Videonics DirectED, a video editing system, conveniently loaded its software from... VHS tape. Here are some details: https://twitter.com/foone/status/1325945997160165376 and apparently you can still buy it well-preserved as new old stock, complete with the VHS software tape: https://www.ebay.com/itm/124380109086

A little less crazy and more straightforward (software on audio tape was super common after all): Radio stations and vinyl discs that transmitted programs to the microcomputers of the time (C64, TRS-80 etc.) have quite a long tradition. Some examples:

http://www.trs-80.org/basic-over-shortwave/ https://www.youtube.com/watch?v=6_CZpFqvDQo&t=2s

Not paid for programming but essentially the same tech: VHS games used to encode data in exotic ways so that the content was both viewable on regular TVs with a regular VHS player, but also had some kind of playable content.

https://youtu.be/WI133HNGNfk

Not quite paid programming, but Scientific Atlanta had a Broadcast File System that would send data to set top boxes over coax QAM channels used for digital TV. It would loop through all the content on the "carousel" repeatedly so all the boxes connected to that head end would eventually see the updates.