<i>Your stock options expire 10 years after they were issued or 30 days after you stop working with Clef</i><p>This market standard provision in startup employee equity agreements is probably the single biggest obstacle to realizing a gain from employee equity.<p>What it means is that when you leave your job, if you want to capture any potential upside from your options, you&#x27;re required to execute them, paying your own money for actual shares. Depending on the amount of equity you have, this may or may not be a meaningful amount of money, but it is in any case a painful decision to have to make.<p>Companies like Pinterest have done things to address this flaw; they allow employees who no longer work at the firm to retain their vested options without executing them for several years.