Is it possible?

[Sniper]

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I deffinately don't want to be a daytrader as I heard bad things about their jobs (heard it was really hard and most go broke).

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I heard the same thing about poker players!

As a daytrader, you have to be prepared to go thru the same research, practice, analyse routine that you should as a poker player.

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How much do you think I'll need to start with to accomplish what I need (ie. a few $100/month)?

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The answer to this question, depends on how much time you are willing to put in to find the right opportunities.

Your starting goal should be to average about 2-3% on equity compounded each week as a swing trader.