While I'm not a fan of Steve Jobs on account of him being a dick, I think he was right too often to just call it a 'lucky guess'. OSX, the MacBook, the iPod, the iPhone, and the iPad were all hugely successful. I don't think luck can get you that far.
Flipping coins suggests everybody is playing the same game with roughly equal odds.
So what is the game here? Releasing new consumer products randomly and hoping they become popular?
When Apple really broke out, PC and electronics manufacturers were still competing with one another based on spec sheets (MHz, RAM, GB, benchmarks, etc. -- whoever has more wins).
Apple went in a different direction, putting more effort into product design and user experience and marketing than its competitors. So it wasn't really a case of coin-flipping, because Apple started playing an entirely different game.
Or perhaps the coin flipping is at a higher level, e.g. trying different broad strategies to get ahead (like putting greater emphasis on design/UX)? Again, nobody else was really trying new strategies, everyone was playing the specs sheet arms race. So, in this case, there weren't enough people flipping coins to invoke the metaphor.
And let's not forget all of the work he put into tilting the odds in favor of success- such as convincing the music industry to change their business model. To say he had some sort of special genius for aesthetics isn't really fair- he also was very strategic. That may be the part the Ms. Mayer hasn't caught up to yet.
