I often wonder how he supports himself. Either he lives on little and spends his time making cool stuff and helping kids program, or he's actually a Rockerfeller.
Alternatively, he holds down a day job, and is just so prolific that it seems like he just makes shoes and hpricot all the time.
Supporting yourself and still coding a lot of cool stuff to give away isn't really that hard. There are plenty of service, light tech support, or even desk jobs which only require a few hours a day worth of real concentration, and leave you alone with your thoughts the rest of the time.
Covering rent + groceries in some sleepy midwest town with decent broadband is do-able on minimum wage, if you don't mint having a small apartment and older computers.
The challenge is in living the kind of lifestyle that most HN readers have or aspire to: living in S.F., going out to nice restaurants + clubs with your hip, hacker friends, owning multiple nice computers + tech toys, and flying to conferences and vacations all over the world several times a year.
I worked with him for about a year several years ago (before he got into Ruby). For the most part, his personality is just as you see him in his writing. He's very intelligent, which probably accounts to some degree for his prolific coding. I really doubt he's wealthy, though. He's too anti-establishment for much of that. Definitely a genuinely good guy, though.
He's so prolific that for a while I wondered if _why wasn't really a collection of people. But, he's just so consistently odd and unique (in a good way) that it's hard to imagine that there could be more than one _why.
(Although, I wonder how hard it would be to use markov chains to generate _why-like rambling rants)
Hello? I thought "Zed is dead", but now really, all that needed was an overt HCE reference to boost such a fine diatribe into the literary flame sphere.
