If you haven't listened to it, check out the "Startup" podcast (specifically the first season and all subsequent episodes that focus on Gimlet). The synopsis is that the host (Alex Blumberg) quits his successful job at NPR to found a podcasting company, and simultaneously starts the podcast in order to tell his own story approximately as it happens. It's fascinating to observe the genesis of the company through the eyes of its founder, starting with him pitching the idea to VCs, then hiring its first employees, and eventually growing the company to well over 100 people (and now, getting acquired by Spotify). It's a really unique and intimate perspective that would definitely appeal to the HN audience.