You can't discount that most companies fail though, you'd expect the majority of options to go unexercised. Edited to expand a bit: Shares are ugly and annoyi

You can't discount that most companies fail though, you'd expect the majority of options to go unexercised. Edited to expand a bit: Shares are ugly and annoying and cap tables are broken but it so rarely matters. Things should obviously be better and cleaner and more organized but since so few companies return anything to anyone besides the preferred shareholders, I'm not sure the 'cost' of this disorganization is very high. Seems like another case similar to the uncovered call option description of 'technical debt'. By avoiding the time and effort of energy associated with cap table management, companies can focus on things that add value and count on lawyers to sort it out when the work will provide value -- fundraising / M&A. There's a point to be made about the lack of a signal here too, if all companies are bad, then no company looks worse for meeting that expectation.