The market makers are the house. They don't lose, and most of the time it means selling overpriced shares to suckers in the retail space. They influence the direction and trading range every day, so you are always playing against the house instead of other retail investors. The house has far more leverage than you or I ever will, so they will win nearly every time.
This is largely dependent upon what he's holding. If he is holding bank stocks, their valuations will never reach the peak in 2007 again. EVER. There are thousands of stocks that will NEVER see 2007 levels again. Just look at the companies that recovered after the dot com bust in 2001. You just WON'T make money on stocks that are now more likely to fall or trade sideways than appreciate in value.
You're wrong. It's 31 days, and when you add 48 hours for the stock to "settle" in your account in most major brokerages, you arrive at 35 days. Try to harvest a tax loss and see what happens if you don't take the settlement period into account with your timing. It's an expensive mistake that you'll only make once.
35 days is the de-facto time you are guaranteed not to be robbed of the tax loss sale. Once again, this is a rookie mistake.
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