The escalating price of buyouts and the valuations of recent IPOs have plenty of people worried we're in - or approaching - another tech bubble. Experts are divided on how accurate those fears are, but there's no denying the implosion that occurred around the turn of the century.

The first tech bubble saw ridiculous levels of spending - from both executives and venture capitalists - and it was only a matter of time before investors hopped on that bandwagon.


A lot of those shareholders ended up losing their shirts when the bubble burst, though many would confess that the investment decisions they made at the time were hardly prudent. Here are some of the most infamous flops of the era.

Webvan
The grocery delivery service had a good idea, and expanded rapidly, growing to eight cities in 18 months - and it had plans to expand to 26 more between mid-1999 and 2001. It also placed a $1 billion order for planned warehouses in the months leading up to its IPO.

That confidence pumped up investors - and the company raised $375 million in its 1999 IPO. Shares ultimately hit $30, but the company couldn't attract customers at the necessary pace. Combined with the thin margins of the grocery business, it ultimately fell to 6 cents per share. Webvan called it quits in 2001.

TheGlobe.com
Some argue that the dot-com bubble began its rapid inflation the day TheGlobe.com went public in 1998. On its first day, the social media forerunner, which let users publish their own content and interact with others with similar interests on hosted discussion groups and home pages, saw shares increase their value by 600 percent. Set to price at $9, trading started at $87, ultimately settling at $63.50.

With a market cap of $842 million, the company seemed destined for greatness, but wasn't able to sustain growth.

"The rules of the game changed as soon as we went public," co-founder Stephan Paternot wrote in his book "A Very Public Offering: A Rebel's Story of Business Excess, Success, and Reckoning." "It was not about developing our business model, but increasing shareholder value. We were doing well if our stock went up and badly if it went down."

By August 2001, Nasdaq de-listed the stock. A strong shift in focus in 2003, when the company launched GloPhone - a VoIP phone service similar to Skype - helped it hang on through 2007. But the company was besieged by lawsuits and found guilty of violating anti-spam laws just as Facebook was becoming red hot. Today, it's a shell company, with no notable operations or assets. (Some companies were able to outlive the dotcom bubble: 5 Successful Companies That Survived The Dotcom Bubble.)

Pets.com
It's impossible to think of the first Internet era without thinking of the Pets.com sock puppet. He was everywhere and was nearly as well-known as the Geico gecko is today.

That familiarity, in part, persuaded many investors to lay down money in the company's February 2000 IPO (which was backed by Amazon.com). Pets.com raised $82.5 million – but nine months later it folded, due to major recurring losses. Part of the reason for that was aggressive advertising, but the company also lost money on virtually every item it sold. In the third quarter of 2000, Pets.com reported negative gross margins of $277,000. (The second quarter had seen a $1.7 million margin loss.) That same quarter (its last full quarter as an operating entity), the company lost $21.7 million on $9.4 million in revenue.

As for the puppet, he went on to shill for BarNone, which helps people with bad credit histories get car loans. He's still there today, front and center on that website.

Lastminute.com
This travel site, based in the U.K. but with a sizable U.S. audience, had one of the fastest collapses of a public company - and is regularly cited as the beginning of the end for the dot-com era. Founded by Martha Lane Fox and Brent Hoberman in 1998, it went public in the United Kingdom just as the bubble was bursting.

Shares surged in the first day - despite the offer price doubling to 380p ($6) at the last minute. Lastminute.com gained as much as 48 percent before settling at a 28 percent first-day gain. Within two weeks, the price had plunged.

Through 2005, when it was bought by Travelocity owner Sabre Holdings, the company never reported a profit. And investors were forced to sell back their shares for 165p ($2.75) each - a 215p (more than $3) per share loss for anyone holding them since the IPO.

eToys

Don't be fooled by the eToys.com that's online today. Aside from its name, it has nothing to do with the dot-com company launched in 1997.

Backed by Sequoia Capital, Highland Capital Partners and Idealab, this online retailer's 1999 IPO was a roaring success, with shares jumping from $20 to $77 on the first day. At one point, the company was valued at over $8 billion, but the fight to compete with Amazon, Wal-Mart and other retail giants proved too costly. (Toys R Us at the time didn't have a big online presence.) By February 2001, shares were down to $1 each and the company filed for Chapter 11 bankruptcy.

Drkoop.com
The former U.S. surgeon general who rose to fame during the Reagan administration leveraged his name to form one of the first health information websites. It was a traffic hit, too, boasting 1.4 million unique visitors in May1999, so when it raised $88.5 million from its IPO in June 1999, no one was surprised.

Within a month, shares were at $45.75 and a strategic partnership was in place with AOL. (drkoop.com agreed to pay AOL $89 million over four years to make it the top healthcare content provider across the AOL sites.) But the collapse of the tech bubble - as well as the loss of millions of dollars per quarter in an effort to acquire readers - scared investors. (In March 2000, the company had cash expenses of $8 million.)

In October 2000, the company secured what appeared to be a life-saving $20 million investment, but was forced to liquidate in December 2001 after burning through that money.

Kozmo
There are still people in metropolitan areas who miss this delivery service, which delivered anything from movies to snacks in under an hour - with no minimum purchase and no tipping allowed. Private investors kicked in $280 million to help it grow, no doubt looking forward to recouping that in the IPO, which was filed in March 2000.

By that time, though, the dot-com world was imploding, and the company, which was also being dogged by allegations of "cyber redlining" in its delivery areas (avoiding many neighborhoods with high concentrations of black residents - a practice the company denied), shelved its IPO plans. By April 2001, it called it quits.

FreeInternet.com
The early dial-up days of the Internet were ruled by companies that charged a monthly fee to connect to the web. FreeInternet.com was part of the movement to change that paradigm and was famous for its commercials featuring the talking infant "Baby Bob."

It grew to be the fifth-largest Internet service provider in the country - and planned to go public, but lavish spending led to a bankruptcy in 2000, canceling the planned IPO before it could happen.

As for Baby Bob, he went on to get his own TV show on CBS, which lasted two seasons. Later, like the Pets.com sock puppet, he surfaced with another brand - this time Quiznos.

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