You should both check out WNYC'S "On The Media." It's NPR style, but every interview you hear is a 40-60-120 minute interview that's been boiled down to 8-10 min for the show. It's truly bespoke radio in that way, so they get to cover the issues at the core of something. It's my favorite show week to week.
..."professional hoop-jumper" ...He means being a kid?
There's a self-importance and arrogance to all of this that really comes through from this type of rhetor. I think the imposter syndrome might not be that much of a syndrome in the case of far too many startup teams sadly.