Sources: Travel and Leisure and Georgetown University.

Can you remember the adolescent Internet in the year 2000?

It was the heyday of message boards and forums, and your grandparents didn't have email yet. It was also an inflection point for retail investors.

For the first time ever, an average Joe and Jane sitting in their living room could access the same information available to elite Wall Street analysts.

It was a time when the SEC, Wall Street, and everyday investors like you and me were grappling to deal with securities laws ill equipped for the Wild West of the Yahoo! Finance message boards. This was the world 15-year-old Jonathan Lebed entered when he first logged on to day trade stocks.

With the brokerage account his mother opened for him, Lebed would build positions in micro-cap stocks and then hit the message boards hyping the stocks.

Like a young Wolf of Wall Street, Lebed successfully traded his way to nearly $1 million before the SEC stepped in.

The story is wrought with connundrums. Is the trading game rigged for the pros on Wall Street? At what point does a 15-year-old kid writing anonymously on message boards become a master market manipulator?

The original New York Time article from February 2001, 13 years ago this month, frames the complexity and absurdity of day trading then and now:

By the Spring of 1998, Jonathan was 13, and his ambitions were growing. He had glimpsed the essential truth of the market: that even people who called themselves professionals are often incapable of independent thought and that most people, though obsessed with money, have little ability to make decisions about it. He knew what he was doing, or thought he did. He had learned to find everything he wanted to know about a company on the Internet; what he couldn't find, he ran down in the flesh. It became part of Connie Lebed's life to drive her son to various corporate headquarters to make sure they existed. He also persuaded her to open an account with Ameritrade. ''He'd done so well with the stock contest, I figured, Let's see what he can do,'' Connie said.

Be a business and investing predator
Warren Buffett encourages investors to invest in index funds for the low cost and highly diversified exposure to stocks. It's a long-term strategy, and it seems smart enough. Hey, it's Warren "the Oracle of Omaha" Buffett, for crying out loud!

But Buffett himself doesn't exactly follow the same approach.

Whoa, cowboy! Manage your risks!

His extreme success came from investing heavily in a smaller basket of companies and holding them forever. Take a look at Berkshire Hathaway's (NYSE:BRK.A) (NYSE:BRK.B) latest holdings for proof; its hardly comparable to the S&P 500.

Ted Turner, another billionaire, certainly didn't diversify when he was building what would become Time Warner Cable (NYSE: TWC) and Time Warner (NYSE:TWX). Same for Fiat founder Giovanni Agnelli, hedge fund billionnaire John Paulson, Wal-Mart founder Sam Walton, and countless other extremely successful business owners, investors, and tycoons.

But this lack of diversity does not imply a cowboy's approach to risk. In fact, according to this article by Malcolm Gladwell from a 2010 issue of The New Yorker, these success stories are characterized by a shocking lack of risk. The lesson is worth its weight in gold for investors large and small: 

The entrepreneur has access to that deal by virtue of occupying a "structural hole," a niche that gives him a unique perspective on a particular market. Villette and Vuillermot go on, "The businessman looks for partners to a transaction who do not have the same definition as he of the value of the goods exchanged, that is, who undervalue what they sell to him or overvalue what they buy from him in comparison to his own evaluation." He moves decisively. He repeats the good deal over and over again, until the opportunity closes, and -- most crucially -- his focus throughout that sequence is on hedging his bets and minimizing his chances of failure. The truly successful businessman, in Villette and Vuillermot's telling, is anything but a risk-taker. He is a predator, and predators seek to incur the least risk possible while hunting.

What's the takeaway from all this?
These two pieces together give tremendous insight into what it takes to be a successful investor. First, the day-trading, short-term style of investing that is hyped by talking heads is a rigged game against you as a retail investor. The system is designed to eat away your returns with fees and commissions, and short-term market movements are not based on any real analysis of a businesses prospects, but instead by mysterious market forces you can't control or truly predict. 

To be a predator, to truly win in the game of business and money, you must play the game on a level playing field. You must research your investments and understand the company's fundamentals and future prospects. When you find that special company that is undervalued, that is poised for long-term success, you pounce. You've found your prey, and it's time for you to be a predator. 

This article represents the opinion of the writer, who may disagree with the “official” recommendation position of a Motley Fool premium advisory service. We’re motley! Questioning an investing thesis -- even one of our own -- helps us all think critically about investing and make decisions that help us become smarter, happier, and richer.