For those who know more about US taxes , the Zelibor transaction is not necessarily a sale of shares ; It could be but it could also be a cashless transaction where Tom has to pay the taxes afterwards and did not sell any shares but gave up a portion of the shares . The confusion is that also a cashless transaction is reported as a sale on form 4 whereas no shares are sold. <br /> I am probably not good in explaining accurately the transaction but US tax experts should be better in explaining this. <br /> <br /> I know the same thing happened at one of my other start ups . I investigated it then and found out there was no sale. <br /> <br /> So the transaction could mean two things. <br /> <br /> 1)Tom paid for the 500000 warrants conversions and sold part of the shares which he received to pay off the taxes ( so in this case there is a sale) <br /> <br /> or <br /> 2) Tom opted for a cashless transaction where he got only a portion of the shares and gave up the remaining but then then will pay the taxes out of his own pocket on the profit made.. <br /> <br /> Both transactions are shown as a sale but in reality there is no sale in the second example . <br /> <br /> I think he can also play with the tax tariffs depending what he does with the shares but I do not remember anymore how that works. <br /> <br /> <br /> Just to say this is not abnormal at all and certainly not if he opted for option 2.. <br /> <br /> Sorry if it is not entirely clear but I am 24 years out of the profession. <br /> <br /> If I was Tom I would have done the same..