As long as I'm riffing on the difficulty of podcast discovery, I thought I'd post some recommendations, sorted by the very scientific algorithm "My eclectic interests optimized for things you probably wouldn't have been recommended before."
Here we go:
Real estate investing, mostly for smaller landlords as opposed to e.g. commercial REITs. Lots of storytelling and scrappy entrepreneurship.
Tech listeners will enjoy tales of folks cobbling systems together w/o software + get SaaS ideas.
The text is about the game of poker (deeply) but also about how the people who play the game of poker think about things like risk, career development, their various fields, etc etc.
Clinical psychologist Dr. Sherry Walling on founder mental health, with recurring themes about family and relationships featuring as a standout to me. Also, the Founder Origin Stories subseries is the best ethnography work on bootstrappers.