This is my major rub with ISO&#x27;s. Their sentence sums up the problem perfectly: &quot;You’ll still be able to buy it for $1 (and then sell it immediately for a profit of $19).&quot;<p>How am I supposed to sell a stock immediately if I have no market to sell it on because the company is private?<p>In my opinion, ISO&#x27;s drastically favor the employer. If I am unhappy and wish to leave, but have vested two years of options, I am forced to either a) throw them away after 30 days or b) purchase them and take on a potentially enormous tax burden unless I do actually have the ability to sell them immediately.<p>Additionally, by waiting to exercise at a later date I further push back the amount of time it takes to qualify for long term capital gains when selling the remaining portion of the stock.<p>I was in the exact situation I describe about three years ago when I was very unhappy and wished to look for something new. I had vested an extremely generous ISO grant that, should I have exercised it, would have bankrupted me from the tax bill. My stock was worth 100x what my strike price was, so in essence, I was the &quot;victim&quot; of the company being extremely successful. My way out of this problem was simply luck: we got bought four months after this personal crisis started.<p>I also found myself feeling like a second class citizen as time wore on. I had been a first employee and helped build the company into what it was, and I felt involved and informed with most everything going on. As time wore on, we became successful and grew substantially and I found myself in a situation where I was becoming simply a senior member of the engineering team. I was certainly not an owner, despite what my time, acceptance of risk, and vested options would imply after four years of hard work.<p>If companies really believed in the value of an ISO they would put their money where their mouth is and have a stock purchase program that helps alleviate the tax burden over time. It&#x27;s that, or allow option holders to keep their options for many years after employment terminates. As an owner, what do you want -- option holders that happily stick around even when they could leave or employees who feel they are forced to stay regardless of what happens?