The other commenters pointed out that you would have to buy those options on day one. If you're lucky enough that you're company pays for you to exercise these options than, you will absolutely be able to benefit from long term capital gains. There are two issues, however, my understanding is that the IRS will tax all of your real income the year you exercise these options based on the payment you received to buy those options. So your $50k salary will be taxed as if you made $80k since the company paid you $30k for those options. There might be a workaround using a personal LLC, but I don't know tax rules that well. Also, in practice, I've always seen employees but the options on the day of the acquisition. I worked on the corporate development team at AOL, and this was almost always the case. We actually tried to find ways to help employees, but at the time of the acquisition there's very little you can do.