[spazzyfry123]

Originally Posted by smyles

Are you fully vested? Would suck watching it fall and not being able to do anything about it. Think AOL, Kodak, etc.

Fully vested.

Originally Posted by c1pher

On the surface an ESPP can sound risky or a good deal. As an employee, you may or may not have a sense of how well your company is doing. And by investing in a single company, you are losing the advantage of diversification. I have been in these programs for two defense companies and have done very well on them....in addition to other investments. However, I’m fairly senior and have a better understanding of what’s going on with a company than a typical employee may be. This gives you more confidence to know you will get a solid or higher than average return. For example, a regular employee will not be aware of an impending merger or acquisition. I’m those instances senior business members can be restricted from buying or selling company stock during those periods.

Originally Posted by corn18

When can you sell? If you can sell immediately, then the 15% discount price is a no brainer. Buy $20k every year. If there is a holding period, then only you can decide how much you want to risk.

When my company ESPP was 15% discount every 6 months with no holding period, I would buy the max and sell it the day it hit my account. That was easy money. Now it's @ 5% with no holding period and I don't bother. After paying 50% marginal tax, there isn't much meat left on the bone for the trouble.

Senior enough to understand what’s going on, but not “too” senior in that I have a hold period and considered insider trading. Once it’s in my account (purchased quarterly from funds accumulated through the bi-weekly checks at up to 10%), I can sell it off immediately.

Originally Posted by AlpineWhite_SJ

Hard to answer not knowing the company, but yes, I generally recommend maxing this out if you can. Unless your company has crazy swings, you're getting an easy 15%.

But the real advantage you should look into is how they set the price and whether it locks for a period. That's where you can really make some money because you can get a two year lock on a low price even if the stock has risen significantly.

Let's say your subscription price is $50 and it's good for two years. Stock goes up to $100 you're still buying at 15% off the $50. On the other hand, if it went down to $45, your next buy would move to that new lower price and it'd be 15% off that.

If you believe in the company and it's executing well, you can make some serious cash. I've got some ESPP shares that were at $12 and currently trade around $350.

No price locks that I understand. Buy-in is 15% less than the market average of the quarter. Annual dividends are paid in additional shares (which is effectively 5% of shares held).

Leading company in our respective industry with over a century of being in business. Stability seems almost certain. Math tells me to max it out and sell off after the dividend payout to then start it over again each year, but what’s the catch? That’s why I tossed 3% at it - see what happens after a couple quarters without risking too much. It can’t be that straightforward.