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.