I think many such small scale middleman situations start with someone offering people a way out of thinking for themselves. Sometimes problems are not difficult to solve, but you'd have to start to think about it and make a few simple decisions and that would distract you from more important things.

So if you're the boss of a small TV station and you need some kind of IT system and your seemingly computer savy acquaintance from your cousin's birthday party comes up and says "hey man, I know how to do these things, don't waste your prescious time on it, I'm gonna do it for you!" you're hooked :-) There's trust, after all your cousin knows the guy, and even looking for someone else would be a chore. So why not? That's how it starts. (This example is not complete fantasy by the way)