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Yeah, as I said, pseudospiritual. It's a weird approach when you've got someone who has vast amounts of technical insights and industry knowledge to engage in, effectively, philosophical circlejerking. But then if your audience lacks the technical knowledge to follow such a conversation, they might tune out. Whereas engaging in fundamentally unanswerable meta questions means your audience can feel like they've received insights and can easily follow the conversation without thinking too hard.
I have not seen anything to suggest otherwise. With that said, it helped him build an audience which helps him snag some of the most popular guests, which helps him grow his audience, which helps him get more popular guests... etc. etc. It's a successful model.
He noticed that, like Rogan, if you punch through to the top tier of podcasting you can have a self-sustaining money printing machine because important guests will seek the platform you have, and audiences will gravitate to important guests. The only risk is either 'scaring' away guests by questioning too aggressively or getting cancelled (as almost happened to Rogan) for any particular controversial moments.
Which might fully explain why he's fallen back on the softest of softball questions that don't challenge the guest nor risk wandering into a cancellation landmine.
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