>> But I don't know what he could be up to.
A couple of things come to mind. Not necessarily nefarious.
Firstly, I remember watching a TED video[1] by Steven's brother Conrad, which was passionate about using computers for teaching Mathematics. Perhaps this Pi initiative is less commercial than philanthropic and was initiated by Conrad.
Secondly, if you look at Wolfram's own blog post[2] on the Pi release of Mathematica, he talks about his new Wolfram Language far more than about the Pi platform. I suspect Steven Wolfram is as successful a business-person as he needs to be now, but he intends for his legacy to be as a revolutionary. I don't know this for sure, but Wolfram Language seems to be a beachhead for NKS in usable form.
I also speculate the common Britishness of these two organisations might have helped move this project forward.
[1]http://www.ted.com/talks/conrad_wolfram_teaching_kids_real_m... [2]http://blog.wolfram.com/2013/11/21/putting-the-wolfram-langu...