Related: if anyone hasn't listened to the first season of Gimlet's "Startup" yet, it's excellent. Former host of NPR's "Planet Money" records all the hard parts of starting his own podcast production company.

https://gimletmedia.com/episode/1-how-not-to-pitch-a-billion...

I liked season one more than season two because I felt that the Dating Ring founders were a little more guarded about their vulnerabilities and shortcomings, whereas Alex laid it all on the line. (YMMV on this opinion.)