Theranos and Pets.com are among the most well-known startup failures in business history.

Pets.com—an e-commerce pet store webpage—is a prime example of dot-com companies burning through investments. Despite being a popular and well-known brand, the company struggled to generate enough revenue to become profitable. After raising approximately $82.5M in its February 2000 initial public offering, Pets.com filed for bankruptcy in November of that same year.

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.

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.

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.

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.

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.

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.

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.

In the 2010s, dozens of female founders were celebrated on the covers of business magazines like Inc. for their recent startup success, from Emily Weiss’s Glossier makeup brand to Steph Korey’s Away luggage company. But many of these companies were also the subject of large takedown articles around the year 2020.

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.

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.

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.

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.

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.

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.

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

Once valued at $47B, WeWork promised to revolutionize office space—but rapid expansion, financial red flags, and a pandemic-driven shift in work culture led to its 2023 bankruptcy. This overview looks at its rise and fall, and what’s next for the coworking giant.

Silicon Valley Bank—the 16th largest bank in the US—served many tech startups in the area as well as many venture capitalists. The bank collapsed in 2023—in a single day, bankers took out $42B.

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.

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.

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."

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.

There’s no shortage of potential culprits for Sears’ death, from hedge fund manager Eddie Lampert, to Amazon, to the 2008 stock market crash.

The attempts with Falcon 1 endangered the company's future but provided valuable information from which to iterate and follow up with the successful first privately funded orbital launch in history and multiple ISS resupply missions.

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.

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.

Twitter began in 2006 as a side project and grew into a major global platform, widely used for news, activism, and political discourse. Despite mainstream success, it faced ongoing management turmoil, business struggles, and rising concerns over misinformation and user safety.

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

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.

This podcast episode chronicles the complete rise and fall of WeWork—from its founding in 2010 to its eventual 2023 bankruptcy.

In March 2023, Silicon Valley Bank—the nation's 16th largest bank at the time—collapsed after a rapid run on its deposits. Among other factors, the bank had placed more than half of its investments into long-term bonds, leaving it without the necessary cash on hand as its clients, largely start ups, panicked and withdrew their money at the same time. This visualization lays out the timeline and impact of the collapse.

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.

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.

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.

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.

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.