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theoriginalharbinger t1_iydtnnt wrote

If you have a lookback provision, 100% do this.

The only two risks are - if you sell immediately - the following:

  1. Stock falls of a cliff between when you purchase the shares and when they settle and are made available for sale;

  2. You have a theoretical opportunity cost that exceeds the 15% discount

For an example of (2), if you have CC debt at 30% interest, you'd probably be better off just paying it down than contributing to an ESPP; while the ESPP does offer a significant gain, if you're indebted elsewhere this may be a problem.

You're also subject to the 25k annual cap.

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helpdesk-26 OP t1_iydttno wrote

The price is the lower of the price on Jan 1 or June 30 - the discount. It’s all purchased July 1.

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theoriginalharbinger t1_iyduobm wrote

Right. The small risk you run is that the strike price on June 30 is something high (for easy math, say it's $100) and then your CEO gets discovered on July 1 to be snorting coke off his CFO's belly while the board is lighting cigars with sawbucks and watching and the stock price tumbles to $50 while your shares are not yet sellable in your account because they haven't settled yet.

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helpdesk-26 OP t1_iydvfjo wrote

Makes sense. It’s an extremely stable stock so I’m assuming it’s low risk.

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