I was going to say he doesn't sleep but it was dangerously close to becoming a Chuck Norris fact. And I'd like to think that us Apple folk are above that.
I'm betting he'd have filters, personal assistants and probably automated responses, so the likelyhood of getting A reply, asleep or not is minimal at best lol
He also wouldn't comment on unannounced products, by nature, so I'd rather try adding him to iChat than email him
You're always going to get automated response from that or similar addresses. Although I've heard of a few rare cases where Steve himself has supposedly replied.
God knows the amount of crap he would get if he used that as a proper email address.
'I like your jenz steve. can u gt me a discount for da macbook? fnx'
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