A Short Time Ago ...
By Oliver Ryan

(FORTUNE Magazine) – ... in an economy far hotter than today's, entrepreneurs roamed the land talking of frictionless markets and hockey-stick return curves. In the five years from the day Netscape went public to early 2000 when the Nasdaq briefly topped 5,000, 818 venture-backed companies went public, raising a total of $47 billion. It was a halcyon time of visionary hucksters and viral acronyms, a time when giants were born--eBay, Amazon, and Yahoo--and wannabe giants died. We recall some of the notable excesses. -- Oliver Ryan

Most Unfashionably Early

Fashion portal Boo.com promised to be "a gateway to world cool." It spent $135 million and staffed up to 400 people but closed shop abruptly in May 2000, among the first to fold. (The site's Ms. Boo is shown below.)

Most Impressively Wrong

Webvan, the online grocer backed by bookstore entrepreneur Louis Borders, Goldman Sachs, and top VCs, pulled off a $370 million IPO and ate up nearly $1 billion before checking out for good. Webvan inspired pages of haiku on sarcastic site FuckedCompany.com. Example:

A grocer I am

I knew it could never work

But no one asked.

Most Decadent Party

Pixelon.com dropped over $10 million on its Las Vegas iBash, featuring appearances by Kiss and the Who. Shortly thereafter, the founder was jailed for a prior fraud conviction, and the site went bust.

Most Hail Mary

Hoping to overtake larger rival Monster.com, HotJobs.com spent $2 million--half of its 1998 revenues --on a 30-second TV ad during the 1999 Super Bowl.

Most Unhealthy Med Site

Caution: Maverick surgeon generals may be hazardous to your financial health. DrKoop.com aimed to bring medical info to the masses. The startup hit a market cap of $1.3 billion before dying an ugly death in 2001.

Most Stupefying Deals

AOL acquires Time Warner: $147 billion At Home acquires Excite: $5.9 billion Terra Networks acquires Lycos: $5.5 billion AOL acquires Netscape: $4.1 billion

Most Wannabe Silicon Valley

Silicon Alley, Silicon Prairie, Silicon Gulch, Silicon Desert, Silicon Dominion, Silicon Tundra, Silicon Bayou

Most Opportunistic

Half.com talked Halfway, Ore. (pop. 345), into renaming itself Half.com, Ore., in exchange for $75,000 and 22 computers.

Mostly Gone Mags

Industry Standard Yahoo! Internet Life Internet Week Red Herring (relaunched) Fast Company (revived)

Most Contagiously Upbeat

These celebrity securities analysts rode the tech indexes to the top and back down again. Henry Blodget Merrill Lynch Jack Grubman Salomon Smith Barney

Most Fallen Visionaries

David Wetherell acquired his way to stardom--his CMGi reached a market cap of $41 billion before collapsing under its own weightlessness. Jay Walker built the Walker Media empire on filing patents, but he struggled mightily with execution. Craig Winn pitched Value America as the future of retailing to the likes of Paul Allen and FedEx's Fred Smith, but the dot bomb was gone by the end of 2000.

Most Mascot

Pets.com spent millions of dollars on ads featuring its sock-puppet dog. The company died, but amazingly the sock puppet lives on. It now hawks loans for 1-800-Bar-None under the slogan "Everyone deserves a second chance, BarNone!"