The "dao" here is not designed in a way that is truly decentralized. It is susceptible to certain centralizing flaws. There could be a dao that is designed in a way that resists censorship, that would be more interesting.

You've obviously never heard of extradition have you?

It's a matter of degree. It might be a good risk to run a licensed recreational pot business in Colorado. Technically you're committing a federal crime, but there's a non-enforcement policy and as long as there's safety in numbers and a D in the White House you're probably OK. However, it's a bad idea to run a recreational cocaine business in any state. Requires a knowledge of the specific regulators, their views, and unofficial policies, to get this kind of decision right. Bringing this back to bitcoin-land, it seems that many bitcoin exchanges have knowingly operated without required state licenses for some years. However, the founders are not in jail. Why not? I think they have taken a considered approach to "partial" compliance, working out informal agreements with state regulators for eventual compliance, and avoiding operations in states that take a more hardline view. Eventually the top exchanges like Coinbase will get whatever licenses they need to, just a matter of time and $$$.

Yes, it comes down to risk management and decision making under uncertainty. i.e. how much of a competitive advantage can we gain by pushing the regulatory limits, and what are the potential downsides and probability associated with such downsides.

PG has expressed a view that he favors start ups that push regulatory boundaries, but I'm sure his view is more nuanced than such a blanket statement.