The question of whether there was a grand plan is certainly an interesting one, but it seems unlikely that in 1998 there was a big whiteboard in Cupertino with

The question of whether there was a grand plan is certainly an interesting one, but it seems unlikely that in 1998 there was a big whiteboard in Cupertino with "iMac -> iTunes -> iPod -> iPhone -> iPad -> profit!" written on it. But some of those internal steps may have been planned. iTunes came out about 10 months before the iPod did, but obviously the iPod was in development for longer than that. I wonder if iTunes was specifically designed to be the interface between the computer and the iPod? Or if it was just part of a "digital hub" strategy (this was a term Apple bandied about a lot in the early '00s) that was envisioned as being focused on the Mac and that only pivoted when it became clear what a runaway success the iPod was.