The withdrawal amount is too big, I don't think there are banks or any local exchanges that can make you convert in one time with no worries.
That amount might be questionable to any exchanges if you're just a new user. So the best thing to do is to withdraw a couple amount gradually and use Bitcoin mixer to make sure that your address is clean and not connected to any suspicious address.
What is a Bitcoin mixer?
Why would someone will cash out all their bitcoin on this current situation, or cashing out one time if that's what you mean. You don't need to cash it out once, when you can do it in multiple times which may give someone an advantage, maybe price will go up later on, then a little hold on if it decreases.
You mean to treat my Bitcoin like stocks and bonds, which are only liquidated as needed? I thought about that, but I would be more concerned about managing risk by transferring BTC into relatively safer assets. That's the only reason I would want to transfer such a large sum. 30m can stay in BTC for diversification.
How would you go about cashing out very large sums of Bitcoin, or other cryptocurrency?
A hypothetical example:
You were fortunate to purchase five thousand Bitcoin, when it was only pennies a coin, and it's now worth a whopping $130,000,000. This is now sitting in cold storage in your digital wallet, and you want to cash out 100 million usd.
1) Are Coinbase and Gemini your only convenient options? Will they be able to cash out such a large sum, and send the proceeds to your financial institutions without issues?
2) FDIC insurance only covers up to 250k per bank account. So, you would need more than four hundred accounts in order to cover all 100 million dollars. Is there a better way? Can you just send all 100 million directly to your Vanguard brokerage account? How do the ultra-wealthy do it??
3) What would happen if you suddenly sent a hundred million dollars to several banks/financial institutions? Would the IRS be immediately notified? Would your accounts get frozen? How do you avoid this?
No snarky answers, please. The above are only hypothetical examples. I don't own 5000 Bitcoin. Not even remotely close.
It is easy enough with multiple steps.
Assuming you are USA based and your cost was next to nothing.
Consult a tax lawyer and a tax accountant.
Move to a no tax state.
Step 1 Move some coin not much 3-5 coins to coinbase.
Step 2 sell the coin.
Step 3 move the 100k to a brokerage that sells fed bonds buy some. that is for you JJG
Step 4 Move some coin more say 6-10
Step 5 Sell the coin
Step 6 Move 200k to your brokerage buy some bonds.
Repeat over and over slowing increasing the moves.
Pay a shit ton of tax ahead of time.
Pay attention to your tax advisors.
Sounds good, but I would buy mostly stocks (90% stocks/10% bonds). With 100m, I would be able to afford to do that.