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I am pessimistic about enough people every understanding tech environments enough to actually sustain a public conversation on philosophical principles in 2018. I think we'll see an above-the-API Straussian free speech debate and below-the-API noise zone.
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There are only 3 real challenges to free speech at the tech level a) the need for CDNs at scale b) distortions of net neutrality c) nation-state firewalls. All other claims are about social governance on private sites, where applying free speech doctrine is a stretch at best
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