First, it’s not free money, loans have to be paid back. Ok let’s use a smaller number. Bezos owns 55M shares of Amazon trading at $2,400 a share, worth $132B.

First, it’s not free money, loans have to be paid back. Ok let’s use a smaller number. Bezos owns 55M shares of Amazon trading at $2,400 a share, worth $132B. He borrows $30B for his rocket company secured by those shares. His borrowing agreement will require the shares backing those loans maintain a minimum equity value, let’s say 50%. Amazon drops over 50% to $1000 per share, dropping his shares value to $55B, breaching that agreement. His broker will immediately sell a few million shares to maintain his agreed equity ratio. What happens to Amazons shares when a few million hit the market in a short period? Amazon plunges below $500, so broker is forced to sell a few million more to try to maintain that equity, driving Amazon into the low hundreds, leading to the sale of more shares, etc, etc. Eventually they dump the remainder of his shares for under $100/each just to try to recoup the last of the $30B. He started with full control of his company, and a $130B net worth, he leaves with no shares, no control, and $30B in cash. This scenario is a little tortured, but it is likely a big reason why Bezos sells shares to raise funds for BO. Borrowing risks giving a disinterested party the right to dump your shares at a fraction of their value due to an entirely short term event.