I enjoy the relaxed, maybe natural, mood of his conversations. There's no apparent structure other than two people talking, although I'm sure Gruber brings ideas about what he wants to discuss with the guest as we all do; maybe that have been topics loosely agreed upon with the guest but aren't necessarily forced. He probably reverse-engineers episode markers from whatever was talked about in each podcast.
Another thing that caught my attention is the Sponsor blocks. He introduces these ad sections irregularly from episode to episode, without an apparent structure.
I remember the old days when I discovered Daring Fireball—Gruber's blog. The site looks the same today as it did back then and continues to serve its function perfectly. The blog's Weekly Sponsorship program costs $10,500 a week1 and is usually sold out a few weeks in advance. "[T]he only way to promote your product or service specifically to Daring Fireball’s audience of Mac nerds, designers, nitpickers, perfectionists, and connoisseurs of fine sarcasm."
I wonder how expensive podcast placements on The Talk Show are.
I'm used to shows like Tim Ferris or Lex Fridman's, where conversations are often geared toward specific questions, and to my show—Getting Simple—which drags from the style of my favorite and most-listened podcasts out there.
Indeed, my home page borrows from his way of linking to external sources directly from the post title, creating a permalink with the post date (while he does so with the star symbol), and linking to that permalink from the title when the post doesn't contain an external link.
I guess it's only possible to make a living out of blogging and podcasting when you accrue such an audience; 80,000–100,000 weekday page views, 2.5 million monthly, and over 200,000 RSS feed subscribers.