It's exceedingly rare for founders to be allowed to take money off the table during these large rounds. According to leaked emails from Sony, investors balked

It's exceedingly rare for founders to be allowed to take money off the table during these large rounds. According to leaked emails from Sony, investors balked when Evan Spiegel of Snapchat tried to unload $40M in personal shares - just after he had turned down a $3B offer from Facebook. The founder of Twitch wanted to take some money off the table at a ~$200M valuation nine months before it was sold to Amazon for $970M, and he was also rejected [1]. If they aren't giving cash to founders of companies like Snapchat and Twitch, there likely aren't a whole lot of other people that are getting it either. [1] http://justinkan.com/the-99-percent http://justinkan.com/the-99-percent