Pets.com is one of the most emblematic dot-com companies

Many original dot-com company founders were bought out early on

The people who bought the original domains for dot-com companies and had the ideas to start businesses were often bought out by investors before becoming well-known companies. Both Pets.com and Broadcast.com were acquired early on.

Theranos and Pets.com are among some of the biggest startup failures ever

You might have heard of Theranos, Elizabeth Holmes’s one-time blood testing company that landed the founder in prison for more than a decade after she was charged with fraud. The rest of the startups on a list of five of the biggest startup failures ever might not be as famous as Theranos, but they were met with similarly disastrous fates.

See which companies folded and which survived the dot-com crash

Companies that primarily used the web as a platform for doing business were more vulnerable than companies that created technology. While hardware and software companies managed to make it to the other side, most e-commerce companies took a brutal beating and share prices plummeted.

PetSmart and Hilton are among 10 of the most famous leveraged buyouts in history

Some of the most famous leveraged buyout deals include Blackstone's 2007 acquisition of Hilton Hotels, in which Blackstone took the then-public company private and then returned it to the public markets in 2013. A British PE firm bought PetSmart for $9B in 2014—one of the most expensive leveraged buyouts since 2007.

IPOs that failed

Plenty of private companies fail once they try to go public. Failing can mean shares sell for less than their initial asking price on its IPO date, or it can look like a company pulling out of the IPO process at the last minute. Some companies with failed IPOs include Pets.com, Etsy, and Robinhood. Learn more about these companies and others here.

Watch a medley of Pets.com commercials with the famous sock puppet mascot

Pets.com used a sock puppet decorated like a dog (operated by comedian Michael Ian Black) as the company's mascot. The sock puppet became synonymous with the brand. An auto lender company called BarNone Inc. later purchased the sock puppet for $125K and rebranded it with the slogan "Everybody deserves a second chance."

Domains were like real estate in the dot-com era

In the early days of the World Wide Web, users needed to type URLs directly in the search bar to navigate to webpages (as opposed to the more general keyword search that browsers use now). This made simple, short, and intuitive domain names a hot commodity. So having a domain name, like Pets.com or Rent.com, that was easy to find and understand was like owning prime real estate on the WWW. (Some users may experience a paywall.)

More than 650 companies went public in the US in 1996

As the dot-com bubble reached its peak, most dot-com companies went public with little proof of being profitable and were often overvalued. In 1999, the Nasdaq's price-to-earnings ratio (a tool used to determine a stock's value that divides its price by earnings) hit 90.2, signaling that many companies were operating at a net loss. Startups promised investors that more time and money would help scale their businesses and become profitable.

The dot-com bubble burst in the early 2000s

If you’ve heard of companies like Google and Yahoo, you’re already partially familiar with the dot-com bubble: a period from roughly 1995 to 2001, when internet companies were the hottest thing in venture capital. The “bubble” part of the term refers to the industry’s eventual implosion.

The dot-com boom sent tech stocks soaring before a historic collapse

A look at the dot-com bubble, when investors poured money into unproven internet startups, driving the Nasdaq to dizzying heights before it crashed by more than 80% after 2000, showing how new technologies can detach markets from reality.

Many dot-com companies spent some investor money on expensive parties

Parties hosted by dot-com companies were known to be extravagant and expensive. Technology companies in the Bay Area hosted between 15 and 20 parties a week on average, which cost between $30K and $50K on average.

The 'big bang' of the dot-com era: Netscape's stock price doubled on the day of its initial public offering

The company behind the browser that revolutionized search went public on August 9, 1995. Just before the IPO, the company increased its initial opening price from $14 to $28. On the day the company went public, shares traded as high as $71 before closing at $58.25. The company's market capitalization exceeded $2B. The eye-popping IPO is largely considered the beginning of the dot-com bubble.

Dot-com companies paid $44M for Super Bowl ads in 2000

During the 2000 Super Bowl game, 17 dot-com companies paid $44M total for ads. Just the next year, only three dot-com companies ran ads in the game. The significant drop reflects just how hard the crash hit dot-com companies and how unsustainable the businesses were.

The dot-com bubble burst in 2000 when the Nasdaq dropped more than 76% in roughly 2 years

Between 1995 and 2000, the Nasdaq Composite index jumped from roughly 1,000 to 5,000 amid excitement over new internet companies. As venture capitalists dumped money into startups, those same companies struggled to turn a profit, leading to a bubble. The Nasdaq wouldn't reach its former high until 2015.

Peter Thiel and Elon Musk formed PayPal after merging two dot-com companies

Elon Musk cofounded "X.com," an online banking service, in 1999 with the idea that the web would become a financial repository as internet access expanded and became ingrained in daily life. Peter Thiel cofounded "Confinity" as a digital security service that morphed into a payments system. In 2000, the two merged to form PayPal, and in 2002, they sold PayPal to eBay for $1.5B.

'The Million Dollar Homepage' is a snapshot of a dead internet

In 2005, 21-year-old Alex Tew set out to make $1M by selling $1 pixels on his website, effectively creating a standalone internet billboard. The gambit worked, and because the advertisements were one-time payments, the site looks the same as it did in 2005, despite many of the advertised sites going defunct since.

Red Lobster lost $11M on endless shrimp promotions—but its real estate holdings were what dragged it to bankruptcy

Golden Gate Capital, a PE firm, bought Red Lobster in 2014 for $2.1B. Golden Gate then sold Red Lobster's real estate, more than 500 storefronts, which generated $1.5B in revenue and helped finance the PE firm's acquisition of the company. Analysts say increased debt, high rent costs, and low equity put Red Lobster in an impossible position, leading to its 2024 bankruptcy filing—although the shrimp bill probably didn't help.

In 1994, Amazon was founded as an online bookseller

Books were just the start, as founder Jeff Bezos' ultimate goal was to create an "everything store," using the internet to transcend the physical limitations of brick-and-mortar retail. The Seattle-based Amazon gradually added CDs and consumer electronics, becoming a dominant e-commerce player in the late 1990s, and one of the few dot-com companies to make it through the bust.

Venture capitalists were once bullish on DTC brands

While a physical store can only hold so many objects, online retailers without the limits of four walls that could sell their products direct-to-consumer could theoretically be great investments. But they didn’t always provide investors with expected returns.

Sears once tried to become a tech company

In 1984, Sears arguably created one of the first online retail services, called “Prodigy,” in 1984 alongside IBM and CBS. But it was more of a WeChat than an Amazon, offering a variety of other services to users a few years before the dot com era.

A private equity firm led the leveraged buyout of Toys 'R' Us before the company's bankruptcy

After being acquired by two private equity firms and a real estate company for more than $6B in 2005, Toys 'R' Us filed for bankruptcy in 2017. Many point to the $400M a year the company had to pay to service its debt, as well as increased competition from online retailers like Amazon, for draining its profits and ultimately dragging it under.

The dot-com boom made Mark Cuban a billionaire

Cuban co-founded AudioNet with Todd Wagner in 1995 before it became Broadcast.com—a web app that allowed people to listen to sports commentary on their computers if they couldn't watch a game. In 1999, Yahoo bought Broadcast.com for $5.7B. By the time the market crashed, Cuban had already sold most of his stock in the company and had become a billionaire.

Yahoo acquired Paul Graham's former startup Viaweb in 1998

Viaweb was the web app tech startup that Paul Graham, Robert Morris, and Trevor Blackwell cofounded before they started Y Combinator. The company sold for $49M and Viaweb was rebranded as the Yahoo Store.

Amazon didn't have a profitable quarter until 2001, more than 6 years into its existence

Jeff Bezos, however, took pride in Amazon's early unprofitability, reinvesting the money Amazon made back into its business, prioritizing investment into long-term growth and customer acquisition over short-term gains.

2023's worst performing US IPOs

While an IPO is a huge milestone, it isn't always a total success in the long-term. This data visualization shows some of the worst-performing IPOs of 2023, based on their percentage returns at the end of the year, It includes an NFT gaming company and a Chinese EV battery company.

See a database of large companies owned by private equity firms

The Private Equity Stakeholder Project tracked more than 200 companies owned by private equity with more than 7,000 employees. Companies on the list include J. Crew, Jersey Mike's Subs, Barnes and Noble, Panera Bread, and Tropical Smoothie Cafe.

Sophia Amoruso's company Nasty Gal was worth $100M at its peak

In 2006, Sophia Amoruso started an eBay shop that would later transform into the clothing company Nasty Gal. However, Amoruso’s rags-to-riches success with Nasty Gal didn’t last. After multiple rounds of layoffs and employee complaints, the company filed for bankruptcy in 2016.

The Beanie Baby craze is known as one of the wildest collectible bubbles in history

The Beanie Baby boom saw collectors drive prices for stuffed animals into the hundreds or thousands of dollars, fueled by hype surrounding scarcity and online bidding wars. When demand collapsed in the early 2000s, the market crashed—leaving steep losses for many speculators.

Sears failed to evolve in a changing economy

At its peak, Sears was the largest retailer in the world, making elite objects accessible to the middle class. But in 2018, the company officially filed for bankruptcy due to massive debt and losses.

Digital coupon platform Groupon IPO'd in 2011 at a $17.8B market cap, but as of 2024 was worth just $103M—a 99.4% decrease.

Peloton's founder once said the company 'sells happiness' before a disappointing initial public offering

Ahead of the company's IPO, Peloton founder John Foley told investors that "on the most basic level, Peloton sells happiness." However, the inspirational sentiment didn't stick with investors—the company closed the day of its IPO with stocks trading down 11% from the IPO price. (Some users may experience a paywall.)

Elon Musk's first company was an online business directory called 'Zip2'

Musk started the online alternative to Yellow Pages in 1995 with his younger brother. Musk sold the company for $305M in 1999.

Some companies like to make their IPO day antics unique.

An article details some of the wildest bell-ringing day stunts in recent history, from Clifford the Big Red Dog ringing the opening bell to one company's employees roasting marshmallows in a campfire on Wall Street as it went public.

Read about the day Palantir went public in 2020

After more than 15 years in business, Palantir held its initial public offering (IPO) via a direct listing—meaning the company didn't rely on underwriters to assess the initial trading price or stock value. Palantir's stock ended the day trading 31% higher than the reference price.

See the 25 largest initial public offerings in US history.

These 25 companies—which include UPS, Uber Technologies, AT&T, and The Kraft Heinz Co.—had some of the biggest IPO drops in US history. However, not all these drops led to long-term (or even immediate) success.

A growing number of Americans are leaving trust funds behind for their pets

A pet trust ensures that an animal receives financial support and care if its owner can no longer care for the pet. Some lucky dogs have inherited millions of dollars from their owners.

Just because a big name company is going public doesn’t guarantee a successful stock

A reporter dove into how highly anticipated IPOs can still be risky, and why retail investors should be wary of investing right away.

PayPal was started in 1998 by Peter Thiel

By the year 2002, PayPal went public for the first time—but that was far from the end of its business story. eBay later bought PayPal, then eventually spun it off. PayPal IPO'd for a second time in 2015.

Explore Bessemer's anti-portfolio of missed opportunities

From Pinterest to Yelp, Bessemer Venture Partners—one of the most well-known VC firms—has invested in many successful companies over the years. But the firm has also kicked itself for passing on a few great opportunities, like Apple and Google. Check out the other companies in Bessemer's "anti-portfolio" here.

Bezos has frequently cited a 1999 article titled Amazon.bomb to illustrate how dire the early predictions about Amazon got

Over the years, Amazon founder Jeff Bezos often recalls how wrong the predictions in the 1999 Barron’s cover story were. Among other things, that article declared Amazon’s entire business model to be unsustainable and destined to fail, noting its lack of profit and dependence on a massive amount of capital to fund its growth.

The COVID-19 pandemic both boosted Peloton's business and shook it up completely

While demand for Peloton's at-home fitness equipment soared during the pandemic, the company didn't necessarily have the infrastructure to support the breakthrough sales. In 2021, Peloton bought Precor—a fitness equipment manufacturing company—to help boost domestic production and decrease a backlog of orders.

Peloton hit a million subscribers in June of 2020

The COVID-19 pandemic ushered in record-breaking sales for Peloton, as gyms closed and at-home fitness classes became the new norm. However, Peloton struggled to keep up with the increased demand. As the COVID-19 pandemic's lockdowns lifted, many people returned to the gym, reducing their need for on-demand at-home fitness classes. Some say Peloton's strong subscriber base is the ticket to helping the company eventually become profitable.

See a ranking of the most popular websites on the World Wide Web from 1995 to 2023

America Online's homepage was the most popular website through mid-2021, when the Yahoo homepage took over and, shortly afterward, became the first website to reach 1 billion monthly visits. It would not be dethroned until early 2006 by Google, a major player in the search engine market.

FTX, one of the world's largest crypto exchanges, collapsed in 2022

As crypto markets declined during the post-pandemic slowdown, Sam Bankman-Fried propped up the markets with billions he'd earned leading FTX, one of the largest crypto exchanges. Then, in one of the most rapid financial implosions in modern history, the exchange collapsed as investors rushed to withdraw money.

Amazon has experienced relentless, if occasionally bumpy, growth since its founding

From its founding in 1994 to a slew of acquisitions and new products and services launched in the decades since then, Amazon has experienced relentless, if occasionally bumpy, growth. This timeline from The Verge lays out some of the major events in the company’s story, including its IPO, rollout of its lucrative cloud-computing division, and much more.

Pizza Hut helped pioneer online food delivery in 1994 with PizzaNet, a website that allowed users in select areas of California to order pizzas online.

Listen to a 2026 interview where Bumble's CEO said its stock is down 96% since its IPO 'for no reason'

CEO and Founder Whitney Wolfe Herd said the company is still performing very well. She added that the business makes $1B per year and referred to it as profitable. She went on to say "who knows what people trade stock on?" and that she believes the stock market has written Bumble off as if it were debt

Sears filed for Chapter 11 bankruptcy in 2018

Although the retailer may have failed financially speaking, some argue that longevity in itself is a success—the brand operated for over 130 years before that bankruptcy filing, after all.

Internet domain names can be worth millions of dollars

And yet, the mysterious man who owns Milk.com likely isn't selling his valuable site any time soon.

Warren Buffett has been criticized for avoiding investing in tech stocks during the 1990s dot-com boom, as he wasn't confident in the future growth of the tech industry.