This only works if the one loaning you money decides that your collateral is worth the risk. You too can borrow money against the value of your home (which again, you would have to sell and report the income). Wouldn't this also assume that the loaner saying, "Hey, I noticed your rich, here is some free money,don't worry about paying it back, just float me some interest." In general, loan agents aren't paid on how much money they can give out for free. As far as the interest on the loan vs. the capital gains, that really makes no sense. Your still paying back the loan, with interest (which you can write off). The fact that you used company stocks or livestock as collateral is irrelevant.