Is stock options worth the risk with free cash?

You have an automatic 15% return, whatever money you have that you want to invest after 401 and IRA, I would take advantage of this. Not many places you can get an automatic 15% return regardless of tax implications. My 2 cents.

every comnpany i have worked for has offered this. I have tried to game it every time and for whatever reason, it never works.

use it if you are a long believer in the company but don't buy into it as you think this is free money.

I think that you mean an ESOP, not options.

What is the vesting schedule? The people who are saying that this is "15% instant profit" are wrong, because you can't just sell the stock immediately at market price. You usually don't get full ownership of shares until a later date. In that time, share prices could drop (or rise, of course). But either way, it's not "instant profit"

It can pay off, but you have to be careful, and you should limit how much of your income you risk on this. That 15% is not guaranteed--you're still taking a risk.

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15% instant profit. You say it is doing well and if it continues to do well you can hold for a long term capital gain. Two other thoughts. If you continue to work for this company don't let the stock become a large percentage of your holdings. And, if you get worried it may go lose value down the road you can buy puts for protection (although there isn't a market for puts on all stocks).

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Not instant profit... and what are the rules about buying puts on ESOP shares? I work in healthcare so I've never had access to an ESOP. I kind of doubt that you can buy puts in a plan like this until you have full ownership of the shares...

6 month hold...before you can sell. its 1 year low is 59