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Latest Issue

What Could Go Wrong?

September 24, 2021

I have written several letters on the theme that the best investment posture is cautious optimism. Pessimism and bearishness never get you in the game, while untamed optimism means that at some point, you’ll have a serious setback. The cautiously optimistic investor asks both, “What could go wrong?” and “What could go right?”

Dave Portnoy notwithstanding, stock prices don’t always go up. Investors got a little reminder last week when financial media suddenly had some drama to report. Then it subsided, and the market went right back up.

The latest volatility may or may not turn into something more extended. Some of the most respected market analysts are turning bearish. Still, others expect the bull market to continue. Timing is hard. Yet nothing has happened to make bear markets impossible. Stocks are overextended by many different measurements, so at some point, the bears will take control. More than a few investors aren’t ready for that possibility.

Today, I want to show you how richly valued the market is and then review some of the top risks that could force it downward. Like those sandpiles I talk about, we don’t know exactly what will trigger a collapse. We know something will do it. Sandpiles don’t grow to infinity.

But then we’re going to ask what could go right? Sandpiles don’t grow to infinity, but they can grow a lot higher for longer than many expect.

Different scenarios suggest different strategic responses. It pays to think about what could happen. It will...

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