Meanwhile, at the other companies where CEO was too sleepy to make good decisions because he was up all night helping customers configure Windows... well, we don't hear those stories, because they folded.
Edited to add: not to denigrate what he did here. He did a nice thing, and it's laudable to be a good person who helps people, whether or not it's the optimal way to spend your time.
Most of the time, the "best" possible outcome with these customers is you'll be held responsible for all their IT problems as an unpaid technician, and the worst would be they'll use patience with their entire computing setup and take it all out on you. The odds of Bob-type users damaging or even destroying a small company are vastly greater than anything else that could happen.
Think of it as beta testing or customer-focused design that you are getting paid to do.