I have been thinking about this question for years without really understanding it.
Let's say Bob invested a small amount of money, some amount around 100 dollars, in 2013, and now it would become like 90000 dollars, which is a pretty big rise. And he can comfortably trade it out on coinbase for example to get the cash in his real bank.
However in a situation that if Bob invested 1,000,000 dollars in bitcoin in 2013, now he would theoretically have like 900,000,000 dollars. However when he tries to sell those coins to get the real money, I would imagine it can be pretty hard to find someone that is willing to pay 900,000,000 dollars to buy his coins. Also I am pretty certain coinbase and any other trading platform wouldn't allow him to sell that much coin.
In this sense, he does not really have 900,000,000 dollars and is not really that rich. So the question now becomes how much money does he really have, in the sense that he can get the cash immediately by selling the coins he have.