I&#x27;ve done it, but my options agreement with the company put such restrictions on trading the stock that it couldn&#x27;t have happened without the very willing participation&#x2F;assistance of the execs.  I don&#x27;t actually understand all of the details, but I know there were issues with both right of first refusal and also prohibitions on private stock transactions that the company had to explicitly waive.  In the end, I just had to trust a lawyer to reassure me that in the end, I would no longer have any options but I would have a whole bunch of cash, because all the mechanics were both over my head and arranged by someone else.