Really simple to prove you wrong.

Ask yourself - why would he do that? There is no reason to do that if it's not worth that. Why would be buy high (financing at much higher prices) and sell low (selling at todays market price with 0 premium) and manage to still become a billionaire?

I've mentioned this before, but the stock price is not just a number on your screen (unless you're a trader). It's the valuation of a business, and is representative of how much the underlying assets of the business is worth as well as how much cashflow it will present in the future. $1-$2 is not representative of the value of the company, so he simply will not sell it for that much.

Ask yourself, if you were given a brand new Mercedes for $1. Would you sell it for $10 because you'd make 10x your money? How about $100 because you'd make 100x your money? If you would do either of those deals, you should probably give someone else power of attorney for all financial decision making from now on.