Charles Simonyi would commute to the MS campus via helicopter and we all know about Paul Allen's yachts. I think it's more about it being similar to buying a second home or a nice car to normal people. I.e., you may or may not notice the expense, but it makes your life easier or more pleasant.
Are you implying that he is predisposed to blow it like a lottery winner given the fact that hasn't worked there for years and was really just the beneficiary of luck and inflated valuations?
I took the implication to be exactly the opposite of your line of thought. Given that his article is about all the work he put into Tumblr, I'd say he is not likely to have a "lottery winner" relationship with money.
