I like how Pod Save America (which is quite rife with ads) riffs on their advertisers and has amusing side-commentary on their advertisements that are in-line with current events.
In a sense this is arguably what podcast advertisers are paying for, these kind of “amusing side-commentaries” in podcast ads tread a grey area between advertisement and paid personal endorsement. The best podcasters are relatively self-aware of this grey area and avoid accepting ad money from products they don’t personally believe are worthwhile to their listeners. Podcast advertisers are effectively paying to borrow the good will that often exists between a podcaster and their fans to try and sell products/services, which I suspect must have a pretty robust conversion rate, judging by the speed at which podcast advertising has grown.
The relationship between listeners and podcasts hosts is surprisingly intimate for a broadcast medium.
True, and Lovett is generally pretty hilarious, but... then the ad breaks are 5 minutes long... If I'm able (i.e., not driving), I tend to just skip them.
It breaks out of the mold of a pure ad.