I do agree it is probably wise to avoid making a public appearance with some anonymous debating partner or interviewer who remains anonymous during the public event.
Personally I think his background (not even high school grad) and the outfit both display him as norm braking and original in thought. His accomplishments seem to support the view he is very intelligent (not some quack or cult thing) so formal credentials don’t matter for me, and the outfit doesn’t seem to undermine credibility (a bit of messenger versus message issue there I think).
Have not seen the debate (or seen transcripts) so not take on that aspect.
I agree with Kaarel about envisioning something clearly that is very distant from what is current.
But I also wonder if there is not another issue here. Whose utopia are we talking about. While I doubt I could write out a complete utopian world for me I am pretty certain that many would take exception to it being a utopia because they see things differently. So unless one is talking about some private world of their own (or small number that agree with the structures) making a utopian setting is a big public choice problem. We cannot even solve getting good policies in many cases, reaching for utopian outcomes seems a stretch.