Yeah. As much as these "if you woulda bought this stock in this year, you would be worth $xx million today" are fun to ponder, the truth of the matter is that very, very few people actually were "watching the basket very closely" would own an individual stock for more than 5 years or so. An investor who bought Amazon stock in 1994 and held to today, would have had to sit through two separate -90% drawdowns. You really think anyone "watching the basket" would actually sit through that amount of pain? Or how about when Apple was trading at $1 and change in the 1990s after Jobs left and it looked like the company was weeks away from bankruptcy....do we really think anyone who bought Apple stock in the 1980s would be able to sit through that, and hold until today. I seriously doubt it. The only people able to sit tight through these types of drawdowns are grandmas with onset dementia who forgot they actually owned the stock and their kid discovers it years later when closing out their estate after death.
Imagine some super investor, sold amazon near the top before these massive corrections and bought back near the bottom. Each time they bought back in they were able to buyback 5 times as much as before.