This Mistake Could Cost You a Fortune

Just when I thought it couldn't get any worse ... 2009 hit and proved me wrong yet again. And frankly, I just don't know how much longer I can take it.

It's not what you think!
You might be assuming that I'm talking about my positions in Caterpillar (NYSE: CAT) and Altria (NYSE: MO), which are still underwater despite one of the biggest rallies in years. But I'm actually talking about something much more painful for me personally: college football.

You see, my grandfather played football for Oklahoma, and I've been a Sooners fan since I was old enough to walk. So it was nothing short of devastating to watch Oklahoma lose its fifth straight BCS bowl game -- and its third straight national championship game -- to Saint Tim and team this January.

Of course, I'll always be a Sooners fan, even though they're now the Buffalo Bills of college football. After all, in sports, sticking by your team through the ups and the downs is a virtue. Just ask any Green Bay Packers fan.

Wall Street is a different ball game
For proof, just ask any longtime "fan" of:

Data provided by Yahoo! Finance.

Or ask my fellow Fool Rich Greifner.

Or even ask Jim Cramer. In his book Real Money, he reminds investors, "This is not a sporting event; this is money. We have no room for rooting or hoping."

Yet it happens all the time. Investing message boards are full of desperate investors who hope some cash-rich behemoth will come along and save their decades-old American superbrand. But as Circuit City investors found out, this is often a losing bet -- especially in this credit-strapped market.

Others ride stocks all the way into the ground because they're emotionally attached to the company's story, products, or management -- and meet with similarly dismal results. Take Krispy Kreme (NYSE: KKD) investors for example.

Ditch that loser!
One of the "20 Rules for Investment Success" from Investor's Business Daily is to "cut every loss when it's 8% below your cost. Make no exceptions so you'll avoid any possible huge, damaging losses."

To a sports fan, that advice might seem cruel and unusual, but it's actually good investment advice.

Or is it? To find out, I dug through David and Tom Gardner's Motley Fool Stock Advisor picks, because they often re-recommend a stock even after a big run-up -- or a sharp fall. I actually found three examples where breaking IBD's rule actually paid off big time:

These weren't flukes, either
In his re-recommendation write-up for Netflix, David Gardner admitted, "We're currently sitting on a 23% loss." But he went on to say, "I think this is one cheap stock at $11, backed by a great management team that's going to create value for us going forward."

Note that he had well-thought-out reasons for owning the stock: "It remains first and best in a growing industry, creates convenience for millions of consumers, and is led by visionary management that markets aggressively." Netflix stock has risen 200% since then.

So, when do you sell?
In today's market climate, IBD's rule probably looks like pure genius -- and it probably could have saved you a lot of pain.

In the process, though, you might have had to sell every stock in your portfolio, and you may well have set yourself up to miss out on some truly massive gains as the market rebounds.

When it comes to knowing when to sell, investors have drastically different strategies. Many have hard-and-fast numerical rules -- which is at least part of the reason we saw many excellent businesses losing 5% or even 10% per day late last year.

Others -- like the Gardners -- stick to a more analytical and intellectual approach to determine when to recommend that their Stock Advisor subscribers sell a stock. So when do David and Tom Gardner consider dumping a stock? Primarily when they encounter:

• Untrustworthy management
• Deteriorating financials
• Mergers, acquisitions, and spinoffs that could damage the business

The debate rages on
Someone once said, "I have no problem knowing when to buy a stock, but if I just knew when to sell, I'd be a great investor."

Investors may never agree on when or why to sell a stock. That's why it's important to have an emotionless, well-thought-out strategy in place. If you don't, you may suffer major losses or miss out on massive gains.

I challenge you to use the comment function below to tell us what your strategy is, and how it's held up through this brutal bear market.

For what it's worth, David and Tom Gardner rarely sell, and it works for them. Even in this wrenching market, their average Stock Advisor pick is performing 37 percentage points better than a like amount invested in the S&P 500.

If you'd like to see what David and Tom are recommending now -- including their top two picks for new money -- you can join them at Stock Advisor absolutely free for 30 days.

In addition to all of the stock picks and research, you'll also get full access to exclusive members-only discussion boards, where you can swap thoughts about when to buy or sell a stock with thousands of other dedicated investors.

To learn more about this free, no-obligation 30-day trial, simply click here.

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This article was first published Dec. 28, 2007. It has been updated.

Austin Edwards owns shares of Caterpillar and Altria. Dolby, Netflix, and Quality Systems are Motley Fool Stock Advisor recommendations. Microsoft is an Inside Value selection. Both The Motley Fool's disclosure policy and Sam Bradford will be around for at least another year. Unfortunately, so will Tim Tebow.