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Which is Better, Investing a Little at a Time or Chucking It All In The Market? (Your Questions)

The Stacking Benjamins Show

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Employee Stock Purchase Plan, 15% Discount to Buy It?

We get a 15% discount on the purchase of our company stock. The money is taken out each pay and then invested on the first of every month at whatever the share price is minus the 15% discount. I need to hold the shares for two years for them to be considered qualified. Would it make sense to sell the company stock every time the two year holding period is up and put that money back into the employee stock purchase plan? Or am I just thinking too deep into this? Hope that all makes sense.

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