a major tax deduction. This is why some people are able to get and use a $40m tax deduction.) But at the end, if you want the loan to not be collected on, they can have another property in another company to make up the difference. (note I'm not a lawyer or a tax person, but you can easily look this stuff up. And anyone who wonder about Trump using tax loopholes, you should already be educated in most of this.)
2. They only use part of what they made. Like when you sell for fiat you can't gain more in value. So it is smart if you have a million or so, to try to keep it in investments where it grows. But with crypto you can stake it. Like a 10% staking for a million is $100k in pure passive income. So instead of selling the million, why not just sell the passive income as you need it. You're being taxed on it anyways.

In some cases they use other tax loopholes like gifting, freeports, and giving "loans" to a family or friend other things to get around the system. Note things like https://www.schwab.com/resource-center/insights/content/family-loans-should-you-lend-it-or-give-it-away

There’s also the question of delinquency to consider. When a family member can’t repay a loan, the lender rarely reports it to a credit bureau, never mind a collection agency. However, should the lender want to deduct a bad loan on her or his taxes, the IRS requires proof of an attempt to collect the delinquent funds.

Again, I'm not a tax person or a lawyer. Obviously if you have that type of money and don't get the proper people. Then you're an idiot anyways IMO. But the point is, rich people try to find any way to get around the tax system, and unlike us poor people. The system is built in such a way they can, because having that type of money opens a lot of doors.

And at the end, it comes down to 2 things.

1. How to not pay taxes on your gains (or pay as little as possible)
2. How to have your gains keep growing faster than inflation

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Now lets say you want to just sell everything off and you're walking away from crypto. Or maybe you just don't trust those sneaky exchanges for some reason.

What happens is simply this, each off ramp has a max amount of fiat you can withdrawal from per day/month/year. Look at the limits.

Each exchange has a given amount of liquidity.

So if you are stupid, you would try to sell all in one place at once and maybe lose 20% of the value or more due to liquidity. And then take the fiat out all at once from one place, and maybe get it locked up in limbo for a solid month or so.

Here is what you should do

Step 1

Figure out how much money you're worth, and where is your off ramps for that coin. Then split them up in several off ramps based on the limits. Try to go 20% below the limits because some off ramps are stupid.

Step 2

WARN THE OFF RAMP ABOUT WHAT YOU ARE DOING. In you are in a binance US situation. Good luck on that. Swap to another crypto like ALGO and send it to something like Kraken that is worth a damn. Like you can notify Binance US, but their current customer support might not get back to you in 3 years, and the best you will get is a copy paste answer to a question you never asked.

Step 3

WARN THE BANK. This lets them know they are about to get a bit of money and for them to not lock it up. Or at least be ready to unlock it pretty quickly and maybe you can ask them for advice.

Step 4

Start selling. Part of the reason for warning the exchange is so they would give you a heads up on how to go about this. Like can their system stand you dumping $500k, or do you need to baby step it. On the off chance they are an idiot or lied, personally I could sell $20k every 15 to 30 min. Watch to see if the price really dumps, and then stop when that happens.

See, what you are doing is looking to see if the liquidity is really there. Lets say you are on exchange A and doing this and exchange B you aren't. Watch both charts and if you see the price just drop in exchange A, you are going beyond what their liquidity will allow. Your choices is to wait long and/or sell less per time. Or try another off ramp.

(Most BTW sell $45K per go per hour)

Step 5

Pull whatever amount out. Hopefully your bank isn't an idiot, and hopefully the exchange isn't an idiot. Don't go to the limit because most exchange will "screw up" in locking the transaction because they might not have the money or because they really did screw up. This is also a major reason for step 2.

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Step 6

Go cry in the corner because after all of that, you now owe the IRS half of that.