[chrdlu]

This is the main dilemma for startup employees across the board! The ideal situation is not leaving the company until after an IPO or M&A after which your options/shares will be liquid. The purpose of the options is to keep you at the company by locking you into "golden handcuffs" and raises the cost of changing companies.

If the company is successful, the money you will make can be life changing. If the company fails, then you lose most if not all of your investment.

However, in the last few years, many solutions have appeared to address this binary situation. I work at the ESO Fund and we try to provide a middle ground. We provide money to exercise and any potential taxes in exchange for a piece of the upside and we do this on a completely non-recourse basis (meaning you don't have to pay us back if the company fails). Our deals are structured to give you the majority of the upside without having to invest your own personal money!

Feel free to reach out if you have any more questions!