Talk with your company’s option plan administrator and then talk with a CPA - before exercising or taking any other action. This is not advice, nor a substitut

Talk with your company’s option plan administrator and then talk with a CPA - before exercising or taking any other action. This is not advice, nor a substitute for doing those things. > But what if there isn't any liquidity for the stock? As part of maintaining an options plan, the company will usually obtain a professional valuation about every year. Google for “409a valuation” for more. https://gusto.com/blog/hiring/introduction-to-employee-equity https://gusto.com/blog/hiring/introduction-to-employee-equit... is also a decent start. > Can I defer the tax penalty until I realize gains somehow? The tax implications at exercise and at sale depend on the type of option, but where there’s tax due, no, there’s no way to defer it. This problem is why more thoughtful private companies (most notably, Pinterest) now let employees exercise options for years after they leave: https://zachholman.com/posts/fuck-your-90-day-exercise-window/ https://zachholman.com/posts/fuck-your-90-day-exercise-windo...