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?