Becoming wealthy and maintaining wealth are very different mindsets.

Constantly jumping from unstable stock to unstable stock is a great way to suddenly be down a great deal of money. Offsetting a 50% drop takes doubling your money afterwards and in that period you haven’t made anything so the next 50% drop puts you into a deeper hole.

As to too big to fail, the top of the market has a surprising amount of churn with many companies falling very far very quickly.