The first 50 episodes of the Indie Hackers podcast had a big influence on how I approached bootstrapping. The episodes that stood out in particular are:

- Pieter Levels: https://www.indiehackers.com/podcast/043-pieter-levels-of-no...

- Tracy Osborn: https://www.indiehackers.com/podcast/029-tracy-osborn-of-hel...

Josh Pigford (who sold Baremetrics for $4M) has also documented all of his failed ventures:

https://joshpigford.com/projects