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My hope was that there was a good comprehensive resource in to gaining this type of knowledge, or a well known collection of resources.
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Investopedia
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$1000 would just be a "getting my feet wet" type of investment. I wouldn't die if a lost it,
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Bad Idea. Investing isn't like playing poker, in that you can deposit $100 on Party, play $.50-$1 to "get your feet wet," and then start studying once you get the rules and mechanics down. You need to learn how to invest before you put a nickle into any kind of investment. If you don't want to learn about the finer points of investing, that's fine. CD's, index funds, and several other methods allow you to invest conservatively with virtually no knowledge of what you're doing. You should never have a "if I lost it" mentality. A loss of an investment should only be the result of an unforeseen occurence, not a gamble that didn't pay off.
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I've glanced through some resources and they seem to assume you know how certain markets work already
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I still don't know exactly what you mean here. Do you want to know the detailed economic forces that drive all markets? Because that's a discussion I'm in no way qualified to participate in. If you have a few specific questions about the simple mechanics behind certain types of investments, post them and I (and a few others I'm sure) will try to answer them.