Just to clear up, I am advocating zero-coupon convertibles. Yes, you'll have to get the corporation to cover the cost of the shares. However, convertibles will

Just to clear up, I am advocating zero-coupon convertibles. Yes, you'll have to get the corporation to cover the cost of the shares. However, convertibles will give you a tax break since they go onto balance sheets as a liability, and so they effectively give you a ~35% discount. The flip-side is that recipients will have to pay taxes on the implicit coupon payments. You really need to talk to a corporate accountant to get more details, and whether this is even a legal option for you, but definitely look into it. EDIT I misread your question. The payment becomes the responsibility of the issuing corporation, not the individual receiving the stock. That is a more clear answer :)