Jobs was a clear communicator who emphasized user friendly products in aesthetically pleasing boxes. If Silicon Valley wasn't the most obtuse place on earth he wouldn't have stood out nearly as hard.

I think youre underestimating the effort necessary to simplify.

Most humans I have encountered, particularly the book smart ones, are absolutely horrible at this. It really takes a concerted desire to be disciplined and focused to do it well. Unsurprisingly Jobs spoke a lot about the idea of focus and being disciplined, as being the foundation for his success.