buying options in a privately-held company
brk: See other advice above, ie: it's very unlikely that you can actually execute this arrangement.Supposing that you can, however, I would recommend that you either purchase shares outright, or now.  Stock is not really a good thing to have joint ownership of (excepting cases of spouses, etc.).I would never "purchase" (I'm using the term loosely here) stock that I didn't have ultimate control over.  If the ex-employee wants to make some money, you could agree to purchase his options at a price between their current value and his strike price.If you don't follow the above, you'd need a fairly rigid contract outlining how and when either party could force the sale of the stock (price, criteria, RFR, etc.).