Take [0], where John Allison of BB&T discusses his business philosophy, and as an aside mentions that his bank doesn’t issue negative amortization mortgages (a cause of the recession) in 2007.
Or [1], where Michael Lewis discusses Moneyball and The Blind Side.
Or [2], where Christopher Hitchens discusses George Orwell.
Or [3], where Paul Graham talks about Hackers and Painters.
EconTalk has something for everyone.
[0] http://www.econtalk.org/allison-on-strategy-profits-and-self...
[1] http://www.econtalk.org/michael-lewis-on-the-hidden-economic...
[2] http://www.econtalk.org/hitchens-on-orwell/
[3] http://www.econtalk.org/graham-on-start-ups-innovation-and-c...
Here's a list of one guy's ranked favorites: https://docs.google.com/document/d/1TejVbFNWkAaqRYQ4UaZfwNDK...
Even to the extent that guest are oblivious to real world concerns (or alternate Ivory tower theories, which also happens sometimes), Russ Roberts is pretty good at respectfully challenging guests, and I feel like I at least understand where the guest is coming from.
Early in my career, I was a regular listener to three tech podcasts: Java Posse, StackOverflow podcast, and Software Engineering Radio. All three were valuable to my career in different ways, but EconTalk has most affected the way I think.
For those who aren't familiar, the host of EconTalk is a professor of economics, so many of his conversations revolve around the world of economics, but since economics touches a lot of things, he ends up talking to a diverse group of people. He is very good at admitting his own bias on the one hand, and then argue against it on the other hand.
Also, I found History of Rome valuable - it's an interesting story, but it also helps cure the chronological snobbery of assuming that our times are vastly different from others.