We can agree to disagree. As a two time founder, I had to go through a lot of discusssions with our legal and even my own to grasp the upsides and downsides of what Elizabeth did by trading risk against a lower future tax liability. My take is that you're confusing a normal cashless transaction versus a structured loan as an executive of the company to purchase stock today to hold for a long term horizon. The risks are very real and the liability is very real. I meant this to be a way to share some specialized knowledge I have on the subject to answer why she has an actual liability and why this isn't handed out to just any employee. This isn't coming from book knowledge, but real working knowledge of this arrangement. But at the end of the day, everyone is free to do their own research. :-)