To balance the criticism with some praise, in addition to some of the great things you have mentioned, there are two worthwhile things about the Jocko podcast that are not explicit in your post that I want to highlight.
1) Jocko embodies growth mindset.
2) Much of Jocko's discipline comes because he has trained to become comfortable experiencing discomfort. Once you've done many painful things your fear of them falls and your sense of self-efficacy rises making it easier complete future painful goals.
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When pushed on why Anthony Magnabosco is out interviewing people he responds with, "I like talking to people and finding out what they believe." True enough, but disingenuous. He presents himself as a seeker of the truth and his root goal is he is out to change minds. If the obtaining the truth was your primary motivation, street interviews is an incredibly inefficient method. The interviews come off as incredibly patronising. Questions such as, "If I gave you evidence about a biblical contradiction, and I'm not saying I do, but if I did, would you change your mind?" Of course you have a contradiction up your sleeve.
Honesty and effectiveness appear to be conflicting goals in street epistemology.