Not the op but: Gimlet is very good at creating well put together and edited stories. That seasons is very human and dives headlong into the painful (and beautiful) parts of slowly grinding and iterating toward failure. Failure from an investor perspective at least, it ends up being a non-scalable, labor intensive lifestyle business that loads of people would be proud to have built.

It was the opposite of the YC podcast: I'm a human that grew up, I went to college X, Applied to YC, Tried X, Y but Z is the one that worked. Company is great we raised money.

I think it was a combination of both. By giving them more time, they were able to revisit topics and giving new perspectives. Also, more time meant more time to get comfortable and share more intimate topics.