List of the Billionaire Losers Club

By
Andrew E. Serwer <br> Special to ABCNEWS.com
January 6, 2006, 1:31 AM ET
3 min read

May 30, 2001 -- There's a new, very exclusive club that some of the captains of the e-commerce world belong to, but the dues are oh, so high. It's Fortune magazine's billion-dollar losers club.

And many of the members come from some of the new Internet companies that went public over the past few years. These are the firms who went through the roof in the late 1990s, then came crashing down last year.

A note first: We didn't include people like Microsoft's Bill Gates or Oracle's Larry Ellison on the list, who surely lost money, but their billions are still intact.

So, let's take a look at some big names and big losses that did make the list.

Best of the Worst: Michael SaylorThe first inductee is MicroStrategy CEO Michael Saylor. Saylor may not be a household name, but he lost over $13 billion. His Washington D.C.-based firm makes software to help companies keep track of consumer trends in their databases and computer transactions. At one point, Saylor was the richest man in D.C., and while he still has $179 million left, he has scrapped plans to build a Versailles-like mansion.

Retailer Rut: Jeff Bezos

Jeff Bezos of Amazon.com claims the No. 2 spot. Bezos has lost over $10 billion, but he is still worth more than $1.7 billion. He's been working very hard to expand Amazon, and is now working even harder to reach his goal of turning his company to profitability for the first time this year.

Chief Yahoos: David Filo and Jerry Yang

Filo and Yang, who jointly created Yahoo!, find themselves tied for third. Filo has lost $10.3 billion and Yang a little less, because he owns less stock. Yahoo's stock was once valued at $150. It closed yesterday at $18.79.

Spacing: Naveen Jain

Naveen Jain, the CEO of Seattle-based InfoSpace is the fourth-biggest loser. InfoSpace delivers content to a variety of Web sites — from AOL to MSN — and was a hot stock back in the day. But Jain still has faith in his product, saying "I will get those billions back and then some. The billions lost will be like pocket change."

‘Beam Me Back’: Jay Walker

And finally, rounding up the top five is the founder of one of the most well-known companies from the Internet revolution. He's none other than Priceline's Jay Walker. There's no word on how much William Shatner lost, but CEO Walker took a $7.5 billion pounding. How is he handling the loss? "[It's] not the end of the world," he says.

Final Thoughts

So here's the bottom line: These guys still have hundreds of millions of dollars, and their net worth is probably a lot closer to the real value of their companies.

While many of these firms were successful initially, they were overvalued, making their fortunes difficult, if not impossible, to sustain. If the 20 "losers" on this list simply looked at how much money they had five years ago compared to today, they should all be very happy.