I think the thing I'm looking for is relatability. There are many podcasts that idolize startups and founder life. The Dating Ring's podcast did the opposite and showed vulnerability. To me, that's why it was an interesting learning experience.

But to be specific - I think that small companies in make-or-break times would be most interesting. Also, everything looks easier in retrospect, but understanding the thought process and how they are balancing different options would be interesting to me.