People get stuck when they realize that success costs way more than they expected. They have to trade things they weren’t originally willing to trade in order to keep progressing. And that’s okay. You can say “this is enough.” You won for you. That’s the point.

We're in a bubble. We have artificially low interest rates. We have a stock market that, frankly, has been good to me, but I still hate to see what's happening. We have a stock market that is so bloated. Be careful of a bubble because what you've seen in the past might be small potatoes compared to what happens. So be very, very careful.

Over the past 15 years, both Internet stocks and houses have demonstrated the extraordinary excesses that can be created by combining an initially sensible thesis with well-publicized rising prices. In these bubbles, an army of originally skeptical investors succumbed to the “proof” delivered by the market, and the pool of buyers — for a time — expanded sufficiently to keep the bandwagon rolling. But bubbles blown large enough inevitably pop. And then the old proverb is confirmed once again: “What the wise man does in the beginning, the fool does in the end.

No wonder people make money in the real estate market and lose money in the stock market. They spend months choosing their houses, and minutes choosing their stocks. In fact, they spend more time shopping for a good microwave oven than shopping for a good investment.

First, do not be invested in the market all the time. There are many times when I have been completely in cash, especially when I was unsure of the direction of the market and waiting for a confirmation of the next move. Second, it is the change in the major trend that hurts most speculators.

Double, treble, quadruple bubble, watch the stock market get into trouble...

I visualized my grief if the stock market went way up and I wasn’t in it — or if it went way down and I was completely in it. My intention was to minimize my future regret. So I split my contributions 50/50 between bonds and equities.

Of course, sitting tight is a challenge for this generation! As a society, we’re wired for instant rewards, and waiting for the assets in our Security Bucket to increase in value can initially feel like watching grass grow. And that’s why we get tempted into putting too much of our money into the next bucket, Risk/Growth.

But a pin lies in wait for every bubble. And when the two eventually meet, a new wave of investors learns some very old lessons: First, many in Wall Street — a community in which quality control is not prized — will sell investors anything they will buy. Second, speculation is most dangerous when it looks easiest.

The whole trick in investing is: “How do I keep from losing everything?” If you use the 200-day moving average rule, then you get out.

You can also lose everything you’ve saved and invested. So whatever you put in your Risk/Growth Bucket, you have to be prepared to lose a portion or even all of it if you don’t have protective measures in place.

My old boss, Ben Graham, told me very early on you get more trouble with a good idea than a bad idea, because the good idea works. I mean, it's a good idea to buy a home, for example. And then people go crazy sometimes. The good idea works, and it works, and it works. Stocks work out better than bonds most of the time. And, after a while, people forget that there were some other limiting conditions. With Edgar Lawrence Smith's book, it was that when bonds yield the same as stocks — which was the case then — the stocks are going to outperform because they have this retained earnings. So stocks started going up in the Twenties and all of a sudden they were selling at 5 or 6 times the prices as when they bought the book. And the original correct perception on his part had experienced changing conditions, but people ... got their confirmation through stock prices. That's what happens in bull markets. People start out thinking stocks are cheap, and then they start thinking stocks have gone up. And, a stock can be a good buy or a bad buy. A bond can be a good buy or a bad buy. It depends on price.

A war takes place; an earthquake occurs; a flood of a magnitude not seen in a hundred years washes over the land; a cartel falls apart; oil prices quadruple; tax laws change, and the market in which you had an open position, or even hedged, moves in a magnitude not only unforeseen, but totally outside past models. They always do. You are in trouble.

When people tell you that this
venerable firm or private investor invested X millions of dollars in
that entity and that it is a good investment, be skeptical and stay open
to the option of running as far as you can in the opposite direction.
We have all seen the biggest names on Wall Street along with the
largest sovereign wealth funds on the planet make the dumbest investments
ever made. Do your due diligence; ask the right questions, and
most important, check out the character of the people involved unless
you want to end up being prey to another master of the universe à
la Bernie Madoff.