[player24]

If you are still in college (and I am assuming that you are not majoring in Business), take a course in economics, finance and accounting (in that order). This, alone, will not transform you into a skilled investor, but it will put you ahead of 95% of the US population.

You have a mature/realistic attitude regarding poker - this suggests to me that you have the proper mindset to be a good investor...and that you will have a propserous career (doing whatever) which will make your $1,000 seem like pocket change in a few years. (Unfortunately, it is pocket-change...and this limits your options.)

From a financial planning point-of-view, the 'proper' place for you to start is with a diversified equity mutual fund (preferably a low cost index fund from Vanguard or Fidelity). When you build up additional assets, you can start to think about implementing a core-plus strategy whereby you own index funds with most (80+% of your assets) and you invest the remaining assets in a small semi-diversified portfolio of individual stocks or ETFs (sector funds). This is not realistic, however, until you have about $10,000 to invest.

The basic reality is that when you are 20 years old, your income and wealth creation will come almost entirely from your "day job" (because you don't have enough to invest to make much of an impact). When you are 50 years old you will, hopefully, be earning more from your investment portfolio than you will earn from your day job. So, making a mistake at your age is not very costly in the broader scheme of things.

Now, for the good news, unlike poker, where playing with play-money is detrimental to your game, you can play with play-money in the equity market and, if you are disciplined about the process, you will learn and improve. Keep a paper portfolio of individual stocks...and be honest about your entry and exit points...and track your returns. This works best when you are in competition with someone else - becuase it will keep you honest in the process and, if you have your pride on the line, it will help simulate the fear/greed of real world investing. I believe there are clubs you can join which organize this type of competition.

As far as books - try Investment Philosophies by Aswath Damodaran. During your first read, skip over the parts you don't understand.