this post was submitted on 02 Jan 2025
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ESPP is only really done in huge companies, and the terms vary too widely to be added to a common calculator. When I had one, though, I could sell right away. And the purchase price had a few different ways of being calculated, and they applied whichever was lower, so sometimes my effective discount was 25% or more.
I just cranked that shit up to the max, and sold most of it right away. I kept a small portion from each purchase as a side investment, just in case they screwed me over. I considered it my own personal severance plan, built up essentially for free.
Definitely. Mine is basically min(first_day, last_day) over a 6 month period. Able to sell right away and 15% discount.
I don't see a lot of love here for the ESPP, so I'll add my perspective. If your company is not prone to large fluctuations, then a quicksale with 15% discount is usually a good investment (if locking your money up for 6 months isn't a problem).
Even without the min of start/end, it's giving you a very good shot at 15% benefit for an average investment of ~3 months (your initial contributions are held for 6 months, but your most recent st ourchase for weeks). I don't know of any investment that can fairly confidently return near 15% in 3 months.
So long as you are confident in your stock, my strategy is:
Yes, it is taxed as short term gain this way, but your salary/other stock incentives/insurance are likely already tied to your employer, and holding it a year is riskier than quicksale