Merlin's podcasts, particularly Roderick on the Line and the amazing Reconcilable Differences with John Siracusa, are amongst my favourite things to listen to.
It's perhaps a more... difficult listen, but Do By Friday has a special place in my listening. It's perhaps the least about technology, but the most about people and what this sort of Wisdom is about. It's hard to recommend because it's changed so much over the years and it's mercurial over weeks and events, but it's similar to Roderick in being a very raw and rambly show, but more about Merlin and Alex.
"Preparing the way" is an absolute goldmine of an episode of Rec Diffs.