There are so many examples of people in IT who are self taught I don't even know where to begin with your statement.
Many companies are willing to talk even with no degree and zero experience if you have a rare skill-set they are looking for and approach them at a hiring booth or trade show to explain your situation (not the HR filter people). Consider that for some skills (security- pentesting, RE) the degrees are practically worthless as the curriculum doesn't even come close.
However, specifically, this guy who just wants to install windows and set up a few services doesn't sound like he has a unique skill-set to leverage.