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Throughout history, even the brightest minds have fallen while trying to “buy the dip” in stock markets. Take Benjamin Graham, for example, a pioneer in value investing. After the 1929 stock market crash, he thought he found the market’s lowest point in 1931. But he guessed wrong, and his investments crumbled, leaving him bankrupt.

Another legend, Jesse Livermore, faced a similar fate—not once, but twice. Known for his bold bets, he kept putting money into stocks he thought had hit rock bottom during market downturns, only to watch his wealth disappear.

Irving Fisher, a respected American economist, saw the 1929 bubble coming. But even he couldn’t resist scooping up stocks he believed were a “bargain.” In just a few days, he lost millions, leaving him nearly broke. His mistake? Thinking strong companies could survive any market cycle, he bought in without considering how low prices could still go.

Across the ocean in Hong Kong, a well-known stock analyst, Chao Wing-chiu, faced his own hard lesson. In 1972, he correctly predicted a massive drop in the Hong Kong stock market, saving his firm from big losses. But in 1974, when the market had fallen to around 275 points, he was sure it had finally bottomed. Betting his life savings—600,000 HKD—he bought shares of Hutchison Whampoa, a blue-chip company that had plunged from 50 HKD to around 6 HKD. To his horror, the market dropped even further, and his shares sank to just 1.5 HKD. In the end, he had to sell, taking an over 85% loss.

These stories show a harsh truth: the market doesn’t spare anyone, whether it’s a famous economist or an everyday investor. Ironically, the markets later rebounded to new highs. If they hadn’t sold or been forced to cut losses, they might have come out on top. But that’s how investing often works—the market has a knack for rebounding just after you’re pushed to let go.

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