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.
This. As great as it is to hear about sensational founders that have turned the world upside down, it is at times hard to relate to. It would be great to show the ground truth of what small companies have to go through, and having office-hours that help elucidate the thought processes to follow to make steps forward would be invaluable. The best podcast episodes I've heard (and I specifically say episodes because I don't think any show that I've heard has consistently achieved it) on this subject have just been really good at being down-to-Earth and relatable.
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.