The month is October ... the year is 1988. As the underdog Los Angeles Dodgers are shocking the Oakland A's in the World Series, Progressive Insurance (NYSE:PGR) is trading at $25. Adjusted for splits and dividends, that's around $0.65 per share.

Today, not long after the underdog Cardinals shocked the Tigers in the World Series, Progressive trades for around $24. In other words, it's been roughly a 35-bagger over the past 18 years, turning a $5,000 investment into $175,000. We believe there are several lessons to be drawn from the Progressive story that will help your future investing performance -- and that have helped our strong performance in Motley Fool Hidden Gems. We'd like to share them with you today.

1. The power of patience
Meaningful gains do not happen overnight, of course. In late 1988, George Bush had just won the presidential election. George H.W. Bush, that is -- the current president's father. That's certainly not ancient history, but the point is that it took 18 years for Progressive to increase this much in value. Time and patience are two of the most important factors in investing, and they can help overcome mediocre performance thanks to the power of compounding returns.

Consider that a person contributing $2,500 yearly to an IRA and earning an excellent average annual return of 15% will accumulate about $116,000 after 14 years. Yet someone who started investing just four years earlier will nearly reach the same total by earning an average return of only 10%. The important thing is to simply get in the game as soon as you can. Once you're in, hurry up and be patient.

2. Small is big
Back before it started its fantastic run, Progressive was valued at just $300 million -- a small cap by any measure. Today's future 40-baggers will also be small companies. They won't carry Citigroup's (NYSE:C) $269 billion market cap, for example. While Citigroup may very well provide solid returns over the next few years, its massive size will limit it from achieving jaw-dropping gains. Progressive itself can't even be the next Progressive, because it now sports a $17 billion market cap. While it's not nearly as big as Citigroup, it's still too big to achieve stunning gains in the future.

Small companies offer individual investors like us many other advantages. Most institutional investors, with billions of dollars to allocate, must avoid small caps -- at least until they grow larger. That makes small caps underfollowed and increases the chances that they're misvalued. To see why, consider an analogy we've used before. The less activity in a marketplace or auction house, the higher the probability of pricing inefficiencies. When there's only one bidder for an autographed Michael Jordan game jersey, the chances for mispricing are infinitely higher than when thousands of investors bid every day -- every hour -- on the present price of, say, IBM (NYSE:IBM) stock, which trades some 6 million shares each day on average. That inefficiency provides opportunity for us smaller investors.

3. A penny shaved
Progressive was never a penny stock trading below $1 per share. Future 10- and 100-baggers -- at least the ones we care about -- are most often trading between $5 and $50 per share. They're rarely below $5, and they certainly aren't below $1.

Penny stocks represent ultra-tiny companies whose shares can easily be manipulated by unscrupulous people misrepresenting the businesses' true potential. In short, stay away from stocks that aren't traded on one of the major U.S. markets (the New York Stock Exchange, Nasdaq, or American Stock Exchange), that have no revenues, or that are obviously being hyped via email or discussion boards. You'll save yourself a ton of grief.

4. Dandy dividends
In our research, we're constantly studying past big winners to find the common ties that bind them. Retailer Wal-Mart (NYSE:WMT) and insurer American International Group (NYSE:AIG) have different business models and different capital structures. Both, however, have trounced the market over the years, and both have paid a dividend ever since they were small companies.

Just because a company is small and pays a dividend, though, doesn't mean it's destined for greatness. But a dividend is a positive indicator, a telling sign of both financial strength and management's confidence that the business will continue to be solid through good times and bad. Progressive began paying its dividend back in 1986, when it was still capitalized at around $250 million.

5. Shareholder-friendly
In any company we research, we believe it's extremely important that management's interests be aligned with those of the shareholders. While investors want to see their shares outperform over the years, managers who are indifferent to the stock price may be more interested in hiring friends and grabbing perks than creating value. Former Tyco International (NYSE:TYC) CEO Dennis Kozlowski, for instance, had a $17,100 "traveling toilette box," a $15,000 umbrella stand, and a $6,000 shower curtain in his company-furnished apartment! Shareholders were glad to see him go.

This is why we love to see strong insider ownership at a company. (NASDAQ:AMZN) CEO Jeff Bezos has owned a significant part of his firm during its wild and profitable ride, and he still owns more than 24%. Peter Lewis, Progressive's chairman and founder, still owns more than 5%. His stake is worth more than $1 billion today. If you want to talk about leadership with a vested interest in a business' long-term success, this is the perfect example.

6. Boring excitement
So a world-class company like Progressive must be headquartered in New York, right? Or Hartford, Conn., the "insurance capital of America"? Nope. It hails from Mayfield Village, Ohio, in the eastern suburbs of Cuyahoga County, approximately 20 miles from downtown Cleveland. Low-key. Not flashy. A bit boring, even.

Reminds us of the early days of Wal-Mart, when the company didn't raise an eyebrow among big-time analysts. Wall Street treated Sam Walton's Arkansas boys like a bunch of hillbillies, it seemed. But these sleepy, small, "boring" companies -- with no hype built into their stock price -- can offer outstanding bargains to us individual investors.

Putting it together
In a recent issue of Hidden Gems, analyst Bill Mann and I (Tom) both recommended small-cap insurance companies that we believe will deliver outstanding returns over the next five to 20 years. Beating the market with small-cap stocks, as we've been doing in Hidden Gems, is not as difficult as you might think. We simply start by looking at what has worked in the past. Then we go looking for it again.

Hidden Gems is now three years old, and our total average return during that time is around 49%, compared with 22% for similar amounts invested in the S&P 500. If you'd like to check out all of our recommendations, plus more than 20 valuable investing lessons, we're offering a special 30-day free trial. Click here to give it a whirl.

This article was originally published on April 8, 2005. It has been updated.

Tom Gardner is co-founder of The Motley Fool and heads up the Hidden Gems newsletter. Rex Moore helps him pan for gems and doubles as his bodyguard. Neither owns shares of any company mentioned in this article. is a Motley Fool Stock Advisor recommendation. Tyco and Wal-Mart are Motley Fool Inside Value recommendations. The Motley Fool is investors writing for investors.