You can draw a straight line through iPod -> iTunes Store -> iPhone -> App Store -> iPad -> Apple Watch. Even though the vision was a little blurry with regards to how powerful mobile devices would get and thus how the smart phone would overtake the PC for revenue, it still holds up in the way these products are executed and integrated. Frankly, the only company that is really competing effectively with this 15-year-old strategy is Google, because they have cloud services chops that Apple has struggled with, but despite being dominant in that area, it's still just good enough to put them on par because their UX, integrated industrial design, supply chain management, and marketing still pale in comparison to Apple.
Just because it wasn't immediately obvious to the world that the iPod would succeed doesn't mean that the vision wasn't there or that it was just dumb luck. Obviously there is a huge amount of luck in terms of circumstances that fuel every large company, but I find it really annoying when people are so dismissive of good execution with this type of hand-wavy rhetoric.
That's not really the case though. As Jobs outlined it in that video, the Digital Hub strategy was to sell Macintoshes by positioning them as something you could dock your consumer-electronics gadgets, mostly from third parties, into. It was a plan to sell hubs, not spokes. This strategy had limited viability for Apple, because a typical consumer wasn't likely to think "I've just bought this $500 camcorder, so now I need to spend twice that or more on a Mac in order to offload and edit the video". If they were going to use any computer as the digital hub for their camcorder, it was probably going to be their Windows PC. That's probably why iTunes for Windows was such a difficult and long-drawn-out decision for Jobs: because it was a decision to mostly abandon the Digital Hub approach in favour of selling more of the spokes. Then Apple's slow and initially reluctant embrace of the "post-PC era" with over-the-air iDevice updates and cloud storage to partly displace iTunes means that it's increasingly taking nearly the opposite of Jobs' 2001 stance: "We're clearly migrating away from the PC as the centrepiece" and "We don't think of it in terms of the PC business anymore" are things that Tim Cook could say today without really startling anyone.
I imagine with each design decision they asked just two questions "will it make the product more awesome" and "can we afford it".
I wonder if stock holders knew Apple was risking that much on a project that wasn't even a computer.
They fixed all those problems later versions, but the initial device was underwhelming to a lot of people.
From personal anecdote i think i first heard about iPod when people started chatting about what those white earbuds some artist had been spotted using.
And i sure as hell don't think Apple was in the position to pay them to use the iPod publically.