Saylor is making negative public statements about crypto anarchists, but https://www.hope.com/resources still lists Soverign Individual, Murray Rothbard, and Hans Herman Hoppe. I know he's actually read these books because I've heard him talk about them.

I see three possible scenarios now. Listed in order of likelihood. 

1. He understands libertarian theory, but has become enamored with power and wants to join the high finance club. He's more interested in compromising with them than he is with a genuine renaissance. (Likely)

2. He's somehow compromised through blackmail or some other conflict of interest and has yet to be able to break free from that. (Possible)

3. He is an exremely talented actor as well as an investor and CEO. He didn't mean anything he said in his recent interviews and is playing coy for his advantage. (Very unlikely)