The 50 Worst Internet Startup Fails of All Time

Facebook's post IPO performance has been abysmal. Groupon is losing top talent like the Florida Marlins after a championship. And HP, Dell, and Intel have become cannon fodder for the recent outpour of smart phones and tablets. The Internet has the potential to make people incredibly wealthy while, simultaneously, fueling a misplaced enthusiasm from venture capitalists and investors who are looking to turn a quick $100 million. We've got high-flying stocks turned duds and a laundry list of companies that fell apart when they were forced to do more than add an "e-" prefix to their company names. You think today's startup woes are bad? Keep reading.

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Year Of Birth: 1998
Year Of Demise: 2000
CEO: David Kim Stanley
Founded By: David Kim Stanley

Pixelon promised the transmission and distribution of high-quality video over the Internet. The company’s founder, David Kim Stanley, was a convicted white collar criminal who was using the alias “Michael Fenne.” The company drew headlines for its Las Vegas launch party, which featured over-the-top musical performances by KISS, Tony Bennett, The Who, and LeAnn Rimes at a reported cost of over $16 million. Shortly after, it became clear that the company was a fraud, boasting mostly misrepresented technology and serving as a personal embezzlement factory for Stanley.

Year Of Birth: 1998
Year Of Demise: 2002
CEO: Donna Jensen
Founded By: Donna Jensen

Billed as the “ultimate dot-com startup,” startups.com aided businesses in buying office space and appointing a board of directors. During the bubble, startups.com landed major players like Google and eVite and opened offices in Silicon Valley, Boston, and New York. When the bubble burst, their client base shrunk considerably, leaving the company for dead by 2002.

Year Of Birth: 1998
Year Of Demise: Purchased by Sabre Holdings in 2005
CEO: Matthew Crummack
Founded By: Martha Lane Fox and Brent Hoberman

The travel site specialized in selling distressed inventory like vacant hotel rooms and undersold flights. In 2000, lastminute.com debuted on the London Stock Exchange with a booming first day, closing with a value of £768 million (roughly $1,238,937,600). Over the next six months, lastminute would see similar U.S. companies fall victim to the softening market and, to its own fault, perpetually delayed the unveiling of its reimagined website. A year after its initial flotation, the company’s stock price would fall 90% before being acquired by Sabre Holdings (the parent company of Travelocity) in 2005.

Year Of Birth: 1995
Year Of Demise: Acquired by Yahoo! in 1999
CEO: Todd Wagner
Founded By: Cameron Christopher Jaeb

Designed as a way to broadcast radio over the Internet, broadcast.com had a record IPO with a stock price that more than tripled in size on its first day. The record offering turned more than 100 initial investors into millionaires on paper and turned the founders, Cameron Jaeb, and current Dallas Mavericks owner, Mark Cuban, into overnight billionaires. In 1999 Yahoo!, acquired the company for $5.7 billion and has since divided it into a variety of services that have either been discontinued or simply redirect to yahoo.com.

Year Of Birth: 1999
Year Of Demise: Acquired by Cisco Systems in 2004
CEO: Randall Kruep
Founded By: Dr. Sharad Mehrotra, Dr. Bill Lynch, and Dr. Tony Li

Procket Networks emerged from the dot-com bubble virtually unscathed. The softening market destroyed much of Prockets’ competition, leaving the telecommunications company in an incredible position to dominate the marketplace. Of course, that never happened. After raising close to $300M in ’02, the company went into a tailspin and was unexpectedly upended by Cisco and Juniper Networks. Cisco eventually acquired the company’s intellectual property in ’04 for less than $100M.

Year Of Birth: 1997
Year Of Demise: 2001
CEO: Barry Gold
Founded By: Frank Han

EToys opened its ’99 IPO at $20 a share. By the closing bell, it was one of the hottest stocks on Wall Street with a price that had ballooned to $76. After the dot-com bubble the company began losing millions and was eventually purchased by KB Toys for a mere $5M. Later, the website filed for a separate bankruptcy under another owner in 2008. In 2009, the domain name was purchased by Toy “R” Us. The site is now a retail portal for all of Toys R Us' properties.

Year Of Birth: 1994
Year Of Demise: 2001
CEO: Josh Harris
Founded By: Josh Harris

If Josh Harris was an athlete, he could have been on ESPN's Broke. After his video broadcasting company went through several rounds of investments, the Pseudo staff began throwing over-the-top parties in its Manhattan office. The company turned into a self-aggrandizing ode to the company’s founder Josh Harris who would go on to admit that the aptly named company was “fake” and “the lynchpin of a long form piece of conceptual art.” The company famously hosted a three-day marathon party where more than 300 gamers from around the globe gathered for the world’s largest ever Quake LAN party. At least they went out with a bang.

Year Of Birth: 1996
Year Of Demise: 2000
Ceo: David Dorman
Founded By: Christopher R. Hassett

Pointcast basically amounted to a screensaver that displayed breaking news. The product often required more bandwidth than dial-up connections would allow at the time and was totally impractical for corporate networks. Despite its shortfalls, News Corporation made a $450M offer to purchase the company’s technology. Pointcast’s then-CEO Christopher Hasset balked at the deal and was immediately ousted by the company’s board of directors. The company botched another deal to be acquired by an investment group that included Microsoft and was later purchased for $7 million before its network was shut down.

Year Of Birth: 1999
Year Of Demise: 2000
CEO: Judy MacDonal
Founded By: Jim Clark

With a popular following and more than $20M in venture capital, this online community for teen girls threw a lavish launch party in 2000. Less than two months later, the company was completely bankrupt. Kibu was extremely popular amongst young women but, after several Silicon Valley high rollers impulsively withdrew their investments, the company caved. No worries, though, all those teen girls are now on Pinterest.

Year Of Birth: 1998
Year Of Demise: 2000
CEO: Robert McCausland
Founded By: Robert McCausland

Freeinterenet.com was an unrestricted alternative to subscription-based Internet, providing users with an alternative pay-as-you-go ISP. The company reported revenues of $1M in '99, but recorded a loss of $19M. You don't have to know Clinton arithmetic to know that losing nearly 20 times what you make in a year is bad business. The company laid off its entire workforce and cancelled its IPO a year later.

Year Of Birth: 1998
Year Of Demise: 2001
CEO: William J. Razzouk
Founded By: Michael Bruner

PlanetRX once carried a stock price of over $290. Then company got bodied in the online beauty and health marketplace, losing more than $120M in a year. Things got so bad that its share prices plummeted to $.30. Before closing its doors for good, PlanetRX decided to liquidate its assets to scrape together a sum of $9 million that was split amongst its shareholders. Facebook doesn't seem so bad now, does it?

Year Of Birth: 1999
Year Of Demise: 2001
CEO: Donald Hackett
Founded By: Dr. C. Everett Koop

The Regan administration's Surgeon General, and all-around shady looking dude, Dr. C. Everett Koop, started DrKoop.com, a pre-WebMD self-diagnostic website. Boasting over 1 million unique visitors a month, the stock’s price rose to nearly $50 a share. After the bubble burst, however, investors grew weary of dumping cash into a company whose only source of income was advertising. The company started bleeding cash, losing millions of dollars every month until it was sold for less than $200K. A prime example of an idea too ahead of its time.

Year Of Birth: 2003
Year Of Demise: Present
Ceo: Tim Vanderhook
Founded By: Chris DeWolfe and Tom Anderson

Before Instagram-ing their cleavage in nightclub bathrooms and feeding their egos with tweet after hackneyed tweet, Generation Y's amateur models made cumbersome, unsightly profile pages on MySpace. In 2003, the company was purchased by News Corporation for over $500M and in 2006 surpassed Google as the country's most visited website. At its peak, MySpace was valued at $7 billion. However, the company has been eclipsed by a number of social networking sites and has experienced a dramatic drop in users despite multiple redesigns and site overhauls. In 2011 News Corporation took a hit on their investment of over half a billion dollars, recently selling the fledgling site for $35M.

Year Of Birth: 1996
Year Of Demise: 2007
CEO: Aaron Cohen
Founded By: Dan Pelson, Lee Morgenroth, David Cancel, Jane Mount

Bolt was an early social networking site that attracted a pretty healthy base of teenage users. As the site’s users began to age, Bolt ushered in a “new and improved” version of the website that was widely disavowed by longtime supporters. With much of its original user base gone, Bolt introduced the poorly namedBolt2, which emphasized user uploaded videos. When Universal partnered with YouTube, the music industry magnate filed suit against Bolt2 for copyright infringement. Unable to fight against the superpower, Bolt was forced into bankruptcy.

Year Of Birth: 1996
Year Of Demise: 2001
CEO: N/A
Founded By: Susan Polis Schutz

E-mail effortlessly made the pen pal and the carrier pigeon obsolete, but—as we learned from BlueMountain—it still has a ways to go before it kills the greeting card. In ’96 BlueMountain began an e-greeting card empire that was purchased for $780M. Two years later, the company sold for $35M, a 96% hit.

Year Of Birth: 1996
Year Of Demise: 2000
CEO: Craig Winn
Founded By: Craig Winn and Rex Scatena

Value America attempted to connect consumers directly to manufacturers as a way to knock out the retail middleman and save on shipping. As it turns out, distributors are pretty important people because, apparently, manufacturers can’t communicate for shit. With the lack of a traditional supply chain, complaints of missing orders and delayed shipments piling up, the company collapsed. Value America, which in three years never turned a profit, was once valued at over $2 billion. By the time it closed its doors, stock prices had fallen to $0.72 and the company was forced into bankruptcy.

Year Of Birth: 1999
Year Of Demise: 2001
CEO: N/A
Founded By: J. Hutton Pulitzer

Digital Convergence developed the CueCat, a bar code reader that allowed users to scan print advertisements that led to web pages with related content. If that sounds like the dumbest idea you’ve ever heard, you’re not alone. The product was an enormous commercial failure and ranked #1 on Gizmodo’s list of the “Worst Inventions of the 2000s.” The horrible invention still managed to raise nearly $200M in investments from the likes of Coca-Cola and RadioShack, who lost it all when the product flopped in ’01. In '05, a liquidator offered CueCats in quantities of 500K or more at $0.30 a piece.

Year Of Birth: 1989
Year Of Demise: N/A
CEO: Michael Saylor
Founded By: Michael Saylor

On paper MicroStrategy was an incredibly successful software company. But, as the company would learn the hard way, using the same accounting practices as Enron will make any company look good—but only for a while. On March 20, 2000 MicroStrategy was forced to restate its earnings, leading to a share price that declined from $226.75 to $86.75 and a collective shareholder loss of $11 billion in one day. Less than two years later, MicroStrategy stock hovered at just over $4. That's just bad, even on paper.

Year Of Birth: 1999
Year Of Demise: 2011
CEO: Joseph Deutsch
Founded By: Dexster Smith and Joel Bellenson

Digiscents was a company that developed the iSmell, a device that plugged into a computer’s USB port and, in theory, generated different scents. Based on the online content being accessed by a user, the iSmell would emit an appropriate odor. Since the Internet is primarily used to watch porn and play World of Warcraft, the idea of an odor shamefully reminding you of your loneliness failed miserably. The Oakland-based technology company laid off all 70 of its employees in '11.

Year Of Birth: 2000
Year Of Demise: 2003
CEO: NA
Founded By: Jimmy Wales

Nupedia was the cantankerous Godfather to Wikipedia, a user-updated, online means to plagiarizing term papers and streamlining reading assignments. Unlike Wikipedia, updates could only be made by experts in the field and had to undergo a seven-step approval process. While considerably more reliable that Wikipedia, Nupedia’s horribly slow editorial process made the product totally useless. Seven months after the site's launch date, only two full-length articles had been published. Wales regrouped and tweaked the idea. Wikipedia was developed as an experimental off-shoot of the website and instantly became exponentially more successful.

Year Of Birth: 1980
Year Of Demise: 1999
CEO: Jill Barad
Founded By: Ann McCormick, Leslie Grimm, and Teri Perl

Anyone who went to middle school in the ‘90s should pour one out for The Learning Company. The software developer produced computer games like Oregon Trail, Carmen Sandiego, and the ClueFinder series. Toy magnate Mattel bought the company for $3.8 billion and, rather promptly, ran it into the ground, selling the company for $27.3M less than three years after its purchase.

Year Of Birth: 1994
Year Of Demise: Still hanging in there.
CEO: Bob Davis
Founded By: Bob Davis

What began as a research project for Carnegie Mellon student Michael Loren Mauldin, quickly became one of the Internet’s most popular search engines. By 1997, Lycos was the most profitable Internet business in the world. In 2000, the company was acquired for more than $12 billion by Spanish telecommunications baron, Telefonica. The purchase price was more than 3000 times Lycos' original venture capital investment. In a rather poetic turning of the tables, the company was sold in the summer of ’04 for less than $50MM. To put that into perspective, Telefonica lost more than $11M per day, EVERY DAY, for more than three years on their initial investment.

Year Of Birth: 1996
Year Of Demise: 2007
CEO: Naveen Jain
Founded By: Naveen Jain

The Internet magnate was once worth over $30 billion and considered a worthy advisory to Google’s prospective search dominance. Instead, the online yellow pages supplier saw its juggernaut stock price fall from $1,305 in March 2000 to less than $3 by June 2002. The company saw a revolving door of CEOs after the dot-com bubble burst and was engulfed by an accounting scandal in which the company reported $46M in profits despite actually losing close to $300M. So much promise, so much fail.

Year Of Birth: 1998
Year Of Demise: 2001
Ceo: Joel Granik
Founded By: Joel Granik

Typically, companies that bank on the laziness of Americans to turn a profit do so with tremendous success. So, CyberRebate’s plan to offer online rebates in exchange for tremendous upfront costs seemed like a winner. The company would charge $2000 for a stereo system that retailed for less than $300 and allow the consumer to get a full rebate so long as they submitted paperwork and agreed to strict deadlines. The company’s profit model was based on consumers being too stupid or lazy to follow up on the rebate, allowing CyberRebate to dump product at a tremendous markup. Instead, the company gave away electronic equipment to an especially astute customer base until it went under in 2001.

Year Of Birth: 1998
Year Of Demise: 2006
CEO: Brad Wurtz
Founded By: Dr. Lawrence Roberts

Caspian set out to build an enormous IP router that would deliver to users unprecedented quality of service. Early on, the company was seen as one of the more promising post-bubble startups. In fact, Caspian received almost $300M in venture capital and, at its peak, employed more than 300 people. The company struggled to identify itself, jumping onto various communications fads with a wide-range of services that drummed up very little interest. After six years of draining cash, Caspian shut its doors with less than 100 employees in 2006.

Year Of Birth: 1998
Year Of Demise: 2001
CEO: Michael Malaga
Founded By: Michael Malaga

NorthPoint was a data transmission company that supplied copper wire to small level Internet service providers. As the company landed a major acquisition deal with Verizon, the market began to soften and much of its customer base went bankrupt. With NorthPoint appearing much weaker as a company, Verizon backed out of the deal. The company quickly lost the ability to pay its creditors and in 2001 released the following statement to its ISPs: “NorthPoint no longer has funds available to finance the continued operations of our network... the complete shut down of our network will commence today." Hours later NorthPoint shut down its network leaving tens of thousands of end customers without service.

Year Of Birth: 1999
Year Of Demise: 2001
CEO: Jim Jorgensen
Founded By: Jim Jorgensen, Johannes Pohle, Carl Anderson, and Oliver Brock

AllAdvantage offered participants 50 cents an hour to download a view bar on their browser with a constantly changing rotation of banner ads. AllAdvantage was a great company for high school kids who wanted to make $100 a month, but failed to impress advertisers who didn't see the value in such a poorly paid demographic. The company paid out most of its $150M venture capital to kids surfing the Internet, while failing to attract advertisers. The business model never had a prayer.

Year Of Birth: 1999
Year Of Demise: 2002
CEO: Chris Gorog
Founded By: Shawn Fanning and Sean Parker

Napster was the rebellious hinge point of an Utopian era of type-and-listen music sharing. At its peak, the file sharing service boasted more than 80 millions songs and 25 million users. The company faced a myriad of lawsuits including famous settlements with Metallica and Dr. Dre. In order to pay copyright owners and future royalties, Napster attempted to monetize its service by making it subscription based. The model failed miserably and the company filed for bankruptcy in ’02.

Year Of Birth: 1994
Year Of Demise: 2000
CEO: Jason Olim
Founded By: Jason Olim and Matthew Olim

In 2000, the only investment worth less than a dot-com startup was a compact disc. CDNOW was a candle burning at both ends. The online music retailer fumbled its transition into digital music and quickly became a company that's product was readily available for free. When CDNOW went public, it carried an estimated value of close to $350M. Three years later, Amazon purchased the company for less than half its peak worth.

Year Of Birth: 1998
Year Of Demise: 2000
CEO: Kaleil Isaza Tuzman
Founded By: Kaleil Isaza Tuzman and Tom Herman

Designed as a web portal for civic requests, GovWorks aimed to streamline and organize communications between citizens and local government. The company had a sound business plan but—like many on this list—rushed to market without the ability to service a growing customer base. In three years of existence, the company burned through close to $60M in venture capital.

Year Of Birth: 1994
Year Of Demise: 2008
Ceo: Stephan Paternot
Founded By: Stephan Paternot and Todd Krizelman

The Globe debuted on the Nasdaq at $97 a share, the largest one-day advance in stock history. The company’s founder, Steve Paternot, immediately started behaving like a coked-out Gordon Gecko on Spring Break, buying a slew of luxury cars, spending tens-of-thousands of dollars at nightclubs, and generally behaving like a jackass. Less than two years later the stock fell to less than $2 a share before investors pulled the plug on Paternot’s social network.

Year Of Birth: 1998
Year Of Demise: N/A
CEO: Alfred H. Falk,
Founded By: Elwood "Woody" Norris

The business model for most dot-com startups was (and, in a way, still is) to build an enormous customer base, drain venture capital, and later define a way of turning a profit. No company embodied the spend-now-make-later model quite like e. Digital, which has only turned a profit in one of its 14 years in business. In January of 2000 the company’s stock peaked at nearly $25 per share. Today, that stock trades for less than $0.03. Live fast, die slow.

Year Of Birth: 1998
Year Of Demise: 2000
CEO: Frank Dunn
Founded By: John Roth

As the web bubble grew, municipalities began investing in technologically advanced corporate centers to attract dot-com startups. This involved sophisticated fiber optic grids and communications networks, a lot of which were supplied by Nortel. At its peak, Nortel boasted a workforce of more than 60,000 people and almost $400 billion in market capital. When dot-com startups started failing rapidly, the need for Nortel ceased overnight. By September 2000, the company had lost almost 99% of its market capital when stock prices fell from $124 a share to less than 50-cents.

Year Of Birth: 2005
Year Of Demise: 2012
CEO: Finn Batato
Founded By: Kim Scmitz

Have you noticed how hard it's been to download HD quality, pirated versions of The Dark Knight Rises lately? Earlier this year, the United States Department of Justice shut down the uber-popular megaupload.com—a network of file sharing and storage sites. The company's founder, Kim Dotcom, lived a lavish life with a $24M home in New Zealand, Rolls Royce Phantom, and reportedly watched TV on a 108-inch Sharp. According to the Feds, megaupload.com was an organization dedicated to copyright infringement and froze some $40M in company assets. Dotcom is currently awaiting trail.

Year Of Birth: 1993
Year Of Demise: 2004
Ceo: NA
Founded By: Albrecht von Müller

Founded by a philosopher who used technology to graph the human mind, Think Tools was a highly regarded IT company. During the dot-com bubble Think Tools was one of Europe's hottest companies, with nearly a $3 billion market value. Then it all began to unravel. In 2000 the company recorded enormous losses, leading many analysts to report that the stock was seriously overvalued. The next year, Think Tools recorded losses four times its reported revenues. By 2004, after years of losses, a Swiss IT company redIT AG bought it for peanuts. Obviously, von Müller didn't think this one all the way through.

Year Of Birth: 1994
Year Of Demise: 2007
Ceo: Jim Barksdale
Founded By: Jim Clark & Marc Andreessen

It's not hyperbole to say Netscape was one of the most important companies in the history of the Internet. The computer services company is credited with developing JavaScript and had an incredibly rewarding IPO as its stock soared from $28 to more than $75 on the first day of trading. At its peak, Netscape Navigator's market share was over 90-percent. November 24, 1998 would prove to be the turning point in the company's history as AOL announced it would acquire Netscape for over $4 billion. Some saw it simply as a play by AOL to unshackle itself from Microsoft (AOL's browser was based on Internet Explorer). Updates began to slow and the browser began to shed users. By 2003, Time Warner had disbanded Netscape, laid-off the programmers, and removed the logo from its building.

Year Of Birth: 1999
Year Of Demise: 2001
Ceo: Tom Jermoluk
Founded By: William Randolph Hearst III and John Doerr

When Excite acquired @Home for almost $7 billion in 1999, it was one of the largest mergers in Internet history. The merger instantly made Excite@Home one of the largest Internet service providers on the planet. In 1999 the company had over 1000 employees and was trading stock at over $100 per share. Because it was caking off, most investors overlooked the boardroom drama and volatile relationships between company executives. After the bubble burst, the company went into a tailspin as the Excite@Home’s stock fell to $2 a share. In 2001, the company was forced to sell its high-speed network to AT&T for $307M in cash. Excite would suffer the same fate when it was purchased by Ask Jeeves in 2004. What goes around comes around.

Year Of Birth: 1998
Year Of Demise: 2002
Ceo: Philip Letts
Founded By: Charles Cohen

Beenz was a company with a ridiculous name and even more absurd business idea: Develop a unique, online currency. Despite the e-currency only being accepted at participating online retailers, reckless venture capitalists still dumped over $100M into Beenz. The struggling company changed hands in 2000 and was shelved permanently in 2001. Eleven years later and e-currency still hasn't worked.

Year Of Birth: 1999
Year Of Demise: 2001
Ceo: George Shaheen
Founded By: Louis Borders

Louis Borders (of bookstore fame) teamed up with some successful venture capitalists to start an online, grocery delivery service. The motley crew had not an ounce of grocery experience between then, but believed their e-commerce plan to be invincible. The company dumped most of its money into infrastructure that outpaced its relatively successful sales numbers. The San Francisco company was forced to declare bankruptcy in '01, but, for some reason, still payed its former CEO George Shaheen a yearly severance of $375K. Nah, that doesn't sound right to us, either.

Year Of Birth: 1995
Year Of Demise: Ceased search engine operations in 2001
Ceo: N/A
Founded By: Jeff Gold

Go.com was Disney’s ill-fated answer to Yahoo, a corporate portal system that accessed web pages owned by the parent company. Most web users opted to use search engines instead, making Go.com a useless, all encompassing web domain for sites owned by Disney/ABC (You may have noticed some sites redirected to a URL with "go." at the beginning). Jeff Gold launched the site in '95 and it quickly became one of the most popular chat-room networks on the web. A half decade later, Disney laid off most of the company's work force.

Year Of Birth: 1998
Year Of Demise: 2001
CEO: Joseph Park
Founded By: Joseph Park and Yong Kang

On paper, Kozmo sounded like a great idea. A free delivery service that promised to bring anything from DVDs to Starbucks coffee to your door in less than an hour. The company’s founders woefully underestimated the cost in transporting small goods, promising free delivery with no minimum purchase. The company was forced to close its doors and lay off some 1,100 workers when the dot-com bubble burst. However, the company’s CTO, Chris Siragusa, launched MaxDelivery in 2005, a Manhattan-based company similar to Kozmo that’s still in business. Just goes to show, even a failure can be a learning experience.

Year Of Birth: 1994
Year Of Demise: 2001
CEO: Ellen Hancock
Founded By: K.B. Chandrasekhar and B.V. Jagadeesh

In four years, Exodus went from a company with a value of $0.00 to over $37 billion. The rapid growth and powerhouse board of executives made Exodus one of the most distinguished web hosting services in the world. It quickly began acquiring dot-com companies on a global and gluttonous scale. Exodus' indiscriminate overeating would prove fatal when the bubble burst and many dot-com customers stopped paying their bills. Cash starved, the company was forced into bankruptcy in 2001 and was acquired by Cable and Wireless for $800M, 2% of its estimated peak worth.

Year Of Birth: 1999
Year Of Demise: Closed in the U.S. in 2009
Ceo: Tom Evans
Founded By: David Bohnett and John Rezner

In 1999 GeCities was one of the most visited sites on the Internet and had a stock price close to $100 a share. The service allowed provided users with an easy way to build personal web pages. As the dot-com bubble ballooned, GeoCities was acquired by Yahoo for $3.6 billion in stock and promptly fell on its face. GeoCities shut down operations in the U.S. and Canada in 2009, scrapping almost 40M user-produced web pages in the process. Though once one of the Net's most dominate forces, Geocities is now the butt of jokes about poorly designed web pages.

Year Of Birth: 1998
Year Of Demise: 2000
CEO: Ernst Malmsten
Founded By: Ernst Malmsten, Kajsa Leander and Patrik Hedelin

Some criticize this English online clothing store for expanding too quickly, simultaneously launching in several European countries. But Boo.com’s biggest problem was its horribly conceived user interface, which relied heavily on JavaScript and Flash. Unless you were rocking a 56K modem in 2000, web pages took minutes to load. The company went from 40 employees, to 400, then to zero in less than two years and blew through almost $200M in 18 months.

Year Of Birth: 1983
Year Of Demise: Files for bankruptcy in 2002
CEO: Bernard Ebbers
Founded By: Bernard Ebbers

After being acquired by MCI for $37 billion in the largest merger in U.S. hsitory, the telecommunications company had a soaring stockprice and a rock star CEO in Bernard Ebbers. The company's foundern CEO spent most of the ‘90s gracing the cover of Business Weekly, and most of the ‘00s lying about how much money his company was worth. A small group of internal auditors discovered some $4 billion in fraudulent accounting, triggering an investigation of Ebbers and, ultimately, a 25-year prison sentence. It’s estimated that WorldCom inflated its worth by more than $11B and filed for bankruptcy in 2002.

Year Of Birth: 1983
Year Of Demise: N/A
Ceo: Gerald Levin
Founded By: Steve Case and Jim Kimsley

You know the America Online story. At a time when most people didn't have an email address, AOL provided users with an incredibly easy way to get online. Its suite of services (instant messaging, chat rooms, email) made it the darling of the Internet industry. When high-speed broadband Internet service began to permeate through American Internet users, AOL still trucked along. Then came Time Warner.

In perhaps the worst merger in corporate history, Time Warner partnered with America Online in 2001 just as the dot-com bubble was set to burst. Time Warner, a cornerstone of the media establishment, took a risk on the future of communications and paid for it dearly. In 2002, subscribers and advertising dollars bottomed out leaving AOL with a reported loss of $99B—the largest in corporate history at the time. Fast forward a decade and the company credited with getting most of the U.S. on the Internet transformed into a digital media company with the purchase of the Huffington Post and a host of other websites like Tech Crunch.

To be honest, we're surprised AOL is still around nearly 30 years later.

Year Of Birth: 1999
Year Of Demise: Still active
Ceo: Thomas H. Waechter
Founded By: Jozef Straus

JDS Uniphase came was the result of a merger between two fiber optics companies. During the dot-com bubble, the company ballooned into one of the tech world’s highest-flying stocks. After multiple mergers and a split, JDS boasted nearly 30,000 employees, many of which became instant millionaires—on paper. Then, the bubble burst. JDS stock tumbled from $153 per share to just over $2. The company laid off almost 90% of its workforce and recorded a then-record $56 billion loss in a single fiscal year.

Year Of Birth: 1998
Year Of Demise: 2001
CEO: Robert Levitan
Founded By: Robert Levitan

As frequent flier miles are to airlines, Flooz was to spending money online; an ancillary to using cash. Despite boasting a totally useless product, the company still managed to raise $35M from investors and land a pseudo celebrity endorsement deal with Whoopi Goldberg. Flooz was doomed from the beginning, but suffered a big setback when the FBI informed the government that Russian credit card thieves were laundering money through the site. According to the company’s CEO, almost one-fifth of purchases on Flooz were fraudulent.

Year Of Birth: 1998
Year Of Demise: 2000
CEO: Julie Wainwright
Founded By: Greg McLemore

More than anything else, you probably remember pets.com for its menacing sock puppet mascot. The startup spent most of its venture capital on marketing and, because it underestimated shipping costs, often lost money on online purchases. It was the perfect storm of a flawed business model, woeful marketing expenditures, and overextending its reach. During the company's first fiscal year, it recorded less than $700K in revenue, while spending close to $12M on advertising alone. Pets.com squandered over $100M, liquidating less than a year after its IPO.