Assuming you’re in the US. Unfortunately one thing you need to consider is your options exercise window. Most startups require you to exercise them within 90 d

Assuming you’re in the US. Unfortunately one thing you need to consider is your options exercise window. Most startups require you to exercise them within 90 days of leaving the company or you lose them. When you exercise them, you need to pay AMT tax on the “spread X number of exercised shares.” (Or is this no longer true under Trump tax law? How did that saga end?) Depending on the spread and number of shares, this could be a significant price. But you have no way to liquidate the shares you receive, so you need to front a huge tax bill for receiving shares that may never liquidate. Depending on the age of the company and your share agreement, you mignt be able to sell the shares on a secondary market. Or if you have a good relationship with the founders you may be able to arrange a buy back, or possibly an extension of the exercise window. The worst case scenario is you leave, exercise your options, pay a huge tax bill, and the company never liquidates so you’re out a bunch of money. Or, some pessimistic optimists might say the worst case scenario is you leave, do NOT exercise your options within the window, and then the company DOES liquidate... All said, it’s not an easy decision and you have much more information to work with than us. My advice: don’t gamble your tax bill on weakly valued options. Whether that means you should quit or not, idk... up for you to decide.