Like Melbustus said, the main obstacle to much of the "2.0" stuff is regulatory as opposed to technological. The useful "2.0" features will be implemented on top of bitcoin when the regulatory picture is more clear, the ecosystem has matured, and there's actual demand for these products (as opposed to what IMO is speculative demand designed to pump an alternative blockchain).
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1) The entities that issue shares onto the platform very likely need to comply with SEC regs. You can ask Erik Voorhees about that.
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Yes, absolutely. I find debates about the legality of 2.0 tech fascinating: many people have strong opinions, but few seem interested in digging into the
actual laws as they are presently written.
For example, perusing the
BC Corporations Act (which applies where I live) it becomes clear that a company can't have anonymous shareholders. Shareholder name and addresses must be logged in the company's share registry.
This makes perfect sense given current tax/corporate laws: for example, the company needs to determine % foreign ownership for tax purposes, it needs to know
how many shareholders it has as that affects certain reporting requirements, etc, etc.
So no anonymous shareholders, which complicates the use of blockchain-based share certificates. "Bearer shares" are not lawful in any jurisdiction that I'm aware of.
This is just one example. I suspect anonymous asset-backed tokens are unlawful as well (and is probably the reason we haven't seen Brock Pierce's "real coins"). Download the applicable laws in any relevant jurisdiction, and the difficulty in navigating them should become clear.
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I spent one evening going through the BC Corporations Act and made notes here about ways I thought one could issue blockchain-based share certificates and adhere to the existing laws, if anyone's interested.