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I would definitely sell the company stock as soon as you can. You already have a huge investment in that company and would absolutely want to be diversified
If you plan to work yhere a while could make sense to stagger this strategy 12 months so paying long-term gains. Still sell every month just wait a year to begin.
Rising Star
TA - It is most likely your company has you paying taxes on the 15% from the start so your cost basis is in effect the FMV. Selling right away gives you free money with no risk.
Rising Star
The government thinks of the 15% discount as a taxable benefit. It is still a great deal.
Yes. Sell asap.