As you say, one possibility is to exercise your options, then sell the shares on the secondary market before IPO. It's worth at least talking to a company like

As you say, one possibility is to exercise your options, then sell the shares on the secondary market before IPO. It's worth at least talking to a company like Sharespost about whether those shares would be salable. They can give you an idea of what other employees have sold their pre-IPO shares for, and whether your employer allowed the sale. I also second the advice about at least waiting until January 1, so you have another year to let the stock mature. And if ever there were a time to talk to a tax accountant, that time is now.