I like to play with different scenarios, what would happen if this or that, or how would I do it if I were in that situation? So let's run this scenario (and try to work with me using the rules) and examine the different possibilities:
Let's say you are Satoshi owning 1 million BTCs and you decide to cash out. These are the rules you have to follow:
You want to get the possible most value for your coins.
You want to do it in a relative short period of time, so no cashing out slowly in 5 years version.
You want to keep your anonymity intact. At the end you want to have a shitload of money but still be the mysterious founder whom nobody knows.
I understand that the first 2 points could be economically contradictory, but that is why this is a thought experiment to be solved....
I am curious how would you do it, but please keep your plan according to the rules...
Here are my versions:
a/ The simplest version could be if I were able to find an investor who is willing to take off the coins from my hand all at once, but getting the cash eventually without giving up my identity would be a huge problem. I don't see the buyer mailing a bunch of cashier checks to an address as a workable plan. But if someone can solve this problem, that would be an acceptable solution, and probably the simplest.
b/ Now I could keep sending coins to a brokerage, then later on cashing out even without trading, but that way at least the owner of the brokerage could follow the money path and identify me. So maybe a better version of this would be opening up a brokerage and running it while laundering all the coins. This would be also good for plausible deniability if later on I have to explain, just how I got rich, I could say, by running a profitable brokerage. This plan probably needs more workers, I don't see one person alone running a brokerage. Maybe buying out an already existing one would work and it is faster...
c/ Another version I thought about and it is a relative quick way, although it needs to sacrify quite a few of coins. First I would start to move coins to new wallets and through tunblers, so people would get used to that old coins are moving. After the initial scare, they should be fine with it. After a few weeks I would start to donate big amounts to a bunch of charities. Let's say 20-30 charities well known and smaller ones. Among them one would be my own charity. In the long run the charities would start to use the coins so after a few weeks, months, most of the coins are in circulation and it is really hard or impossible to follow anymore which coin went what way. If some coins can be traced to me personally, I can always just say, I got it directly with the initial charity distribution... In this version I might have to give out 20-30% of the coins to others, but that would cause enough coin distribution that I would be just one out of dozens of recipients, even if eventually a coin is traced back to me...