Bitcoin is a free world, fiat is a regulated world.
  1. The words "Bitcoin regulation" DO NOT mean regulating the free world. It means regulating the border between them.
This is a common mistake. So I don't blame you. But pls stop spreading it.
  1. Also, things can get regulated in theory with out the rules being enforceable in reality.
We're talking theory here. If you want to argue that you can meet your pals in a pizzaria and send the 1 sat and nothing can stop you... Then you are right. But this is not what I'm talking about and you know that.
If we're talking theory, let's start with why regulations exist and why Bitcoin was created.
Regulation requires enforcement. Enforcement requires authority. Reality has no authority greater than the individual person. Any person is capable of understanding anything that is understandable. Thus, there is no way to, for example, communicate in such a way as to not be misunderstood/misinterpreted--because theory creation happens in individual minds. All observations are theory-laden. There is no "authority" that has some magic ability to understand something that any other human could not in principal also understand.
So, back to enforcement: Force and coercion are always impediments to creativity and understanding real explanations. If the explanation is understood, for example the risk with buying Bitcoin, then there would be no need for regulation. Kids ask for bumpers at the bowling alley, sure. Sometimes, perhaps, people will ask for 'bumpers' at their shitcoin casino--but there's a difference between an option and force. Regulation isn't about optionality in principal.
Bitcoin is a way to do what rich people have done for ages. Move between regulatory games (read: governments). If you buy Bitcoin once, and you have enough money to travel and get around, that means it's possible to choose any jurisdiction you want.
The underlying theory behind regulation is something like: "people are too stupid to understand something and/or control themselves, so we will force them to do something until they either adopt the behavior without understanding it, or understand it to the point of not questioning it." Regulations change when disobedient creative people break the rules to solve problems. In this war regulations are always a parochial solutions to long term problems.
If you stretch the definition of 'regulation' to encompass 'explanation' (reason), then Bitcoin itself always has its own regulations which users agree do when they use the software. Regulations about fees, where the fees go, when transactions will occur, who gets to make those transactions, etc.
Is it useful, then, to add extra analog regulations on top of Bitcoin's coded 'regulations'? Why? I'm not sure it is. However, I think the way to do that, for example solving the long term problem of digital stablecoins, isn't by going backward. It's by going forward. Something like Somsen's Spacechains which create anti-speculative one-way-pegged sidechain tokens directly on Bitcoin. But try explaining that to "regulatory authorities".
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