You've made up some convenient numbers here to create a strawman. If the liquidity is 500k, that's a $17.5k tax. I'm not going to stay at a job for 10 years f

You've made up some convenient numbers here to create a strawman. If the liquidity is 500k, that's a $17.5k tax. I'm not going to stay at a job for 10 years for 30k less than market. That's a terrible decision. Most people would be looking after year 4, which is when options commonly fully vest. With my made up numbers, that's a $30.4k tax over four years versus a $17.5 tax over one year. My made up ratio is far less appealing than your made up ratio.