No, my point was that it's hard to realize a meaningful windfall as a startup employee. It wasn't that you were dealt a raw deal, or that stock as a form of pay

No, my point was that it's hard to realize a meaningful windfall as a startup employee. It wasn't that you were dealt a raw deal, or that stock as a form of payment is inherently bad. My response to you simply observed that when employees fail to convert their stock to cash as soon as possible, they are effectively investing the proceeds of a capital gain in the stock of their new employer. You mentioned that you had a deep background in markets and trading, so I'm sure you're well aware that lots of very intelligent people make irrational investment decisions. With that in mind, you might want to consider that the number of people who opted not to immediately cash out stock received in an acquisition (betting that it would be worth more in the near future) far exceeds the number of people who took all their cash from an all-cash acquisition and purchased stock in their acquirer in the open market. This is a result of perception, not logic.