To be clear, he's never had an exit and I don't see one for Twitter or Square anytime soon. There's hundreds of millions (billions?) of dollars of VC cash sitting in those investments without getting a return.
Meanwhile, Square announced in April it was trying to raise $250m at a $4B valuation (Source: http://techcrunch.com/2012/04/25/square-now-processing-5b-in...). They just finished that raise with $200m at a $3.25B valuation. That's a huge miss for such a big company. They're also burning cash at an enormous rate (see http://i.imgur.com/b1Sm9.png - leaked slide).
So just remember that he may be an amazing person, but the PR engine surrounding him so distorts everything that we hear that at least for me, I've stopped paying attention entirely.
PS: Don't even get me started on how much the press entirely screwed up the Starbucks partnership reporting. It's a tiny marketing ploy is all.
PPS: This is mostly just my opinion obviously. I prefer businesses to focus on creating a viable, long-term business instead of a clever marketing machine with an unsustainable revenue model.