No, not really. If there was some other goal besides the honest exchange of the hat for the money, then maybe. Fraud ("the hats made of gold and is therefore a great value!") and price gouging ("it's the only hat for sale on a sunny day so I'm selling it at a 1000x markup!") might be crimes in some contexts. As mentioned, money laundering (avoiding tax or other legal requirements to move money) is also a crime.
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If it can be proven to be "self dealing" aka your NGO, charity, or non profit purchases or accepts a tax deductible donation of say, a portrait of you, from you or one of your businesses for hypothetically, 100 million dollars, then you may, if you did something particularly odious such as say, run for president. Then you might lose the legal ability to run that sort of organization.
No, but if the sale goes through and you don't declare it to the tax man then that's probably illegal.
No.
Even Martin Skreli, the dipshit who jacked up insulin prices by 300% didn't get in trouble for that; he went to prison for security fraud or someshit.
However, if there was say a crisis going on and you raised the price of water you were selling to capitalize on others' misfortune that tends to be illegal. Like when stores were price gouging on hand sanitizer during the height of the covid lockdowns.
Skreli was absolutely 100% capitalizing on others' misfortune and the fact that he didn't get in trouble for that is incredibly bad.
WTS ice cream scoop. $1000. Free blowjob with every purchase!
That depends entirely on the country you're in, and the thing you're trying to sell.