Most sociopaths are not successful. They generally are too self absorbed and intrinsically disregarding of society to consider what society expects of them. Hence they tend to be poor, and unwilling to expend effort to acquire wealth. A sociopath won't care about the admiration of others.
Wealth is admired only because wealth is a proxy for power. Because without the admiration of others, money isn't all that valuable. You can be poor and still be powerful- i.e. through gaining followers, rule breaking, manipulation, etc. So, it's rare for one to stumble across the opportunity to take advantage of a situation that would have them acquire wealth as well as fulfill a fascination, instead of just fulfill a fascination. To clarify, power gets you the admiration of others. Wealth makes you more powerful, but there are other ways to demonstrate power.
Something bugged me about Lou. He's portrayed as full of shit. If he is such a masterful sociopath and manipulator how come he came into success only so late in his life? Well he's portrayed as a pretty knowledgeable and manipulative guy, he would have at least had a few schemes going on that are better than metal theft and scrapping. He didn't find his niche until later. He wanted to make money but he had no skills in particular. When he discovered that he could make easy money by recording incidents he went right for it. He actually says it to Nina that he didn't find what he both liked and was good at until then. He would have at least had run a few schemes before he got into the nightcrawling such that he wouldn't be a total pauper. I always got the vibe that he was run out of town for the last shit he pulled or whatever, like this is a single chapter in his life. The ending was kinda lackluster to be honest.