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Originally Posted by Nords
One of this board's ERs got there by exercising his company's options every year, immediately selling the stock, and paying grunches of taxes.
Every year his co-workers told him he was an idiot. They were getting richer a lot faster than he was.
Then the stock price backed off about 80%. They were getting poorer a lot faster than he was.
He ER'd in the midst of the meltdown so he doesn't know if they're still calling him an idiot.
You already have your main source of income, your job, vested in that company's health. I can't think of a good reason to concentrate your holdings in company stock just because it's going up. If things ever got to the point where your job was in jeopardy, you'd probably also be suffering the double whammy of your company's cratering stock price...
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I took the corp match in my 401k because it was the best deal in the 401k, but I would trade over to an index fund as soon as it was 'qualified', because working at Megacorp for a salary, getting part of my compensation via Megacorp options and restricted stock, doing a Megacorp ESOP, and having those retirement matching funds in Megacorp, was way too much overall exposure.
* So, as I say, I moved the match in 401k right away - won't have to do that anymore; I got the same letter!
* I cash in any options (or restricted stock) as soon as vested above water, I don't look to maximize gains there by holding and hoping.
* I cash shares out of the ESPP as soon as they hit 'long term' status, but I do participate, since if the stock only goes sideways, it is still a net 10% return due to the discounted price, and for 15 years, my company stock has handily beat the market (no guarantees).
One of the things about getting these supposed bennies is that you have to work it to not be over exposed.
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