Why did you continue to buy generation after generation of a product that you felt was sub-par?

The same friend kept buying the Jawbone and telling me how great they were! I've now converted him to AirPods as well.

But why airpods and not one of the countless other bluetooth headphones? There are so many alternatives with equal or better sound for a cheaper price. Or is the design the appealing factor for many people?

For my, it was my trust in the Apple brand that airpods would work as advertised and be easy to use.

I now use carry and use them everyday and listen to much more music/spoken content than I ever did before. Many times I use them over my QC35s.

For me the quality and consistency of the pairing has been the key advantage.

To be honest, bluetooth was not that reliable until recently. With the new 4.x versions of Bluetooth, things are a lot more stable with audio devices. So I wouldn't blame Jawbone alone.

Perhaps my memory fails me but weren't Jawbone one of the pioneers in bluetooth?

I was in the same boat - the headsets were never really good enough, but they were way better than any other option out there. Until the AirPods...

My Jambox is a frequent pain in my butt, and I only ever use it with one device.

Removing ALL voice files on the Jambox helps with reliability.

(Just keep hard and soft resetting until the voices disappear.)