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Should you be able to transfer trust and userbases that way? It feels like usually acquisitions trying to do this create a worse experience for users in some way or another.

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This is a good point, and transferring of trust is a very interesting concept. But while I agree that these things shouldn’t necessarily be silently transferable, I also think there should be an easy way to onboard users to the new owner/extension (if they wish to) without having them need to think about it and manually go figure it out. It shouldn’t be silent, but it also shouldn’t be a pain. Acquisitions do often make things much worse eventually for users, but negating this by complicating the process of retaining them (especially if they want to be retained) isn’t great, either.

Even if you try to keep it known, it’s easy enough to have an LLC own the extension and keys, and then sell that LLC.

And if you tie it to individuals, then an extension is transferred every time a new employee replaces an old.

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