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How much percent of my salary should I use to invest in company stock?
One such strategy I have heard for those who have this opportunity is to purchase the maximum allowed. When the window to sell opens, sell all of your shares and repurchase the most you can with the amount you gained (or keep an equivalent to avoid another transaction fee). This allows you to buy at a discount, and spread out the risk by investing elsewhere.  This way you are really only exposing yourself to lose money which you wouldn't have had access to without the stock discount.