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They're staffed by people who are well read and bring much needed nuance to a lot of discussions. I learn something fascinating every time
Indie Hackers. I've learnt SO MUCH from those interviews.
Startups for the Rest of Us also does a great job.
To a slightly lesser extent, Tropical MBA is another good one.
No other podcast has helped shape my humor and general positive outlook on life. I know that a lot of the fans of the podcasts fall into the trap of just repeating the jokes and phrases from the podcast over and over, but if you avoid doing that you'll hopefully find you humor being more cheery and light-hearted than it was before. The brothers all seem like genuinely good dudes who try their best to be as good as they can be. Their related podcasts are good too. The Adventure Zone is a great (comedy) DnD podcast (now on other TTRPGs) that they play with their dad. Despite the controversy around the other host, Cool Games Inc. was a surrealist humor podcasts about riffing on game ideas submitted by listeners. There are many more, and most of them are solid.
It covers everything. It has helped me sharpen my decision making.
It exposed me to Paul Graham, which eventually led me here [0].
It is a collection of conversations, the quality of which is unmatched by anything else I’ve come across.
[0] http://www.econtalk.org/graham-on-start-ups-innovation-and-c...