Great stuff.<p>I&#x27;ve personally had to deal with these decisions and know many friends who struggled with figuring out how they could possibly pay for exercising their vested shares, in some cases after they were laid off and had no choice in the timing.<p>If I were getting a job, I&#x27;d only consider offers with extended exercise windows. If they combined it with a more back-loaded vesting schedule [1], I wouldn&#x27;t mind and would evaluate that.  But dealing with the 90 day exercise window is black and white: it isn&#x27;t worth all the potential trouble and risk you can be forced to take on.<p>1: 20%&#x2F;20%&#x2F;30%&#x2F;30% instead of 25%&#x2F;25%&#x2F;25%&#x2F;25%, or 6 years instead of 4 years