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 Language like at 20:55

Crypto anarchists not regulated, don’t acknowledge government, don’t acknowledge taxes and don’t acknowledge reporting requirements.

Is very offensive and belittling,

Also denying that gold was seized in 1933, or that governments don’t come after assets, was very dishonest.

Also not supporting self custody for those that can is very, very bad.

It is clear from this interview that he is opposed to Bitcoins core goal of separating the state from money. He believes Bitcoin will provide the state with foundations, just as Trump does.

Trump doesn’t know any better, he can be forgiven. Saylor knows better. 
 I didn't pay it a lot of attention, so I respect y'alls opinions, but are you saying crypto anarchists acknowledge governments / regulation / taxes / reporting? And why does he have to support self custody? As long as he doesn't campaign against it, fine with me. Other people can support self custody. 

In my opinion, the government is a user of money as well. It's just the privileges that governments abuse that Bitcoin could take away.  
 Bitcoin was specifically introduced to prevent the 2008 financial crises. The message is hard coded in the Genesis block:

"The Times 03/Jan/2009 Chancellor on brink of second bailout for banks"

The purpose of Bitcoin is to separate the state from money and remove the power central banks have.

That is a strong message which I would not expect him to say out loud.

But to say out loud statements that oppose those goals and insult the community that create it are unforgivable.

He attacked and was making statements against Bitcoin.
 
 Okay, I seen a longer video and I get what you're saying now. The "paranoid" part about hardware wallets / guns salesmen being fear mongerers was naive and wrong.  
 He doesn't have to be pro Bitcoin in public, but he can't insult it or the community in public. 
 He can, cause he did, but the backlash is justified.