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Because he's trying to become a regulated investment bank. You cant spout off anti fed rhetoric now. Why would a bank support self custody? Saylor is playing the game and politricking to get the banking license. Its no longer hold and control your own wealth. Now he will say let me take care of that for you. Self custody and multi sig is too difficult. Funny thing is that we may soon seen FDIC insured bitcoin.
It's nice to have 99.9% of the freedom instead of 99.9% of "the money"(TM). Make your own wallets. And, in the case of hardware wallets, know that there are fully open source examples. MSTR shares are the ones going to be seized, not Bitcoin. Don't trust the banks. Don't trust the fearmongering. Don't trust not to trust. Don't trust, verify.
His bet is that he can lever against an ever failing dollar, the stock price of his company depends on it at this point. What he is not able to deal with are angered central bankers who decide they need to go after him. The central bankers can't have Bitcoin used as a currency, this takes away their power.