Personal favorites:

Conversations with Tyler - Tobi Lütke on Creating Shopify for Americans as a German in Canada (Ep. 221). I found Tobi's viewpoint as a European who has set up a business in North America to be particularly interesting and unique.

The Rest is Politics - Trump Returns: What Now? I was not pleased by the result but this podcast helped me process it and understand some of the reasoning behind it.

The Social Radars - Dan Siroker. First time coming across the Optimizely story and found it a fascinating one.

What's on your list?