The Internet may prove to be the greatest human invention of all time. Investing in Internet companies in 2000, however, may prove to have been one of history's greatest follies.

Yet 2000 was a heady year for Internet investment. Guides such as Greg Kyle's 100 Best Internet Stocks to Own showed you "how to get in on this once-in-a-lifetime opportunity." Kyle predicted that there would be 430 million Internet users by 2003, and that by 2005, "consumers will spend $150 billion shopping online."

In fact, those estimates proved conservative. By 2003, nearly 600 million people were online. In 2005, shoppers spent more than $175 billion on the World Wide Web.

Time to cash in
But even though Internet usage blew away expectations, you would have been a big loser if you'd invested in Kyle's 100 best Internet stocks. How much of a loser?

In the fall of 2007, we went spent hours computing the returns figures. Spoiler alert: The results are painful.

Had you invested $1,000 in each of Kyle's 100 Internet names back on April 20, 2000, and held them through September 2007, your $100,000 investment would have turned into -- drum roll, please -- $37,814. That's a total return of negative 62%, and again, that return is through the fall of '07 -- before the current bear market.

You were more likely to pick a company that would go bankrupt (18) as you were to pick a company that simply increased in price (13)!

To the moon!
Even the success stories struggled with their valuations. Shareholders who bought in April 2000 made a small profit (about 10%) when Dow Jones acquired MarketWatch.com. (To further confuse, Dow Jones was later acquired by News Corp. (NYSE: NWS).) Checkfree, now part of Fiserv (Nasdaq: FISV), returned 39% to shareholders since from 2000 to 2007. Shareholders of Wit Capital Group, which became Soundview Technology, found 42% gains when Schwab (Nasdaq: SCHW) acquired their company.

There were, of course, some amazing returns. You would have done quite well buying Verio , which was acquired in 2000 -- Verio shareholders scored a cool 117% in about a month.

But even the big winners can't change the fact that 18% of Kyle's companies went bankrupt. And many of the companies that survived, including Drugstore.com (Nasdaq: DSCM), Sapient (Nasdaq: SAPE), and Quest Software (Nasdaq: QSFT), are down about 50% or more. Continued...