I like the general idea, anarchir. The implementation could be better (i.e. pixelation), but who cares. Here are a few other nitpicks I can offer:
In my interpretation, it shows
the three sectors of the economy: the service sector (businessman), the industry (gear & ranch), and the "natural sector" (cowboy). Each sector is idealized by its greatest representatives: the businessman represents worker independence (i.e. owning your "means of production" and working for yourself), the gear & ranch represents robotization (human beings shouldn't be doing the dirty work by hand), and the cowboy represents independence over nature (i.e. being in control of your local food supply, good stewardship of private property, as well as the capacity for self-defense). I'd like to think that the cowboy and the businessman are the same guy: day job vs weekend hobby.
The center needs some rethinking, because it's all in the gold (capitalist) portion, as if the cowboy is doing all the industrial work and the businessman is "exploiting" him. I'd put the gear & ranch in the very center, spanning both colors. The representation of industry is also a bit outdated, how about adding something like a microchip, the nuclear symbol, and/or a DNA helix as well?
I have mixed feelings about one side being upside-down, because it creates symbolical asymmetry, since flying a flag upside-down is a sign of distress - some might think the businessman is shown to be the bad guy. Of course there are no rules on how the black'n'gold symbolism is to be presented, on a hanging cloth or on a billboard that rotates like a propeller. Also, it's traditional to have good guys face the center of the picture - my mom was working for a small college newspaper in the Soviet Union once, and they almost got into a big heap of trouble for putting Lenin's silhouette facing the edge of the page, as if instead of approvingly overlooking the page he's turning away from it and staring into oblivion.
So I'd move the cowboy and the businessman from the corners and put them on the same level as the gear & ranch, both right side up, facing each-other in friendship.